You do this through a timeless policy of charity and trust. Act charitably toward your future self, and in turn you inherit a better life. Be accountable to your past, and in turn you have a trustworthy future self whom you can hand work off to.

Disconnection

Many people are woefully disconnected from their future selves, living in a kind of eternal present where “the future” is an imaginary place, and their “future self” is a stranger whose problems don’t matter. Some examples that come to mind:

• The internet is a graveyard of barely-started projects. I was looking for Substack names for a new writing project, and for every name I tried, I found a person who claimed it years ago, wrote 1-2 posts (or just “coming soon”), and then never posted again. If you’ve ever shopped for domain names or landed on a random person’s website by some other means, you’re familiar with this pattern. Their latest post gushes about, “Whoops I haven’t posted in so long, sorry, but I’m going to be posting more consistently from now on!” and it’s from 2013. And it’s tempting to judge them, but I know the exact experience that causes people do this, because every time I publish a post, I distinctly feel like “that was easy, I could do this more often, like once a week for a while.” But I know better: that feeling is miscalibrated, it’s present-bias, and it can disconnect me from the reality of my future self. We get an emotional high from finishing work, and in that highly motivated state we commit to more work that our future selves just can’t deliver.

• At my job I often see this pattern where someone gets excited about a new project or initiative, yet somehow I know the momentum isn’t going to last. Maybe it’s that I know their other responsibilities will pull them away; maybe I think they’re underestimating the work it’ll take; but it’s just a sense I get, and it’s always right. I know if I just wait a week or two, the project will stall out and be completely forgotten.

• Closely related to the above is the planning fallacy. People are consistently bad at guessing how long a project will take. They underestimate it every time, and even when they know they underestimate it every time, they still underestimate it every time. I see this firsthand, a lot.

• Being bad at planning is both a cause and symptom of a low-control lifestyle, which I’ve written about before. If you’re not connected to your future self, you can’t plan. Then what you call “planning” is really just wishing. And when your plans fail, you’ll be surprised, but no one else will be.

• When you ignore your future self, you demonstrate high time preference: you systematically prefer rewards and pleasures that come right now, even if it means depriving your future self of better things. High-time-preference people are easy to predict, and that’s how they get taken advantage of. You can convince them to buy junk food on their way out of the pharmacy, just by putting the junk food in front of their face. You can get them into credit card debt and gouge them with interest payments, just by letting them spend money they don’t have.

• Closely related: people can’t do things at the proper time, even if they once intended to. “Sign up now, cancel anytime!” says the checkout page on a service they don’t need. The important subtext, never spelled out, is “But you won’t, lol.” If the time of action and the time of benefit don’t line up perfectly, the thing never gets done.

The timeless justification

So, there are warnings listed above and lifestyle benefits listed below, but I feel like the tallying of benefits doesn’t quite work here; there’s a mental shift that’s needed.

It was easy to see the benefit of Connecting to our past selves: I can recall things from my past that make me smarter or wiser right now. But, how could it benefit me to connect to my future self? Causation only goes one way; my future self hasn’t happened yet!

The decision to care about your future self is not a causal transaction, it’s a policy. Policies are timeless decisions. The result, of course, is that the future self you arrive at will have already been cared for by a past self. You didn’t cause it in a single moment, but you installed it as a stable pattern in your life. This is roughly the intuition behind timeless decision theory: a decision is not just a causal event, it’s also an expression of the kind of person you are. It addresses the question, “What kind of person does this make me, and what kind of future do people like me tend to find themselves in?”

If you’re thinking in this frame, treating your future self well is justified entirely by you appreciating or wishing for good care from your past self.

In this frame, you solve problems timelessly. After they crop up, you respond by making sure they won’t happen again. For example, if I learn that I’ve missed a promising recruiter’s message on LinkedIn, before I even start thinking about “What should I message this person now that I’m a month late,” I first ask, “How do I make sure this doesn’t happen again? Have I set up LinkedIn forwarding to my email? Do I check my email often enough? Do I filter out the annoying emails so I can check emails in earnest?” Or, if I’ve misplaced something in my apartment—once I finally find it, the most important thing is that I put it back in the first place I originally looked for it, so it’s there next time. This is what it looks like to solve problems timelessly. It’s a lifestyle of compounding benefits.

In another frame, this is the classic virtue of charity: it’s non-transactional love. You don’t know for sure that you’ll get a payoff—you probably will, eventually / on average / in the long run, but the future is uncertain. It’s not cash in your hand; the benefit is indirect and hard to predict. That’s why it’s a virtue and not a transaction.

If your past self let you down

A lot of people have been neglected by their past selves. If that’s you, then you have to be the hero, like that trope of the person who had a bad upbringing and then says, “I won’t make the mistakes my parents did,” and doesn’t. You do a mini version of that when you break the bad habits and patterns your past self left you with and put in the work to make life better for your future self.

If your past self lifted you up

It’s a pay-it-forward kind of thing. It gains a momentum of its own. I receive care and support from my past self → I feel gratitude → I express that feeling by paying it forward to my future self.

It is so easy to be me. My body is strong; I have good relationships; I have a good job; I have a good apartment; I have savings. This is due in part to the fact that my past self loves me. What kind of person would it make me, if today I just sat and absorbed all those gifts and put nothing more into the world?

The benefits of connection

And here are the practical benefits you receive, once you’ve established that timeless connection in your life.

Inherit habits

Building a good habit is one of the best gifts you can give your future self. They get not only the direct benefits of the habitual practice, but also the habit-ness of it—the ease of fitting it into regular life; the way it has no psychological cost, because it’s already the norm!

Make planning easier: one less unknown

When you make a plan, you’re trying to solve an equation with multiple unknowns: What will the whole situation look like in six months? What resources will be available to me? What obstacles will appear along the way? There’s a lot that’s out of your control when you try to plan. But there’s one unknown in every plan that often gets a free pass: Who will I be when the time comes?

If you don’t know your future self, you’re writing plans for a stranger. You’ve declared that you’ll finish the project by September, but you have no real sense of what September-you is going to care about, how they’ll be feeling, or whether they’ll even remember why this project mattered. The plan is nothing more than a wish.

Knowing your future self collapses this whole category of unknowns. You have an idea of what that person will be capable of, what will exhaust them, and what will actually motivate them when the time comes. It’s not perfect knowledge, but a basic calibration is possible.

Stack your brainpower

You have aspirations to do this-or-that task, but it’s unfamiliar and challenging. The act of preparation lets you stack your brainpower across time, so there’s less to figure out in the moment. The novice stage of any activity is always a messy deal where your brain is trying to learn a hundred things at once. You can reduce this stage! Some examples from my life:

• In college, when I was thinking about starting a real weightlifting program for the first time, I spent about a week just reading about programs and exercises and watching videos. So when I started the workouts I felt ready, had motivation, had good form, didn’t hurt myself, etc. Having a baseline familiarity with everything was also important for the self-consciousness of it all: I might be starting with really low weights, but at least I don’t look clueless.

• Years ago when I got an interview opportunity at Microsoft for a type of role I never really knew existed (but thought I’d be a good fit for), I spent every day for a month preparing for that interview loop—not only drilling the job-relevant technical writing skills, but grabbing tangential knowledge like learning theory; not only learning about the hiring team, but studying the whole structure and history of the company; not only communicating promptly with the recruiter, but social-media-stalking her and each of the interviewers she mentioned. During my meals I’d watch keynote speeches from the CEO. I was aggressively consuming context, so nothing would surprise future-me. 30 Patrick-days’ worth of attention, all closing in on this one interview day. You are very capable when there are 30 of you!

• When I joined my Muay Thai gym I got through the novice stage quickly, and enjoyed it. I had done some research about what Muay Thai is like, what the gyms are like, what you do in classes—all typical questions a newcomer would have, that you can in fact answer for yourself before you even start. I see newcomers at my gym all the time, and despite how good a learning environment it is, they look uncomfortable and overwhelmed. You can reduce this!

This aggressive context-gathering may be especially natural for generalists, because you get to approach the same subject through many different modes. For example, I genuinely enjoyed reading about the history and sub-schools of Muay Thai.

Greater trust → greater responsibility

The better you know your future self, the more willing you are to depend on it.

If you barely know a colleague, you won’t delegate anything too important to them. But if you’ve worked with them successfully for years, you’ll hand over critical work; they have a track record. Your future self works the same way. When you’re disconnected from it, you can’t trust it to follow through. Sensing this, you might hesitate to ever commit yourself to long-term projects.

But if you know your future self through policy—if you’ve been sending it messages, reviewing what your past self left for you, tracking how your predictions played out—then you develop a trusted relationship with it.

• Stick to long-running commitments. I do this with fitness planning, for example. I’ll sit and plan a full year, sometimes longer, of exercise programs: in the winter I want to gain weight; in the summer I want to cut; I’ll do three months of lifting and easing off kickboxing, then three months of more kickboxing but still gaining weight, etc.
  

• The programs are tracked in my goal sheet, and then I’ll make a separate list or sheet for the actual exercises I work through. I can literally choose what body I’ll have, and when.
  

• Return to the present. If you can reliably push tasks and thoughts into the future when they’ll be more appropriate, it frees you up to ignore them right now. If you’re unable to ignore things now, they pull you out of direct experience. Good things in your future that you can’t ignore make you impatient! Bad things in your future that you can’t ignore make you needlessly worried! Passing things to the future is a hack to get you back into the present.

• Show more ambition. You’re not alone when you take on big plans; you have a team of future selves you can trust.
  An ordinary tree can tear apart concrete. It has no muscles, no nails, no teeth, but it has perfect coordination with its future selves. Every day it dutifully swells its roots a little larger, pushes a little harder against its obstacles, over years and years. You can be like this. You can decide to put out your roots and grow, even if you find yourself surrounded by “concrete,” as long as you know your future self will continue the work.
  

How to connect

Like I did in the past-selves post, I’ll list my favorite ways to strengthen your connection to your future self:

Make self-predictions

Try to predict what you’ll do in the future. The act of writing down your predictions makes them real and keeps you from conveniently misremembering your past beliefs.

Tools like fatebook.io make this easy for you. Write your prediction in plain text, like, “By the end of this month I’ll finish my project,” and the tool smartly interprets the date and takes your own % likelihood prediction. When the outcome is due, it emails you so you can make a ruling.

This can benefit you in both directions: it motivates you to do the thing, and it reminds your future self of what you believed and what was important to you.

Send messages to the future

In my grade school we did a time-traveling exercise that I still remember fondly. In kindergarten our teacher had us write letters to our future selves. And in eighth grade, those of us who had been there in kindergarten got to open and read those letters—we’d long forgotten them, but the school had saved them.

It’s very easy to do the same thing as an adult. Email clients like Gmail have a delay-send feature, and there’s no upper limit on how far ahead you can schedule messages to send. So, many years ago I started writing emails to my future self. I’d write a little entry on what I was thinking about lately, what I was struggling with, etc., and then schedule it to send to myself in the future. I’d copy it and send it to different dates—5 years, 10 years, 20 years ahead, etc.—so that multiple future selves could open and reflect on its message. Every two years or so I get a reminder in my todo app to write another batch of emails to my futures selves, and I do it.

At this point I’ve received emails from multiple past selves. From as far back as 2014 and as recent as 2021.

Technical note: For convenience, I send these emails from my junk email address to my main email address, because in Gmail your scheduled messages hang around in the inbox until they send, which is annoying if you’re checking that inbox regularly. The point is to write the message and then forget about it.

Send tasks to the future

Put task reminders and project notes somewhere where your future self will see them (but that you can ignore right now). This is solved by any kind of todo app or system that can schedule notifications for the future—as long as you trust your future self to check and read those notifications! I use ticktick, which is more-or-less a clone of todoist.

Stay organized

Your future self is occasionally going to need to look up your stuff. Organize your thoughts and work so your future self can easily navigate them. That’s the theme of The two rules of personal organization. Your future self is a different person, so give them context! Go watch Memento again: we are all Leonard Shelby. We have the same condition, just less severe. Losing short-term memories is the norm!

Conscientiousness is future self-interest

Conscientiousness is the psychological trait of being “responsible, careful, diligent, organized, and goal-directed,” and it predicts income, health, longevity, and similar outcomes. What is conscientiousness, other than nurturing your future self? What is low conscientiousness / impulsiveness / ADD behavior, other than neglecting your future self?

They say “Treat yourself!” I ask, which one?

“Treat yourself” is used to justify present indulgence. But it doesn’t specify the present. You should love all of your selves: the past selves, present, and all possible future selves (weighted by the probability that they’ll come to be).

What we call self-denial or even austerity at one point on the timeline may be self-love or even indulgence at a later part of the timeline. And the later period might last longer!

Bittersweet

There’s a lot of upside here, but it’s not all upside. Having a relationship with your future self is a bittersweet thing, because one day your future selves will disappear. It’s like a parent who loves their kid but knows the kid will eventually move out. Being in communion with your future self means facing the fact that you’re going to die someday.

Indeed, the whole mindset of “living in the present” has a lot of advantages (and like I said, it’s easier to get into when you can reliably punt stuff to the future), but being in that state 24/7 is a cope. You’re coping with the fact that your time (your future) is limited, by forcing yourself not to think about it. It’s the blissful ignorance of the animal kingdom:

When you pick up the fantastic tool of mental time travel, you also pick up the grim knowledge of the human condition. This is your inheritance as a thinking human: both the grimness and the dignity.

Why connect?

My reasons, in no particular order:

Reflection: Look at your past selves to see how you’ve changed, and how you haven’t. You notice how certain decisions back then determined who you are. You see the tiny seeds of thought that grew into prevailing patterns and frames that you take for granted now. You see old intentions that failed to take hold, and big changes that had no intention behind them at all. You learn what worked and what didn’t; what was important and what wasn’t; this is wisdom.

Accountability: You’ll notice the missteps your past self made. This might motivate you to conduct yourself better in the present, because you know you’ll be watched by a different person in the future.

Consistency: In productivity coaching my job often involves connecting people to their past selves: “That sounds like a plan that really motivates you. But I want to confirm, you told me this other plan about two months ago. Do you feel differently about it now?” They say “oh yeah” and check on the old motivation: Is it still there? Has it evolved? I don’t automatically side with their past self, like “You made that plan so now you have to stick to it!” But they need to be in conversation with their old motivations to find the best path for their present self. Too much disconnection leads to the typical ADD pattern of always starting new plans but never following through.

How to connect

Journaling and reviewing

If journaling comes naturally to you and you can keep your journals somewhere secure, you’re all set. Whether you write daily, weekly, or sporadically; whether you write matter-of-fact reports or deep emotional expression: your journal is valuable as a record of your past self’s own thoughts.

(Keep those records safe, so they survive into the future. My journal is digital, synced across devices, and backed up to multiple cloud storage locations. It’ll outlive me.)

Periodically go back and read old entries (I have a reminder to do this monthly). You receive not only the text content your past self wanted to express, but the whole frames of mind that those familiar words invoke. Hindsight lets you see patterns and influences that were invisible to you at the time. What did you express about yourself back then, without even meaning to?

For example, if I look back far enough, I notice how my writing style changes. I find turns of phrase I used back then that I don’t use anymore. So I ask, “Where did that come from? What was I reading or listening to at the time that made me write that way? What people and ideas did I admire, and why?” When you journal, you think you’re simply recording what is; but with temporal distance, you notice how influenced you were by whatever else was going on at the time. The whole context reveals itself.

If journaling doesn’t feel natural to you, that’s fine, there are easy alternatives.

Your sent items folder

Your email application saves your sent messages and makes them searchable. That’s a record of your past!

You could start with a date filter: show the sent items from this month, one year ago. As with journaling, more is revealed in hindsight than you intended. You thought the email was just conveying the literal information, but now you can see your state of mind, your goals, and how you wanted to be perceived back then. The further back you look, the more you get the impression you’re reading the mind of a different person.

Your digital calendar

If you use a digital calendar like Google Calendar, you can navigate back and look at your schedule in the past. This is probably not very information-rich, but it’s something. See who you were meeting with, what you were prioritizing, and how you were spending your days.

Your old photos

Your personal photos are probably backed up to iCloud or Google Photos, in addition to whatever social media you post them on. What will you find if you scroll through your photos from this month one year ago? Photo apps do this randomly now, showing you “highlights,” but you can do it intentionally, too.

My wife does this almost daily: Facebook shows her posts “from this day, X years ago,” and she reflects on what she was doing, how she felt, and what was important to her back then.

Your old goals

I use a custom spreadsheet for tracking goals over time. If you regularly set long-term goals, then whenever you finish a season or year or other goal-period, you can look back and review that period. Did you get your goals? How? Or why not? What surprised you?

Construct a visual timeline

Draw a timeline of the events that make up the major arcs of your life. I used a digital tool that requires some setup, so I gave it its own page: Keep a visual timeline of your life. And below is one thing you could do with that information:

The evolution of ideas

Two of the categories I used in my timeline are about ideas: Philosophy (ideas or ideologies that were important to me; things I read that stuck with me) and Lifestyle (goals and values I had; insights about myself). I ended up with about 10 major things in each of those categories. Looking at ideas across time is interesting, because ideas are four-dimensional, like we are: they continuously grow and combine and take new forms as time passes.

So in a separate chart, just a flow chart with arrows (I use Scapple), I mapped how earlier ideas had caused or influenced later ones in my mind. Knowing the dates of each phase helped me get the order (and causality) right. Now I have a lineage of the major beliefs and values that have influenced my life up to this point.

That chart revealed all kinds of cool things to me:

• I can see how general curiosity and general creativity are two values that were there from the start / from early childhood. Their “cause” is too muddled to think about, but I see how they influenced the way I responded to other things I came across.

• I can see what media entered my view and when, and how it nudged me toward other media. Blogs, YouTube channels, books—you consume something, find that you like it, and then monkey-branch onto “more things like that,” and on and on.

• I can see which real-world events had the greatest effect on my ideas and values.

• I’m surprised at what a roundabout path I took to get to where I’m at. We are biased toward thinking we’ve “always been this way” besides one or two big changes we can remember. But the truth is I’ve had whole multi-month phases that I mostly forgot about. There have been more versions of myself than I thought.

A note on judgment

This exercise has you looking at your past self with the advantage of hindsight. You’re going to see a lot of surprises, mistakes, and misplaced confidence. Remember that this is about learning, not judging. Treat your past self like a close friend whom you respect. Do a fair evaluation, and where appropriate gently declare “That missed the mark.” For serious errors, forgive your past self. And extend gratitude where it’s due.

If you’re constantly a harsh critic of your past self, you’ll inevitably start to anticipate similar criticism from your future self. And that’ll give you an emotional backdrop of anxiety and resentment in the present, like “What’s the point, it’ll never be enough.” Avoid that vicious cycle! Be kind now, so your future self is kind, too.

Your relationship with your future self is what we’ll look at in the next post.

You are a four-dimensional being.

And it’s fitting, because you live in a four-dimensional world. Three spatial dimensions, plus time, the dimension we all move through at a nearly-constant rate. In Einstein’s famous relativity equations, time is treated much like the three spatial dimensions. And those are the best equations we have for modeling the physical world. So even though we experience time much differently than we experience space, that may be more a quirk of our own minds rather than “how things really are.”

Consider how you can cast your consciousness around three-dimensional space: you can pay attention to what’s happening in some distant area of space that you think is important, using your eyes and ears to construct the picture as if you were right over there. In some sense “you” really are over there. Not your body, but your consciousness, your self. (And many would argue the self is an illusion, but we’d still say the illusion is presenting itself over there).

Now notice that you also have the phenomenal ability to cast your consciousness in the fourth dimension: forward and backward in time. You can be conscious of the past through memory, and of the future through prediction and planning.

“But memories are faulty, and prediction is often very difficult.” That’s true, especially as you go further away—but that’s really no different than with space! It’s difficult to see or hear things that are far away, and even more difficult to smell or touch them, but that doesn’t stop us from trying. And of course we use technology to extend the range of our awareness in space. So too with time! In the next two posts I’ll list all my favorite technologies for augmenting your time-traveling ability.

You can become a consciousness that extends across time, dancing in and out of moments in no particular order, like the aliens in that popular 2010s movie [redacted, spoilers].

The shape of a human

You think of your body as something like this:

But this is a more accurate illustration of what you are:

This is your four-dimensional body: a continuous chain of 3D body-instances, each connected to its neighbor as surely as your head is connected to your neck. You have definite bounds in length, width, height, and time. This is the shape of a human.

You can look down your vertical axis and see your feet. And your conscious mind is connected to your feet, sending neuromuscular commands and receiving sensations as feedback. And your unconscious is also connected, regulating the exchange of blood, lymph, and everything else with your feet. Up and down the vertical axis, you are in sync with yourself. What about the time axis?

What do you see when you look at me? A grumpy old man who never answers questions? Who mixes everything up? Who’s kept busy by getting his meals? That’s not me. Me… I wear shorts. I’m nine years old. I can run faster than the train. I can’t feel my aching back anymore. I’m fifteen. I’m fifteen and I’m in love.

Why think about this?

You were there in the past. You’ll be there in the future. Are you acquainted with your one-year-ago self? Do you judge it? Does it judge you?

Would you like to talk to your future self? Send messages forward in time? Would you use something more reliable than just your future self’s memory of old thoughts?

It’s a terrible affliction to be disconnected from your past and future selves—as serious as being disconnected from your feet. I know someone who struggles a lot with personal organization. “Why are these labeled this way?? Let’s look in the history and see who labeled them… I probably did…” They talk about “I” as if it’s “those mischievous elves”: someone foreign and incomprehensible. How terrifying it must be, to wake up everyday completely new, not knowing what you’re walking into! That’s the extreme, but we all have moments of forgetfulness like this—moments of disconnect.

When it’s working, on the other hand, mental time travel is one of our superpowers as humans. I’ve heard it argued that it’s the superpower that led to humans dominating the earth: A proto-human starts trying to make sense of their past or future self, but that requires them to see themself “from the outside.” So they develop a theory of mind, which they can then use to understand other people, too. Soon everyone starts trying to understand and influence each other, and this recursive social reasoning game creates the long-term evolutionary pressure to promote more and more powerful minds. And here we are.

In the next two posts, we’ll look at specific ways we can communicate and coordinate with our past and future selves, and what superpowers we can unlock.

It’s a social force that is parallel to Moloch, but different. Moloch says we all must make the game harder for ourselves because uncoordinated agents have to escalate efficient competition in order to survive. This thing is more like, we make the game worse because we each take such a narrow, reductive view of the game that we don’t notice what we’re doing.

Economists see everything through their overly reductive model; lawyers see everything through their overly reductive model; etc. But worse still, everyone defends the meta-system of “give each person an overly reductive model,” because it makes them feel special! “Universities don’t just churn out specialists—they create a credentialed class psychologically invested in defending the system that elevated them, even when that system causes harm.”

Not only special, but comfortable. “If public health professionals are thinking about the problem, then I don’t have to,” and so on, for a thousand different problems we hear about but don’t want to engage with. Experts don’t have to be malicious or even incompetent for this system to fail; it fails because their expertise is just too narrow to catch the second-order problems they’re causing.

“We need generalists—people who refuse to be watchers in their own lives. Before industrialization, healers and polymaths wove together physical, spiritual, and social knowledge.” “Read outside your lane—doctors, study economics; economists, learn biology.” And so on. Become an expert on the chaotic interaction between fields.

What is indefinite optimism?

Peter Thiel coined the term indefinite optimism in his book Zero to One to identify a flaw that plagues startups. It’s the vague expectation that the future will improve, without any concrete plan for how that improvement will happen. Definite optimism, by contrast, confidently makes plans to bring about a better future.

Indefinite optimism, says Thiel, happens not only to businesses, but also at the broad societal level. He warns us that contemporary America is guilty of it—we have hope that things will improve, but we mostly think the magic of stock market growth will get us there (today you could argue we’re betting it all on an AI-driven productivity boom, which is more of a plan, but think of America just a few years ago, without that hope).

And if America is indefinitely optimistic, maybe I am, too.

The indefinite optimist

Thiel’s diagnosis also applies at the personal, life-planning level, and I’ve found it to be a really useful, if scary, tool for that. When I was in college I had severe indefinite optimism about the future—how could I not? Up to that point everyone had been telling me I had my whole life ahead and that I could be anything I wanted, and they were basically right! So I could take any possible future that sounded kinda cool and entertain it as a serious possibility. A fantasy that doesn’t quite admit it’s a fantasy.

I wondered what it might be like to work at a startup. To run a startup. To manage a team. I wondered what it would be like to live in Ireland for six months and just read and enjoy nature. I assumed I’d get rich enough to afford a personal chef.

And when I graduated college, the indefinite optimism continued. Even though I got a job and planned to stay with it, it never really sunk in how that would limit my future possibilities.

Indefinite? That’s bad :(

In 2018 I traveled to Italy and saw beautiful estate houses with enclosed courtyards. I loved that feature of the architecture. And somewhere deep in my mind, radiating warmth to the rest of my experience but mostly staying out of view, was a thought, “maybe someday.”

“But how would you ever get that? Do they even make houses like that in America?” I don’t know, and I didn’t ask. I was in Italy, enjoying it, and I just felt good with the idea that I could possibly live in a building like that one day. That’s it. That’s what makes it indefinite!

But future hopes come at a cost. To simply appreciate the beautiful courtyard is free, but that’s not what I’m talking about. I’m talking about the inkling of an expectation of some gain in the future. It will either come to pass or it won’t, and if it doesn’t, then I’ll experience that adjustment of expectations as disappointment.

Optimism? That’s good :)

What do you daydream about? What are the pleasant future daydreams you have? The future-fantasies that come with a small spark of “but maybe” that sets the whole thought alight?

It’s ultimately a good thing that you can grab onto ideas that are just at the edge of what’s possible for you. That’s the seed of ambition. That’s the start of the hero’s journey.

But it does need to start. Or, the hero decides this wasn’t the proper journey after all, and that’s fine too. Either way something must be done; passive hope doesn’t work for startups, and it doesn’t work for people.

Make a list

If you sit down and try to make a list of all the indefinite optimisms you quietly harbor, I bet it’ll be difficult. These ideas tend to slip out of your consciousness; you don’t want to examine them, because either you’ll deem them impossible or not worth it (in which case they’re destroyed), or they’ll be loaded up with a plan of work to realize them.

I tried to list mine, but actually most of the list was added periodically in the following two or three years.

Start the list, and just know that it’s there. Then, when you feel that spark of “what if,” that’s when you write it down. I found I could only notice my indefinite optimisms when I was feeling them.

Eventually you’ll have a pretty substantial list of things you’ve secretly hoped for but which you have no plan to get and might not even be possible. Scary stuff!

Return to your list

What then? Do you make a plan to acquire/achieve each thing on the list?

Your indefinite optimisms are not goals. They might become goals, if they hold up under conscious consideration, but they very well might not. They are whimsical—they don’t promise to be worthwhile, and they’re not urgent for you to attend to.

Look at your list a few years after making it. Ideally, look at it when you’re considering undertaking a big life commitment that will collapse your future possibilities:

• going to college

• moving to a new area

• taking a new job

• living with partner

• getting married

• having kids

Then you can ask, “Which items on my list will most likely be ruled out of all future possibility, if I make this commitment?” Maybe you’ll decide to cram a few of them in before taking the leap to the next stage of life. That would be like doing a micro-retirement, but more general.

But this process is not just “plan to get the thing or painfully give it up.” Reality is more forgiving than that! When I revisited my list:

• 7 of the 26 things had since been achieved, just incidentally, without me remembering they were on the list. In retrospect I wondered why I even considered these things “indefinite” at one time. Perhaps by writing them down, I encouraged my subconscious to hold onto them and subtly work toward them.

• 4 items were no longer appealing to me—my interests had changed—so I dropped them with no grief. In fact I always value opportunities to look at my past self and see how I’ve changed.

• 12 items are still possible*, and I moved them into other lists/notes/projects where I can take active steps toward them.

  • *Sometimes your wants are overly specific and demand an overly strict course of action. Loosen them up by asking, “What is it about this that appeals to me?” I wrote down “Live off the grid hunting and gathering for a short time,” but I don’t have wilderness survival skills and I’m not really interested in learning them. What’s the essence of that want? I think it’s just being completely detached from Internet-era technology and being around nature all day every day, and seeing how that changes me. I can do that from a cozy cabin in the woods; it’s certainly possible in my future.

• And 3 items, I still would’ve liked, but I don’t think they’ll happen in my life. So I mourn them a bit, which is really just mourning the mortal nature of man; we’ll die someday, there’s never enough time to do it all, etc. It’s good and right to feel sad about this from time to time. Consider the alternative: you don’t get everything you wanted in life, your responsibilities become more restrictive, you grow older and less capable, and you refuse to think about any of this. What might that do to your mood? To your spirit?

Do it all again

What’ll I do next, now that I’ve faced down my indefinite optimisms and grounded them in real decisions and actions? I’ll keep the list, and keep adding to it. Why would this be a one-time thing? I haven’t changed; I know I’m going to keep finding crazy incredible things to vaguely hope for—maybe because I’m an American, or maybe because the world really is full of cool things and it’s a great time to be alive. The optimism stays, and the definition will come in due time.

It’s a simple way to optimize your sleep, completely free, using only some background scientific knowledge and a little math.

(But this is not any kind of substitute for the basics of sleep optimization: get some exercise, don’t drink too much, don’t eat too late, don’t stare at bright screens too much, etc. etc.)

What are sleep cycles?

When you sleep, your brain activity follows distinct patterns that researchers call sleep phases. Broadly, they are light sleep, deep sleep, and REM (rapid eye movement) sleep. You move through them in order, and a single run of all the phases is a sleep cycle.

Most people go through four or five sleep cycles in an ideal night of sleep.

Your experience with sleep cycles

When you wake up near the end of a sleep cycle, you feel alert, and when you wake up in the middle of a cycle, you feel groggy and disoriented. Researchers have called this variable grogginess “sleep inertia.” I’m sure you’ve experienced both disoriented wake-ups and alert wake-ups. In the absence of illness, alcohol, or sleep deprivation, it’s almost always a matter of sleep cycle timing.

Now, how can we use this to improve our wellness and productivity?

Smart wake-up

Your phone alarm app might have that “smart wake-up” feature, where it has a range of time in which it can go off, and it tries to pick the point right at the end of a sleep cycle to wake you up. It’s a great idea, but your tech can’t do it. Sleep cycles vary in length from person to person, and the first cycle usually varies in length from the others. Your phone or wearable fitness device will measure movement, heart rate, temperature, etc., but none of those are reliably linked to sleep cycles. That’s why the “hypnogram” chart that your app produces is often erratic without consistent patterns. It’s not good data!

There just isn’t much signal here

You’d need an EEG device measuring your brain to really know. A few years ago, however, I realized I could figure this out from just my own wake-up experiences and math.

Find your ideal sleep length

The first bit of info you need to collect is the length of your ideal night of sleep. This could take a while to set up: you need a night when you’re totally free of sleep debt and when you have enough slack in your morning schedule to wake up naturally. And you should have been going to sleep at the same time the last few nights, so your circadian rhythm is as regular as possible.

Then you wake up, check the time elapsed, and record it.

Some people are so conditioned to their alarm clock that without it they’ll keep sinking back into sleep for several more hours, even without any sleep debt. It helps to set an intention before you go to sleep—literally say to yourself, several times, that you’ll check the time when you wake up naturally in the morning. That sets up your subconscious to push through and exit sleep when those four or five cycles are complete.

You might have to do this several times to be confident of your measurement. Maybe that’s annoying work, but again, this is something you’ll only need to do once (or, once per major biological change in your life), and then it’ll be useful every day.

Once you’ve got your ideal sleep length, that can be hugely beneficial already. For years I would try to get at least eight hours of sleep most nights (because that’s the standard advice), and I had a hard time waking up every morning. But some mornings, for whatever reason, I’d naturally wake up a bit earlier than eight hours. When I learned about sleep cycles I finally noticed what this was: a full night of sleep (five cycles), for me, lasts about 7h 40m.

That means every time I unthinkingly set my alarm for “eight hours,” I was sleeping an unnecessary extra 20 minutes, and during those 20 minutes I was starting a new sleep cycle, only to cut it short (!) with my alarm, causing me to feel groggy.

So now I sleep for less time and wake up feeling better. But the optimizations don’t end there.

The n-1 cycle night

If you wake up at the end of a sleep cycle, you feel good and alert. “So if I set my alarm for exactly four cycles instead of five, I’ll still wake up alert?”

Yes. I’ve run this experiment enough times that it’s not an experiment anymore. If I’m working on something late at night and I go past my planned bedtime, it’s better for me to stay awake longer to get exactly a four-cycle night, rather than rush to bed and get four-and-a-half cycles.

I wake up very alert, maybe even moreso than with five cycles (because, I suspect, there’s a physiological boost of cortisol or adrenaline or something when your full night of sleep is “cut short”).

“Wait, so I can just skip that last cycle??”

No. Although you won’t feel groggy after an n-1 cycle night, there are other drawbacks. I’ll feel drowsy in the late afternoon (and probably should nap at that time). If I do it for multiple days in a row, I start to get brief headaches and have occasional moments of brain fog. Obviously those drawbacks would keep getting worse if I kept it up.

But in one-off cases? Say, once per week? That’s a full hour and a half you can get back, for basically no cost. I suspect this is one of those things where modern life offers us maximum stability, but we’ve actually evolved to absorb some volatility without issue.

(P-hat is me)

Find your n-1 cycle time

The way I went about this is I started noticing when shorter nights of sleep gave me a more alert wake-up, recorded that info, and then later I plugged in the math to verify what was going on. An easy method: drink a lot of water before bed. You’ll wake up to go to the bathroom, and because it’s not an abrupt interruption, your body will pick the easiest time—the end of a cycle—to wake up. If it’s roughly 100 minutes earlier than your full night of sleep, that’s probably n-1 cycles. If it’s roughly 200 minutes earlier, that’s probably n-2 cycles, so record that too.

Put it all together

We want to integrate these data points to get the timing of each cycle throughout the night. First we want to know: is your ideal night of sleep four cycles or five (or more rarely, six)?

Generally the first sleep cycle is measured* to last between 70 and 100 minutes, and the other cycles between 90 and 110 minutes. Those ranges mean there’s some uncertainty in when each cycle actually completes for you; it varies from person to person.

The profile of your sleep cycle lengths looks roughly like this.

Fortunately, because we’re only dealing with a small number of cycles, the variation doesn’t add up that much. A total duration under 430m must be four cycles, according to the data we have. Durations of 520-540m can theoretically be reached by either five or six cycles; let’s make things easy for ourselves and say 530 is the cutoff there.

_{*Basic info from sleep cycle research can be found here (or your AI can bring it up for you).}

Use the calculator to align your cycle lengths

If you know your ideal sleep duration and you know how many cycles it is, and you assume, as the research shows, that the the first cycle is shorter and the rest are all about the same length, you can get a good idea of whether your n-1 (or n-2) measurement was correct (i.e. whether it’s really showing the sleep inertia phenomenon or something else was affecting your wake-up experience).

There’s some wiggle room in how it all adds up. A first cycle of 70m and four more cycles of 103m gives you eight hours, but a first cycle of 90m and four later cycles of 98m also gives you eight hours. If you can tweak the balance of cycle lengths so that both your ideal night and your n- night are represented in the same schedule, then you can assume your information is good.

For example, my ideal sleep was 7h 40m, and that’s five cycles. My n-1 sleep was just a few minutes over 6h. If I enter the first cycle as 80m, the latter four cycles need to be 95m to add up to 7h 40m in five cycles (they can be calculated automatically). And that puts the n-1-night duration at 6h 5m, matching my other data point.

So, have a try* at that:

_{*If you’re reading this on Substack, go to the original webpage to use the calculator.}

Use it

And now you know your whole sleep cycle schedule. Keep in mind that lots of factors can mess up your sleep; this is effective in the absence of those. But it is effective.

I get five cycles most nights, and occasionally I get four. On a few dire nights with poor planning, I’ve targeted exactly three cycles to minimize the damage. And on days when I’m sick or injured and want extra sleep, I target six cycles.

Your alarm clock is a good tool, but your body just isn’t designed to spring awake at any arbitrary moment. By considering your sleep cycles, you can use your alarm in harmony with your natural rhythm, rather than against it.

• Agency: The “main character” trait – It’s popular to describe high agency as “Main Character Energy,” referring to the fact that the main character in a story is the person who does interesting things and has unusual experiences. The modern world includes so many opportunities to do interesting things, but also presents us with more tempting lifestyle scripts that keep us stagnant.

• Responsibility: The trait of honorable obligation – The second key trait is responsibility. Responsibility is a moral reality, unlike agency, but it often increases agency in a person’s life – sometimes tremendously. People tend to work harder and more tenaciously when they have someone or something to take care of.

• Control: The mysterious aura of good outcomes – Some people often fail to show up or follow through on plans, not because they lack ability or care, but because “unexpected” life interruptions seem to follow them around. What’s going on there? What is actually within your control?

The relationships between them

When thinking about these three traits in combination, I notice first of all that agency and control seem to be inversely related. Being high in one means you’re more likely to be low in the other. A high-control person is likely to be detail-oriented and risk averse, committing to only what’s “possible/reasonable” within their realm of experience. The high-agency person thinks big-picture and accepts big risks—some unforeseen, probably—to set their plans in motion. You can see then how the high-control person would miss unusual opportunities, and the high-agency person would stumble into unforeseen disruptions that kill their plans.

A friend of mine shared in an Instagram story, “Finally headed to Europe after two missed flights and losing my passport. Send me your summer travel plans!” Traveling to Europe alone as a young woman is a pretty high-agency move. Missing two flights and losing your passport is a very low-control outcome. That pattern is not hard to find.

What, then? Do we choose one or the other? Of course not, this is True Generalist! We simply get very good at both. A person who is both ambitious in goal-setting and consistent in execution is a master of doing things, and we aspire to that.

The second thing I notice is that responsibility can boost both agency and control. I previously wrote:

If everything is chaos at work but you feel responsible for this product shipping on time, you’ll figure out a way to get it done. If your family is hungry, you’ll figure out a way to get money. High-agency actions can be powered by a sense of responsibility…

But responsibility also increases control, if that’s what’s needed! Speaking of losing passports, there was a meme a while back about young adults traveling together and appointing the “airport dad” of the group to handle all the logistics, making sure the plans go smoothly. The subtext of course is that dads are high-control. You’ll find abundant examples in moms too. A person who bears responsibility for others assumes all the control-risk for them, and in doing so he/she becomes better at generally keeping outcomes under control.

We arrive at neat kind of paradox. Agency and control straightforwardly empower you to do things; it’s clear how they each work. But they tend to oppose each other, and it’s easy to get fixated on one while suffering from neglecting the other. Then we have responsibility, which on its face looks like the opposite of “doing things”—a set of extra obligations you have to meet before you can do “what you really want.” But responsibility is a lever that increases both agency and control! Is the moral weight of responsibility necessary to turn you into an ideal, highly capable doing machine? I’m not sure, but we can’t ignore that it does seem to do that.

How this started: I know a couple people who seem to struggle with… just… showing up at a place, at a time. This thing that sounds so easy on paper is very, very hard for them to do in real life. They’ll say they’re going to attend some event somewhere, they’ll confidently name the time and the place, and then it just won’t happen. They overslept; they missed their flight; they were “in the wrong headspace”; their “week got crazy busy,” etc.

In one-off cases, these are simple life interruptions that can happen to anyone. But, like with agency, we see it concentrated around specific people, so we conclude there must be some personal component to it.

Here’s a scenario I like to use to help define this thing: If you had to do a 1-minute task every day for a year, and at the end of the year you’d get a million dollars, but only with a perfect 365-day streak, would you get it? Be honest. Let’s say the task is not physically hard, it’s not mentally hard, it doesn’t cost any money, doesn’t require you to be in a specific city or anything like that—it’s easy in all those respects. Yet I know so many people who would definitely fail the challenge. It’s hard in some way.

Not agency, not responsibility; a secret third thing

Is this just the problem of low agency? Do these people lack the ability to set intentions and follow through on them? No, sometimes they show very high agency and do very impressive things, even while the things they fail at—showing up at the place, at the time—are basic tasks that sound easy by comparison.

Is it just low responsibility? Do these people not feel obligated to follow through / do the thing? Maybe they don’t care about the other party relying on them? No, often they’re genuinely apologetic about missing their cue and look for ways to rectify it.

Locus of control

An old concept in psychology is helpful here: locus of control. That refers to a person’s belief about the causes of their own successes and failures. In the 1960s Julian Rotter found, through experiments and surveys, that people who believe they control their own outcomes (internal locus) are more successful and resilient than people who attribute outcomes to external forces like luck or other people (external locus).

But wait, maybe it’s all because of circumstances. Perhaps some people are blessed to have more controllable lives, so naturally they believe they are in control, while other people have objectively less control and therefore believe so. I can only counter that interpretation with personal experience—I see both types of people in the same socioeconomic status class (~my own).

To me, this says that the internal-locus-of-control people are correct in their belief (they do have control!) and the external-locus people are basically incorrect. The number of things that are objectively, physically within your control—able to be affected by your mind through your body in the physical world—is huge. If the only thing keeping you from exercising this control is the fact that you don’t believe you have it… that’s an unstable equilibrium. It’s a just-snap-out-of-it kind of situation. Stop believing you have no control, and suddenly you have it.

So, I find it misleading to call this thing the “internal/external locus of control,” as if it’s two equally valid ways of looking at things. The primary question about control should not be, “How do you feel about it?” but rather, “Do you have it or not?”

Apparently about half of us have it.

Indirect control

“Ok so we’re talking about self-control, right? Like when you use the rational/planning part of your mind to overcome the urges of the base/instinct part of your mind? Like in the marshmallow test?” No, not quite.

It’s trickier than that because a low-control life often manifests in ways that aren’t directly related to the person’s behavior: My car broke down; My phone fell in the water; I have a headache today; I got sick on my trip; I got swamped with work; I don’t have internet because the tree guy cut down the tree; etc. Who could deny that these are external circumstances, having nothing to do with the person themself?

I could. I’m denying it.

All of it seems external, yet it clearly varies from person to person, even when. One guy will have an unexpected disaster every weekend, while another has never missed a flight or train in his life.

The jettatore

The link between a person’s inner self and the external disruptions in their life is so counterintuitive, some traditional cultures believed the cause was supernatural.

I was listening to this book Diversions in Sicily when I came to this passage on Sicilian superstition:

The day before the festa there came a professor of pedagogy, and Peppino was not best pleased to see him because he knew him as a jettatore. I had supposed this word to mean a person with the evil eye who causes misfortunes to others, but he used it in the sense of one who causes misfortunes to himself or, at least, who is always in trouble—a man who is constitutionally unfortunate, the sort of man with whom Napoleon would have nothing to do. He will miss his train more often than not; if he has to attend a funeral it will be when he has a cold in his head, and all his white pocket-handkerchiefs will be at the wash, so that he must use a coloured one; he will attempt to take his medicine in the dark, thereby swallowing the liniment by mistake. Of course, this kind of man is incidentally disastrous to others as well as to himself and is, therefore, also a jettatore in the other sense, so that Napoleon was quite right.

…The prevailing idea seems to be that an evil influence proceeds from the eye of the jettatore who is not necessarily a bad person, at least he need not be desirous of hurting any one. The misfortunes that follow wherever he goes may be averted by the interposition of some attractive object whereby the glance from his eye is arrested, and either the misfortune does not happen at all, or the force of the evil influence is expended elsewhere. Therefore, it is as well always to carry some charm against the evil eye.

—Diversions in Sicily, chapter 4

It’s not them, it’s you

Is there a supernatural evil force emanating from your eyeballs? “I don’t think so.” Then why would everyone anticipate misfortune around you personally? It must be something you’re doing, even though all those misfortunes are “out of your control.”

External-seeming events do depend on personality, more than is evident, because there’s always the matter of 1) Does the person regularly anticipate disruptive circumstances? Do they predict the easily predictable ones and plan around them? And 2) How do they respond to these disruptive circumstances? Do they find ways to reduce the effect? Can they think outside the box to do so? Will they make a sacrifice in some other area so their plans can continue smoothly?

Why do I have low control?

What I mentioned earlier was basically limiting beliefs: “I don’t have control because I believe I don’t have control.” That’s an explanation, but not a very thorough one. How does one come to hold that limiting belief in the first place, and why does one never update it?

One thing to consider: Do you like having low control? Is it fun? Roller coasters are a lot of fun. Gambling is fun. A low-control lifestyle is often fun! Sure, you’re not happy immediately when the setback happens. But then you must (/get to?) climb out of it. “I missed my train and I need to get to Boston tonight!” Oh boy, an adventure! There’ll be conflict and struggle; you’ll be resourceful; you’ll ask for help; the elevated cortisol will make you feel caffeinated; you’ll do what’s necessary; you’ll accept the costs; you’ll emerge victorious. And the high you feel when you finally secure a ride to Boston will be better than anything you would’ve felt on the train ride you planned to take. Consider this! And consider that your subconscious already knows it, from experience.

Of course, half the time you won’t get that high, you’ll just fail. It’s a lot like gambling addiction in that way: making a profit is unlikely, but the drama is guaranteed, and it’s the drama you’re addicted to.

How do I increase control?

In light of the previous section, my first answer is want it. Do you want to have more control over your life, so people see you as reliable and so you can make plans that bring about a better future? Are you willing give up the emotional roller coaster that a low-control life provides you?

Then, let’s look at the practical stuff. I can think of tips in a few different categories:

Technology

We live in a very techy world. A big part of the high-control life is 1) preventing technology from failing when you need it. But also 2) using technology to anticipate or remedy all kinds of other failures.

• The Waze app tells you where the car accidents and police are—avoid unplanned delays. Also, obviously, you can budget extra time in your trip. The boring solutions are the most effective.

• The line for buying tickets is too long and it’s gonna make you late—buy them online on your phone. Ideally buy them beforehand. Do as much online beforehand as you can: fewer variables the day of.

• Drugs: you can have sleep drugs, awake drugs, painkiller drugs, stomach drugs, etc. Keep them on you, so whatever happens you can at least feel “normal” for a few hours if you need to. You feel a fever coming on but you’re supposed to give a talk at a conference? Delay it for a day with Ibuprofen or whatever; fight the virus on your own terms. Mostly drugs set you up to feel even worse at some later time, and that’s fine. The point is you’re able when your plans require you to be able, and you can crash and recover when the plans are finished.

• You can download Google Maps for offline use. Now when you get lost on your travel adventure, even with no internet service, you still have a really good map and a GPS.

• Related: download the Google Translate language pack for wherever you’re going, so you can easily ask anyone for help.

• I don’t usually recommend specific tools/system for productivity, but obviously if you use a calendar that you can access from your phone, you’ll never double-book something or cram too much into a week. “Oh sorry I have to cancel our thing, I didn’t realize I had [event] that week.” This is a fully solved problem. Google knew you had the event that week; it could’ve told you, had you asked. Half the battle of making good plans is just knowing what you’re already committed to. Did your plan fail because it was something you never had the option to do in the first place? Among my friends and family I’m known for responding to an invitation right away. “Do you want to go to Puerto Rico in the second week of May?” “Lemme check my calendar… yep.” And that yep is final—I will be on the trip; that week is now booked.

  • Aside: Sometimes people in my life are so charmed by the fact that I remembered to “follow up about that thing” for them or “send them a copy” of a thing. And I’m thinking, *shrug* I wrote it down as a to-do item as soon as you told me about it. The moment you spoke it, it became digital information, backed up to the cloud, on an app that I look at every day—it would be impossible for me to “forget” it.

Mindset

I could list a thousand examples of ways to anticipate and mitigate this or that disruption—he knows how to put his spare tire on; she brought an emergency change of clothes—but memorizing examples is not what gives you a high-control life. It requires an attitude shift. Recognize that there’s much more in your control than you thought, if you’re willing to think outside the box. Play a game with yourself: “Assuming this plan fails, how did it fail? And what could I have done to fix it?” Iterate on that several times. Really try to make it fail in creative but plausible ways, and then plan for those. There is so much you can do.

Also, take a note from the imaginary old-timer with a grey mustache who says, “A man’s only as good as his word.” It’s very useful, and considerate, to make “keeping your word” something big and meaningful in your mind. Because maybe there’s no emergency, you’re just having a great time at the current thing and don’t want to drag yourself away to meet an obligation at the next thing. Or maybe you’re feeling tired for whatever reason and it’s just hard to get going. If you value your verbal commitments as something special, that’ll motivate you to go and execute. And if you execute, that’s a costly signal to your subconscious that “your word” is something real that causes real action. And so the motivation gets even stronger, and so on. I’ll end this point here, but it’s worth a more thorough post in the future.

Your environment

Keep track of what conditions are likely to throw you off from feeling good and healthy, e.g. not enough sleep; too much drinking the day before; eating certain foods; an injury from exercise. Then avoid these risks leading up to the period when you need to be in top shape. A lot of high-control is just thinking ahead.

Then look at the environment beyond your immediate person. Do you maintain things? Does your car work reliably? Are you in good standing at work? Are you in a relationship that’s volatile and could blow up at any minute? Do you have a friend who guilts you into doing ridiculous favors? How many ticking time bombs are you sitting on at any given moment? Because, the next time one blows up, that’ll be a typical control failure; you’ll have to cancel the date, the meeting, the trip, to deal with the fallout of the thing blowing up. And when that happens, failing to show up will be the least of your worries, because you’ll be in emergency/hero mode. And “you could have prevented this” will be the last thing you want to hear. So hear it now instead.

Regrets, I’ve had a few
But then again, too few to mention
I did what I had to do
And saw it through without exemption
I planned each charted course
Each careful step along the byway
And more, much more than this
I did it my way

In recent years, a few public figures have risen to popularity mostly by reminding us that personal responsibility exists. Many people, when they hear that message, find it to be a key that unlocks a lot of life satisfaction. Why the sudden change? Where does all the motivation and positivity actually come from?

You, and only you, are ultimately responsible for how happy you are.

—Rachel Hollis

Responsibility is not agency

Someone whose life is in a depressing rut hears the message “Clean your room, save your money, and work on your relationships,” and they change. On the surface, it looks like they’ve suddenly been injected with high agency, because it matches the pattern of “people shaking up their old routines and doing bold new things.” But responsibility is not the same thing as agency, because responsibility is fundamentally about blame and credit. It’s about where you point the finger when you’re analyzing what’s going right or wrong in a situation. A person with a strong sense of responsibility believes that they alone are “on the hook” for improving things (in their personal life, their profession, or whatever domain they’ve accepted responsibility for).

A high-agency person will try grand ambitious things, but they won’t necessarily accept the blame if they fail. A high-responsibility person will always take accountability for failure, but they don’t necessarily try grand ambitious things. They might be content with a quiet, routine life that they take full responsibility for maintaining.

Responsibility may cause agency

However, responsibility does seem to often go together with agency. It can act as a catalyst for big life changes. If you feel a strong sense of obligation over a particular outcome, you might be forced to think outside the box, looking at all your options to make it turn out right. People tend to work harder and more tenaciously when they have someone or something to take care of. If everything is chaos at work but you feel responsible for this product shipping on time, you’ll figure out a way to get it done. If your family is hungry, you’ll figure out a way to get money. High-agency actions can be powered by a sense of responsibility, which is a beautiful thing that our culture loves to celebrate.

Again, though, responsibility is a moral reality. It requires a moral framework—some sense in which “I’m not right with myself/God/the universe if I don’t try my absolute hardest to handle this situation.” And agency, by contrast, is amoral: with high agency you can help or harm, or do neither. It’s just a part of game theory; it can be noticed and examined without any moral framework.

How do I increase responsibility?

To have responsibility, you need to have some moral framework in which people in certain roles are obligated to respond to certain situations. Jordan Peterson got popular preaching an ethic of personal responsibility that’s rooted in a somewhat vague “Western traditional” moral framework, which a wide variety of listeners could accept. Maybe that’s your thing. Maybe it’s Catholicism, or humanism, or social justice, etc.

But the moral system needs to confer obligations. If you already subscribe to a moral code that doesn’t put a lot of personal responsibility onto you, you’re kind of stuck. Can a person change their own moral code? If you could change it at will, then isn’t the reason you changed it your real moral code, since that’s what you’re using to direct the arc of your life? These are big, difficult questions.

I don’t have an easy answer for how to increase personal responsibility from scratch, except perhaps to try listening to people who “preach” in that vein, and see if they resonate with you. It may be the case that your own moral system already compels you to be more responsible, and you just needed a “prophet,” like the Hebrew prophets of the Old Testament, to bluntly call you out for falling short.

Or, alternatively, you could go action-first: put yourself in situations where responsibility is commonly expected, and watch yourself rise to the occasion.

He saw the Lusitania in distress (What’d he do?)
He put the Lusitania on his chest (Big chest!)
Drank all the water in the sea
And he walked all the way to Italy

The first one we’ll cover here is agency.

Agency: the “main character” trait

In game theory, an “agent” is a thing that can have intentions and make decisions.

Who has it?

“Do AI models like ChatGPT have agency?” is a popular question nowadays. Currently most people in my bubble still answer no, but the line has been getting blurry. AI technology is a useful example to start with, because even though we know ChatGPT is just software that does text completion, it seems very human most of the time. In many cases when you talk to ChatGPT the experience is just like talking to a human.

That brings us to: “Do humans have agency?” Classically the answer is “Of course, yes,” but if you look closely you might notice that much of the time we, too, are just doing something like “text completion.” At our jobs and even in many casual social interactions, we’re often following an implicit script—playing a well defined role the way ChatGPT does. Do you ever say “sorry” when you’re really thinking “You’re wrong”? Do you say “Sure that’s fine” when it’s not, just for the sake of social ease? Aside from text completion, think of action completion: do you follow through on a behavior just because it’s the thing to do? Keep showing up to a job you dislike? Keep living in a town that bores you?

Yet, at other times, humans do wildly agentic things like quit their comfortable jobs, or move to another country, or solve a unique problem. In those cases we appear to be acting out of free will, though that’s a fuzzy concept that’s hard to define. We could at least say that we’re acting on some very deep intention, and maybe we don’t fully understand the source of it ourselves, but we’re fiddling with all the levers available to us in our lives to change our world in a specific way.

Variable agency

So, in different situations people can behave with high or low agency. But you’ll also notice that some people just seem to display high agency more often than others. I have a friend who’s very connected socially—he has a big network of friends and acquaintances—and a hobby of his is getting into events/parties that he really has no business being in. He’s charismatic enough to just show up and make friends. One day he told me he’d written and self-published a children’s book over the past week, because he just wanted to. That’s a pattern of high agency.

I knew a woman who was a social media influencer—with no 9-to-5 job, she made all her income from brand endorsement partnerships. When I last talked to her, she was working on a screenplay about her life experiences—and I mean really working on it, she’d already hired people to help her develop it. She had plans to partner with a chef she knew to develop and market her own brand of salsa. Who knew you could do that? That, again, is a pattern of high agency.

How much do I need?

It’s popular to describe high agency as “Main Character Energy,” referring to the fact that the main character in a story is the person who does interesting things and has unusual experiences.

From this perspective it seems like agency is an absolutely good thing to have. I’m not sure though—there are probably times when it’s better to be able to settle in and go on autopilot for a while. Some situations are out of your control and the best course it just to get through them without freaking out. Maybe, in those situations, trying to have high agency would make you depressed when confronted by your boundedness.

So perhaps it’s a balance. But, you are living in the 21st Century modern world and most of the time the choices before you are innumerable. It’s very hard to really get stuck in a rut: I see people with far fewer opportunities than me do far more agentic things all the time.

I once wrote on consumption and productivity and claimed the modern world is always skewing us toward consumption, away from the happy balance between the two. Likewise I think the modern world is always skewing us on the script-following-vs-agency spectrum. It’s just so easy to fall into a decent and well tested lifestyle script, despite all the opportunities that exist if you look for them. If you agree, then you’ll want to intentionally increase your agency, to counteract the influence of modern life.

How do I become more agentic?

The easy shortcut answer to “How do I become more __?” is always: Spend more time with people who already have that trait. There’s no need to deconstruct what the trait is or where it comes from; just utilize the power of social influence to shape your character the way you want to.

As a substitute, you could read a lot of writing by people with that trait. When I read writings about high agency, like Things you’re allowed to do, I immediately feel more agentic.

Second, you could focus on avoiding the factors that reduce your natural human agency. That’d be things like addictions and other “scripts” you follow or “ruts” you get stuck in. For example, “Every time I go out with these friends on Friday night, I drink too much and am knocked out on Saturday.” Then, you could invest a little willpower in changing that pattern, and you’d end up with more agency on your Saturdays.

The vast world of agency blog literature

So much has already been written on agency, so I want to end here and let this be a jumping-off point into some of the related content that I’ve found helpful over the years:

• How to be more agentic – Cate Hall; a very detailed and practical guide

• Thoughts on agency – Henrik Karlsson; a direct response to the above, adding some nuance

• Looking away from a car crash – Egg Report; a focus on avoiding the “ruts” that absorb your attention and make you miss opportunities

• Rest in motion – Nate Soares; an interesting shift in how we relate to “work” and “rest” in our lives

• Why execution (not ideas) will bring you success – inc.com; dated, but an important idea to internalize

• The top idea in your mind – Paul Graham; even more dated, but relevant as ever; a warning about spending your attention and creativity on goals that aren’t worth it.

Is it you?
Is it you who’s been orchestrated?
Is it you?
Is it you who’s born frustrated?

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I can kind of rationalize how this works. It’s the underdog narrative. We love a good underdog story, and in practice some people cannot find the motivation to try hard unless they see themselves as disadvantaged in some way.

The hero’s journey

The rise of the underdog is such a common trope that we mostly take it for granted. The hero’s journey, the essential narrative template of Western (and a lot of non-Western) literature, is an underdog story—if you focus on the “challenges → abyss → death & rebirth” part.

The hero’s journey is so baked into our culture through our popular works of fiction that it can be hard to imagine a compelling story without it. Is that because it’s really the perfect formula to make a story resonate with human minds? Or is it arbitrary—we like the hero’s journey because we were raised on those stories and they shaped our ideas of what makes a good story? It doesn’t matter; this post is not about figuring out literature, but about being productive in real life.

What works in a compelling heroic fiction is not necessarily what works in real life. Imagine a story where the hero is able to meticulously prepare for the big battle, fixing all the circumstances to be in his favor, planning for every contingency, and then the battle happens and it’s not even all that challenging. Not a great story! But he wins. Those who are addicted to imperfect conditions need to ask themselves, “Am I trying to create a compelling narrative where the hero overcomes daunting odds, or am I trying to win?”

The heroic fiction often depicts all the planning and training steps as a montage. It does this because it’s boring otherwise. But in real life most of the winning is in preparation—the repetitive drudgery that creates the ideal conditions for success.

Then later, the heroic fiction throws a wrench into the hero’s plan at the last minute, because that creates drama. Do you want drama, or do you want to win? Become comfortable with the fact that most wins do not look like popular heroic fiction.

Self-sabotage

Those who can only find motivation when they’re the underdog will sometimes make themselves the underdog, just to be able to enjoy the pursuit of greatness. They’ll throw the wrench into their own training/plan/effort, because they experience that as a relieving of pressure.

It doesn’t need to be as on-the-nose as a drug binge. It could be failing to get enough sleep while you’re training, or failing to rest an injury, or refusing to think about and plan for a future goal. Then when the moment of opportunity comes, the deck is all stacked against you, and you try to make up for it with raw white-knuckled effort.

When you self-sabotage, the only two possible outcomes are that you win—and you do it in a “heroic” (underdog) way—, or you lose in a way that “makes sense” and leaves open the possibility that you could’ve won, so you don’t risk hurting your ego. All of this is a twisted mind game that feels necessary from the inside but looks very silly from the outside.

Outcome rewards

The antidote to being addicted to perfect conditions was to reward the effort, not the outcome. Conversely, the antidote to being addicted to imperfect conditions is to base your reward more on the outcomes! Fix your attention on the end result of your efforts: the sum of all your preparation and planning and self-maintenance and your final in-the-moment heroic effort.

(Same as in the last post: A “reward” could just be an internal feeling of satisfaction, or it could be something tangible you do for yourself.)

Shifting the reward structure to outcomes will motivate you to add the boring preparatory work to your heroic effort, because you need both to maximize your chance of getting a successful outcome.

Does effort suck?

Isn’t it funny how we play these games with ourselves? Needing perfect conditions to make the effort “worth it,” or needing imperfect conditions to make the effort “necessary?” I wonder, is it just that effort sucks, and we’ll use whatever excuse we can to avoid it most of the time?

But if you’ve ever been in a “flow state” or had a goal that you completely loved and could fully commit to, you know that it can be joyful to expend high effort, even day-after-day-after-day. And a lot of specific “productivity advice,” like this post, is just not necessary when you deeply love the work you’re doing. It’s for the rest of the time, when you have work that is boring but necessary in life, or that you only partially like, or that will set you up for some later life stage where you’ll thrive. Generalists are particularly likely to have projects like this—coasting in one habit while investing heavily in another; feeling their passions shift around over time. The right amount of structure and “productivity advice” gives you control over all this, so you don’t end up wasting effort on all the task-switching.

Related: here’s my growing list of Generalist productivity skills.

Narrative permission to slack off

I started lifting weights in college and continued through most of the years since college. I also trained Parkour on and off throughout that time. During covid I did calisthenics/resistance band workouts. Those were all self-directed fitness activities.

Putting effort into a self-directed plan can be tricky—when you’re the Manager of your own program, you consider things like like how fatigued you feel, how tight or sore your muscles feel, or how busy you are elsewhere in life. “I can’t go too hard today because __.” Maybe it’s “I didn’t get a lot of sleep last night,” or “I’m traveling soon, so I have to be careful not to get hurt,” or “My mind is preoccupied by this other thing I have to do today.”

My body’s natural response to those thoughts is to give less effort. On those days, I don’t set personal records in my lifts, maybe I skip an exercise at the end, etc. And it’s not necessarily a conscious decision—just noticing that the conditions aren’t the best at a given moment has an effect on my mind and body. Once there’s a “reason” for underperforming, a narrative explanation for it, then my body will take the opportunity to underperform.

(Some people do the opposite: they tend to give high effort only when there’s some special obstacle to overcome, and they see perfect conditions as chance to relax their effort. More on that in the next post.)

This doesn’t mean I never try hard—I’m proud to say I’ve made measurable progress in physical fitness over the years just planning and executing programs by myself. But still, the above is always a factor I’ve had to contend with.

Hiring an outside Manager

When I started training Muay Thai kickboxing two years ago, I went in with the intention to do a lot of training right away, rushing toward save points to make my training more effective. So, I was doing a lot of training.

And at my gym, like most martial arts gyms, we train in guided group classes. It’s not self-directed like the stuff was doing before that, or the solo running/biking/calisthenics that so many other people do for their physical fitness. The special thing about guided training is that the expectations placed on your effort are detached from your internal state: assuming you respect the teacher/coach (and I do), you’ll put as much effort into the class regardless of how you feel.

That’s simply because the coach doesn’t know your internal state. They expect the same effort regardless. It’s a bit like when a company hires an outside consultant, who is ignorant of the company’s internal culture and processes: that’s on purpose, so they can tell hard truths and call for high performance without being biased by the status quo.

I see now why people get so much benefit from using a personal trainer, even if they could easily plan out the exact same workout routine for themselves. It’s the separation of circumstances and expectations. In the corporate world, if your manager is working at the desk right next to yours, you can, for lack of a better term, invite them to micromanage. “Hey I know you assigned me this task, but this one complication just came up. Do you think we should change the deadline, or should I do XYZ to address the complication?” And then your manager will answer, and… this just isn’t isn’t a good use of their time, and it conditions you to look for little reasons to delay the actual work. Alternatively, if your manager is behind a closed door at the end of the hall, you’ll more likely just do the work and deliver the best result you can.

No factor

I’ve learned something about my capability in these kickboxing classes. I’ve shown up to class sleep-deprived, or hungover, or bloated, or hungry, or upset about something, and I notice I perform at about the same level every time. Or, if there’s variation in my performance, it’s not very correlated with those other things.

(Disclaimer: of course any one of those factors would be a problem if it happened regularly—you shouldn’t be sleep deprived! etc.—but as one-off issues that just come up in the randomness of life, they… don’t matter like I thought they would.)

One time I went to the 7:30am class on 3 hours of sleep after celebrating Halloween drinking all night with my friends, and to my surprise the class went the same as always. Your body will give you as much adrenaline as you need to perform to the level required, as long as you actually require it. Of course, your future self pays the bill for that: I felt totally exhausted later in the day. But that, too, was perfectly bearable in the context of an otherwise normal, healthy week.

Behavioral rewards

I realized that in the past I’ve been addicted to perfect conditions. I needed to be at 100% readiness to give 100% effort. I think the rationale for that was something like: If you only give max effort when the conditions are great, then your outcome/performance is pretty much guaranteed to be great in those cases, and you’ll set personal records or whatever. So your max-effort is always associated with real measurable wins, and so you get that behavioral reward for it.

It takes a different mindset to be able to give max effort and accept that some other factor might end up hurting your performance. Again, I learned from experience that effort matters more than I thought, and other circumstances matter less, so that alone changed my mindset a lot.

What also helps is rewarding the process. If I give max effort, I should reap some kind of reward—it may just be a mental feeling of satisfaction, or it may be something tangible. But if I attach the reward to giving maximum effort rather than getting measurable success in my performance, then I’ll be conditioned to give max effort a lot more often. By default, rewarding outcomes is more comfortable for me, because then the outcome is guaranteed, but the downside is I may end up cutting corners on the day-to-day process. This is the constant dance between goals and systems—I think only experience can help you find the best balance.

This will fix all of your organizational problems. I mean every time you have to “dig something up” and it takes more than 10 seconds; every time you “could’ve sworn I wrote this down somewhere”; every time you have 13 documents with titles like draft_final_2.docx.

All of this should be easy. For all the work you do to create and collect valuable information—notes, documents, bookmarks, folders—it should be immediately available to you whenever you need it. Some people are naturally organized and some aren’t; let me try and help those who aren’t, because the whole thing can really be made so simple.

Why is organization a big deal?

Generalists who juggle multiple projects often need to stop-and-go on them at different times. I’ll often start something, progress to a decent milestone, and then put it on hold to get into something more opportune. Months or years could go by before I return to it. But I do return to it, and I do finish it, and the context-switching costs are not bad. The only reason I can pull this off is because I’m careful about organizing and documenting my ideas, knowledge, and work.

In my closet right now I have an unfinished painting that I started in 2018. I still like the project, I just haven’t had a strong enough reason to dedicate more time to it over other things (gradually I’ve been completing other art projects that were more important to me). Now it’s the end of 2024 and I still know exactly where to find the info I need to continue that painting (the reference images, plus my notes on what ideas the painting should evoke).

This a superpower—to be able to kick a project far into the future and still retain all the progress you’ve made. It makes you more agile in the present, able to quickly shift your focus when good opportunities come up. So ironically, this strict focus on good organization allows you to throw your structured plans to the side and act on your gut more often: the structure will be there waiting for you, unharmed by your temporary neglect.

And good organization is easy. There are only two rules.

Name things correctly

Give everything a name that your future self will understand.

Don’t write words that are ticking time bombs to being incorrect. If you name a document Next month's newsletter.docx, that will be the correct name for one month at most, and the incorrect name for the rest of eternity. One day you’ll open Next month's newsletter.docx, and it will not in fact contain the newsletter for the next month. The name is a ticking time bomb: safe for one month, but after that it’s lying to you.

To name things correctly, always ask, “Which?”

Simon Sinek agrees

You’re tired of writing and you decide to save this new document as draft.docx. Well, which draft is it? “The draft of my newsletter.”

newsletter-draft.docx

Which newsletter is it? “The one I’m sending out in January.”

january-newsletter-draft.docx

Which January is it?

january-2025-newsletter-draft.docx

That name, or any name that has basically the same information, is a correct name. And a lot of this is covered if you have a good hierarchical folder structure (but you don’t have to). For example, the draft could live in a Documents/newsletters/2025/ folder and then simply be called january-draft.docx. Consider the location to be part of the name (techy people will know that it literally is).

In any case, by clarifying all of the “which”s, you eliminate all the misunderstandings your future self could make.

Go easy on your future self! We have a tendency to think our present context and all of our short-term memory will carry forward perfectly into the future. “Of course I’ll know what I meant here, I’ve been working on this all day.” But I’ve done this to myself enough times to know it doesn’t work like that.

Don’t make two of the same thing

This spins off from the first rule: if you name things correctly, it’s much easier to check if something already exists. But if you don’t, or if you work with different organizational schemes, or on different platforms, it’s very easy to end up with two of the same kind of thing.

You thought of something you want to add to the newsletter draft, but suddenly you find yourself with both a newsletter drafts.docx and a next-newsletter.docx…

Every time you go to create a new file/sheet/folder/whatever, you have to ask yourself, “Does the thing I want to use this for already exist?” It’s a tiny habit that will save you so much time.

This also means you have to sync some stuff across your devices or platforms, ideally automatically. You have an art projects folder, but it’s on your home computer, and right now you have an art idea you want to write down, but you’re away from your computer, so you write it in a note on your phone. Now you have two of same thing: “place where my art project ideas go,” and your future self isn’t going to like that.

Clean up your Google Drive / OneDrive / Apple-whatever and make sure it’s syncing across all the devices you use. In order to have only one of each thing, that thing needs to be available to you in all the contexts where you might access it.

By following this rule, you’ll always put things where they “belong.” You met a nice person and just learned their birthday, and you want to remember it. You write it down in your phone notes. Is that the place where you’re tracking birthdays? Because, Apple Contacts or Google Contacts (whichever is storing phone numbers for you) has already laid a claim on where birthdays belong. They have your friend’s phone number associated with their contact, and they’re just as ready to store the birthday. Don’t let yourself have two different places where birthdays could be found.

I used to have a temp stuff folder, for anything I’m going to use immediately, when I just need to put it off to the side for a second. It’s a useful folder! But then I realized that most of the time my “temporary stuff” is files that I just downloaded, so they’re starting in the Downloads folder. So now I just use Downloads as my “temp stuff” folder: I’ll move files into there when I need to put them somewhere temporarily. So there’s exactly one place where that kind of stuff goes.

You do you

I’m not going to tell you where to write notes or which to-do app is good or whether you should use a calendar for anything, etc. Everyone has their own preferences for what they write down or save and what kinds of systems they use to organize their thoughts/knowledge/projects/lives.

Maybe you hate to-do apps but you write daily goals in a plain text file. Maybe you keep a journal but you only write about your feelings, nothing else. Maybe your reading notes are all squeezed into the margins of the physical books you read. It doesn’t matter—whatever system works best for you, you can do it justice by following it well, and that entails: naming things correctly, and not making two of the same thing.

Happy organizing!

At face value, this is undeniably good for you: mainly because it means you’re getting more exercise than the average person (and the average person isn’t getting enough), but also because it’s good to subject your body to some variety of challenges. But fitness generalism can be difficult, and not just because you’re working out extra.

Fitness whiplash

Generalists who bring their multiple interests to the world of physical fitness quickly learn that there’s no such thing as “fitness.” There’s fitness for sprinting, fitness for playing basketball, fitness for rock climbing, and so on. Getting fit for distance running will hurt your fitness for heavy lifting. Getting larger muscles will help your fitness for heavy lifting, but only to a point, and if you really care about heavy lifting you’ll eventually have to change your program from “mainly hypertrophy-focused” to “mainly strength-focused.”

Fitness generalists will likely want to change up their fitness routines often. And, that’s a bit of a pain, because it’s essentially forcing your body to work against its past self. This month is running; next month is volleyball; etc. In all the back-and-forth whiplash of fitness adaptations, you may be preventing your body from making real progress in any one area. After all, physical fitness happens on the scale of seasons and years, which is often slower than the rate at which a generalist finds new interests.

Buying moves

Fortunately, there’s an amazing quirk of the human body that makes fitness adaptations work a bit like powerups in a video game. You can spend some resource to add capabilities to your “character,” and if you do it right they’re always available to you (for the most part). I’m talking about muscle memory and our ability to “lock in” physical skills.

If you play volleyball for three years and then quit and lift weights for the next three years, you don’t lose all of your volleyball skill. You don’t even lose most of it. It’s really convenient that our bodies work this way—convenient for generalists especially! You buy moves with time and effort; you have to put in enough hours of practice to get to a “save point” where you learn the skill in your body and not just in your mind. Then it’s “locked in” for a long time.

Sometimes you quit before you get to a save point, and that’s okay. I’ve “learned” swing dancing at least three times in my life. I never got to a save point—meaning, in the present moment I can’t do any proper swing dancing. I learned enough to know something for one night or one week, but not enough to lock in anything to muscle memory. Was my time wasted? Well no, it was fun. But you can see how it’d pay off a little more if I practiced for, say, two weeks straight. Even if that was 10 years ago, I’d probably still remember something of swing dancing today.

Different activities have different save points. Shooting a basketball with proper form for a decent percentage takes many, many hours of practice—longer than, say, learning how to slowly ski down a moderate hill. A generalist benefits from thinking about these things ahead of time: “How frequently am I willing to practice this thing, and for how long, and what skills do I expect to lock in over that period of time?”

Personal experience

I’ve saved skills into muscle memory (“bought moves”) in several areas. I can do the parkour vaults; I can shoot a basketball; I can vertical-jump with proper form and get pretty high, etc.

The other day I played basketball for the first time in like seven years. It felt rusty, sure, but at every point in the game my body at least knew what it was supposed to be doing. There was no uncertainty in it, just rust in the execution. In other words, all the memory is still there. If I’d practiced for just a few days straight, moving in the right ways and pushing my cardio, it would’ve gotten me to ~90% of my previous skill level.

And it’s a nice feeling to know that I could return to that. Nothing in life is permanent, and certainly nothing about our physical bodies is permanent, but the way our muscle memory works feels just a little bit like permanence.

When I started Muay Thai kickboxing, I only intended to learn some basic self-defense over the course of two or three months (I ended up loving it and continuing it, but that wasn’t planned). I went to four class sessions in my first week. I soon upped it to five per week, and then six. I put myself on a crash course because I wanted to lock in something permanent, quickly. I’ve seen beginners come to my gym intermittently for six+ months and still not get to the level I reached in those first three. They’d be better off not going to the gym for all that time and then cramming all their lessons into a shorter, more focused block of time. These are the kinds of advantages you notice if you think ahead in terms of buying moves.

The big picture of fitness

What is the fitness generalist’s overarching goal? I do think they should have one, as opposed to just dabbling in whatever sport or activity feels fresh. With aimless dabbling, you risk missing the save points and making your body work against itself.

A fitness meta-goal could be something like “be more generally adaptable to a variety of physical demands,” or “be able to play a lot of different sports with friends.” The most important goals in life are fuzzily defined anyway. But if you think about save points and buying moves, then everything you do in fitness is potentially something you can keep with you for the rest of your active years. Paying mind to the big picture lets you make physical fitness a unified life project, even while you enjoy great variety in your physical activity.

You’re stressed out for some reason, so you take the evening off for a YouTube binge. You end up staying awake a little later than usual and sleeping poorly. So the next morning you feel especially tired; you snooze a few extra times. In your rushed morning routine you don’t have time to prepare for the work meeting as much as you’d planned to. So you have little to contribute during the meeting. You feel bad about your performance. You escape from the bad feelings with a Twitter break. But Twitter is freaking out. Elon Musk said what? Everyone is weighing in. This is going to occupy you intermittently for the rest of the day. And so on.

Laziness has a kind of independent momentum to it. When you’re having a day like the above, even if you consciously commit to getting back on track, the rut tends to find its way back to you within a couple of hours. Keep this up for a few days and your sleep is utterly messed up, and you walk around in a fog. Keep it up for a week or two and you’re fully off your workout routine. In a month or two, you might have noticeably fallen behind on work; you might be absent from your social life; you might’ve visibly gained fat or lost muscle; you can no longer feel excited about your personal goals because they’re behind a pile of mundane tasks you need to catch up on first. And so on.

How do we stop the vicious circle?

I’m spiraling! I’m spiraling!

When you’re in a laziness death spiral, it’s hard to do anything deliberate. The first and most important step, which does take some willpower but not a lot, is to acknowledge, “I’m in a laziness death spiral today.”

If you don’t acknowledge it, here’s what happens: You vaguely notice you you’ve been wasting time today; you feel a twinge of guilt, so you quickly decide, “I’m going to turn the rest of the day around, starting right now.” And does that work?

Often it doesn’t! Sure, after a small lapse you can just get back on track, but if enough laziness momentum has built up, a momentary reaction doesn’t cut it. Deciding things quickly, in response to negative emotions, is exactly how you got into this situation! You’re going to turn it around on a whim? You’ll have a different whim in the next hour; what then? You need to take a step back and get your mind outside of the problem.

Do what you can

The next three sections are three different courses of action you can take to get out of a laziness death spiral. One of them is clearly preferable, but I’m writing the alternatives, too. When you’re in a low-willpower state, it’s often bad to attempt the very best solution—the farther you reach, the harder you can fall. Building a base of “small wins” is the reliable way to repair your willpower. If you start something lofty and then bail on it, you’re doing real damage: logging another willpower failure and associating that “very best solution” with failure.

Here are the moves:

A) Emergency recovery

If you’re in a laziness spiral and you need to get out of it right now, there are some measures you can take that, while effective, are not ideal. They are unsustainable, promote bad habits, or are just generally unhealthy. But sometimes the need is there: maybe you have a deadline fast approaching (and the deadline itself isn’t enough to snap you into action); maybe your friends or family need you to take care of something today; maybe you were in the middle of an awfully lazy day and a once-in-a-lifetime opportunity came up, and you just can’t focus enough to act on it.

Disclaimer: I believe that in a well planned life, none of these should ever be necessary. I’m only writing them because we are not perfect.

• Motivational videos: It’s a whole genre of YouTube/Instagram content. They make tons of this stuff. The male-coded ones have clips of men lifting weights and climbing mountains set to audio of David Goggins or CT Fletcher yelling at you to get to work. The female-coded ones, I’m led to believe, feature beautiful and confident women giving positive affirmations. These videos do work; they inspire a certain emotional state in their target audience, and that state provides the mental energy to take immediate action. The downside is that you naturally build up a tolerance to emotional triggers over time; you can’t watch the same video every day before your workout and expect it to feel the same. The other downside is that they might not even last very long. Your emotional state will change again, maybe sooner than you think.

• Music: Listen to the songs that you associate with action. Similarly, this inspires an emotional state. I find that here, too, the effect is short-lived, unless I keep the playlist going (and sometimes you can’t have music playing while focusing on the work you need to do).

• Drugs: Ingest enough caffeine to change your headspace. Or take Adderall or some variant. Don’t listen to me, I don’t know anything about drugs. Obviously you’ll build up a tolerance over time and obviously it’s very bad to depend on a substance to perform.

B) Natural recovery

What’s the easiest way to get out of a spiral, without doing anything drastic or unusual? I find there are times when it’s naturally easier to change course. And if you wait for them to come, you can pull yourself out of a spiral without a herculean effort of willpower. Then you can analyze what went wrong and avoid those circumstances in the future.

Wait for a reset point

For me, waking up in the morning is a mental reset; nothing from my headspace the night before really makes it to the morning. Now, bad habits from the night before might’ve given me less sleep, or poor sleep, but I find that my willpower is usually fresh. So when I’m having an off day, and I notice, I might just call the rest of the day a wash and start planning what I’m going to do tomorrow. Even as I’m caught up in lazy activity, I’m making specific plans to be productive tomorrow. The fact that it’s at a later point in time means I’m thinking about it for a while, putting more mental energy into the plan. That’s the opposite of “deciding on a whim.”

It also gives me time to realize, wow, I really don’t enjoy being lazy. In my New-Year’s resolution rant I talked about this effect. For those who continually fail their New Year’s resolutions:

Got a project you’ve been excited about but afraid to start? Don’t even think about it—don’t enjoy the fantasy of it; stop telling your friends about it; pretend you never had that intention in the first place.

In other words, aggressively run away from your goals, and reflect on how miserable it is to live that way. The reflection is crucial: if you’re self-forgetful / not mindful about it, you’ll risk staying in that state. Do it for a week or two, reflect on how much it sucks, and in doing so you’ll condition your mind to view the goal as a valuable opportunity to escape that misery (which it is).

Sometimes you cognitively “want” something, but there’s just no mental energy behind that want. You know some goal or idea is good for you, but you don’t feel, subconsciously and emotionally, that it’s good for you. Sometimes you need to feel it. So, you should go completely without the thing for a while, and allow yourself to feel irritated by that condition.

This is actually a sneaky form of self-control. When you notice you’ve been lazy, your next impulse is to dash into some “productive” task to start “making up for” the lost time. But this reinforces a habit of acting on impulses. In a way, it’s more difficult to remain in the state you’re in and accept the loss. A person who can do that can also wake up the next day and be extremely productive.

What are your natural reset points? Maybe it’s the morning. Maybe it’s when you go to a specific location. Maybe it’s a specific day of the week. Identify your next reset point, and then wait patiently for it to come.

Analyze the circumstances that caused it

The other part of the natural recovery is to notice what started your spiral, so you can avoid it in the future. You do this analysis as soon as you’re at a reset point. Look at your recent activity and ask, “Where did I go off the rails earlier?”

after a chess game, i open the game review, wondering: which move lost me the game? was i winning at any point?

i need life game review at the end of every day. when did my day go awry? was i on pace to have a productive day at any point?

— monk (@mechanical_monk) August 10, 2023

In doing that review, you’ll discover how far back the laziness death spiral goes. “Well it’s cause I got up late today. Why was I on my phone so late last night? Oh yeah, that other thing…”

For me, when I get down to the real original cause, it’s often something very mundane that just happened to occur at the perfect moment to throw me off. A few examples:

• Food: I ate a huge meal and it put me into a food coma that I wasn’t prepared for.

• Media: I watched something a little too attention-grabby, a little too early in the day. On the spectrum from art to entertainment—where the art requires more mental energy to enjoy but delivers richer value, and entertainment can be enjoyed passively but is cheap value—I mostly only slide toward the entertainment side throughout the day. So for example if I play a video game at 6pm, there’s very little chance I’m going to be consuming something thoughtful and complex at 9pm.

• Sleep: This is actually more nuanced than just “I didn’t get enough”: waking up at the wrong point in your sleep cycle makes you feel much groggier. In any case, if I wake up feeling off and I don’t immediately need to be somewhere, I’ll drag it out, snoozing. And that doesn’t make the grogginess go away. And although I may not miss any explicit plans, it puts me on a lazy bent.

• Decision spirals: I don’t necessarily believe in decision fatigue, but there’s a certain kind of decision that’s absolutely devastating for my productivity. It’s when I have to pick between two pretty balanced choices, but there are many little details to consider on each side. The longer you spend thinking about it, the more dynamics reveal themselves. So it’s kind addicting; you hope that if you just view the problem from one more angle, something stark will appear and make the choice easy. But the more time you spend, the more cost you have sunk into it, which makes it feel all the more important that you decide optimally when you finally decide! In short, Choices are bad. 

So, that’s the natural recovery. It works pretty well, but the downside is that you can get knocked off again. You might know the exact circumstantial triggers that caused a spiral last time, but different ones will come up next time. Some you can mitigate, but some will keep coming at you because, as I said, they’re mundane. And that makes me again wonder how something as ordinary as a big meal had such a great effect on my day—perhaps something else is going on.

C) Heroic recovery

The heroic recovery from a laziness spiral is harder and takes longer to work, but it solves the problem in a more complete way. I have enough familiarity with this to see how it works, but not a ton of familiarity. I learn from people more mature than me; every day is a journey.

In short, the heroic recovery means deeply analyzing yourself to understand the root cause of your escapes to lazy pastimes—your decisions to dissociate from what’s going on immediately in front of you.

Deep psych work

Think about the circumstances behind your lapse, like you did in the last section. Then go deeper and analyze exactly why you responded the way you did. Typically, you experienced some minor discomfort, and you escaped from that discomfort by hijacking your attention with a quick-reward activity. What was the minor discomfort? I don’t mean the trigger in physical reality; I mean what was the negative feeling that you cut short? And why?

most things I’ve read on here so far are about a particular self-coercion—”making yourself do things”

when part of you is afraid/upset/overwhelmed/doesn’t-want-to but you push down those feelings to “do it anyway”

seeing now, some ways of “not doing things” are similar

— prerat (@prerationalist) November 18, 2020

Does the feeling go against your self-image in some way?

Some of us can go through decades w/o ever properly coming to terms with our feelings. It is in this sphere that, on reflection, I realized that I actually do know what denial feels like. It’s spookily subtle. “I’m a fun guy” => “that’s not anxiety! Fun guys don’t do anxiety!”

— Visakan Veerasamy (@visakanv) August 5, 2019

What kind of self-image adjustment would it take to be able to accept that feeling? Who would you be, if you were unconflicted about what you felt in any given circumstance?

“When we truly feel comfortable, the desire to improve is natural— no antagonism required, no debt incurred.” – @ChrisLakin_com https://t.co/NQlXA0frXb

— Visakan Veerasamy (@visakanv) January 17, 2022

This kind of work is best done on a good day when you’re already doing the things you want to do. It’s too important to do on a laziness death spiral day, and it can easily become another part of the spiral: If you’re busy analyzing your reaction to some feeling, you’re not feeling it. You’re still avoiding it.

But, if you do enough digging up and sorting things out, you start to re-frame these dissociation triggers, so that even the ones that are out of your control don’t affect you the way they used to.

Conclusion

This has been a very heady post. I notice I’m writing very heavily from personal experience here—more than usual—because the dynamics of willpower and laziness and dissociation are very subjective. If it doesn’t seem to match your experience, then disregard it. But if there’s anyone who experiences laziness the same way I do, I might have saved them a lot of trouble.

I also hope it gets you thinking. One of my favorite questions from the life coaching practice is, “What’s hard about this?” If you ask this simple question of yourself, about whatever you’re currently trying to do, big or small, it can be enough to shake you loose from whatever obstacle or environment is blocking your progress. What’s hard about being a generalist?

Illegible competence

The first struggle is that generalists tend to not get as much feedback or appreciation for their work as specialists do—unless their unique array of skills leads them to discover or invent something uniquely valuable.

Specialists have a straightforward way to create value in society and receive status, money, and fulfillment in return. Generalists don’t have such a clear path. A generalist’s competence is mostly illegible/hidden. They say, “I can connect my experience as a musician with my work as a manager”; “I think I could improve our customer onboarding process, based on some principles I learned in the gym”; and so on. But how do you measure the value of that? It’s much harder than measuring the single-track productivity of specialists.

So generalists are sometimes at risk of being undervalued in the labor market. Consequently they feel pressure to match the specialist’s lifestyle so they can compete in specialist metrics a little better.

(On the other hand, however, having illegible value in the labor market can have advantages, too).

Unclear end goals

It’s increasingly common for people to “have no idea what to do with my life.” The modern world is giving us more lifestyle options than any other people in history had, and generalists are especially likely to consider all those options. There’s a wider variety of companies to work for and a multitude of ways to earn a living online, more places to live in, more people to socialize with, more books to read, more ideas to be inspired by.

It can be daunting to choose between so many possible lives and lifestyles. When you sit down and really try to assess all the possibilities available to you, you quickly find yourself overwhelmed, maybe even wishing for less freedom.

CEO obligations

Generalists need to be a bit more structured than the average person if they’re going to balance many different interests in their lives. It takes planning and discipline, and generalists will need to initiate everything themselves, which is harder than following a well-trodden path in career or education.

It can be hard to organize and prioritize different activities; each one has unique demands and a unique structure of progress. Some require daily investment, others monthly; some take a year to reach a milestone, others take only a week; some can be put on pause without losing progress, others quickly deteriorate.

(That said, this is a type of problem that I particularly enjoy working though, and through my coaching I sometimes get to help people organize all their goals in a balanced way).

The planning trap

This struggle is actually kind of the opposite of the previous. Generalists sometimes plan too much. When conscious long-term planning is important in your life, you may get really good at it, and you may enjoy it. But that enjoyment might turn into passive recreation and you might forget to do anything. This is a whole flavor of procrastination: constantly tweaking all your big-picture plans when really you just need to work.

Generalists need to determine when their plans are good enough and it’s time to execute. They must be able to switch off the “Manager” and become the “Worker.” They ask, “Is it a good time to be the Manager here?” “Has the Worker clocked in today?”

The life not lived

“I just don’t have time to do everything.” The right answer to this is often “budget your time better”: quit your addictions; get off YouTube/TikTok/Instagram; consider all the ways you could spend a bit of extra money to save time on things; plan better so there’s less task-switching; and so on. But although there may be a lot of easy gains in time management, we also have to accept that time is finite, and burnout is a real risk.

Sometimes generalists have to make hard decisions about whether to continue this or that project. To take something that inspires genuine interest and let it drop out of your life is a sad thing, but sometimes necessary. To “retire” is a little easier.

Conclusion

If you’re done brooding on the generalist’s struggles and want a pick-me-up, take a look at the generalist’s strengths.

1. Idea Synthesis

Generalists tend to be good at combining knowledge from different fields into new concepts, or applying concepts from one field to another in a novel way. This brings about invention and innovation, and it’s probably the most obvious strength of generalists.

Leonardo da Vinci’s paintings of humans were improved by his interest in anatomy and his experimental dissection of cadavers. Steve Jobs’ knowledge of design and typesetting led him to create user-friendly products that revolutionized personal computing. And so on.

2. Rapid Learning

A pure specialist might be a beginner in something only once in their life—soon they’ve mastered the basics and move on to fine-tuning, building good habits, managing their psychology, etc. But generalists are more accustomed to being novices—every time they spark a new interest, they have to be a beginner again. I think that’s why “Learner” was the highest Clifton Strengths category among generalists.

The only skill you can always take with you, from one interest to another, is the meta-skill: your ability to learn skills. Generalists get to exercise this muscle more than the average person, and this lets them thrive in dynamic environments where continuous learning is necessary.

3. Empathy

Generalists have an easy time connecting with a broad set of individuals and cultures. By “cultures” I don’t necessarily mean those in foreign countries. I mean all the little subcultures you might encounter in your daily life.

For me: I studied physics in school and have had a career in Big Tech since then. I enjoy programming; I enjoy analyzing things by their parts; I have a materialist understanding of reality. Now, what is my opinion toward artists, who live in SoHo lofts and paint all the time? They’re my people too, and I relate to them directly, because I’m into art as well. And even the forms of art that I’m not particularly good at, I understand and appreciate.

To invest in and appreciate many different subcultures gives one a better picture of what’s common between them—the essentials of human nature. It enables you to see through the cultural specifics and find those essentially-human traits and experiences, and understand them more readily. It shrinks your outgroup, which is a bigger topic than belongs here.

4. Adaptability

Generalists are all, to some degree, chameleons. If you apply yourself to two wildly different things, then there are probably at least two wildly different social circles that you fit into. And you might even feel there are a corresponding two different versions of yourself.

Because of multiple group memberships, generalists are likely to hold multiple ways of thinking, multiple communication styles, multiple sets of social norms, etc. All of this is conducive to adapting to novel environments.

5. Avoiding Efficient Competition

Generalists have unique combinations of skills, and that can open up opportunities to do unique jobs that not many people are fit for. Occupying a very niche job is good for job security and labor value.

By contrast, standard jobs that require a single narrow skillset are subject to efficient competition, meaning it’s very straightforward to measure a worker’s competence, so workers have to compete fiercely with each other to stay valued.

6. Analogical Thinking

Generalists are good at analogical thinking—that is, taking a mental model from one field and applying it to another, in hopes of understanding the other field better.

A planet in orbit is like a ball swinging from a string. The way ideas spread through a culture is similar to how animals survive and reproduce and evolve. Electric currents flow through conductors like fluids flow through pipes. Time is like a direction in space that we’re all moving through at a constant speed. Your relationship to your future self is like the relationship between a manager and employee in an organization. And so on.

Analogies help you conceptually grasp a novel situation—to identify the important concepts and use those concepts in a mental model that gives you a deeper understanding of how the system works. This method has historically led to countless breakthroughs in human knowledge.

Generalists have a wider pool of experience from which to pull analogies. By default, they’re using more mental models day-to-day. You could say analogies open up new dimensions of thought. When you’re hitting an obstacle head-on—just continually backing up and hitting it again—an analogy lets you go sideways. The more analogies you can apply, the more dimensions you can “move” in.

7. Avoiding Trapped Thinking

I once wrote a bit about how we partialize our sensory experience, reducing a huge amount of raw information to a relatively small set of concepts that our conscious minds can handle. That set of concepts is mostly determined by the set of words we know. Practically, it’s also determined by which concepts are familiar to us.

Different fields of work and study make you see the world differently. Each one gives you a unique set of concepts, and the more time you spend in that environment, the more comfortable you are applying those concepts as the “interpretation layer” between your raw sensory experience and your thoughts.

For example, if you’re a software engineer, there is a way of experiencing the world that is characteristic of software engineering. It’s evident in how software engineers talk to each other—not just about software engineering, but about anything. And it’s not just a particular vocabulary; the concepts behind the words are unique and characteristic.

• Maybe you’ll sometimes think of people as nodes in a graph. You see real-life situations as “systems” and you think about their “inputs” and “outputs.” When someone asks you a question you notice the “data type” of information they’re requesting. You notice the rules the system abides by. You notice hierarchies in relationships.

Every trade is like this. It only becomes obvious when you get into more than one concept-space. If you have multiple social groups, and they’re of truly different subcultures, you notice how they can have the “same” experience but process it completely differently.

This also affects how you find knowledge and form beliefs, and that’s where it’s especially dangerous to be trapped in a single mode of thinking. From the Range review:

Epstein describes the US Challenger disaster. Key decision makers gravely misunderstood what a “factor of safety” meant, they decided to launch the shuttle despite some warning signs on their equipment, the shuttle was destroyed, and then famous physicist Richard Feynman yelled at everyone. But Epstein reveals an angle that I’d missed the first time I’d heard this story.

Part of the reason NASA went ahead with the launch despite “warning signs” was that they had a systematically data-driven culture, and the warning signs were not quantified in any data. “The O-rings did something weird in the test, and although the equipment didn’t fail the test, it was unexpected. What if they do something unexpected again, but worse?” That kind of objection ran up against a culture of, “Nice idea, come back to us when you’ve got data.”

You can imagine how well a data-only culture had worked for NASA, and how much waste it had successfully dismissed. But it blinded them to a black-swan-type threat.

It’s an example of one particular way-of-knowing (post-war-modernist, data-driven techno-optimism) being useful for most things but failing in a critical case, where another way-of-knowing (physical-materialist pragmatism) would have succeeded. In the grand scheme, these worldviews are not even very different (both could be reduced to “STEM nerd”!), but the inability of one to see reality through the lens of the other led to a catastrophe.

All mental models are wrong, but some are useful. If you spend too much time in the same concept space, you forget that it’s there. The lens through which you’re looking becomes invisible, like how when you look at a video on a screen, you forget that there’s a screen, or that it’s a digital video.

Generalists have a better chance of getting familiar with multiple different concept spaces, thus noticing the differences between them, and thus noticing the limitations of each.

Conclusion

So there, generalists. These are our advantages, that I know of. Take it as a source of encouragement and inspiration, this unique set of gifts that we have.

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• "Maybe I shouldn't start this just yet; it'll be easier after {future event}."

• "What about this smaller task? I can get it out of the way first, right? Then I'll have a clearer head."

• "Actually, let me sort all my tasks by priority first."

• "Actually let me color-code them by category, too..."

And so on. You spend so much time making plans about when and how to allocate the work, that you run out of time to do the work (and maybe that's the point; more on that later). Do you ever feel like you've put in a very productive few hours, but you have nothing tangible to show for it? Do you habitually learn popular productivity systems like Getting Things Done or Atomic Habits without actually changing your day-to-day life?

Manager mode

I call this pattern of thought the "Manager." In the workplace, a manager sees the big picture, plans far in advance, puts the right systems in place, and decides what work is most important. By contrast, the "Employee" does most of the hands-on work, under the Manager's direction. As productive individuals, we have to be both the Manager and the Employee at different times.

This distinction actually maps very well onto a concept in neuroscience. Large-scale brain networks are sets of specific brain regions that activate together in certain situations. The Default mode network (DMN) or "task-negative network" is the large-scale brain network that's found to be active when the person has no ongoing tasks: daydreaming, imagining, remembering, planning, and the like, all belong to the DMN. When you engage with a well-defined task, the DMN stops, and the "task-positive network" (TPN) or Dorsal attention network comes on. The task-positive network governs goal-oriented behavior: it's the opposite of imaginative or wandering; it just deals with the given task.

(Thanks to this old Ribbonfarm post for originally introducing me to the DMN/TPN distinction. I've found it to be a really useful model over the years).

The overactive Manager

If you're an "overthinker" who never stops planning, you're stuck as the Manager. When you try to be the Employee, the Manager jumps right back into the spotlight. It says, "Actually don't work on that just yet. Let me think... I'll get back to you." And then you're back in planning mode.

If you dwell too much on Manager thoughts, your brain is stuck in DMN—you're constantly exploring the space of things you know and remember, looking for opportunities or anything important to act on. On the other hand, if you were doing too much TPN, you'd be constantly "heads down," never evaluating whether the goal is good or how it fits into your life.

I've paid enough attention to this process that I can almost feel it happening now. If I'm at the gym in the morning and I accidentally think for more than two seconds about what I'm going to do later in the day, boom the Manager is there, checking my calendar, sending texts, making decisions. I'm just supposed to be lifting weights! And it's hard to refocus after that happens—the Manager is having too much fun. It's a bad habit that has eaten up a lot of my time.

The generalist's Manager

Not everyone has the overactive Manager problem; some have the opposite and should reverse all the advice in this post. But generalists are naturally more Manager-adept. Any time you switch tasks; any time you decide to do a little work on your side project or hobby after work; and any time you make a plan to reach a milestone in something new—that's the Manager. And you need it! It's great to be intentional about balancing all your interests in a way that works logistically. But you also have to be able to call the plan "good enough" and be the Employee.

Why am I over-managing?

What makes a person get stuck in Manager mode? That question is actually mysterious to me, and I think the answers are deeper than the scope of this post. The obvious just-so answers just invite more questions. I'll list some speculations:

• Maybe you just have a fundamental preference for Manager-style work. It could be a deep personality trait; some result of your genes or early childhood experiences, and now it's locked in permanently. (Is that even how personality traits work?)

• Maybe you don't trust that you're actually good at managing—you're afraid the plan isn't good enough, so even if you try your hardest, it won't work and your effort will be wasted. (But wouldn't simple feedback and learning-from-mistakes inevitably make you a better and more confident Manager?)

• Maybe it's the classic fear of failure. You can't fail if you don't act, and you can't act if you're still planning to act, so you keep planning. (But why is there a fear of failure, but not a fear of indefinitely-delayed success? The latter can be more dangerous.)

• Maybe we all just have a fundamental urge toward inaction/laziness, and we'll subconsciously use whatever excuse we can find to procrastinate doing work. (But why would we be programmed for laziness? What advantage does that offer?)

• Maybe it's society's fault! The modern world favors the Manager by giving us all endless options in our location, work, play, relationships, etc. Choices, choices, forever. Maybe we didn't evolve for that kind of life. It sure seems like for most of human history and prehistory, the masses did not have many options for filling their free time, if they even had any. Having optional life-paths is a luxury that groups had to earn with a surplus of food, security, and coordination. So perhaps our lives are spoiled with managerial decisions now, in the same way our diets are spoiled with sugar.

We each might benefit from examining this question more deeply... or we might not! Deep introspective self-analysis can easily become another form of procrastination. "My whole issue will dissolve once I figure this out. I just need to meditate every day, and read this book by Freud and this other one by Jung, and maybe the Tibetan Book of the Dead, and then-" No maybe you need to just work!

Taming the Manager

So, the Manager is overactive; practically, how do we get around this? This is a classic productivity problem, which means different people will find different solutions, but luckily there are a lot of solutions to try. Here are some suggestions—definitely not an exhaustive list.

Scheduling (meta-planning): Can we plan when to be the planner? Can the Manger keep itself in check by blocking out chunks of time where "I will not do any managing, I promise"?

• You could have dedicated Manager days and Employee days. On Employee days, you bite the bullet and resist the urge to take a step back and analyze the big picture. On Manager days, you brainstorm and plan out the tasks for the next few Employee days.

• Or maybe within each day, you have Manger time and Employee time. Neuroscientist podcaster Andrew Huberman notes that in the earlier part of the day, we have higher levels of dopamine, epinephrine, and cortisol circulating in our bodies, which predisposes us to the kind of bounded, linear, step-by-step tasks that the Employee handles. In the latter half of the day we have more serotonin circulating, which causes a more relaxed state that's suited for the open-form, exploratory tasks where the Manager works. I haven't found this pattern to match my personal experience, but I do have a daily rhythm that works for me (I start the day as Manager, and when I feel like my day is planned well enough I deliberately switch to Employee, and maybe I'll switch back to Manager later in the evening). It probably depends on your sleep schedule, your meal schedule, and your own psychology.

Mental state induction: These can be used in combination with intentional scheduling: what do you do when it's actually time to switch modes?

• Audio: Music can be really effective at changing your mental state. Put together a work playlist that gets you into the zone and keeps you there. Mine has a lot of action movie and video game soundtracks because those pieces are designed to connote energy/momentum without being distracting. Or try pink/brown noise. If you're a very auditory thinker, like I am, you'll benefit from some kind of audio base layer to literally "drown out the voices" that pull you out of your work.

• Meditation: I'm not a good meditator; I've never done it with enough dedication to have deep insights or lasting personality changes. But one thing I've found it consistently useful for is switching in and out of these mental modes. I'll take five minutes where I close my eyes and just think about being the Employee/Executor/Worker and leaving behind the Manager. That's it. I don't know if anything "real" is happening when I do this or if it's just the cost of "pausing my life 5 for minutes" that gives the decision some weight, but I always find it easy to stay in that state for hours after.

• Location: Can you do Manager things and Employee things in different places? Changing locations can be a nice little ritual to reinforce the separation between modes. In the actual workplace, the manager and employees sit in different offices; even in open office plans, my company took care to give managers their own spaces wherever possible. There's a reason for that!

Tech tools: Is there some technology you can use to keep yourself out of Manager mode?

• Set a pomodoro timer: Do Employee work during the session, and Manager work during the break. Or do an Employee round, break, then a Manager round, break, etc. Any ritual has a decent chance of working, if you do it enough to reinforce its meaning in your mind.

• Set deadlines: Have you noticed that when a deadline is fast approaching, the Manager is nowhere to be found? It's much easier to be the Employee when you must. This is the basic utility of procrastination. You wait until the deadline is nearly up, because a nearly-up deadline naturally shocks you out of DMN—it doesn't take any special effort. However, that is a stressful way to live. Most people who live in the procrastinate/cram rhythm would say it's not ideal... but it does work.

  • The trick though, is that as a productive generalist you'll likely be setting your own goals and deadlines. A self-made deadline can be self-delayed. You might have to use little schemes with your friends or colleagues to get real external accountability for your own personal deadlines.

• Take notes / write to-dos: This is an indirect solution to the problem. When you have a notetaking system that's quick and reliable and organized, you can dump fresh ideas into their proper place as soon as you have them, and then promptly forget them; you'll develop them further when the time is right. A to-do list functions the same way. Your Manager insights could be things-to-do or things-to-think-about or aha-moments, etc. So notes and to-dos are kind of part of the same system here.

  • This is a big part of my writing process. I'll be going about my day, and I'll make a connection from some new idea to a topic I'm drafting. I'll throw the idea into the existing draft and then forget about it. Months or years go by before I decide I'm ready to develop that topic. Then I'll open the draft and see what I've got; I start ordering the ideas and tying them together.

Try any of the above, or all the above, or your own ideas. It doesn't matter how you get there, but know that at some point you do have to put your head down and do the work. A company of all Managers would quickly fail. Both work styles need to be present and in harmony in the same body—literally, a "corporation."

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There are exactly 2 kinds of businesses in this world. Businesses that are perfectly competitive and businesses that are monopolies.

Peter Thiel

The work of a specialist can usually be measured and rated on a single metric, or something close to a single metric. A mechanic can be graded on how fast they fix cars, and how long those fixes last. A surgeon can be graded on how many successful surgeries they've performed and how many had complications. Having clear performance metrics is very good for, well, performance. But in the broader picture of your life and career it can be a bad thing.

We're all competing in markets—either against other employees in the job market, or against other businesses in the market for a particular product. The most fit competitors tend to survive, but that's not the whole story.

Legible markets

When your fitness as a competitor is legible—when it can be easily seen and measured—, that makes competition more efficient. That means if your neighbor is ever-so-slightly more competent than you are, they'll be chosen for the job before you, every time. Efficient competition leaves less room for the "soft values" like personality and culture fit. And it leaves no room for creativity.

In a perfectly efficient market, competitors would have to dedicate 100% of their efforts to that one metric of competence, or else they'd be outcompeted by others who did so. This basically destroys the "work/life balance," encouraging overworking at the expense of all the other things that make life worth living. It's an undesirable outcome, but it's how efficient markets naturally work.

On the other end is illegible fitness. Some jobs are very hard to measure competency in. For example, which composer should be hired to score a movie? There's no easy way to rank people by "competence at composing the kind of music that's right for my movie," so there's no clear way to choose the best value per cost. How does the film producer make that hiring decision? He uses a set of soft factors, like "I know the guy" or "I really like that one piece she did" or "He has experience with the subject matter of my movie." It's an illegible process—it doesn't lend itself to any kind of simple formula.

Efficiency increases by default

Real-life markets tend to get more efficient over time if they're left alone. As information propagates to buyers and sellers, they make more economical decisions and find opportunities to capture any extra value from all the options available. Every stock market tick is an adjustment toward efficiency. So is every trade deal, every firing of a low performer or hiring of a high performer—really any informed decision made to increase economic value. It all increases efficiency.

That trend gets somewhat reset whenever innovation drops new value into the market. A brand new product has one seller at first; then others learn how to make it, and they offer a cheaper version, or a premium version, or an international version, and so on. All the potential value of the innovation is gradually captured by competition.

There are also some broader trends toward efficiency that won't reset unless there's a catastrophic change in the world order:

• The globalization of products: The economies of the world are generally getting more interconnected. Countries find arbitrage in trading overseas. For any given export, there are at least a handful of countries that can offer it; they're now competing with each other.

• The globalization of labor: Global companies use the Visa program to get more talent from overseas, growing the supply of labor and in turn lowering the cost of that labor. They also use partnerships and subsidiary companies to outsource some of their labor to cheaper local markets.

• Remote work is a similar trend—companies can attract employees from anywhere in the world, rather than just from the region where their building is. After the initial remote-work leap triggered by COVID, this trend is just beginning to take hold. Many businesses still aren't ready to fully exploit it—they're locked into their facility costs/rent, or they don't believe their employees can work as well from home—but those hang-ups will eventually be resolved. Leases will expire, buildings will be sold, and new technologies and protocols will be instated to make remote work more effective and put managers at ease. An arbitrage opportunity of this size won't be ignored.

The world is opening up, markets are constantly expanding, and it would take a truly apocalyptic event to stop it. Efficient competition is getting more efficient; this is the way the world is going.

Be unmeasurable

Generalists are well suited to find illegible markets to work in.

For example, I'm a technical writer in big tech, and it's a narrow niche. When I got hired, my background was in physics, not computer science. Others in my role have backgrounds in English, business, and even music. We're a weird group of people with a weird set of skills. We understand software well, have decent coding skills, are very good at English writing, and can model the experience of both engineers and managers who read our docs.

It's hard to measure the performance of a technical writer. Do you count docs written per month? But that depends on how many docs our partner teams need written. And what if the docs aren't helpful enough? How do you measure the comprehensibility of a doc? We certainly try to measure the quality of our work, but it's imprecise. Compare that to many engineering roles, where your performance can be completely measured by a combination of 1) how many lines of code you write per month, and 2) does the code run without bugs?

The end result is a very good work/life balance. There's no "on-call"; there's no "we have to push through the weekend"; there's no "we'll extract as much value from you as possible in the first two years because we fear you'll pivot to another company after that." The company just needs us to do this one particular job. In eight years I've seen one person in my role get laid off.

Generalists shouldn't need to outcompete the masses in standard jobs with legible performance measurements. They'd do well to look for the weird jobs at a company, the ones that only a handful of people have the right mix of qualifications to do.

True Monopolists

The step beyond landing a niche job is, of course, going out on your own and inventing a product or process that no one has ever thought of—a testament to the uniqueness of your skillset and knowledge base. The more narrow your niche, the closer you are to occupying a monopoly, where you (or your product) can't be replaced by an alternative.

If you’re the founder…entrepreneur starting a company, you always want to aim for monopoly and you always want to avoid competition.

Peter Thiel

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Full-length novels are being written in a matter of days. The framework of a new business is laid out step-by-step. A new style of art is developed. A new style of comedic content hits YouTube. And so on. AI is going to continue changing our lives in ways we can't predict, but one major change that seems to be playing out is that AI can be your specialist—an "employee" doing something specific under the direction of you, the "manager" of the project.

(Let me point out that although this post focuses on the advantages of recent AI developments, that doesn't mean I deny any disadvantages. It's true that AI tools are starting to replace human jobs, which is causing widespread agitation. I don't say this disinterestedly—it's likely coming for my job, too. The best we can do is adapt to the new status quo and prepare for what's next.)

Employ AI

When you have a big idea that ties together many of different kinds of work, like a multimedia product or a business idea, at some point you need to recruit specialists. It's more efficient and frees you up to focus your skill and attention on what's unique about your vision. Find tons of examples of this in Things you're allowed to do.

But what if you're not confident enough in the idea? Not ready to invest your own money? Or maybe you're worried you'd be a difficult boss to work for: too micro-managing to your vision. Maybe you're worried about getting scammed by a stranger. Then you might wait on the project. You might find yourself blocked from ever making a minimum viable product.

Enter AI! You can "hire" AI to do certain parts of your project for you. At the time of this writing, AI models can do the following, at a level that meets or exceeds that of most people:

• Write: It can write (and help you write) almost any kind of content. That means:

  • Content that is the product itself, like blog posts.

  • Content that aids the business, like marketing copy.

  • Business communications, like cold emails.

• Read:

  • Use AI to summarize content you have to read.

  • Use it to pore over customer feedback and extract key insights about your product.

• Illustrate:

  • Visual content that is the product itself, like art for your book or website, or memes for social media.

  • Marketing content, like the logo for your brand.

• Produce:

  • Video content! This is still in its early stage at the time of this writing, but AI can generate video clips from just simple text prompts, and they look pretty good.

• Speak:

  • AI Text-to-speech is often indistinguishable from organic speech. Use it for any narration you need.

• Program:

  • If you're a novice at coding, technical projects can take a very long time. But AI models are very good at writing basic code that does what you ask. A small skill base in coding plus AI lets you build out your technical projects much faster.

• Brainstorm:

  • AI chat models can generate business ideas as well as sub-niches for your business. Try asking it what kind of project you should work on, given your eclectic set of skills.

(I left out a ton of use cases. But even if I put together an exhaustive list, I know it would be out of date within a month. AI is moving that fast.)

(And, I'm talking about generative AI specifically here—AI models that create content. I'm not mentioning the myriad other AI tools that have been around for a while, that do things like help you search an index, tell you what's in an image, transcribe audio, etc.)

Now, so far it's been clear that AI models aren't quite the best at the above tasks - they don't exceed the skills of the best humans. But if you're a generalist in the early stages of a creative vision, you probably don't want the very best, nor do you want to pay for it. AI models will get you through the prototyping stage at incredible speed. And if current trends continue, future AI tools will put out higher quality work and be more seriously considered as real business assets.

I can't overstate the degree to which this opens doors. Hey, I love writing, so I write all the content for this website myself. But if I hated writing and still wanted to do a project like this, I could! I could always partner with or hire a writer, but now it's even easier: I could "hire" ChatGPT for free, or nearly free.

Leverage small investments

AI is a force multiplier for "dabblers." If you have even a surface-level aptitude in something, you can make AI-generated work look excellent.

Some basic skill investment is required on your part, but only a bit, so that you can judge the quality of the work. If you're just okay at writing, you know enough to say, "This sentence sounds weird," and the AI will give it another try. If you're just okay at art, you can say "This part of the image looks weird," and have the AI redo just that part. Personally I'm just okay at programming, so AI programming holds a lot of promise for me. I'm good enough to check and edit code, but I benefit massively from an AI that writes most of it for me.

And this is terrific for generalists, who are natural dabblers. There are now fewer things you need to master (or hire masters for) in order to get your big idea out there. Dabble in all parts of the project, employ AI tools to do most of the work, and then verify that the quality is good.

Skip the overhead

With AI, you don't have to worry about getting scammed. You don't have to worry about whether you're a difficult manager or whether your critiques are constructive enough. You don't have to worry whether your idea is good enough to justify stringing someone else along. You can just start.

The casual CEO

Generalists tend to make great CEOs. That's small comfort to most of us, because it's hard to become a CEO: every company only has one! And it's hard to found your own company—to be sure enough of your idea and its profitability that you'll start paying people's salaries.

In other professions, this is not the case. You could ask yourself, "Would I enjoy painting?" and then just paint a little to find out. Now, you can ask, "Would I enjoy being the leader of a project or business?" and then hire an AI staff and be a casual CEO and find out. The gate is lowered; "CEO" is now like many other professions in that you can just try it out and see if it's for you.

Where to start

Here are some good AI tools that I'm aware of. I'm sure there are better ones out there, and I'm sure the list will change in the near future. But I still want to put out some practical steps for those who are curious and motivated:

• ChatGPT - generates text content; state-of-the-art quality, regularly improving

• Claude - also generates text content; competitive with ChatGPT

• Copy.ai - text generation specialized for copywriting

• GitHub Copilot - code completion and generation for all popular programming languages and platforms

• DALL-E - image generation from text prompts; easy to use

• Midjourney - image generation; considered to be the highest quality

• dreamstudio(Stable Diffusion) - image generation; greater variety of content possible

• Azure Speech - AI synthetic speech, including "personal voice" from an organic speech sample; also transcribes organic speech into text

Conclusion

Let's get to work! The winds are shifting. The specialist-centric economy that was shaped by the industrial revolution is gradually giving way to a creator economy powered by the AI revolution. As a generalist, you are uniquely poised to benefit from it.

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