Being a Boss, Part 3b: The Good Outweighs The Bad

Sullivan's Island
Me in Charleston, SC, where I’ll be spending my winters. I couldn’t have ever done anything like that before I was an entrepreneur.

It’s the finale! I’m going to miss writing these. If you’ve enjoyed reading these half as much as I’ve enjoyed writing them, then this series has been a success. If you haven’t enjoyed reading them, then what are you doing back? I’m sure there are some Buzzfeed “articles” out there waiting for you.

So let’s finish out this Pros and Cons of entrepreneurship list. After reading these four posts, you should know exactly what you want to do with your life. I’m playin’! But if something I say kicks your ass into gear, then I can and will take the credit. 😉

Job Satisfaction

Pros: You get to do something you enjoy. If you start a business, you hopefully choose a career that involves something you enjoy. Being passionate about something–or at least being very interested in it–is way better than working in a field you have zero interest in. There may come a point when you stop doing what the popular business book The E-Myth Revisited calls the “technician” work–in my case, doing makeup–but as the entrepreneur, you are still in the industry you want to be in. In my experience, working in a field you love makes everything considerably easier. I’ve had my company for 8+ years and I still love opening a new mascara, knowing it could become my new favorite. I still love watching YouTube makeup tutorials and learning different techniques. I still love discovering a new use for a product. And I really still love the feeling I get when someone looks in a mirror after their makeup is done and genuinely smiles. I didn’t have that kind of passion about real estate, air quality testing, the administrative side of education, food service or any other industry I previously worked in. But the beauty industry? That’s my jam.

Cons: It can take away some of your passion. As an entrepreneur, particularly if you are doing a lot of “technician” work, you may find that after a while, you like that part of your job less than you did when you started. It’s probably not that you really like it less though. It’s more likely that you feel weighed down by the business side of entrepreneurship, which requires a lot of energy. I think particularly in creative fields, having enough energy to both create and to manage, market and grow your brand can be very challenging. Speaking for the hair and makeup industries (and I think this example can be adjusted and applied to any creative job), it takes a lot of energy to listen and understand the ideas a client has and successfully execute those ideas so they are happy with their look. A lot can be lost in translation, but a good makeup artist or hair stylist can sort through it. When you give your all to creating what the client wants and then repeat that several times a day, you’re likely drained when you’re finished. But as a business owner, you probably have emails and calls to answer, invoices to send, products to order and a million other things to do after you finish with clients. For some people, that takes the joy out of doing their creative work. Everyone has their own balance they can handle, and the key is to figure that out. In the creative field, you can sometimes find a way to do more technician work than “business” work by working for an agency or as an Independent Contractor for a company. In those situations, you still have to build your brand and do some business work, but the agency or company you work for will offer you the jobs and coordinate the details in varying degrees. (If you hire others though, you immediately step into a managerial role unless you hire a manager.) If you want your business to grow, you will eventually have to find people to do most of the technician and managerial work, but eventually, you’ll have to spend more of your time on being the big picture entrepreneur. (I’m again referencing The E-Myth Revisted. Anyone who owns a business or is thinking about opening one should read this.)

No Supervisor

Pros: You don’t have to answer to anyone. If you have a great idea, you can implement it without being impeded by policies or waiting for approval from your supervisor. No one is going to ruin your day by giving you a shitty yearly review or declining your request for one telecommuting day a week. You set your dress code, you do any hiring and firing and you decide how to handle every situation. You don’t have to worry about your boss’s micromanaging or hot and cold personality. When you own a business, you (hopefully) learn from your mistakes–because you will make plenty–instead of worrying those mistakes will get you fired. No more heart-dropping-into-your-stomach feeling when your boss says they need to talk to you. I’ve had some great bosses and some horrible ones, but the one in the mirror–even with her shiny t-zone and thin upper lip–is hands down my favorite. She lets me do what I want and blasts DMX when she’s angry, so I know we understand each other.

Cons: You have a bunch of mini bosses. Each client/customer is your boss in a way. (This may be more applicable if you offer a service.) If they book services or buy products from your company, they are essentially hiring you. And if they decide to no longer use your company’s services or buy your products, they are essentially firing you. You could have several mini bosses at a time and it’s literally your job to please all of them. You need to be disciplined. It’s easy to slack off when no one is over your shoulder. If you are not self-motivated, your business will crumble. Sorry, but it’s the truth. You may find it’s easier to be self-motivated when you are interested in your job, but if you still think you would need a constant push or the threat of someone who could fire you, stay away from entrepreneurship. This rarely happens now that I’m in my mid-30s, but in my 20s, I caught some crap from friends when I declined invites to go out on weekend nights. I very much wanted to be with them, but I also owed it to my clients to show up to their wedding awake, not hungover and sans shaky hands (never a good thing when applying eyeliner). If you are the type of person who will not only consistently go out the night before an early job but will stay for “just one more drink” each time, your business will feel like a 5 star hangover. Except instead of killing your Sunday with its headache and nausea, it will kill your whole company.

Entrepreneurship is not for everyone. And that’s okay! There is no shame in being an employee. You can be fulfilled and happy with your career whether you work for yourself or someone else. If what I describe as benefits don’t sound that great to you, or the bad seems to outweigh the good, then this probably isn’t your path. If you hate your current job, it doesn’t mean you should quit and open your own business. You may just need to be in a different industry. If your heart is in music but you work in banking and are miserable, see what steps you need to take to break into the music industry.  It might take a while, but so what? Here’s where I insert one of my favorite quotes: “Don’t give up on a dream because of the time it will take to accomplish it. The time will pass anyway.”

Personally, my worst day working for myself is still better than my best day working for someone else. In the years I spent as an employee before I knew what I wanted to do for a career, I felt a great sense of despair. I knew what I was doing was so far from what I enjoyed, but until my friend Caroline suggested Esthetics school, I didn’t know how to take something I loved and turn it into a job. In the two years I spent working for other people after I had opened my company, I felt frustrated. I so badly wanted to be out on my own but couldn’t do it yet financially. Now that my company is established and I’m financially stable, I feel hopeful, excited and determined. There is a lot of opportunity and I have big plans. I have days that I’m angry that my website is down or annoyed that I can’t get an answer that I need from someone, but it’s rare that I stay like that for the entire day.  I think the difference is that I don’t dread my job now. I don’t wish away days. Sure, there are some jobs or clients I know will be more challenging, but nothing is ever so bad that it makes re-think my whole career.

I love that I can basically do what I want. To get to that point, I did have to do a lot of what I didn’t want–doing unpaid shoots early in my career to build my portfolio, working 14 hours on set then four hours running my business when I got home, fighting with my accounting software–but the longer I am in business, the more I can turn down work I don’t need or want and hire other people to do the things I don’t like. (In fact, I have stopped doing or outsourced all of those examples.) And that’s not a hedonistic tactic. Freeing my time of the things other people can do–just as well if not better than me–is smart. It allows me to focus on expanding and growing the company, coming up with the big ideas and then making them happen.

I think it comes down to what you value. An important value for me–which you may have picked up on–is freedom. I need to be able to create a life I want without being held back, and entrepreneurship is the only way I could see to make that happen. Things might have been easier if I loved my previous jobs or not felt this deep need for freedom, but that’s not how it worked out. I know without a doubt that I’m happier as an entrepreneur than I could have ever been as an employee.

In the Usher/Lil Kim collabo “Just Like Me,” Kim raps “If I had one wish in the world, I swear to God, it would be for girls to rock pearls, straight out the oyster.” I don’t feel that strongly about pearls, but I do feel strongly about career satisfaction. Work takes up such a huge chunk of time for most of us, so I truly hope that you have found or will find what makes that time the most enjoyable, lucrative and flexible for you, whether it’s as an employee or entrepreneur.

Have a beautiful day 🙂

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