Ash Ambirge
Ash Ambirge
The Middle Finger Project

Entrepreneurs: When Your Life Is Fantastic And Fucked Up, All At Once

Entrepreneurs - we really are a bunch of sickos. Volunteering to walk the plank without knowing if we can swim…just to find out if we can or not.

Entrepreneurs: When Your Life Is Fantastic And Fucked Up, All At Once Ash Ambirge - Lioness MagazineYou know when you have a problem?

When you own more EIN numbers than you do pots and pans. You know? It’s like—what are you doing with your life? Here you are, cookin’ up business plans, when you know what you really ought to be cooking? LUNCH. Because let’s face it: Just who is Paula Dean and what has she put in my meatball?

Entrepreneurs are funny. You know how you know when you’re a real entrepreneur? When you actually like the torture.

You sicko! We really are a bunch of sickos. We’re like a massive group of people actually volunteering to walk the plank without knowing if we can swim…just to find out if we can or not. Doesn’t matter that there are sharks. Doesn’t matter that there are riptides. Because somehow, some way, we know we’ll find the buried treasure eventually…and way before those assholes sunning themselves on the poop deck. Poop deck. Always did want to use that in a blog post.

Bottom line: It’s a real risk.

You could have a far better lifestyle than all of your friends combined, or, you could end up having a nervous breakdown. Jumping out a window. Never being able to enjoy the month of April ever again. Everybody’s running around on Facebook bragging about their tax refunds, and you know what you’re doing? You’re squeezing your eyebrows together frowning at the screen. That’s exactly what you’re doing. You have a big stupid look on your face because you’re the only kid on the playground who isn’t getting any money back, because what person overpays their quarterly tax estimates? Nobody. You’re rounding down on those numbers, man. Nobody’s rounding up. If you’re rounding up, we should talk. You’re probably one of those mythical good people. Or something.

Let me tell you—in ten years in business for myself, I’ve had my fair share of stuff you don’t think is going to happen to you until it does. I’ve made stuff, sold stuff, loved stuff, lost stuff, gone to court about stuff, stayed up for years worrying about stuff, didn’t worry about stuff, tried, erred, tried again, and kept coming back to the plank for more. I’ve aced stuff, bombed stuff, celebrated stuff and cried over stuff—sometimes all in one day. I’ve started stuff I couldn’t finish, finished stuff I never started, put my foot down when I needed to, and put my foot in my mouth when I didn’t. I’ve learned stuff, witnessed stuff, seen stuff and watched stuff. I’ve worked with people who had stuff, people who never had stuff, people who just want your stuff, and people who want other stuff. I’ve been righted, wronged, triumphed, torn down, helped up, hung up, stood up and worked over. I’ve succeeded under extraordinary circumstances, failed under ordinary ones, made hard decisions other people would find easy, and made easy decisions other people would find absolutely impossible.

As it were, I’ve got some serious dirt underneath my business fingernails.

The kind of gritty dirt that only comes from playing in the garden. Or a junk yard. Pick your own ending on that one.

But you know what’s funny? I choose to do it all over again, every single day. Just like I have for years, as I sit here typing to you from a hotel room, traveling around the world loving my life and simultaneously despising it, because that’s the truth about life as an entrepreneur. There’s never a good day or a bad day, because every day is both. You’re always winning, and you’re always losing, because that is the nature of risk, and risk is the nature of business. And now?

Business is the nature of you.

It’s why I’m excited to start yet another company this year. It’s why I’m taking other entrepreneurs to Italy this fall. It’s why I just opened registration to The Six Appeal Process this morning, my best-selling writing class for selling more with words, to have an opportunity to work with people from around the world. It’s why I volunteer my time helping entrepreneurs in Central America. It’s why I say yes to 5 o’clock in the morning even when I don’t want, say no to things I do want, and go after the things we all want—rain or shine or smoke or fog or tears or torture…and then some.

And, believe it or not, it’s why you’re reading this right now, too.

Because you’re one of us now.

And every single day, from now until the day you die, you’ll concurrently have a better experience on earth than everyone else…and a worse one. Better because you’ll live in ways no one else does…and worse, because you’ll live in ways no one else does.

You’ll be faced with some of the weirdest, most fucked up predicaments of your life—and yet, there will be no one there to tell you how to fix it. You’ll have to go into battle not only with the world, but with yourself…every single hour of every single day, without any promise that you’ll actually win. You’ll have to have nerves of steel, even when you feel like a little flower, and you’ll have to have the disposition of a little flower, even when you feel unnerved as steel.

And, most of all, you’ll have to figure out who you actually are, all over again, every time you wake up in the morning, because being in business changes you.

Maybe that’s the hardest piece of all. It’s like having to learn everything all over again—and again, and again, and again.

Nothing is assumed. Nothing is automatic. Nothing is on auto-pilot.

Rather, everything is what you decide it’s going to be. And, that’s a lot of pressure for a person. To have to decide all the time. Because now, no one’s there to tell little Jimmy how to behave—he has to figure it out himself.

The good news? It’s in that process where he’ll find himself.

Maybe that’s why walking the plank is so attractive. Not because of the risk involved with doing it, but the risk involved with not.

Because either way you spin it, you’re still going to be out in the middle of the ocean left to fend for yourself.

I guess the only thing left to decide?

Is whether you’ll take it as an opportunity—

—or a liability.

As usual, the choice is yours.

About the author

Ash Ambirge

Ash Ambirge is the owner of a no-bullshit community & mentor for business owners who roll their eyes at everyone’s “newsletter” and want to learn fresh, original ways to hijack the sea of sameness. (Located 20º north of the Strait of Eyeglaze.) She helps the lost, the confused, and the marketing anxious learn how to take their business & gracefully chainsaw through cookie cutter tactics that don’t even work (nobody wants your free goodies, or your “solutions”), and use the unexpected as a lethal sales weapon that no competitor can touch. But most of all? We help you screw “business as usual” and have fun doing business. Because if you’re not having fun, then you might as well be in jail, and jail is bad.


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  • This blog post is PHENOMENAL and so inspiring! I am in the midst of creating my start-up and hoping to launch within the next month (online boutique) and although I should be scared, confused and lost – I feel excited. Invigorated. Motivated. Maybe it’s because I’m not “all in” and will work my cushy marketing job at a non-profit while I build my business, but I think it’s more because I have known that entrepreneurship is what I’ve wanted to do since I was little (think, 8 years old). It’s dumb that it’s taken me until my early 30’s to finally start following this path, but once I do – I won’t look back.

  • Truer words never written. These are the words of a businesswoman, an individual who’s walked the talk.

    Take heart though, Ash: we’re the stuff America was built on!

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