Welcome to another issue of The Challenge of the Month! How are you doing?

September is starting, and I’m more motivated than ever. So I’m planning to use this revamped motivation to create great things in the following months. The first one is already out. Check it out below!

There’s new premium content available this month: The AI Council — a $29 blueprint of the system I used to evaluate any idea I have and reach financial independence.

Upgrade Now

August 2026 — Life Updates

I don’t have many updates for you this month. Unfortunately, I haven’t taken a break. I worked every day. And since everyone is on holiday in Italy, I was alone most of the summer.

Also, I’ve been very committed to organizing the wedding. There are fewer than 20 days left to the big day, and I can’t wait. But I want it to be perfect, so I had to design many graphics for the tables and for the guests.

But I have to share at least one image with you. And since we used some photos from when we were young for the preparation, here’s one from when I was five years old.

Top 5 Articles of The Month

1 — More Effort Is My Default Answer

When something stops working, my first move is to do more of it. More hours, more grinding, more output. It works for a while, because effort always produces something you can point to. But then the exhaustion shows up, the results look the same as they did before I started pushing, and the crash is bigger than if I had never picked up the pace at all.

Read more

About a month ago, I panicked looking at The Challenge’s subscribers.

For three years, almost every new subscriber came from Deepstash. I repackaged each article into cards there, and the cards linked back here. But then the algorithm changed, and my main source of new subscribers died.

I’ve tried many things in the past few months. I tried different audience streams and changing the format on the old platform, thinking that was the issue. But nothing worked. And I realized the project I invested that much time in was dying.

That’s when I decided to seek help. Something had to change. I had so many projects in my mind that I couldn’t decide which to focus on, which would have been more beneficial for my financial independence. I didn’t know if I should have focused more on The Challenge or invested my time elsewhere, like in my new e-book. So I built an AI Council and let it interrogate me about my life to help me validate ideas before I invest my time in random projects.

Here’s how I did it.

How to Reach Financial Independence

This is the first message I wrote on my new project with Claude. During those past months, I thought about it a lot. And I came to the conclusion that I love writing, but I can’t keep doing this as a side hustle. I need to transform it into a financially sustainable product. Or I should find a new way to become financially independent, so I can have more time to invest in this project.

So when I started this chat, I didn’t want to limit or tell it what I hope to keep. I wanted it to assess my situation, my projects, and my financial possibilities so that we can think together about a solution later.

Here’s how the conversation started, and the five lessons I learned from it.

1 — You Have to Know Your Purpose

Usually, when you think about reaching financial independence, you imagine a number. You want to make a six-figure salary, or buy that kind of home, or that kind of car. All of these things have a value. They cost money. And that’s the first thing you consider.

But in this questionnaire, I understood that purpose matters more than that number. You want to make six figures, but why? You have to fix your purpose and envision it. Otherwise, you will never find the energy to fight long enough to reach financial independence.

When I wrote the prompt above, I got many questions to answer. I had to put a number on my financial independence. But I also had to say when I wanted to reach that, what a typical day looks like, and why I want to get out of my current job. I had to think about the reason why I didn’t want to get bored, what kind of work makes me lose track of time, and what my biggest fear was.

This gave me my direction. I wanted to do something I love, have the freedom to organize my day and decide when to work, without asking for permission.

That’s when the figure that I indicated collapsed. I found out I only needed 40% of what I already earn to leave my job and start doing it full time. I would be ready to leave my job if I could reach that on a side hustle.

Try It Yourself

• Describe your typical day in specific detail before naming any figure.

• How much does that typical day cost per month?

You found your minimum requirement for reaching financial independence.

2 — You Have to Know What You Own

I love to do many things. I love to write, build apps, and develop games. I treasure trying things out and seeing if I can make them work. On one side, that has the advantage of always learning new things. But on the other, it doesn’t allow me to deep-dive into a project and understand how to monetize it.

In this section, I shared with Claude my skills, the size of The Challenge, and the hours I can invest in my side projects to make them profitable. Answering all the questions it gave me, I understood that I could only afford about 10 hours a week, one hour every day, plus roughly two half-hours during my commute.

I also discovered that my biggest fears were only in my head.

• I assumed I couldn’t sell anything, but 70 people have already paid for this newsletter.

• I thought I couldn’t grow, but I have only tested one strategy for three years (which is now dead).

• I feared having to leave The Challenge, or stop writing, but that is the skill I trained most. That is the foundation I need for every new project I will deal with.

Try It Yourself

• Write what you have and what you’re missing in one sitting.

• Put anything you’ve discounted for not making money in the first list anyway.

• Ask which asset is losing value fastest because that’s the one with a clock on it.

You found the list of assets you should focus on.

3 — You Have to Know How You’ll Fail

When I started this chat, I was pessimistic about my skills. I assumed I was bad at sending cold emails, but I have never tried that. I had an idea of building websites for small businesses, but I have never contacted a single one. And I thought I couldn’t sell anything because otherwise The Challenge would have been a hit already.

But I didn’t want to give up, so I asked:

It turns out I had concluded I was bad at something I had never once tried. I had reached a verdict without holding a trial.

But if I decide to try things first, before making any assumptions, I would gather data on how things really went. And I could use that data to improve at it because selling is a skill, and skills can be practiced.

Try It Yourself

• Ask for a constraint that would make you fail.

• Notice whether your answer is “I tried and failed” or “I never tried”.

• Don’t argue with it for twenty-four hours.

You found the weakest point in your strategy.

4 — You Have to Know Your Projects Ranking

When you’re building too many projects, there comes a moment when you need to know what to focus on. It might be because you have had too much already, and you want to give it one last shot. Or it might be because you want to use that project as a funnel for the other ones, and you realize you don’t have time to do everything at once.

For me, it was somewhere in the middle. I have worked on some projects for years. But I was always distracted by an indefinite number of side projects. I tried Medium, The Challenge on Substack, my personal blog, Substack notes, the Book Club, Notion templates, and Deepstash promotion. But I never got the chance to exploit any of them for good.

I needed to understand which project had the most potential. And only then could I focus on something else. So here’s what I asked:

From that, I discovered that I spent four years building an audience in the most crowded category on the internet while holding a skill set that earns several times more. And that’s not a failure of effort, but a targeting error.

Also, I didn’t have any kill criteria. I abandoned many projects without a strategy. I let them die quietly instead of abandoning them for a reason. So I wasn’t learning anything new from those failures.

You can’t tell whether a project is working if you have never wondered what working would look like. If you do, every quiet week feels like failure, and every busy week feels like progress. And that’s what makes you pick or abandon the wrong projects.

Try It Yourself

• Rank every open project by time-to-first-euro, not by how much you like it.

• Write one kill criterion per surviving project, with a date.

• Track everything else in a log and don’t reopen it until the date arrives.

You found your project ranking and kill criteria.

5 — You Have to Know If Everyone Agrees

Most of us start with new projects without sharing this decision with anyone. And while you’re young, that might not matter much. But when you’re older, and you have a relationship or a family, you have to discuss these things with your partner. They have to agree to support you, especially if you’ll live with lower pay and your family needs that money to survive.

Encouragement doesn’t cost the other person anything, so it’s worthless. You have to search for the terms and commitments they are open to share with you.

I assumed for years my girlfriend would support me because I know she always did. But she has done it for more than three years now. And we’re about to get married. So I had to share my ideas with her and let her decide freely whether she would support me.

When I did her part of the questionnaire, I knew her vision might not align with mine. And I was open to closing everything down because, ultimately, you have to choose what matters most.

I discovered the conditions under which she’d want me to stop, how many hours a week she could accept me being unavailable, and for how long this experiment could last. I shared with her the money I wanted to put at risk and asked for her limits. And most importantly, I learned what she needed from me so this experiment couldn’t damage us.

Try It Yourself

• Don’t ask for encouragement, but a number and a deadline.

• Give them a real veto, because permission that can't be refused isn't permission.

• Write what you agreed on and let them read it.

You found your accountability partner and terms.

The Challenge of The Week

I started this chat with Claude seeking guidance for my financial independence. But more than that, I got a system I can use to rank every project I invest my time in, and the kill criteria that tell me when to stop.

It was an introspective voyage in which I uncovered my biggest fears, my strengths, and my weaknesses. And now I have a tool that can help me understand when I’m judging out of emotional instability, and when I am doing it out of collected data.

Today, I haven’t sent my first cold email yet. I haven’t changed anything because I am fully focusing on my wedding and the honeymoon. But as soon as I get back, I know exactly what to work on. And that’s what I am going to do.

I created a skill from that conversation. It doesn’t tell me what to do. But it can tell me what I’m avoiding, which is the part I could never see.

How to Build Your Council

The AI Council PDF contains the architecture I built for my project, and it found the thing I’d been avoiding for four years. If you need help with yours, we can build it together after a 90-minutes interview.

Reply with what you’re trying to decide, and I’ll tell you what it costs.

Before You Go

You just got the whole method. Paid subscribers get the tools.

Ten productivity systems, built and ready in Notion — Eisenhower, GTD, Time Blocking, the 12-Week Year, Eat That Frog, Kanban, Bullet Journal, Ivy Lee, Seinfeld and ABC — plus my Second Brain, Digital Garden and Reading Tracker setups.

And on the first days of every month: The Challenge of the Month. Five articles from other writers worth your time, a note on what I’m doing, and one thing I’m asking you to try for the next thirty days.

None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

Life resets: what a beautiful lie.

I remember doing my life resets once every few months, a few years ago. There were some nights when I felt inspired. I would prepare a mug of tea, sit on the bed, and start listing everything I would do differently starting next Monday.

The mug of coffee would get cold, and I would still keep writing.

Wake up earlier, read more books, stop scrolling, call my parents, fix my back, eat like an adult, invest my money: those were the things I kept promising myself. And I felt better with every line I added. But that was it. I only needed to feel better for one night so that I could get back to my life as soon as I woke up the next day.

Changing is hard. It is not something you do overnight, and you can’t change your life instantly. You can go from bad to slightly better, but not from nothing to everything. That’s why making a long list of things that will change starting Monday is just a way to feel better about yourself.

Over time, abandoning all those plans makes you wonder if you ever were the person who follows through. And that thought will be hard to eradicate.

But if you look at what worked for you in the past, you’ll notice none of those things were grand gestures or big changes in your life. They were tiny habits that you started almost randomly. So this is what we’re aiming for in this article.

Seven Habits Too Small to Feel Like Progress

When you don’t know where to start, it’s impossible to get your life back together. But with these seven unimpressive habits, it gets easier. Some things won’t impress anyone. But that’s the reason they survived.

You will skip any habit that requires concentration or commitment on a bad day. But simple habits you can do even on bad days? They are a gold mine.

Here’s mine.

1 — Skip Your Phone on The First Hour

For months I’ve been giving my mornings to The 5 AM Club. I used to wake up early, wash my face with cold water or take a cold shower, and write my first thoughts of the morning in a leather notebook.

But waking up early every morning, washing yourself with cold water, and writing by hand in a notebook is not simple. It requires a lot of effort. It requires going to sleep early, missing out on social evenings with friends, and possibly wasting the relationships you built with those people. When I am 50 years old, I might consider it again. But for now, I don’t want to exchange my social life for my early productivity. That’s not going to happen. So I knew I was never going to become that person, yet.

So I switched to a faster morning routine. Now it takes around twenty minutes, and it contains three simple things:

• My phone remains in the bedroom until I’ve been awake for half an hour.

• My body does some light movement before having breakfast (I settled for 20 push-ups).

• And I write three lines with my goals for the day.

This routine helps me work better and keeps me away from my phone, which could ruin everything. If you reach for the phone at 6:50, by the time you get to work you’ve absorbed the mood of every stranger in your feed. And those moods will be so diverse you will struggle to understand yours that morning, or you will get influenced by one of them.

You haven’t chosen any of that. But you gave the first few minutes of your attention to the Internet, and it spent it however it wished.

2 — Complain on Paper Instead of Out Loud

I remember complaining to anyone I could find on my path to cool down my nerves. But that didn’t age well.

Spoken complaints get agreement. And they feel like a resolution. But they are not. Nobody interrupts you to challenge your version of events. So the story hardens exactly as you first told it, and you carry it around. Also, complaining too much keeps people away. Nobody wants to stay near negative people, so they will start avoiding you.

Written complaints solve both problems. Writing is around four times slower than talking. And in that gap, your reasoning has time to stand up.

James Pennebaker spent decades at the University of Texas to create a useful writing protocol. You spend 15 to 20 minutes a day for three or four consecutive days and write about something that bothers you. And the effects show up in mood and physical markers months later.

3 — Check Your Physical State Before Your Personal State

Before going into this, I need to state one caveat first. If something is wrong with your physical state, sleep and water are not the answers. So this habit is not a substitute for talking to a specialist.

That said, most of my I am falling apart weeks were not existential. They may have been four consecutive nights of bad sleep that made me think like that. So before I conclude that I’m failing, I checked four boring things.

• Did I sleep well?

• Have I eaten easily digestible food?

• Have I moved today?

• Have I had water since the last coffee?

If two of those are wrong, I shouldn’t think about my life problems because I would reach bad answers. Instead, I would fix those four things first, and then question my life again.

The people I know who handle pressure better aren’t tougher than everyone else. But they absorb those life hits better because their body is prepared.

4 — Change What You Read Before Anything Else

Here’s the simplest habit on this list: set aside twenty minutes before bed to read something on paper (or on an e-book reader).

I set this habit almost a year ago, and since then I have kept it consistently. I remember how miserable the first month was. I re-read the same paragraph time and time again. I fell asleep after two pages, or forgot to read for many days in a row, or completely collapsed before I even started. But I kept going mostly out of stubbornness, and somehow my body started to accept that new habit.

What surprised me the most is that I started having ideas again. I wasn’t reading anything related to The Challenge or personal growth, but those books reshaped my thinking, and new ideas kept coming my way. They were somehow related to the books I’ve been reading, but my mind was also finding ways to connect them with my newsletter.

Your information diet works like your food diet. Eat rubbish for a month, and you feel it in your body. The same way, read rubbish for a month, and you feel it in your thinking, except this is harder to notice.

5 — Start Missing Things on Purpose

I bet your calendar is full of things you agreed to when they were far away. And now that they’re getting closer, you’re starting to feel the pressure.

I know because I felt the same. Sometimes, even going out with friends became a pressure test if I had too many commitments piling up and didn’t know if I could face them.

So I decided to use a simple rule: if it isn’t an easy yes, it’s a no.

In the past, I used to tell people I would check on my calendar, or that I would probably attend their party. I was only taking time to prepare an excuse. But this way, I was only delaying an issue. And guess what? The answer I had to give became a brand new problem to deal with.

You will miss good things. Some of them will look, from the outside, like the opportunity you were waiting for. And you’ll have to sit with the fact that you let it pass. That discomfort doesn’t go away.

But you will soon realize that’s only your brain playing tricks on you. And most of the things you’ve missed weren’t worth your time, especially if you had more time to focus on what matters.

6 — Take Yourself to Dinner

Last May, my girlfriend left for a work conference, and I remained alone at home for four days. Unfortunately, most of my friends weren’t in town or had other commitments. And since I was alone on a Sunday evening, I decided to treat myself.

I picked a restaurant I’ve been meaning to try for a while, took the car, drove there, and had a tasty dinner. And since then, I’ve kept doing this every two months.

I have to admit the first ten minutes were uncomfortable. You will reach for your phone many times while waiting for the waiter, for food, or for the check. But that’s the exercise: living without any incoming signal.

Your mind starts to wander, and decisions you’ve been avoiding for months resolve themselves in minutes. You get time to think about your opinions, and there’s nobody there validating them. So you’ll think, and think again, until you reach a mature conclusion.

Spending time alone is different from being lonely, so don’t be ashamed of going to dinner without a partner. Time alone is a choice you make; being lonely is a choice someone else makes for you.

7 — Don’t Delay Messages You Might Regret

Almost nobody loses a friendship to a fight. On the contrary, fights happen all the time between friends, but we still love those people. What makes you lose a friend is eleven months of both people meaning to reach out, with nobody doing it.

I have become a passive friend in the past few years. If people wouldn’t write me, I wouldn’t reach out to them. But last year, I decided to improve on that. So I set aside a few minutes every Friday night to check in with my friends.

I always try to remember the last thing they told me that mattered to them. For example, how did your exam go? Or, is your mother feeling better?

The replies are wildly disproportionate to the effort, and I’ve built deeper relationships since then.

Relationships don’t need grand gestures. They need someone willing to go first, repeatedly, without keeping score about whose turn it was. That’s what makes them stronger.

The Challenge of The Week

It’s not like I don’t do life resets anymore. Sometimes, that trend still gets me, and I even write about it here, on The Challenge. But every time I do a life reset, I don’t expect it to last because changes that are too disruptive never do. Instead, I try to find new ways to optimize those key habits I have already built. And if anything new shows up and it works better, I may keep it.

Do that one for seven days, at the smallest size you can manage. Then, on the last day, mark if anything changed. And remember that one habit, done badly, for weeks, beats four habits that you abandon after one week.

Before You Go

You just got the whole method. Paid subscribers get the tools.

Ten productivity systems, built and ready in Notion — Eisenhower, GTD, Time Blocking, the 12-Week Year, Eat That Frog, Kanban, Bullet Journal, Ivy Lee, Seinfeld and ABC — plus my Second Brain, Digital Garden and Reading Tracker setups.

And on the first days of every month: The Challenge of the Month. Five articles from other writers worth your time, a note on what I’m doing, and one thing I’m asking you to try for the next thirty days.

None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

I have more than two hundred videos in my YouTube Watch Later list right now.

Among them:

• A three-hour game theory lecture I saved in March and haven’t opened since

• Four different explainers on the same AI workflow tool

• And a video on writing better hooks for articles that I opened many times but never got the chance to finish.

I used to think I was ambitious. That was the proof that I was serious about getting better at things. But lately, it looks more like an excuse to procrastinate a little more.

Now, I want to play a game with you.

Open whatever app holds the things you’ve saved to consume later — Notes, Kindle highlights, a bookmark folder, it doesn’t matter which. Scroll to the oldest one and check when you added it.

You probably know what you’ll find there before you look. You could effortlessly name three things you saved right now because that’s proof that you’re learning. And you love to think that you’re ambitious.

But past a certain size, that list becomes evidence you stopped learning and started searching for excuses.

Bruce Lee: The Man With 2,800 Books

After an incredible career, Bruce Lee died in 1973. And besides the films, lessons, and martial arts school, he also left a library of 2,800 books as an inheritance. In there, you could find anything, from philosophy to boxing manuals, fencing texts, psychology, self-help, and martial arts from a dozen traditions.

The visitors who saw the shelves assumed they were looking at a man who read for its own pleasure. But they were wrong.

Bruce Lee’s copies are full of margin notes, underlines, and short reactions written onto the page. He used to take notes on passages he would decide to believe on the spot, something we all do sometimes. But his notes had a different function from those we all take because they weren’t summaries. They were a promise that an idea would be tested against a specific situation, starting from the moment he discovered it.

More than 30 years later, that habit got a name in psychology.

In 2006, Peter Gollwitzer and Paschal Sheeran published a meta-analysis of 94 studies on implementation intentions, which are plans that link specific cues to actions, in the form “when X happens, I will do Y.”

Across those 94 studies, people who used implementation intentions succeeded more than those who only intended to change something. So intending without the if-then structure produced a far smaller effect.

But what is an implementation intention?

It’s not a highlighted or underlined paragraph. It’s not a summary you write at the end of the book, or an inline sentence you write to remember about it. An implementation intention is a note that involves action: “test X the next time Y happens.” Only this kind of note will survive contact reality.

Why Do You Know So Much and Use So Little?

What would you think of someone with more than 200 unwatched videos in their watch later list, or a shelf of sketched books with none of them implemented?

You will probably think they need more discipline, or better time management, or a stricter filter on what they save. But that diagnosis keeps you on the input side, which is far from the problem.

Bruce Lee had 2,800 books, and I doubt he read and implemented all of them in the short time span he lived (32 years). But if he had only read 200 books, he would have obtained a different result from us because the input was never the variable that mattered. He turned what he read into actions with a specific time and place attached. But most of what we save never gets that treatment.

In this article, you will look at six causes that are stopping you from implementing the things you consume. And hopefully, you will finally be able to invert that trend.

1 — Your saved-articles folder outgrows your finished-things folder

I know that a full folder feels like evidence of effort, but that’s just a lie you keep telling yourself. Count what’s saved against what you’ve really tested. How many articles did you bookmark, and how many have you applied? How many courses did you finish compared to those you only started? How many recipes did you save, and how many did you cook?

For most people, the save pile is much bigger than the finish pile. It’s an order of magnitude bigger. And it’s been growing every month for years without anyone noticing the ratio, only the size.

You’re not saving too much. That’s not the problem. Saving costs almost nothing, but finishing costs real time and the risk of doing it badly. And your brain will always choose the cheaper version over the expensive one.

Pick the folder where you save things, and calculate the ratio of saved and tried things. Think about that number. Is it the ratio an ambitious person would have?

2 — You can name the framework but not when you used it

What do you know about time blocking, the Eisenhower Matrix, or the last productivity idea you found convincing? Now, think about the last time you ran it.

Could you point to it on the calendar?

People can quote frameworks easily. But when you ask them about the last time they applied them, they go silent. And this is the sign that you have a lot of knowledge, but no practice at all.

Explaining a concept clearly to someone feels like using it because both actions enable the same part of your memory. But explanation and application are two separate things. One requires you to understand the words; the other requires you to survive using them. Not only that, you have to know how to use them on a good or a bad day, which is where frameworks usually die.

The next time you explain a framework to someone, stop and ask if you’ve run it in the last thirty days. If not, you don’t know it yet. You’ve only memorized its description.

3 — You buy the second book before applying the first

I bet that somewhere on your shelf or in your Kindle library there’s a book on negotiation, or investing, or public speaking, that you finished, agreed with, and never opened again. And I bet that next to it there’s a second book, on the same topic, that promises to be the one that sticks.

Buying both those books feels like progress. I know because I am a compulsive collector myself. But it has the same effect as saving the 300th video. It’s an illusion: a cheap action that produces only the feeling of moving forward.

You don’t need two books on the same topic, or at least not until you’ve tested out the first. In that first book, there are plenty of useful ideas that might need a second or third pass to land properly. But if you buy the second one right away, hoping to crack the code, you’ll never fill the gaps you’re trying to avoid. Not even a third book can close those gaps. Only practice can.

Before buying, downloading, or bookmarking anything else on a subject you’ve already got material for, apply one idea from what you already have. Then decide if you still need the second book.

4 — Your notes have no dates on them

Open your notes app and check the last entries related to something you’re trying to learn or improve.

If none of them has a timestamp, or if you’d have to dig into the metadata to find out when you wrote them, that’s a sign you’re procrastinating.

Undated notes are the mark of a system built for storage. Nobody who plans to act on a note needs to know when they wrote it. But you need a date to catch the loops that could keep spiraling in the same topic.

The same realization about your finances, health, or relationship will return every few months because you haven’t taken notes the last time. And every time it feels like new insight because you never tested those things. You don’t have experience of it.

Date your next five notes, no matter how small. In a month, check whether they are repeats of something you already figured out.

5 — You’d rather research the tool than start the work

You might often feel like you need more preparation before doing the real thing. So you might have your spreadsheet template or the app comparison thread open, trying to figure out which difficulties you might meet. But there’s a moment when this becomes avoidance. It’s when you’re choosing between three tools for a project you haven’t even started. And the chasing has already taken longer than the first hour of real work.

Toll research looks identical to work from the outside. That’s what tricks us. You’re reading, comparing, evaluating. You’re doing work, but it’s meta-work. Nobody watching would call it procrastination. But the perfect tool doesn’t give you any progress.

Set a two-tool cap on any new project you start. Then, take 20 minutes to analyze them and pick one. If that’s the wrong tool, you will find out in the future and replace it. But at least you made some progress in the meantime.

6 — You feel behind on a subject nobody asked you about

Which subjects make you feel like you’re falling behind? Behind whom and according to what deadline?

Usually, there isn’t one. Nobody assigned you a deadline for AI literacy. No client is waiting on your macroeconomics report. The pressure is self-generated. You are aiming at a finish line that doesn’t exist because nobody set it. But this means you can never cross it.

This is an infinite resource for the pattern of consuming without producing anything. If you have a deadline, you will eventually stop reading and start doing, because the deadline doesn’t accept your feelings of insecurity. But if you don’t have one, you can stay in research mode forever. And you will keep feeling responsible until you notice you’ve been preparing for two years with nobody checking on you.

Which is one topic you feel most behind on right now? Name a low-stakes way to use it publicly this week. It could be a comment, a post, or even a conversation where you take a position instead of procrastinating.

The Challenge of The Week

I still haven’t deleted the game theory lecture I saved in my Watch Later list. Last night, I watched eleven minutes of it and paused. Then I started this issue to write about why I do that.

I don’t think I will delete anything from that list. My goal never was zero unwatched videos. But I want to stop collecting more without ever watching and applying the lessons that I learn. So I created a Gems playlist where I put everything I found useful that I could watch again to gather knowledge. Also, every time I watch a video, I write one lesson I want to apply in real life that I get from it. If I can’t find anything, then I delete the video.

Now, here’s a challenge for you.

Writing this article, I realized the long list of videos was never the problem. It was the safety net I used to prove I cared about getting better, instead of getting better.

Before You Go

You just got the whole method. Paid subscribers get the tools.

Ten productivity systems, built and ready in Notion — Eisenhower, GTD, Time Blocking, the 12-Week Year, Eat That Frog, Kanban, Bullet Journal, Ivy Lee, Seinfeld and ABC — plus my Second Brain, Digital Garden and Reading Tracker setups.

And on the first days of every month: The Challenge of the Month. Five articles from other writers worth your time, a note on what I’m doing, and one thing I’m asking you to try for the next thirty days.

None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

This week’s newsletter is sponsored by Gettier.App:

Every tool you’ve tried waited for you to show up, at exactly the moment you least wanted to. Tier is an AI accountability coach that reaches out first, every day, with a message built around your actual goal and where you left off.

You never have to remember to open it. It notices when you’re drifting and says something before you’ve fully decided to stop.

30 founding spots at $49, first year included, 30-day money-back guarantee.

It’s evening, and I’m looking at eleven weeks of consistency in my writing habit. I should have closed this a few minutes ago. It’s just my Sunday night check-in before the next week comes. But I noticed a strange pattern and can’t understand why it’s happening, so I started to research it.

I see a streak on the calendar, a few crosses lining up perfectly, and then a gap. Then another streak of crosses, and another gap.

What I notice is where the gap sits. It’s not after the bad weeks where I almost give up writing. It’s after the best ones, when I was crushing it. Every hole in that grid is preceded by a run of my strongest days of the month. And the longer the run goes, the wider the hole grows.

For years, I read those gaps as a discipline problem. After so much work, I wasn’t disciplined enough to wake up on that Sunday morning, or I was too tired on that Wednesday morning. But why does this happen only after a streak? I couldn’t explain that.

Nobody wonders why they lose motivation after a failure. That one makes sense. But losing it right after making progress doesn’t make sense at all. But I discovered that mountaineers worked this out a long time ago. Apparently, on Everest, the dangerous part of the climb is the return to the foot of the mountain.

The Half of the Mountain Nobody Photographs

In 2008, an anaesthetist named Paul Firth published a study in the BMJ that analyzed 86 years of Mount Everest records. It included 14,138 climbers, from the first British expeditions in 1921 to 2006.

Firth wanted to know how many people died on the mountain, and where it happened. And what he found was incredible.

Of the 94 people who died, 53 died on the way down from the summit and only 9 on the way up. That’s 56% against 10%.

Unexpectedly, the stretch that kills people is the stretch after the goal has been achieved, when the hard part is behind them. And the explanations looked mostly physical: oxygen runs out, weather closes in, legs that have been climbing for fourteen hours stop cooperating. But guides who work at altitude describe something underneath all of that.

On the way up, every step is a decision, and climbers are mindful about each step. But on the way down, people stop being so careful. They get so used to monitoring the summit that once they reach it, they think they can take a break. And that’s what kills them.

Now, you’re probably not a climber. You might have never climbed a mountain in your life, like me. But you’re still using this principle every week.

Why Do You Lose Motivation Right After Making Progress?

People often link loss of motivation to a lack of discipline. They think the good stretch that they had was an anomaly. But forty years of research counters this thesis.

In 2005, Ayelet Fishbach and Ravi Dhar (University of Chicago and Yale) published a paper in the Journal of Consumer Research with a title that gives away the ending: Goals as Excuses or Guides. Across four studies, they found that progress toward a goal makes people more likely to act against the same goal, not less. They called it the liberating effect because it looks like progress liberates you.

In one study, they reminded some people trying to lose weight how far they’d already come toward their target. Then, as a thank-you, they offered everyone an apple or a chocolate bar. And among those who’d been reminded of their progress, 85% took the chocolate. Among those who hadn’t, only 58% did.

Nothing changed about their diet or their willpower. But somebody pointed at their progress, and that turned into a coupon for a break.

Four years later, Anirban Mukhopadhyay and Gita Johar found the condition that makes this work. They showed that people who’d resisted an impulse purchase went on to indulge afterwards, but only when the earlier restraint was silent. When people didn’t have the good behavior in their mind, the effect disappeared.

So the rebound doesn’t depend on virtue, but on the memory of it. And that means that if you’re stuck tracking your errors, you might not have any character issues at all.

Momentum is a Budget, Not a Buffer

You used to treat consistency and good runs as a protection. You think that building momentum is enough, and then the streak will develop its gravity. You may even think that the further you get, the more you have to lose, and the harder it becomes to stop.

But that’s not true.

I believed it for a long time, and I’d still defend some ideas. Momentum indeed makes the next repetition easier. That part is defensible. But it doesn’t make the next slip less likely. The streak grows, and as it grows, your expectations grow, too. They spiral out of control. So at the first possible stop, everything explodes, and a single break day can transform into a week of missed expectations.

In Japanese craft traditions, the training model doesn’t put a reward at the end of the goal. The repetition is the goal itself. So the apprentice who sharpens his knives for two years doesn’t learn anything new by doing it well.

I’m not saying this model is better or that the Western model of work hard, then treat yourself is worse. But the latter builds a currency, and the moment something becomes a currency, you will find a way to spend it.

The Five Reasons You Sabotage Yourself

Below, I collected five reasons why you keep sabotaging your daily habits. But every one of these reasons lies on the same underlying effect. The only reason I separated them is that the interruption is different each time.

1 — Progress Becomes Credit

The first reason you sabotage yourself is that you feel the progress. You do the habit, and the doing registers as movement, which feels spendable.

The eight-kilometer run doesn’t make you hungry. But it makes you think you deserve a reward for that achievement. And that’s when you break your diet by eating a sugary dessert.

Do This Instead

Decide the reward before the effort, not after. If you choose it before the habit, it’s part of your plan. If you choose it afterwards, in front of the fridge, you will lose that negotiation.

2 — Your Attention Buys Expensive Rewards

Here’s where the Mukhopadhyay and Johar find a daily form. And it goes like this.

If you’re budgeting for a purchase, you don’t have to worry about its safety as long as it stays in your mind. Keep thinking about it, and it will grow. But if you say it out loud to someone — I’ve been good at saving this month — you open yourself up to a withdrawal.

When you finally decide you’ve earned an expensive reward due to being careful for three weeks, that’s your brain finding excuses to spend. It noticed that you’ve been good at doing it, and you’ve tricked yourself into spending that money.

Do This Instead

Stop telling yourself the score. Track it somewhere you don’t look daily, and review it monthly rather than in the moment when the review can be cashed.

3 — Being Good Tomorrow Pays For Today

The worst part of all of this is that you don’t have to make progress to get a license. Many times, merely planning to make progress is enough. For example, if you decide you’ll start your diet on Monday, you will eat everything you can on Friday. You reward yourself before the diet has even started.

This is also how a single skipped day turns into three. You take a day off, and you intend to return tomorrow, but the intention itself pays for the second miss, the one that decides whether a habit survives.

Do This Instead

When you catch yourself planning for a strong start tomorrow, do the smallest version of it today instead. You only need ten minutes. But you have to spend the intention before you reward yourself for it.

4 — You Count The Hard Thing as The Goal

Let’s say you had the hard conversation you’ve been rehearsing for weeks. It goes well, and you’re satisfied. Then, you don’t send a difficult email for eight days, but it doesn’t feel like avoidance. There’s a voice in your brain that justifies that because you already did the hard thing this month. And that’s how you keep delaying that email until it becomes too late.

The difficult conversation had to serve a goal. But instead, it took its place. And the same happens with the deep study session that replaces a week of reading, or the customer call that replaces the sales process it was supposed to start.

Do This Instead

Schedule the next repetition of a hard thing right after you do it for the first time. Put it on your calendar and commit to it, or it will take weeks before reaching the same goal again.

5 — Winning Removes the Watching

Productive mornings are always followed by dead afternoons. You cleared the inbox before ten, made an important call, but by two you’re doing something that isn’t work, but it’s rest, either.

What was holding the morning together wasn’t willpower, but attention. You were watching yourself closely because the outcome was still open. But the moment it closed, the attention left, exactly as it does on the descent from a summit. It’s the climber’s problem in miniature, and that’s why the dangerous hours in your week are the ones directly after the best ones.

Do This Instead

Write the first task of your afternoon during the morning, while you’re still the person who’s paying attention. Let the good version of you set the terms for the tired one.

The Challenge of The Week

Open whatever tool you use to track your time, money, or habits. Find the big three gaps in the last six months, and look at the two weeks before each of them.

If the gaps are preceded by chaos or difficult stretches, this article isn’t your problem, and you can stop reading. But if they’re preceded by your strongest weeks, that’s not a coincidence, and it won’t fix itself with more effort.

More effort produces bigger goals. And bigger goals generate more balance to spend.

Don’t try to change anything. Just record what happens. Seeing the pairs written next to each other is most of the work because the effect doesn’t live under examination.

Now get back to your streak, and fix those tiny gaps in between.

Before You Go

You just got the whole method. Paid subscribers get the tools.

Ten productivity systems, built and ready in Notion — Eisenhower, GTD, Time Blocking, the 12-Week Year, Eat That Frog, Kanban, Bullet Journal, Ivy Lee, Seinfeld and ABC — plus my Second Brain, Digital Garden and Reading Tracker setups.

And on the first days of every month: The Challenge of the Month. Five articles from other writers worth your time, a note on what I’m doing, and one thing I’m asking you to try for the next thirty days.

None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

This week’s newsletter is sponsored by Gettier.App:

Every tool you’ve tried waited for you to show up, at exactly the moment you least wanted to. Tier is an AI accountability coach that reaches out first, every day, with a message built around your actual goal and where you left off.

You never have to remember to open it. It notices when you’re drifting and says something before you’ve fully decided to stop.

30 founding spots at $49, first year included, 30-day money-back guarantee.

It’s 8:12. I’m walking down the main corridor of my school, and I have forgotten how to walk.

Not the mechanics: those work fine. I can move my legs how I always did. But somewhere between the front gate and the stairs, walking stopped being something my body did and became something I was performing.

My arms are too stiff. My steps are too long, and then too short. I try to correct them, but it makes it even worse, because now I’m a person visibly correcting the way he walks. And I feel like people are starting to look at me dubiously.

The problem is behind me. I can feel them back there, reading me.

It took me five years to find out how many of them were actually looking.

Before the Walking, There Was the Rehearsing

The corridor was the late stage of my anxiety, but it all started with a few random sentences.

I used to think and write about conversations before I had them. I drafted four or five openers in my head during whatever class I was supposed to be following. If someone brought up the example, I’d use the second one. If they didn’t, the first one still worked.

I always believed the silence was mine to fill. And that a silence I failed to fill would go into the record under the strange one with nothing to say. So I ran the drafts and used none of them. Then, I would review the exchange for the rest of the afternoon to understand if I could improve my next prediction.

But the rehearsing moved into my body. If I was being marked on what I said, I was being marked on how I stood and how I crossed a room. So I had to think about the way I walked, too.

And it doesn’t end there. The bottom arrived when I stopped talking to people altogether. It wasn’t a dramatic decision. But I started to avoid people because of conversations that could have gone wrong.

And nothing happened. Nobody asked. I forced myself out of social interactions, thinking I would be relieved. But the weight I felt on my chest was telling the opposite.

That’s when I went looking for other people with the same problem, and I found out my behavior had a name.

Why Do I Feel Like Everyone Is Watching Me?

In 2000, Thomas Gilovich, Victoria Husted Medvec, and Kenneth Savitsky ran an experiment at Cornell that has been quietly ruining people’s excuses ever since.

They asked students to put on a T-shirt with Barry Manilow’s face across the chest — chosen because undergraduates found it maximally embarrassing — and walk into a room full of other students. Then they asked the wearer to guess how many people had noticed the face.

The wearers guessed 46%. But the actual figure was 23%.

The researchers called it the spotlight effect: we assume our appearance and our behaviour are far more noticeable to other people than they are.

Then, the researchers ran another experiment with shirts people felt good about wearing, such as Bob Marley, Martin Luther King Jr., or Jerry Seinfeld. This time, wearers predicted 48% would notice. But guess what? Only 8% did.

These numbers teach us a great lesson: people are too focused on themselves to notice you. It’s not that they are being kind about your bad moment. They aren’t looking at you at all. And even if you want them to notice, they will probably miss it even harder.

Two years earlier, the same researchers had published work on the illusion of transparency: we overestimate how much of our internal state leaks out. You feel your heart racing, the fear, and the panic. And you assume it’s showing on your face. But it mostly isn’t.

Then, in 2003, Savitsky and Gilovich found something more useful. They had people give impromptu speeches. But they revealed the illusion of transparency to some of them beforehand. That group felt less nervous and gave measurably better speeches than the group that wasn’t told.

So being informed is the only intervention people need.

And a fourth finding, from Erica Boothby, Gus Cooney, Gillian Sandstrom and Margaret Clark in 2018. After a conversation, people consistently underestimate how much the other person liked them. The researchers called it the liking gap, and it held in five-minute chats between strangers or a full academic year between roommates.

I am thinking now about those conversations I replayed in my mind all afternoon looking for the moment I lost the other person’s interest. They probably walked away from that thinking it went fine.

The Comforting Version of This Is the Useless One

When I was younger, my parents used to tell me to relax because nobody was thinking about me. They meant well, but it wasn’t useful because it’s an instruction to stop feeling something, and nobody has ever managed that on request.

The good news is there’s a better read available.

David Clark and Adrian Wells built the standard model of social anxiety around one mechanism: self-focused attention. When you believe you’re being evaluated, your attention swings inward and you start constructing a picture of how you must look from the outside. But that’s built from your internal sensations, not from experience. You feel hot, so you assume you’re visibly red. You feel scattered, so you assume you sound scattered.

You’re falling into an inward trap. While you’re monitoring yourself, you can’t take in the external evidence that would prove you wrong. The room might be full of people not looking at you, but you will always notice the one who casually glanced at you.

This means the fix is a direction to point your attention.

4 Strategies to Stop Feeling Self-Conscious

I lived with this fear for about five years. And escaping from it required lots of strength. So I would like to give you the strategies that freed me.

I collected these items from what I was reading at that time, adapting them to my feelings. So that’s what I did, in roughly this order, during my first year.

1 — Start With Eye Contact, Not Conversation

At my worst, I couldn’t hold eye contact for a full second. I always walked looking at my own feet. And I realized that wasn’t a great way to introduce myself.

So I stopped trying to fix conversations and worked on the thing underneath them. On the train to school, I’d look at one person for as long as I felt survivable and then look away. In the first week, that was under a second, and my pulse went stupid. But after three weeks, it was two seconds, and I could do it without rehearsing first.

This works because it’s the smallest thing you’re avoiding. The fear doesn’t need a conversation to be triggered, so it doesn’t need one to be tested either.

How to Practice

Tomorrow, hold eye contact with three strangers for one full second each. You don’t have to start or smile at them. Just look at them for one second, then look away. Do it for a week before you attempt anything larger.

2 — Practice on People You’ll Never See Again

The train was the right laboratory because nobody on it had a record of me.

At school, every exchange felt permanent. It went into a file that other people were keeping. On the train, the worst outcome was a stranger deciding I was odd and then getting off at their stop and never thinking about it again.

That’s the low-stakes stake where you can act without fear. And there, you can collect evidence that you’re not bad at with conversations.

Those first hours before class, or the commute minutes before you start working, are dead time you’re already spending. It’s the cheapest reps available.

How to Practice

Pick a place where you’ll never see the same people twice: a train, a queue, a gym at an odd hour. Then, start an exchange there. It doesn’t have to be a full conversation, but an exchange. For example, you could comment on the train’s delay, or the weather.

3 — Aim Your Attention at Them

There’s something I worked out by accident and only understood years later.

Somewhere on that train I started talking to a girl who was leaving the country in a few weeks. She’d won a scholarship in Sweden. I asked what she’d be studying, what she thought she’d miss, and then whether she was frightened, and we talked for almost an hour.

I never asked for her contact. I never saw her again. I don’t remember saying anything clever.

What I remember is that I barely spoke. I’d spent years believing a conversation was a performance I had to carry, and it turned out that if you get genuinely interested in someone, they do most of the work and are grateful for the chance.

Conversations become much easier when you notice attention on them is attention away from you. And if you’re curious, people have so much to say.

How to Practice

In your next conversation, focus on the other person. Ask three follow-up questions about something they said and notice their reaction. But be careful not to force questions when they’re not comfortable answering them.

4 — Let the Conversation Die

The last piece was giving up on the thing I’d been protecting.

I wanted to prevent silence no matter what, so I’d build the rehearsals every afternoon. But one day I decided to run an experiment and let conversations end badly. I let one trail off into something. I said something that landed flat, but didn’t rush to repair.

I found that a conversation dying is not an event to remember. The other person walks off and goes back to whatever they were thinking about, and they remain with a more generous account of you than the one you’re thinking of.

You already know this from the other side. Think back to a conversation last week where someone said something awkward. You almost certainly can’t retrieve one.

How to Practice

When you feel ready, let one conversation end without rescuing it. Note what happened afterwards. Note how long anyone stayed bothered. And get used to it.

One final note before the challenge.

If you push on this and it doesn’t move — if the fear is the same in month three as it was on day one — that’s different than a bias, and it’s worth talking to a professional. The spotlight effect is a measurement error. But some people are carrying more than a measurement error, and there’s no shame in the distinction.

The Challenge of The Week

I still catch it sometimes. When I walk into a room where I don’t know anyone, there’s half a second where I become aware of my arms. What changed is what I do in that time.

I used to treat it as information about the room. Now I treat it as information about me, and I go find out what someone else is up to. So here’s what I want you to try over the next seven days.

Gilovich’s students were off by half. I’d guess you’ll do worse, because you’ve had longer to practice.

I spent five years learning to walk down a corridor. The people behind me spent those years walking down it too, thinking about their own arms.

Before You Go

You just got the whole method. Paid subscribers get the tools.

Ten productivity systems, built and ready in Notion — Eisenhower, GTD, Time Blocking, the 12-Week Year, Eat That Frog, Kanban, Bullet Journal, Ivy Lee, Seinfeld and ABC — plus my Second Brain, Digital Garden and Reading Tracker setups.

And on the first days of every month: The Challenge of the Month. Five articles from other writers worth your time, a note on what I’m doing, and one thing I’m asking you to try for the next thirty days.

None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

Welcome to another issue of The Challenge of the Month! How are you doing?

I’ve been through a pretty exhausting month, as you may have noticed. My wedding is approaching, I started a big project at work, and I am trying to do my best here too. I hope you’ll enjoy this month’s issue!

Use The Challenge’s Notion templates to boost your productivity. Download them at the end of this email.

Upgrade Now

July 2026 — Life Updates

July was a month full of joy. I’ve already been to a wedding in June, and this month started with two more: my sister’s and an old friend’s.

I won’t stay here to focus on the specifics of what we did and didn’t, but I will say I haven’t had that much fun in a while. I haven’t stopped dancing for 12 hours straight. It was an incredible wedding, with incredible people, and we partied like never before.

So this month, I will keep this short. I want to take a moment to say congrats to my sister, who might read this, and wish you to have some fun this August, too.

Top 5 Articles of The Month

Here are the top five articles I read this month.

1 — Boredom Became a Delicacy

Boredom has become a delicacy. We get so used to being busy that the second nothing is happening, we reach for the phone and consume a bit more. We’re content zombies. That’s what we became. We take in enormous amounts and apply almost none of it, and the sheer volume of available content makes it hard to stop.

Read more

This week’s newsletter is sponsored by Gettier.App:

Every tool you’ve tried waited for you to show up, at exactly the moment you least wanted to. Tier is an AI accountability coach that reaches out first, every day, with a message built around your actual goal and where you left off.

You never have to remember to open it. It notices when you’re drifting and says something before you’ve fully decided to stop.

30 founding spots at $49, first year included, 30-day money-back guarantee.

The dolphin is nine feet out of the water when the whistle goes.

It’s the hottest hour of a Valencia afternoon, three years ago, and my girlfriend and I are at the Oceanogràfic with no shade and no plan for the rest of the day. Below us, a trainer in a wetsuit stands at the edge of the pool with a bucket of fresh fish at her feet. But she hasn’t touched the bucket. The dolphin is still in the air.

I watch it happen again. Whistle first, always, while the dolphin is nowhere near her. The fish arrives six or seven seconds later, once it has surfaced and swum back — a lifetime, I guess, in the arithmetic of an animal brain. For some reason, the trainer seems to be in a hurry to say something the fish can’t say fast enough.

My girlfriend asks if I want an ice cream. I say yes, and I don’t think about the whistle again for three years.

Then, on the nineteenth morning of a diet I was about to quit, I understood exactly what that woman had been doing.

Dopamine and Habit Formation: What the Whistle Was Actually Doing

Karen Pryor ran into this problem at Sea Life Park in Hawaii in the 1960s, and she did so the hard way. You cannot hand a fish to an animal that is twelve feet in the air and forty feet from your hand. By the time the dolphin has come down, surfaced, and swum back to the platform, the jump is ancient history. Something has to happen inside that gap or the animal never learns which of the fifty things it just did earned the fish.

So the trainers build a bridge. The whistle isn’t a reward — it’s a timestamp. It tells the animal, at the exact instant of the behavior, that one. The fish confirms it later. But it’s the whistle that makes the fish mean something.

Pryor wrote about it in Don’t Shoot the Dog! in 1984, when neuroscience caught up with what pet trainers had been experimenting with for more than thirty years.

Wolfram Schultz spent the late eighties and nineties recording dopamine neurons in the brains of monkeys. He expected dopamine firing when the animal got the reward. That’s what everyone assumed dopamine was: the pleasure chemical, the payout.

It isn’t.

Schultz found the neurons fire when a reward arrives unexpectedly. Give the monkey a squirt of juice out of nowhere, and the cells light up. But once the animal learns that a particular light comes on a second before the juice, the burst migrates backward in time. It moves to the light. The juice itself, now predicted, produces almost nothing. And when the light comes on, and the juice fails to arrive, the firing rate drops below the baseline. Schultz published the model in Science in 1997, together with Peter Dayan and Read Montague, and reframed the field.

Why Are You Always Failing Your Diet?

Dopamine is a teaching signal. It’s a note the brain writes to itself saying that was better than expected, do more of it. And a note has to be attached to something. The signal binds to whatever was happening in the seconds around it.

But it’s a matter of seconds, not seasons, which brings me to the sentence that ruined my diet, and possibly yours.

“It’ll pay off eventually” is a promise made to a part of your brain that has no way to receive it. The brain anticipates constantly, and that’s the whole point of Schultz’s finding. But anticipation is calibration. The burst migrates to the cue after the reward has been delivered at least once, connecting with it. On day one of a diet, there is no history. There is nothing for the signal to move to. You are asking a prediction machine to predict something it has never experienced.

And the wait is long.

Phillippa Lally’s 2010 study at University College London tracked 96 people building habits and found automaticity took anywhere from 18 to 254 days, with a median around 66. The payoff on a body-comparison change arrives well past the window that was supposed to make the behavior automatic in the first place.

I spent nineteen days cooking instead of ordering. For nineteen days, I ate my sad chicken with rice. And I heard no whistle, not even once.

How to Build a Habit Your Brain Will Pay For

The standard explanation for what happened to me is that I lack discipline. I’ve written about that explanation before, and I still think discipline can go the distance, but not forever.

The truth is that everything starts with motivation, and it lasts about a week. After that, you’re left holding two tools. One is discipline, which takes years to build, fails often, and costs something every single time you use it. The other is a reward, which is nearly free and takes about four seconds to design.

Almost everyone spends everything on the expensive tool, runs out, and concludes they’re broken. But notice which behaviors don’t have this problem.

Nobody builds a bad habit. Nobody sets a reminder to scroll, or drafts a plan to eat crackers over the sink at midnight. Bad habits arrive prepaid. And it’s because the reward lands in under a second, every time, with no effort attached.

We get the best deal in the world, and we aren’t even grateful for it. Then we turn around and design good habits like invoices: do the work now, we’ll settle up in April.

There’s a cultural fingerprint on this.

• The Japanese practice kaizen pays the increment, where the improvement itself is the unit of value.

• Western habit culture pays out on the before-and-after photo, which places the reward at the maximum possible distance from the behavior that earned it.

One of those is a training design. The other is a hope. So here are five ways to move the payment closer. And none of them require more discipline than you already have.

1 — Decide What You Get Before You Start

The reward has to be part of the plan, not an afterthought. I know it sounds like a technicality, but it’s the difference between a signal that can migrate and one that has nowhere to go.

When you decide in advance that finishing the run means twenty minutes with the good coffee and the book you’re enjoying, you’ve created something the brain can learn to anticipate. After three or four repetitions, the anticipation starts firing at the moment you put your shoes on. And that’s Schultz’s migration happening in your head, on your schedule.

But nothing happens if you improvise the reward afterward. A reward you haven’t predicted feels nice, but it teaches you nothing because there was no cue for the signal to attach to. You end up with a pleasant afternoon and the same amount of habit you started with.

Do This

Write the reward on the same line as the habit. “Twenty minutes of reading, then the second coffee.” If you can’t finish that sentence, you don’t have a habit yet. You have an intention.

2 — Build Your Whistle

The reward can’t always be immediate, but the marker can.

The marker is any act that closes the loop when the behavior ends. It’s the tick in the box. It’s the moment you can finally say done out loud.

B.J. Fogg calls this the celebration step, and it’s the most skipped instruction in his model because it feels ridiculous. To be honest, it is ridiculous, but it works anyway.

The mechanism is the whistle at the Oceanogràfic. The marker doesn’t feed you, but it timestamps the behavior so that whatever reward arrives later has something to point at. Without it, a reward that shows up twenty minutes after the fact is just a random thing that happened to you.

Suppose you’re blocking one hour in the morning for writing, before you do anything else. You’ll be astonished to notice the habit doesn’t form from writing. It forms from what you do in the minute after you stop.

Do This

Pick a physical action you will perform every time you finish the habit you want to build and make sure you can start it under a minute. Then, repeat the same action every time you finish the habit.

3 — Don’t Pay Yourself with the Currency You’re Quitting

You can’t eat chocolate as a reward for a diet. It sounds obvious when you read it, but it’s one of the most common ways people use to dismantle their progress.

The reward for a week of early mornings cannot be sleeping in. The reward for cutting your phone use cannot be an evening on your phone. Every time the payout undoes the behavior, you build a loop that gets you nowhere.

Yet, the failure is subtler than it looks because the canceling reward is almost always the most tempting available. And it’s tempting because it’s the thing the habit was built to reduce. Your brain offers it first, every time, dressed up as a well-earned exception rather than a design flaw.

But you can test each reward by asking whether it moves you toward or away from the habit. Neutral is fine, and it’s often best because a reward has no obligation to be productive. But it has an obligation not to be corrosive.

Do This

Write the reward you are about to pick. Then ask what happens if you take it every day for three months. If the answer is that the habit becomes pointless, discard it and think of something else.

4 — Move the Scoreboard Closer

Most behaviors worth building report their results on a schedule that’s useless to you. The scale reports monthly, the savings account reports annually, and the book you’re writing reports when it’s finished, which for most people is never.

Instead, you could measure something else alongside it, close enough to the behavior to do the reinforcing work. After a run, log how you slept that night. After a study block, log how much material you could recall the next morning. After a writing session, log the number of words you wrote.

This is why streak counts work as well as they do. But it’s also where they get dangerous.

A streak is a scoreboard with daily updates, which is what a long-loop behavior needs. But the moment the streak becomes the goal rather than the record, you’ll start protecting the number instead of the behavior.

I’ve done this many times. I’ve had thirty-day streaks made almost entirely of the smallest version of the thing that still counted. But now, I use another rule: the measure of progress should always be something I’d care about even without a streak. The streak is only a means for motivation.

Do This

Pick a habit and name a metric that changes within 24 hours of the behavior. Now, track that metric and check the outcome monthly, at most.

5 — Make the Habit the Only Door

In 2014, in Management Science, Katherine Milkman showcased her test on giving people an audiobook they resent putting down and making it available only at the gym. Attendance in the group rose by roughly 51%.

She called it temptation bundling, and the rule that makes it work is the restriction, not the pairing. But it only works if the reward is unavailable everywhere else. The moment people could listen to the audiobook at home, the gym stopped being the door and became the obstacle standing next to the door.

This strategy is most effective for long-term goals because of how it works. Getting fit still takes months, for example. But you can replace that delay of waiting for a result with an attached reward that lands during the behavior itself.

So when the reading list is three weeks long, and the exam is in four days, the bundle is what gets you to the desk, not the exam. The exam is too far away to be of any use to you.

Do This

Find a portable thing you look forward to consuming: a podcast, a show, or a specific drink. Attach it to one habit and make it unavailable at every other time. Then, hold the restriction for at least two weeks. Did your habit become easier to pursue?

The Challenge of The Week

Three years after Valencia, I went looking for what the trainer had been doing, and what stays with me is that she never once looked impatient. She wasn’t willing the animal into behaving. She had built a situation where the right behavior paid on the spot, and then she got it out of the way, which is far more effective than discipline.

So here’s what I want you to try this week.

On the seventh day, you’ll probably still use your motivation to work on the habit. But if you push it past the first week, you’ll notice the benefits of the reward you picked.

You might have spent years trying to become the kind of person who could learn a habit and keep it for good. It might turn out you only needed a whistle.

Before You Go

If this kind of thinking is what you came here for, there’s more on the other side.

Paid subscribers get my personal column on the first of each month — what I’m reading, what’s happening in my life, and the 5 articles from other writers worth your time — a full book breakdown whenever I finish something worth sharing, and 10 Notion templates built around the systems I cover here. None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

You type $200. You delete it. Then, you type $50.

It’s a thirty-second form. You have to insert your bank details, an amount, and a date each month. But your cursor still hovers over the box where you decide how much you will lend to a version of you that doesn’t exist yet.

It’s not a money problem. You could easily write $200, and your life won’t change a bit. But every euro you move into that account feels like it’s leaving for good, sent to someone you’ll never meet. The version of you who needs it is decades away and faceless. But the version of you sitting here wants dinner out, an exciting holiday, and a little breathing room now.

I know the pull because I’ve sat at that exact form. And I told myself I was being responsible by saving something. But I was also quietly relieved every time I made the number smaller.

We think of saving as a willpower problem: to save more, you must want less. But the people who are good at saving aren’t gritting their teeth harder than you are. They’ve done something stranger: they’ve made the future feel less like a stranger.

The Pigeon That Explains Your Empty Savings Account

In the 1970s, a psychiatrist named George Ainslie sat pigeons in front of two keys. Pecking the first got them a little food now. Pecking the second and waiting for a few minutes, got them much more.

And even if the birds could see that patience paid better, they grabbed the smaller reward anyway, again and again. The reward was too tempting for them to wait.

Ainslie conducted an experiment on pigeons. But what he found was nothing about pigeons at all. When a reward sits far in the future, we value it sensibly. As it moves closer, its pull grows disproportionate. And at one point, the closest thing crushes the farthest, even when the latter is worth more.

Later, economists called this cognitive bias hyperbolic discounting. And you can recognize it by its symptoms. It’s the snooze button you hit every morning. And it’s the $50 you decide to invest instead of $200.

Your retirement account is a distant key. Lunch is the closest one. And a brain built on the same wiring as those pigeons will reach for the near key almost every time, unless you change what the far one feels like.

Why Can’t You Just Make Yourself Save?

Common advice treats saving as a discipline problem. You can always budget harder, cut the $1 coffee, or expect you to want less. And if you’re still not saving, the logic holds: you must want to save enough that you cut what you don’t need.

But the story has a hole in it. Plenty of people who fail to save are perfectly disciplined in every other area. They hit deadlines, train for races, and run teams and businesses that depend on their follow-through. The willpower is there. But it doesn’t show up for this task.

Unfortunately, saving is not only a fight between you and your impulses. It’s a relationship between you and a person you can’t picture. And since you don’t know who that person is, for your brain, he or she is a stranger.

Your Future Self Lives In Your Brain Like a Stranger

Hal Hershfield, a psychologist at UCLA, put people in a brain scanner and asked them to think about:

• Themselves today

• Then about themselves decades from now

• Then about a stranger.

He watched the medial prefrontal cortex, a region that lights up in a particular way when you think about yourself. But when his subjects thought about their future selves, that region quieted down.

It looked less like they were thinking about themselves and more like they were thinking about someone else. And the further away the future self felt, the more the brain filed it under the other person pattern.

Then came the part that matters for your savings account.

The people whose brains held onto a sense of self when picturing the future were the ones who had saved more in real life. Hershfield called this ability future self-continuity. He noticed that feeling connected to who you’ll become predicted your saving behavior more than monthly income.

So Hershfield ran the experiment forward. Working with a virtual reality lab at Stanford, he showed people a digitally aged version of their own face in a mirror, wrinkles and all, then asked how they’d split a hypothetical windfall. In this case, the ones who had met their older selves put noticeably more toward retirement than those who saw their present faces.

This different behavior is even baked into how we speak. Economist Keith Chen found that people whose languages grammatically separate the future from the present (”it will rain tomorrow”) tend to save less than speakers of languages that treat tomorrow like today (”it will rain tomorrow”). It looks like your grammar can file the future as a foreign country, as it does your wallet.

Now, this is the science behind it. But none of this means your future self is unreachable. On the contrary, it means that maybe you don’t need more discipline. You just need an introduction.

How to Introduce Yourself to the Person You’re Saving For

All these points lead to a clear direction: you must shrink the distance between the two versions of yourself, the present and the future. And here, I will share a few strategies that you could apply to do that. So pick the two or three strategies that resonate the most, and try them out.

1 — Put a face on the stranger.

Hershfield’s people saved more the instant their older selves stopped being ideas and became faces. And today you can easily achieve the same result.

Run your photo through an aging app and look at the result until it stops being funny. Try to imagine you have already reached that moment of your life, and that you have to deal with all the issues of old age. How would you protect that person?

2 — Automate the moment of resistance.

You can’t feel the discomfort of losing money if you never see it in your account. So the best solution might be to set a standing transfer for the morning after payday.

This way, you decide what to do with that money once, and you don’t have to make the same difficult decision every month. Also, you can’t think about spending that extra money because as soon as it appears on your account, it’s already gone.

This is an approach you can apply to anything that can be automated. Don’t rely on discipline if what you’re trying to achieve can be scheduled and doesn’t require your recursive intervention.

3 — Save the raise before it arrives.

The economists Richard Thaler and Shlomo Benartzi found that people who committed in advance to save more from future raises increased their savings rates dramatically, because take-home pay never dropped.

The logic is simple. If you’re getting $2K a month and get a raise to $2.1K a month, you can transfer that extra $100 to your investment account. If you survived with that much money until today, nothing will change after the raise. And most importantly, nothing feels lost.

4 — Shrink the horizon.

Seventy is too far to love. But next year isn’t. So instead of picturing your retirement, picture yourself one year from now and name one thing that version of you will be grateful you started.

Continuity built in one-year steps is easier for the brain to hold than a leap across forty.

5 — Write to the stranger.

If you’re a thoughtful person, writing a letter from your future self back to you might be an excellent way of thinking as if you were seventy.

Write to yourself where you live, what a slow Monday morning looks like, and what you’re glad you’ve protected. Keep that letter somewhere safe, and read it from time to time, as the years go by. It will change the way you think about the future and your money.

6 — Make it identity, not arithmetic.

People hold onto habits that match who they believe they are. That’s why you should stop framing the transfer as money leaving and start framing it as something you do. You are someone who looks after the older version of yourself, and that’s the reason why you’re saving.

The Challenge of The Week

I would like to promise you’ll beat this, but it won’t be that easy. Some months, you may still open that form and nudge the number down. You might feel some relief because now you have more money to spend. But you will soon realize those couple of dollars don’t mean anything for you, while they are a big push for your future self.

You will realize it when you look at that photo of your old self. He looks tired and softened. He doesn’t have the same grip on life that you have now. So you’ll get back to that investment account.

When you type $50, you’ll remember that face. You’ll hit cancel and type $200. And you’ll feel that was a great choice.

Before You Go

If this kind of thinking is what you came here for, there’s more on the other side.

Paid subscribers get my personal column on the first of each month — what I’m reading, what’s happening in my life, and the 5 articles from other writers worth your time — a full book breakdown whenever I finish something worth sharing, and 10 Notion templates built around the systems I cover here. None of it is published anywhere else.

$5/month →

Cosmin, The Challenge

Many things happened, many things will happen in the future, but I promise I will never leave you. I will always come back to The Challenge and everything it means for many of you.

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June 2026 — Life Updates

June was a month full of things to do. And July didn’t start off well, which is why I am so late with this article. Here’s a summary of everything that happened.

The First Wedding of the Year

At the beginning of the month, I went to Bucharest for the first of four weddings I have to attend this year (including mine, which will be the last). We stayed there from Friday morning until Sunday evening.

On Saturday, we went to the municipality where our friend got married. And although it wasn’t a big party like the other wedding we’ll be attending, it was so nice to spend time with some of the best friends we could find in this world.

The real party has still to come, and it will be next year. But for now, that was enough to spend some time together and share a little bit of Romanian culture with my future wife.

The Night Inside a Bubble

On the 14th of June, it was our 6th anniversary together, our last before we got married, and our anniversary will move to the 19th of September.

For the event, my girlfriend surprised me with an air bubble for one night, where we could sleep under a sky full of stars. And since I wanted to return the favor, we had dinner at an incredible restaurant with typical northern Italian food.

The Bachelor Party

After the anniversary, I went for a four-day bachelor party for my brother-in-law. Unfortunately, I cannot say much about that: I had to sign a contract for silence with all the other members! But I think it was some of the best men-only holidays I have ever been to.

We stayed in Calp, in Spain, and every night we’ve been to Benidorm, which some of you might already know. I think we never stopped dancing during the trip. And getting back home, I think we built a bond that will never be broken.

The Racecourse Visit

Finally, at the end of June, we went to one of the biggest racecourses in northern Italy, the Ippodromo di Vinovo, specialized in horse trot races.

There’s a company here in Italy called Club Silencio that is trying to bring young people to museums and other cultural places through music evenings. And since Gaia loves horses, I immediately booked two seats when I saw this event. We visited the horses (they have more than 200), we discovered how they train, and we even saw a race.

There was a lottery that night, and Gaia even won second place. Can you guess what the prize was? Thematically enough, it was a horseshoe!

Top 5 Articles of The Month

1 — How to Push Back on Impossible Deadlines

For years, my answer to every deadline was yes. I took everything on my plate, and then I missed most of it.

Then one of my managers taught me something I wish I’d heard earlier: if you think you can’t do it, negotiate. Say you can’t. Or say that if they need this urgently, something else has to go. This piece by Marianne Bachynski puts a structure around that exact instinct.

• Most impossible deadlines are born at the moment of agreement. Scope gets underestimated, dependencies get missed, and everyone in the room senses the gap without saying it out loud.

• Bachynski borrows the if-then-else structure from code: if we commit to three months, then we cut scope, add people, or accept more risk.

• The structure swaps emotion for cause and effect. Instead of debating whether a deadline feels reasonable, you define what it requires.

• If you accept unrealistic deadlines, your team learns that pressure overrides reality, and the gap lands on them.

2 — Something You Have To Get Good At

Read more

It’s 11:40 on a Sunday in June. The draft’s been open since dinner. I’ve reread the same four paragraphs so many times that the words have lost …

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It’s the summer I turn eleven, and I don’t know a single person in this city. I didn’t realize it then, but this move — and w…

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Welcome to another issue of The Challenge of the Month! How are you doing? What did you achieve this May? What did you finish or what did you start?

I finally finished drafting my first e-book. It took me more than six months, but it’s done. I put it on my Kindle, and I’ll spend the next few months editing it. Are you ready to receive it in your inbox soon?

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May 2026 — Life Updates

In May, I pulled back from the pace I’d been running at for months. I still went to parties and events, but the relaxing kind, not the kind that leaves you more tired than when you arrived.

The Wedding Menu Tasting

Early in the month, my girlfriend and I went to taste and choose our wedding menu. I’ve rarely been treated with that much care.

They sat us at a table facing the sunset, served some of the best food I’ve ever eaten, and poured some of the best wines in Italy. The whole night, they found small ways to make us feel like the only two people there.

A few photos from that evening:

The Work Parties

The rest of the month had a social rhythm I didn’t expect.

Two colleagues threw a joint birthday party, and a few days later, I went to my company’s annual event on the latest business trends. We talked about AI all day, then the evening turned into free drinks and music.

Turns out AI and music go together far better than I would have guessed.

Top 5 Articles of The Month

1 — Boost Your Productivity with Multi-Disciplinary Knowledge

I’ve always been a little suspicious of the multipotentialite crowd. When you’re interested in everything, you usually end up good at nothing — you spread yourself so thin that nothing ever gets deep enough to matter. I still believe that. But this piece made me draw a line I’d been missing. There’s a difference between trying to master ten things and mastering one thing while knowing a little about ten others.

Read more

It’s almost midnight, and I’m lying in the dark, replaying one sentence.

You’re not really spending time with me anymore. My girlfriend sa…

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It’s autumn 1797. Samuel Taylor Coleridge is alone in a stone farmhouse in Somerset, sick with dysentery, and a doctor has just prescribed…

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It’s evening. I am on my couch with my laptop balanced on my knees and a fresh Notion page on my screen. The header reads…

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It’s somewhere on your computer right now.

Maybe it’s in your draft folder or a notes app — a piece of writing, video, or …

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It looks like these months are rushing by. March was fast and furious. And April didn’t even show up, it seems. So let’s get the most out of this May before it ends.

Make a cup of coffee. Sit somewhere comfortable. And enjoy the reading. Welcome to another issue of The Challenge of the Month!

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April 2026 — Life Updates

This year, April was full of things to do. I had to send the last of the wedding invitations (still a few missing, but most are out). I had to celebrate two Easters (one with my girlfriend’s family, and one with mine). And I tried a few wedding suits since September is around the corner. But the highlights of the month will remain the 20s style party we organized for my best friend and my Mediterranean cruise.

The 20s Style Party

On the 18th of April, I went to a 20s-style party we organized for my best friend and one of my soon-to-be best men. His girlfriend has prepared this surprise for months. We knew he had dreamed of this party for years since he attended one for another of his friends. So his 30th birthday was the perfect opportunity for that.

We were more than 20 people, all dressed up like Peaky Blinders. And I have to say I started to love that style. It suits me a lot. Here, judge yourself.

My First Mediterranean Cruise

From the 23rd to the 26th of April, I went on a cruise with my work team. Our bosses organize these meetups to bring together people from three different sites and build a more coherent team. And this time, it was incredible.

We had the all-inclusive package. We didn’t pay for anything. And we partied all day and night. I think I slept less than 20 hours over 4 nights. We attended every disco on the cruise. We danced, twerked, drank, and partied like teenagers. To be honest, I haven’t had that much fun in a while, and I’m glad I have such great colleagues.

Unfortunately, there wasn’t much time to visit Barcelona and Marseille. But I guess that’s a common issue with short cruises. Yet, here are some photos from the trip.

Top 5 Articles of The Month

1 — The Illusion of Clarity

I read something, nod along, and close the tab, thinking I got it. A few days later, someone asks me about it, I open my mouth, and out comes half a sentence and a vague hand gesture. That’s the illusion of clarity.

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It’s 11 PM on a Wednesday, and my phone lights up with a name I haven’t seen in two years.

It’s a former colleague. We worked together for almost a year…

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The idea that getting to know someone takes time is a convenient lie we tell ourselves every day.

It explains the friendships stuck on autopilot. It…

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