Confidence

I had office hours with a founder who was struggling to rebuild confidence after a past failure. He was terrified he'd make the wrong decision and fail again, and he was paralyzed by it. It didn’t matter to him that his “failure” ended up landing him in YC - an objectively wild feat. This founder’s perception of his failure was his center of gravity and the only lens through which he could view himself and his current startup. His mind was completely preoccupied by it.

The thing about confidence is that it doesn't require any success - at all. Not at all. Rebuilding it doesn’t require you to take the 'right' action, you just have to commit to taking an action - any action - and then actually do it. On repeat. You don’t even have to believe you’re capable of performing the action you’re committing to. Self belief is not required. I’ve seen so many of my clients lay out a path for themselves that they truly had no idea they could execute until they were literally in the middle of doing it. These founders suspended self-belief and allowed their actions to show them what they’re truly capable of. Step by step, they astonished themselves.

It’s the commitment you make, then keep, that’s key to building confidence.

Another word for confidence is 'self trust.' You build it when you keep the promises you make to yourself. Start small: 'I'm going to write five lines of code today.' 'I'm going to email one user for feedback.' 'I'm going to cold-email five leads.' ‘I’m going to make one decision.’

When you first begin, this will require you to stay very, very close to the truth of what you’re capable of. This can be deceptively hard. The first goals you set should be simple. Elementary. And realistic. Begin with the minimum-viable promise that will get you moving in the right direction: Forward. Remember, your primary goal is to build your inner confidence with these actions, not achieve external success. I’ve had days where my only goal was to ‘breathe.’ I’ve worked with founders who committed to themselves that they would simply ‘eat.’ Both were the on-ramp to bigger commitments.

Let me tell you how keeping small promises will rebuild the psychology of the founder I met for office hours: He’ll set small goals and achieve them every day. This will retrain his perspective from being preoccupied by the past to being focused on the present. Over time, this redirects his psychological center of gravity away from his past failure and into the present where it belongs. This shifts resources - energy, attention, skill, will - that open him up to a new future. Second, our psychologies don’t make too fine a distinction between small and big wins, so his achieving many small goals in a row will give him a boost of self-esteem. A more technical way of saying this is that keeping many small promises will repair his ego by refilling it with self-trust. The ego is the part of our psychology that contains our personality and acts as the driving force of our will. So keeping small promises lets his ego practice living out the belief “I am capable,” and it will be true. This is the belief that we want him to bring into his new startup - and it’s how this simple practice unlocks profound change. The knowing that “I am capable,” in combination with a streak of kept promises, forms a new belief that supersedes the old belief he’s been carrying from his past "failure: “I’m not capable.” Our thoughts, emotions, and - most importantly for a startup founder - our actions all flow from our beliefs. By developing a new belief in his capability, this founder will find that more and more actions are possible. “I believe in myself” is exactly the kind of mindset you want a startup founder to have, because it allows for risk-taking, inoculation against uncertainty, and a regulated nervous system that can make sophisticated decisions quickly.

So with a relatively simple practice - making and keeping small promises - this founder will have healed himself from a past hurt and regrown the confidence to do justice to his new startup’s vision. He’ll find himself living in the present and focused on the future, channeling the fullness of his potential into his new idea.

When you’re rebuilding confidence, don't commit to more until you can trust yourself with bigger swings. (But I bet you'll be amazed at how little time it'll take to get there.) Stay focused on how good it feels to keep promises to yourself instead of how big or little the outcomes are. Repeat, be consistent, and increase the complexity and scope of your promises to yourself (then others) as you gain self-trust.

And if you’re in a phase of rebuilding, be intentional about the promises you make to other people. Don’t overextend yourself. Default to saying “no” for a short period if you need to, so you have the resources to make good on the promises you’ve made to yourself. (“I’m sorry, I can’t commit to that right now.”) It isn’t sane or reasonable to expect anyone else to trust you until you can trust yourself.

I imagine that some of you may have an inner critic reading this alongside you snarling in your ear saying something like, ‘This is ridiculous. These founders are weaklings and their startups must suck. There’s no way I can get to where I’m going if all I do is send 5 emails a day and breathe.’ You haven’t internalized yet that rebuilding confidence doesn’t require success or big goals - in fact, it’s often thwarted by them. The founder I mentioned above, who committed to ‘eating’ every day was a YC-funded Series B CTO in his third year of hypergrowth. He wanted to know that he could run his startup and take care of himself - to achieve his highest ambitions without forgetting the fundamentals of what he needed as a human being. He wanted to develop that inner anchor of self-trust as a jumping off point to feel confident and self-possessed when he stepped into the challenge of raising a Series C. He no longer defined it a “success” if his physical health was destroyed in the process of running his startup, but he wasn’t sure it would be possible to win without paying that price.

It was.

I have two responses to your inner critic, who’s motivated to help you succeed but who lacks the granular knowledge of how you’ll get there:

First, if you don’t trust yourself, you won’t get to where you’re going anyway. There’s too much uncertainty in running a startup and your lack of self confidence (about choosing a direction, deciding on a roadmap, committing to taking any risk, etc) will slow you down to the extent that you’ll never move quickly enough to win. Sometimes we have to slow down for our slowest parts. The moments when you need to rebuild trust in yourself is one of them. I’ve known a lot of founders who have suffered and whose startups have died because they got stuck in a tailspin of never trusting they could make the right call. They became anxious wrecks, shopped for advice from advisors whose varied advice confused them and made them stray even further from their own sense of truth, and who ultimately lost the faith of their users, cofounders, and team. I’ve never known a founder whose startup died because they trusted themselves too fully.

Second, the minimum viable promises I’m suggesting you set for yourself can always be exceeded if you’re feeling the good flow of things and want to keep going! If you’ve emailed one user for feedback and feel great about emailing the next five on your list - go for it. You’ve already met your minimum, should be relishing in how good it feels to keep a promise to yourself, and no one is stopping you from continuing. Just remember - you don’t have to, from the perspective of your confidence. But you certainly can, from the perspective of your performance goals. (If you feel like you should keep going then don’t. ‘Shoulds’ speak to an expectation someone else has placed on us, and obligating ourselves to others does not rebuild our confidence. It only rebuilds our capacity for compliance.)

If you had a day where you exceeded your self trust goals, remember to keep them very small and simple when you set them the next day. Make it easy for yourself to win again. Don’t let the extra work you did yesterday make you believe you have to increase complexity. Confidence is rebuilt faster when you consistently achieve small goals, and much less so when you rarely achieve big goals.

So? What promise would you like to keep to yourself today? Write it down. Email it to your cofounder. Then do it. And repeat this exercise tomorrow. Notice how good it feels not to give up on yourself. And please never stop.