Being a Boss, Part 1: The Inception

Entrepreneur, girl boss
Me at 24, pictured here not having a panic attack.

I believe life is too short to wish time away. We get a limited amount of time here and it’s a damn shame to hope all of the days until the weekend/a vacation/a move fly by. I mean, it’s natural to look forward to something you’re excited for, but I don’t like the idea of consistently living life like that. Yet that’s what I found myself doing before I owned my company. When I worked at other jobs–no matter how flexible my boss was or how awesome my coworkers were–I always found myself hating Mondays and living for the weekends. I wanted to hit fast forward on the hours between 9-5, Monday through Friday, and I wanted my nights and weekends (except for time spent at the gym or running) to slowwwwwly pass. Unfortunately, this is not how time works. I knew if I wanted to be happy, I had to find a way to take back my time, but also make an income because Daddy doesn’t fund my life and I’m not cut out to be a sugar baby. (I would rather wear rags that I paid for than a Versace dress that someone else bought for me.) So I opened my own business, which means not only do I no longer wish away days of the week, but I seldom even know what day it is. That’s the short story.

This is the longer story, which you’ll need to know to understand what I’m going to throw down in this series of posts. I moved from New England to south Florida solo after graduating college. I spent two years there, mostly getting tan and avoiding palmetto bugs. I worked as an office manager at two companies, something my 7 years working for the small business my father owns had prepared me for. While I made some fantastic lifelong friends in some of my coworkers, the jobs I was doing were not making me happy. I did, however, learn some valuable customer service skills and admin systems that I use now. I also saw examples of how to be a bad business owner–screaming at your employees, writing angry emails to clients, jetting off to Miami for three days and neglecting your business–which I subconsciously filed away and remembered when I opened my business.

The summer I moved back to New England was a tough one. I luckily found work as a full-time school secretary and a part-time admin at my father’s company, but neither job was what I wanted to do. The problem was, I didn’t know what I wanted to do. I could only pinpoint the fact that if I was going to spend the majority of my hours working, it needed to be something I enjoyed. What did I enjoy? Writing always came to mind. I had harbored fantasies of being an author since I was young. That summer, I signed up for the equivalent of an online writing course (this was actually done via the mail, because I’m old), but it was more as a hobby than in preparation for a career. I knew making a living from writing was a rough path and I was still at the point where I needed stability and consistent income. So what should I do?????? This question was the cause of my daily freakouts. (Other causes: stupid boys, gaining one pound, having debt, stupid boys, thinking a friend was mad at me, bad hair days and stupid boys.)

This big question was eventually answered by my close friend and bombshell Italian actress lookalike, Caroline. You would think I would clearly remember this defining moment of my life, but what I have instead is a vague memory of what I think happened. I believe we were sitting in her driveway on lawn chairs, having a wine party. (She lives on a dead end and her husband is too nice to run us over, so we were safe.) I was hardcore venting to Ca–as I still do–gearing up for another freakout about what I was going to do with my 24 year old life. She reminded me how much I loved makeup– something I had been into since I was 5–and suggested becoming a makeup artist. We talked about Cosmetology school, but I wasn’t interested in doing hair. She then mentioned that our friend Lauren was looking into Esthetics school, something I had only first heard of earlier that summer when a psychic told me I would be going to Esthetics school. (Did you just get the chills?) I didn’t make a definitive decision then, but this is the first memory I have of thinking, I could do that and like it. I may be wrong about the details (Paesana, please correct me) but when I think of how this whole career of mine started, this is what I go back to. The moral is if you don’t know what you want to do with your life, have a driveway wine party and let one of your best friends figure it out for you.

So I jumped into action the next morning, right? Nope. Because first, I had some serious shit to address. I had been feeling sick and exhausted for a while and when it got to the point where walking from one desk to another in my father’s office was taxing, I knew I had to do something. But doing anything was so hard, because I had zero energy. Luckily my parents stepped in and got me an appointment with Dr. Qutab, a naturopath and MD who approaches health issues from an Eastern medicine and ayurvedic perspective. I had been to plenty of Western medicine doctors who would run a few tests and say that I was fine. After extensive testing with Dr. Qutab, it turned out I was in no way “fine.” I had several health problems–from hormonal to un-diagnosed allergies to pre-cancerous issues–and we immediately began to correct those with diet changes and supplements. To say that he changed my life is a giant understatement. I am telling this part of my story because I know that if I hadn’t gotten help with my health issues, I wouldn’t have had the energy to take the steps to start my career. I firmly believe that if you don’t physically feel well every day, you won’t have the emotional and mental energy and the motivation to make big changes in your life.

Even though I was feeling a million times better and shedding that weight I had been struggling with for years–turns out some of the issues I had were keeping that from happening–I wasn’t a complete Suzy Sunshine ball of energy. I had struggled with depression in college and I was, at this point of my life, much more of a pessimist than an optimist. Not feeling horrible every day certainly helped, but I still had intense worrying sessions. How would I pay for Esthetics school? (Sallie Mae.) Would I like it? (At times.) What if I failed the state licensing exams? (Oh, please. No math is involved.). What would I do after I got licensed? Work at a spa? Makeup counter? For a cosmetics company? (It’s going take you a bit to figure that out, but “no” to all of those.) I don’t know if it was that I was in my mid-20s and everything feels hard then, or if my Type A personality made it that way, but I certainly was not carefree and confident in my decision.

Because I had, at some point, made my decision. I would move back to Newport, RI–the town I had fallen in love with when I went to college there–and enroll in the closest Esthetics school. I would work an office day job and go to school on nights and Saturdays. I did move to Newport, but I ended up going to school 8:00am-4:00pm Monday-Friday and waitressing nights and weekends. I graduated and got licensed in July of 2008 and embarked on my new career. A few years before, I had been adamant about never owning my own business, as I had worked in several and seen how hard it was and how much responsibility fell on the owner. But I realized that because of my stubborn,  independent nature and my desire to not be stifled creatively if I wanted to enjoy my work–the whole reason I went down this road–I would have to go out on my own.

It would take me two years of working at full-time jobs not in the industry to do that, but I got there. That’s for Part 2, which I’m sure you are dying to read.  That will explain my early years in business, because this post is already too long. Part 3 will be a comparison between entrepreneurship and working for someone, as I see it. So if you are considering making the jump into entrepreneurship and are more of the analytical type, you may want to wait for Part 3.

I want to be clear about one last thing before you leave me for Snapchat. When I use the word “boss,” I mean because I am my own boss. I am technically not the boss of anyone who works for me, as they are all independent contractors. I’m more of their agent, procuring work and setting it up so they can do the magic they do. In my view, one person doing freelance is as much of a boss as the CEO of a Fortune 500 company. If you are making all of the decisions for your career–the jobs you take, the hours you work, the way you market, etc.–and the responsibility of it all ultimately falls on you, you’re a boss. So go on with your bad self.

Have a beautiful day 🙂

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