What to do with your life

Table of Contents

I think it's possible to identify what to do with your life. There's a super quick test for it.

In my case, I will never start another startup.

What happened:

I spent an afternoon listing out everything I cared about. I was surprised to learn that there's another pursuit that achieves my goals far better than startups ever could.

Here's how to figure this out for yourself.

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Or perhaps—like me—you'll realize you've chased an outdated dream.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's the tragedy: Without self-reflection, we ride the momentum of whatever we're already doing and whatever we stumble across. That's dangerous, because it stops us from self-reflecting on how we've changed and whether we should be doing something new.

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

The afternoon that changed my life

To design my framework, I took pen to paper and listed all the values I cared about when pursuing a new project.

These are the values I identified:

It took 15 minutes to realize that those are the things I care about. 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.

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 listed above?

As a first step, I ordered those values by what I care most about today. Then I drew checkmarks next to those that were fulfilled by startups and writing

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 when I was younger and lacked true direction, 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 assessing writing. It entails exercising different talents: researching, critical thinking, teaching, and marketing. Truthfully, those are more empowering and fascinating to me.

So let's keep going. 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 the following feeling: Okay, but why do I still feel the overwhelming need to start a startup? I can't just drop that enthusiasm overnight.

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.

Here's the conundrum: I don't want to die without having a huge startup success on my hands.

To confront this powerful, lifelong momentum, I have to truly confront why I want to pursue startups in the first place.

Well, 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, when I was younger, I wanted 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? 


But, didn't you just go through an exercise where you concluded there was an alternative path—writing—that actually better fulfills the values you care about today? Even more so than startups?

Yes. I guess that's true. Writing will provide greater fulfillment than startups. This framework helped me prove that.

But I still can't shake the emotional desire to pursue startups. 

There must be an additional—emotional—reason why I'm failing to move past startups. To break out of this, I need a final framework for internalizing that future Julian will wish he had moved onto writing sooner.

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



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.

Here was the eureka moment: The moment I understood that I'd be more regretful having failed to become a successful writer than a successful startup founder, I was no longer clasping onto the fading aspiration of startups. Instead, I was focused on ensuring I aged with minimal regret.

In other words, if pursuing startups means not fully pursuing writing, disliking the harsh reality of that tradeoff is how you squash the emotional urge to do startups.

At least for today.

The goal of this exercise is to determine what I should be doing 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 likely regret when you’re 80.

Let's recap:

Our values change over time. It's not self-evident unless we self-assess. We self-assess by ordering our values and identifying which projects best satisfy the highest-ranked values.

We then use regret minimization to overcome our bias toward past ambitions.

But there's even more to it than that. Now is when things get interesting.

Running this exercise effectively

To run this Personal Values exercise, you have to understand why you value your values.

For example, be careful about ordering Knowledge and Exercising Talents low on your list. It turns out 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. Next, being challenged is how you remain intellectually engaged—the feeling that you're playing the game of life.

Without these, you quit after a couple years.

People fail to realize that career success isn't an end state. Success is simply having the freedom to focus on the ongoing grind you actually enjoy.

For me, writing satisfies both of these values: 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 reshape 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. How can you apply this to your own career?

Again, here's the list:

Next, I will caution about another value: Money. Most people order 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 an income ceiling beyond which earning more has extremely diminishing returns on 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.

Here's what I believe: Becoming very rich is appealing to people who've never actually achieved fulfillment. Had they felt and internalized the joy of Knowledge or Adventure, they'd shortcut to optimizing for that end goal instead.

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

That said, there is of course a 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 anxiety over achieving financial stability for you and the people you care about.

To summarize, be thoughtful about how highly you place Money on your Personal Values list.

Now I have one more caution I'd like to share.

Beware groupthink

It's important to remember that the people surrounding you distort the perception of your own values. Because you're the average of the people you socialize with, 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—not 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, you must ask yourself: What would I do with my life if I could start all over again?

If you don't ask yourself this question, you can't accurately identify and order your values.

"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 self.

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 years.

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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—Julian Shapiro

October 8, 2016

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