Let’s Talk About Anxiety, Fear of Failure, and Why I Didn’t Go to The Dentist for 27 Years — This is going to be BIG

This week, I got my wisdom teeth out—all four of them.

You might be wondering what took me so long. I’m 45 and most people have them out between the ages of 17 and 25.

One helpful bit of context is that until very recently, I hadn’t been to the dentist since 1998.

Here’s what happened…

I never had a cavity growing up. I did a lot of things pretty perfectly growing up—straight A’s, never got into trouble, never started drinking, etc., and I got a lot of love an affection from my parents because of it. They never put a lot of pressure on me to be perfect, but it seemed pretty clear that my winning streak became something of an expectation. In fact, their affection seemed so tied up in my outcomes, that I began to dread what would happen if I failed at something.

Small missteps felt like big disappointments to them—that time I lost a $20 bill on the way to the store to buy some bread. There was that geography test in the second grade that I got an 80 on, because I kept confusing Ketchikan, Alaska with some other Alaskan city—one was a fishing down and in the other they trapped fur or made paper or some such craft. For the life of me, I kept swapping one for the other, and relative to my other performances, totally bombed. Once, I left a jean jacket in a park after baseball practice.

All of these things were met with disappointment, which seemed unbearable at the time compared to the normal radiant glow of their affection, particularly my mom’s.

This was only compounded by each visit to the dentist where the result was, yet again, no cavities. That made the pressure to keep it going more and more. I began to dread the possibility that I might have one each time I went until, one day, when I was out of the house and it was up to me to set my own appointments…

I just never did.

There was never a moment where the anxiety around going allowed me to pull the trigger on my own. It was never something that I wanted to do—so everyday, for 27 years, I never did.

Don’t get me wrong—I knew that taking care of my teeth was important. I flossed daily, had all manner of water picks, electric toothbrushes, etc. I even bought my own scraping kit with all the little tools and the dental mirror—but I never made an appointment.

I couldn’t.

I came close. When my wisdom teeth came in over the years, there were a few days here and there that the pain got so bad that had I woke up feeling as bad as I did the next day, I was going to do. Ultimately, it subsided.

This is what I know it feels like for a lot of founders and investors alike—floating in the rarified air of extremely successful people defined by their outcomes. I can’t tell you how many times I got announced as a successful VC when I was introduced on a panel or sat across the room from a potential limited partner telling them I was. It’s easy to get success so wrapped up in your own identity that any kind of deviation from the biggest outcome, let alone actual failure, would mess with your sense of self.

What changed for me?

Two things…

First, as my venture track record has matured, while there’s still lots of opportunity for upside and returns to my investors, I’ve had to come to terms with the fact that my outcomes weren’t the kind that I had hoped for. I could spend lots of time dissecting why, but I’ve had to shift my self image from, “Good at this” to “Worked really hard to be good at this”, which isn’t the same thing, but something that I can be proud of regardless of the outcome.

And secondly, I got showed up by my three year old daughter, who took on her first dentist visit like a champ.