I took about four months off of regularly reading and somewhat regularly posting to social media. I took Facebook off my phone entirely and removed all Facebook email notifications a while ago. LinkedIn followed. Then Twitter. With each step away from the incessant drone of snippets and soundbites my overall well-being improved. It felt like exercising: hard at first, then easier, and totally worth it.
I stopped consuming, but I also stopped creating, and not creating bothered me. Then my grandfather passed away and I needed to write something about that. I shared it on Twitter. Then I sold MightySignal and that seemed Twitter-worthy, so I shared that too. Now I’m easing back into social media, a bite at a time, still unsure if it’s adding to my life or taking away.
I recognize that this problem is of my own making. These are my own insecurities, my own weaknesses, my own inability to focus or perhaps more critically and to the point, my allergic reaction to the uber-success of my peers. I don’t blame Twitter or Facebook or any of my beautiful and wealthy friends who post their many fabulous accomplishments for the world to see and applaud.
To be completely open and honest about my social media FOMO issues, I had to take a hard look at myself.
The 98th percentile
A few months ago, back in October and November of 2020, I was feeling bad. I had nothing to complain about, really, and that was the problem. My non-issues filled the space. I had the luxury of moping about silly things like the fact that I’m not in the top 1% of 1% of earners. Every time another friend got rich, I’d feel a little bit worse. It kept happening, too. Random friends from high school, close friends from San Francisco, distant friends from business school. A new IPO, a nine-figure acquisition, a viral cryptocurrency — I watched it all happen on my social media feeds.
And from the comfort of my phone I didn’t feel happy for my friends. I felt bad. I felt inadequate, sorry for myself, bummed that my many business at-bats didn’t make me fabulously rich. The family members who invested in my creations lost all their money. The friends and family who invested in my friends must be so proud. It hurt to think this way but I kept doing it, spinning in mental circles, making myself feel worse.
I spoke to one friend in late 2020 who sold his company for $3 million a year or so earlier. He made some money off of that sale, but most of the acquisition was stock. He figured already that his $3 million was worth closer to $30 million. The company that bought him was blowing up, a unicorn ready to IPO. He started his own fund, expecting that I might invest.
My answer was easy: I couldn’t. The double-whammy of feeling jealous of his success and ashamed that not only was I not in his same income bracket and definitely not starting a fund, I also didn’t have $50,000 laying around to invest in high-risk sales tech startups. It was just more than I could handle. I ended that call feeling like shit.
A couple of weeks later, a friend who got rich in crypto texted for advice about where to park his cash. He asked if I knew anyone running a fund. I made the referral to my $30 million friend. My crypto friend thanked me and invested $50,000. I felt shitty all over again. I’d find out a few months later that my crypto friend’s tokens were worth well over $100 million.
I get The Information newsletter. It’s great and the stories are unique. Someday I’ll pay for it, but for now I just read the headlines when they enter my inbox. In the space of one week there was a headline about a friend’s successful IPO who I went to the Harvard Kennedy School with, and another about the crazy stock growth of another friend from MIT Sloan who went public back in 2017. I felt small.
This is what it’s like in the bottom of the 98th percentile. It’s the no-man’s land of having more than plenty, far more than my share of resources and savings, but simultaneously far less than everyone above me. It’d be one thing if those above me were famous names on a Forbes list. It’s different when they’re my friends, people I know well, guys who started out ten years ago with the same bank balance that I did. Guys who once looked up to me for having it all figured out.
The even stupider part of this pity party is I know now and knew then how ridiculous it sounds. However, self-awareness did not solve anything. I can’t say why I couldn’t talk myself out of this rut. I had moments of clarity, sure, but the fog of jealousy would roll over me again. So I learned to sit with it, shuddering at times, just waiting for it to pass.
Uncertainty of transition
In the meantime, life happened. Transition was all around me. The world was coming out of COVID. My girls were finally able to return to kindergarten and preschool. My family moved into a rental house so we could begin a major remodel. I started teaching part-time at DVC and was in the throes of negotiating an exit for MightySignal.
This was all great and the time passed quickly. I started to think about what I would do after MightySignal and asked some friends for advice. A couple of them gave me job offers. One was a Head of Growth role at a rapidly growing crypto company. Another was a CEO job at a residential proxy startup. I turned them both down.
One thing I learned from my wealthy friends is that the real money, the major, big money usually comes late. You have to see something all the way through in order to get crazy rich. Thinking this way got me excited about continuing my work on MightySignal. Plus, I didn’t want to abandon my team. After a couple of months of uncertainty, I whole-heartedly agreed to stay on the same path. And with that decision came a huge sense of relief.
It turned out that a lot of what I was feeling, which I attributed to jealousy and self-pity, was really just uncertainty of transition. I was going through something, for sure, but the core of the problem wasn’t the success of my friends. It was not knowing what’s around the corner for myself. Knowing that I would stay with Airnow, the new owners of MightySignal, for at least a year and likely longer, was a load off of my shoulders. I felt a lot better as soon as I committed to the decision.
Some other certainties unfolded as well. The remodel project started and I found a great rental for my family just down the street from our old house. This was a big relief, and as the remodel progressed and moved at the pace we’d hoped, that remodel uncertainty and risk decreased a lot. My class at DVC was awesome. I was prepared, the online format worked, and my first two months as an associate professor went really smoothly. In Spring 2021 I also joined two community boards: Sustainable Contra Costa and the DVC Foundation. I felt good about having a strong leadership foothold in my community and no longer needed to seek out new things to do. I have them. I’m where I need to be. I just need to execute.
Focusing on myself, being happy with my work, and being excited to upgrade my family’s house made a big difference in the way that I felt. My friend’s crypto assets swelled up to $200 million in the early 2021 crypto bull run. I felt nothing, which felt great. I stumbled upon more news stories about my grad school friends’ IPOs. I actually felt happy for them. Things were looking up.
The freedom from caring
By feeling good about what I was doing I cared a lot less about what other people were doing. It sounds obvious in retrospect, but I needed to work my way there.
I’d like to think that I can be like Thoreau, content to simply watch the passing of the seasons, but I’m probably not built for that. In my respite from social media I was able to tune out what my friends were doing and instead focus on my family, my neighbors, and the volunteers and students that I work with. It’s more than enough; in fact, it’s all I need. I just need to remind myself of this and be insulated by it as I dip my toes back into the feeds.
The freedom from caring what others think and do is the ultimate freedom. I’m not there yet, but I understand that this is the promised land. The people who find that freedom have the most fun. They also might be the most successful at their trade. But more importantly, they’re able to focus on what makes them happy, whether it’s family, work, arts, or just being alone. I envy those who found this, but unlike becoming a multi-gazillionaire, contentment is completely attainable by anyone. There’s no luck or timing needed. It’s just a mindset.
For six months, that’s where I was: sorry for myself about not being richer than my crazy rich friends while simultaneously spending gobs of money on a new house, paying a mortgage and Bay Area rent, still saving money and not caring what the Whole Foods receipt added up to. That one definition of success — to live without financial stress — and I’ve done that in the country’s most expensive region.
That should be enough, and it is. I’m happy again. I text with my rich crypto friend about normal stuff. We’ll hang out again soon. I like the LinkedIn posts about my friends’ successful fundraises. I read my friends’ newsletters with sincere interest. It’s like I passed a kidney stone of insecurity and it just took a painful while. I’m better now, more resilient to the symptoms described above, and able to think again for myself.
A couple of nights ago I was at my neighbor’s house with four other dads. We’re all in our mid-late 30s with young kids. We met after 8pm so we could help put the children to bed. As I sat there, cocktail in hand, Settlers of Catan laid out on the table in front of me, I thought, This is my Walden Pond. These are my trees, ants, and leaves. I’ll watch these guys grow old as I age along with them. I’ll know their kids almost as well as I know my own. This, right here, is what life is about for me right now. It’s enjoying this stage of life, being a parent, growing a career, building a family and a home.
These are years I’ll never get back. I’m spending them the way I want to spend them.