Being Your Own Boss: Expectation vs Reality

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*This dude clearly works for himself. You can tell by his entrepreneurial laugh/smile.

*And the entrepreneurial arrow coming out of his shoulder.

Alright, close your eyes…

  • Imagine a world where you can roll out of bed whenever you want.
  • A world where your daily commute is the length of your hallway.
  • An hour for lunch? Better make that three.
  • Forget to shower? No worries. Your co-workers are a 4-year-old Shepard mix and a 5-year-old…cat. Um, just a regular cat, I guess. Domestic maybe?

Anyway, you have now stepped into the most alluring and desirous of all occupations.

You Are Self-Employed!


You told ‘the man’ to take that thankless job of yours and stick it where the sun don’t shine.

Or maybe you quietly gave two weeks notice and refrained from calling your former boss an ‘asshat’ like the adult you are.

Either way, I’m proud of you. You’ve taken the first step toward making your dreams come true.

Everything from here on out is a cake walk.




“I’m going to wake up every day with a huge grin on my face and backflip out of bed because I’m finally doing what I love for a living and it’s so awesome! #blessed #entrepreneur #onmygrind”


Seems Legit, right?
And there will definitely be days when you’re just rarin’ to go. You can’t believe the blessing that life/the universe/Alanis Morisette has bestowed upon you.

You’re burning through your gratitude journal and can’t keep that ‘shit-eating’ grin off your face whenever you run into an acquaintance that still works for ‘the man’


Then one day, seemingly out of the blue, you’ll wake up feeling like this poor sap.

What happened to all your passion, drive and optimism??

Welcome to the Club!


No matter how awesome or terrible a thing is, we humans will eventually adapt and our happiness (or sadness) will return to our usual state of ‘meh.’

Which is awesome when it comes to cutting off your pinky but less awesome when it comes to quitting your job to pursue your passion. 

Call me crazy, sexy and cool but I honestly wasn’t ready to adapt to my super dope entrepreneurial lifestyle.

Sure, I knew every day wasn’t going to be a cakewalk, but I was hoping for at least a brownie walk with a few sprinkles tossed in.

The Takeaway
I still wake up grateful to do what I love for a living, but I’ve realized that my profession doesn’t have much impact on my overall happiness.

Basically, if you were a miserable nine to fiver, you’re probably going to be a miserable entrepreneur.

And that’s okay.
Although you might want to try meditating or something. Just sayin.

“My social life is going to be so lit now that I’m making my own schedule!
I’ll see my friends all the time and they’ll totally treat me the same.”


Okay, I’m cautiously with you.
You probably will have tons of free time…at first. But if you’re serious about saying goodbye to your 9-5 forever, and not just for a few months, you’re going to have to introduce yourself to a stubborn little fellow called self-discipline.


“If people knew how hard I worked to get my mastery, it wouldn’t seem so wonderful at all.” – Michelangelo

And that’s the thing.

No matter how much you love what you do, it takes a tremendous amount of self-discipline to make a schedule and force yourself to stick to it NO MATTER WHAT.

“I know I’m supposed to be working but I really should run to the bank and while I’m out, I’ll stop by the store and pick up some bananas.”


“I was totally ready to seize the day this morning. I meditated, drank a cup of green tea and even took a jog. Then I read a mean one-star review on Amazon and now I want to curl up in a ball and eat cake.”


“I think I have the flu.”


Okay, maybe the last one was legitimate. But you get the point. It’s incredibly easy to let yourself off the hook, just this one time – and it’s always just this one time, right?


As your own boss, you’re responsible to…absolutely no one. If you leave work early to catch a movie, your pay won’t be docked, there won’t be a write up waiting on your desk the next day, and you won’t get fired.

But you probably won’t be self-employed for very long.

Keep that in mind when telling your friends how much more free time you’ll have now.

If you can nail down the self-discipline thing (pray for me, I’m still working on it), you’ll probably see them less than you ever did before.

Which is fine, because they’re going to start resenting the hell out of you anyway.

Say whaaat?? Not my friends
Yes, your friends. Your best friends. Your acquaintances. Your ex-coworkers and your cousin Ray J.

But why? I thought they loved me.

They do. And deep, deeep, deeeeep down they want you to succeed. But you have to understand, you are doing something that the VAST majority of people never even attempt.

There’s a reason why entrepreneurs only make up 6.02% of the US population!


Everyone has dreams. And by that I mean everyone. They might not talk about them or acknowledge them, but everyone dreams of something better for themselves.

Dreamers are a dime a dozen but doers-the ridiculously, crazy among us who know that if we can dream it, we can achieve it-we’re a little rarer.

And a little more dangerous.


Because we remind the dreamers that it can be done.

As a teenager, your cousin Ray J wanted to be an actor but somewhere along the way, he convinced himself that acting wasn’t a “sensible profession.” The odds of failure were high, he didn’t have any connections in the biz, and Los Angeles might as well have been Siberia.

Instead, he settled into a sensible, well-paying job that came with two weeks of vacation a year, and robust health insurance.

(Sidenote: I’m poor and have no insurance, so trust me I’m not looking down on Ray J)

Your cousin’s not miserable but he’s not doing backflips while examining spreadsheets either. He’s content…most of the time.

But then YOU come along with your two successful self-published novels and your one-hundred twitter followers #getmoney

YOU are walking, breathing, irrefutable proof that following your passion can work. Evidence that you don’t have to settle for your life but that you can create it.

And how does that make Ray J feel?

Kinda like this dude I imagine.

And then the comments start…

“So, when you going to get a real job?”

“I hear the State’s still hiring. You’ve heard about their benefits right?”

“Oh, you’re still doing that little writing thing?”

I promise you, the people you love aren’t trying to tear you down or piss you off. They’re probably so far removed for their own dreams and desires they’re not even aware they’re doing it.

Over the past year, I’ve learned to take comments like those with a grain of salt and laugh them off.

Although secretly I imagine how delicious it’ll be when one of my novels gets made into a feature film or a Netflix series.

“Will you still refer to it as “that little writing thing” now, Aunt Nina?”

Whoa, sorry got off track there. I’m good. I’m good.

In Conclusion

I’ve really only scratched the surface of what I expected vs the reality of being my own boss this past year. Mostly because I’m ridiculously long-winded. My apologies.

Just know that while I expected it to be hard, I didn’t expect it to be the hardest thing I’d ever done in my life.

To my entrepreneurs, side hustlers and freelancers…what’s the one thing you didn’t expect in your self-employment journey?

To my 9-5ers, what are you most looking forward to when you take the leap? What are you least looking forward to?

Oh, and let me know in the comments if you want me to write a part 2 to this post because there’s definitely more. 

evelyn dar




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