Lessons Learned From A Decade+ of Words for a Living

There's a lot more to being a writer than writing.

The digital media industry is fueled by contract workers and false promises.

Hey reader,

I stumbled into my first paid writing gig in October 2010. $50 a pop for a weekly column about music. From there, I’ve — slowly and in incremental steps — grown writing and media work into a sustainable career that allows a great deal of freedom. In terms of location and schedule, most notably. But working as a writer also puts me in charge of my income and workload.

This essay is a loose chronicle of my career to this point. I hope you see parallels to your own work, and maybe even take a bit of inspiration.

Did someone forward this newsletter to you? I’d love to have you onboard.

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Community Shoutouts

• Welcome to the 3 new subscribers since the last dispatch!

• Thanks to Jim for a thoughtful response to last week’s post on how to move on (here it is, in case you missed it).

Now, let’s get reflective.

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Lessons Learned From A Decade+ of Words for a Living

In September 2010, parked at a 7-Eleven gas station on South Broadway in Denver, my life hit a low point.

Gripping the steering wheel of my rickety old Saturn tight enough to pop a bottle, my left leg pounding into the floorboard on machine gun repeat, I descended into a full-blown anxiety attack. I don’t remember exactly, but I’m pretty sure I let out a shrieking howl of dismay inside my car.

I’d just spent the last $4.86 of available credit on my high-interest credit card to buy enough gas to drive home from work. The prior week I’d started a new job as a line cook at a bar near the University of Denver, but I hadn’t been there long enough yet to receive a full paycheck.

I was stressed about money, for sure. But that wasn’t the least of it. What had sent me spiraling into a panic at the pump that night was a complete collapse of everything I’d known for the prior eight years.

My punk rock band — which I’d based my life around and had moved to the city with a year prior — was in shambles. The two guys I started the group with had informed me they were moving back to Durango, where we’d begun and where they were from. It was just too hard to “make it” in the city, they said.

I’d just lost another line cooking job because my band’s schedule made it incredibly tough to manage a five-day-a-week workload. That summer I’d found myself repeatedly needing shifts covered so the band could take out-of-town gigs, and when I did make it in, I’d often arrive to cook breakfast at 6 AM deprived of both sleep and motivation. Once I’d even pulled an all-nighter driving our van back to Denver after a show four hours away, and gone straight to work.

Instead of being good at at least one of these facets of my life, I’d managed to tank both.

That night at 7-Eleven, I didn’t have an answer to my problems. But I knew that something had to change. I knew it was time to move on.

Lesson 1: You have to make things happen for yourself

I’d long wanted to be a writer. Since childhood, writing was the one thing I knew I was good at and that I could fall back on. I’d started a “sports magazine” in grade school and sold subscriptions to relatives and neighbors, spent high school on the school newspaper staff, and studied Communications at college (“studied” being a loosely-defined term).

Delusions of grandeur related to baseball (at a young age) and music (at a slightly older age) had never clouded what I always knew I’d end up doing.

But to that point, I had never actually done anything with this skill, and certainly hadn’t developed it to a professional level.

That night at 7-Eleven, which I’ve since dubbed my “quarter-life crisis,” I promised myself that I would change that.

The next morning, I hopped onto the “Writing Gigs” section of Craigslist. Among the dross of nonsense posted there, one listing caught my eye — “Music writer needed for new website.”

Promising $50 per article, the listing sought someone with knowledge of the local music scene and the ability to turn around a story each week.

I responded with a resume that conveyed zero writing experience, but plenty of knowledge of the music business and of Denver’s rock clubs and bars. I was certain that the listing would generate so many applicants that mine would be either lost in the pile or thoroughly laughed at.

Maybe it was the degree I listed at the top, or the fact that I had actual touring experience and “knew people in the industry.” Or maybe no one else applied. Whatever the reason, I received a response within a day.

Hey Tim,

Thanks for applying for the music writing position at Cities2Night. Seems you might be a good fit. We have a test assignment for you to complete.

Attend a concert this weekend. Then, write us a 500-word review of the show and submit on Monday morning.

OK, I thought. I might be getting somewhere here. I opened the local alt-weekly paper, Westword, flipped to the section containing show listings at local venues, and selected a random concert to attend.

I got the gig.

Lesson 2: You never know who is going to read your stuff

$50 per week, plus an occasional extra $50 when a story came up outside of the music realm that the site wanted to cover.

Not enough to live on, by any means, but a start. A solid start.

A couple of months later, I was on the kitchen line at the restaurant working a dinner shift when my phone rang.

A man sounding in his forties or fifties introduced himself. He and his business partner, he said, were launching an entertainment website (apparently this was THE thing to do in 2010). They’d come across an article of mine and wondered if I might be interested in writing for them, too.

Indeed I was.

This new website never amounted to much, but through it, I met someone that would change forever my career.

Lesson #3: The only way to advance yourself is to tell people what you want

• Cities2Night stopped paying me after a year. It was a good learning experience, not least because I experienced firsthand that the backend of a business is generally much messier than what the public — and even staff — see.

• Still, to that point, I had never actually “pitched” a story. I hadn’t learned how to properly freelance, because each gig I’d acquired to that point assigned stories directly to me. They told me what they wanted, and I did it, much like a normal job. I foolishly believed this to be how it was. I had a lot to learn.

• Over that first year, I’d taken another gig writing for a snowboard magazine. For free. It’ll pay off, I told myself. That didn’t happen until I stuck up for myself and told them I needed money.

The digital media industry is fueled by contract workers and false promises.

Publications fold. Paychecks often arrive much later than promised. There is no such thing as a “secure job,” even at established publications.

The industry at large is, effectively, a startup culture that never grows out of startup mode.

Because of this, every step forward happens because an individual decides to take that step forward. Those who sit around waiting for a “promotion” or a “raise” will find themselves waiting for eternity.

That happened to me at Cities2Night. Each week I turned around my assignment and faxed an invoice for $50 (yes, faxed — I drove to my parents’ house once per week to use their fax machine).

The guy that called me on the phone that night needed someone to be out on the scene, interviewing bands and reviewing shows. I never saw a single dollar from that gig. But I learned the most valuable lesson I’d learned to that point about self-employment: I am in control. But to benefit from that control, I have to exercise it.

At the bar at Summit Music Hall on a Saturday night, I learned this firsthand. The website had me covering a “cream of the crop” group of local bands — groups that had generated a lot of buzz, made it to the top of the local scene and, if they played their cards right, may get the chance to strike out at the national level.

Sitting to my right at the bar was a photographer named Matt. I knew Matt a bit from being at shows. He was a talented local photog that bands often hired to shoot their live performances.

“So you’re into writing,” he inquired. “You see that guy over there at that table?”

He pointed to a merchandise table in the corner of the bar area, next to where the bands were hawking t-shirts and stickers. A heavyset man in his forties stood behind the table chatting to a group of musicians.

“That’s the publisher of Colorado Music Buzz,” Matt informed me. CMB was a monthly print magazine that covered music in Colorado, and it was a publication I’d read regularly since moving to Denver. Seeing my own band’s shows listed in the mag had always been a good ego boost.

“No shit, really?” I said.

With beer as my wingman, I approached to introduce — and hawk — myself. Keith handed me his business card and told me to email him on Monday.

Skip ahead six months and several articles contributed to CMB when an email hit my inbox on a chilly September morning.

It was from Keith, announcing to all freelancers that CMB would be bringing on two editors to work under himself and the other publisher/sales director, Chris.

My resume was slightly more stacked this time. Plus, Keith already knew my work and work ethic.

Still, I knew this was going to be competitive. CMB had no less than 20 regular contributors and I was certain this email was going out to writers at Westword and probably many others.

I sent in my resume, and then employed what had by now become a familiar tactic: I showed up. In the latest issue was an ad for an event the magazine was throwing that weekend. It was far enough away — in Parker, a town nearly removed from the Denver metro area — that I hoped not many others on this email would be there.

At the event I cornered Keith at the bar.

“There is no one better than me for this gig,” I said. “I know everyone in the music scene, I play in a band myself, and you already know my work.”

Keith was non-commital.

Still, he seemed surprised that I’d shown up and pitched him directly, for a second time.

Lesson #4: Repetition and consistency are the key to success

• There are a lot of players in the freelance world. Most are full of shit. Following through on what you say you’re going to do puts you at an immediate advantage.

• Writing the same story over and over is part of the game.

• Following up on invoices is essential. Rarely do pubs pay after one email.

Writing and journalism, like any career, has a steep learning curve that never ends. With every new contact comes a chance to better yourself and provide value. With every new chance to provide value comes a chance to hone your skillset.

I got the editing gig with Colorado Music Buzz, a contract I’d hold for four years. I learned a ton during this time and made a lot of early-career mistakes:

• I agreed to take on too much and burned myself out.

• I rarely said no. To writers pitching the magazine stories, to responsibilities, to freelance gigs that had no long-term value for me.

But I also learned a ton about self-advocating and how to think big-picture.

• When pay is late, follow up, and then follow up again. You are not the one in the wrong.

• Being a writer means running your own small business. Among other facets, you have to incorporate, save for quarterly taxes, and develop your own branding.

• Learning from those who are more established and better at their craft is essential to growth.

• Well-known musicians and writers each struggle with their own issues. Most are actually very approachable and willing to share their story, especially if they’re getting press as a result. As a writer, you can learn a lot from these people that can be directly applied to your career.

• Those who are successful in your field started where you are, and worked really hard to establish themselves. By focusing on the “work hard” aspect and applying it to where you want to be, you, too, can become successful.

Shortly after leaving CMB in 2015 to freelance full-time, I published my first article in Matador Network. I have been a staff editor with Matador since 2017, after employing the same techniques I used to get on staff at CMB.

I created value consistently and improved over time, I networked and worked with a variety of people on staff, and in 2016, when I saw on social media that the CEO was in Denver on a work trip, I cold-messaged him and asked him to meet for a beer (we ended up having several).

Lesson #5: The more you put yourself out there, the more you’re going to be in the right place at the right time.

At a conference in San Francisco 2018, I met an editor with Fodor’s at a media happy hour. The first thing she said to me was, “I am really looking for a writer from Colorado for our upcoming Colorado guidebook.”

You can guess how that one ended up.

I’m nearly 12 years into my career. It’s not any easier now than it was in 2010, rather, it’s become progressively harder each time the stakes have been raised.

Progress is the end result. If you aren’t consistently stepping out of your comfort zone, you aren’t trying hard enough.

I began each new step as a newbie whose work was not up to snuff with the established players in the arena. But I always get better, I always learn, I always ask questions and take critical feedback, and I continue to study what others are doing.

A willingness to do those four things, combined with the lessons described here, makes one an unstoppable force of progress.

That’s because this creates consistency. By repeating something enough times you’re bound to get better at it. And if you can create consistent value, even if that value isn’t always perfect, you’re doing better than any who never put themselves out there.

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Mountain Remote news and further reading

• 71-year-old Craig Bierly has lived in a van for 13 years, mountain biking his across America. I watched an incredible documentary short about him last night at the Grand Valley Bike Film Fest. Here it is, produced by Freehub.

• In line with today’s topic, NerdWallet ranked the best US cities for freelancers and digital nomads.

• I don’t always listen to the Tim Ferriss Podcast, but when I do, it’s because Cal Newport is the guest. This week’s episode featured Cal interviewing Tim about his book “The Four-Hour Workweek.”

Thanks for reading! See you next week.

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I drink a lot of coffee putting Mountain Remote together.