WHEN HOBBYISTS EMERGE FROM THE DUNGEON TO CREATE AN UNEXPECTED CAREER.
How a younger generation is rolling the dice on their future by turning hobbies into careers
John Dempsey was barely scraping by as a martial arts teacher, fitness class leader, shiatsu therapist, CPR instructor, business planner, resumé designer and furniture mover. But that was then.
Now, he’s a professional dungeon master.
The Toronto resident’s main source of income comes from running sessions of Dungeons and Dragons (D&D) – the fantasy tabletop role-playing game currently enjoying a renaissance due to the popularity of 1980s nostalgia – mostly for “busy professionals” in the upper tax bracket.
His situation isn’t unique. As housing prices spiral out of control and entry-level jobs increasingly demand stringent qualifications, people lacking the comfort of an established career and those just entering the workforce (yes, Millennials) are turning to the gig economy – that buzzword-y, hazy concept that increasingly encompasses work done by people who aren’t technically anyone’s employee.
If you’re under 30, it’s probably been drilled into your head by a parent, teacher or maybe even a boss that your work life won’t be the same as your granddad’s. The days of marching up to the CEO, throwing down a firm handshake and netting a 45-year well-paying job with upward mobility are long gone. You’ll probably spend time in a couple different careers – five years here, 10 there – until you retire a seasoned jack-of-all-trades. Or at least a few.
What your confidants may have failed to mention is the likelihood of a future that doesn’t include going from one job to the next in an orderly fashion, but rather taking on as many scattered tasks as possible just to stay afloat. It’s a practice that’s become so popular it has its own term: the “side hustle.”
How-to guides are everywhere for starting one. You can drive an Uber, work as a Taskrabbit, fill out paid surveys or “flip” thrift store clothes to resell on eBay – these, depending on your perspective, are either empowering ways to make extra cash or a Big Bad Evil onslaught of rights abuses that will kill us all.
For Dempsey and others like him, the precarious freedom from working under a boss’s boot can be exhilarating. As the old, corny adage goes: “The person who does what they love never works a day in their life.” Dempsey was introduced to D&D in grade 10. He was hooked, and quickly learned how to run games of his own as a full-fledged ”dungeon master.” After moving to Toronto, away from his close-knit group of friends he’d shared adventures with for decades, Dempsey took a break from D&D to focus on setting up in a new city. But an expensive rent combined with a run of bad luck – his martial arts students left for the summer and he was laid off from his fitness instructor position at Seneca College – soon spelled money trouble.
In the midst of his financial difficulties, Dempsey was hit with inspiration: what if he could make a few bucks at his old pastime, running D&D games? Just until things went back to normal. “It would really help out, but that’s not likely,” he remembers thinking to himself.
He placed a couple of ads on Craigslist and Kijiji, and didn’t hear anything back for a month and a half. “All my friends were like, ‘Ah, it was a stupid idea,’ and even I was thinking, ‘Yeah, that was a stupid idea,’” he said. “Then all of a sudden, bam! I started getting calls.”
Dempsey starting running games for business types and aspiring nerds who had seen D&D on Stranger Things, but had no idea how to play. One night, he ran a session for a company that produced music videos. The workers had a blast, and eventually suggested to a client, Torontobased jazz-hip-hop darlings BadBadNotGood, that they set an upcoming video in a garage while band members play a game of D&D.
The idea was a hit, with the end result being a video for their song “Lavender,” which features Dempsey in a faux infomercial-style pitch for his dungeon master (DM) services. “I just started getting all kinds of calls after that,” he remembers.
Now, Dempsey has stopped designing resumés and cut way back on time spent on his other jobs. The room where he once shiatsued clients has been overrun with model castles and adventuring gear. The only space he has left to treat clients is his dojo. “I sit with my friends sometimes and laugh and say, ‘I can’t believe I’m actually getting to play Dungeons and Dragons and get paid for it, this is just great,’” he said. “I’m not going to be a millionaire off it, but I don’t have to lug furniture for anybody anymore.”
While Dempsey has been content to stay local and run enough games to pay the bills, others are striking out further. Andrew Armstrong is planning to expand his mini-empire of D&D YouTube videos, guides and personal DM sessions to include a certification program where aspiring pro DMs can run games under the banner of Armstrong’s company, DawnforgedCast.
As a fourth-grade elementary school teacher, Armstrong enjoyed a modest following on his YouTube channel, where he uploaded videos of D&D games, and tips and tricks for other DMs. But as his audience gradually grew, he faced a choice: keep grinding away at a job he liked well enough, or bet on himself and start his own venture.
The change was “really intimidating” at first, Armstrong said. The school year ended and his baby was born right as he made the decision to strike out on his own. He worried about stability, but soon found his feet.
Turns out being a professional DM actually isn’t that much different than teaching – lesson-planning, setting up your week, showing people the ropes and managing them while communicating clearly are all integral to running D&D games. The main difference, Armstrong said, is the potential for growth.“The harder I work, the more I get out of it,” he said. “It’s only going up from here, whereas I’d need 10 years in a (school) district to move up the ladder.”
But although he’s currently pulling in nearly $3,000 a month from Patreon – the crowdfunding service where users pay creators a small amount per month to access their work – the fear of instability is still on Armstrong’s mind. “Being my own boss is great and terrible,” he said, “because I can work at midnight if I’m feeling inspired, but then if I don’t do it, no one does. There are some weeks that are just packed with things to do. The fun gets muddled up with the work a little bit from time to time.”
Blurring the lines between work and fun is a major risk for those looking to start their own business doing what they love. If it fails or starts to become a headache, the stakes are not only your job, but your favourite pastime as well. For Armstrong, the pressure that comes with running a campaign for money can give him “performance anxiety.” He says that in the lead-up to a session “it can feel not exciting, but nervous.”
Armstrong isn’t alone. Full-time freelancers often report feelings of anxiety and loneliness. A 2015 study of stress in self-employed individuals published in the Journal of Occupational Health Psychology said that stress about income was “common,” as was general “apprehension/anxiety, frustration, anger, and sadness/depression.” As Sara Horowitz, founder of the New York-based Freelancers Union, told the Financial Times, “If you’re running health programmes for mine workers you have to be experts in black lung disease; if you’re running them for freelancers you have to specialize in anxiety.”
But while anxiety remains part of the gig economy, the creative freedom it allows can also outweigh any sense of worry. “The thing that pops out to me the most is that, when lightning strikes, I can do something with it,” Armstrong said. “When I have a cool idea, I don’t have to save it or wait for it. I can simply indulge the creative side.”
It’s that constant indulgence into one’s own creativity that underpins nearly every do-it-yourself side hustle success story. And if you’re talking D&D and frantic creativity, you can’t go far without mentioning the McElroy brothers.
Justin, Travis and Griffin host The Adventure Zone – a podcast where they play D&D with their father. In 2011, a year after the debut of their flagship podcast My Brother, My Brother and Me – or MBMBaM – the Maximum Fun network approached the McElroys and brought them on as partners. The trio, building off the opportunity, have since built a sprawling media empire. The Adventure Zone – one of many podcasts, TV and YouTube shows – is the only programming they do that includes their father, longtime West Virginia radio host Clint McElroy.
Justin, the oldest of the three, is candid about how working with family so closely for so long isn’t always easy. “It’s caused some fights before but nothing monumental or earth-shattering,” he said. “It’s always been a worry for me, working with my family. We never wanted it to get to a point where we couldn’t walk away, mainly because if it ever got in the way of our relationship, we didn’t want to do it anymore.”
Since they started podcasting in 2010, the brothers have attracted thousands of listeners and spawned a live show touring the U.S., as well as a TV adaptation following the same format as MBMBaM. The money started slowly, trickling in via paid shoutouts, where fans could pay $100 to have a message read out on the air.
Now attracting heavyweight podcast sponsors like Blue Apron and Casper Mattresses, Justin remembers when their number one client was Extreme Restraints, a sex toy company. “Podcasting was fairly young and our show was certainly not well-established, so we had some – esoteric, I would say, advertisers,” he said. “But they were amazing and all those ads were the best fodder for a comedy podcast.”
Like everyone who has found success doing what they love, the McElroys don’t see themselves going back to a “normal” job anytime soon. Their story offers an appealing premise: finding what you love doing and making it a career. However, for every success story, there are many more failures. Entrepreneurs in general have a dismal success rate, and gig economy workers overwhelmingly receive infinitesimal pay.
As yesteryear’s idea of decades in the same office building gives way to today’s reality of the ceaseless hustle, there remains a perception that those employing themselves in the gig economy are doing so as an alternative to a more traditionally defined career. For a sizeable chunk of workers – one in five, says Pew Research – the money earned through a variety of side hustles is needed just to survive.
The alternative for these workers isn’t a well-paying job with upward mobility and reliable benefits; it’s not eating or not finding shelter. While the temptation might be to laugh at pie-in-the-sky business plans like Dempsey’s, Armstrong’s or the McElroys’, their strategy is borne out of what seems like a no-win situation. If you’re going to be broke anyway, wouldn’t it be better to be so while doing something you love rather than assembling IKEA bed frames for $30?
Why shop for someone else’s groceries when you could play D&D in front of thousands of adoring fans? For those willing to work hard, practice patience and hope for twice as much luck, it might be the way forward.
For everyone else trying to navigate the ever-changing job market, they’ll just have to hope their career has enough hit points to take whatever the future throws at them.
“Why shop for someone else’s groceries when you could play D&D in front of thousands?”