When I graduated college in 1997, I started a full-time job with the same dot-com startup that I had been working for part time during my senior year. In the twenty-five years that have followed, I’ve had a series of jobs in the same field ("full-stack web development," in today’s parlance).
I’ve worked for companies of all sizes, from tiny startups to enterprise businesses with billions of dollars and thousands of employees. I’ve worked in downtown Boston, in Cambridge, and in the western suburbs. I’ve commuted to work by train, by car, and not at all. (I worked remotely at my very first job, and I have done so on and off for many years since.) All these jobs have been in the typical nine-to-five mold, and I’ve usually gone from one to the next without even a single day off in between.
Ever since my first job, I’ve also always done…something else—something besides my “day job,” something that at least had the potential to bring in some extra money. I did a little contract programming at the start, but I didn’t find it appealing to just do more of what I was already doing.
I started writing for Ars Technica in 1999, and I continued doing that for fifteen years. I also wrote for Macworld (for print and the web), for my own website, and for a few other small publications. I enjoyed writing, and I could get paid for it.
Eleven years ago, as my writing tapered off, I started podcasting, which I also enjoyed and found I could get paid for. Two years ago, I wrote two small Mac apps to scratch a few of my own itches.
Meanwhile, outside of my work life, I got married, bought a house, and had two children. Over the years, I’ve had to learn how to balance these competing concerns. As the financial demands of my life have increased, I’ve had to find a way to increase my income. As my family responsibilities have grown, I’ve had to reduce my “extra” work to a manageable level.
As part of this process, I’ve had to find what I think of as my “maximum capacity.” How much can I ask of myself before I fall apart? I learned some important lessons at my very first job, even before I had a house or kids, by slamming hard into the limits of my own body thanks to chronic RSI. Later, my children helped me plumb the depths of sleep deprivation while also entirely recalibrating my value system.
At each decision point, I’ve adjusted my life to fit within my maximum capacity by curtailing “unnecessary” activities. My family and my day job were necessities. Everything else was optional. As I’ve gotten older, my maximum capacity has decreased, of course, and I have exceeded my limits on many occasions. But for the most part, I’ve been able to keep it together.
It hasn’t always felt great to be running “at maximum capacity” (or slightly beyond) for two and a half decades, but it has always felt like the right thing to do during this critical part of my life.
Spring Dawning
Over the past few years, something has started to change. When I’ve been presented with interesting opportunities that I’ve had to turn down (“Sorry, I’m at my maximum capacity right now…”) it has started to feel less like disciplined life-management and more like disappointment. It’s felt similarly lousy when I’ve had to reject my own ideas for new things I’d like to try. And when I’ve ignored those feelings and said yes when I knew I should say no (e.g., when I decided to make two Mac apps in two months), I’ve quickly bumped into my limits yet again—both physical and mental.
A few years ago, I started to question some of my assumptions. My decades of work on my “second career” had slowly built it up to the point where it was plausibly viable on its own. Was my day job really necessary? I started formulating a plan to quit.
Then came COVID-19…and it kept coming. There was just too much uncertainty. My plans were put on hold. It’s been a rough few years for everyone, including my family. The whole experience recalibrated my value system one more time. I started to think more about the limited number of years I have left—with my kids, in good health, on this earth. How do I want to spend that time?
By 2022, I had returned to thinking not only that it’s possible for me to quit my day job, but that it’s necessary for me to do so.
And so, on March 25, 2022, I left my “normal” job. I am now officially self-employed.
On My Own
“Going indie” is what we used to call it in the early 2000s. Back then, in my circles, it usually meant creating and selling your own Mac (and, eventually, iPhone) apps, but each person’s road to independence is different.
I’m lucky to know so many people who have walked this same path before me. They’ve all taught me so much about what it means—and what it takes—to be independent. John Gruber took some huge risks when he went independent back in 2006. At that time, like John, I had recently had my first child, and the idea of quitting my “real job” was unthinkable to me. All my current podcast co-hosts are independent: Merlin Mann since 2002, Marco Arment since 2010, Casey Liss since 2018, and Jason Snell since 2014. And there are many more—too many to list here. When I think about the friends I’ve made as part of my second career, it often seems like they’re all independent. Now, finally, I’m ready.
I am thankful to have had such a conventional, largely successful career at my various day jobs. Like many people who entered the tech world in the late 1990s, I worked for several companies that were later acquired or went out of business. And, like most people, I did not strike it rich at any point via an IPO or similar “exit” event. But the regular salary from my day job did help pay for my house, my car, some nice vacations—a whole life for myself and my family, which is all I ever wanted.
I’m also thankful for everyone who has made my second career possible: all the people who have read my writing or listened to me on a podcast. Special thanks to those of you who have supported me by buying something from a sponsor or paying me directly for my work. I would not be able to do this without you.
Finally, I want to thank my wife, Tina, who has always supported my “weird hobbies,” even back when they took an amount of my time that was far out of proportion with the money they brought in. Each time I have exceeded my maximum capacity over the years, she has been there to pick up the slack, all while pursuing her own career. I would not be where I am today without her love and support.
You can hear me talk more about this topic on episode 179 of Reconcilable Differences (starting at 50:47).
If you want to know how you can best support my work, the answer right now is through podcast memberships. It’s not a coincidence that so many independent podcasts started paid membership programs shortly after COVID hit. Memberships provide reliable income in an uncertain market. Each of my podcasts has a membership program, linked below.
Both monthly and annual memberships are available. The member benefits vary, but all include a version of the show without any ads, plus some amount of bonus content.
Podcasts are now literally how I make my living. (Boy, that’s weird to write. I’m not sure how I’m going to say it to people in person.) I hope you’ll all continue to listen. Wish me luck…
