I have recently reached a curious place. I have reached Enough.

Where is Enough? Enough is this place where I feel fundamentally content with what I have and where I am in life. This is a peculiar place indeed, hidden in plain sight in a world where the default mode is a continual striving for more.

I have followed the logical path towards Enough for many years, and I hoped that one day it would bring me here. That path is paved with salary increases, income-generating investments, bucket list checkmarks, and books moved to the “read”-section of the shelf. That path has gotten me closer, indeed, but until recently, it never got me quite to the final destination. Never quite to Enough.

So how did I ultimately get here? By choice.

Enough is a choice.

The choice is to pick appreciation over envy, contentment over greed, and inner peace over unhinged ambition. The choice is to disregard scarcity, and embrace a sense of sufficiency and security. The choice is to make the goalpost stop moving.

I believe the choice can be made at all levels of wealth and prosperity. In some sense, perhaps in a rational sense, it should be easier to make the choice if you have plenty of resources. But in another sense, as most relatively-well-off homo sapiens can attest to, the more you have, the more elusive Enough can become.

One of the big ironies of the human condition is that the richest folks among us so often end up utterly unhappy, while many relatively poor people live lives of joy and meaning. The rich and unhappy population grows out of mimetic desire, our tendency to want what the people around us want and have. The more those around us have, the more we want, and the less we feel content with what we do have. This doom loop of mimetic desire leaves us ever separated from Enough. But it doesn’t have to be that way. The alternative is to choose Enough, regardless of how much or how little you have at this moment.

Choosing Enough is simple, but not easy. Choosing Enough means rejecting mimesis, which is fundamentally human, and embracing contentment, which is fundamentally not. Choosing Enough takes some real work.

That work is worth doing, and the choice is worth making. Because choosing Enough leads you to a distinctive sense of freedom and agency. From a place of Enough, you are free to live your life based on what you genuinely want to do and to be, rather than what you should do to satiate a hunger for more.

From Enough, you can even choose ambition without incurring dissonance. You can choose to do more, to create more, to contribute more, to make more, to grow more – even when you don’t need more. Whatever choices you make from a sense of Enough will be pure and sincere choices, exactly because you don’t need anything more to be content.

I have been operating from a sense of scarcity for 30 years. The world is an uncertain place, and accumulating resources, options, knowledge, relationships, stuff and information has been my default strategy to increase my odds of surviving and thriving in the face of that uncertainty. I’ll probably dip back into that sense of scarcity from time to time – but I hope I’ll be able to make Enough my home base for the long run, by choosing Enough again and again.

I have that same hope for you, too. Thank you for reading.

The Real Work is finding the 20% of inputs that drive 80% of results, and then focusing exclusively on those 20%.

The Real Work is creating systems today that will save you time, energy, money and attention in many tomorrows.

The Real Work is making it enjoyable.

The Real Work is coming to terms with your life’s finitude, your todo list’s infinitude, and the impossibility of ever squaring the two. (See “Four Thousand Weeks” by Oliver Burkeman)

The Real Work is taking care of your health and sanity so you can sustain a high-output career for the next 30 years, not the next 30 days or the next 30 hours.

The Real Work is having that difficult conversation you have been putting off.

The Real Work is developing radical self-awareness – and helping colleagues do the same.

The Real Work is deep observation, watching the illegible as closely as the legible.

The Real Work is doing one extra reference check, even when your gut feel is superb. Especially when your gut feeling is superb.

The Real Work is balancing optimism and paranoia.

The Real Work is being the kind of person who empties the office dishwasher when nobody is watching.

The Real Work is culture building.

The Real Work is balancing pride and humility – your own, and your company’s. Be proud of what you make, and humble enough to know you can still improve tremendously.

The Real Work is staying in the game for the long run, trusting compounding to do its magic.

The Real Work is solving problems before they appear.

The Real Work is making great documentation.

The Real Work is trusting your employees to do the right thing in your absence (and hiring accordingly).

The Real Work is questioning assumptions – not in the name of obnoxiousness, but in the name of improvement.

The Real Work is leading by example, without any expectation of followership.

The Real Work is being grateful for what you get to do, and who you get to do it with.

The Real Work is figuring out what your Real Work is.

Grunt work has a bad reputation.

It is "low-leverage", "rarely worth doing", and should be "eliminated, automated or delegated", according to the productivity gurus of the world.

For the most part, I agree. I've spent years automating stupid-work in my own life, and I am actively engaged in the battle against the never-ending barrage of grunt work that, like a fire hydrant blasting O2 into the face of a thirsty dog, overwhelms most knowledge workers who are trying to get anything important done.

But I've recently found a new perspective. Or, perhaps, a new perspective has found me. I now believe that a certain amount of grunt work can be a refreshing, soulful, and yes, even spiritual practice.

As I understand spiritual practices, they are designed to give its practitioners a rejuvenating break from their daily, earthly, actual lives. By pausing life for a moment of silence, chanting, woodcutting or whatever your spiritual practice of choice is, you transcend the ordinary and focus on something else than whatever you're actually doing with your life. In short, you give yourself a break.

So, too, can you use grunt work as a break from your highly demanding professional life.

Your Real Job as a knowledge worker in a high-complexity role or domain, is to think clearly and make good decisions consistently. That is difficult and demanding indeed, and most of us are not able to do so at the highest level 24/7. Enter grunt work.

Grunt work, when scheduled intentionally, can give us a pause from the important, high-leverage work of thinking and decision making. It can act as a mechanism for professional rest and rejuvenation, much like a long oooohhhmmm for a praying Buddhist.

Built into many spiritual practices is a promise of reaching something transcendental. The spiritual practice will, supposedly, move you closer to something or somewhere better and calmer than your regular life, be it Heaven, nirvana, or just to the bottom of that difficult yoga stretch.

So too with grunt work. “Just do it now, and you will feel free”, it promises with a deceptive voice. A clear, undistracted mind is just a few emails and five todos away, goes the siren song of grunt work. Perhaps so. But you soon realise that the end destination is illusory, always just out of reach. Inbox Zero and Nirvana are similar in this regard. As soon as you believe you may have arrived there for a fleeting moment, you will be sent back to where you came from, doomed to eternally try again to reach that blissful state.

So do not fool yourself into believing you can make the grunt work go away once and for all, leaving you in peace with an eternally empty inbox or todo list. Instead, embrace the grunt. Use it as a well deserved pause from your difficult and demanding job. Use it to give yourself some well-deserved dopamine hits as you tick off those Asana tasks and archive your Mount Kilimanjaro of old emails.

Just make sure you don't overengage with the grunt.

It will tempt you to completely disregard your important work, the stuff that matters.

For just like other spiritual practices, it can go too far and become all-consuming. For as lovely as nirvana and perpetual Inbox Zero both appear, one must always remember that they are fleeting illusions.

Life is best lived grounded here on Earth, with the occasional visits to the spiritual hintherlands. The opposite rarely works. So too, is your professional life best lived in the realm of important tasks and deep thinking, with occasional visits to Gruntistan. The opposite rarely works.

I turn 30 today (woo-hoo! 🎉).

As one decade waves goodbye and another says hello, I’ve spent some time to reflect on what I’ve learned from the first 30 years of life, and what I want to bring with me into the next 30.

Here is the list:

1. Pursue less but better. Less distractions, less stuff, fewer projects – better focus, better quality, better balance.

2. Give things away. The less I own, the more free I feel.

3. Energy management trumps time management.

4. Action creates information. Have a bias to do something rather than overthink it (except for irreversible decisions, which are rare).

5. Say yes to everything when I’m opportunity poor. Say no to most things when I’m opportunity overloaded.

6. Everything compounds – health, relationships, wealth, skills, knowledge, wisdom and so on. Get the most important flywheels going, and let compounding work its magic.

7. Play long term games with long term people.

8. Choose my own desires carefully, and audit them frequently. Don’t get swayed by mimesis.

9. Create an everyday life I don’t want to take frequent vacations from.

10. Invite serendipity to strike.

11. Shape my environment with intention. Don’t own a TV to make sure I don’t waste my life watching it. Don’t buy ice cream to make sure I don’t eat it. And so on.

12. Write more.

13. Invest in myself, in index funds, and in speculative things that will either go 10x or go to zero. In that order.

14. Define enough, and stick to that definition for as long as I can.

15. Curate my media diet. Information is for my mind what food is for my body, so don’t consume junk.

16. Meet interesting people from the internet in real life.

17. Remember the most interesting takeaway from Pareto’s Law: most things don’t matter, so don’t fret over them.

18. Invest in my friends’ startups. If they win big, we’ll win together. If it goes to zero, they’ll be grateful I believed in them.

19. Create memorable, photo album worthy experiences often.

20. Take a think week by myself every six months.

21. Track stuff. It motivates me more than I like to admit.

22. Seek (or create) opportunities with asymmetric upside.

23. Invite people for dinner.

24. Remember that everything around me was created by someone who wanted it to exist. The world is malleable, so change it for the better.

25. Prepare for the worst, and hope that I’m wasting my time and money doing so.

26. Be aware of incentives – both my own and others’.

27. Assume good intent.

28. Scarcity is a lie. Embrace a mindset of abundance.

29. Learn from the past, act for the future.

30. Be here now.

Looking forwards to the next 30 laps around the sun!

But not so fast. Before you dive into the coming year, please stop, pause and reflect on the one you leave behind. Not to linger excessively in with the past, but because closing off 2022 with intention will help you make 2023 even better.

Take a few hours (or, ideally, a few days) to conduct a proper Annual Review process before jumping into the hustle and bustle of everyday life in 2023.

I’ve done this for the past five years, and it’s one of the most impactful things I do each year. It helps me seriously question the direction my life is moving in, and to make adjustments intentionally.

So, what exactly does an Annual Review process look like? Glad you asked.

Below, you’ll find a step-by-step Annual Review template which I’ve developed for myself over the last few years. To conduct your own review, feel free to complete all the steps in order, or just pick and choose the reflection exercises that speak to you.

Whether you spend 30 minutes or 30 hours reviewing the past year, I guarantee it will help you start the new one with more intention.

Best of luck, and happy new year!

Thank you for following along my writing in 2022,

-Jacob

Jacob’s Annual Review Template (as of 31.12.2022)

Step 1: Review and reflect on the past year

• Free form writing: Write out what this year was like for me, stream-of-consciousness-style, from memory.

• Compare the year with my expectations for it. Revisit the ambitions, expectations and predictions I had for this year from 12 months ago. What did I get right? What did I get wrong? Where did I succeed and fail, and why?

• Audit how I spent my time this year: Go through my calendar, photos and credit card statements, and write down my Highs and Lows from the year in two separate columns.

  • What gave me energy? What drained me?

  • What do I want to do more / less of? What should I stop doing alltogether?

  • Who do I want to spend more / less time with?

  • Bonus: Send pictures from great memories to friends and family as I go through my photos from the year.

• What did I learn this year? Write down any lessons learned this year, especially things I want to remember for the future (e.g. mistakes I don’t want to do again).

• What am I grateful for from the year that passed?

• Big picture stuff: Reconsider the big, important things in my life, like my personal values, principles, and beliefs. Should anything change? Why / why not?

• Bucket list review: Did I check off anything from my “life goals” list / bucket list this year? Can I schedule something for next year?

• Answer any questions that grab my attention from the list below:

  • Which of my decisions led to the most unexpected outcomes? Where were my predictions most off, in either positive or negative regard? How might I use that information to improve my predictions and decision making processes in the future?

  • What were my top 3 wins from this year?

  • Where was I most wrong? Which false assumption(s) did my wrong decisions or thought processes rest on?

  • What did I (or should I) change my mind about this year? (And the opposite: what did I strengthen my convictions about this year?)

  • Which aspects of my life did I over- and underinvest in? How might I find a better balance going forwards?

  • How far off am I from living my ideal life? Where are the biggest discrepancies? What might I do to minimise them?

  • Where was I most fragile this year? How can I make myself more robust/antifragile?

  • When and where did I take smart and stupid risks this year?

  • What am I most and least proud of having done this year?

  • What made me overreact the most this year?

  • What is left undone from this year? What do I have to do to "complete the year” mentally and emotionally?

  • What is one word or sentence that best summarizes this year?

Step 2: Set direction and ambitions for next year

After reviewing the past year, I like to keep the “reflection momentum” going by immediately start thinking about the coming year.

The step-by-step process for that looks like this:

• Write out in detail what my life looks like 12 months from now. Where do I live? What am I thinking about? How’s my health, relationships, work, financial situation, mental state, rate of learning et.c.? Dare to be ambitious in this exercise.

• Set goals and ambitions for the year: What would have to have happened by the end of next year/quarter for me to reflect on it and consider it a big success?

  • Via negativa / "anti-goals": what good (but not great) goals/directions will I NOT pursue this quarter, in order to make time and space for what truly matters?

  • How can I get help achieving my goals going forwards? Can I hire a professional? Ask a friend?

• What will I do more/less of next year? What will I stop/start doing?

• Which books do I want to read?

• What skills do I want to develop, or what knowledge do I want to acquire/strengthen? Which courses do I want to take? Which personal development focus areas/directions am I working towards this quarter?

• Which memorable experiences do I want to create for myself and others?

After deciding on a general direction and a set of ambitions for the coming year, there’s only two things left to do: operationalise my ambitions, and start making progress.

Operationalising my ambitions simply means putting stuff into my calendar and todo lists. An ambition without time dedicated to its pursuit is almost worthless – it has to make its way into my calendar to have any chance of coming true.

Finally, do something right now to start making progress towards your goals and ambitions. This can be ridiculously small and simple, the point is just to create some minimal momentum in the right direction. If you want to get in better shape next year, do one single push up right now, for example. If you want to learn a new instrument play one chord on the piano. If you want to start writing online, publish a single Tweet. Then do it again tomorrow, and the next day, and so on.

That’s it! You’re off to a great year ahead. Good luck!

That might be a good idea if you're starting an activist group. But if you want to build an enduring, great company, I believe Sinek is wrong.

I was wrong for a long time too. For years I intuitively believed in "Start with What". Figure out what to do, what the great idea is, then go for it. It seemed to obvious, so logical. Everything else is just support structures for what you want to accomplish, right?

No. I've changed my mind.

Don't start with Why like Simon.

Don't start with What like old me.

Don't start with How like any great engineer will do.

Instead, start with Who.

Why? Because business is a social game, and we are social animals. For most of us, who we work with is more important than what we work on.

Consider for a moment this harsh reality of entrepreneurship: building any business into an enduring, great company takes a long, long, looong time. Five years at least, often 10 or more.

With that in mind, which of these two scenarios would you choose?

• A) Spend 10 years working on a mediocre business idea with a wonderful team of interesting people with high trust and integrity, or

• B) Spend 10 years working on a fantastic idea with a bunch of random people with whom you have a mediocre connection?

Simple, right? Even I, an introverted, "leave me alone" kind of guy, would choose option A every time.

Now consider the fact that 80+ percent of all new businesses fail within five years, despite the founders' very best intentions and efforts to succed. In other words, your company's most likely outcome is failure, regardless of how great your idea is. It is "default dead", not "default alive" according to statistics.

This lets us consider a simple question: would you rather fail to build a company together with great people you love and trust, or fail together with mediocre people who just happened to believe in the same idea or vision as you?

Obvious again. Failing sucks, but failing with a great team of people you like and respect sucks much less than the alternative.

In fact, a rough startup failure with great people can be kind of fun in a weird way. Trust me on this one – my first startup turned out exactly like this. The business model was terrible, but the people involved were fantastic. The company did not become a raging success, but we all look back on it with fond memories, and the other 2-3 guys are still among my closest friends to this day.

Starting with Who also has a non-obvious bonus feature: you keep more options open. A great team of people who want to work together, can often pivot to better and better ideas or opportunities over time. But a team who is only united by the idea or project they are working on right now, will likely disintegrate if that idea doesn't work out.

The bottom line is this: instead of starting with your clever idea, I recommend you start by figuring out who you want to work with for the next 5 to 10 years of your life.

Looking back, I can see that this is in fact exactly what I did 5 years ago, although I didn't see it so clearly at the time. My company Braver did not start with a fantastic, radical idea. We didn't have a specific huge opportunity in mind, nor some strong vision we would go all in to pursue. The only thing my cofounder and I had were each other (which sounds like a clichéd opening line of a shoddy romance novel, but is quite true). We had worked together on a side project in the past, and enjoyed figuring things out together. That was pretty much it.

We started with Who, and the five years since have been fun, profitable and full of learning. We couldn't ask for more.

..and the Why and the What of our business? We're still trying to figure those out!

Two weeks ago, I met my #1 intellectual hero, Nassim Taleb. I got a handshake, almost spilled coffee on the man, and spent 45 minutes in a room with him at a private gathering. How did that happen? Through a series of emails to acquintances and strangers – Taleb was coming to town for a conference, so I unashamedly asked the conference hosts if there were any chance I could say hello. Turns out there was.

Just this morning, we signed a new customer deal worth $100k+. Where did this opportunity come from? It started with a simple LinkedIn message I sent to a complete stranger nine months ago.

Three of my colleagues (aka almost 50% of our company!) found me/our company online, respectively via my guest post in Luke Burgis’s newsletter, an old article about biohacking featuring yours truly, and some random Tweet.

In all these cases, I benefited from luck, good fortune, serendpity – call it whatever you want. But in all these cases, I had also done something do attract that luck to strike. I strongly recommend you do the same.

See, we all have what’s popularly called a luck surface area. The bigger your luck surface area is, the easier it is for luck to hit you, and the more often you’ll get lucky and benefit from good fortune. The smaller your luck surface area, the less luck you’ll attract.

Let me throw in a disclaimer before moving on – you’ll never be able to chose to be lucky on demand. Luck is not some Uberized phenomenon which you can hail by the push of a button only to to show up outside your doorstep four minutes later.

But the great news, and the point of this post, is this: luck is not completely random either. You can invite luck into your life. You can increase your luck surface area. And since luck can lead you to all kinds of fantastical opportunities and benefits, expanding your luck surface area is one of the most powerful things you can do.

How exactly?

The conceptual answer is that you must put yourself in positions to get lucky often.

The practical answer is that you shuld do things like..

• Go to parties. Go to conferences. You might meet future best friend, co-founder or a new customer there.

• Send DMs to cool strangers on social media (just don’t be creepy about it).

• Start a blog. Write random stuff on Substack (like this!). Like-minded people will magically find you.

• Si hi to cute girls in bars (or on the street, if you’re so fearless). Go on blind dates.

• Host dinners at home (protip: you invite three friends and you make them bring one interesting person each).

• Ask. Just ask for things. You’ll be utterly amazed at the rate of positive responses.

• Learn something new (ideally in live courses with a group of strangers).

• Send thoughtful emails to CEOs (aka the most effective way to get a great job).

• Hold keynote speeches (this one is crazy powerful).

I could go on and on, but you get the point. Get out there and put yourself in positions in which good things can happen.

Unfortunately though, in 9 out of 10 times, seeking out luck will lead you to… absolutely nothing. Nada! Nil, nix, nutthin’.

But every once in a while luck will strike, and you will find something that makes all the previous attempts worth it. Worth the weirdness, the embarassment, the fear of hitting publish, the pre blind date awkwardness. All of it.

The bottom line is this: You never know when luck will strike, but you have the power to create the conditions for luck to strike often, and with force.

Enough said. Now it’s your turn.

Go get lucky.

Bonus point: the link between luck and agency

Do you see the connection between luck and agency, which I wrote about in my last post? High-agency people invite luck into their lives by acting, by doing things, by “being in the arena” as Roosevelt would say.

Truth be told, this entire post is utterly meta. I had no intention of writing about luck in this newsletter. But after the last post about agency, an old friend replied and said “hey, you should write about luck next time, for hi-agency people surely must be luckier than low-agency folks”.

Let that be the last example to drive my point home: I sent out a newsletter, and thus increased my luck surface area a tiny bit. My old friend Morten replied with an idea for a new newsletter post. Lucky me, suddenly I had something to write about – and here we are.

(Yes, ideas for new newsletter posts are most welcome indeed – just hit reply to this email!)

Agency is the capacity and willingness to act.

Agency is the antidote to mindless drifting.

Agency is the act of living with intention and direction.

In a world of coddled minds, helicopter parenting, incel culture and passifying entertainment, agency is a most precious and scarce resource. One that ought to be celebrated and promoted, yes indeed – but most importantly, one that ought to be lived out day to day.

I will continue to advocate for agency. But a new perspective has recently entered my mind – may the agency agenda go too far?

I’m afraid it can. Too much agency can become hustle porn, or the tyranny of excessive personal development, or a direct path to burnout. It can become Extreme Ownership taken a tad bit too far.

The logical progression is straightforward – if you have Agency Over Your Life, if you can achieve anything you want, then you must simply apply yourself better, faster, stronger, and you will ultimately reach Success Nirvana. Just add more discipline, more doing, more work. Bias to action. Execution all day long. Whatever it takes. Sink or swim, keep moving forward. Just listen to a few more Alan Watts deep house remixes so your subconscious mind will finally get the message, then you will Make It.

But… the results in your life are unfortunately not simply a direct reflection of your level of sheer hustle. This truth is an inconvenient one, but a truth nevertheless. Luck, disasters, genetics, geopolitics, global finance and a host of other factors outside of your control can and will shape your destiny, whether you like it or not.

Yes, at the margin, the person who works hard and makes smart decisions should come out ahead of the comparable person who slacks off. But even the hardest working champ out there can get struck by lightning, hit by a bus, or graduate in a 2008-style economy – even if he does monthly reviews, follows a perfected morning routine every day, lives an exquisite Vegan Keto Crossfit lifestyle, and has internalized the complete bibliography of his spiritual masters Jim Collins and Eckhart Tolle.

There are many ways of dealing with this unfortunate fact of life, but the most productive way seems to be to simply Accept it.

Easier said than done, especially in domains of life where you want to, feel like, and generally do have a high degree of agency and ability to shape how things turn out.

It is relatively easy to accept that I won’t become a world class NBA player, because I’m not born as a freakishly tall man in America. It also helps that I don’t care about basketball whatsoever – accepting impossible futures I don’t want is easy as pie.

On the other hand, I would LOVE to reach tens of thousands of people with this newsletter, and I know believe I could make that happen if I truly applied myself. Yet, it’s currently just reaching ~500 people, despite several legitimate attempts to make it grow.

In other words, becoming a legitimate writer with a large number of readers might never happen for me. I can either Accept that, or apply more Agency, more hustle, more pressure and more more more to will it into being. But even if I do all that, it might not happen anyway. Then I’m only left with acceptance.

I might never have a big audience. And that’s OK.

I might never build a huge company. That’s OK too.

I might never get particularly wealthy. Now we’re pushing it here, but frankly, even that would be OK.

These are realisations I’m personally coming to terms with these days. Perhaps it’s a result of aging into a new phase of life. Perhaps it’s because I’ve thoroughly scrutinized my own desires after reading Luke Burgis’ enlightening work on mimetic desire. Perhaps it’s because of being near tragic events that put things into perspective over the last few months.

Whatever the reason, I’m moving towards acceptance. Acceptance of the fact that I cannot control every variable that plays a role in whether or not I reach goals or achieve this or that, regardless of how much agency I apply.

This led me to Tweet out a question the other day.

My wise friend Tim replied immediately and put the case to rest.

Tim is right. Agency and acceptance must live together.

Apply as much agency as you can, and accept whatever happens.

Do your very best, and let the chips fall where they may.

Yesterday I realised I've largely missed something critically important about one of the most powerful concepts in the universe: leverage. The story of Archimedes has a missing, more nuanced half. Let's go find it.

Give me a lever long enough and a fulcrum on which to place it, and I shall move the world.

– Archimedes

Everybody knows the tale of Archimedes' lever, and understands the key takeaway: if you have a long enough lever, your input and effort can be multiplied to generate disproportionately large outputs and results.

Nothing new there. However, here is the crucial part of the story that I've largely overlooked: where you apply the lever is almost as important as how long the lever is.

Think about that for a moment. If Archimedes were to move the world, he would certainly need a long lever, but he would also need to apply it to the right leverage point, specifically at the very bottom of the Earth. If he places it anywhere else his efforts will be in vain, regardless of how long his lever might be.

Furthermore, if Archimedes wanted to move the Earth in a specific direction, he would need an even more fine-tuned approach. A long lever applied at almost the right place will create results that are very different from what he intended. Such a slightly misapplied lever may even do more harm than good, because it can lead you very far and fast in the wrong direction (as everyone who has been financially leveraged and had the market turn on them can attest to).

This is worth keeping in mind as we think of leverage in our own lives and businesses. After all, just creating some random effect or result is rarely what we want – what we're after is effects and results that move us in a specific, desired direction.

Let's move on to a separate point. In addition to where we apply our levers, we must also remember to actually use them. This might seem utterly obvious, but believe me when I say that some people, and some organisations, are much more skilled at creating leverage for themselves than they are at using the leverage they have.

I know this is true, because I myself am one of those people.

Looking backwards, I can see how I've been very focused on extending levers in my life, but much less focused on applying them to meaningful leverage points.

One example could be over-investing in learning new skills (extending a lever), but under-investing in actively applying those skills to opportunities (leverage points) for profit or other benefits.

Another could be saving up capital over time (extending a lever), but not deploying enough of it when promising investment opportunities (leverage points) came along. (This is also true for social capital, by the way).

Yet another could be investing time in writing this newsletter, but not bothering to promote it in relevant channels and forums.

A final example, from the professional realm this time, could be hiring fantastic employees, but failing to channel their energy and effort into what matters most for the business (as I alluded to in my post from a few weeks ago).

All of these examples point to a tendency to invest precious resources in developing options and potential, but then stopping short of actually calling on those options to turn the pent-up potential into desirable results.

This is clearly not a productive tendency for any person or organisation who aspires to create great results. The opposite would obviously be problematic too – if you constantly identify leverage points and opportunities, but never have any available levers or resources at your disposal, you won't get anywhere either. You need both at the same time.

The bottom line is this: don't miss out on the nuanced half of Archimedes' story. Don't go about blindly looking for long levers and fulcrums – make sure you also apply your levers to the right leverage points, with precision and intention. Then push as hard as you can on your levers, and you might just move the world in the direction you want.

Further Reading

• Good Strategy, Bad Strategy, by Richard Rumelt (next week's post will be about this book!)

• Points to Intervene in a System (Danella Meadows) (I haven't read this yet!)

“A life well lived” is a maxim many people aspire to live up to.

Yet, so many of us modern Westerners instead end up with merely “a life well managed”.

Managing oneself is hailed as the “key to success”, both by Peter Drucker and by popular folklore. But can it go too far? Can we miss out on Life in the pursuit of optimal self-management?

I recently got this idea for a metaphor to illustrate the balance between managing your life and truly living it: a painting and a frame.

Imagine a beautiful painting (like the absolutely stunning work of art below!). This represents your life. The more vibrant the painting, the more vibrant your life, dull colours may represent dull times, interesting shapes are interesting forces shaping your life, and so on.

Now imagine a frame around your painting. The frame represents the management of your life.

A solid frame means you have your shit together. You have a strong grip on life. Your habits are sound, you pay your bills on time, you reach inbox zero on a regular basis, you’re considered a productive member of society, and so on. A thin, weak frame means the opposite. Your life is a mess. Your apartment looks like a postapocalyptic wasteland, your health is a train wreck, and you’re perpetually broke.

Clearly you’d prefer to have a strong frame around the painting that is your life. But here is the big question that self-aware, well-managed folks may sooner or later ask themselves: can the frame get too strong?

Yes, indeed it can. Consider the picture below. The unproportionally large frame looks ridiculous. The frame is so dominant there’s almost no space left for the actual painting!

This represents the life of a person who is Over-Managing and Under-Living his life. His life is hidden behind layers and layers of exquisite framing, barely visible to himself and others. He has been so hung up in creating efficient, intentional structures for his life that he has forgotten to also Live it.

As this metaphor illustrates, we ought to find the right balance between Living and Managing our lives. Luckily, we can all continuously develop both our painting and our frame at any point in our lives.

If you have a frame that is too dominant for your painting, you have two choices to regain a sense of symmetry and balance: make the frame smaller, or make the painting bigger. I’d recommend the latter – instead of throwing out all the structure you have built into your life, use it for support instead. Have it support a bigger, more extravagant and vibrant painting. Bring out the pencils!

If you have a frame that is too small for your painting, again you have two choices: make the frame bigger, or make the painting smaller. Advice to this person should be a little more nuanced. Obviously, work on strengthening the frame if you can. But these vivacious life-livers may also need to shrink the painting a little bit first, or at least create some blank space. After all, it’s extremely difficult to develop your frame and get your life in order if you’re constantly high as a kite, hung over or running to the next fun and life-affirming experience (/escape).

Let met wrap up with one final point on this metaphorical FRAMEwork: as your life expands in complexity, so should your frame. As a student, a sufficient frame might be a schedule showing the time of your classes, plus the established habit of waking up at some point (preferably daily). But as CEO of a big company for example, your frame might include nannies at home dealing with the kids, wealth managers dealing with your money, and personal assistants dealing with just about everything else.

But even then, even if every practicality is systematised, automated or delegated to someone else, you might need to be reminded to do something very simple: to occasionally Live.

Thank you for reading. Have a vivacious Monday,

-Jacob (working to expand my painting inside a pretty well-developed frame)

I’m out of the country for the first time in 19 months. During that year and a half, I’ve thought and talked a lot about remote work – why, how and what kinds of work one might do when away from the office.

Yet, I haven’t worked properly remote until now. Yes, I’ve worked from home and from the family cabin, but not abroad, far removed from my everyday circumstances.

Alas, here I am, at some Greek island with my laptop clocking away.

This got me thinking about how changing your location can facilitate a change in your mode of working. I think differently when on the move in Greece than when I’m in the office in Oslo, just like I think differently when working from my kitchen table.

This is because we homo sapiens tend to associate certain mental and emotional states with certain places. Therefore, some places are more conducive to certain kinds of activity, and certain types or work, than others.

For me, the office is ideal for productivity and getting things done. My desk is optimized for productivity, and my brain associates the office with long days of checking off tasks and making things happen.

Hopping from island to island in Greece, while excessively consuming iced coffee and eggs benedict at shabby cafés definitely creates a different mental state than that of the office. This state is far from ideal for maximum productivity and short-term output. But it is surprisingly conducive to thinking about the bigger picture, and looking into the long term future.

Does this mean I should spend the rest of my career gazing into the Mediterranean asking big questions? No. But it does mean I might consider getting away from the office on a regular basis to help facilitate other modes of thinking and approaching professional challenges.

The bottom line is this: location is a powerful parameter you can tweak in order to change your mode of work.

With that said, location is far from the only parameter you can tweak. A few other parameters I’ve experimented with include:

• Tools: working on a laptop versus on a piece of paper, versus a big whiteboard can allow you to examine a problem or a situation in different ways.

• Stimulants: writer David Perell talkes about working in “beer mode or coffee mode”; he uses coffee for productivity, beer for creativity. Other substances can definitely create interesting results too – see this and thousands of other articles on “microdosing” if you’re curious.

• Movement: if you’ve ever been in a standing meeting, you may have noticed that just getting up from a chair can change the dynamic of a meeting significantly. Right after a heavy workout, you might get into a certain state of mind. Harness the effects of movement on your ability to work in various ways.

• Working alone or together: this is perhaps self-evident. We all do both, but many of us don’t choose whether to be alone or together intentionally, based on what type of thinking is needed and what kind of work needs to get done.

• Physical state: despite its bad reputation, being in “fight or flight”-mode can actually help you get things done, so if you have a long day of grunt work ahead, perhaps you should consider stressing yourself a little. Just make sure you come back to a relaxed, parasympathetic state before you start making any important decisions.

• Time of day: I have my most productive and clear-headed hours in the morning, but I can have loads if creative ideas in the early evening. Other people are the opposite way around, or are wired completely differently. If you become aware of how your thinking style changes throughout the day (or week, or month, or year!), you can do the right kind of work at the right kind of hour.

• Headspace: Sometimes I feel open minded, sometimes I don’t. Creative work should be pursued with an open mind, but grunt work can be done without being very open minded at all. Some types of “thinking” may even be best done in your sleep (!), when your consciousness is turned off entirely – Thomas Edison once said "Never go to sleep without a request to your subconscious”, because he believed the subconscious mind to be an excellent problem solver when the body is asleep and the conscious mind gets out of the way.

If you become aware of how these various parameters impact you, your state of mind, and your mode of work, you can start to tweak them intentionally. Doing so can yield incredible results.

All of this is essentially just about setting the stage for doing great work. It’s basic preparation. The importance of good preparation is much more obvious in the world of physical labour, because the risks of getting injured are so obvious – you would never go out for a long day of chainsawing without spending five minutes to put on protective gear first, for example. You as an office worker might not be at risk of chopping off your legs on any given Tuesday, but preparing for a good day, week or life of knowledge work is still important.

The bottom line is this: if you set up your outer and inner environment in an intentional way, then doing your work gets so much more effortless.

So tweak and tinker with all the parameters, see what happens, iterate and repeat until you find what works for you. It might help you do the best work of your life.

Cheerio from Greece,

-Jacob

It’s Sunday, second cup of coffee o’clock, and I’m making a list of possible topics to write about for this post for tomorrow (which is now today, as you read these words). The list is pretty long, and could win me a bunch of woke awards for its exceptional diversity – here is everything from Pareto’s Law in practice, to octopus intelligence (!), alchemy, career hacking, over-managing your life, and the joy of missing out.

But the only topic on the list written in all caps is LEADERSHIP, because that’s what’s on my mind and on top of my list of Kindle books at the moment. So let’s start there and see where we end up.

Beware though – this post will probably become a stream-of-consciousness-style, fairly self-centered ramble in text form. You have been warned.

From Founder to Leader – From Doing More to Doing Less

We just signed our 9th employee in Braver (and looking for one more). Less than a year ago, we were literally three dudes in a garage-looking office, and now we’re a capital T Team. Exciting times ahead!

These days, I’m reflecting on what my own role in this emerging Team should be going forwards. For the last 3.5 years I’ve been doing stuff continuously. Checking off tasks. Creating systems. Making slides. Holding webinars. Watering the plants at the office... It’s been an operational day-to-day life, with some time slots to think squeezed in between all the doing.

That’s all well and fine. I’m pretty good at it. It creates decent results. It’s fun. But – there’s always a but – it doesn’t scale. As any entrepreneur will tell you, sooner or later (ideally sooner), you have to transition away from doing towards something else – leading.

At some point, your job is no longer to do everything yourself, but to empower other people to do great work.

Problems are no longer yours to solve alone, and often not yours to solve at all. They are yours to pass on to other people to solve, using their good judgment rather than your own.

In the wise words of the author of The E-Myth Revisited, “you have to work less in the business, and work more on the business”.

At that point, you no longer get paid to do. You get Paid to Think (great book by the way), and paid to lead.

Making this transition is long overdue for yours truly. This post is, more than anything else, an attempt to solidify some things I’ve read lately about how to make that transition, and what to focus on going forwards. Beyond being an effective reflection exercise for myself, I hope it will be valuable for others in similar situations.

The Only Four Things that Matter

I already know that most things in life don’t matter. Don’t sweat the small stuff, as they say. Pareto said the same thing – find the 20% of inputs that produce 80% of the results, then focus exclusively on those twenty and disregard everything else.

When I say I already know that, I mean I understand it intellectually. Living it out in practice is a whole other story. I don’t follow said advice nearly as much as I’d like, but I’ve committed to focus on doing more high-leverage stuff going forwards.

What might such stuff be? Well, as a tiny company grows, semi-conventional wisdom says that the founders should focus more and more of their time and energy on the only things that really matter:

1. Talking to customers.

2. Controlling cash flow.

3. Recruiting and hiring.

4. Communicating the vision and direction to everyone all the time.

My co-founder mostly deals with the first, and I deal with the second. The last two we must take shared responsibility for.

Regarding the third point, I think we’ll get pretty good at hiring. Not because we have much experience yet, but because we’re looking for a distinct type of person whenever we’re hiring for the Braver team. These human beings are hard to find, but they're easy to spot when we encounter one.

This leaves me with the fourth point, which stands out as the most difficult by far. Not objectively so, but the most difficult for me personally.

I generally prefer to work on things that have a defined end date, something that can be completed or resolved or fixed once and for all. I also generally prefer working on my own – to close the door, block off all possible distractions, and go deep into flow states for hours (or days, or weeks!) on end.

Communicating the vision and direction of a company is the opposite of both those things.

It’s something that will never end. It’s never “done” – you never check off the vision task in Asana. In the lingo of last week’s post, it’s an infinite game.

It’s also at odds with closing the door, literally and metaphorically. Communicating the vision must, by its very definition, be done to and with others (duh!).

This is energy and time consuming work. Therefore, it needs dedicated headspace and time in the calendar. To find some of that, I’ll need to practice something else in tandem, something that might be equally difficult and equally worthwhile: letting go.

I’ve developed a set of professional habits that center around being operational, on doing stuff, on solving problems, on being busy. I now have to practise letting go of these habits, and replace them with new ones.

But more importantly, or more fundamentally if you will, I have to let go of something else: the identity of being a doer and a fixer.

That’s the fundamental change that needs to happen, and it is also the most difficult change to make. The reason why it’s difficult can be found by answering a very deep question I’ve heard business coach Jerry Colonna ask on several podcasts:

“How am I complicit in creating the conditions I say I don’t want?”

.

.

.

(Here is a pause for you to reflect on Jerry’s question in the context of your own life)

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.

.

For example, I might say I don’t want to have too many responsibilities and too full a calendar at work. But in answering Jerry’s question, it becomes immenently clear that I am complicit in, or practically 100% responsible for, every aspect of the conditions that lead my calendar to fill up like a world class Tetris game week after week.

This is great news. Since I have created these conditions, it is clearly also in my power to change them. That’s what I’ll focus on over the next few weeks (if anyone has advice on how, please reply to this email!)

Role vs Behaviour: What Comes First?

As I’m about to wrap up this ramble of a post, I can’t help but reflect on one final question – what comes first on the path to becoming a great leader?

Is it being appointed (or self-appointed) to a leadership role, or is it exhibiting leadership behaviour?

Do you first become a leader on paper and then in practice, or is it the opposite way around? Does the designation of a leadership role inspire leadership action, or does action tend to come first?

I believe it can work both ways, but I’m most bullish on leadership in the form of actions. Leadership, as far as I understand it, is essentially just a mindset and a way of acting that is available to all, regardless of role and rank. Act more as a leader, and you might suddenly find yourself being one.

Best of luck.

-Jacob

📚 Further Reading

For more on similar themes, see these books:

• The E-Myth Revisited, by Michael Gerber.

• Traction, by Gino Wickman (also: Rocket Fuel, by the same author)

• Extreme Ownership, by Jocko Willinck.

I used to love playing video games.

As a kid, I got an Xbox for Christmas. Pure bliss. To my further delight, the IT-dude who lived next door had put a mod chip inside it. This meant it could play pirated games, which may or may not have been downloaded illegally by some 12-year old I knew 👀

Thousands of hours of fun ensued. The snowboard game SSX. James Bond Nightfire. Grand Theft Auto San Andreas. And of course Red Card 2003, an utterly ridiculous soccer game where you could play as a team of penguins, do crazy trick shots, and ruthlessly beat up other players on the football field (the fascination for pengus clearly never waned).

Then I stopped.

Today, video games have almost no appeal to me whatsoever.

Why? Is it only because I grew older and found other interests? That’s probably one part of it. But the other explaining factor is far more interesting – I found a better kind of game.

That game, as I alluded to in last week’s post, is entrepreneurship. As it turns out, the entrepreneurial journey and a great video game have striking similarities. Let’s consider a few of them.

Always a new challenge around the corner

In video games, there’s always the next world to explore, the next level to complete, the next “boss” to defeat - all while not running out of health points.

In entrepreneurship, there’s the next project to deliver, the next customer to serve, the next product to launch - all while not running out of money and energy.

It’s the same thing. The same feeling. The same anticipation for what comes next.

Leveling up takes time

Practice makes perfect. Levelling up in games take time and effort, so too in entrepreneurship.

The causal link between developing skills and reaching a new “level” in entrepreneurship is obscured, though – you don’t have clear progress bars that show you when you’ll level up. If you can stomach the uncertainty, this makes it even more interesting than the predictable up-levelling in the video game world.

Variable rewards keep you hooked

We know from psychology that variable rewards are extremely addictive both for humans and for many animals.

The infamous psychologist B.F. Skinner demonstrated this in the 1950s using mice, a lever, and treats that mice dig. When a mice hit the lever, they’d get a treat. In one experiment, they’d get the same treat every time they hit the lever. In another experiement, they’d sometimes get a big treat, sometimes a small one, and often no treat at all. The mice in the first experiment quickly got bored, but the mice in the second experiment went bananas. They pulled the lever like crazy, over and over and over again. The suspense and the surprise of the variable rewards got them completely addicted.

Video game makers know this, so video games are full of variable reward mechanisms. You walk around looking for Pokémons, for example – most of the time, you find nothing. Sometimes, you find basic creatures you’ve seen a hundred times before. But then, once in a while, you find a rare one, just like Skinner’s mice once in a while would get a huge treat. So you keep playing and playing, tapping the levers again and again, because maybe the next one is the rare one..

Entrepreneurs’ professional lives are similar. Most of your ideas fail. Most projects don’t work very well at all. Most potential prospects never become customers. But sometimes they do. Sometimes it works. Sometimes you sell something, or raise some money, which gives you just enough runway/cash/oxygen to continue playing the entrepreneurship game, to continue pulling levers, to continue looking for the big win.

And once in a while, you actually hit it. You sign a huge client contract, you convince an extremely talented person to join your team, you achieve a technical breakthrough in your product. You get the big treat. So you keep playing..

It’s best with friends

The best video games are the social ones. Today, social gaming happens online, but when I was a kid, it happened with four people in front of the same TV playing James Bond Nightfire. In our house, the TV was a 28” box for a long time, so we’d sit on the floor with our noses practically touching the display. Good times.

Entrepreneurship is the same thing. For all the talk of “solo founders” these days, we must acknowledge that for most people, entrepreneurship is best with friends. Building a business is an inherently collaborative thing to do.

Complementarity pays

In Pokémon games, it’s no good having five identical Pikachus as you enter a battle. In football games, it’s no good having 11 goalkeepers make up your team. In World of Warcraft, it’s no good being a guild of only “druids” (or whatever they’re called – I’ve never actually played WoW).

Instead, you need different, complementary skills, characteristics and strengths to make up a strong team. When building a company, the same thing is true. A wide set of skills and strengths is required simply to operate, and doubly so if you’re hoping to make anything successful1.

Entrepreneurship is a Better Game

I could go on and on about similarities between video games and entrepreneurship, but I’ll stop there. The point has been made.

Let us instead return to my initial claim – that I’ve lost interest in video games because I’ve found a better game. How exactly is the entrepreneurship game better than a well-designed video game?

Real stakes

Video games have a fundamentally fakeness to them, because they take place in constructed, digital worlds (for the time being, I make the assumption that the offline world is more “real” than digital video game worlds – although the rise of the Metaverse might change this in the future!).

This unfortunate fact is at the back of gamers’ minds (unless they get so enmeshed in the game that they lose touch with reality, of course). This means gamers always know that the stakes in the game are also fake.

If you die in a video game, you can always start over, so there’s no real downside. You intuitively know that, which shapes your behaviour. You don’t care as much, you don’t put as much of your soul into it, because you can always just try again.

The money you earn and the valuable assets you accrue in the game are only valuable within it2, so there’s no real upside either. You know that too, you’re aware of the inherent meaninglessness and worthlessness of everything that happens inside the game, which also shapes your behaviour.

On the other hand, the stakes in entrepreneurship are very real indeed.

There is definitely real downside. If you go bankrupt, well, then you’re bankrupt (yes, technically you can start over again, of course, but not by a mere click of a button).

There is also, unquestionably, very real upside. If you’re profitable, you make actual money that can be spent in the real world. If your product or service works, you improve real, human lives by solving problems for customers.

This makes the entrepreneurship game much more engaging than most video games can ever become. Entrepreneurs have serious skin in the game.

Positive spillover effects on the rest of your life

Most of us still live most of our lives in the “real world”. Yes, digital worlds are becoming more and more real, VR is almost a serious thing by now, and the Metaverse will blur the lines further, but there is still a significant gap between “real life” and “video game life” for the vast majority of the human population.

It is therefore unfortunate for gamers that the skills, know-how, social status and track record they develop within video games are largely (note: not completely, but largely) irrelevant outside of said games.

Entrepreneurs are luckier. They spend their time in a game that has very positive spillover effects on the rest of their lives in the real world.

Most of the skills you learn through an entrepreneurial journey are extremely valuable outside of the narrow game of entrepreneurship – you can leverage them to get a better, “regular” job if your startup fails, for example. Your entrepreneurial track record, if somewhat successful, can give you access to lucrative investment opportunities, or to well-paid speaking gigs, or to valuable, closed social networks, and so on.

Right now, entrepreneurship is so hot in Western societies that even failed entrepreneurs are held in fairly high societal regard. In that sense, dabbling in entrepreneurship has almonst guaranteed upside: if you win, well, good for you – but if you lose, you still kind of win, because just making the attempt is seen as courageous and positive, which can boost your subsequent “normal career”.

It never ends

I wrote earlier that “In video games, there’s always the next world to explore, the next level to complete, the next “boss” to defeat”. That is true… until it isn’t anymore. Video games do come to an end eventually.

Entrepreneurship doesn’t have to end. Ever. There’s always another problem to solve, another way to add value, another idea to test. Always. As I wrote last week, it can truly be an infinite game if you want it to be.

As someone who enjoys playing the entrepreneurial game, that is good to know.

-Jacob

Infinite Entrepreneurship – The Philosophical Basis for an Entrepreneurial Life

Entrepreneurship is ostensibly about value creation, strategy, decision making under uncertainty and a host of other narrow, business-esque factors. Sure enough, but it can also be viewed through a more holistic, philosophical lens, if one considers entrepreneurship as a broader, all-encompassing lifestyle choice for certain people with certain proclivities.

I happen to have a philosophy on the notion of entrepreneurship as a lifestyle choice which can be summed up in six short words: “stay alive, and keep making bets”. Ernest Hemingway would be proud. Before I explain the link between staying alive (no, that’s not a Bee Gees reference!) and entrepreneurship, let me first introduce you to an old theologian called James. 

Introducing Finite and Infinite Games

A somewhat obscure religious scholar named James Carse wrote an excellent book called “Finite and Infinite Games” in the mid 1980s.

In this book, he argues convincingly that everything we do in life can be seen as game – the career game, the love game, the status game, the football game, the learning game and so on.

He then lays out a brilliant framework for distinguishing between two distinct types of games, which are fundamentally different in terms of rules, ideal outcomes, types of players and duration of play.

A finite game is any game with clear, predefined rules, a set start and end time, known players and a mutually agreed-upon outcome. The point of a finite game is to win the game within its defined parameters, leaving the other players as losers. Think soccer, tennis, rowing, chess or ludo as examples. 

Infinite games on the other hand, are more complex. In these games, the rules are vague, subject to change and open to different interpretations from one player to another. There is no defined end point, there are no winners and losers, and even defining who the players are can be difficult. Furthermore, and most importantly, the goal of a player in an infinite game is not to win the game, but to keep on playing. 

Some examples of infinite games are life, evolution, your marriage, your health, and your journey of self exploration and personal development. Think about it – there are no “winners” in your marriage. The game of your own health has no end point, the goal is to keep the game of good health going for as long as possible. Your life cannot be “won” according to a universal set of rules, leaving everyone else as losers, because all players in the game of life are free to choose their own rules and success criteria to play by.

“Finite players play within boundaries; infinite players play with boundaries.”
- James Carse

So, you may ask, what has this got to do with entrepreneurship? To answer that question, let us consider two distint types of players of the entrepreneurship game.

Finite and Infinite Entrepreneurs

Some entrepreneurs are only in the entrepreneurship game for their current case, startup or business opportunity. If or when their current company either fails, IPOs or gets acquired, they intend to quit the entrepreneurship game and do something else (golf, typically). These entrepreneurs play a finite game which started with their idea, and will end when it reaches either failure or some predefined notion of success. That will be the end of it.

Other entrepreneurs are playing an infinite entrepreneurship game. These are often called “serial entrepreneurs”. When their current company either fails or succeeds, they will move on to the next one, then the next one after that, and so on. They are in the game forever.

They are committed to the path, the principles and the lifestyle of entrepreneurship, but they are “case agnostic” – they can take their entrepreneurial drive and tendencies elsewhere and apply it to other cases, other startups, other problems to solve. These people are infinite entrepreneurs. 

For infinite entrepreneurs, there is no defined “end game” if you look at a long enough time horizon. Sure, their current company might have an end game, such as an exit, an IPO or to hit some kind of KPI target, but this merely represents a finite game within the infinite game of entrepreneurship for life. 

“Finite games can be played within an infinite game, but an infinite game cannot be played within a finite game.

Infinite players regard their wins and losses in whatever finite games they play as but moments in continuing play.”

–James Carse

Stay Alive and Keep Making Bets

Lets us now return to my six-word entrepreneurship philosophy mentioned at the beginning of this post.

Since infinite entrepreneurs are playing a game where the goal is not to win, but rather to keep playing the game, it makes sense to “stay alive, and keep making bets”.

The practical, day-to-day meaning of this short statement is clear: when making choices, prioritise first and foremost to stay alive, and secondly to make bets on ideas, startups, products, services or people with a positive expected value.

When I say “stay alive”, I mean “preserve your ability to keep playing the entrepreneurship game tomorrow”.

Enough with the metaphors, though – what I mean in practice, is “never bet everything”. Never make decisions that can wipe you out of the game, because if that happens, you cannot continue to play. 

For some people, this may mean “never bet the company”, because if your company goes bust, so does your immediate platform for making bets and playing the game of entrepreneurship. This is also the most practical way to interpret what staying alive means. As an entrepreneur myself, this is how I personally think when making decisions in our company on a day to day basis.

However, it is not quite accurate, because truly infinite entrepreneurs are not only case agnostic, but also company agnostic. If, for example, my colleagues and I decide to go all in and “bet the company” on a decision which turns into a sour outcome and Braver goes under, I as an infinite entrepreneur will soon enough find a new idea, try again, rebuild, so long as my entrepreneurial drive is intact.

Therefore, the correct rule of thumb may not be “never bet the company”, but “never bet your own entrepreneurial drive” – never burn out so you lose the spark that keeps you coming back to the game over and over again.

This leads us to the final point of this post, which is the inherently positive expected value of “making bets” in entrepreneurship. Let us compare a gambler’s betting prospects to an entrepreneur’s to illustrate this. 

Casinos vs Startups: Where to Bet Your Time and Money

Contrary to popular belief, casinos do not want you to lose all your money to them, at least not on your first visit. If you enter the Bellagio and immediately get hit with a massive, my-wife-will-kill-me-type loss, you’ll probably leave with your tail between your legs and promise yourself to never ever come back. If you instead enter the casino, win a little, lose a bit more, but continuously feel like you have a good time, you may come back again and again and keep making bets.

Since the house always wins in the long run, the most profitable strategy for the casino is to get people to come back over and over again, bet moderately on every visit, and let the visitors bleed out slowly, metaphorically speaking. Unless you are exceptionally talented at various betting games, it is a losing strategy to keep making bets in the casino, because the expected value over a long period of time is negative. 

Entrepreneurship on the other hand, works in exactly the opposite way. If you believe in your own ability to create and capture value, and in your own capacity to get better at value creation over time, then continuously making bets in entrepreneurship has a positive (and ever increasing) expected value. If you make those bets on ideas, products or services that can scale, this is even more true. As they say in venture capital (and in NFTs… 👀), you only need to be right once – one big hit can cover all your previous losses and make you rich to boot.

Invite Serendipity to Strike

The underlying belief behind “stay alive, and keep making bets” is that good things happen to people who put themselves out there, who pursue meaningful and valuable opportunities despite the inherent risk of failure in any and all new pursuits.

Such “good things” may not happen immediately, but with continued, strategically sound and ethically right efforts over time, I am fundamentally optimistic about good things ultimately happening. In short, I believe serendipity will show up one day if you just keep on inviting it in. 

This belief colours how I navigate my own life. It is a surprisingly useful aid in everyday decision making, both in my personal life and at work.

I want to keep my health intact, not only for the sake of having good health in and of itself, but because being healthy allows me to do things I find meaningful and to live a fulfilling life. In other words, I play the infinite game of health so I get to keep playing it for as long as possible. 

Similarly, we want to keep our current company alive, but not for the sake of its existence in and of itself – we want it alive so we can use it as a platform for experimentation and for the pursuit of interesting opportunities that can have a positive impact on the world and on ourselves. In other words, we are playing the infinite game of entrepreneurship. I can strongly recommend you to try the same if you’re entrepreneurially inclined.

Have a great week,

-Jacob