I do not plan to start another startup. It feels insane to say that.
So, here's what happened. I spent an afternoon listing out everything I cared about. Surprisingly, it became obvious that startups were no longer the best use of my time.
Writing was. And I could actually prove it.
To get to this conclusion, I had to create a rubric to compare my 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.)
Or perhaps — like me — you'll finally realize you've chased an outdated dream. A dream that made more sense for you five years ago. But not anymore.
Here's why this is much likelier than you'd reflexively think: When it comes to pursuing new life goals, we're not earnestly thrust into sudden narratives like, "I'm so inspired! I want to move to Italy, learn Italian, and become a chef!"
If our interests actually changed with such suddenness, it'd be much easier to identify when we should stop what we're currently doing.
In reality, our priorities slowly change until we reach a tipping point where the pro's of pursuing something new ever-so-slightly outweigh the pro's of what we're doing now.
It's like a frog in boiling water. It's hard to tell when it's gotten too hot. So we must periodically stop, put down our pencils, and self-assess.
That's what this post is about. Are you materially different than you used to be?
What prompted my introspection was an article detailing how Elon Musk decides 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 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 what to work on. My goal was to identify the values I use to assess the worthiness of a project:
Then I tallied up how much my two potential career paths — startups and writing guides (like I do here on Julian.com) — checked off those criteria:
It was eye opening. And I thought, why on Earth had I never done this before? Why does nearly everyone just "go with the flow" when choosing what to work on?
Anyway, I didn't want to overcomplicate the process by creating a formula for weighting each value. So I just ordered the values in terms of what I cared about most today.
I then assessed which of the two potential projects — starting another startup or writing more — had a greater likelihood of fulfilling the criteria I valued the most.
For example: One selling point of pursuing a startup is that it could make a lot of money. But, making a lot of money is low on my ordered list.
The remaining two startup pro's are then Adventure and Exercising Talents. (No matter what happens to your startup — even if you fail spectacularly — you're definitely going on a wild ride. It'll be one heck of an Adventure.)
But, Adventure isn't high on my list.
That leaves Exercising my Talents as a reason to pursue startups. I rank that highly because it's pleasurable to be good at putting your skills to use. (In contrast, pushing a dinglebop through a glumbo gets mundane fast.)
And I'm good at ideating products, keeping people motivated, and growing companies. Those are the talents I'd be exercising if I pursued a startup.
Writing guides, meanwhile, exercises three of my skills: researching, writing, and promotion.
Further, Writing Guides builds an audience of readers (Fame). Intriguingly, that audience leads to human connection through conversation and lifestyle impact.
And Human Connection is in fact at the very top of my values list.
So Writing Guides is looking pretty good right now. It lets me exercises skills I care about and delivers on Human Connection.
But it's not yet a no-brainer to pursue guides over startups.
Until, that is, I factor in one more value: Knowledge. See, every guide I write is an excuse to dive into a new topic. So, throughout the coming years, I can guarantee I'll know a lot more about the world than I do now.
That is really exciting to me.
And the frequency of that topic shifting is incredibly important to sustaining long-term interest in any project. (Context shifting breaks your life into discrete, memorable experiences where you encounter new challenges. It frees you from the treadmill.)
And, guess what? Gaining Knowledge is ranked #2 on my values list.
And so it suddenly became startlingly clear:
♖ I should be writing. Not starting startups.
It took me 30 minutes to realize this. Because, on a whim, I read an article about Musk.
And now my life is so much more fulfilling for it. It's amazing how your life can turn on a dime — if you just stop to critically assess what you care about.
We're just getting started here. I realized so much more after completing this exercise.
After concluding I should be writing, I wondered, But 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 even care about having a huge startup success?
Well, I've spent my whole life idolizing entrepreneurial impact.
Yeah, but why do you idolize that entrepreneurial impact, Julian?
I guess because I want to attain money, fame, and power. And I want to impart change.
Hold on. So those are the values underlying your decision to be a startup founder. Okay. But, didn't you just go through an exercise where you clearly concluded there was an alternative path that actually better fulfills the values you care most about?
Oh, right. Hmm. So the only thing keeping me going on startups is momentum.
I need to break that momentum. I have to put the pencil down.
And I have to confront that I've changed over the last few years. That I now have a better understanding of which values I prioritize. And I have to appreciate I've discovered a new path (writing) that fulfills those values.
But still, Julian... You've wanted to build a really big startup for since you were a kid. You can't just expect to just disassociate from your past in the course of an afternoon.
I mean, what framework are you supposed to use to put the past behind you, appreciate that your values have changed, and blissfully move on to something new?
I'm glad you asked, internal dialogue version of Julian.
Because I recently found the framework you're looking for. Regret Minimization:
Watch that in full. It's only 2 minutes long and it helped me move on.
It came down to this:
♖ The moment I understood I'd be more regretful if I failed to become a successful writer than a successful entrepreneur, I've felt no urge to pursue startups.
Here's the thing: To pursue either startups or writing in earnest requires a long-term allocation of your resources. So, if you're not the type to half-ass what you're working on, you should consider which path you'd be more regretful of not having pursued by the time you're 80 and are looking back at your life.
In the past, the answer was startups. But, today, it's writing. And darn am I thankful that I did this exercise now and not in another 2 years. That would have been 2 years I would have deeply regretted.
To repeat: We change. More often than we'd like to confront. And we don't know it until we self-assess. And delaying self-assessment leads to wasting our precious time.
But I'm still not done talking about startups. Because there's one last realization I needed to truly feel good about saying goodbye to startups: that I may change yet again in the future. As in, 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 a startup.
But not one minute before then.
Because every minute spent doing something other than what you love most now is a minute you're likely to regret when you're 80.
To perform my values listing exercise, you'll need a few pointers on how to priortize your values. Plus you'll need to break free from your groupthink conditioning.
The great projects in your life tend to be those that last for a while. And sustaining interest in something for the long-haul requires personal growth and being useful.
So, when pursuing a long-term project, never undervalue Knowledge (this leads to personal growth) or Exercising talents (this leads to being useful).
Personal growth is how you avoid the depressing stagnation associated with most jobs.
For example, writing lets me learn a lot. Fortuately, any project involving ongoing research will help you acquire a lot of knowledge.
Next, to be useful for the long-haul, you'll want to pursue a project that regularly rewards your talents. While still challenging you. For example, writing a book is a challenging and rewarding narrative puzzle. But physically handmaking artisinal paperback books is probably going to get tiring after two years.
It's this equilibrium of reward-and-challenge that allows you to maintain a flow state of stimulating mental output. It's the hallmark of Exercising your talents.
And it's how you'll never succomb to boredom.
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 dignity, freedom, and genuine well-being. Wealth should serve humanity, and not the other way around. — Dalai Lama
In addition to never undervaluing Knowledge acquisition and Exercising talent, don't overvalue Money when ordering your list.
Have you heard of hedonistic adaptation? It's the phenomenon where humans inevitably revert to their baseline of happiness no matter how much more they earn.
Consider how, if you're middle class, there's a fairly low ceiling for how much you have to earn before earning more actually stops improving your happiness. For many in the U.S., that number is $75,000 per year.
Point being, most people would be happier earning $75,000-$150,000 per year from a three-day workweek than they would hustling over-time to make $400,000 per year.
Teenagers have a very hard time accepting this. Most adults eventually appreciate it.
Failing to realize the sharply declining utility of money is what also kept me locked into startups for longer than I should have.
So, be careful not to overvalue Money when prioritizing your values list. I assure you if you're succesfully attaining the other values you prioritize (e.g. Fame and Human Connection), Money will rapidly become less interesting to you.
It's people who fail to attain these other values in life that naively cling onto Money.
And, guess what? It's usually a lot easier to attain those other values than Money.
Now for a final warning about ordering values: beware the echo chamber that surrounds you. Beware the people trying to define what making the most out of life means to you.
No one can do that for you.
This is me 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 while they have the energy to hustle.
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 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 spouse, buying a home, securing a job, and having kids.
There's nothing wrong with this. I'm not passing judgment here. The point simply is:
♖ Ask yourself, Has prolonged exposure to people who value these things overshadowed my perception of which criteria I truly value? Do I know why I care about what I care about?
To break free from the groupthink around you, take a moment to identify what you would truly regret not having done by the time you're 80. You might be surprised by what things you think you care about fall by the wayside.
Here's one trick to getting a real response out of yourself: Consider what you would do differently if you could start life all over again.
Get out a piece of paper.
Write out the values you deeply 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 universal.
Next, for each project you're considering, place a checkmark beside the value that theh project has a high likelihood of wholly fulfilling.
Based on how many checkmarks each project has, and how much you value the corresponding values, try your best to compare the aggregate worth of each project.
Throughout, appreciate that your ordering of values may change in the future. For now, 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?
And don't forget to think long-term and lessen the importance of money. Our parents' generation naively championed physical possessions and authority as symbols of successful. That's another way of saying money. Fortunately, our generation is trending toward prioritizing creative output and influence as success symbols. (For example, many prefer Tim Ferris' career trajectory over a Wall Street CEO's.)
If this exercise fails you for now, that's okay. Arguably, what matters most is that you've developed the habit of periodic self-assessment. That's how your pursuits will remain aligned with your values.
When you do discover what you should be working on — and can wholeheartedly justify pursuing it — there's nothing more empowering. Absolutely nothing.
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 well, play piano, and think critically. If you'd like them a couple months early, you can enter your email below.
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