5 Awful Truths About Being Your Own Boss

Being our own boss is one of the boldest, most exhilarating, and most rewarding leaps most of us will ever take.

Seriously, it’s life changing. It’s empowering, it’s freeing, it’s fun. Every day is a new adventure.

And while there’s an ohh-ahh factor, and a general understanding of what it means to start your own business and seek financial independence, I sometimes wonder if people know what it’s really like behind closed doors.

Let’s not sugarcoat any of it. 

1. It’s lonely AF

If you find yourself googling “How to make friends” on a random Tuesday afternoon, don’t worry – you’re not alone.

Being an entrepreneur can be lonely AF. 

Why do you think there are so many masterminds and meet-ups and conferences for us? It’s the cool way of saying, “Hey, come over. My mom made brownies and I have no other friends.”

When you’re an entrepreneur, especially one who works online, it can feel like the equivalent of being outside in the rain, looking through a window and seeing everyone having fun at a party you were kinda invited to but everyone assumed you wouldn’t show.

You actually start to miss clocking in and bitching with your coworkers about life — and it all being okay because hey, you were all in this together.

2. Sometimes you miss working for someone else

This IS an awful feeling, but don’t worry, it doesn’t last long or anything… it does happen, though.

Let’s be real for a sec: Being an entrepreneur is a journey of ups and downs and sideway zigzags of despair.

When you’re starting out, you have no idea what you’re doing. When you’ve reached some level of success, you still don’t know what you’re doing.

You may even have moments when you think you’ve got it all figured out and then, boom, you get hit in the head with something you never saw coming, and you find yourself wishing you lived close enough to your parents to go spend a night on their couch and be taken care of the way you did when you were a kid.

Running your own business is WORK.

And in the darkest moments, we sometimes miss being told what to do. We miss all the answers being in a manual or a welcome packet, or a knock on the VP’s door away. An agenda set for us. A coworker to blame shit on.

It’d be nice, we think, for someone to just tell me what to do.

But, like I said, that feeling doesn’t last long.

We immediately remember how No way, I’d rather eat ramen and wear clothes designated for my fat months than go back to that hell.

3. Comparison Syndrome (read: envy) is a real thing

When we’re online, we don’t just have regular human envy — we have business envy.

Much like our 9 to 5 counterparts, we get to scroll through our newsfeeds and see pictures of Jenny who lost weight and got her teeth done, with her perfect 2 kids and millionaire hubs. Way to go, Jenny.

But in addition to the typical, “Omg why do all my high school friends look so happy?”, we also have our fellow entrepreneurs to be envious of because we’re all in the same damn Facebook groups.

**THIS probably happens in every industry.

When you’re busting your ass of to get your business into the money making machine you swore to your parents it would become, and some guy on Facebook posts about a record breaking month in sales, you kinda want to bang your head into the keyboard until some bright idea comes along for your next viral post.

Then, you spiral into the “How the hell did she DO that?”

And you start comparing your sales funnels and prices and websites…

And then it’s 2am, you haven’t peed in 4 hours, and you’ve missed Game of Thrones.

4. It’s really hard to sync your schedule with friends and lovers who work a 9 to 5

Part of this belongs in the pro section of being an entrepreneur because, hey, we get to set our own hours. Even if we’re working a 60 hour week during a product launch or something, we get to decide where those 60 hours come from. So if we need a nap on a Thursday afternoon, we take the nap.

We also get to decide when we take vacations.

Those of us who work online can pretty much work anywhere, which means, if we lighten the load before we go, we can get away with taking a few calls and answering emails on the beach.

And that’s awesome — in fact, it’s a huge reason why a lot of us do this in the first place.

But it kinda sucks when you’re dating outside of that world and your lover has 1 sick day a month and had already used his annual vacation days before he met you so, tough luck, Tulum.

Same goes with your girlfriends.

“I just can’t get off work” is about the same as us throwing rocks at a window only to hear back, “I can’t come out and play. I’m grounded.”

5. The struggle is real, but different

It’s really hard to get someone to understand your journey when they have no experience in it. And let’s be real, that’s a pretty universal thing and not exclusive to being an entrepreneur.

But it can be super hard with entrepreneurship.

It’s a long and winding road and sometimes you just want to talk to a friend or your family, or even your lover about it, but you feel like you’re shouting and no one hears you.

“Aw, you’ll be okay!”

“You’ll figure this out!”

“Maybe you should just think about a plan B?”

“Wouldn’t it be better if you went back to that nice job you had with the pretty gray office and that cute mailroom boy name Jonathan?”

Maybe this explains the rapid growth and massive sizes of Facebook groups for entrepreneurs. “Hello, can I shout in here?”

When you’re running your own show, especially when you’re first starting out, you find yourself asking “Can I actually do this?” a lot more often than the average Jane.

And you may be lucky and have friends, family, and partners say, “Of course, babe! You got this!”

Or maybe you’re not lucky and no one in your life supports your radical, alternative lifestyle of unstable income. Whatever.

The point is, there’s a reason why coaches and mentors are so important when you’re building a business.

(If you’re feeling the need for that support, by the way, email me. This is what I do.) 

Sometimes as great as their intentions are, they can only support you in a general sense — and while that’s great, we sometimes need the support of those who know exactly what we’re going through because it’s either their job to, or they’ve been through it too.

Omg this sounds horrible, why would I even want this life?

Like I said, this life ain’t for everyone… It’s challenging, it’s hard, it’s lonely, and sometimes it can be a little sad. But here’s my big, loud BUT… 

This life may not be for everyone, but if it’s for you, you know it and feel it in parts of yourself you never even knew existed.

It’s the part that fuels you to stand up for your dreams when people project their fears onto you and ask about a plan B.

It’s the part that reminds you of how grateful you are because even the hardest days don’t compare to being miserable working for someone else.

Entrepreneurship isn’t reduced to the hardships and awful truths. It’s so much bigger than that.

It’s constantly being challenged and given the opportunity for growth.

Freedom of time, money, energy, and most importantly, the self.

Creation. Creativity. Innovation.

No one to tell you what you can earn.

Being able to take a nap on a Thursday afternoon.

Waking up and doing something you love.

Being of service to others in a way that is aligned with our purpose and personal missions.

Fun. Pride. Adventure.

Communities of people who are just like us.

The lessons of independence that we get to teach our children.

And no, this isn’t for everyone. We have to be tough and resilient and be willing to do whatever it takes to live the life of our dreams. And sometimes that gets pretty hard, and it gets lonely, and it gets scary.

But damn, I love this life. This is fun, and it’s mine.

I, for one, am proud of having taken such a massive leap.

Are you?


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