What No One Tells You About Being Your Own Boss

In 2016, Mari Andrew made a New Year’s resolution that, albeit simple, would eventually cause a seismic shift in her life and career (which, up until 2017, included stints as a writer, teacher, and working at a law firm, amongst other things). She vowed to post one illustration to Instagram every single day. Four years later, that daily habit (which she continued diligently for two and a half years) has garnered her more than a million Instagram followers, two book deals, a freelance career as an artist, and the opportunity to teach classes on how to experience creative transformation by being intentional about a daily artistic practice. 

While Andrew’s leap into the freelance world proved worth the risk, it wasn’t without its unexpected hurdles, and the important life lessons that shook out from them. Because however prepared you may be to actually make the switch from a 9-to-5 to being your own boss, the hardest part is often what comes next — the things no one tells you about. That’s why we tapped three women, including Andrew — who all use Skillshare to teach everything from branding 101 to establishing daily creative habits — to tell us the most surprising (and most important) lessons they’ve learned after becoming their own boss.

Mari Andrew’s habit of posting one Instagram a day, which eventually led to a full-fledged career as a freelance illustrator and author, is a testament to the advantages of starting small. You don’t have to abandon the stability of a 9-to-5 overnight in order to earn your stripes, and when you do eventually make the jump, be realistic when setting expectations and goals for yourself.

“You should ask yourself, How do I want to feel at the end of a season or at the end of the year?” she says. “And then work backwards from that, envisioning the person you want to be. I love setting goals, I'm naturally a disciplined person, and I think people forget or don't realize how much fun it can be to work toward that.”

“An interesting challenge to get used to when you're working for yourself, especially in a creative career, is that it really bleeds into every part of your life. I think a lot about the relationship between work and creativity — what is my job versus what is my work? — because I'm always working. Because of that, my creativity has become almost like a relationship to me. It's a relationship that I'm always working on.”

Cyndi Ramirez-Fulton and her husband Adam opened Chillhouse — the self-proclaimed “destination for modern self-care” that pairs facials and manicures with an in-house café — in 2017 with one goal: to create a space where New Yorkers could go and practice wellness on their own terms, without being told how to do “self-care.”

“We started to think about ways we could really own the [wellness] conversation,” Ramirez-Fulton says. “It felt like something was missing in the industry in New York: a place where you can enjoy the space and feel like you're in a more relaxed state, versus feeling like it's just the traditional coffee shop or just a traditional bar, you know? We really wanted to create a kind of hub that served lots of different needs.”

Three years later, the original Lower East Side Chillhouse location has revamped into a “face and body studio” offering massages, facials, manicures and pedicures, and infrared sauna sessions along with matcha lattes and a full service coffee bar. And in November 2019, a much larger Soho flagship with a new food and drink menu opened its doors. 

Ramirez-Fulton didn’t open Chillhouse with wellness landscape expertise, and getting acquainted with the ins and outs of a new industry meant lots of learning experiences (many of which she now divulges in her own Skillshare class on how to build an aspirational brand in the era of Instagram). Her best advice? Know your industry like the back of your hand (even — and especially — if you plan on disrupting it). If you don’t have that knowledge going in, come prepared with a willingness to learn and adapt. 

“I just assumed we were going to open up this cool, chic space and people would want to work for us. But it was very obvious from the get-go that we had to prove it was more than just a cool concept. That was humbling. You have to treat the industry with respect and understand what’s been done before and why.”

And with the trial and error of becoming your own boss, remember that sometimes it’s okay to fail. “If you find that there's something that just truly isn't really working, don't be so hard on yourself and don't be so emotionally attached to something that you are unwilling to make any changes,” she says. “Don't be afraid to ‘fail forward.’”

If you ask Laci Jordan, she landed the gig of illustrating for R29 Unbothered’s Go Off, Sis podcast because she manifested it: with enough comments, DMs, and story mentions on Instagram to make almost everyone on the team take note. It was her “fiercest play on manifesting [her] future yet,” and a testament to the fact that Jordan believes in going after what you want, no holds barred. 

Just a few years prior, Jordan was working full-time as a graphic designer, but she didn’t know anything about vector illustrations — the illustration style she’s now known for — until she started taking classes on Skillshare (she now teaches her own class on beginner digital illustration). After years of coming home from her 9-to-5 and working on side projects until 2 or 3 in the morning, she’s now freelancing full-time, illustrating for an impressive array of brands and working on cultural partnerships for important moments like Black History Month. 

As a freelancer who is the boss of her own schedule, time management has been the most challenging thing Jordan has had to navigate. Learning how to recreate the structure that she had in her previous 9-to-5 turned out to be an important lesson in self-discipline. “I was sort of under the impression when I quit my job that I would have all this time, like a portal of unexpected time that I would have all of a sudden. But there's a lot of days where I'm like, What did I do today? Like wait, What happened today? I realized that when you work a corporate job, you sort of have this machine, this schedule, and when you can quit that job you have to essentially recreate the same machine for yourself, for your own work.”

Jordan demands a lot of herself and her work, but that doesn’t mean she isn’t also making space for self-love; in fact, it’s a key part of her entrepreneurial philosophy. “It’s intimidating, but you really have to follow this urge to just figure out who you are. Just keep pushing,” she says. “I think a lot of people look forward to a certain point in life where you can say, Okay, I have it all figured out now, and that doesn't really exist. I never really have it all figured out. You just have to keep your head down and focus on you.”