Above-average mediocrity

I started writing this a while ago and am publishing it now even though I don’t feel this anymore. Nonetheless, I edited and finished it because I think the vibe is interesting and might be helpful to another fellow “bottom of the top 1%”-er.

So here we go.


I’m going to chip off a piece of the feeling I described in my previous posts, It’s Been A Long, Long Time and My Unannounced and Inconsequential Break from Social Media, and dissect it a bit more, just for fun.

Delusions of grandeur

Oh, I had big plans, big ambitions. “Three million by 30,” is what I used to tell myself in my mid-to-late 20s when my first startup was starting up in San Francisco. I figured three million dollars at six percent interest (conservative investments) would yield $180,000 per year. I could retire with that annuity if I wanted to (but of course I wouldn’t).

I believed I was destined for greatness, that all I had to do was put one foot in front of the other and I’d walk my way, chest puffed and bent arms swinging, to the top of the heap.

I recalled a mentor at UC Berkeley meeting my girlfriend at the time at a fancy banquet. When I introduced him to her he smiled and pointed at me. “He’s going to be rich,” he said to her. I never forgot that.

When I was leading some environmental programs at UC Berkeley I remember one of the campus facilities leaders introduced me to her peers as the future governor of California. I don’t remember what I was there to talk about, but I remember she said that.

When I was in high school, I sat in the right rear seat of a car while my friend’s mom drove. My friend sat in front of me, on the passenger side. Out of the blue, his mom turned around at a red light and told me she’ll vote for me when I run for governor. Another friend, someone I volunteered with at a community organization in high school, also reminds people we meet that I’ll be governor someday.

Governor. Someday. Sigh.

The older I get, the harder it is to live up to these lofty expectations. It’s as if my first two decades were a dream where everyone I knew seemed to anticipate my gilded future. Now I’m awake, two decades later, and those things I was told were supposed to happen haven’t happened.

I’ve worked hard. I’ve put one foot in front of the other. But the fortune and fame have not materialized. I’m not at the top of the heap.

Instead, I find myself at the bottom of the top 1-ish percent, a no man’s land of far more than most but far, far, far away from the best.

Pride and punishment

I know I shouldn’t care. Sometimes I really truly honestly don’t, and those days are wonderful. Sometimes that feeling of freedom from expectation and comparison lasts for a week. In that time I’m at peace. I don’t want, I don’t need. I’m content with my work, my assets, and my friends and family. My lot is just fine.

And then I get a LinkedIn or Twitter alert. A guy I know from graduate school is listing his company on the NASDAQ. A friend from college has a top position in the Biden administration. Another one sold his company for $30 million, has $500 million in cryptocurrency tokens, or a hundred thousand Twitter followers.

I think about the companies I’ve started and sold for barely a fraction of those amounts. I look at my bank account, Twitter likes, blog visits, and crypto portfolio. I ask myself what I’ve been doing, why I missed those opportunities, started the wrong companies, bought the wrong stocks.

Sometimes it comes on a phone call. Just a regular check in with an old friend.

“Oh, you’re still doing that?”

“You’re going to sell for what?”

“You can’t join the syndicate? It’s just $30,000.”

And suddenly I’m inadequate. It corkscrews my intestines. It impacts my mood. I get off the call and just think. I cross my arms across my chest and stare at the wall, lost in thought, feeling bad about myself for feeling bad about myself.

I tell myself to let the feelings cycle through. I chew them up, like I’m digesting them, and explore the colors and textures, shapes and smells. I’ve mulled over these so much in the last few months, and I’m finally, finally able to get them out. A long-awaited defecation of self-destructive emotional waste.

I’m a proud person. I want for myself what many people along the way have also wanted for me: above average success. I went to Berkeley, Harvard, and MIT. I started companies, sold them, got married, started a family, bought a house. I’m a good leader and a great husband and father. I know these things and I’m proud of them.

I also recognize that it’s the same forces that got me this far that keep me from settling down. I haven’t lost the lust to have a “great” career.

But what’s a “great” career and how is it measured? I’m still figuring that out.

Personal greatness

The opinions that matter most to me are my wife’s and kids’. It’s been that way since I became a husband and a dad and I know that I’m doing A+ work there.

I don’t compare myself to other dads. How can I? I don’t know what happens when their front doors close. I don’t know if they fight or yell or ignore their kids all evening while staring at the TV or their phones. But I really truly doubt it. Either way, it has no bearing on me (but I’m glad, for my neighborhood’s sake, that my fellow fathers all seem to be very good at this parenting thing.)

So I have no father FOMO. When I see a happy family walking through my neighborhood with beautiful, happy children, it warms my insides. I want to meet them, let some of their good vibes rub off on me, and make a new friend. I want them to come over for dinner, to invite the dad to a creek campfire, to celebrate each other’s good fortune to be raising a family right here, right now.

There’s no jealousy at all, so I have what I might call a “dad swagger.” I’m confident, happy, and friendly with every dad I meet.

Professional greatness

It’s not the same for me professionally. I compare myself to everyone and feign a smile through the bitter taste of jealousy when someone has achieved something that I want. This is the punishment for my pride, the thing I’m improving upon but still dealing with. It’s the shit I need to extricate after chewing on it for years but really being aware of it for the last few months.

I can’t cap off my corporate career until I’ve maxed out my earning potential. I have another company or two left to build, run, and sell. I think about it all the time. I mean all the time.

On the one hand, it’s good. I’m ambitious. But on the other, it impacts my appreciation of right now. My professional aspirations are future-facing. My personal ones are right now. I’m happy with right now, but I lust for the future. It beckons me, like a siren song, to be smarter, get luckier, try harder, work longer, and get the big break I’ve been craving since we first started Scripted.

I know I’ll regret not giving myself the opportunity to be a founder or super early employee of a unicorn (that’s a company with a $1 billion valuation, for you non-tech people). Odds are not in my favor that it happens, and I’m okay with that, but I need to try. This is my next Harvard.

So, I’m preparing. Teaching is one way of prepping myself. Taking classes on Solidity and anything else I find interesting is another. I also find that exercise does wonders for my energy and creativity, so I’m working out a lot and treating my body well. This process is taking time, but I’m enjoying it.

When the next big break opportunity comes, I’ll jump on it.

Political opportunities

Someday I will retire as a politician and get back into teaching and writing. I know this for sure. What happens between now and then is still up in the air.

I’m 39 now, going on 40. That’s still pretty young but also pretty damn old. I once believed I needed to be running for something or already in office by my 40th birthday. I’ve given myself another decade.

I met a MIT Media Lab guy who ran for congress in Southern California. He’s very impressive and working on fundraising software and blockchain technology now. He told me that his 30s were about “me” and his 40s will be about “we.” He’s going to do one company only and focus on his family for the next decade.

I feel like my 30s were “we” (especially since my first kid was born when I was 32) and my 40s will be a little bit more “me” but still mostly “we” and my 50s will be downright selfish as I’ll definitely be in politics by then, fully immersed in the whole scene. All of it. The dinners, the ceremonies, the late-night dinners and networking. I’ll be all over it once my kids have moved out of the house when I’m in my early 50s.

I’ll be a good politician. I might even be a great one. Time will tell.

Until then

One day at a time. That’s it.

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