Are You Your Own Worst Boss?

Have you ever had a boss that was just a straight-up asshole?

Of course you have. Most of us that have worked in a “real-world” job has had the unfortunate experience of working for someone who just really sucked.

And while we all have horror stories to share, maybe even compete against each other with; there is something we don’t often think about.

What if you’re an even bigger asshole to yourself than your most asshole-y boss?

Cause here’s the thing.

As entrepreneurs, we’re often very hard on ourselves.

Have you ever second-guessed:

  • Your expertise?
  • Your programs?
  • Your prices?
  • Your ability to make shit happen?
  • If your business will even be successful?

I’m going to be honest. I used to do this ALL. THE. TIME.

It took forever to even price things because I was afraid it was too high and no one would buy it. Or it was too low and people would think it wasn’t valuable. I would get stuck in a conundrum of my own making.

Or I’d have this brilliant idea only to love it one week and worry over and over that it was never going to work the next week.
Can you relate?

Now, if you had worked for someone who was constantly second-guessing everything you did, telling you that you weren’t good enough, would you take it?

No! You’d likely find your best route out and quit!

So why do we do this to ourselves? Why do we beat ourselves up for not getting it right or not advancing as fast as other entrepreneurs?

That’s right. We shouldn’t.

I’m not going to tell you to never think these thoughts or to never worry about anything, cause it’s part of human nature to worry at times. But the next time you feel like you’re not good enough or think that something isn’t going to go right, catch yourself. Notice these thoughts and really evaluate them.

Are they really something you should be worrying about, or are you messing with your own mind?

Majority of the time, it’s the 2nd option.

So to help you get past the “what ifs” and the “shoulds,” here are some tips that will help you keep the right mindset and stop second-guessing yourself.

Understand your thoughts. Where are these thoughts coming from? Are they coming from a place of truth (like you really aren’t an expert or no one really is going to buy your stuff) or are they coming from a place of fear? Are these negative thoughts just a protection mechanism against the what-ifs that could happen? No judgement here if they are, I was queen of the protection mechanism, a slave to the what-ifs.

Forgive your thoughts. Like I said, it’s okay to think them. But it’s not okay to continue to think them. It’s that continuation that keeps you stagnant. Simply forgive yourself for thinking these negative thoughts, accept that they are part of life, maybe even part of the process, but move on from them.

Create new statements. Think of the opposite. And use evidence to frame these new thoughts. If you’re thinking your prices are too high, consider the fact that other entrepreneurs just like you are charging much more. Or if you think that maybe there isn’t a need for what you’re offering, I’m sure a simple Google search will prove to you that a) other people are offering similar services, and b) people are buying up those services. So of course you can too! You just need to find your edge.

You always hear horror stories about crappy bosses. Maybe you have your own horror story to share. But as entrepreneurs, we don’t really think about how hard we are on ourselves. If it were someone else treating us this way, we would never stand for that shit. So why do we put ourselves down and beat ourselves up?


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  1. Hello, Corinne!

    Excellent one! And this is what I can relate to… Not now but in near future, as I am working on getting into the own online business. 🙂

    I am already into few of the deals but I think my price is just about right or lower than the market (because I did not research about it) as the clients did not raise any question about the price, at least.

    The guys like you who is established into the market to reference through the pricing structure.

    I will try not to turn to become the worst of my own boss.

    Thank you for that!

    ~ Adeel
    Adeel Sami recently posted…Don’t Pretend to be the Perfect Blogger, Please!My Profile

  2. Hi Corinne,

    I can totally relate to this. I am my own worst boss and I do just about everything you described here, hehe. 🙂

    I have to practice changing my thoughts because I’m like you, I’m afraid to be to high or too low with my rates and worry about what others would think. Crazy right?

    Thanks for sharing these tips CK, they’re definitely going to help be more easy on myself. 🙂

    Have a great day and rest of the week!

    Cori Ramos recently posted…Easy Chicken MoleMy Profile

    • Corinne says:

      Hey Cori! Thanks for sticking around after my overhaul!

      Pricing is for sure something I’ve always struggled with. Even without the doubts and worries, I think it’s a hard game to play lol

      Thanks for reading love!


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