The highest highs can feel like the day your first child was born. The lowest lows are like the day that kid drives the family car into a lake while playing Pokémon Go.
But generally, you exist somewhere in the middle — uneventfully, monotonously and, for those of us who work from home, solitarily.
But hey, that’s freelancing, man.
Or should I say the so-called “gig economy,” which judging by Google search results, spontaneously became a thing about nine months ago. More and more people are opting for such work, best exemplified by Airbnb, Lyft and TaskRabbit. In fact, according to LinkedIn, freelancers will make up an estimated 43 percent of the U.S. workforce by 2020. I hope they know what they’re getting into.
Dipping into the gig economy outside of a steady day job is one thing. But is full-time gigging really for you? A few conditions will improve your chances immensely:
• Do you have a saintly, bread-winning spouse to help fill income gaps?
• Are you free of dependents, expensive hobbies and vanity possessions, including pets larger than goldfish?
• Are you cool with handling most of if not all of your own accounting, project management and the godawful networking?
• Does your ability to manage anxiety equal that of a discount shark dentist?
• How long can you go between checks without completely unraveling, abandoning your gig and getting a job at the local pizza joint? More than six weeks?
If you answered yes to at least two of these five questions, I’m liking your chances.
Submitting to the gig economy wasn’t my plan. It’s a situation I blundered into around 2003.
I was, in theory, working as a freelance travel writer. At least that’s what I told everyone to save on time and awkward questions. But sometimes months would go by between travel writing assignments. Meanwhile, I did mind-numbing copywriting, wrote buyer’s guides for tech products or played guide/sherpa/fixer for people visiting Minneapolis on business.
Eventually, gigs appeared in the form of all-expenses-paid invitations to conferences in attractive cities to disseminate “expert” travel advice and “coach” aspiring travel writers — without ever proving I was competent enough to do either.
I grinded out a decent living doing these things for nearly 12 years, partly through a disastrous recession. Yet I constantly found myself wondering: “When will the luck of this harebrained ‘career’ of mine run out? Will this be my last gig? Are there any checks in the mail today? No? I’m doomed!”
Imposter Syndrome is a common freelancer condition.
After enough time on this roller coaster of uncertainty and colon-shredding stress, given the opportunity, a sane person would gladly opt for a steady job. And I did — for a while. For two years I managed the tourism department at a local, particularly large shopping mall. And the novelty of getting paid every two weeks, no matter how sucky those weeks were, never wore off. Plus, I didn’t have to do mental accounting of the previous month’s finances every time I ordered an expensive meal or drinks. And, oh, the splendor of paid vacations!
Side hustles, full-time gig
But I’m back in the gig game, baby. Right now, as you’ve noted, I’m writing a 900-ish-word essay about the gig economy. Tomorrow I will lead a group of travel writers around my beloved city of Minneapolis, showing them all the pretty things (and U.S. Bank Stadium). I co-host a podcast. I have a couple of simmering projects with a virtual reality company. Next month, if all goes well, I’ll be writing copy for a travel website. And soon I’ll start renewed promotion for my book, “Backpacking With Dracula,” which always gets a nice media boost around Halloween. But these are merely side hustles to my full-time gig.
I launched a travel marketing and PR agency a few months ago. I mainly work with international destinations and brands wanting to raise awareness and their media profiles in the U.S. I spend most days working to get media coverage and helping to craft marketing campaigns for a treehouse “village” hotel in the Dominican Republic, a pedestrian navigation travel app out of Tel Aviv and a Canadian province immediately to our north. Soon, I’ll blast off for a travel media conference in Ireland to woo more clients.
It’s all going fine for a fledgling business, but I sometimes find myself wondering what I was thinking re-entering the gig economy. Sending cold e-mail pitches that never get answered. Building relationships and putting out fires with people two, six and nine time zones away. Expectantly opening the mailbox every day and only rarely finding something I can trade for food and shelter. RIP, paid vacations.
There are perks, clearly, or this would simply be textbook masochism. My commute to work is literally three seconds. I can take a two-hour nap or a three-hour lunch. Some days I don’t even put on shoes or a shirt until late afternoon. I’m the boss. I can fire people (read: clients) when they become prohibitively aggravating. They can, naturally, also fire me, but I’m still the boss.
And who knows, in a few years I can jump the shark and reinvent myself as a gig economy coach/wizard/guru/Jedi, guiding the next wave of giggers into a world of financially wobbly, cautiously carefree, glorious freedom. I’d better get cracking on a snappy self-help book title.
Leif Pettersen (@leifpettersen) is a travel marketing and PR professional and champion juggler.