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!"
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!
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.