My Year in Review 2019
This was the most abrupt year of my life.
Highlights
We bought our first house in Richmond, VA. My wife and I officially ended our nomadic travel nursing spree. For almost two years we moved to a new city every three months — Phoenix, Salt Lake City, San Francisco, Salisbury, and finally Richmond. For good.
We had our first baby. Our beautiful bundle of dancemoves daughter Brooklyn joined us on February 11, 2019.
I published stories in CNBC Make It, Trends, and Forge Magazine and interviewed the CEOs of Dippin’ Dots, Stone Brewery, Gumroad, Unsplash, and RealtyMogul.
I made over $6,000 in one month from my side gig writing on Medium.
I gave up my freelancing career and cofounded a VC-backed tech company called Hopin with a partner I’d never met in person.
I went to London. First time in Europe.
My Medium course cleared $15,000 in passive income this year.
My app Party Qs was redesigned and tripled in monthly revenue.
My Medium publication Entrepreneur’s Handbook grew to 115k followers (from 80k). It’s the 32nd largest publication on Medium.
One change took place internally.
I can now say I’m ready for my thirties (happening in 2020). I know, you read that and probably a little scoff tickled the back of your throat. “You’re so young, Dave.” “You’re not even that old, Dave.”
While it’s true I’m not that old, and “young” and “old” are relative, I have been afraid of my thirties for years. I’ve written about my fears of settling down and of becoming a dad, hesitantly calling them metaphors like a “ball and chain” or a “prison sentence” mainly because buying a house and having a child permanently reduce one’s freedom—there’s no other way around it. The freedom of my twenties was thrilling; I will always look back on these years as a time of experimentation, wondering and wandering, adventuring, new experiences, new people, new skills, and new ways of seeing a bigger world than I’d previously known.
In 2019, the reality of settling down settled in. I saw our traveling go down (although we flew B to Boise when she was two months old), I saw the number on the weight scale creep up, I saw days repeat into routines, and I saw the number of our monthly subscriptions spin sideways.
For the bulk of 2019, my career looked as multifarious as my twenties. It was all over the place. I wanted it that way. My income came from a dozen different revenue streams — clients, projects, apps, books, courses, consulting, investing. I was a professional plate spinner.
But as this year comes to a close and our eyes lift to the 2020 horizon, I can’t help but notice a transformation.
I’m not sure how to describe it. I’m digging in my heels. Gearing up. Biting into a huge hunk of meat that’s going to take a long time to slowly chew, enjoy, and digest.
My metaphors are failing me. Here’s a real-life analogy. I bought a desktop computer. Buying a desktop computer is like dropping an anchor. You’re not supposed to move once it’s deployed.
With Hopin, I’m committed. There’s a lot of work ahead, but 2020 and some of the announcements we’re about to make will cause Hopin — and my responsibilities therein— to take off like a Falcon Heavy.
My career is locked in for years and years. For the first time in my life, I’m glad for that. I don’t feel stuck. I feel well-placed.
Outside of career, I’m committed to my family, which will probably grow here soon. We’re planning on having another child at some point in 2020. Every day with Brooklyn is a personal challenge to me to figure out a new way to make her laugh. Because there is no greater sound in the world than my daughter’s breathy giggle. Also, I’m taking Steph to Hawaii in January. Just us. No baby.
Richmond is an old gem. A dull diamond. When I talk with people around the world and I mention I live in Richmond, I’ve found their reaction is null. Richmond is like the necklace that nobody notices. I feel tepidly towards it and its utter sufficiency as a living place. I’m grateful for my church community — without it, I’d have no local IRL friends.
I Never Thought I’d Say This…
Another inward way I’ve noticed this transformation is a shift in my thinking on the annual debate that always gets stoked up around this time of year: goals vs. systems.
Systems were for chumps and goals, i.e., New Years Resolutions, have always been a hill that I would die a thousand deaths on. Goals keep your life fresh, challenged, stretched. Systems are put in place to keep everything the same, like a boring machine. Systems lead to complacency and, without the disruption of goals, prognosticate mundanity.
I typically set several dozen New Year’s Resolutions each year. Three years ago, I had 33. I usually get more than half of them done every year. That’s okay because a lot of them are wild, stretching, or random. This mindset was appropriate for my twenties. I would do it the same way if I had to go back, until I knew what I wanted to do for a long time. Basically, the point is goals are great for getting you to experience the breadth of life and become a more well-rounded person — until you find the right semi-decadal vision for your life. Once you find the multi-year task(s) that you want to get better and better at, wide and varied goals feel too much like a waste of time. Now that my goals are fewer and more focused, they’ll be the same for the next few years, just greater in qualification and quantification. I’m going deeper, not broader, in my thirties.
It’s fun having a laptop, but the older you get — meaning the more specific, fewer, and longer-timelined your goals become — the more you’ll want a desktop.
Now that I can envision what success looks like (to a limited and unguaranteed extent) for multiple years of my life in the future, I want to prop up systems to support and achieve it. So, in 2020, I’m less ra-ra about publishing my long list of goals and more focused on digging deeper to better prepare for the work God has given me to grow my company and love my family.
What were your 2019 highlights? How have you changed?
