The Confession of an Entrepreneur

Things I hear, a lot.

“Man, I’d love to start my own company one day.”

“You’re a lucky man, Mike!”

And probably the most common one that causes me to have to lie the most often:

“How’s life?”

These are things I hear all the time as an entrepreneur. Some people look at my company and believe it to be a successful venture. And to the outside world, it can seem that way. After all, we’re over 60 employees, have a few hundred clients and have a wall of awards to show for our efforts.

But there’s only one problem. I don’t feel successful.

In fact, most days I feel like I’m riding a bike with no brakes down a hill. I’m just swerving and trying to keep from crashing. And those 60 employees… Well, whenever I turn around on the bike, I see 60 smiling faces staring back at me with the highest expectations shining in their eyes, each riding their own brakeless bikes, each following my swerves and turns.

It’s terrifying. If I make one wrong move, if I don’t swerve fast enough, if a strong enough breeze hits me sideways, the whole group could go tumbling down the mountain.

And yet, when I’m asked, “how’s life?” I cheerily smile and tell them that things are great. Because I know that no one wants to hear me complain. After all, I’m the lucky one. I’m the one who managed to get his company off the ground and make it “successful”. I’d look like a petulant child who had been given the greatest toy, only to throw it back at his parents and saying he wanted it in a different color.

So, I smile. And I lie.

The loss of quiet.

I think the thing I miss most from the time before I started my company is the quiet. I used to enjoy sitting on a chair, laying in a hammock, or walking in the woods and just letting my mind wander. I used to think about books I wanted to write, things I wanted to make, words I wanted to speak to my wife and dozens of other fleeting thoughts that never stayed long but were always entertaining.

I used to refer to this as my quiet time. I loved it. Even though my mind was active, it wasn’t racing. It was simply wandering.

Now, however, those peaceful meandering paths my mind used to wander are gone. They’ve been replaced by a NASCAR circuit. There’s this unending roar of engines as my thoughts race around my head. The thoughts are no longer abstract and compromising, but rather they’ve become precise and pressing. What’s our revenue this month? What are sales looking like? Will this new partner deal close before the end of the quarter? What did that employee mean when they posted that meme on social media about hating their life? Am I being too hard on my team?

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Before my wife would ask me when she saw my eyes drifting off to some day dream, “what’s on your mind?” And I would smile and simply answer, “oh, nothing.”

Now she sees a look of concern on my face, and she asks me the same question. But I can never truthfully tell her, “it’s nothing.” Because it’s always something.

It’s now to the point where the quiet is almost unnerving. I try to keep my mind occupied as often as possible so the roar of the engines don’t get the chance to deafen me. And this makes me feel like I’m always “on”. I can’t take a moment off. Vacations have become a week-long effort to shut out the noise and try and relax. And most of the time, I’m unsuccessful. And so, I don’t look forward to them. They’re now just week-long periods where I’m not fully connected and not fully in charge.

And I don’t tell the people who ask me, “how’s life?” about this. I think they’d just see me complaining. They don’t really get how much I valued my quiet before everything got so noisy, so why would they understand just how much I miss it?

So, why don’t you just stop?

This is the question I’m asked by everyone that I do open up to, the people that are closest to me. They wonder why I’d continue doing something that makes me feel crazy, depressed, and anxious. And I like to tell them that while being an entrepreneur does make me feel all these things, it also brings with it positives. It energizes me, it gives me a purpose, it fulfills me.

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And this is all true. But honestly, I think I could find other things that would bring me those positive feelings. There really is only one main reason I don’t stop. I’m scared. Actually, I’m terrified.

I’m terrified that if I were to sell my company that the new management wouldn’t treat the employees the same way I do. They wouldn’t allow the special concessions I’ve made for certain team members because I know what makes that person tick and I know that they need their space to truly shine. And I’m afraid the new group wouldn’t understand that, and they’d snuff out the light that makes that team member so special.

I’m terrified that if I took my foot off the pedal for growth, that the buzz around my company would fade, the spotlight would shift, and we wouldn’t be the industry darling that we are today. And if we don’t have that buzz, would my team still have the pride they currently have? Would they still want to work for a company that wasn’t as exciting?

I’m terrified that I would never love something as much as I love running this company. I know that sounds counterintuitive after I just told you that this company makes me crazy, but it’s true. I love this company and I love being an entrepreneur. I love building something with a group of people. I love knowing that my dreams and ideas have somehow coalesced into a physical thing that is providing a living for over 60 families. And I love being able to provide a service to clients that they truly need and are grateful to receive.

And that’s my dilemma. I desperately love the thing that makes me miserable. And I think that this isn’t unique to me. I think a lot of entrepreneurs deal with this dichotomy of emotions.

Maybe it’s just me.

But hey, maybe it really is just me. After all, I’m not a sad sack that just mopes around all day. I keep my energy up, I engage with my team, I truly enjoy what I do on a daily basis. But I constantly have this monster that seems to be standing over my shoulder waiting to pounce. It’s the monster of depression. If I let my guard down for just a second, suddenly all the great things in my life are numbed and the challenges are enhanced. My leisurely bike ride with my team, along a winding river trail, suddenly pitches downward into the aforementioned steep hill.

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And I’ve sought help, both professionally, spiritually and from my mentors when it comes to this depression monster. And there are solutions to making it less powerful. For instance, meditation does help, exercise is essential for my sanity, and playing sports helps take the edge off.

I’ve even tried to dull that monster’s claws and teeth with medication. But that medicine comes with a price. While it does dull the monster’s effects, it also dulls my edge. It takes away that positive anxiety that pushes me on to the next challenge and keeps me aware of opportunities that are just around the corner. So, I avoid them. Because I’m just as afraid of losing my edge as I am of letting that monster win.

So what do I do?

This is the most honest I’ve ever been about being an entrepreneur. It’s extremely difficult for me to talk about this stuff and I’m concerned that it will make me look weak. But in truth, I’m tired of smiling and saying that everything is fine. Because, while things are good, they’re not always fine.

I don’t really know what I hope to accomplish by writing all of this, but I know that I would love to know that someone else is struggling with the same monsters, brakeless bikes, and roaring engines that I am. Because that means that someone else might have found a way to make all those things make sense.

But more than anything, I think this is just my way of blowing off some steam before the kettle explodes. It feels good to get this onto paper. It feels cathartic to let down my guard.

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