The Straight Dope on Being Self-Employed

Guys, I am so living the dream. 

Most days, I dress for work like I would dress for cleaning the house: leggings, band t-shirt, and a messy bun. 
There's no one to tell me I have to have that "report" ready for some pointless meeting (that should have been an email). No "case of the Mondays". No forced interaction with annoying co-workers or group work that just ends up being "me work" with a bunch of other names tacked on.

Yes. The dream. Livin' it. know....some version of it.

Truth is, self-employment comes with a lot of hidden nooks and crannies that no one really talks too much about. Because it's not cool. Or pretty. Or fun. 
I COULD take some puuurty, nicely lit image of all of my tax paperwork.
A cute desk set-up and my twee coffee cup probably looks better. Sells better.

But, I like real stuff. 
I've said that before.
So here is the STRAIGHT UP TRUTH on self-employment. 


1. It's Effing Lonely

Here's the truth....I work alone. There's no water cooler where I can shoot the shit with my fellow workers about....whatever. Sometimes I have an assistant or a second shooter, but typically its desk...the internet.....the baby. We have online groups where we trade information and stories.....but being self-employed can be really lonely. Especially if you're just starting out, trying to get things off the ground, and find yourself with a lack of support.

Which leads us to.....

2. People Usually Don't Think You Have a Real Job

My husband and I actually had a BRICK AND MORTAR STORE.....and it was still kind of like " own the place, you can just do what you want, right?".  I've had people assume I can just cancel a shoot on a dime if something pops up (Um. No.) or that I don't work at all during the week. I get "So, is this all you do?" quite often. 

It can be very hard to explain what you do to people when you own your own business. 
Remember in Father of the Bride when Brian Mackenzie said he was an "Independent Computer Consultant" and George Banks said that was code for "unemployed"? 
Yeah. It's like that.

3. Taxes Suck Monkey Butt

OMG. Just going into explaining the tax implications of self-employment.....I can't even. Suffice it to say it sucks. I'm a sole-proprietor. Which means I pay regular income taxes AND self-employment taxes. 
Some folks run an LLC or an S-Corp and that makes tax filing different, but at the end of the day the amount self-employed people pay to "the man" is just insanity. You have to pay estimated taxes throughout the year (quarterly). There's deductions there, but just to use my own situation as an example I've had to pay in every year at varying degrees. Thousands.
Kiss tax refunds goodbye. We all know that financially this is actually a GOOD thing....but it still sucks. 

4. You Work a Bazillion More Hours Than Normal

When I worked in an office I worked 7:30 to 4:30 and then I went home and generally didn't worry too much about my job until the next day. Mostly because Continuous Passive Motion machines didn't exactly whip me into an excited frenzy. But, when you create and cultivate your own business, it becomes a PART of you. My business is like my 4th child. It's with me all the time. Even if I'm just hanging out, I'm usually thinking of something business-related. I write blog posts in my head and spend showers just sitting there coming up with new ideas. It just happens naturally.
I work a lot more hours than I did before....and I work ODD hours. But somehow, when it's all yours, it's okay.
Add in there that depending on WHAT your job is, there can be a lack of "sick days" and "vacation days", especially if it's just you. And forget about sick PAY and vacation PAY or maternity PAY. 

It's not ALL doom, gloom, and sad pandas, though. Otherwise no one in their right mind would ever do it, right?

 5. The Sky's the Limit on Income

The income potential is pretty endless, depending on your industry. If you start your own thing and put your all into it, six figures CAN happen. It's very realistic. Even more, depending on how big you want to get and how good you are at what you do. 
So no slaving away at some job hoping to get recognized by the higher up's for some cost-of-living raise.

6. No Higher Ups

This is pretty much the BEST thing about being self-employed. I knew from a very early age that I was not cut out to work for a traditional "boss". I always had a bit of a problem with authority. Especially authority I deemed too stupid to be in the position they found themselves in. Which was, well.....most of them.
I remember I had a boss once at Dairy Queen that used to hole up in his office and creep the girls on his closed circuit camera.
Yeah. Bosses kind of suck.
So, being your own boss? Rad.

7. The Self-Satisfaction of Creation

Even if your business is something that may be outwardly boring as white maybe you clean pools or you've designed a new kind of flyswatter or still have the satisfaction of knowing it's YOURS. You made can market are in control of its destiny. 


I'll be honest, every year....typically around tax season or slow season....I start cursing self-employment and wonder what the hell I got myself into. But, at the end of the day, I know I am right where I need to be.

Because, for all the pitfalls....there are some really high pinnacles. I wouldn't want it any other way, I know that for sure. 

I get up in the morning....I slap on my comfies and throw the hair back and I get to work. Call it what you will: girlbossing (, don't call it that), empire-making, gettin' to's all very happy-making.

And that matters a whole heap at the end of the day. 

Amanda Reseburg