In love of hopelessness

“The gods had condemned Sisyphus to ceaselessly rolling a rock to the top of a mountain, whence the stone would fall back of its own weight. They had thought with some reason that there is no more dreadful punishment than futile and hopeless labor.” — Albert Camus, Sisyphus

A few weeks ago I was sitting in a meeting room together with the cofounders of a company we had been working on for almost two years. Despite some promising signs and a lot of effort, the product had failed to show any visibile traction. We had agreed a month earlier to look for alternative directions and there we were, sitting together in the moment of reckoning. The painful conclusion loomed heavy in the room: it was time to throw in the towel.

This is not one of those “why we failed posts”. I am not a big fan of them, but that’s another story[1]. No, what that episode got me thinking about is how hard it is for us to see meaning in our failed attempts. How consuming the act of trying is.

At Founders, we have always stressed the advantage of being able to separate what you are working on from who you are: that companies can fail but people shouldn’t. Four years in, this remains an assumption. In real life, we have noticed that once a company goes down it’s just too difficult to immediately jump back on the saddle.

I was talking to one of the co-founders and suggesting a bunch of other things he could try. From my privileged point of observation, I couldn’t understand what was so difficult in seeing as a “normal” job the process of trial and error until finding something that works. Listening to his replies, I realised that what is daunting is not failing, it is spending a life searching.

The real issue with product market fit

Product market fit is a fickle concept. It can be lost, it keeps moving, and contrary to popular belief, things don’t get magically easier once you get there. Yet, even discounting for its vague definition, it is fair to talk about life before and after product market fit.

Founders who have been through it describe it as an “emotional grind”, telling stories of stress, loss of sleep, loss of weight (and, even worse signs of mental and physical distress). It is more than just the hard work. Hard work itself becomes a relative concept depending on where the company is. Burnout is not a function of time, but one of movement. Forcing something that doesn’t work drives burnout, while the excitement for having (finally) found something that people want pushes everybody to give more.

We have been in this situation multiple times, and watched others doing the same. There is something exhausting about the uncertainty, the lack of positive feedback, the feeling that you are not progressing but endlessly circling back. It is a state of mind worse than the fear of failure, to the point that throwing the towel starts to be seen as a liberation. Not the dreaded moment where the world crumbles on you, but a break from the pain of futility and hopelessness.

The feeling of uncertainty, not the fear of failure, is also what blocks most people from getting started. It shows up as the perceived need to find a good idea, to validate the problem, to eliminate risk — all before jumping in. The big fear is finding out that we are toiling in vain, spending days, weeks, months on something no one wants. It is a vicious cycle: we don’t want to start before we know what will work, but without starting there is little chance to discover what that is.

Successful startups are built by two types of people: those who know how to manage the search and those who are naive enough not to care about it. We can keep relying on the latter, but we would be doing a good job if we could create more of the former. More specifically, we have to build a case for trying.

An economic case for trying

At the individual level, a lucid argumentation for trying comes from Paul Graham. In “After the Ladder”, he makes an important observation about the (micro)economics of a predictable career:

Economic statistics are misleading because they ignore the value of safe jobs. An easy job from which one can’t be fired is worth money…

The near-certainty of a long, uninterrupted career, followed by a generous pension is comparable, in NPV terms, with scoring a big financial win early on in our life. The social pact between employers and employees around the ladder made it rational to forgo the allure of a potential big win for the stability of a steady job. Conversely, if this promise disappears it would be far more rational to attempt reaching long term financial safety by making the most of our wealth early in our life[2].

We are accustomed to see our working life as a linear progression. We start humbly but expect to see our position and wealth grow over time. This approach has multiple implications. Betting our lives on careers means jumping on whatever is most in demand at that point of time. Our only reference to project a career path is to look at others who have been through it. By definition, it means betting on careers that are already 20–30 years old. In addition, our expectation for increased wealth pushes us for upgrades as we climb the ladder. In doing so we commit ourselves to a certain life, entangled in debt and irreversible choices.

Embracing a life of searching can seem irresponsible. Even Paul Graham limits his comparison to the extreme cases: the safe job and the early win. There are lives in between. Careers assumed to be safe are ended abruptly leaving people in shock, unable to stand up again. Others keep searching for that win, but never find it. What choice is better? Trying provides the optionality that careers remove. It allows us the early slack to focus on what’s coming instead of what has been. It keeps options open and burn rate low. As the two tracks progress, the economic value of a career is locked down, the range of outcomes ever narrower. Continuous searching, even the unfruitful kind, leaves that door open for serendipity.

Despite the obvious risks, trying can be a rational economic choice for the individual. Its value, however, becomes even more apparent when we turn our attention to the aggregate, the macro.

We all understand intuitively that an economy of outliers favours a portfolio approach. Over many bets, one will yield disproportionate returns, covering for all the rest and more. We use metaphors like racing and natural selection, pointing to the fact that many attempts are required to produce a winner. But we often fail to appreciate the real meaning of “required”.

Natural selection, in particular, is often misunderstood. When talking about “survival of the fittest” we get the idea that the fittest can exist in isolation, that all other players are background actors in a movie that doesn’t need them. The need for a portfolio is driven by our inability to see through the noise and identify the fittest. We wouldn’t need a portfolio if we could predict the future. That’s an illusion. When we focus all our attention on the outcome of evolution we overlook the process at the core of it. Biological life is a learning machine. Each attempt contributes to the whole, revealing closed paths and indicating open ones for others to pursue.

Learning from biology, we can understand economies as evolutionary systems driven by a process of selection, variation and replication:

“Evolution creates designs, or more appropriately, discovers designs through a process of trial and error. A variety of candiate designs are created and tried out in the environment. Designs that are successful are retained, replicated, and built upon, while those that are unsuccessful are discarded.”
”From the perspective of an entrepreneur or a new entrant starting in the low valley of a new architecture, there are lots of ways up and many new, untried peaks to explore. Most attempts up from the entrepreneurial valley will wind up in dead-end canyons or on disappointing short peaks. But with enough explorers working away, someone will eventually find an attractive route up.
Eric Beinhocker, The Origin of Wealth

This collective climb is not a race between unrelated individuals. It reminds me more of this scene from World War Z where zombies step on top of each other to climb the wall.

The question now is: what’s in it for the zombies at the bottom of the pyramid?

A modern Sisyphus

That’s where Sisyphus come in. There is a meme going around the web comparing a day in the life of corporate to that of a startup. We can skip the corporate guy in his hamster wheel and focus on the startup guy. He is depicted pushing a boulder up the hill, a clear reference to the myth of Sisyphus, condemned by the gods to carry a stone up a mountain just to see it rolling down again soon after.

I have seen these meme many times, recently in this tweet.

The issue with trying lies in the comment: “One gets you somewhere”. The truth is that most of the time it doesn’t. We miss the second half of the image, the downslope. Pretending to find relief from our Sisyphean toil in the hope of a result is perpetuating the same illusion at the root of our discomfort. What makes the search so miserable is precisely the expectation of progress, and the consequent feeling of despair when we realise that our work is without hope.

The solution lies instead in accepting our fundamental condition. For the French philosopher and existentialist Camus, Sisyphus is the ultimate hero. He has mastered the absurdity of a life without purpose and can now face his destiny with joy. As he walks back down the hill to pick up the boulder once again, Sisyphus is perfectly conscious of his fate. He resists despair not because he has hope, “to get somewhere”, but because he knows has not got anywhere.

“Each atom of that stone, each mineral flake of that night-filled mountain, in itself forms a world. The struggle itself towards the heights is enough to fill a man’s heart. One must imagine Sisyphus happy.”

You must try.

[1] Rationalisation doesn’t bring me solace from pain and I agree with the position that considers failure an overrated source of learning. Yes, we made errors and we picked the wrong turn in multiple places of the maze, but anything I could write here wouldn’t increase your chances of succeeding in the same space. Graveyard bias is not much better than survivor bias.

[2] This includes both starting a company and joining one very early (before product market fit)