5 Realities Of Self-Employment: Is It For You?

It's currently 10 am on Monday and I'm sitting in my sweats, wearing a charcoal face mask, catching up on Modern Family and shoveling chocolate chips in my mouth. Could substitute Monday for: Tuesday, Wednesday, Thursday, Friday, Saturday, or Sunday. But life wasn't always this glamorous, friends. Could substitute glamorous for: magical. I spent years shuffling around from one corporate job to the next, just hoping, trying to find my place in that unspeakably pointless, life-zapping rat race. For more on that read: How To Work For Yourself and Quit Cubicles Forever.

The world is full of entrepreneurial hopefuls, creative minds, and people just wanting freedom. But are you cut out for self-employment? There have been many times I've wondered if I am. Creatives + free spirits hate to be stuck in a cage, but the downside is not all of them have the ability to reign it in and do what it takes to work for themselves.

For years, I spent morning after morning throwing my hair into a ponytail, after oversleeping due to the overwhelming reality that as soon as I got out of bed - life would start sucking again. I grabbed a protein bar and rushed out the door, only to find myself stalling in my car, contemplating whether or not I should just stay there and breathe in the exhaust for awhile. I realize that sounds like a slight dramatization, but if you're a right-brained creative stuck in a gray cubicle all day and staring at numbers, you feel me.

A little background info for you. Not only have I done lots of corporate jobs, I've owned three different businesses at this point in my life. The first, a retail store in my local mall that I started fresh out of college with no retail or business management experience, and no actual desire to be in either of those fields. My degree was in English by the way. What can I say? An opportunity presented itself and my entrepreneurial spirit (and 5-year old little girl dream) won out. Well, that lasted about 3 years until I got entirely sick of retail hours, being a babysitter for mall employees, and the overall lack of passion for what I was doing. But I walked away from that experience having learned tremendous, invaluable things about myself and business.

Enter: corporate life for a few years. Banking to be exact, which is an even more confusing decision than retail, given my immense fear of math and numbers, and the added bonus of breaking out into cold sweats when I talk about money. So, when that all fell apart around 2008 - and by that I mean banking, the economy, housing- I got let go, which I was not so secretly happy about. I opted for a new business - this time, rather than go in a weird ass direction of something I hated, I decided to get into writing. I fell really in love with working from my PJs, living on Lean Cuisine and pots of coffee, but not so much with the fact that freelance writing didn't turn out to be a creative job. It turned into more of a "you write what we want you to and in no way will it sound like or reflect you" sort of a job. #nahthanks During this time, I also sparked a strange interest in Photography. Yea, capital P.

So I vowed to never write for money again. Oh yea, I'm tough like that. But sadly, money is something you need when you are single and own a condo that you can't sell due to previously mentioned 2008 housing crisis. Sidenote: I think this stressful period is roundabout the time my health started to slowly unravel. So, back to the corporate world til I could figure another way out. A health insurance claims examiner this time. Whatever. I needed the job and the insurance was good and it served it's purpose. It's called being an adult and sucking it up.

Now we're to the current day and I'm back in my PJs, where I am a full time wedding photographer and blogger, and plan to be for the foreseeable future. How did I make that transition? Slow your roll, cupcake, that's for the next post.


1. Your Don't Give A Shit Ability. Starting your own business is all about sacrifice. Are you someone who has a tendency to spend themselves into oblivion trying to impress others? If you're creative, I'm betting no. But even if you don't suffer from The Jones' syndrome, you still need to be able to live relatively debt-free in preparation for times when you might not have income.

Example: I drive a '99 Saturn. And you know what's beautiful about it besides the fact that it's a big hunk of plastic that never rusts? It's $free.99. If I had tons of debt and bills, I probably would have lost my condo after the getting-let-go-from-the-bank crisis, but I didn't. But lots of people did. But not me. Cus I don't give a shit. Your concern for freedom, flexibility, and the ability to do something you are passionate about needs to be > your concern for material crap. That's not to say you can't have those things in the future, but not until you are well established in business. Or in my case, ever, because I don't give a shit.

2. Your Spaz Level. On a scale of 1-Spaz how much of a Type A are you? Because if you don't have drive, you're screwed and you need to harness a new dream, like yesterday. Remember all those crappy corporate jobs I just talked about? Well, if you don't, you need to start taking some Omega 3s or something because that was literally a second ago, depending on your reading speed. Well guess what? I fricken rocked those crappy jobs, so hard.

Let's take the crappiest job of Home Depot Cashier as an example. Because hi, you're talking to the fastest checker outer and Employee of the Month as per those pieces of flare on my neon orange apron. The point is— you need to possess the drive to excel at whatever you're doing.

3. Your Money Management Ability. This is a real struggle for a large majority of entrepreneurs. Money management is a very left-brained thing, and so I'm not asking you to be a rockstar but you do have to be able to get a handle on it. Being self employed means an unpredictable stream of income almost indefinitely. And on top of that, you need to be a master budgeter and learn how to spread money out over an entire year, when you might only have it coming in for 6 months.

Wedding photography is a great example because I live in the Midwest where people don't have winter weddings - nor do I want to shoot them - and essentially I don't work from Dec-March. That's a pretty sweet gig though, unless you spent all your money by November. I really can't make that mistake now that I can no longer consume ramen or Kraft products. You also have to learn things like Quickbooks and general accounting skills, but I don't want to totally send you running.

4. Your Perseverance Through Failure. You realize most business ventures fail within three years right? Ok, good. You also realize that creative people get bored easily with one thing right? Hello, Miss Three Businesses Already over here. You also realize that whether you're offering a good or service, alot of people will hate it right?

This could also piggyback on the whole not giving a shit thing. Creatives tend to be people pleasers who take it personally when their work isn't well received. You have to be really, really ok with the fact that not everyone will like your writing, or photography, or invention, or app, whatever. You are opening yourself up to scrutiny and criticism and rather than having someone else be responsible for it - it's all on you.

5. Time Management Ability. Just, it needs to be good. Because you don't have someone pointing any fingers at you or threatening write-ups or cutting bonuses if you don't perform in a timely fashion. If you're a procrastinator by nature, it's going to be a struggle.

Now. As long as you can get those things under control, it's freaking fabulous. 

Wondering who's the mysterious wordy genius behind these posts? Follow this little rabbit trail to read more About Me! The use of the term genius is open to interpretation. Like just about everything else on this site.