A few weeks ago, Jesse, the band director at one of our local high schools, asked if I might like to come in and speak to his class about creativity and persistence. I dug up my old junior high marching band photo, drew a bunch of charts, trying to get at something that would be relevant to their lives even if they quit band (like I did, at the end of eighth grade—see below). This is a slightly more detailed version of the talk I gave to the class:
I’m a full-time creative, which means … well, it’s kind of different every year. My job has been 100 percent freelance since 2012, which essentially means I have a bunch of different part-time jobs, or “side gigs.” One of which is public speaking, but not really TED Talk-style speeches. I like to create slide shows with lots of illustrations, and then talk about those. Here’s a pie chart of some of the things I’ve done for money since I became a full-time freelancer/independent creative in 2012:
Sometimes that looks like some of the photos here, where I’m out in nature somewhere, far from an internet connection:
But honestly, 99.5 percent of the time, I’m sitting at a desk or a table trying to create something from one of the experiences I’ve had out there, or some idea that came to me when I was outside. I’ve been doing this a while, but before I got to do it full-time, I had many years of working other jobs, starting with my first real W-2 part-time job as a dishwasher and busser at a restaurant when I was 15, in the Pinicon Restaurant in my hometown, New Hampton, Iowa. We clocked in at 4:00 or 5:00 p.m. and washed dishes until bus tubs of dishes stopped appearing on the wire rack next to the dish pit, which sometimes took until 12:30 p.m. if there was a wedding reception in the dining room.
After high school, I became a bartender and server at an Applebee’s restaurant, and then a sports bar and grill after that. I loved waiting tables and bartending because it gave me a rotating audience to talk to every night. Some of my managers might say I should have spent more time trying to upsell appetizers and drinks instead of trying to make people laugh, but I thought I was a pretty good waiter.
After college, I worked for about three years at a couple of very small newspapers that no one read. I didn’t love it, but I also assumed no one landed their dream job right out of college. Plus, I had plans to become a successful adventure writer, so after work, I pitched articles ideas to climbing and adventure magazines. My first year of freelance writing, I made $40. The next year, I made $150, and the year after that, I made $1,800, so it was a good thing I had a “real job” besides freelance adventure writing.
I quit my last newspaper job in 2008, choosing to take a pay cut (!) and work a nonprofit job I was probably overqualified for. But at least I could talk to my co-workers about rock climbing, and even go climbing and skiing with them after work. And I kept pitching my adventure stories to magazines, and I started to get more bites, and more income.
I quit my nonprofit job for a sweet remote copywriting gig my friend hooked me up with, and then I could work remotely, writing marketing copy about software products, and then in my spare time growing my freelance writing. Around this time I started my own website, Semi-Rad.com, where I decided to publish one piece of writing per week. Those blogs were mostly ideas I thought were too ridiculous or unserious for “real” outdoor publications, which was probably why people liked them. I mean, some people did. I started to get some traction pretty quickly and slowly grew an audience and found more opportunities coming my way.
By mid-2012, I finally had enough freelance work to make a go of it full-time. I was completely terrified, but put in my two weeks’ notice at my copywriting job, shipped my work computer back to the company. I walked out of the pack and ship place anxiously hoping I could make enough money to keep things going for the next few months, and find more ways to make money so I could continue being a “full-time freelancer.”
I did OK that first six months, but it’s worth noting that I was living in 2005 Chevy Astrovan at the time, sleeping on friends’ couches a lot, and had a $100/month health insurance policy that would probably have covered almost nothing if I had needed medical attention for anything.
Still, I was making a living. It didn’t feel solid, and in our weekly phone calls, my dad would always ask if I had enough work coming in. He would do this for the next five years, when I think he felt like I was doing OK (I was).
But every year, my pie chart of income sources changes, and so does another pie chart I think about a lot: Imagine with me, if you will, that you get to decide how to spend your 40ish-hour work week, and you classify the things you do as serving either “Capitalism” or “Creativity.” Capitalism, in this case, just being a word that means “making money,” which used to just mean “making money so I can afford to eat,” but nowadays means “making money so I can afford to eat, and also afford to have a place to live with my wife and toddler, and also afford to pay for medical expenses, and other stuff.” In theory, you have a blank pie chart, which you can fill in:
If you’re a creative person, of course you’d love to spend all your time concentrating on your art, whatever that is—playing the trumpet, writing fan fiction, painting landscapes, photographing architecture. That would look like this:
Unfortunately, that’s not a reality for most of us, and by “most of us,” I mean people who are not independently wealthy or who might have a very understanding spouse/partner who has promised to pay for everything so their partner can spend their time on art.
Most of us have to work in some capacity, which of course is a huge bummer but necessary if we also want to do things like eating sandwiches, which cost money, even if you make them at home. But you are/were creative, so you don’t want to spend all your time on “work,” which would look like this:
Of course I’d love my “job” to provide total creative freedom, but as previously discussed, everybody* has to pay bills, so even the most free creative situation might look like this, a 75/25 split:
But honestly, that’s not how it looks for most of us. People have full-time jobs in which they use their creativity, or like me, are, “independent,” which just means you’re constantly trying to find ways to get paid for creative work. Either way, you spend a lot of time doing things that aren’t purely “creating,” like meetings, emails, charging batteries, cleaning paintbrushes, and messaging the accounting department to find out why you haven’t been paid yet. In my case, some weeks it feels like I work a lot more on the non-creative stuff, as I imagine most people in creative careers feel. In any case, I consider myself lucky that I get to spend even 25 percent of my time being creative, so my pie chart looks like this, and I’m totally fine with it:
Here’s a picture of me in eighth grade. It doesn’t look like much, but this is the pinnacle of my musical career, when I got to play the snare drum in the Red Oak Junior High School marching band. (I had taken two years of piano lessons in elementary school, so I knew how to read music, which is how they picked who got to play drums in band in sixth grade.)
Here’s a photo of the whole band (I’m in the back row, to the right of my friend Justin Sharpe, who is really tall in this photo and would grow to be 6’11” and become a high school basketball star):
I don’t have a lot of regrets in life, as I think holding onto regret is usually not that helpful. But I do have a few. A pie chart showing those regrets and how much they contribute to my sum total regret in life might look like this, with most of the regrets being tattoos I’ve gotten:
That’s not to say tattoos are bad, or you shouldn’t get tattoos—I’m just saying I got some dumb ones, and if you could get them removed as easily and inexpensively as you can get them put on, I would have done that already. Alas.
What’s that big red chunk of the pie chart, though? That seems to be the biggest regret.
I didn’t regret it at first—at the time, I was 14, we moved to a new town, and they didn’t have room for another snare drummer in the marching band. Plus I wanted to play football, which I believed to be “cool” at the time. As I remember it, I had to choose between the two: Band or football. So I picked football. Which, as they say, “seemed like a good idea at the time.”
Fast-forward a dozen years, and I started traveling, and seeing how much fun musicians were having. I was in the Latin Quarter in Galway, Ireland, one dark, rainy winter, and couldn’t believe how many people I saw out playing or singing music in the streets, busking: A guy with his hat sitting at his feet singing a cappella (maybe just till he got enough money to buy another pint?). A guy with an electric guitar and amp, playing AC/DC’s “TNT,” chanting “OI!” over and over, at 10:00 a.m. This full band of young guys, who set up in a busy shopping section and immediately drew a crowd with their cover of “Wagon Wheel”:
I remember thinking, “What was I doing when I was their age?” Answer: Not playing music with my friends, because I quit band in eighth grade.
This happened many times: In New York subway stations, in Hong Kong, in L.A., in London, and one night walking around Washington DC, running into these guys posted up outside a Krispy Kreme, whose band had four trombones a five-gallon bucket for tips.
Musicians, I realized, have a language they can speak with each other, no matter where they go. If you don’t speak the language somewhere, but you play an instrument, you can jam with anyone.
A couple years ago, we inherited a piano from a friend. It’s not a nice piano, or tuned, but had I kept up my piano lessons and kept playing, I’d have three-plus decades of piano experience now. Starting from zero in middle age is much tougher.
My friend Ian visited last year, and when our toddler sat on the piano bench, Ian leaned his left hand around Jay and played the opening notes of Ray Charles’ “What’d I Say,” as casually as someone might stir cream into coffee.
Nowadays, I think of football as something to watch, not play. Music, you can play until you’re 91 years old (at least if you’re Willie Nelson).
I’m not saying you should keep playing the trumpet or the clarinet for the rest of your life, just because you play the trumpet or the clarinet in high school. But you do have a language you can speak—music—and just like learning Spanish or French, if you stop regularly speaking it, you’ll probably lose it.
The more important thing I’d recommend is not losing the practice of creating, however you do it—your particular style of playing a song, painting, photography, making videos, writing fiction. If you’re wondering, “Am I creative?” I’d say: If you’ve ever made something that didn’t exist before, you’re creative.
It’s easy to be creative in the first part of your life—no preschooler ever thinks, “My finger paintings aren’t very good.” But as life gets more serious, and you have to make time to study and do homework and think about a career, and then start working in that career, it can be much harder to do those creative things you love to do:
You may not think much about what you’re learning in band, aside from playing your particular instrument and whatever songs you’re practicing and performing. But there is one really important thing.
I was out running with a friend who’s a high school teacher, and when he’s not teaching, he plays music. He told me that in class, he can tell which students play an instrument or sing, because they’re less afraid to contribute to class discussions, or raise their hand and offer answers to questions in front of the rest of the class. They’re less afraid to fail.
Because if you’ve ever played a wrong note, or come in a beat too early, you’ve failed, right? Sometimes it’s a small failure—you’re practicing at home and you get a note wrong. Or it’s a more noticeable failure, maybe in a concert or performance. Either way, you’ve all failed, probably hundreds of times at this point. No big deal, you’re used to it:
And you know that it takes a lot of those failures to be able to play your part in a song well, which might look like this:
Take all those failures and multiply them by every person in your school’s band, and you have thousands upon thousands of failures, and that’s what it takes to make that first good performance of a song.
For whatever it’s worth, this is also the writing process, and, I think, how you learn to make films, and probably everything else. As the saying goes, good judgment comes from experience, and experience comes from bad judgment.
You may not play an instrument when you’re 35. You may not even like band that much, for all I know—maybe you prefer writing poetry, or cooking, or making Spotify playlists for your friends, or taking photos of trees, or drawing manga characters. I would encourage you to do whatever it is that lights you up, or gets you in a flow state.
At some point in the next few years, you’re going to be busy with a career, and all the other things that come with being on your own: doing laundry, buying groceries, paying bills, maybe raising a family. You will, believe it or not, still have some spare time. You can choose, as many of us do, to spend all those spare minutes or hours looking for entertainment—scrolling on your phone, watching movies or shows or short videos someone else made, reading essays or 280-character hot takes.
Or, you can choose to spend that time creating something.
I’m not trying to be a middle-aged guy telling you how to live your life, but I will tell you this: I have had a lot of adventures in my life so far, and some of them don’t require me to even leave my desk. I start with a blank piece of paper or a blank screen, start drawing or writing or moving video clips around, and it always goes somewhere. Sometimes I end up making something that isn’t that great (it’s a first draft!), and I’m kind of disappointed by it. But it always feels like a better use of my time than endless scrolling, or spending a half-hour watching something that didn’t live up to my expectations, and leaves me feeling empty.
I’m not saying you should never be on your phone, never relax, and never watch shows, or movies, or whatever you find entertaining—I’m just saying that as long as you remember that you can create something, whatever it is, you always, always, always have another option. And that it will probably never be a waste of your time.
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