Learn by Necessity

Reflecting on confidence, courage, and self-education

A few months ago I read an interview with Debbie Millman that included her thoughts on confidence: that it’s overrated and harmful, and that we should really be pursuing courage instead.

Confidence: Knowing you can be successful at something before you try it.
Courage: Knowing you quite possibly or most likely won’t be successful at something, but you try it anyway.

This idea I had trouble agreeing with. It stung, it was hard to swallow, and drove me into some periodical bouts of self-reflection. “Maybe Debbie has done some things, but confidence has always served ME well”, I mused.


But the idea stayed with me, incessantly prodding some corner of my brain until at last I reached a conclusion. The truth, I realized, is that I’d long been practicing confidence as a means of avoiding the fact that I really wasn’t very courageous at all. And Deb had called me on my shit.

After rewinding through all my projects and passions over the last few years, something became flagrantly, embarrassingly obvious—I hardly ever do anything 100 percent that I’m not confident about upfront. So, armed with insight from some guru mentors in my life I started seriously meditating on my priorities, and a different perspective started to make sense. I began to think of confidence as less of a virtue, and more of a limitation.

Confidence doesn’t make it easier to try new things

Instead, it makes it easier to do more of the same things, without facilitating self-improvement.

It limits your incentive to challenge yourself, or your drive to keep up with others in your field.

It discourages experimentation. It encourages close-mindedness.

With enough time, it can leave you stubborn and pretentious.

Learning by necessity

I’ve always believed the best path to education isn’t by studying and carefully picking apart methods taught by other people. Rather, it’s scribbling some notes on the back of your hand, sprinting into a place of complete uncertainty, and giving yourself no option but to hack your way out. The human mind can do incredible things and learn at remarkable rates when it has to. Necessity is good incentive.

But I suppose it’s easy to preach that kind of approach to learning when you yourself don’t apply it in a way that requires compromising your own security or financial stability. In other words, it’s easy to preach that kind of education when it doesn’t require much courage.

So this week I decided to practice growing courageously by turning down an opportunity: a job at a remarkable company operated by charismatic thought-leaders. People who are producing industry-leading work while genuinely doing what they love. The job would be challenging, educational, and gratifying, but it would also be safe. It would be secure. And while uncertainty necessitates growth, security pats it on the back, makes it some avocado toast and gives it a year-end bonus for participation.

Let me be clear: while on a path of security there’s nothing to stop you from growing. But there’s minimal urgency to do so. Taking a weekend off is easier when you can expect a paycheck on the 30th no matter how many users your product has gained.

So, instead, in a few weeks I’ll move to a new city with no solid plan, a readiness for the failures that will inevitably come, and a goal to keep growing Roof with my team. I’ll sprint in and leave no other reasonable option but to hack my way forward.

This week I turned down security in favor of uncertainty, so I could go practice courage. I’m brimming with excitement. I’m nervous as fuck.