Why Self-Employment Isn’t for Everyone

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WhySelfEmploymentIsnt Girl, same.

Alright, so by now most of y’all know my story.

If you’re a newbie to the blog, do me a solid and swing by the welcome page so we can get acquainted.

All caught up? Wonderful.

Today I want to chat about something I feel isn’t talked about enough. You see, right now there’s this strange collective push toward ‘entrepreneurship’ aka ‘solopreneuership’ aka ‘I have an LLC after my name yo.’

It feels like everybody’s running around all:

“F the man! Be your own boss! Follow your dreams! #nodaysoff #grind #hustle #nosleep #etc”

In fact, every time I click on a YouTube video, an ad starring a random unshaven millennial-aged dude pops up. Millennial Dude is usually standing in front of a small mansion or casually exiting a supercar or helicopter, or velociraptor, or some other expensive mode of transportation.

Anyway, Millennial Dude then proceeds to tell me that in a year’s time he went from licking the lint off of Goodwill sweaters to high-fiving Lebron court side. How you ask?

Easy. He became an entrepreneur.


AND if you purchase his course/eBook/membership, he’ll teach you everything you need to know to emulate his success.

Now far be it from me to take anything away from Millennial Dude’s success. And who knows…maybe what worked for him will work for you.

It just seems that lately, entrepreneurship has become this woke as hell, super trendy thing to do.

There’s also this implied assumption that self-employment is right for everyone. After all, who wouldn’t be happier making their own schedule, coming and going as they pleased and being the flipping captain of their own ship?

Sign me up! Right?


There you go. Brought y’all some umbrellas. You know, because I’m about to rain on your entrepreneurship parade.

Reasons Why Self-Employment Might Not Be Right For You

1. You Get Lonely.

Yes, I know everyone gets lonely from time to time. But if you’re the type of person who can’t go more than a couple of days without human contact, you may want to rethink working for yourself.

WhySelfEmploymentIsnt3 Actual shot of Janet Jackson being “too lonely to let just anybody hold her” circa 1998

Unless you have a business partner, expect to spend the majority of your time all by your lonesome (multiply this by a million if you’re a writer, yes a million).

Building a business is a lot of f’ing work. It’s long days spent hunched over a keyboard or standing ergonomically (I’m almost certain I used this word wrong) at a standing desk.

There are no high fives and pats on the back for a job well done. There are no surprise pizza parties because you overshot your quota for the month. And there is no tax refund.

But you know what there is?


As is, “God, you know I’m poor as hell and can’t afford a CPA. You also know I just spent 4 hours in a video chat with Trina, a ‘turbo tax expert’ and I’m fairly certain I’m going to get audited. I mean, I would audit me. Anyway God, I think this might be the year you should get rid of the IRS.”


Ahem, anyway…if you thrive in a work environment full of excitement, water cooler talk, and you know, human beings, you may want to reconsider working for yourself.

2. Do You Even ‘Kon Marie?

Yes, ‘Kon Marie is now a verb. No, seriously. Google it. Then read The Life-Changing Magic of Tidying Up because it is legitimately LIFE CHANGING. Y’all my house has been tidy for over TWO YEARS. She’s magic.

Okay, let’s get controversial here for a minute because I know some of y’all can’t find your desks under that mountain of clutter you “claim” is organized. It’s not.

There is no such thing as organized chaos.

There is organization. There is chaos. Never shall the twain meet.

And that concludes my TED Talk.

I kid, but really. Organization is so important when you’re self-employed.

So ask yourself:

Do you have scheduled work days and off days?

Do you keep your business expenses separate from your personal expenses?

Do you have a mailing address for your business? A business phone number?

How do you organize your projects? Spreadsheets? Google Docs?

I could go on and on, but you get the point. If your -ish isn’t organized and you refuse the help of the all-powerful Marie Kondo…business ownership might not be your thing.

3. You’re This Guy


Don’t get me wrong, I LOVE Ron Swanson as much as the next ornery gal, but Ron isn’t exactly the most…flexible person in the world.

Exhibit A
“Dear frozen yogurt, you are the celery of desserts. Be ice cream, or be nothing.”

Exhibit B
“Crying: Acceptable at funerals and the Grand Canyon.”

Exhibit C
“There are three acceptable haircuts: high and tight, crew cut, buzz cut.”

Lolz. But seriously.

Flexibility is a must in the self-employment world. Things will not go according to plan and if you’re the type of person that can’t roll with the punches, this might not be the right gig for you.

You probably like that steady, trusty paycheck, don’t you? The one that’s always the same amount every month?

Ha! Some months I feast like a king and other months I like to give my college years a shout out by eating Ramen noodles exclusively.

And what about the awesome regularity of going to work, doing the one job you were hired for, then going home and watching Hulu? (sidenote: I feel like Hulu doesn’t get enough love as a streaming service reference, so there ya go.)

As an entrepreneur, you’re going to have to wear a minimum of five different hats. You see, I foolishly thought the most important task of a self-published writer was writing.


And yes writing is important, but just as important are marketing, editing, graphic design, blogging, social media, author brand, release schedule, responding to email/comments, etc.

I can’t just be a writer. I mean, I could but I probably wouldn’t sell enough books to make a living. (And yes, I know I can’t live on $500/mo. Hush you.)

If the idea of not knowing how much you’re going to get paid on the regular gives you the hives and shoving your author brand marketing strategy down the Internet’s throat seems tasteless to you…you might want to hit up Linked In refresh the old resume.

4. You’ve Felt Personally Victimized by Regina George.


Here are some cold, hard truths…

People are mean.

People on the Internet may be the meanest of all.

Rejection hurts. A lot.

Some people won’t like you. Or what you do. Or how you do it. Ever.

As an entrepreneur, you are going to have to grow some thicccccck skin (lolz, I almost left the ‘k’ off of thick because I’m a child)

It sucks, but it’s a fact of life.

You are going to face rejection (probably a lot) and it’s easy to take it personally, after all, you’ve poured your blood, sweat, and tears into [insert the name of your business] and you want everyone else to love [insert the name of your business] as much as you do.

But they won’t. And that’s okay. You must go into this with the understanding that some people will love your -ish, and some people will flat-out hate your -ish. And those lovely folks will not be shy about letting you know how much they think you suck.

So if after someone calls you a mean name in the comments section of your local news station app, this is you:


You might want to rethink your dive into the world of entrepreneurship.

5. And finally, Can You Kick Your Own Butt?


I touched on self-discipline in an older post, but it bears repeating.

Although becoming an entrepreneur might be your dream, you’re not always going to feel like sitting your butt in your chair and doing your work.

In fact, there will be more days than not, when you’d rather do anything other than your work. And guess what? Since you’re your own boss, you get to make that decision.

It’ll probably go something like this:

“Hey, you want to work today?”

“Mmm, not really.”

“Oh, uh okay. How about going for a run instead?”


“Hmm..do you want to get Cold Stone and watch the entire first season of True Detective?”

“Now that’s the shit I like!”

That may or may not have been a legitimate conversation I had with myself last week.

I cannot reiterate this enough. If you want to be a successful entrepreneur, you must stay on top of your -ish. Consistency is a necessity.

And yes, it’s okay to have a lazy day once in a blue moon. But once in a blue moon is not every week.

Look, I know that a lot of this sucks. It’s gonna. But it’s also gonna be worth it when all your hard work pays off and you too will have your own YouTube ad where you’re riding a velociraptor.

So basically, if you’re not that great at making yourself do stuff you don’t want to do, maybe join the army first. Then start your own business.

In Conclusion

I think the key to this whole entrepreneurship kick that everyone seems to be on at the moment, is to treat yo’self know yourself and to really be honest about why you want to be an entrepreneur.

Is it because you hate your job/boss/commute?

Or because, based on hundreds of YouTube ads, it’s clearly the path to riches, and Bentleys and mansions?

Or maybe it’s because all the cool kids are doing it?

To be blunt, those are all terrible reasons and while I can’t give you a compelling reason to work for yourself (only you can do that), I can speak from the experience that I’m earning along this journey.

Is it easy?

Heck no.

Is it worth it?


…I’ll let you know in about five years.

evelyn dar

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