How a younger gen­er­a­tion is rolling the dice on their fu­ture by turn­ing hob­bies into ca­reers

National Post (National Edition) - - FRONT PAGE - Jack Hauen,

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?”


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