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How to choose what to work on

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I'm Julian. I write amazing guides.

Like Build Muscle or Build a Startup.

Julian Shapiro headshot

I should be doing something else

I do not plan to start another startup. It feels crazy to say that.

Here's what happened: I spent an afternoon listing out everything I cared about. It became obvious that startups were no longer the best use of my time. 

Writing was. 

And I could prove it.

To get to this conclusion, I had to create a rubric to compare career choices. I'm going to share that rubric. With it, perhaps you'll conclude you really should be pursuing startups. They're amazing, but you must know why you're doing them.

This post is the antidote to having your career goals defined by what other people told you to want.

Perhaps you'll conclude you've been chasing an outdated dream that made more sense for you five years ago. To put this into context: From the ages of 12 to 26, I worked, played, and dreamed startups. Throughout, starting companies was the right thing for me to be doing. 

But I changed. I developed an appreciation for new things. 

Over the last few years, you've changed too. So let's consider the implications of that. 

Let's figure out what you should be working on today.

Life is not a movie

This mini intervention is necessary because our desires don't fundamentally shift overnight. This makes it hard to recognize when they've changed. 

We like to think epiphanies suddenly thrust us into new narratives such as, "I'm so inspired! I want to move to Italy, learn Italian, and become a chef!" In reality, we slowly evolve until we reach a tipping point where the pros of pursuing something new ever-so-slightly outweigh the pros of what we're doing now.

We're oblivious when this happens — so we must periodically self-assess.

That's what this post is about.

The paper that changed it all

What prompted my introspection was a WaitButWhy post describing how Elon Musk decides what to work on. Seeing into his thought process made me feel immature and inadequate as a decision maker. 

I began to wonder, Is the fundamental difference between Musk and other people that he's much better at knowing what to spend his time on?

I think so. Yeah.

So I took pen to paper. I wrote down all the things I care about when choosing a project. Then I tallied up how much of those criteria both (1) Startups and (2) Writing Guides satisfied for me:

(Guides refers to writing in-depth guides like How to Build Muscle.)

My goal was to identify the criteria — even those of low significance — that I personally use to assess the value of a project.

Below are the long-form criteria. I asked myself, Does a project allow me to attain:

Creating a formula to weight each criterion would be going down a rabbit hole, so instead I re-wrote the list in order of which criteria I cared about the most. 

I then tried to conclude which of the two potential projects had a greater likelihood of attaining more of the criteria I valued the most.

For example: One selling point of pursuing a Startup is a chance at making a lot of money. But, making a lot of money is low on my ordered list. 

The remaining two Startup selling points for me are Adventure and Exercising Talents. As for Adventure, no matter what happens to your startup — even if you fail spectacularly — you're definitely going on a wild ride. 

But Adventure isn't high on my list either. 

Hmm.

That leaves Exercising my Talents. I rank that highly because it's pleasurable to be good at what you do and to put it to productive use. (In contrast, pushing a dinglebop through a glumbo gets mundane fast.)

As for my Startup talents, I'm good at ideating features, keeping people motivated, and marketing. Those are the talents I'd be exercising.

Writing guides, meanwhile, really only exercises two skills: writing and marketing. So that's the first knock against Writing Guides: I don't get to wear a lot of hats.

However, Writing Guides does build an audience of readers ("Fame"). Intriguingly, an audience leads to human connection through dialogue and impact. 

And Human Connection is at the very top of my list. 

So Writing Guides is looking decent right now. But it's not yet a slam dunk.

... Until you factor in one last criteria: Knowledge. Every guide I write is actually an excuse to dive into a new topic. Over the coming years, I can guarantee I'll know a lot more about the world than I do now. The frequency of that context shifting is incredibly important to sustaining long-term interest in a project. Context shifting breaks your timeline into discrete, memorable experiences where you encounter new challenges.

And, guess what? Gaining Knowledge is #2 on my criteria list.

And so it became startlingly clear:

♖ I should be writing.

As long as I can make acceptable money from it. Which so far I've proven I can: My first guide, the Science of Building Muscle, was read by enough people in its first few months (a few hundred thousand readers) that the Amazon affiliate revenue and bonus content sales financially justified my time input.

Slow down. Am I really quitting startups?

After concluding I should be Writing, I wondered, Why do I still feel the overwhelming desire to start a Startup? 

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

But wait. Why do I care about having a huge startup success? 

Well, I've spent my whole life idolizing entrepreneurial impact.

Yeah, but why do you idolize entrepreneurial impact, Julian?

I guess because I want to attain money, fame, and power.

Hold on. Didn't you just go through an exercise where you concluded there was an alternative project that gives you more of the criteria you care more about?

Oh, right. I guess I've changed over the last few years, and my criteria has been re-ordered! But still... I've wanted to build a really big startup for a long time. You can't just expect me to disassociate from my past in the course of an afternoon. I mean, what's the framework I'm supposed to use to allow me to put the past behind me, appreciate that my criteria have changed, and move on to something new?

I'm glad you asked, internal dialogue version of Julian.

The framework you're looking for is The Minimization of Regret. Put bluntly:

♖ The moment I realized I'd be much more regretful of not being a successful writer than not being a successful founder, I didn't look back.

(Jeff Bezos created this framework. Check out his video explanation.)

Here's the thing: To pursue either Startups or Writing Guides in earnest requires a long-term commitment and a conscious allocation of resources. So, if you aren't going to half-ass your choice of project, which would you be more regretful of not having devoted yourself to when you're 80 years old and looking back?

For me in the past, it would have been Startups. Today, it's Writing. 

And darn am I thankful that I did this exercise now and not in another 2 years.

We are not done, though. There is one more thought process I needed in order to move past Startups: appreciating that I may change again in the future.

It's entirely possible startups will be the best use of my time in 10 years from now. If so, that's when I'll start one. 

But not a minute before.

Because every minute spent doing something other than what you love most is a minute you'll probably regret when you're 80. I don't want to live like that.

Side note: I don't idolize people. But I do highly value the frameworks successful people use. I think they are what separate them from the rest. Hence my interest in how Musk and Bezos think.

Think long-term

Let's consider how we should order our criteria.

There are two components to sustaining interest in a project for the long-term: personal growth and being useful. 

Personal growth entails (1) acquiring knowledge through learning and (2) building new memories through adventure. This is how we avoid depression due to stagnation.

Being useful, on the other hand, entails productively putting your talents to use. You want to find something that rewards your talent while also slightly challenging you. This allows you to slip into a flow state of low-friction and high competency.

It also allows you to experience self-worth so you avoid feeling insignificant.

Lessen the importance of money

Be wary of ordering money high on your list.

If you're in the middle-class, there's a fairly low ceiling for how much you have to earn before earning even more stops improving your happiness

For many in the U.S., that number is $75,000 per year. 

Have you heard of hedonistic adaptation? It's the phenomenon where humans always revert to a baseline of happiness no matter how much more wealth they attain.

(I feel most people don't really accept this until their late 20's.)

Some people start startups with a goal of getting rich. But the truth is most people would be happier earning $75,000-$150,000 per year from a partial workweek than they would be hustling for a <1% chance at making tens of millions from a startup. 

So pursue a startup for the criteria you value other than money.

Yes, it would be awesome to have billions to do crazy Tony Stark sh!# with. But you can live an exciting and incredible life without that wealth. If you can't figure out how to do that right now, don't expect to be handed the keys to happiness when you receive a windfall of cash. That money will just keep your boredom at bay for a couple extra years before you revert to your baseline.

Beware the echo chamber

There's a final mystical factor that can't be captured by our criteria: our perspective on the world. It's what we think "making the most out of life" means. 

Here's my best attempt at painting in broad strokes:

Hustlers think that “making the most out of life” means exploiting everything around them to gain as much wealth and power as possible while they still have the energy to deal with the grind.

Artists and spiritualists don’t necessarily have a working definition of “making the most out of life,” but they strive to fully express themselves, and to connect with people and nature as profoundly as they can.

Academics think that “making the most out of life” means amassing knowledge so that they can deliver new insights and advance debate.

Entrepreneurs think “making the most out of life” means having the biggest impact on the world and making money while doing it.

Many other people think "making the most out of life" means finding a loving spouse, buying a nice home, and securing a steady job.

There's nothing wrong with any of this. I'm not passing judgment. The point is simply: 

♖ Ask yourself, Has prolonged exposure to people from these categories overwhelmed your perception of which criteria you personally value? Have you been living inside an echo chamber?

If so, take a moment to identify what you would really, truly care about when you consider what you'd most regret not doing by the time you're 80.

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

Get a piece of paper

Write out the criteria you value. Be honest with yourself. For many people, it will be Knowledge, Adventure, Fame, Power, Money, Talents, Human Connection. There will be others I'm missing that matter to you. That's good! My list isn't universal.

Deeply consider how much you care about each criterion. Then order them.

Next, for each project you're considering, place a checkmark beside the criteria that it has a decent likelihood of fulfilling. Based on how many checkmarks each project has, and how much you value those criteria, try to compare the combined value of each. 

Finally, consider which you'd most regret not having accomplished by the end of your life. (Your criteria may change in the future, but where you are today?)

It might take you a day to decide. It might take you a week. It might take you a year.

But this is a step in the right direction — the direction of periodic self-assessment.

Once you discover what you really want to do, there's nothing more empowering.

If you conclude a startup is the best thing for you to pursue — but can't find the right idea — consider starting a pet project in the interim.

I write a new piece once per week:

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Author

I'm Julian. I write amazing guides.

Like Build Muscle or Build a Startup.

Julian Shapiro headshot

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