Let's Talk About Anxiety, Fear of Failure, and Why I Didn't Go to The Dentist for 27 Years

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.

If she could do it, so could I.

Plus, it’s part of a bigger theme over the last couple of years of taking care of myself for her sake. I had my first kid at 42. I want to be part of her life for a very long time. I’d like to have grandkids and be able to enjoy them—so when I’m still setting half marathon PRs or going in for a colonoscopy, I’m doing whatever I can to make sure that I’m going to be there for her.

And that’s a more important goal than never having a cavity, investing in seven unicorns, or IPOing a company—all things that result a little from your own effort and a lot from things you can’t always control, like the efforts of others and a whole lot of luck.

If you’ve started a company, and things aren’t going well—the best thing you can do for your startup, your investors’ money, and for your own mental health is to ask for help. Everyone knew the risks going in. You don’t owe them success, but you do owe them honesty, transparency, and a willingness to share enough information with others to enable them to help you.

That’s not something every founder feels is going to turn out OK, especially female founders and those from underrepresented groups who feel like they were under a lot more scrutiny to begin with, and who feel less likely to be able to land on their feet.

Things haven’t gone perfectly for me professionally, but in my failures I’ve learned enough to be able to continue my career as a VC coach and fundraising consultant able to help others.

And yes, I still have my no cavity streak going all these years later.*

*In the 28 teeth now remaining in my mouth. Former occupants don’t count in my book.