Letter to a Burned Out Founder

Dear Founder,

Burnout sucks. It is an insidious parasite that festers underneath the surface. You might not even notice it growing until the day you wake up and realize that you are underwater.

Burnout robs you of your joy, your will, and your abilities to do your highest calling.

And even if you are aware of both the fact and the consequence - more likely than not, you will continue and push forward. Because to do otherwise would mean acknowledging that you are burned out. And that weight is too much to bear. So you put off the day of reckoning and continue working. But the burnout is still there. Collecting interest. And it will come due.

The Two Phases of a (Venture-Backed) Startup

Burnout often happens in the "early" part of the startup journey.

This part is marked by two distinct phases:

• the phase before product market fit (PMF)

• the phase after PMF

The action of pushing a boulder up a hill is used to describe the phase before PMF. It is grueling work and you're not quite sure who will win in the end - you or the boulder.

The action of chasing a boulder down a hill is used to describe the phase after PMF. This is a different but equally hard sort of work as you run as fast as you can just to keep up with boulder.

This letter deals with burnout that can occur pushing the boulder up the hill.

The Burnout

I came across a recent hacker news comment that described burnout as an inequality between "resources", "agency", and "care".

Resources describe what you have at your disposal to achieve a particular outcome - this usually is some combination of personal capabilities, capital, and team.

Agency describes how much control you have over the outcome.

Care describes how invested you are in the outcome.

In big tech, the regular worker has access to near-unlimited resources but often very little agency. In a startup, the opposite is true.

People can burn out in big tech because they care about the outcome but have little agency in controlling it. In startups, founders burn out because they care about the outcome but run out of the resources necessary to achieve it.

As a startup founder, you make up for the lack of resources by being agile. By doubling down in a few key areas and executing extremely well. By putting in sweat, blood, and tears to push your idea forward.

In the phase before PMF, all your effort is concentrated on pushing the boulder up the hill.

When Push Leads to Burnout

Burnout happens when you push the boulder up the hill for too long with little progress and no end in sight.

Maybe you're pushing the wrong boulder (your boulder is made out of lead). Maybe you're on the wrong hill (consider going up the one that isn't covered in snow). Whatever the reason - you come to realize that this boulder is not going anywhere.

Meanwhile, you've already spent years (and capital) working on this boulder. Your "resources" are running low and prospects are drying up. What do you do?

This depends on your mental model of "doing a startup".

Striking Gold

One mental model of doing startups is that of "looking for gold".

Imagine a prospector searching for gold. He or she will continue forward because success comes with finding the gold. There's always the chance that the next dig will lead to the mother lode and they can exhaust all options to get to that outcome.

In startup lingo, replace the dig with the next feature launch. The next enterprise customer. The next influencer campaign.

In the "looking for gold" model, you are working for a singular outcome that will make you whole. Once you achieve it, all your problems go away.

This isn't the case for startups. Say you do "find gold" and make it to the top of the hill. Your journey is not done. Finding PMF means that it is just beginning. Now the hard work of chasing that boulder down the hill begins.

The average SaaS company takes 9 years to exit. Even if you think you can push that boulder to the top by sheer force of will, can you continue for another five to ten years if you've already burned yourself out getting there?

Infinite Games

Another mental model of doing startups is that of an "infinite game".

The concept of an infinite game is discussed in the book Finite and Infinite Games. A finite game has an end and players play to end the game. An infinite game has no end, players play to continue the game.

While venture-backed startups can seem like a finite game with a set end (aka exit) in mind, it's not helpful to think of them as such.

This is because most startups fail - if you are trying to measure success by the outcome of any one startup, it is like a gambler going all in on a single round of roulette.

If you do your startup with this mindset, you will continue pushing that boulder even if it is made out of lead. Regardless of whether you make it past the hill, you will probably burn through all your resources getting there, causing the "game" to end.

By "game", I'm not talking about the current manifestation of your startup. Rather, I'm talking about your spirit. Your passion. Your ability to continue playing the game.

Your odds of "winning" the game become much higher if you play the "infinite game". In doing so, you detach yourself from the outcome and invest in the journey. It means being willing to fail, learn from mistakes, and start over if need be. It means taking care of your "resources" because you are playing the "infinite game".

Taking a break

If you identify yourself as someone that has pushed a lead boulder up a snowcapped mountain for much too long, you have a few options.

You can keep pushing and hope you strike gold soon. And hope that in your current state, you can last another five to ten years chasing that boulder.

Or you can choose to step away. Take a break. This means walking away from your startup for some time. A week. A month. Maybe even a year. Whatever you have to do to restock your resources and rekindle the original excitement that got you here in the first place.

Of course, this is much easier said. This comes as naturally as eating nails. It feels like giving up. Of letting down everyone - your customers, your team, and your investors.

But take the other side of this argument. Say you continue pushing forward. The success of a startup is determined, in a large part, by the team behind it. The earlier and smaller the startup, the more of an outsized impact the founder will have in that team and hence the startup. Given the dismal odds of most startups succeeding, how likely will it be for your startup to do so if you're already burned out?

Continuing to push forward at this point is like the airport making people take off their shoes in the security line - playing along for appearance's sake vs actually addressing the real issues.

Sometimes the only way forward is to step back.

Are you burned out? If so, consider taking a break. The game will still be there when you get back. As long as you are still willing to play.