One early summer Sunday afternoon we were having lunch by the sea in Glyfada, suburbs of Athens, Greece. Few tables from us, there was a family — a man in his mid-thirties and his parents, also having lunch. They ordered an expensive fish and a nice bottle of wine. We knew they were a family because the son clearly looked after both his father and his mother. It looked like that slow, idyllic stereotype family lunch — a son, not yet married, taking his parents out on a Sunday lunch. It’s just how you imagine those “happy families” from Tolstoy’s quote that opens Anna Karenina: “All happy families are alike, but every unhappy family is unhappy in its own way”.

We were compelled to go further in our inference. The son had the alure of someone well educated and was dressed like someone who earned well. He didn’t have the sharpness of a finance guy nor the malice of a lawyer. So, we concluded he must have been a young doctor. But young doctors don’t earn well, unless they’ve inherited the practice from their parents. And here at the table we had the father who looked like a newly retired doctor. The man had the whole posture of someone on whom many could depend — aware of his importance. But not the kind of importance driven from power — rather the skill/knowledge kind. The father and the son were clearly having an intellectual debate, there was both complicity and argument in the air. Nothing important, probably politics or other first-world problems.

The mother was silent but very present. She nodded at the arguments of both the son and the father. She had her nails done, and she freshly came out from the hairdresser. She looked proud of both her men. But clearly, she thought it wasn’t her place to participate in any intellectual debate. She had the hands of someone who never worked or at most she might have been her husband’s secretary. But clearly, she looked like someone uninterested in money or accomplishment other than that of being a mother and a wife.

We’ve got it all figured out, so proud of how our knowledge of stereotypes and experience of life allowed us to understand so distant people. The lunch was over. Desert eaten. The bill arrived. We knew the son would pay. And then, the woman stood up. We were convinced she would go to the toilet while the men settle the bill. She opened her purse, took out a beautiful wallet, paid the bill, then she took out the keys of the car, and had the two men jump in on the back seat as she drove them away.

Our jaws dropped. We laughed so much. At ourselves. We still laugh when we think of this.

Being a computer scientist, I know very well about the limits of what we can know. I also know those same limits are what compels us to try and come up with explanations for things that we don’t know. When we feel a gap in our knowledge, we are driven by some form of urge to fill this gap. That is what drives the very basic process of learning.

Coming up with plausible explanations is what our minds do all the time when there is something we don’t know. Often, before we can get curious and dig deeper, our mind has already made up an explanation.

Founders get to regularly deal with the unknown and get to make decisions in total uncertainty. My experience as a founder has made me aware of two particularly interesting types of truths that work together against me: the unknowable truths and the uncomfortable truths.

The Unknowable Truths

There are truths that we can never know. We know that they exist thanks to Kurt Gödel who has proved it almost a century ago, and then thanks to Frederic Fitch and his Fitch’s paradox.

What it means is that our ability to know anything at all is in fact bound to the limits making some truths simply out of scope of what we can ever know. Frustrating, right?

In my experience, many of the unknowable truths are in fact answers to the questions that start with “Why…”.

There are generally unknowable truths, and there are truths that are unknowable to you at a particular moment. Things that, even with all imaginable information, you simply can’t know.

I noticed that that is where my mind gets particularly active with coming up with explanations. Why did a particular VC fund turn me down, but invested in another startup, much worse than mine? Why did the client choose an alternative product? Why did a client not buy my product but said they needed it?

You’d be surprised to learn just how often even those who turned you down don’t know why they really did it. They can come up with an explanation after the fact, but they have no idea what actually made them act the way they did.

The Uncomfortable Truths

Among the truths we can actually know there are truths, often staring right at us, that we don’t want to know — the uncomfortable truths.

They are uncomfortable because they might lead to disappointment, or because of the way our notion of self-worth is constructed and can be challenged. We do everything in our power to look the other way and not grasp the uncomfortable truths.

Scientists love uncomfortable truths. If science was a game, the winner would be the one finding the most uncomfortable truth. Artists often play with  them too. I find that art can often act a form of anaesthesia for the discomfort of the truth it conveys.

In order to move towards their goals, founders must look straight into the eyes of the uncomfortable truths. They must acknowledge the uncertainty of revenues, uncertainty of performance of employees, unpredictability of the future, tentative nature of plans, etc. There is no anaesthesia for it. Being a founder means having the courage to lean into discomfort.

Even the smartest, most experienced, and well rested person often falls under the spells of unknowable or uncomfortable truths.

Often, we need some sort of working assumption about the things we don’t know, some model of reality that allows us to make quick decisions. This kind of stories we tell ourselves are actually useful as long as we are aware and able to unlearn them and replace them with new perspectives when needed.

Getting aware of the things we can’t know and of the stories we told ourselves instead of admitting we don’t know can be a realy healing experience. When we see what a story we told ourselves can do to our lives and how it can narrow our options, we are quick to embrace the uncertainty and unpredictability of our situations as founders. I’ve taken a lot from ackownedging the unknowable truths — my assessments of risk have benefited from it as well my self-confidence.

As for discomfort, the best strategy I’ve found so far, is to associate the discomfort with movement. I’ve learned to associate the comfort with some sort of stagnation, with numbness, with being stuck. I now perceive the discomfort of the uncomfortable truths as the feedback of movement — some sort of friction inherent to movement. When you walk the friction you feel with the ground gives you feedback so you know where you are. That is the same thing that the uncomfortable truths do for us on our journeys as founders.

Normalizing the unknowability and discomfort of truth

The negative effect we experience from not being able to know, or from not wanting to know, is that we put so much effort into handling it that we are not really seeing what we can and should be seeing.

In order to focus, I ask myself the following questions:

  • What presents to me as a dilemma (a choice), that is in fact just an uncomfortable path with no real alternative?
  • What options that I have am I not seeing? What is being hidden from my sight by the gap in my knowledge or by the story I told myself in order to fill that gap?
  • Am I being stuck and obsessing over “How I got here?” rather than looking forward into “What can I do to get going?”

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