Confessions of a First World Mercenary: Lessons From Hacking the Gig Economy Every Which Way

Since graduating college, I’ve avoided the nine-to-five grind in favor of a two-to-six lifestyle. Working two-to-six jobs, that is. Currently, I work as a comedy writer, stand-up comedian, SAT tutor, Ikea assembly-man, delivery guy, and film editor. On a surprising side note, I don’t have commitment issues in relationships.

When I share my list of jobs with people, they like to call me “resourceful,” or a “man of many hats.” I’ve learned to listen for the underlying tone in those statements, which ranges from purely dismissive to a reflective form of jealousy. This guy doesn’t starve and seems happy. Why do I put a suit on every day again?

I am happy and fed, but it took time to reach a level of satisfaction. While the only constant about freelancing is its unpredictability, I have picked up a few lessons that can help any first world mercenary stabilize a freelance career.

Time is money

Yes, this cliché sounds like something a slick yuppie who curses out waiters would say, but thinking of time as currency can be healthy. As freelancers, we all have to make tough decisions about charging by the hour or by the job, and every move we make represents an opportunity cost.

Two months ago, in the midst of panicking while gathering rent, I looked into trimming my budget. A friend told me if I took a defensive driving class online, I could cut my monthly car insurance premium by 10 percent for three years. I damn near signed up on the spot before realizing the class cost $25 and six hours to complete. I would have saved $9 per month, or about $300 over three years after accounting for the class fee, so I chose to spend those six hours working.

Almost every decision a freelancer makes has an opportunity cost — cooking, going to a bar, even reading this article. Have a life, but be cognizant of the value of your time. And focus on cutting expenses during a slow spell, instead.

You can never whack all the moles

Remember that funhouse game Whack-A-Mole? You play it every day to make rent. Sure, we freelancers are a tad less violent with our clients than with plastic moles, but once the game begins, our only goal is to knock out as many gigs as fast as possible. Remember, though, there’s no way to win at Whack-A-Mole, just like there’s no way to win a freelancing career. There are high scores to be had, but gunning for one every time you play will leave you frazzled, crazed, and with Carpal tunnel syndrome.

Know when to buy a round

It feels great to finish a week of gigs with double or triple your normal haul, but some of us find a way to lose that money quickly. In my mid-20s, it didn’t take much to blow $100 at a moderately-priced bar. With a swelling ego — “I rocked my gigs today!” — I was suddenly throwing down on Irish car bombs for friends and bartenders. I’ve seen temporarily-flush freelancers do that with dinner parties, vacations, and gadgets. The point is: If you find yourself spending as hard as you’re working, you’re probably working too hard instead of maintaining a proper work-life balance.

Bring your sword to negotiations, but don’t necessarily use it

I’m not saying you need to go all Kill Bill on every employer, but always address two things with prospective clients: Get as much detail as you can about each gig before committing; and establish firm boundaries for what you won’t do. The easiest way to build a good working relationship is for both parties to have realistic expectations.

When I tutor for the SAT or ACT, the money can be straight-up addictive. Four hours of work per week can pay my rent, utilities, and phone bill, so I tend to give those jobs priority. Last July, I landed a wealthy Manhattan client whose daughter was starting junior year, and all I could think about was fourteen months of consistent tutoring. The mom believed the daughter was Ivy League-bound, but after a practice test, it was clear she needed significant improvement to get accepted by any top-tier U.S. college. Yikes. But since I was afraid of losing easy money (and a little too cocky about my tutoring skills), I told the mother we’d get her daughter’s scores where they needed to be. For all of you non-tutoring freelancers out there, what I told the mom was the equivalent of applying for a blogging job and promising to write a hit serialized novel, Dickens-style.

Of course, when it came time to take the test, the mother and daughter didn’t have realistic expectations. The student improved her score 150 points over six months, which under normal circumstances would have earned me a big, ole thank you and a few referrals. Instead, I got fired.

I survived, and eventually, found a replacement job. When you work a two-to-six lifestyle, there’s always another gig to take on, another mole to whack.