Note: I wrote this essay as part of a large self-reflection on 2018. I read every one of my 80+ journal entries from that year. On 1/1/19, I sent this essay to a private email list of my closest people. After reading Jake Chapman's "Investors and entrepreneurs need to address the mental health crisis in startups,," I decided to publish it broadly.
I doubt myself a lot. Everyone is totally just winging it, all the time is one of my favorite articles ever. It makes me feel far less alone with my fears. Will my company be successful? Am I nuts? Are all my friends avoiding the trouble of telling me I’m working on bullshit? What if we're wrong about everything and this thing fails? Am I smart enough, good-looking enough, good whatever enough to find the kind of person I think I want to share my life with? Is it okay to end sentences with prepositions?
I struggle to trust myself when making decisions at work. In different scenarios, I can be quick to jump to a conclusion, trust my gut, and end up taking on unnecessary risk. I also overthink a lot of decisions. My investors have characterized me as “academic.” I know there's a Goldilocks' Zone in the middle, but I struggle to find it over and over again. I want to trust my gut, but I don't want to make a poor decision. I want to make decisions quickly, but I want to make the right ones. The fact that I both over-think and jump to conclusions in different scenarios makes this even more complicated, as there isn't a single solution. This year, I’ve learned that my gut is a great early warning system that I then need to verify to make sure I’m not just indulging in confirmation casserole.
I like to think that I think for myself. I’m pretty sure I barely think for myself. If anything, I know I’m good at taking in a bunch of ideas and blending them up into something different from its constituent parts. But way too often, I find myself thinking about what other people will think if I do this or that.
At the beginning of the year, I discovered the "know yourself" cards from The School of Life. One asked, "what are you trying to say through your clothes?" I spent a lot of my 20's trying to be someone I wasn't. I'd wear button-down oxfords because I was nervous about other people thinking I was too young. In reality, I thought I was too young. The "grown-up" clothes were for me, not for anyone else. They were a band-aid on a much larger self-confidence issue.
In the late summer and early fall, I read The Courage to Be Disliked. I struggle with some of the ideas in the book, like Adler's wholesale rejection of trauma, but this book helped me realize how often I—and others around me—live their lives on others terms. So often, we do what we think will please others. Whether it's because we desperately want to be accepted by a social group, break into a new social class, or something else, we spend a lot of time thinking about what others think of us. When we let others' views of us dictate the choices we make, we relinquish the agency we so convincingly pretend to cherish.
I graduated from Ohio State. It's a state school known mostly for football, parties, and the immense size of the student body (40K+). I graduated with something close to a 3.14—I was especially proud of that. When I got to Silicon Valley, someone—who will remain nameless—was a total prick to me and said he was shocked anyone was considering hiring me considering I didn't graduate from an ivy league school. I've always hated that bastard. A few years later, Harvard Business School did a case study on Mattermark and gave us a mug as a souvenir. That's my favorite mug. I have a complicated relationship with that mug. At once, I’m proud of it, but I also hate that I get satisfaction from the external validation. It feels dirty.
The combination of enough temporal distance from Mattermark and all the juicy goodness I’ve been learning building Holloway left me feeling a sense of shame late in the year. How could we have been so ignorant? Maybe I’m not exceptional. Maybe I’m destined to work in middle management somewhere. Maybe I’m destined for the misery I see painted on so many other people’s faces. Maybe their misery is really my misery and it’s unfair as hell for me to go painting without permission. I felt ashamed we hadn’t been able to make Mattermark work. We had the bull by the horns, and we just let it trample us. That’s what it felt like.
Instead of valuing all that I had learned from founding Mattermark at 23, I let it eat at me. I let it eat at me because I looked at others who started companies in the same period who succeeded and I envied them—poor little me, starting over again. Toward the end of the year, I began to look at my experience building Mattermark like a series of mistakes I now think I know how to avoid. But then there’s the specter of my self-confidence again—do I really know how to avoid those mistakes?
Here’s what I do know. I want to build a business that does some goddam good in the world. I want that more than anything in the world. I want to prove that people can organize to Get Something Done That Matters. What capital M Matters? Giving people tools to turn their brains on instead of off. That’s something I love. I know I’m not alone in doubting myself. I know it’s a journey. I know I am my harshest critic. That’s a trope, but I can be a real asshole when it comes to treating myself how I’d like to be treated.
So that’s what this whole end-of-2018—Happy 2019, by the way—reflection is about. I’ve been diving into the lake of my self. Knowing my instincts are a good early warning system, I’m asking myself what’s holding me back. What am I ashamed of that I need to get over. Why don’t I believe in myself? How do I lead myself the way I’d like to see a leader lead, instead of harshness.
A friend told me this year, "You have the ability to radiate light on someone when you're with them, but you haven’t figured out how to focus it yet.” What a compliment. But this year, maybe I need to learn how to focus that light on treating myself well. Maybe that’s where I’ll find the strength to be more confident, farseeing, capable, and prudent.