On Real Confidence

In my early 20’s, I was stupidly confident. That type of stupid confidence that leads you to say things to people that you regret in your 30’s, that type of stupid confidence that isn’t really confidence at all, but is more a symptom of overwhelming insecurity. The kind of confidence that whispers in your ear, just do it.

Although I refer to this confidence as “stupid,” it actually led to a lot of interesting opportunities, many of which define who I am today. There were a lot of bold moves that resulted in nothing, like one time I tweeted a half finished song at one of my favorite singer-songwriters to see if he wanted collaborate (he turned me down, but I ended up opening for him a few years later in DC). Another time, I emailed the CEO of IBM to ask if I could interview him on my podcast (he never wrote back). With every “no,” my confidence only got stronger somehow.

But there was one time that I’ll never forget, one instance where I came face to face with just how stupid and small my confidence really was. It was when someone actually responded to one of my crazy requests.

There was an up and coming blogger, who I won’t name because they might see this post (not that it would matter at this point). This was about 12 years ago. At the time, I was realizing just how reachable people were on the internet, after having my emails returned from mammoths like Seth Godin.

This blogger had written about the idea of a one-sentence daily journal, and I emailed her to ask if I could code up an electronic version of the one-sentence journal for her for free. My idea was that we’d create this relationship, this partnership, and it could lead to other important opportunities later on.

I expected a “no.” But she wrote back with a “let me think about it.” And eventually, a “yes, let’s do it.”

And that was the last time we communicated, 12 years ago.

I froze up. I realized I was in over my head. And maybe I wasn’t, maybe I had the coding skills to make this happen, but at that moment in time, I didn’t believe I did. So I never wrote back.

And that blogger is now a celebrity, with many bestselling books and a podcast and everything else. And I’m not saying I regret not writing because I would’ve been associated with someone important. But it does make me think about what real confidence is.

Real confidence would have looked like honing a craft, of writing program after program and failing over and over again, of having an actual record of success rather than just a commitment to “grinding.” We talk so much about just asking, just reaching out, just saying please. It takes a second to get over the fear of emailing someone, but it takes years to become so valuable that someone emails you.

If we can’t deliver on our promises, all the assertiveness in the world won’t help. Real confidence isn’t what you say, it’s what you do.