Infinite Entrepreneurship

A lot of startup founders I talk to approach entrepreneurship as a finite game. The historian James Carse coined the term in the 1980s:


The finite game of running a startup usually goes something like this:

  1. You start working on a product with the potential to change the world (or at least make you a lot of money).
  2. You raise funding from investors on this hope.
  3. You work like hell to build and grow the product to the point where it might satisfy the conditions for "winning" — typically, going public with a juicy valuation or getting acquired by another company.

And if you don't win in this way? You lose. (Unless you're Sahil Lavingia, whose investors sold their ownership back to him for $1 after the company failed to reach its revenue targets.)

The game often changes when you remove outside funding from the equation. [1] I hardly ever hear bootstrapped founders discussing aspirational goals for walking away from their businesses. They don't want to walk away. They build projects for fun on the weekends. They read "lifestyle business" books like Company of One, Start Small, Stay Small, and It Doesn't Have to Be Crazy at Work. And they experiment with work policies like never scheduling meetings and avoiding project deadlines — at least in the case of Sahil Lavingia himself (post-funding).

In other words, infinite entrepreneurs focus on ways to enjoy the process — and not just the proceeds — of running a business.

This is a mindset shift that does real work in the real world, because changing what you aim at changes what you see. It's the difference between planning to compete for first place in a long-distance foot race and deciding to become a runner. Or between training to bench press 200 pounds and deciding to become a person who's physically fit. In each case, the second approach will tend to result in much more durable and enjoyable lifestyle changes.

One of the most influential infinite entrepreneurs of our time is Scott Adams, the cartoonist behind the popular comic Dilbert. You'll probably never encounter a founder with more entrepreneurial stamina than Scott. Among the many failed ventures he names in one his books are a velcro rosin bag, a meditation guide, multiple space-themed computer games, an app for measuring people's psychic abilities, a file-transfer product, a website dedicated to crackpot ideas, an online-video sharing app, a grocery-delivery service, a manila folder product with a pouch to hold floppy disks, a service that embeds ads in online calendars, multiple restaurants, and a keypad technology for phones. There were dozens more, but he leaves those out. His comic Dilbert, he says, "started out as just one of many get-rich schemes I was willing to try."

How did Scott keep going through all of those failures? And how, for that matter, has he found the continued motivation to make new products, write new books, and reinvent himself many decades after the wild success of Dilbert? You already know the answer if you've been paying attention: by practicing infinite entrepreneurship in the form of a relentless focus on systems instead of goals. [2] But Scott himself expresses this a little more bluntly:

Goals are for losers. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal — if you reach it at all — feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. If you achieve your goal, you celebrate and feel terrific, but only until you realize you just lost the thing that gave you purpose and direction.

Yeah yeah, all of this sounds really good on paper, but the inconvenient fact is that entrepreneurship is incredibly difficult. Most businesses fail soon after starting, and many don't ever make a dime. But founders have bills to pay — and they don't have an infinity of time in which to pay them. So you might reasonably object to infinite entrepreneurship on the grounds that even if an infinite entrepreneur doesn't play the startup game in order to "win," they can still "lose" by running out of money.

But I actually find this to be the strongest case in favor of the infinite mindset. Because money isn't the essential resource that fuels entrepreneurship. Willpower is.

Yes: entrepreneurship really is one of the most difficult endeavors around. Founders don't get to just be good at the one thing they're already good at — writing or coding or sales or managing personalities, etc. They have to be proficient all around. Especially in the early days of a project. And as with any kind of career capital, developing this proficiency takes time. Often a lot of time. So an infinite mindset prepares you to put in the years of work it might take to reach the sorts of milestones that get recognized as "business success" (like generating sustainable profits).

This point about time doesn't get discussed a lot in Silicon Valley. I think the reason for this is that VCs, who exercise a lot of indirect influence over tech publications and startup culture, aren't generally interested in what it takes to become a good founder. They're interested in founders who are already good.

So founders themselves would do well to pay less attention to "startup culture" and take the long view. Infinite entrepreneurship could mean staying at your day job a while longer — or even indefinitely — before going all in on your business. It could mean reaching out to an established founder and offering unpaid services in exchange for learning how they operate. It could mean learning to ship free projects to a given audience before trying to ship paid products. [3]

But whatever you do, ignore stories about college dropouts building unicorn startups. Ignore those who insist you have to reach this or that milestone by age 30. And never take it for granted that "successful" founders featured in the news are as happy as they let on in their cover stories. I know dozens of these people personally. Hedonic adaptation ensures they're usually no happier after succeeding than they were before. And when they are, it's usually because they've found ways to keep playing.

Enjoy the read?

The "story model of purpose" is my life philosophy to a) continuously b) make progress on c) problems d) that matter to me. And this newsletter is where I'll discuss topics based on these four themes.

Infinite entrepreneurship, for example, focuses mostly on the first theme: continuity.

Drop your email below to read more thoughts in this series or to learn more about the philosophy itself:


[1] There's probably only a loose correlation between how a business is funded and which kind of game its founder plays. Many venture-backed founders land big exits and then become serial entrepreneurs, and many bootstrapped founders chase exits of their own. (After all, we sold Indie Hackers to Stripe.)

Still, I'm happy to stick with this generalization because it seems to accurately represent the value differences between people in high-growth startup circles vs people in bootstrapping circles.

[2] The systems-versus-goals mantra seems ubiquitous among entrepreneurs these days (largely thanks to the massive success of James Clear's Atomic Habits, which was partly inspired by Scott Adams), so it's worth clarifying that Scott Adams himself defined the distinction between a "system" and a "goal" this way:

For our purposes, let’s say a goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

[3] Nathan Barry's article on the ladders of wealth creation does a good job illustrating what this sort of climb might look like, both in theory and in practice.

  1. 6

    I really like this!

    A friend of mine told me to read "Finite and Infinite Games" by James P. Carse and I think what you just described is the reason. Habits-minded people are under-valued vs goal-minded people. It's hard to focus only on being able to advance steadily, vs planning to be a billion-dollar company on a spreadsheet 5 years from now.

    Like you said, VCs are in the number's game(I worked for a SaaS for VC) and their goals are very often conflicting with entrepreneurs goals.

    Systems Thinking vs Linear Thinking is mostly what differentiate Infinite Game players vs Finite Game players.

    1. 2

      I really like this!



      good advice. it gives you a new lens through which to see the world, and afterwards you notice the pattern everywhere — especially in your own life.

      i would even more strongly recommend the book i referenced from scott adams: how to fail at almost everything and still win big.

  2. 3

    Great write up, This is something I believed in but couldnt put into words. Your newsletter has earned my email address.

  3. 3

    Enjoyed the read! But my take is that there is no goal vs habit or finite vs infinite. Both are part and parcel of entrepreneurship or success in general . Goals are the very reason you work out systems. Both are infinite.

    I can understand the point about being goal-orientated and then losing steam after achieving it. But that is because the goals were numeric or finite in numbers.

    Goals should not be a finite game. But milestones to achieve that goal is. And as you hit milestones after milestones, it becomes a habit. That habit constitutes a system you have created for consistency.
    E.g. Goal is - To achieve financial freedom. You set specific milestones /targets and create new ones after you hit them. And when you consistently acheive them or is in a mindset towards this, it slowly becomes a systematic habit. Habits become part of you.

    Or another example, your goal is to be the fittest version of you. Then you set milestones like doing how many bench presses, eating a certain way. Consistently doing this, it becomes a habit. You have a system in place now to be the fit. That's my take on this. :)

    1. 4


      well said. i agree actually. it's the problem of trying to categorize a continuum: every founder engages each category at some point, just not in the same amounts or for the same lengths of time.

      but as i mentioned in the article, changing your aim changes your vision. sure: we all have goals and systems. but i know people who place 95% of their focus on goals and only 5% of their focus on systems. and their moods, professional outputs, and lifestyles tend to be highly unstable as a result.


      there's one nuance here that bears mentioning, which is that this virtuous cycle spins up much more quickly when you are able to break your goals down into daily, highly controllable inputs and then iterate on them over time.

      for example, if this article had flopped i might have had a few brief moments of disappointment, but they would have been relatively minor given that i place most of my focus on a daily goal to write for at least half an hour.

      another article (whose reception i can't control) will come in a few weeks, then another after that. but meanwhile, behind the scenes, i'll be celebrating a hundred tiny wins that will sustain me for decades to come if i live to see them.

  4. 2

    Really good post! Thank you!

  5. 2

    just let you know, Wangxing, the founded of Meituan, also likes this book a lot, and practiced this infinite game concept to create Meituan, one of the largest unicorns in China. Meituan is not his first successful startup, previously, he created Fanfou, and Xiaonei. Therefore, this infinite game concept may also applies to serial entrepreneurship?

  6. 2

    Nicely written. I have been heavily influenced by Scott Adams, Naval Ravikant and DHH. All three of them give out advice for free (without selling you anything).

    In a world full of self acclaimed business gurus and growth hack strategists my way of filtering advice is to only pick folks who genuinely do it because they want to. They have already made it, have f you money and pursue the next goal of helping out other folks who want to listen to them.

  7. 2

    I totally agree with the main idea of the post, you need to learn to enjoy the journey, and not be blinded by the idea of the destination.

    Still, I think there is one dimension commonly overlooked: the criteria to rate the game. You can become a serial entrepreneur that cares about the infinite game and still be a perfect idiot, taking all the credit for yourself, not caring about the social impact of the projects you are involved with or the people you meet along the way and how this deeply change their lives.

    I feel many entrepreneurs are following that line, happy people that just ignore bad vibes around them because that makes them less productive, I know it is harder to work that way because a lot new variables come into play and I know about the mantra "Make it happen", focus on how to get things done, but I feel often the long term cost is too high. I wish that a well-respected and successful entrepreneur start discussing this openly because that way others will follow.

    1. 1

      i agree it's important for individuals to consider the externalities of their actions, but i'm a strong advocate of what steven covey (author of the 7 habits of highly effective people) calls the inside-out approach: first, you learn how to be personally effective, then you learn how to utilize that effectiveness to serve increasingly wider circles around you. personal success (however someone defines it) isn't an abundant resource, and freighting your path with a bunch of social-impact criteria for building toward success can be self-defeating.

      in another words, i'm an advocate of baby steps.

      i have a friend who told me she was struggling to get her new art photography business off the ground. it turns out, she insisted on sharing revenue with each of her photographic subjects (all of whom were happy volunteers) out of a sense of moral duty. yet: she had no incoming revenue, no outside capital, no distribution plan, and hardly any free time (she was doing this on the side of her full-time job).

      it's good to feed your family, but the first and most difficult step is to learn to feed yourself.

      1. 2

        I am afraid I didn't explain myself right, I totally agree with you in those points, but that is not what I was talking about.

        I think the metric/rate function is often taken for granted, but it is not. When building a product it is advised to validate, that is, instead of assuming what your users want, go ahead and give it to real users to learn from them. In the same way, a reality check must be defined externally (not an externality though), we are subjective by design and we cannot remain objective about what our goals were at the beginning, it is good to be ambitious and to evolve as we are going, but even if I think the infinite game is a nice approach I don't think an infinite ambition is healthy, not for the individual nor for the society.

        I am glad you brought the example about your friend, I totally agree with you on the advice. My point there would be, once it is producing steady revenue it is time to reality check and give back to the community, not as starting a new idea to always have a wider circle of happy volunteers (it turns out they'll be willing to continue as happy volunteers even if you now have some profit) but as re-adjusting the model for this new reality.

        Again, I agree about first feeding yourself, but I am afraid more than one entrepreneur is getting a bit fat instead of just feeding, it is a personal decision to say when it is enough, but that doesn't make being overweight a myth.

  8. 2

    You've earned yourself a newsletter subscriber! Really enjoyed reading this and I can't wait to share it with my students.

    1. 1

      thrilled to hear that — thanks!

  9. 2

    Simon Sinek has a great book called The Infinite Game on this topic. Great read. I highly recommend it to anyone interested in this idea.

  10. 2

    Thanks for the post, really inspiring!!!

  11. 2

    Great article Channing! Thank you for writing this philosophical article. For me, I’m conflicted between the two kinds of games.

    On one hand, Finite entrepreneurship = build a number value-based business to pay bills, build wealth, and sustain/grow income for a given lifestyle (single, family, etc.). This is my day job and how I can provide for myself and others.

    On the other hand, Infinite entrepreneurship = build a human values-based business to have a business (civilization) worth passing on. This is what I would like to relentlessly focus on to replace my day job long term. However, I’m a rookie in terms of building and selling.

    I’ve been thinking a lot about starting a business based on with values (numbers) vs starting with human values after watching the Eco SXSW Keynote by William McDonough on YouTube (see video link below). McDonough said, “If you start with value, or number, all you can do is benchmark. You don't get to your values from value. You can't get to your human values from a number. You can get the number from your values. So we (cradle to cradle) like to start with, “What is right? What is wrong? What is good? What is bad?” And less and more (numbers) come later.”

    I thought this connects well to your point of hedonic adaptation. If founders are following numbers first, or people in general, shouldn’t we take the advice to follow our human values towards happiness and an enjoyable lifestyle?


    1. 2

      For those who are interested, start the video at 16:00 where he begins to discuss the human values vs number values topic I referred to.

    2. 1

      cool perspective!

      the way i see it, there are two separate dimensions: a) what you work on, and b) how you work. the first connects to your goals, but the second connects to your day-to-day processes.

      you spoke a lot about the first — whether you're working on something that makes you money vs. something that makes the world better. i certainly agree that it's worth charting a course to building something that makes the world better. but even if you manage to do this, it helps to have a daily system in place to keep you motivated and moving in the right direction, which is what i mean by infinite entrepreneurship.

      1. 2

        Would it be valid to say that infinite entrepreneurship, in this case, could look like taking a long-term view on the passion project and remaining determined to chip away at it while also creating enterprises that generate more immediate numbers?

        1. 1

          100%. but you're not merely generating financial capital with those earlier ventures — you're also generating intellectual and career capital. in other words, you're transforming yourself into the kind of person who will excel at the passion project or a number of other projects.

          it's a win win: but it takes the patience and grit of a long-term thinker.

          highly recommend so good they can't ignore you by cal newport if you want to dig into this area deeper.

  12. 2

    It's very humbling to archive some personal goals - and realise things don't change at all. Instead, enjoy the process.

    Thank you for the awesome post!

    1. 2

      thanks for reading! a really big key is realizing that this doesn't only apply to small personal goals but also to very large personal goals. it becomes really hard not to restructure your life when you internalize this fact.

  13. 2

    thanks for sharing! totally agree that without enjoying the journey it gets too tough. Many issues arise on the way though :)

    1. 2

      Many issues arise on the way though :)

      true, but overcoming obstacles is the reason we play games to begin with. a big part of it is how you frame and prepare for the issues you face.

      1. 2

        creating a playbook for founders with my current project :)

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