But for many of us, the best example of this absurdity is the workplace. I was recently reflecting on one of these moments in my career. And it happened during a very absurd period of recent history: 2020.

Misaligned Priorities

I had been living in New York for about 8 months when the city shut down. Just having moved into a new apartment in Manhattan, I was a little bummed that I could no longer “walk to work”. But quickly, the work ramped up and I was incredibly busy. I was always busy at Uber, but we were hitting a new normal level of overwhelm (though still not as bad as before).

With the workload high, particularly in the food delivery space, I got approached with an ask that caused me to lose my mind.

Assistance on a “strategic” initiative. It was to launch catering as a service. Catering. As in food catering. For large groups of people. In the middle of a pandemic.

I remember at the time actually feeling a variety of emotions such as confusion, bewilderment, shock, frustration, and anger. Looking back years later, the entire episode is comical to me.

But in that moment, I didn’t know what to do. For a moment, I was questioning my own sanity, as it felt as though there were fewer people aligned with me than not. It was a true emperor has no clothes moment. The absurdity of the entire thing was amplified by corporate politics. The situation - as I saw it - essentially boiled down to the following:

1. There were two individuals with this as their primary project.

2. They were senior enough to influence other teams, but not senior enough (apparently) to question whether it was a good idea.

3. When I asked for support from my higher-ups, my recognition of the futility of the project was affirmed, but I was still met with the political mandate to “play ball”.

4. I countered that we did not have the resourcing at the time. It was true. Hiring was frozen, we were already underwater, and the workload had rapidly increased due to COVID.

5. It didn’t matter. I still needed to act within the constraints of the absurd conditions and decisions being made around me.

I ended up dragging this out as much as possible, fighting the “good fight,” in a politically acceptable manner. If there was one thing I had learned at a company that was growing more bureaucratic, it was how to make things as difficult as possible for others while staying inbounds.

(Not a great trait in life, as I now reflect. But absurd environments produce absurd behavior.)

Eventually, I had to give in and we began scoping the project on a Friday.

Come Monday, those exact individuals I was working with ended up being laid off. It was the weirdest shift of emotions.

Frustration --> stubbornness --> annoyance --> acquiescence --> grief

I never blamed the individuals. They were simply playing their parts in a poorly designed system, because at the end of the day they were molded to act in their own best interests. It wasn’t worth it for them to challenge the inertia of the moment.

Ultimately, it didn’t matter. They were viewed as unnecessary by the machine that they had become a part of.

These layoffs also eliminated half of my own team in an instant, which was the first major domino to fall leading to my exit from corporate life. This saga became quickly irrelevant to me in only a few hours, as my own team became my more immediate concern.

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Moral Judgments

Fast forward to today. For whatever reason this story stuck with me, and I’ve joked about it with friends and acquaintances often enough over the years to have lost count.

For nearly a year now, I switched from normal psychotherapy (normal in the terms of 2026) to Jungian analysis. This past week I shared a preview of this article and the story in general. My analyst used a technique which he refers to as amplification, which is where a specific word, phrase, or idea that I use is amplified by comparing it to art, literature, politics, philosophy, or anything else beneficial for comparison.

The phrase he latched onto when I told my story was “it can’t be done.” When he had me reframe it, I apparently used the words “the math doesn’t work,” which was my way of saying “100% of our resources are already tied up.”

He then began probing me to figure out if what I was saying was quite literal. As if it was truly impossible for this project to be taken on and completed:

• Could you have re-prioritized other items?

• Was it possible to get more resourcing?

• Were you able to do it at a later time?

• etc.

And then at one point, I was asked if I was making a claim that accepting this project was “morally wrong”? I don’t remember my exact response, but it was along the lines of “No, not morally wrong. Just stupid. Unless you believe those to be the same thing.”

These sessions never end neatly, with a clear lesson to be taken away. I sit with them. There’s never an action to take, or a powerful insight in the moment. The one point he made that stuck with me is that for every event that occurs in life, depending on the vantage point, there is always a different interpretation to be made.

Different individuals with different experiences, worldviews, situations, and incentives can have very different realities. In this scenario, for the two individuals I was dealing with, their priorities were likely justified: the success of the project may have had real impacts on their compensation, performance reviews, and career trajectory.

The tension was that we had been placed in a situation where my priorities and incentives were entirely in contradiction with theirs. With a situation that is more nuanced and complex than it appears on initial examination, it is no wonder that there was an emotional charge attached to this memory.

The Funny Part

If I sit with it long enough, I can partially recall various forms of negative emotions with experiences in the past. The frustration, the anger, the defensiveness, the exhaustion. My analyst even pointed out that my Ego was very evident as I “defended myself” when he probed into my story.

Which: why? It was so long ago, so irrelevant in the grand scheme of things, and my entire premise when I began writing this was that it was so absurd that the only thing to do was laugh.

But then it turns out, I still had some level of ego attachment to the story. I was actually arguing with him during our session about the facts, to convince him of how ridiculous the entire thing was.

So now I realize that not only was the situation itself absurd, but my emotional attachment to this narrative (which still clearly lingers to this day) is equally absurd.

Environmental Absurdity

Our environments inevitably shape who we are, and each of us must decide if and when a particular environment is no longer conducive to our own personal growth and ability to thrive.

But at the same time, I also must acknowledge we cannot always modify our environment to be perfect (or modify it at all). The absurdities of modern life will follow me no matter where I go. The rest of my life will be filled with the absurd. Levity and acceptance will be required. Sometimes all we can do is laugh and move on.

I said that the world is absurd, but I was too hasty. This world in itself is not reasonable, that is all that can be said. But what is absurd is the confrontation of this irrational and the wild longing for clarity whose call echoes in the human heart.

— Albert Camus

Or perhaps the world is not absurd, but rather I am.

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New York City. Expansion. Growth. Consumption. Wealth. Opportunity. Culture. Disillusion. Midlife. Passion. Rollercoasters. Change.

Designing a lifestyle that feels right for me is one of the key questions I examine every day, and have been exploring for a few years. I realized that New York no longer provided me the things that it once did, despite how incredible and inspiring I still find the city. A week ago, I moved away. The last month was a blur, with a perfect cocktail of emotions that I still have yet to grapple with.

But today I just want to write about the city of New York, and what that chapter of my life has meant. I was there for 7 years and 2 months. It’s the longest I’ve lived anywhere as an adult, and it was the first place I felt as though I truly wanted to be there.

New York offers so much, potentially unlike any city in the history of the world. The ultimate melting pot of cultures (and sub-cultures), cuisines, languages, experiences, and lifestyles. A city that can inspire through its skylines, its individuals, its opportunities and human-made beauty.

Its seasons are perfect on some days, oppressive on others, and average the rest of the time. Its brilliance presents itself in the extremes: high-end, exquisite dining, balanced by just as satisfying $5 bodega sandwiches at 1 a.m. But there is also so much softness and peace to be found if you know where to look.

The highs here are unmatched by anything I’ve experienced. The lows were periods that tested my patience and resolve. Most of my days were filled with adventure, growth, and connection.

Yet paradoxically, I reached a period in my life where the infinite possibilities and magical unpredictabilities of the city felt...limiting, predictable and dare I say, boring?

My 7 years here were the catalyst for the next chapter of my life that I am now entering, and I am truly grateful for the personal development that the city helped facilitate.

The amount of friends, friend groups, and communities that have entered my life is unparalleled. Though “entered” may be the wrong choice of word. I sought these things out as I never had in my life. This muscle of intentionality was one I had never felt the need to develop before. And now it’s opened up new possibilities for me moving forward.

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When I reflected on my time in the city, these were core aspects of my experience here:

• My 3 most career-altering experiences occurred here.

• It’s the most I’ve felt alive and that I would find myself in moments of pure joy.

• For over 3 years now, I was experiencing a form of chronic exhaustion that I have never been able to understand. It was not physical, mental or emotional. It was something else entirely.

• The person I was when I arrived has transformed into something radically different, which I am still attempting to make sense of.

• I found and participated in not one, not two, but five different communities over the past 5 years.

• I forged new deep friendships, and deepened ones from the past.

This year, for the first time, I felt as though my own growth was stalling. As if somehow the city had no room for me to expand. The city had shrunk and shockingly become small. In a melodramatic manner, I was using phrases such as “killing me,” “draining me,” or questioning whether I was feeling a sense of depression.

But the feeling actually isn’t that strong. It was less a desire to leave, but more a desire to seek something out. A different type of adventure. A series of quests. Examining different ways of being.

Not every day near the end felt like this. Sometimes I’d still find the magic. It was intoxicating. I’d go to sleep and wake up the next day realizing I wouldn’t feel this way anywhere else. Doubts about leaving would creep in. But then I’d ground myself again and truly examine what was it that I wanted for my future.

The best description I can give of this experience of over 7 years is that I’ve been living in the biggest and greatest amusement park you can imagine. I did a lot. But I have only explored 10% of the park. I learned what I liked and didn’t like. There were rides I absolutely loved, and I couldn’t help but return to them week after week. Each time was somehow a unique experience. And part of my current grief is accepting that I can no longer easily return to these places every day.

I am writing this from a town in the middle of nowhere with a population smaller than the block I lived on, which has created such a powerful contrast that allows me to look at my experience from the perfect distance. I feel as though I just ended this incredible relationship that was destined to end. The paths of meeting were aligned perfectly, at the exact moment in time that I needed them to.

I was at my lowest point in life before arriving. It felt like a rebirth. The world forced me to stop and be quiet for a year shortly after I arrived. Then I became fully alive again, rushing to experience as much as possible. Then I entered a crisis of sorts. I partially broke down over time. I healed myself. Many of my illusions and views of the world were shattered, while simultaneously I discovered my warmer passions and ways of expressing myself more truly.

My gratitude and appreciation are so incredibly high. I am excited for the next chapter of my life, while also knowing that any returns in the future will feel special.

Like millions before me, I sought New York seeking magic, opportunity, success and aliveness. I found them over and over, both within the city and within myself. I know that this experience has permanently changed me, and is something that will forever be part of me.

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As I attempted to design my ideal lifestyle, I realized it can be a bit overwhelming. There are so many different things I wish to do with my day, while also dealing with the constraints from external obligations and circumstances, ranging from job responsibilities to the weather that day (also acknowledging that those with children have a completely different set of constraints).

So what I did was this: I asked myself what I wanted my mornings to look like. It was the best place to start, as it is where the cycle of our entire day begins. Upon reflection, I have found that most of my mornings fall under these 3 categories:

1. Chronic stress and anxiety

2. Excitement

3. Peace, joy and optimism

Lifestyle Design

For me, Lifestyle Design is simply the act of envisioning and creating the conditions and environment that will allow me to thrive and flourish as an individual. This ranges from determining when and where we want to work, to how much urban vs. nature exposure we need, to the weather and climate that suits us best (I for one love cold, gray days more than most!).

For many of us, these can be out of our control. We may have jobs that require being in a certain physical location, with set hours, restricting our ability to change the above factors.

Enter the morning. Even then, there are certain critical professions (doctors, teachers, sanitation, etc.) that may limit the flexibility that I have recently found. However, I believe there is still an element of control one can have over how we enter our days.

Who owns your mornings?

In western society, we heavily value “productivity”. We have reduced human beings to productivity units, where our economy is purely incentivized to extract as much value and efficiency out of our human bodies and minds as possible.

An externality of this approach is how busy mornings have become. Our culture has co-opted the morning, and it is something that rarely belongs to the individual.

Until two years ago, I was always lending my mornings to someone or something else. From my early schooling, through college, and through my full-time career, I never had freedom in my mornings. I think back to high school: my school started at 7:20 am (!!! - once I even had a 0 period, which began at 6:15!). For most of my 20’s, I was waking up simply to check emails, Slacks, and attend meetings beginning as early as 7 am.

For 20+ straight years, I just accepted that mornings were full of obligations and not meant to be enjoyable nor peaceful. It was the norm.

So I began asking myself:

• How much value do I place on my mornings? Are they important to me?

• Do I have autonomy over the beginning of my day? If not, why? Who controls it?

• What type of mornings do I wish to have? What are the routines, experiences, and feelings I wish to have?

• What are the first things I want to do when I first wake up?

• Do I care about being productive in the morning? Or is my goal something different?

My Perfect Morning

There is this idea of optimizing morning routines that has been a byproduct of Silicon Valley and online “life hacker” circles that I find to be quite ridiculous, albeit humorous in the absurdity of it. In its most extreme platonic ideal, it might look something like:

• wake up at 5 am

• cold plunge/cold shower

• drink a glass of lemon water

• go for a long, early morning run or HIIT workout

• lengthy meditation

• executing on “important” items

• be at your desk at 9 am, already ahead of the rest of the world with your accomplishments

For the most part, I don’t think this is realistic, aside from a very small minority of individuals.

I personally realized I had no interest in doing anything “important” in my mornings. At least, I didn’t want to need to accomplish something. My mornings vary significantly from day to day, just based on how I am feeling, the weather, or what I have planned that day. But these are the activities that typically make it (sometimes I may only do 2 or 3):

• limited screen time the first hour

• long, slow dog walks through the park

• short (~10 min) meditation followed by some light reflection writing

• cooking a full breakfast

• making coffee at home or stopping by a cafe

• reading at the park or on the couch

• gym session

What I heavily avoid:

• meetings before 11 am

• checking email

• excessive screen time

• high cognitive work, unless I’m feeling inspired

• immediate physical exercise (in my first waking hour)

The key for me here is that I don’t have a strict schedule, or list of activities that must be performed (aside from the shower, dog and breakfast). I largely go by feel. On most days I do the majority of these things. But I do them because I enjoy them, not because of any obligation.

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Types of Mornings

Over the past week, I have experienced 3 very different mornings:

Groggy and Foggy

On a particularly warm and humid night, I seemed to not sleep well. I woke up knowing the day was going to be a drag. I woke up immediately tired, annoyed at the world, and dreading whatever tasks lie before me. This was a feeling I used to have quite consistently; now it’s rare. It’s less a feeling of sadness, but one of emptiness.

Everything on this was a struggle. I lacked excitement. I had to force myself to do the small amount of work I needed to do. I struggled to write this piece. I had no desire for social interactions. I spent more time on my phone in an attempt to escape my current discomfort.

The only solution I found was to go to sleep early that night.

Many people may simply refer to these as Mondays.

Calm and Joyful

The next day was the opposite, and my favorite kind of morning. I was rested. I had nothing urgent to take care of. By having a regulated emotional system that day, no matter what external events occurred, I was prepared to handle them.

These days lead to creative bursts, the ability to focus and think clearly, and general good decision-making. It creates a cycle of positive actions. Good diet, strong activity levels, a willingness to connect, sleep hygiene, and no desire to escape.

Excited

This one is more less common, but it did happen to me a week ago. I woke up at 5:45 am (after a very wild dream), and was simply unable to go back to sleep. For whatever reason, I had all of this energy to just do stuff that day.

Mission-driven individuals often speak about this feeling: when they are working towards something that feels important and also excites them, they are motivated to rise every day. As my current mission in life is to find my mission in life, I don’t typically enter my day feeling this way. But I do know it’s possible.

That day I had enthusiasm, curiosity and energy, while also being balanced out by patience and ease.

My goal is to create a lifestyle which minimizes the foggy days and increases the amount of peaceful mornings. My hypothesis being is that the peaceful and easy mornings will lay the groundwork that will produce more mornings of excitement and a healthy level of ambition: a state in which I am inspired to do things that give life meaning.

Roger Ekirch argues that, before the industrial revolution, it was normal to divide the night into two periods of sleep: the ‘first’, or ‘dead’, sleep, lasting from the evening until the early hours of the morning; and the ‘second’, or ‘morning’, sleep, which took the slumberer safely to daybreak. In between, there was an hour or more of wakefulness known as the ‘watch’, in which ‘Families rose to urinate, smoke tobacco, and even visit close neighbors. Many made love, prayed, and ... reflected on their dreams, a significant source of solace and self-awareness’ In the intimacy of the darkness, families and lovers could hold deep, rich, roaming conversations that had no place in the busy daytime.

— Pg. 96 - Wintering (Katherine May)

A Lovely Morning

I am nearing the end of a chapter in my life. After 7 years of living in New York, I realized it was time for a new environment, adventure and way of living. I have less than two months here. Due to this, my discipline on writing here has waned significantly.

I was struggling to figure out how to end this piece. In the past week, I almost forgot my intention.

So it was fitting that it took a great morning for me to write this. I initially wrote it by hand, completely disconnected from technology. It felt so much more natural, with the words just flowing out of me.

These calm, slow and peaceful mornings seem to nourish something within me, allowing more clarity and sense-making of the challenging world we live in.

Sometimes, my discipline, hard work, grit and logical brain are necessary for me to get started. But that has always been my default modus operandi.

It’s my untapped intuitive and unconscious side where my true insights appear to come through.

I came into this with a claim about mornings, and then to finish this piece I was able to prove it (to myself) in my every day life. Things were just easier today, and it was not part of any specific plan.

Society and the individual lives we live are full of paradoxes. So often, it feels as though the more effort we put into thinking and planning and architecting, we either lose sight of our original purpose, or face an outcome we did not expect.

But at the same time, living without a sense of intention, and allowing ourselves to be influenced by something that isn’t us, lands us in a place we’re not meant to be.

This whole exercise for me of figuring out what I want my mornings to be is an area for me to practice reconciling these two extremes. I don’t want a rigidly planned life, devoid of spontaneity, creativity and freedom of expression. I also don’t want to wander through life aimlessly, excessively vulnerable to the winds of change around me.

The more good mornings I have, the closer I feel I am to achieving that vision.

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I’ve probably written down hundreds of such questions, oftentimes the same question just framed differently. Many of them I’ve yet to properly answer. Several answers are constantly shifting.

One of the effective tools I found was actively trying not to answer every question. These are the types of questions that you normally cannot reason your way through. Friends, family, the internet or (god forbid) an LLM cannot give you the answers.

Sometimes, the best thing you can do is write a question down that you know is important to you, and just let it simmer. Make it visible. Put it on a sticky note on your front door, on a white board, or even on your phone’s lock screen. Have that constant reminder, without ever feeling the pressure to answer it immediately. It’s not a math problem.

Below are a few of the questions I believe anyone can benefit from asking themselves, spanning topics from money to joy.

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Money

Money, wealth, compensation, finances. A topic that takes up a substantial amount of emotional and cognitive real estate in our minds. There are so many layers that impact the role that money plays in our lives. For me, the core issue about money was me trying to understand where my beliefs about it come from. So much of this is embedded in our culture, economic system, parents and education.

A good starting point to untangle that web:

• What is money for?

• How much wealth does one need? How much do I need?

• Why do I desire it? How much?

• Where do my beliefs about money (and economics) come from? Which ones feel truly as if they are my own?

• What do I sacrifice in the pursuit of wealth?

• How much time do I spend thinking about money? What sorts of feelings arise when I am thinking about it?

• If I am currently pursuing wealth, does that provide me freedom, or restrict it?

• Do I have enough for a good life? If not, what would I need?

Work & Career

The natural extension of the money topic is work. For many of us, work is a means to a financial end. However, it is worth unpacking the fundamental question of whether there can be an inherently more meaningful version of work.

• What the hell is “work”? How do I define it? What has it meant to me in my life?

• When I hear the word “work”, what associations do I make with it? Is it more positive or negative?

• What would make work meaningful to me?

• What do I actually care about that would constitute work?

• Are there instances where the work I have been doing has excited me?

• If I am on a traditional career path, how did I find myself on it? Where do I see it headed?

• How much of my identity is tied to my job/career today?

• Do I only view work as a path to generating income? Is there work that interests me without a clear financial path?

• If my economic means were met, is there a form of work that I would still engage in?

Status

Status, achievement and recognition. Typically tied to our careers (but not always), this is something I find myself caring about less and less. In my personal experience, this highly correlates with earning potential, but also with a sense of identity the more we our invested in our careers.

• How have my views and relative importance of status, achievement and/or recognition changed over time?

• Do I care about my status? Professionally? Socially? Online? Why and how?

• When I’ve pursued status in the past, was it purely for financial reasons, or something else entirely?

• Do people I admire (or dislike) have high or low status? Or do they not seem to care about it whatsoever?

Joy

Here we begin to move away from the career and finance-related questions, and move into the experience of living. For me, this was the tipping point in my career arc: I was no longer willing to sacrifice non-work aspects of my life for work.

• How much (if any) joy does my work bring me (directly or indirectly)?

• At what points have I truly found joy in my work and career?

• What are regular, every day moments that bring me joy?

• What outlets do I intentionally seek out for joy?

• Do I crave more joy in my life?

• Do I understand the difference between joy and pleasure?

• Do I ever experience guilt about joy, whether when experiencing it or pursuing it?

• What is the relationship between joy, boredom and consumption in my life?

Community

I didn’t begin thinking about the idea of community until 2024. Since then, I have two core communities that I am a part of, with a couple others that fluctuate based on the seasons or my interests. As I reduced the time I spent working, this was the #1 thing that I filled that gap with.

• Do I know what community means to me? Is it different from my friendships?

• Am I part of any communities today? i.e. regular physical places that I regularly visit and see the same individuals, typically revolving around a shared activity or interest?

• For communities I am a part of, how do I show up there? How is that version of myself different from the persona on display at work, with friends or with family?

• Are there communities I wish to be a part of?

• Is there one I wished existed? Or perhaps one I might wish to create?

Lifestyle

This is the most interesting and open-ended set of questions on this list for me. Almost everything I am focusing on in life is with this as the endgame: what does my ideal, daily life look like?

• What do my mornings look like? Are they rushed and frantic, or slow, deliberate and calm?

• How much time I spending outside?

• What is my ideal balance between nature immersion and vibrant city life?

• How do I differentiate weekends from weekdays in my ideal week, if at all?

• What would it look like if I didn’t dread Mondays? How might I make the “Sunday scaries” go away?

• What are the recurring, daily activities I wish I always had time for?

• If I am engaging in work that feels meaningful, at what time of day does that work best for me? i.e. would I do my best work early in the morning, mid-afternoon, or when the sun goes down?

• If I were to map out my “perfect day”, from the moment I wake up until I go to bed, what exactly does that look like? Hour by hour.

• Do I envision a highly disciplined and structured day, or one that allows for high spontaneity?

Simply think of these as template questions. These should feel very personal, so feel encouraged to come up with your own. You may have your own set about romantic partnership, spirituality, health, parenting, or whatever else is important to you.

What is important is to not view them as questions that require perfect and immediate answers, but something that you can sit with and let your own truth arise.

We are instead in the habit of imagining our lives to be linear; a long march from birth to death in which we mass our powers, only to surrender them again, all the while slowly losing our youthful beauty. This is a brutal untruth. Life meanders like a path through the woods. We have seasons when we flourish, and seasons when the leaves fall from us, revealing our bare bones. Given time, they grow again.

— Pg. 78 - Wintering (Katherine May)

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I did some math this week.

7 years ago after I first moved to New York for Uber, on a normal work day, I had anywhere from 2-5 hours per day for myself. Two thirds of my life were simply taken up by sleep and my time in an office. The rest was split between commuting, getting ready for work, food, and other basic routines that are part of life (groceries, gym, laundry). This doesn’t even include the time spent thinking about work while not actually working.

Where the hell did my time go? And why in the world did I let someone else have full control over a majority of my life?

Was I stuck? Was it voluntary? Was I even aware at the time that this was happening?

Enter the Golden Handcuffs.

Golden Handcuffs

I am almost 2 years removed from full-time work and a life in which my default mode was immediate reactivity to the needs of others. It’s been 6 years outside corporate life. My perspective on work and life has changed substantially in this time.

It has also become easy for me to notice (perhaps just due to having the energy to notice) the patterns in which my friends, peers and acquaintances speak about their careers and their lives, particularly if they are in Tech. Some real phrases that I have heard all in the last month:

• “I didn’t think I would end up in this position.”

• “I’d like to do something different, but the money and the benefits are too good.”

• “I wouldn’t say I’m unhappy, but I don’t feel fulfilled either.”

The term “Golden Handcuffs” was created in the ‘70s, but has become more prevalent in recent years. In fact, Google provided me with a rough estimate that the term was searched around 4,000 times per month in 2021. In 2024 that number had over 10x’d to 50,000! This increase was cited based on a combination of several events, such as massive layoffs which “freed” individuals from their Golden Handcuffs, as well as the AI tech boom leading to massive increases in equity at companies such as Nvidia.

So what exactly are they?

In this BBC article from 2024, it is broadly defined as a phenomenon where workers get “trapped” in careers they “hate in exchange for rich paydays and luxury perks.” Individuals end up in positions that “offer vast sums of money to workers who often build their lives around massive pay-outs.”

How the handcuffs work is actually quite clear. While base salary is a big part of it, it’s the other components of a compensation package where individuals truly feel trapped. Stock options and RSUs that compound over years. High (and variable) annual bonuses (cash and equity). Lifestyle creep. Not to mention great benefits, of which healthcare is the most expensive and difficult to replace when not traditionally employed (in the US).

Through my own experience and through observing it in others, the trap also extends beyond economics. Status, achievement, cultural narratives around work, the stigma of pursuing alternative paths, and the very real opportunity costs that come with quitting. Even these non-financial aspects are still rooted in economic incentives long-term (e.g. your career status impacts your earning potential).

It’s a bit of a dilemma. Individuals in these situations are a relatively small percentage of the population, but are high-earners and have their material needs met better than 90% of Americans.

But something is still...off. This is not simply my observation, but the people living these lives are explicitly expressing it.

The cycle looks to be something as follows:

Acquire well-compensated job —> Work long, stressful hours —> Self-medicate with alcohol, expensive lifestyles, food, screens, extravagant but limited vacations, and other forms of escapism —> Lifestyle creep occurs leading to work harder for even higher pay.

Rinse and repeat.

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Incentives & Misalignment

One of my early themes is about misalignment in work, and the idea that we operate in a society in which individuals are not incentivized to explore their unique gifts and interests. Instead, our economic, political, educational and cultural architecture is designed in a way to ensure the placement of individuals in a certain role. It is part of the illusion of freedom and choice, limiting human potential in service of a broader economic system that is self-perpetuating.

Exactly “how to” break through one’s Golden Handcuffs is a highly personal challenge. Changing the incentive structure economically is a far more complex and lengthy conversation for another day.

But like anything, the first step for addressing a complex issue like this is the simple awareness that there is a problem. I never (consciously) realized it while deep in my career. It took me years shifting my identity away from work to even realize I had been experiencing it.

My Period of “Freedom”

I know both intuitively and objectively that quitting Uber and leaving corporate life behind, followed by “ending” my career 2 years ago, was the correct decision.

Yet for years I have had doubts and moments of wondering if I made a mistake. As I become aware of the compensation packages of my former peers growing over time, I wondered why I hadn’t just “stuck it out” and endured the BS. Just imagine how much more I would have right now! More wealth = more freedom, right?

I’ve looked at jobs, compensation packages, lightly explored the idea of what it would be like to go back to a startup or a “rocketship” again. Not once have I ever applied or spoken to anyone seriously. Likely because deep down I had no real desire to return.

But the idea that I would be willing to ask for those Golden Handcuffs again of my own free will, just illustrates how powerful a tool they are. I know a handful of people who share sentiments of frustration and desire to leave employers, but live with a belief that they “cannot” do so. It is the same force at play.

But with my time and space away, I know with almost 100% certainty I made the right choice. I changed my entire lifestyle. A newfound sense of freedom developed. I can freely think and feel more. I sleep better, drink less, eat better, and consume less in general.

The Impact

If you are reading this and work in a fast-paced, high-stress and well-paying career (likely in Tech, consulting or Finance), you may be experiencing some combination of the following:

• Intense (or subtle) burnout

• Chronic stress

• Questions of meaning in work

• Lack of fulfillment

• Misalignment

These are not personal failings. While Golden Handcuffs and our economic incentives were not designed specifically for these outcomes, they also do not care whether they occur.

Instead, the primary goal of a tool such as Golden Handcuffs is to ensure that individuals are placed (and kept) in specific roles to ensure the growth, stability and survival of the economic machine. I do not believe this economic system is intentionally good or evil. It’s simply amoral.

I know I personally made the right decision. Yet I still experience doubt and have little voices in my head asking “why not go back?”

But I know that is simply the incentive structure working exactly as intended. Society does not wish to reward decisions like the one I made. It aims to be punitive in an attempt to draw me back in.

It’s not a bug. It’s the primary feature.

A year and a half ago, while on my sabbatical, I had a dream. It was...kind of a boring dream.

It was about work. I was talking with my friend who was running the consulting firm I had left that summer for my first extensive work break. And somehow in conversation it came up that they had quite a bit of work coming their way.

4 months into my sabbatical, I realized I was open to experimenting with returning to work. Just to see what it would be like after having recovered mentally.

While I thought that the experiment was just about work, it was something entirely different. I was iterating on how I wanted to live. Exploring how work and money and my time spent on non-essential work could fit into a more meaningful life.

Fast forward today, I realize that form of experimentation represents something more. It’s a tool for us as individuals to build resilience for the increasingly complex future that is now our present. It’s a way for us to build the capacity to evolve.

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Quest for Meaning in an AI World

When I first came up with this idea about my “return to work”, I had no plans to weave in themes about meaning, or AI, or economic uncertainty. It was simply to talk about my pivot from being on a structured career path to one led by experimentation.

But now, we are transitioning into this new AI-dominated world. And truthfully, there is nothing we can do to stop that. This coincides with an ever-growing meaning crisis. Now as careers are upended and economic anxiety continues to spread, this question of meaning in life becomes even more pressing.[

My Experiment in Hindsight

I thought the experiment I ran following that dream was simply to examine whether I wanted to return to work as it was before. If I wanted to resume my career.

But what I was actually experimenting with was what type of life I wanted to live. The lifestyle I wanted. How I wanted my mornings to be. How much screen time I truly wanted.

I now understand that my first “career” was simply a transitional phase for me as I entered midlife. It has given me a large base of experience to reflect and write about. Economic incentives. Golden handcuffs. Free will. Sabbatical design. Intuition. The morality of tech. Work with and without meaning. The purpose of money and wealth.

(It also provided the added benefit of funding the life I am currently building.)

The Return to Work

At the time of my dream I felt as though I had mentally recovered. There was an itch to do something. After touching base with my old team, the project kicked off in the form of a 1-2 month discovery period.

Simultaneously, another former colleague also reached out to me who had joined a startup and asked me for some help as well. I took both opportunities.

November through January was great. The work was light. I was familiar with everything being discussed. There was no stress. It was easy money and it allowed me to maintain the lifestyle I had been building for myself.

Slow mornings. Long, intentional gym sessions. Lots of reading and writing. Dog walks to the park with meditation. Cooking all of my meals. Great sleep.

Lifestyle Breaks Down

At some point, responsibilities and the work began to build quickly. By April I had just taken on too much. I didn’t really say No to anything. I went from 0 to 5 clients in less than 6 months.

I had scattered meetings throughout my day. Slack messages late into the evening. I was in Puerto Rico for a few weeks, but even there, my mornings and afternoons were consumed by meetings, busywork, and the actual strategic thinking the role required."

Eventually I reached what I previously identified as a “Threshold Event”. This was the moment in which I said to myself “I can’t do this anymore.”

I consider this the inflection point where I ended my first “career”. This does not mean I don’t take on clients today if the work interests me, I enjoy the people, or if it integrates with my lifestyle.

But my boundaries are clear now. My identity is no longer tied to that work. I am not worried about a career to build within the confines of a specific set of rules.

Having that lifestyle thoroughly disrupted was not enjoyable. But now that the stress has passed, I look at that as another critical life lesson that has led me to the path I am now on.

Learnings

There were 4 core things I took away from my experiment:

1. Rest. It wasn’t just rest that I needed. After enough time without working, I felt confident that I had mentally recovered. But, even after that recovery, something was still off about the work once resumed.

2. Boundaries. I told myself after that I would not return to work like that. Work that was all-encompassing and that provided me little meaning. I’ll still take work, but it must fit with my lifestyle. I’m upfront with my limits from the beginning with potential clients, and every single person I’ve worked with has respected that fully.

3. Funding. I imagine if you asked people why they perform jobs that do not provide them meaning and joy, the answer would primarily be financial. That’s a topic for another day. But as I build towards a different kind of life, I view this type of work as purely a temporary means to an end. It provides me flexibility and security to build a meaningful life with the rest of my time.

4. Learning: This experiment felt like a failure when I hit peak stress. There was about a week where I wished I hadn’t taken on the project, or that it could just end. But having removed myself from that situation, I only view these types of experiments as successful, or incredibly informative. Do I wish to return to that situation? Absolutely not. But there is wisdom in that. And now, when I’ve experimented with different types of work, I am so much more precise in what I will say yes to.

AI and the Future

We have now entered the age of uncertainty engulfed by AI. Career experimentation to find work that is authentic, rewarding and financially viable may be one of our best tools to navigating the future.

There is anxiety. There is dread. But with all of this choice before us now, we do have a level of freedom to design our lives in a manner that is truly meaningful. And that is encouraging and exciting.

We owe it to ourselves to explore our gifts and bring those into the world. In fact, we owe it to the world. I believe wholeheartedly that there is a lane for each of us to operate in.

Writing about these topics for me is an experiment. It’s messy and imperfect and human. My subscribers and likes and engagement is low. But at the same time, I’ve received messages and even phone calls from people I haven’t heard from in years. In some cases, decades! There is something about what I am doing that is resonating somewhere. And that makes this worth it.

It is so easy for us as humans to feel overwhelmed and anxious about the future. Our brains were not designed to handle the level of complexity and stimulation in the modern world. But, we can regain agency by taking even the smallest actions towards figuring out how we wish to exist in this future.

Experiment away.

On the Bridge

For the past two months, I’ve been trapped in a cycle of decision paralysis. Feeling overwhelmed by my options. Increased anxiety. Decreased sleep quality.

I am in a transitory point in my life. It’s exciting, because for the first time I feel as though I’m actually building a life that is of my own creation. The hard part of this is that there is no playbook for me to follow. I’m not where I used to be, but I’m also not where I want to be.

I’m in the middle. I am walking on an unstable bridge where I cannot see what’s on the other side.

One of the real effects: it’s been weeks since I’ve published here. I had no idea what to write after my first 4 consecutive posts.

Surface-Level Success

I was raised and have lived the majority of my life in the US, the poster child for capitalism and technological advancement. The past 7 years I’ve lived in New York, the epitome for the extremes of this society.

I’ve achieved success on most surface-level metrics.

This has provided me a level of opportunity that 99% of people in the history of humanity have not been afforded. That is incredibly exciting.

But now? At this very moment. I feel crippled by infinite choice.

This ranges from boring, every day decisions to the most critical questions about what I wish to do with my life and whom I want to be.

I’ve noticed this humorous trend that happens to me on a nearly daily basis when interacting with friends and acquaintances. I’ll be having a normal conversation, and something like this will come up:

• Oh, you gotta watch this new show.

• Go check out this new restaurant. It’s incredible.

• Make sure you visit this city in this country and do x, y, z.

Ok. But do I? Actually? Why?

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How do I get out of this cycle?

Modern living absolutely creates the conditions for falling into this trap. Of always trying to optimize. Of wanting to research every potential choice and the outcome. Of leveraging AI and technology to refine our decision-making process.

But at the same time, I am fully responsible for this anxiety and decision fatigue.

I find myself stuck in daydreams and escapism, thinking about potential futures I could live. This is not a bad thing on its own. In fact, I believe envisioning possible futures (for our own lives and society at large) can be incredibly powerful. We are infinitely creative beings, and this should be constantly exercised.

But right now my priorities are misaligned. Particularly when it comes to my daily life.

Very few decisions in our lives will have a singular, best answer. The best we can do at a certain point is just eliminate some of the bad options.

Intentionality vs. Presence

My #1 focus in life right now is this 2 year clarity project I started last year. I want to be as intentional as possible with building the life I wish to live.

But, there is a balance here. And the equilibrium has been lost recently.

My ability to be mindful of experience of the present moment in my daily life has been lost. Spending so much time envisioning and planning for the future paradoxically makes the future more difficult to build when you are not in alignment with the space you are currently living in.

When I began writing this piece, I tried to ask myself, what is the challenge of trying to be intentional about the future, while also being fully present?

Freedom and overwhelm can be two sides to the same coin.

Optimization and quantifying everything has become our modus operandi in modern society

In trying to optimize our way towards this mythical perfect future, we hve lost so much peace of mind, human connection

This experiment in modern living has provided us such enormous economic potential and access to unparalleled opportunity in human history. The permutations available to us for the lives we can live and the societies we can build are truly infinite. But when that pursuit is left unchecked, we find ourselves on an impossible quest of constant optimization that can never be satiated.

My Decision Paralysis

A year and a half into leaving my career behind, I alternate daily (hourly?) between feeling liberated and stuck.

The biggest question I am asking myself right now is “where do I want to live next?” I have decided that it is time to close the New York chapter in pursuit of a different lifestyle. I have strong preferences about the weather, the cultural values, the types of people I wish to surround myself with, the hobbies I wish to engage in, the cost of living, the economic system, the access to nature, and the ability to assimilate.

There are three things I have begun telling myself in the last week:

1. I do not need to finalize any decision today. Nor even this year. I can test places out and experiment.

2. Remember to have faith in my ability to make life-changing decisions. I’ve ultimately followed my intuition and have never had regret about a choice I’ve made.

3. While I remain in New York, there is a balance I must strike between performing due diligence and finding joy through mindful, everyday life.

It was no accident that I began to gain a bit more clarity here when I was able to remove myself from my default urban environment.

The Costa Rica Art Gallery

I was recently in Costa Rica for 10 years for a wedding. I arrived a few days early to give me some time to explore on my own. On my second full day, I found myself in the same trap: unsure of what I wanted to do? How was I going to spend my day? How do I maximize the opportunity I had by being here?

More decision paralysis. But, when I look back, there were two specific parts that I highly enjoyed in which I did not spend too much time planning for or “researching”:

1. I ate at the same restaurant for breakfast my first 3 days. It was literally next door to where I was staying, so it took about 30 seconds to get there when I rolled out of bed. The coffee was great, and I enjoyed all 3 meals (even when they gave me the wrong item once!).

2. On that second full day, when I was unsure of what to do, I found an art gallery 10 minutes away. It had about 5 reviews, but they were all positive. So I walked on over.

The Art Gallery & Walden

And the thing about that gallery? It was perfect for me. It turned out that it was a gallery, (quite large) bookstore and cafe all merged into one. I ended up spending 4 hours in there.

First, I ordered an Americano. Then I walked around, looking at the various art. Then, I began looking at almost every bookshelf. I felt inspired to purchase something. Partially because I wanted to support the business beyond the coffee, but also because it felt as though there was a book that would speak to me.

I wanted to read the book that I had brought. I wanted to do a little writing. I also wanted to enjoy the A/C in the middle of the afternoon of a 90 degree, humid day.

There was quite a few books I was interested in. One was Dirtbag Billionaire, about the founder of Patagonia. A brief synopsis reads:

This is the inside story of one of the most extraordinary brands in the corporate world, the rare company that is driven by environmental activism instead of cutthroat capitalism.

While interesting, I opted for Thoreau’s Walden (with his Civil Disobedience essay appended). Funny enough, I bought this on Kindle years before but couldn’t get through it. For whatever reason, it wasn’t speaking to me at the time. But now, this felt like some of the daydreaming I find myself in.

The idea of distancing myself from civilization, immersing myself in nature, and living in a bit of pure solitude appeals to me. But at the same time, I envision myself as wanting to live in a vibrant culture, engaged in local communities, and spending time with people.

The funny part was while in Costa Rica, I spent quite a bit of time thinking about my future and exploring my options, just as I was in New York. But there, it felt a bit different.

Yes, I was future-oriented. But at the same time, I was doing so in a manner that actually made me feel present. The act of sitting in that gallery cafe asking myself these questions without the assistance of screens, was so fundamentally different than late night reading, leveraging LLMs or YouTube binges on my phone.

Immersion in Nature

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At the end of my trip, I went more inland with a friend and we stayed on the farm of a retired couple who had moved to the US. A Costa Rican family also lived on the property.

We spend two full days exploring the nature. Wildlife hikes and tours. Waterfalls. Hot springs. Hikes in national parks. Going to bed around 9 pm exhausted (but in a good way). Waking up early. Having home cooked meals for us for breakfast, and spending an evening for dinner in the Costa Rican home, with everything sourced from the farm we were staying on.

It was a small glimpse into that peaceful, nature-bonded life I was daydreaming about.

By the time I returned to New York last week, I reverted to my bad habits. Writing this piece has slowly helped pull myself out of it.

The Future Present

My plan is still to leave the incredible city of New York later this summer. It will be a full 7 years, the longest I’ve lived anywhere as an adult, and the first place I’ve confidently and warmly called home. But I also know it has run its course.

I still have major decisions to make about my future. But the majority of these questions I will not be able to answer properly while living here. Fantasizing and ruminating endlessly on a future that doesn’t need to be decided today does nothing for me.

The tension of wanting to connect deeply with nature, while also being immersed in vibrant, imperfect cultures and societies will likely exist within me for the rest of my life. I am witnessing my own worldviews changing rapidly every day, as I pay attention to what I am experiencing, what challenges my friends are facing, how my local communities are ever-evolving, and as the world feels as chaotic as ever.

The questions I feel called upon to answer, both for the individual and the collective will be lifelong pursuits. All I can do right now is enjoy the time I have remaining in this city. I’ll have to trust myself to figure everything else out at the right time.

Walden

It is not lost on me that I previously purchased a book about 2 years of solitude in nature, but was unable to get through it on an electronic reading device. I could barely get through the first 10-15 pages years ago. But the idea of a break from society, combined with Civil Disobedience during unstable times, connected with me so powerfully that day in the gallery.

The multiple layers of symbolism here are so not subtle that it doesn’t even require me to analyze heavily. But walking away from that trip physically carrying that book back to New York City feels like the perfect way to begin my final chapter of this phase of my life.

In my vision of an ideal society, I believe every human being should have the opportunity and economic means to pursue a sabbatical at least once in their lives.

From rest and recovery, pursuing innovative ideas or expressing themselves through an artistic outlet, the net benefit to both the individual and society can be difficult to quantify, but very positive.

During my sabbatical in the summer of 2024, I discovered a powerful version: personal transformation.

Before diving deep into my experience, I want to acknowledge that there is a very real economic privilege that comes with the ability to pursue a sabbatical. In a just society, I believe this is an opportunity that should be available to everyone. The benefits here are not simply for the individual, but for our communities and society at large.

Our Paradox

One of the stated benefits of western society is that the rights, freedoms and desires of the individual are prioritized.

Yet, the question that now needs to be asked is: how many people are actually able to pursue what they most want out of life?

Can we say that people are prioritizing their own dreams and desires — or are they largely devoting their energy to the dreams of others?

When we operate in a perpetual state of hustle and grind, when and where do we have the space to just sit and explore what it is that we most desire? Even in the case of a sabbatical, so many of us are still wired to plan, produce and perform. Can we simply stop, sit and go inside?

When I realized I did not have a strong sense of Self, and I believed that the work I was doing was standing in the way, I had to address that immediately. There was nothing more important.

The Answers I Found

A few months into my sabbatical, these were a few of the discoveries I found that were true for me.

1. Sometimes we just need to stop and step back. We need to dig deep. We have to peel back the layers of our psyche to truly understand why we are here. Why we do the things we do. What might feel wrong to us.

2. One of life’s realities is that we often have to take responsibility for challenges we did not create.

3. During a sabbatical, “surface-level” issues need to be addressed first. Resting. Sleeping. Rewiring our brains from bad habits. (Re-)Connecting with nature. Relating to people in new ways. Simply exploring the world and being present.

4. The answers to life’s most pressing questions do not live anywhere outside our own minds.

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My Sabbatical

What did this look like in reality for me? My sabbatical officially began on July 5th, 2024. I decided to remain in NYC for month 1. There are 3 things I most specifically remember:

1. The heat. It was HOT that July in the city. For anyone that knows me personally, they would confirm that I despise the heat. It wears me down.

2. I slept. A LOT. Immediately. It was almost as if I had not been sleeping properly since I was a child. As if my subconscious was always worried about whatever responsibilities I had in school and work. But I didn’t feel tired. I was just sleeping 10-11 hours. Since that period I average about 8-9 hours per night.

3. I did one of the most insane things in my life on Monday, July 8th. I...logged back into Slack (my accounts were still active temporarily). Why? Who knows. I guess I wanted to make sure everything was okay (spoiler: everything was fine). It was a completely compulsive and neurotic action.

Part of the planning in my sabbatical was intentionally not planning, in an attempt to challenge my default way of operating. Eventually, I woke up one day and decided to spend the entire month of August in Peru.

Active Recovery

I spent August hiking (most notably the 5 Day Salkantay Trek), immersed in nature, resting, disconnected from my phone and the internet as much as possible, and connecting with wonderful humans I crossed path with.

I returned to New York in September and spent the next two months just enjoying myself. My days were consistent and primarily filled with:

• Reading

• Writing

• Meditating

• Slow but intentional gym sessions

• Salsa

• Cooking

• Walking

• Resting

• Sitting outside

Slow Mornings

By the time November rolled around, my new lifestyle felt normal. My mental recovery felt complete. I started to get an itch to do something again.

But I also knew how much I was connecting with this slower lifestyle. A new non-negotiable value for me now is slow mornings.

When I think back on it. I don’t think I had experienced slow mornings since I was 3 or 4 years old. Growing up in California, school generally started around 8 am. My high school started at 7:20 am (honestly, wtf?). College grind followed by a decade of work grind (anywhere from 8 and 9 am meetings to even some 5 and 6 am ones).

That’s not something I can go back to.

This doesn’t imply not wanting to wake up early. But if I’m waking up early, it’s to walk my dog, write, read and make breakfast. Not to optimize business processes.

The Rewiring of my Brain

Once my chronic stress was purged, and I had a semblance of how I wanted my days to feel, changes began to occur in how I moved through the world.

• I never had so much time to reflect and just be. I was able to dig deep internally and examine so much of who I was, why I acted in certain ways, and how all of my experiences had shaped me.

• I found myself preparing for my weekly psychoanalysis sessions, allowing me to work on more fundamental aspects of my life than the surface-level.

• Meditating was easier than ever. In the past, my meditation practice was constantly disrupted by frivolous work issues. Now my disruptions became less frequent, but it was usually lighter (but more important) distractions such as salsa dancing or about human connection.

• My internal reflection and writing practice grew 10x. I no longer had to force myself. Any time I was experiencing internal tension, emotional challenge or an interpersonal friction, I just wrote. I found my thinking was just so much more clear. There were no meetings, emails or Slacks that seemed more important.

Reflection

Sabbatical Types

When I performed my initial sabbatical research, they most commonly fell under these categories:

1. Simple rest and recovery, i.e. work breaks (nature and meditation retreats would fall under here)

2. Pursuing a business idea, a calling, or an artistic outlet

3. Travel and adventure

And to be clear, you do not need to choose between these. Many sabbaticals combine these in different phases. In fact I did all of the above at various times.

But if I were to be asked about what I used my sabbatical for, I would have to answer that it was primarily used for transformation.

Personal transformation. Seeking clarity. Examining the Self.

I cannot necessarily measure the results in a tangible manner (ok, maybe sleep and decreased spending), but the payoff for me has been more valuable than any other single decision I’ve made in my life.

Final Thoughts

Some people may know exactly what they want to use their sabbatical for. Perhaps there’s a multi-month backpacking trip they’ve longed for all of their lives. Maybe they’ve always wanted to learn to play a certain instrument. Some have the “next big idea” just come to them and it needs to be pursued.

For me, I had no idea how I was going to spend my sabbatical. In fact, I didn’t plan anything at all from the beginning (aside from my budget).

What ended up happening instead was fully organic:

Time spent understanding myself deeply

Evolved my identity

Transitioned to a new phase of life with a new manner of operating

What results from this opportunity remains to be seen, but the possibilities excite me.

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Only once in my career have I ever had what one might consider a “breakdown”. But it felt minor at the time. In fact, it probably took me nearly 7 years later to even realize you could classify it as that.

It only lasted a few minutes, and did not feel abnormal then.

But when I look back and revisit that exact moment, I can recall upon all of the details with vivid memory. And I can trace a series of life decisions that have led to positive change and growth, and inevitably have helped me arrive at where I am today.

I’ve heard stories from friends and peers about similar types of breakdowns. Whether it was tears in the office, outbursts of anger, or even silent rage carried out behind the scenes.

These experiences can happen to most of us in the modern world of work. They can be subtle or highly explicit.

But in almost all cases, they are not moral failures.

They are not displays of weakness.

They are our bodies performing a labor strike.

They are when the body and the Soul come knocking on Mind’s door.

These breakdowns, such as a crying spell or a panic attack, are simply our unconscious mind speaking through our bodies.

Actually, not speaking. Screaming:

— HEY! NOT GOOD. CAN’T KEEP GOING ON LIKE THIS.

The Problem

In modern work, we do the following:

• Normalize chronic stress

• Champion grind and grit

• Live with burnout and work-related anxiety every day

For most individuals, suffering at work occurs slowly and silently. But some of us may be fortunate enough to receive a slap in the face when we continue to ignore this state.

But even when that happens, we prove to be incredibly skilled at suppressing and covering up these events.

However, at the end of the day, these are clear signals that something is fundamentally wrong.

They are pieces of valuable information, not something to be ashamed of.

Work-related breakdowns or panic attacks are not signs of weakness or any moral failing. They are simply a powerful form of communication that our unconscious mind is using to alert us of something critical, particularly when we are no longer living in alignment.

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The Panic Attack

Context

In 2018 I was living in Mexico City on a work assignment. Everything from outward appearances would make this sound like it would be one of the best years of my life. Housing fully covered in one of the best neighborhoods in an incredible city, wonderful food, a nice office, great coworkers, a San Francisco salary, and the opportunity to do interesting work.

But this ended up being the most difficult year of my adult life. It was the first time that I truly began questioning the point of the work I was engaged in. It was the most I ever sacrificed for work. Diet, sleep, and overall health were at the top of the list. But my general sense of mental wellbeing, social life, and any form of joy were also absent.

I spent my days in a constant loop of:

Chronic stress → Pleasure-based consumption → Poor sleep → Repeat

I worked 7 days a week. I slept forever on weekends. I drank. I partied. I ate. I serial dated. I woke up groggy and unmotivated. I traveled constantly.

The stress was a 15 out of 10.

This went on for months and months. But it got worse as time went on. The visibility by leadership and the (supposed) consequences felt suffocating. I was under-resourced, unprepared and had no support system. I didn’t even have a manager.

About 8 months in, I was running on fumes. After I had normalized the stress and embraced my new reality, it felt as though I was operating in a lull of “peace”.

And then one day something happened.

Panic and Shutdown

On a day that was no more significant than any other day, I was having a normal 1:1 Zoom call. I was sitting in our cafeteria, just having eaten breakfast. It was a low-stress meeting with someone I enjoyed working with. I cannot recall what we were discussing.

And then at some point, a co-worker that I did not know particularly well (friendly acquaintances) walked by, waved and smiled.

For whatever reason, everything in me froze. I lost all train of thought. The conversation I was in ended abruptly. The person on the other side could tell something was wrong.

“Are you okay? You seem distracted.”

I can barely recall what happened next. I remember needing to end the call, and the next batch of time was fuzzy.

It may have been 15, 30, 45 minutes before I could return to any sense of normalcy. I more than likely went to the bathroom, walked around the office, and may even have left the building temporarily.

All I can remember for sure was that I remember feeling:

• Panic

• Dread

• Stuck

• Anxiety

My mind completely shutdown. I was not capable of performing any type of work, nor interacting with another human being.

It was almost as if I was having an out of body experience.

Once I returned to a relative state of “normalcy”, I returned back to that same loop for another two months or so:

Chronic stress → Pleasure-based consumption → Poor sleep → Repeat

I never (consciously) processed the event. In fact, I have never shared it with anyone until writing this. The first time I reflected on it was when the idea to write about it came to me, about 3 months ago. 7 years later.

Processing

When anything like this has happened to me since, I realize that I had developed a set of tools that I automatically apply to address the situation.

1. Process the event, and properly internalize it, but solely as information. Not identity-forming.

2. Examine what you may be sacrificing by operating in the environment you have placed yourself in. For me this was my health, sleep, fun and deep human connection.

3. Ask for help and build a network to be leveraged as support as you work your way out of a negative environment.

4. Once the information has been understood as there being a real problem, the rational mind can begin developing potential solutions (as opposed to rationalizing to remain static).

What if all you had to do to avoid all of this was to let go in the beginning? If you had, you would have gone up instead of down. That’s how it works. When a blockage gets hit, it’s a good thing. It’s time to open up internally and release the blocked energy. If you let go, and permit the purification process to take place inside, that blocked energy will be released. When it’s released and allowed to flow up, it becomes purified and merges back into your center of consciousness. This energy then strengthens you instead of weakening you. You begin to go up and up, higher and higher, and you learn the secret of the ascent. The secret of the ascent is to never look down —always look up.

— pg. 78 - The Untethered Soul (Michael A. Singer)

How did I process?

I did not implement the 4 steps above at the time in any strategic manner, but I knew that something was terribly wrong.

In a roundabout way, I accomplished the goals of each, although I never consciously processed the event nor performed a proper reflection of the sacrifices I was making. It may have worked out because it was so damn obvious as to what it was that I was indeed sacrificing.

After that day, I began regaining a sense of agency in my life again. A series of positive decisions and changes occurred over the next two months. I:

• Got a new manager and built a support system again

• Hired a backfill for myself and began delegating all responsibilities

• Moved back to the US, eventually landing in New York

• Spent time with family and friends in California

• Re-positioned myself into a role in which I was fully confident in and could excel

• Was given the opportunity to hire and build a global team

• Removed chronic stress and returned to a manageable amount (6 out of 10)

• Properly invested in my health moving forward across all areas (sleep, diet, fitness, stress and social bonds)

Previously I have spoken about Threshold Events that led to me ending my first career. This Panic Attack was likely the first major work-related event that occurred which changed the trajectory of my future.

Looking Back

When I had the time to reflect and really re-visit this experience, I wanted to tie it back to the various themes that keep calling to me. Telling this story really called to me because it perfectly hit 3 of them:

1. Awakening: After living in an unsustainable manner, my body took charge and properly shook me in order to force me to pay attention.

2. Intuition: I trusted my intuition to get myself out of the mess I was in, and it was relatively seamless.

3. Transformation: This event on its own was not transformative, but it felt as though I hit rock bottom which happened to have a springboard. The true transformations I would enter were a few years away, but I was now boat-racing towards them.

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Reflect

When you sit and think back on challenging moments in your work life, are there any that feel similar? Is there a specific moment where your senses felt heightened: something that led to tears, shutting down, anger and frustration?

I’m not simply talking about chronic stress, though that is often what creates the environment for such an event to occur. But a visceral, painful memory.

This could have been a layoff (to you or others), being spoken down to by superiors, or just a moment when the overwhelm felt so intensely strong that you had to let loose in some manner.

If you can recall and revisit it now, is it something you were aware of at the time? Or was it just “another day” and something you trivialized? Can you sit with it now and understand it?

Do you still operate in an environment where such an event is likely to occur again if something does not change?

Human Connection

I have wondered what it was exactly about that moment in the office that caused me to shutdown. The stimuli that day were not negative, but neutral to positive.

But then it hit me. It was the eye contact and smile from someone that I didn’t know well. I don’t even remember the person’s name. But this person seemed at peace and calm in this moment.

For me, it was the biggest reminder of the sacrifices I was making. True human connection. Don’t get me wrong, I developed good friends from this period.

But my life was not consciously being designed to cultivate connection. It was stifling it.

Those are no longer conditions that I can find acceptable.

The time period here is roughly November of 2018, when I was living in Mexico City working for Uber. This was by far the most difficult year for me professionally. It is the only time where my stress levels were at a constant 10/10.

Humans are funny. Oftentimes, we are far less kind to ourselves than the people around us. We have periods in life where we treat ourselves poorly, or speak quite harshly to ourselves. This was a period where my inner world was quite dark and negative.

I wrote the following in one pass with zero edits. When I re-read it a few weeks later, it still felt right. If I was back in 2018, this reads as the message I wish someone could have delivered to me.

Dear Dylan,

I know you’re struggling right now. It’s ok. You’re not taking care of your body, your mind or your heart. You feel overwhelmed, stuck and alone.

But there’s a few things you should know.

1. More than anything, this will pass. And it will pass much sooner than you think. It will get better in a matter of weeks. In a few months, it will feel like ancient history. Once you reach that future state, nothing you’re experiencing now will be an issue.

2. You’re learning so much. You don’t even understand the lesson right now, but you will. In 7 years from now you’ll begin writing about this experience and it will feel cathartic. It may even help other people. You will be on a path where you are properly prioritizing your own joy and pursuing things that feel right for you.

3. You were in an impossible situation. You were asked to do something that stretched your comfort zone too much, too far and too quickly. You had no proper leadership or mentorship to help guide you. You had no resources. You were a one-person team doing the work that required 5, maybe 10 people.

4. This was the first (and truthfully only) time where you felt truly in over your head. This is not a period that has ended up repeating itself. Your feelings of stress, frustration, hopelessness and overwhelm are completely legitimate, but they will not repeat themselves to this extent again.

5. But this experience has made you more resilient and has helped you calibrate to handle future stressors and more challenging moments. Your future difficulties will definitely be difficult, but you will deal with all of them.

There will be upcoming phases of your life where you feel stuck, unmotivated or anxious about your work future. But every single time you will do what is necessary to move forward. Sometimes that will mean putting your head down for a short while and pushing through. In other times, you will step back, assess the situation, and make fundamental changes in your life for the better.

You will have no real regrets. Life is just presenting you a series of real-life curriculum to accelerate your growth. At times, you will feel as though you are failing or making the wrong choices. You’re not. You’ll never truly fail.

Trust your gut. Listen to what your body is trying to tell you. Breathe. Get good sleep. Do not sacrifice any aspect of yourself (body, mind, soul) for anyone else. Don’t sacrifice for something you think you want; if it requires one of those types of sacrifices, then it’s not what you actually want.

The path you’re on might feel like one that is chaotic and unfulfilling and wrong. But you’re early on in the journey. All you are doing right now is walking the path more commonly traveled, simply to get you moving. At some point in the future, you will exit the path, and begin creating your own path. It will be uniquely yours, but you actually won’t go it alone. There will be fellow travelers and sign posts and communal rest areas along the way to help guide you.

See you soon,

Future You

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The Moment(s) I Left My Career

2024 and 2025 are the years in which I formally ended my career, though it came in two separate events. To be transparent, I still do light freelance work with my experience and skillset (existing in NYC is not cheap!), but I no longer have an identity centered around having a career in the Tech industry.

Nowhere does this identity shift show up more prevalently than the “what do you do?” question that so often pops up in daily life. It’s become a much more exciting question to answer, as I realize I have the freedom to give a slightly different answer based on how my views of work and life are evolving moment by moment.

Threshold Event #1

In 2023 (after 4 full years in NYC) I wanted to get out of the city for a bit, so I rented a place in upstate New York for the summer.

I had already left corporate life behind me in 2020, and was helping co-run a small professional services business with a friend. But after nearly 3 years, a lot of the similar feelings surrounding lack of fulfillment were still there. It was a constant dialogue with friends and with myself about how I could just make things work.

— Could I just stick it out? What do I need to make financially? This is just a means to an end. What else would I do?

The daily stressors I faced coupled with a growing lack of passion for the work were gnawing at me every day. It felt as though the only two things I cared about long-term were the financial reward and lifestyle flexibility. Neither of these are bad desires on their own, but it wasn’t sufficient to keep me motivated.

After returning to the city in the fall, nothing really changed for me. I felt I could not prioritize my personal life, even though the work was nowhere near as demanding as it was earlier in my career. It wasn’t so much my time, but my energy being constantly depleted.

I was tired. All the time.

I knew it wasn’t because of my sleep, my diet, my physical activity, or alcohol consumption. If I had a report card on those areas of my life, I’d be getting straight A’s.

But the mental and emotional energy I was spending on work in my non-working hours was incredibly taxing. What may have seemed like an impulsive decision to the outside world was, in reality, the release of a decade of buildup.

On some normal weekday in June, I woke up and told myself, “I can’t do this anymore.” By Friday I had communicated my intention to the team, and I immediately felt great about it.

I had no immediate plan. In my session with my own coach, I let her know about the decision I had made, and she responded with a very clear, “so it sounds like you want to take a sabbatical.”

From roughly July 2024 to January 2025 I did just that. For the first time in my life, I was able to exercise just a bit of my own free will.

However, I faced a second threshold event as I was leaving that sabbatical. This moment helped crystallize things further.

Threshold Event #2

As I transitioned out of my sabbatical, I was running an experiment in returning to work in a freelance capacity. What became immediately clear to me was that the solution to my woes was not an extended break in order to return with a new mindset and a fresh mind; I was confronting the truth I was not meant to do this work.

This was my “red herring” moment.

What was interesting was that there was no specific event that occurred. The project was moving along smoothly, with normal, manageable stressors and challenges. If I were to rate the stress of the project, it was a solid 6 out of 10; right where you’d want it to be.

But in only about 3 months in, it suddenly entered my conscious thoughts:

— I just don’t wish to do this any longer.

This was a distraction. It did not inspire me. I was acting against my own nature.

I quickly slipped into previous forms of escapism in order to numb myself and pass the time. Any creative ambition I had was muted, ambitions that I would have preferred to spend on salsa dancing, writing and coaching, reading, improving my relationships, or simply enjoying life.

I simply could not be myself. Not fully. Not truly.

I made a commitment to myself and others: I would see this project through to the best of my ability. I took this on of my own choosing, and would not quit here. The end in sight was just a couple months, and I still cared about my reputation, commitments, and had pride in my work.

Oddly, that made the rest of the project more enjoyable. There was finally a means to an end in the work: it was the threshold event that would close the chapter on my first career, and springboard me into the next phase of my life.

The Takeaways

Looking back, here are 3 primary learnings I took from these events (and my career as a whole).

Lesson #1: Trust your Intuition

For at least the first half of my career, I couldn’t even name this. But I have always had a relatively strong intuition about major life decisions:

• Changing my college choice on the last possible day

• Holding out after receiving my first legitimate job offer, trusting there was something better for me

• Accepting my first counter-offer for a life-changing role without hesitation, the same day as coming to terms with my decision to reject the initial offer I had received

• 4 years later leaving Uber without a tangible plan in place

And now during these threshold moments, I fully trusted my intuition to make the best possible decision.

Lesson #2: You can be enthusiastic about work

At various points in my career I felt:

• Anxious

• Drained

• Numb

• Depressed

You may be experiencing similar feelings at this very moment.

But now for me, it has been months since I’ve felt any of these in relation to work, despite the uncertainty I currently face.

Instead, I more consistently experience:

• Curiosity

• Optimism

• Excitement

• Peace of mind

All of this is a result of prioritizing that which matters in my life, removing the distractions, and exploring something that is actually mine.

Lesson #3: Your Ego wants to keep you where you are

When I reflect on my career, there were sign posts all along the way that something was wrong. That I wasn’t where I needed to be.

2016 I experienced personal loss while feeling bored and aimless at work.

2018 was a year full of stress, overwhelm and unhealthy coping mechanisms. I wanted out. But I felt painfully stuck.

While 2019 was a good year, 2020 (surprise, surprise) brought an onslaught of negative experiences and feelings for months on end, without any sense of control.

Years later, it took me periods of rumination, soul-searching and speaking with others before I finally made my decision to take a true work break and design my sabbatical.

So why did this path take so long? Two core reasons:

1. The journey unfolds as it is meant to. The series of decisions that I made, and events that have unfolded, are life lessons. Not making changes earlier imply nothing other than not being ready yet for change. We all grow at our own pace.

2. Our Egos, the conscious persona that we have meticulously constructed since we were children, were designed to keep us where we currently are. Their most powerful tool is fear.

Although it was never conscious at the time, many of my decisions to not make a decision were born out of unnatural fears. These fears come from society, our parents, and other voices of authority we have listened to our entire lives (even if well-meaning).

Where is it that our beliefs and motivations actually come from: are these our ideas, or someone else’s?

Unraveling that tangle of influences is how we pursue a life of work that is truly meaningful and authentic.

My Life’s Work

My 2-Year Clarity Project

If you were to ask me what my life’s work will be, I don’t have an answer. All I know for certain is that what I have been doing for the past 10 years is not it. A necessary stepping stone that has now served its purpose.

Now I have a different sort of purpose:

For the next 2 years, my ultimate focus will be on seeking clarity. Clarity about:

• what work I want to produce

• the people I wish to surround myself with

• who I am and who I want to be

• the type of life I wish to build

This writing and coaching idea is just one idea I will pursue. In many ways, all I am doing is publicly sharing this clarity project, in the hopes of starting a dialogue with those on a similar journey.

My 3 Pillars

Last week, I shared the 3 foundational pillars of what my writing will be focused on. Everything I am writing about is simply a reflection of my own lived experience. That means that those 3 pillars for me show up as:

1. Beyond Work: I’ve identified the red herring of my work life, and made that final decision to create my own path. These first two posts are a true beginning.

2. Community, Relationships and Joy: With work no longer my #1 priority, I now :

   • write and reflect more

   • develop deeper relationships

   • immersed myself in new communities, such as salsa dancing

3. Sovereignty of the Mind: As I grow in other areas, I hope to dig deeper to understand my own mind and consciousness. I wish to become more mindful of my experience, and more aware of the forces at play that aim to distract and manipulate me.

My general sense is that my writing on the 3 pillars above will follow a rough 65/25/10 split. Most of what I explore initially will be about work, and ideally helping others begin that transition away from inauthentic work expression.

The work subject is the most immediate, and the most pressing matter. But ultimately, the other two are where I believe a better human existence lies for all of us.

If you’ve read this far, I hope you find some resonance with these ideas and can join me in the future to help humanity better focus on building community, deepening relationships, finding joy, and regaining agency of our minds.

I initially ended this two-part post with a Letter to my Younger Self. After reflection, I have decided that it was powerful (and vulnerable) enough to sit as a standalone piece, so I will share that next week. Until then.

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I Left Tech (and it took a while)

I’ll be honest: for the first time I don’t have a clear plan for my “career” and that excites me.

After over a decade of working in Tech, last year I made the decision to leave it behind and pursue something different. This longing to get out has been rattling around under the surface for a while.

Deep down I knew something wasn’t right: broad feelings of boredom, numbness and anxiety, and specific moments such as having a minor and (at the time) unnoticeable panic attack at work. Money and recognition and “success” simply did not compensate.

But now I’m here. And this is the first time in my life where I am pursuing something that feels like authentic and creative expression.

My aim here is to create a public-facing reflection of my inner experience, ideas, and beliefs about work, while exploring a more fulfilling existence. It is an experiment I am running for the next couple of years. It can be a failure on external measures of success, but it will only be a failure to me if I do not pursue it.

Last year I made the decision to de-prioritize “work” in order to focus on answering the following question with complete clarity:

— What is it that I most want out of this life that I was given?

Choosing to leave full-time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path.

— pg. 47 - The Pathless Path (Paul Millerd)

My Red Herring Moment

In May of last year, this thought rose to the forefront of my mind:

— The work I was doing was a red herring in my life.

The definition of a red herring, per the Cambridge Dictionary:

a fact, idea, or subject that takes people’s attention away from the central point being considered:

I remember learning about red herrings in a high school literature class, and for some reason this vivid connection was made decades later.

At that point in time, I was running another experiment after I took a sabbatical in 2024 by returning to work in a freelance capacity. Even with a more flexible style of work, it all became clear to me that the nature of the work was a distraction. I felt as though I was unable to explore and express whatever unique gifts I possessed.

As I sat with this discovery, another idea began to form:

— There are a number of talented and kind individuals who are not living in alignment with their authentic Selves through their work.

Let’s be honest — we are living in a very weird point in our history. It truly feels as though we are approaching a tipping point and that the individual and collective choices made over the next few years will be critical. And in order for us to make the choices that will construct a strong future, we need a mass realignment of people so that they may freely share their unique gifts with the world.

There is a passage in The Great Work of Your Life (inspired by the spiritual classic The Bhagavad Gita) that conveys this idea perfectly for me.

If you bring forth what is within you it will save you. Yes. But this saving is not just for you. It is for the common good. If you bring forth what is within you, it will save the world. It will rescue the times. It will save the whole people. Likewise: If you do not bring forth what is within you it will destroy you. But not just you. If you do not bring forth what is within you, it will destroy the whole people.

-- Pg. 53 - The Great Work of Your Life (Stephen Cope)

For myself, I was simply unable to “bring forth what is within me” while engaging in other forms of work. So the only solution was to leave it behind.

Removing Distractions

By taking a break from “work” and no longer making it the number one priority in my life, I have experienced (strong yet subtle) personal transformation. I believe this is possible for everyone. I know for certainty that there are others out there that have been on similar paths as mine, experiencing similar feelings of doubt, anxiety and restlessness.

This pursuit of mine is an attempt to help guide others towards a stronger sense of authentic work purpose and fulfillment.

Please do not interpret what I am saying here as me having figured out the answer to my work purpose; I’m working on that. But what I am confident in is this:

— I know exactly what my purpose in work is not.

Free Will

There’s a saying in psychology that we have to take responsibility for what we’re not responsible for.

— Pg. 45 - King, Warrior, Magician, Lover (Robert Moore & Douglas Gilette)

Many of us have been pursuing careers that are not truly of our own choosing. We were influenced by the values of our society and upbringing, reinforced by powerful economic structures and incentive models.

It is time for us to identify and accept our red herrings for what they are. By understanding how we arrived here, we can begin reclaiming our agency and a sense of free will.

But how?

The Individual’s Path

Perhaps the most powerful skill one can develop is that of awareness:

• Are we aware of what we are experiencing and feeling?

• Are we aware of why we have been unable to make meaningful change even when we desire it?

• And once we develop that awareness, do we know how to begin taking actions that are congruent with our most core desires?

The Problem Facing the Individual

After examining my own work journey, listening to friends and peers in similar situations, and observing the broader narratives expressed about work, I believe there are 3 core issues our current generation of “workers” (primarily in Tech, but also other corporate career paths) are facing:

1. There is a growing collective sense by individuals that something “just feels off”.

2. Our Egos are fighting back against these feelings, built by weaponizing societal beliefs that have been thrust upon us. Effectively, many of us have gaslit ourselves to stay in a place we are not meant to be.

3. To ultimately serve the world and tap into our unique gifts, we need to begin developing the skill in trusting our intuition to forge a more authentic path. Intuition is a superpower that we have repressed all our lives.

How did I begin addressing the problem?

I need to repeat myself. I do not have all of the answers, and I do not aim to preach. Everything I will write will be my own beliefs based on my personal experiences.

So how did I get here? Over the past decade, I began:

• Having moments where I felt something (or someone?) inside of me attempting to communicate with me, quietly yet urgently.

• Developing awareness of my work experiences and where I was headed.

• Asking myself pointed questions about my beliefs, desires and what it was that I was actually pursuing in my career (and why).

• Making significant career changes, slowly removing myself from the “normal” trajectory I was on, while managing my risk and the realities of daily living in the modern world.

When I sat to think about the decisions I have made over the last few years, I was able to bucket them into 3 core areas; going from the surface level (my external world) to what is actually going on in my own mind. I have decided to frame these as my 3 pillars for what I will write about publicly.

My Pillars

1) The Immediate: Beyond Work

For me, this meant transitioning away from Tech. More broadly speaking, this is about leaving inauthentic work behind us. It means breaking the shackles of a societal and economic system that we as individuals did not agree to.

2) The Replacement: Community, Relationships & Joy

Once we leave old forms of work behind us and not let it consume our time and energy, it is imperative that we are thoughtful about what we replace it with. We need something that “fills our cups” so to speak: engaging in community, prioritizing our relationships, and experiencing joy are three common aspects of life that many of us have sacrificed.

3) The Deep: Sovereignty of the Mind

As we shift the ways in which we spend our time and energy, how does this lead to us cultivating mindfulness and a more constant awareness of our daily, lived experience? Can we unlock our capacity to live with our eyes and ears open in every moment of life?

Initial Themes

My future writing will interweave my personal narrative with these pillars, while examining specific themes:

• Experimentation: how can we design and run experiments in all aspects of our lives to learn what fits and what doesn’t?

• Intuition: do we know how to listen to that voice within?

• Awakening & Threshold Moments: are we paying attention to critical junctures in our journeys and the signs posted for us?

• Finding Clarity: how might we get crystal clear on what we actually want in work and life?

• Transformation: and ultimately, are we willing to allow former versions of ourselves morph into a more mature, connected and authentic Self?

Why am I doing this?

For the first time in my life, this post represents a form of “work” that is authentic — something I feel called to do; something I have to do. I hope by sharing my experiences, at least one individual will find resonance in my story and can begin carving their own path.

My Commitment to You

I don’t know where my journey to find meaningful work will take me. The path I am on is very undefined, yet at the same time right.

30 years from now when I’m sixty-four, I may read this piece and smile at the naivety and immaturity of my writing and the ideas I am expressing now. But I will be incredibly thankful knowing that I took that first step, perhaps unfolding as another critical threshold moment for me!

The path I have been on the past 10 years (maybe 30 years) was not one that was going to lead to joy or fulfillment.

I might be less than 5% through my journey at this point. There is uncertainty and doubt. But I also know this: I can trust myself. I can discover out a magical future and build a unique reality for myself.

My commitment is this:

I commit to sharing my experiences and beliefs about work authentically and entirely unfiltered.

I will not produce anything that I do not believe in. I will not produce anything to feed an algorithm or to be performative.

I cannot do that. I have to do this.

Next week I will share part two about how I left.

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