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Admitting When Things Aren’t Perfect

No you’re not perfect but you’re not your mistakes. — Kayne West

We tend to have a hard time admitting when things aren’t going great. When I talk to a founder and I ask them how things are going, the answer is almost inevitably, “Everything’s great.” And then you find out a few months later that they’ve run out of money.

Things usually aren’t great. That’s because startups are usually failing by default. And even when things are going great, there are always one or two things that aren’t. When you’re a founder, those are the things constantly on your mind.

At Y Combinator, Sam Altman once told us that there’s a negative correlation between how well a founder says their startup is doing, and how well it’s actually going.

So why do so many people lie about how things are going?

Well, I think it’s a lot like when people ask you how you’re doing, and you say you’re doing fine, even when you’ve had a tough day. Sometimes it’s just not something you have the energy to fill people in on.

You should get over that though.

You should get over it for two reasons. First, when you share your problems and imperfections with people, you open yourself up to the possibility that someone else might be able to help you.

When you share what you’re going through with others, they may be able to help you by introducing you to people, sharing resources, or even just helping you see the problem in a new light.

That’s was one of the biggest benefits of doing office hours at Y Combinator. Even though the partners would often give us radically different advice, it sometimes helped us see things in a new way that we wouldn’t have been able to before.

Second, when you open yourself up and share your problems, vulnerabilities, and things that aren’t going well, you are humanizing yourself and creating an opportunity for others to connect with you.

That’s one of the paradoxes of leadership, you can be strong through weakness. Vulnerability can be inspiring.

Michelle Wetzler at Keen.io once wrote a great post about giving yourself permission to fail, in which she says something amazing:

To give yourself permission to fail, you have to untangle your ego from your work. Having your ego tied up in your work is a handicap. You can’t think strategically or take risks when you and your personal well-being are on the line.

I used to (and sometimes still do) romanticize Keen a little too much, thinking of it as my child, a part of myself. I’ve been working hard to untangle this. Not because I plan to care any less about Keen, but because I don’t want my ego & personal fears to get in its way. Keen and Michelle are two different things, or at the very least they are less overlapping than they used to be. If Keen is struggling, it need not mean Michelle is struggling. If Keen is taking a risk, it need not mean my happiness is on the line. It also means checking my ego and admitting (with some difficulty) that even if I fail completely at my job, Keen is going to be just fine. And, that if I fail completely at my job, that I will be just fine. It just means I tried something too difficult for me, or my assumptions were wrong. That’s ok too.

And this is incredibly true for almost every startup. Founders entangle their success with the success of their company. They assume that if people think their company isn’t doing well, that it means they’re not successful as co-founders. They continue thinking that until they go out of business.

The biggest danger is that by not talking about the things that are going wrong, I think founders are putting themselves in a mentally dangerous position. They’re alienating themselves from the very people around them who care about them and want to help them the most.

I’m reminded of the tragic story of Diaspora co-founder Ilya Zhitomirskiy who committed suicide at the age of twenty-two. Reports linked pressure related to the startup to his death. His mother said “I strongly believe that if Ilya did not start this project and stayed in school, he would be well and alive today.”

It’s shouldn’t be all that serious. People fail, and that should be alright.

So the next someone asks you how things are going, instead of saying the usual, “Everything is great,” try to take a moment and think about how things are actually going, and then share. You may find that people thank you for it. At the very least, you might thank yourself.