Risk-takers who drop everything and follow their dreams get a lot of attention. Like the twenty-something who abruptly traded his nine-to-five for a nomadic lifestyle of filmmaking from a remodeled cargo van, and others who share a similar narrative. For those of us still pushing through our endless daily grid, the delicious thought of waking up one fine morning and pulling a Swedish House Mafia by leaving the world behind has probably crossed our minds at least once. Hell, tons of TFD contributors have done it, too, and why not? Sometimes life seems to be more about bills, budgets, and whatever else #adulting means, and less about the pursuit of happiness. Wasn’t that supposed to have been the point?
Regardless of what those dreams are, the truth is that not everyone can abandon their financial or personal obligations to chase them. That’s why others do so differently: slowly, with intention, and by hanging onto a paycheck whenever possible. Over my seven years in New York City, I’ve known artists, entrepreneurs, and experience junkies who happen to also have jobs that pay the bills. In other words, their side-hustles support what’s, for now, a side-passion.
Two such people are my former roommates, Leila Bicos and Jen Hanley. Both are serial side-hustlers who’ve created, produced, and funded many of their own film projects (including two entire seasons of a web series). They were gracious enough to share their financial experiences with me during our long drive down to the Women’s March on Washington last month. While our discussion was far from a comprehensive exploration into this idea, five themes from it emerged that might inspire (or deter!) you from adopting their unconventional lifestyle for yourself.
1. You’ll have to work a bunch of side-hustles — and you can’t be picky.
When seeking survival jobs as a creative person, flexibility is the major key. From Leila and Jen’s perspectives, the best approach to keeping a schedule flexible while addressing your financial needs is to juggle as many side-hustles as your sanity allows. The goal is to extend your network as much as possible in order to help stem the ebb tides of both creative and money-making opportunities. Those contacts will come in handy during moments when you find yourself without a passion project to occupy your time and/or enough in savings to cover rent, bills or other obligations. From bartending, nannying, freelance work, to lipstick reading (?) — there are many opportunities to earn money out there, and as we TFD readers know, there is no shame in your side-hustle game.
2. Burnout is real, so you need to set boundaries from the beginning.
Pursuing a career in the arts requires a fair amount of drive. Employers value a strong work ethic, so it’s fairly easy to get sucked into a side-hustle. Both Leila and Jen had countless stories to share about times where initially-low-key gigs slowly morphed into what essentially became full-time jobs. The best way to mitigate this while maintaining a reputation as a hard worker is to be open and upfront with employers about your creative aspirations. Remember, their business might very well be their passion, so be respectful but clear about the fact this job your livelihood, not your life. Seeking gigs where employers don’t uniquely rely on you, where your help is needed but can be easily be replicated by just about anyone else, is ideal.
3. You have to be prepared to walk away from a side-hustle that’s no longer working for you.
Juggling several side-hustles and a side-passion at once is stressful, so be mindful of your own limitations. Leila and Jen acknowledged that the right balance between both efforts is different for everyone, quite difficult to maintain (especially at first!), and can take years to figure out. This is another reason why establishing boundaries and communicating with employers honestly is crucial. Surprise is not a reaction they should have once you do approach them about the possibility of taking off days/weeks/months to focus on a passion. Your rapport will likely be tarnished, as will the possibility of working for them in the future. If, however, despite your best efforts, an employer disrespects your request, they’re not worth keeping around in your money-making arsenal, anyway.
4. Always live like you’re broke, because you very well might be tomorrow.
Saving for the sake of saving is an unfortunate aspect of this lifestyle. It’s frustrating, counter-intuitive, and not for everybody. Even when they’re not working on anything creative or need to financially, both Leila and Jen obsessively pad their savings accounts. That’s because in the past, not doing so has gotten them into trouble more than once. Successfully plugging back into your money-making network after having taken time out to focus on a passion is rarely immediate. There is no such thing as job-security and no guarantee money-making opportunities are available, even with an impeccable network and reputation. As Jen put it, “Hoarding your money is an investment in yourself for that moment in the unforeseeable future when you’ll want the freedom to spend it.”
5. Be prepared to spend more money on your side-passion than you earn from it…for a while.
Leila and Jen rely on their network of like-minded hustlers to save money on things like headshots, reels, and pre/post-production services — necessary costs in their field. Expenses like these stack up quickly and unexpectedly, especially for someone just starting out that might not have similar connections in place. Unpaid internships and taking on low-budget or no-budget creative projects are invaluable ways to slowly build this network while gaining experience as well. Sadly, someone who cannot afford to work for free at all will be disadvantaged, since this “paying your dues” phase lasts for an uncomfortably long period of time in creative fields like theirs. As Leila said, “Everything will cost more money than you think it’s going to, and everything will take longer than you think it’s going to.”
Laurin is a researcher, yogi, amateur photographer, and ex-Californienne living in Manhattan who suffers from an acute form of wanderlust. Follow her on Twitter here!
Image via Unsplash