Life On My Own Terms

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So far this week, I’ve met my cousin for lunch, enjoyed an afternoon with a childhood friend who was in town and spent several hours helping my brother and future sister-in-law with their wedding planning. Tomorrow I’ll meet a local friend for our weekly Happy Hour, which we sometimes start at 3:30pm. I’ve gone to a 12:00pm doctor’s appointment, managed a few pathetic mid-day runs and done my grocery shopping at 11:00am on Monday, in a blissfully empty store with no lines. And not once have I had to use personal time, sick time or play hooky. That’s not because my boss is super cool (although I think she is). It’s because I don’t have a boss. And that’s what allows me to do the things I want to do (like meeting my cousin for lunch) and the things I have to do (like a doctor’s appointment) on my own terms. I don’t have to ask for approval or push all of my personal errands and social commitments to weeknights and weekends. I create my schedule, which in effect creates my life. And I love it.

A huge part of my personal happiness is dependent on freedom. Freedom to create my own work schedule, freedom to do something I enjoy, freedom to answer emails and phone calls the way I want to—not the way someone else tells me to—and freedom to decide how my day is going to look. In two of my career past lives, I found myself working as a school secretary. At both jobs, I was in charge of phones and entry into the buildings. That meant that if I needed to use the bathroom, I had to first find someone to cover the door and answer the phone while I was away from my desk. Sometimes no one would be available so I would say Forget this! (not the exact words I used), run to the bathroom and hope no one called or rang the bell for three minutes. I felt chained to my desk and it made me miserable. (Being overqualified and bored to tears didn’t make things any better.) It sounds like such a small thing, but not being able to use the restroom, essentially without asking permission, drove me crazy.

The lack of freedom was extremely frustrating, and it didn’t help that I wasn’t passionate about any of the industries I had worked in. Prior to figuring out what I wanted to do, I had been a real estate agent, a school secretary and held a few Administrative Assistant and Office Manager positions in small businesses. I ended up hating all of those jobs. I liked my coworkers and made some lifelong friends, but I didn’t like the work, the hours or the answering-to-someone-else part. My work cycles—which rarely lasted over a year—would go like this: Nerves (First month, “How do I do this job? I don’t want to mess up!”), Satisfaction (Next two months, “I got this. And everyone is so nice!”) and Dread (Months 4-12, “This is crushing my soul. How many days until Friday?”). The Dread stage felt unbearable and lead me to this epiphany: I can’t spend my life doing something that I hate. Like most people, I have to work full-time to survive, and that means the majority of the hours in each week are taken up by work. I decided I could not stomach the idea of spending most of the next 40ish years being miserable. So I opened my own business and didn’t have that problem anymore. The End!

Nope, it for sure wasn’t that easy. Nothing about my journey has been particularly easy, but starting my own business was one of the best decisions I ever made. (On par with deciding to go to college, living in Charleston during the winter months and committing to twice yearly Brazilian Blowouts to eliminate my mortal enemy, Frizz.) I stumbled upon my business idea during a driveway wine party—exactly what you’re picturing—with my friend, Caroline. I was 24, hating my two jobs (school secretary and part-time admin assistant at a real estate company) and freaking out about what I was going to do with my life. Caroline said “Why don’t you become a makeup artist? You love makeup!” How did I not think of that myself?!?!

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I grew up with no sisters and a mother who owned maybe four beauty products, but I had always loved makeup. One of my mother’s four products was a Mary Kay lipstick and eyeshadow palette, with all of the frosty, vivid shades a 1980s palette should have. And I put them all on anyone who would let me near their face. By high school, I was making weekly trips to CVS to empty their beauty aisles as best I could. Then I would apply that makeup, in all of its late 90s white-eyeliner-and-glossy-lips glory, on whichever friend came over after school. The college years were similar, but with bronzer and black eyeliner. I read everything I could about makeup (this was before YouTube, so tutorials were not an option) and continued to use my friends as practice models. I’m perpetually chasing the runner’s high—put intended—but I never get there. But if you want to talk being in the zone when not running, I’m there when I’m doing makeup. It’s 150% focus, and I neither feel nor think of anything else during it. When someone looks in the mirror and says “I love it!” after I’m done, I feel true joy.  

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The conversation with Caroline happened two years after college, during a brief stint living with my parents. I didn’t wake up the next day and quit my job to become a makeup artist, but I started doing my research and taking steps to make it happen. I moved back to my college town of Newport, RI—which had always been the plan—enrolled in Esthetics school full-time, picked up a part-time waitressing job and went full steam ahead with my entrepreneur life.

I opened my business—then Allison Barbera Makeup Artistry—in summer of 2008. It was just me, a freelance makeup artist with a passion for doing wedding makeup. By 2012, I had hired four Independent Contractor hair stylists and makeup artists and renamed my company Allison Barbera Beauty. In 2017, my company—now Allison Barbera Beauty LLC—has 13 Independent Contractors and more job requests than we can accommodate. I am currently looking into opening locations in other areas of the country. As a business owner, I work more hours than I did at any other job and I have not taken a full day off (meaning not one email, voicemail or text check) since 2008. But I do two things I’m passionate about—makeup and running a business—and I have both the schedule and financial freedom I always wanted.

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For those thinking about opening a business, I say go for it. But be smart about it. Do your market research, hire an attorney and get yourself an accountant who works with small business owners. I don’t advise quitting your day job unless you have another source of income or savings to cover all of your expenses if your business isn’t profitable for a year or two. When I started in 2008, I had some money saved and three credit cards to be used if needed (and oh, were they needed). I spent my first two years as an entrepreneur working different full-time day jobs during the week while doing makeup and building my business on nights and weekends. That was frustrating, but had I gone full-time with my company before I had the income to support myself, I would have been stressed, broke (although I still had those periods until almost five years in) and discouraged.

Above all, if you want to start your own business, have patience. Lots of it. Contrary to what you may hear, no one is an overnight success. Building a business takes time, and there is no shortcut around that. But if you have a solid business idea, a plan, passion, a strong work ethic and the willingness to temporarily sacrifice some things (like days off, consistent income and a lot of your social invites), you have a fantastic chance of succeeding.

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I am truly so happy with my life, and a big part of that is due to my career. I also have the best family I could ever ask for and a ton of wonderful friends, both of which are as important to me as career satisfaction. I live in two places I love—Newport and Charleston—which was one of my main goals when I opened my company.  Being an entrepreneur feels less like a like a job and more like a lifestyle. And it’s the exact lifestyle I wanted.