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I need to stop doing this

I do not plan to start another startup. After ten years, it feels mad to say that.

Here's how this happened: I spent an hour listing out everything I cared about — from human connection, to self-education, to wealth. In the process, I surprised myself: There is a better way to achieve these goals than pursuing a startup.

The tragic part is that I could have realized this years ago. I spent three years longer than I should have pursuing the outdated dream of a startup.

So I wondered, How many other people are still working on the wrong thing too?

Let's back up. To convince myself to stop pursuing startups, I created a rubric to compare my career choices on the values I care most about today. 

I'm going to share that rubric. With it, perhaps you'll conclude you should pursue startups. (They're wonderful, but know why you're doing them.) 

Or perhaps — like me — you'll realize you've chased an outdated dream that made more sense in the past.

This is much likelier than you think. Because, when pursuing new goals, we're not abruptly thrust into overnight realizations: We don't wake up proclaiming, "I'm so inspired! I want to move to Italy, learn Italian, and become a chef! Today!"

If that's how our brains worked, we'd immediately know when to work on new things.

In reality, your current values gradually shift until they reach a tipping point where the benefits of pursuing a new thing ever-so-slightly outweigh the benefits of staying put.

With your values, you're like a frog in boiling water. It's hard to tell when to get out. 

To recognize you've reached your tipping point, periodically stop what you're doing to re-assess everything. 

That's what we'll do together in this post.

You will learn that it's not admirable to endlessly hustle with your head down. That's only commendable in the short-term. In the long term, it's a laziness — you’re riding the momentum of busywork, which blinds you to change. 

What is admirable is periodically killing your momentum to ask, Should I still be doing this?

It hurts to ask this question regularly and earnestly.

The paper that changed it all

What prompted an introspection into my values was an article revealing how Elon Musk selects what to work on. Peering into his process made me feel like an immature decision maker. 

I wondered, Is the fundamental difference between Musk and others that he's better at knowing what to spend his time on every day?

I think so. Yeah.

So I took pen to paper. I wrote down the values I cared about when choosing what to work on. My goal was to articulate how I subconsciously assess a project's worthiness.

These are the values I extracted from my brain:

It took 15 minutes to realize those are the things I care about (to varying degrees) when comparing career paths against each other.

The insane part? I didn't do this exercise until I was 27.

How irrational is that? 

In fact, almost no one I've ever spoken to has teased out and come to terms with why they do anything they do. 

They just ride the previous year's momentum.

So many years lost pursuing the wrong things...

Once you do this exercise, things becomes startlingly clear.

Specifically, the next part in the exercise was tallying up how much each career path — startups or writing guides on Julian.com — satisfied those values:

I didn't want to complicate the process by weighting each value. So I ordered the values from top to bottom in terms of what I cared about most today.

Then I placed checkmarks next to each value that the projects likely fulfilled. 

It was eye opening. The path with the most high-ranking checkmarks wasn't startups — like I thought it would be. Instead, writing was the winner. Handily.

Let me walk you through the comparison that changed my life trajectory.

First, one benefit of a startup is that it could make a lot of Money. But, making a lot of money is low on my ranking of values. 

It used to be a lot higher — when I was younger — but this exercise importantly ranked it to where it is today

For me, the remaining two benefits for pursuing startups are Adventure and Exercising Talents. 

But, Adventure is near the bottom of my list. 

Hmm. The case for pursuing a startup is thinning.

What's left is Exercising Talents. I rank that highly because it's pleasurable to be good at what you do. We're wired to enjoy putting our hard-earned skills to productive use.

What are my startup "talents" exactly? I'm good at ideating products, keeping team members motivated, and getting customers. Those are the talents I'd exercise if I pursued startups.

In contrast, if I were writing guides on Julian.com, I'd be training these talents instead: researching, critical thinking, teaching, and marketing. 

What else does writing get me? It builds an audience of readers, which helps to achieve Fame. And Fame leads to Human Connection through all the people I'm having an impact on, getting feedback from, and publicly chatting with.

And here's the thing: Human Connection is at the top of my list. 

So Writing is looking pretty good right now. It lets me exercise skills I care most about, and it really delivers on Human Connection.

But it's not yet a no-brainer to pursue writing over startups.

Until, that is, I factor in one more value: Knowledge. 

You see, writing a guide is an excuse to dive into a new interest. Throughout the coming years, I can guarantee I'll know a lot more about the world than I do now. And the frequency of topic shifting breaks my career into distinct, memorable experiences — each with new challenges. It frees you from the treadmill of work. 

And that excites me. A lot.

And, guess what? Acquiring Knowledge is ranked #2 on my values list.

And so it became clear after just 15 minutes:

I should be writing. Not starting startups.

(Judge for yourself whether my focus on guide writing was worthwhile. Here are my first two handbooks: Building Muscle and Growth Hacking. Each took 600 hours to write. They've since been read by hundreds of thousands of people.)

Again, it took 27 years to recognize that I should even sit down to spend 15 minutes on this exercise.

It's crazy to think that Musk does constantly. Although, for him, he's re-assessing technical, engineering, and economic factors — not personal values.

But the exercise equally applies: Constantly reassess why you're working on something. You'll live a higher-leverage, more fulfilling life for it.

I've only revealed a portion of what I learned from this process. Let's continue.

Wait, am I really quitting startups?

After concluding I should be writing, I wondered:

But why do I still feel the overwhelming desire to start a Startup? 

It's not like the exercise suddenly extinguished my fire to start a startup. It simply suggested I should be writing — if I could only choose one of the two to work on.

So how do I actually come to terms with that priority, though? How do I temporarily close the door on my desire for plan A so I can wholeheartedly pursue plan B?

The first step was to ask myself — and I implore you to do this too — why I honestly cherish pursuing my plan A. 

Here is my answer:

Because I don't want to die without having a huge startup success on my hands.

But, wait. Why do I even care about having startup success? 

Well, I've spent my life idolizing entrepreneurial impact. Bill Gates was my childhood answer to "Who do you want to be?"

Okay, but why do you revere that entrepreneurial impact, Julian?

I guess because I want to attain money, fame, and power. And I want to impart meaningful change onto the world.

Hold on. So those are the values guiding your decision to become a startup founder?


But, didn't you just go through an exercise where you concluded there was an alternative path that better fulfills the values you actually care most about?

Oh, right. Writing is actually better than Startups at fulfilling my values.

Hmm. So the real thing keeping me pursuing startups is momentum. The fact that that's where my career started — dogged by years of self-justification.

I need to break with that momentum. I have to deeply appreciate that writing is the more rational pursuit

Because I've likely changed over the years. I am not necessarily the person I was — the person who wanted to build a huge startup more than everything else.

But still, Julian... You can't just expect me to disassociate from my past in the course of an afternoon. 

Seriously, what framework am I supposed to use to put the past behind me, appreciate that my values have changed, and blissfully move on?

I'm glad you asked, internal dialog version of Julian. Because I recently discovered the framework you're looking for. It's called Regret Minimization:


Watch that video in full. It's only two minutes, and it's what helped me move on.

It came down to this: Determine which path you'd be more regretful not having pursued by the time you're 80 and are reflecting on your life choices.

The moment I understood I'd be more regretful if I failed to become a successful writer than a successful entrepreneur, I was no longer distracted by the urge to pursue startups. Instead, I was focused on ensuring I didn't die without becoming a successful writer. 

The clarity of that statement helped me wholeheartedly close the door to startups. 

At least for now. Because, again, the goal of this exercise is to determine what I should be doing based on my values today. That's all you can ask for.

My values will likely change again. Perhaps they’ll drift back toward startups. That’s fine. If so, that’s when I’ll start another startup. 

But not one minute before. Because every minute spent doing something other than what you love most today is a minute you’re more likely to regret when you’re 80.

Before we dive into other important learnings, let's recap:

To learn more about mental models, read my blog post.

How to do the exercise properly

I'll share are a few pointers for ordering your values rationally. I'll start by highlighting values you don't want to discount.

Staying engaged requires knowledge and challenge

The fulfilling experiences in your life are those that last. Not your weekend projects.

And sustaining your enthusiasm for a long-haul project requires at least two things: 

So be careful not to rank those low on your values list.

For reference, here again is my full list of personal values:

Why do Knowledge and Exercising Talent help keep you on a long-term track?

Because gaining knowledge leads to personal growth. And personal growth is how you avoid the dreary stagnation of most jobs. The more guides I write, the better I can navigate the world and participate meaningfully in interesting discussions.

Exercising Talents, meanwhile, allows you to stay challenged. It's what keeps you intellectually stimulated. For example, every guide I write is a newly challenging, rewarding puzzle in figuring out how to explain something complex.

In contrast, hand-making tables is unlikely to fulfill most people in the long-term. When they reach 80, they're unlikely to think, "I'm glad I made 5,000 tables in my lifetime."

However, if they made 5,000 distinct tables — drawing on various cultures, aesthetics, materials, and everyday functions — that uniquely improved the lives of those who bought them, then we're onto something.

Then they can pass the regret minimization test.

Moving on, in addition to not discounting Knowledge and Exercising Talent, I urge you to not overvalue Money.

Lessen the importance of money

Our parents' generation championed authority and physical possessions as tokens of prosperity. 

That's another way of saying they subconsciously ranked Money irrationally high.

Fortunately, our generation — the 20- and 30-year-olds reading this — trends toward prioritizing creative output and influence as success symbols. For example, many people prefer Tim Ferris' career trajectory over a Wall Street CEO's.

Why? They have an intuitive understanding of their values and are less susceptible to the old echo chamber that overvalues money.

If you're not one of those people, let me try to convert you.

Have you heard of hedonistic adaptation? It's the phenomenon where people inevitably revert to their baseline of happiness no matter how much more they earn.

Consider how, if you're already middle class, there's a fairly low ceiling for how much you must earn before earning more stops increasing your happiness. For most in the U.S., that number is around $80,000 per year.

Point being, most people would be happier earning $80,000-$150,000 from a three-day workweek than they would be hustling over-time to earn $400,000. 

Let that sink in.

Teenagers have a hard time accepting this. But, most adults eventually appreciate it.

In fact, I pursued startups for longer than I should have because they have unparalleled potential for making stupid amounts of money, and that's what I wanted.

But what's huge money really going to do for me? 

Hmm. I guess it'll help me fulfill more of the values I care about. I can spend to attain Knowledge, Fame, Power, Adventure, and so on.

But, if writing gets me more of those values right now... then what's the point of taking a decades-long detour to get to them? 

There is no point. Unless you want to start a startup for the sake of doing it — because it ranked the highest on your values exercise.

Otherwise, you should never start one primarily to make money.

You see how every major decision comes back to your ranking of values?

And here's the kicker. Until you've accomplished something deeply fulfilling, you don't realize the following: If you're already attaining the other values on your list (e.g. Adventure and Knowledge), Money rapidly becomes less interesting.

Therefore it's people who fail to attain the other values on their list that naively cling to Money; Money is a magnet for those who've never achieved fulfillment. If they felt the joy of Knowledge and Adventure, for example, they'd realize Money is just an unnecessary detour toward getting there.

So if you haven't yet savored fulfillment and my urging doesn't resonate with you, take a leap of faith: you will be happier if you stop overvaluing being megarich.

And if you want the greatest chance at realizing this for yourself, return to your values ranking: It's telling you what you should work on. Pick off the low-hanging fruit, feel that fulfillment, and let your subconscious gravitate away from Money.

You see, almost everything else you value is easier to attain than Money; everything else is low-hanging fruit in comparison.

Sure, it would be epic to have billions to do crazy Tony Stark sh!# with. But you can live an exciting and incredible life without it. If you can't figure out how to do that right now with a middle class income, don't expect to be handed the keys to happiness when you're hit with a windfall of cash. That money just keeps boredom at bay for a couple years before you revert to your baseline of happiness. The long-term value of money comes from two benefits: (1) freeing you from doing the things you don't want to do and (2) removing your financial anxiety about the future.

Hedonistic adaptation, baby. 

Lottery winners are just as miserable as they were before. 

So, I repeat, do not overvalue Money.

"In today's materialistic world, there is a risk of people becoming slaves to money. As though they were simply cogs in a huge money-making machine. This does nothing for human dialogue, dignity, freedom, and genuine well-being. Wealth should serve humanity, and not the other way around." — Dalai Lama

Beware the echo chamber

This is my final, high-level caution about ordering your values: beware people surrounding you who mislead you as to what you care about.

Because, whether you realize it or not, you're the average of the people you hang out with.

Let me paint with broad strokes to show you what I mean. Here are the types of people you might hang around:

Many others think "making the most out of life" means doing nothing more than finding a spouse, buying a home, securing a job, and raising kids.

I'm not passing judgment. The point is: Has exposure to certain people caused you to neglect what you value by adopting others' values through osmosis?

To break free from this groupthink, take a moment to identify what you would truly regret not having done by the time you're 80. 

That's the easiest way to snap yourself out of it:

Ask yourself, What would I be doing if I could start all over again?

When most people do this, they're delighted by how many things they think they care about suddenly fall by the wayside.

"I’ve noticed that many people compete in games they don’t understand because they are modeling the behavior of people around them. Most common is the competition for wealth as a proxy for happiness." — Michael Seibel

It's your turn

I'm done explaining. Go ahead and get a piece of paper.

Write out the values you passionately care about when pursuing a project.

For many, that list will include Knowledge, Adventure, Fame, Power, Money, Exercising Talent, and Human Connection. I'm certainly missing others that matter to you. That's good! My list isn't necessarily universal.

Order the values from most to least important to you today.

Next, for each project you're considering, place a checkmark beside the value that each project has a high likelihood of fulfilling. 

Based on how many checkmarks each project has, and how highly you rank the checkmarks, compare the potential fulfillment of each project. 

Don't forget to think long-term by valuing Knowledge and Exercisting Talents, and by lessening the importance of Money. 

And, quiet your anxiety during this process by appreciating that your ordering of values may change in the future. That's fine. For now, just focus on:

Which project would I most regret not having accomplished by the end of my life — in terms of the motivations I have today?

That's all you can ever do. You cannot predict your future self. So act on your present.

If this exercise fails you today, that's okay. What matters is that you establish the routine of periodic self-assessment. In doing so, your current pursuits will always remain aligned with your current values.

That's the takeaway of this post: We fundamentally change over time, but it's not obvious unless we self-assess. If we're lazy and just ride momentum, we'll regret how we spent our years when we're 80 and looking back.

And once you discover what you should truly be working on — and you can wholeheartedly justify its pursuit to yourself — there's nothing more empowering.

So far, I've written in-depth guides on how to build muscle and how to acquire customers. My upcoming guides teach how to write a screenplay, play piano, and think critically. If you'd like them a couple months early, you can enter your email below.

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