Disappointment

My co-founder and I were at the offices of one of the largest Parisian VC funds, pitching our company in front of two fund partners. At the middle of the pitch, the more senior one stood up from his chair and started yelling at us. He said that our company looked like it was following a path of Critéo, and how it was exactly the type of poor returns “success” story that their fund was determined never to invest in. He was so angry at the other partner for even brining this opportunity to them, and for wasting his time with us. At the time, Critéo was already one of the greatest successes of the early Parisian startup ecosystem, having their IPO on Nasdaq. They earned x20 — x60 returns to their investors. I simply thought the man was crazy to expect more, and I couldn’t explain his resentment. How could he consider such as success a disappointment?

It got me curious about disappointments, and I soon realized disappointments were everywhere around me, sticked to my back and to my forehead. When I achieved my long-awaited goal, sold my startup, my mother’s reaction was an emphatic “… and what will you do now?”. No pride. No praise. Disappointment.

Disappointment results from unmet expectations. We often look into disappointments through the prism of expectations (expressed or hidden) that cause them. And we are easily tempted to dismiss the disappointment of others as their fault, for having unrealistic expectations. But the truth is more complicated than that.

Disappointment follows founders like a shadow. Founders catalyze hope. The courage it takes to dare having a goal is magnetic. It attracts people. With them, it attracts their own desires and hopes (often unrealistic or unrelated with the founder’s goal) that they project onto the founder. We all do it.

There is a mythical component to being a founder. The hopes that people project on you propel you, and at the same time cause disappointments.

In an interview to Vogue Homme, the famous French actrice Catherine Deneuve said : “It is a trap to believe in your own myth. It condemns you to live what others project on you”.

You’ll definitely do yourself a favour if you are very explicit about your goals, if you write them down for yourself and if you communicate them clearly to others. You can also try to spot the stealth expectations and manage them. But it won’t prevent the disappointment. It just comes with the job and with the mythical role of the founder — catalyst of hopes, a promethean figure, the one who brings the fire (a.k.a. hope) from gods to the people.

Disappointment are viral. When you disappoint, you get disappointed. At the very least, you’ll be disappointed when you discover the stealth (often dehumanizing) expectations people have from you. But often, the very feeling of having disappointed someone will just trigger other disappointments in you and raise your level of awareness about things that aren’t as you expect them to be. No wonder we so desperately try to avoid disappointing people.

When making startups, there is one disappointment more common than others: even if you do everything right, play in a big and growing market, build the best team, have the best product, find the best investors, you may still fail. You are simply fighting against the odds. When you win, the reward is high, when you fail you get disappointed.


Do not think you can be brave with your life and your work and never disappoint anyone. It doesn’t work that way. — Oprah Winfrey

Disappointment is an emotion. As every emotion, it is necessary for some of the key functions of our brains and plays a part in realisation of some of our cognitive capacities. The modern culture (especially in business) compels us to fight and suppress our emotions. By doing so we are directly working to diminish our cognitive potential, because each emotion is valuable for something. Disappointment is valuable to shape our view of who we are and who we are not, of what we control and what we don’t. It liberates us from projections, from believing in our own myth, and sets us free to live our own lives.

It’s only when you start failing as a myth, that you can succeed as yourself at your own goals and the goals you set for your startup.

Being a founder means daring to dissapoint.

Normalizing disappointment

Every time you’re given a choice between disappointing someone else and disappointing yourself, your duty is to disappoint that someone else. Your job throughout your entire life, is to disappoint as many people as it takes to avoid disappointing yourself. — Glennon Doyle, Untamed

Living with the possibility of dissapointment is not only a matter of reality-checking our expectations. Disappointments are so natural in the startup life, that we not only fear them — we anxiously dread them.

We normalize disappointment by being open and proactive about it. It means checking out whether our past disappointments have affected our audacity to aim for new ambitions. It means reminding ourselves what is worth trying even if we fail. It means knowing who we are and being who we want to be in challenging situations. All of which is hard.

Here are some of the questions I find useful to ask myself:

  • Who expects me to be something I am not or do something I won’t do?
  • For a particular goal, am I setting this goal to get the most of my potential and my situation or am I calibrating my goal to avoid disappointment?
  • If I fail at my goal and get disappointed, what is the story I want to be able to tell myself? What is the story I want to be able to tell to people who supported me?
  • How can I take advantage of the founder myth when it serves me, and reject it when it doesn’t?

Subscribe to The Founder is Present

Don’t miss out on the latest issues. Sign up now to get access to the library of members-only issues.
jamie@example.com
Subscribe