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I need to stop doing this

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

Here's what happened. I spent an hour listing out everything I care about: human connection, self-education, wealth, and so on. In the process, I surprised myself: there's a much better way to achieve all my goals than starting another startup.

So I'm publicly sharing my framework to help others come to similar realizations: What should you really be working on?

Perhaps you'll conclude that 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Or perhaps—like me—you'll realize you've chased an outdated dream that made more sense in the past. That's the tragedy: I could have done this exercise three years ago and saved precious time. We all could, but we universally lack the discipline to halt our inertia to ask, Should I still be doing what I'm doing?

It hurts to ask this. But it changes your approach to everything.

The afternoon that changed it all

To design my framework, I took pen to paper and listed all the values I cared about. My goal was to articulate how I subconsciously assess the value of a project.

These are the values I identified:

It took 15 minutes to realize that those are the things I care about in life. What's crazy is that I didn’t do this exercise until I was 27. In 27 years, I never took 15 minutes to be more deliberate about my pursuit of... life itself.

In fact, almost no one I've ever spoken to has done this. They have no thoughtful framework for justifying anything they're doing. School didn't teach us the life planning skills that matter.

Lacking frameworks, we ride the momentum of whatever we're already doing and whatever we stumble across. You lose many years of your life when you're not deliberate.

This happens because our core values shift very slowly over time. They quietly reach a tipping point where what we're doing now is no longer the right thing to be doing for our future. It's not self-evident when this happens. We're like frogs in boiling water. We don't know when to get out.

So, let's develop a framework for periodically breaking out of life's inertia to reflect on what we should be doing today.

The Personal Values exercise

My goal was to determine whether I should pursue startups or double down on content creation at Julian.com.

Which pursuit better satisfies my values?

I ordered the values by what I care most about today. Then I drew checkmarks next to those that were fulfilled by startups and writing.

I call this the Personal Values exercise. It was eye opening: it turns out that writing has far more top-ranked checkmarks than startups do.

Here's the dialogue that played out in my head:

One benefit of startups is that they can make a lot of Money. But, making a lot of Money is low on my values ranking. It used to be a lot higher, but this exercise is about being authentic to your present self.

The remaining two startup checkmarks were Adventure and Exercising Talents. Adventure is near the bottom of my list, so that leaves Exercising Talents. I rank that highly because it's pleasurable to be a craftsperson who's good at what they do. The talents I'd be exercising at a startup include ideating products, keeping team members motivated, and acquiring customers.

Now let's turn to writing. It entails exercising different talents: researching, critical thinking, teaching, and marketing. Truthfully, those are more empowering and fascinating to me.

So let's go further. What other values does writing fulfill for me? Well, it builds an audience, which helps to achieve Fame and Human Connection through all the people I'm having an impact on. And here's the thing: Human Connection is at the top of my list. 

So writing is looking pretty good now. It empowers me to exercise the skills I care most about and it takes a direct path to my highest-ranked values.

I slept on this realization for a day.

When I woke up, however, I still had a hard time shaking this feeling: Okay, but why do I still feel the overwhelming need to start a startup? 

Wait, am I really quitting startups?

It's not as if this exercise suddenly extinguished my passion for starting a startup. It simply suggested I should prioritize writing—if I could only choose one pursuit.

How do I kill my momentum and not feel like part of my identity is being thrown into the garbage? 

Candidly, the feeling can be summed up like this:

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

My first step was to deeply confront why I want to pursue startups.

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

Alright, but why do you revere entrepreneurial impact, Julian?

I guess because I used to want Money 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?

Yes.

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

Yes. I guess I can't hide behind values as an excuse.

There must be another reason why I'm failing to move past startups. To break this strong spell, I'd need a framework for internalizing that future Julian will wish he had moved onto something else sooner.

I recently discovered that framework. It's called Regret Minimization. Revelation. Eureka.

 

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

What choices can you make today that minimize the regret you'll feel as an 80-year-old looking back on your life? When you minimize future regret, you sleep well knowing you're maximizing fulfillment.

This is the complementary framework that helps us accept the reprioritization of our interests.

The moment I understood I'd be more regretful if I failed to become a successful writer than a successful founder, I was no longer clasping onto the fading aspiration of startups. Instead, I was focused on ensuring I didn't age with maximum regret.

The startling clarity of that realization helped me close the door to startups.

At least for now.

The goal of this exercise is to determine what I should do based on my values today. My values may change again. Perhaps they’ll drift back to startups. If so, that’s when I’ll start one. 

But not one minute before.

Every minute spent doing something other than what you love most today is a minute you’ll regret when you’re 80.

Let's recap:

Running this exercise effectively

To run the Personal Values exercise, it helps to understand the meaning of your values.

For example, be careful about ordering Knowledge and Exercising Talents low on your list. They're required for sustaining enthusiasm on long-term projects: 

Personal growth via knowledge accumulation is how you avoid the intellectual stagnation of most jobs—that feeling of standing still while the world passes by. Meanwhile, being challenged is how you remain intellectually engaged—the feeling that you're playing the game of life.

These are important because success isn't an end state. Success is having the freedom to focus on the grind you actually enjoy.

For me, writing satisfies both of these objectives: Every guide I write is a new puzzle that's challenging and rewarding. The more guides I write, the better I navigate the world's knowledge and can meaningfully shape it.

In contrast, let's say I was a table maker. If I'm 80 years old looking back on how I made 5,000 nearly identical tables, I'm not going to feel like I fully realized my potential.

However, if I made 5,000 different tables—drawing on various cultures, aesthetics, and functions, then I'm following the Personal Values framework. Making these distinct tables forces me to accumulate knowledge and challenge myself anew every time.

Again, here's the list:

I'd like to caution you about another value on the list: Money. Nearly everyone gets this wrong.

Lessen the importance of money

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

If you're part of the American middle class, there's a ceiling for how much you need to earn before earning more stops increasing your happiness. For most Americans, that number is around $80,000 per year. For others, it'll be higher. In either case, no one needs $400,000 per year to find and sustain their happiness.

Meaning, most people would be far happier earning $80,000-$150,000 from a three-day workweek than they would hustling overtime to earn $400,000. 

(For many people who earn a lower income, this will be obvious. But, for people in the corporate rat race, this is not at all obvious to them.)

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

But what would huge amounts of money ultimately do for me? 

I guess it would help me fulfill more of the values I care about. I can spend money 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 turn Money back into my preferred values? 

There is no point.

In observing friends who’ve sold startups and made millions: After one year, they’re back to toying with their old side projects. They used their money to buy a nice home and eat well. That’s it. They’re otherwise back to who they were.

Point: Aim to be fulfilled—not excessively rich. There's a reason why lottery winners are just as miserable as they were before. Hedonistic adaptation is inescapable. 

Sure, it would be epic to have billions to do crazy Tony Stark stuff with. But if you can't figure out how to live a crazy, great life with a middle class income, don't expect to be handed the keys to euphoria when you're struck by a windfall of cash.

Being very rich is a magnet for those who've never achieved fulfillment. If they felt and internalized the joy of Knowledge or Adventure, they'd shortcut to optimizing for that instead.

Ultimately, people should spend way less energy trying to get super wealthy and way more energy building a tight-knit group of friends that will be with them until old age.

That said, there is of course critical importance in attaining at least a healthy baseline of income:

  1. Money frees you from doing the things you don't want to do.
  2. Money removes your financial anxiety about future stability.

In short, be thoughtful about how highly you place Money on your Personal Values list.

"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 groupthink

A final caution. The people surrounding you will distort the perception of your own values. You're the average of the people you socialize with, so if your friends are talking about startups all the time... that will seep into your brain via osmosis.

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

For everyone else, "making the most out of life" often means finding a spouse, buying a home, securing a job, and raising kids—nothing more.

I pass no judgment on any of these ambitions. I just want you to ask yourself: Has my social circle caused me to overvalue certain definitions of life's purpose? 

To break from this groupthink, ask yourself:

What would I do with my life if I could start all over again?

"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

It's time to get out a piece of paper.

Write down the values you passionately care about when pursuing projects.

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

Order those values from most to least important today.

Then, for each project you're considering, place a checkmark next to the value that it has a high likelihood of fulfilling. Don't forget to think long-term: value Knowledge and Exercising Talents while lessening the importance of Money. 

Finally, based on how many checkmarks each project has, and how highly those values are ranked, compare the potential fulfillment of each project. 

You can calm your uncertainty during this process by remembering that it's okay if your values change in the future. For now, just focus on:

Which project would I most regret not having accomplished by the time I'm 80—given the motivations I have for the foreseeable future?

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 a routine of periodic self-assessment. That's the takeaway of this post: We fundamentally change over time, but it's not obvious that we have unless we pause to self-assess. If we're lazy and just ride life's momentum, we're likely to regret how we spend our time.

Once you uncover what you should truly be doing—and you can wholeheartedly justify it to yourself—there's really nothing more empowering.

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