The Beautiful Psychological Nightmare of Entrepreneurship

Updated: Jul 19, 2019

Building your own business is tough. So is coming to terms with your new psychologically induced facial tics. Whatever has called us to leave the comfort of a steady income, a reasonably balanced budget, and security for our families, I think it’s safe to say that it knew we were never going to be the guy for an easy kind of existence.

That’s not to say there’s anything wrong with normalcy. We ask ourselves the same question when we leap from a different airplane: Am I the guy for this kind of existence? Who in the hell is going to give me their money or allow me to steer this ship (particularly with a semi-permanent eye-twitch)?

It’s probably the media’s fault

Being the boss ain't easy. Nor is free-falling into the unknown. We can partially blame the media for overhyping the lifestyles of the successful few who actually make it to the top, but we’re not particularly innocent. We do nothing to dispel the notion that owning your own business is anything but a beautiful way to live.

Even when we’re moments away from checking into a psychiatric ward.

Entrepreneurship and the media
Holy FAKE NEWS on fire!

It’s true that most successful business owners don’t own their own helicopters and squirrel around with Kim and Kanye. That’s not to say that some of us don’t find success in our own ways – but sipping champagne in Waterford crystal flown in from our wineries in France at lunch time, is by no means ‘the norm.’ And whatever success we encounter, it usually comes at a price.

Were we raised by wolves?

Well, we have family and friends just like yours, thanks for asking. They say things like: “You have to pay how much for your own insurance?!” and “What’s going to happen if you don’t get the next deal?” and “Why can’t you JUST BE NORMAL, LIKE EVERYBODY ELSE?!” Whatever that means (coming from wolves).

We’re often surrounded by like-minded (crazy) people who have equally mastered the ‘fake it ‘til you make it’ face, but the majority of the time, being open and honest about the state of our businesses, and how it affects our lives, can be a somewhat intimidating topic of conversation.

Wolf pack
Me and the guys last Sunday

We say things like “Business is great!” when we’re one dicey decision away from losing the roof over our heads. But what else are we going to say? We need to keep our people excited, our friends and family optimistic, and our investors from losing confidence.

We’ll let you pick our scabs when we secure our next round of funding.

This can sometimes give us a ‘lone-wolf’ status. It’s not a complaint, but our difficult choices sometimes require carrying a heavy load in complete silence. Remembering to surround ourselves with other wolf-like entrepreneurs or mentors, with similar challenges, is a great survival strategy. Sometimes lone-wolves need to be reminded they need a pack to survive.

Everything and everyone becomes our beeswax

Most entrepreneurs I’ve encountered are infinitely passionate about their businesses and ‘The Weekend’ is just some Canadian dude who thinks he knows music. Those days between Friday and Monday disappear in a haze of market analysis, budget refinement, and getting familiar with ourselves in front of a mirror as we practice our next pitch to investors.

People count on us for their livelihoods. Our families encouraged us because they at least believed we could sell a convincing story. But the thing is, we don’t just fail when our story fails. We fail everyone who believes in us, gave us their money, and quit their high-paying corporate jobs. Their lives become our business too.

Working nine to five – that’s how people make a livin’?

There isn’t an entrepreneur I know who doesn’t work less than 60-70 hours a week. We’ve been around since 2016 and we have yet to enjoy a work-free vacation. Our endeavors don’t appeal to the apathetic (or the mathematically inclined) if 90 percent of businesses fail within the first five years. No one starts a business to go bankrupt.

That’s not to say that being a business owner doesn’t have its benefits. We don’t have a sleazy boss with an IQ less than our parakeet’s trying to peck at our private parts all day. Nor do we have a human resources professional threatening our suspension, for failing to watch the latest ‘Try Not to Peck at Anyone’s Private Parts During Work Hours’ compliance video.

I couldn't find a parakeet

Our nerves might be shot, our bank accounts frozen, but our souls remain intact.

For the most part, we work with people as sick and tired of the status quo as we are. Our colleagues aren’t afraid to work hard and sometimes they’re in it “just for the experience.” We’re inspired, we’re hopeful, and we like to tell ourselves “Win or lose, we did it our way.”

Then again, maybe we’re all delusional.

Shit happens and it sucks

None of us believes failure is an option, but sometimes it’s out of our control. Potential investors can be fickle and occasionally unreasonable. They are human, after all. Sometimes we have to bite the ol’ proverbial bullet and not accept the very thing that could potentially save our business. Sometimes honor isn’t for sale.

We have to make big decisions like forgoing smart media and content strategies to pay for that one developer who will get our app idea to market in half the time. There certainly aren’t enough hours in the day to go-to-market with a party of two and limited funding. But hey, since we're here...

Sometimes we have to let people go. The same people who believed our idea was good enough to leave their high-paying jobs with great benefits to work for our cowgirl outfits. We lose the people closest to us and sleep becomes fleeting.

Whatcha gonna do?

Feelings of isolation, fear of failure, and the simple physical deficits we endure when starting a business can lead to significant psychological pressures. Nobody starts a business with the intention of failing. And none of us thinks we’ll be in the 90 percent.

It’s tough to hide the anxiety and depression that often dribbles into our private lives. We try our best to silence the nagging ‘What ifs?’ ‘Did I do enough?’ ‘Will we make it?’ But that ticker tape is always running in the background. Our families start to hear it too.

Why do we do it?

That's what happy people look like inside my head

One word: Freedom

Sure, we all want to make money and sip champagne from our own wineries in France – preferably in Waterford crystal, and at a quarter to noon. It sure as hell beats running errands and shoving our faces full of fast food, in whatever snub of a time allowed by a diseased company policy. Argue that one, my friends.

(Speaking of diseased company policies, if you have a few more minutes, check out Author & CEO Liz Ryan’s Ten Stupid Rules that Drive Great Employees Away. And then eliminate them from your business plans)

But most of us won’t enjoy such luxuries. There are no guarantees in life, and the very nature of existence is change.

Yeah it worth it?

Our sleep? Our mental health? Our time, money, and relationships? You may be surprised at my answer, but…


Whether it’s easy for anyone to be employed, remains a debate. I can only speak for myself and those few entrepreneurs I’ve been lucky enough to know, when I say that it is far easier to live, when you know the next paycheck is coming. However difficult it’s ever been for us to follow company policy, it’s nowhere near as difficult as deciding between your sister in-law’s salary and keeping the lights on.

Those days we wish we were different people, entirely.

It was easier to get up every morning and have the same routine with little to no deviation. I used to find comfort in knowing I could plan a long weekend to see my parents, or take a three-week trip to Europe to see my husband’s – it was a relatively uncomplicated and substantially more predictable life.

The problem is, some of us are just…complicated.

So…Are You the Guy?

You’re damn right you are.

Why you're the boss
Not everyone hops on the tight rope over a cold ass river

You’ve been willing to risk everything. Your reputation. Your money. Your family’s comfort. Your own mental stability. The possibility of dying alone. You’ve bet it all.

On the one thing you can always count on:


I’m not suggesting everyone flee their workplace and throw everything they own atop the burning embers of their own hustle. We’re all going to have wonderful lives (if that’s how it works) whether we hustle for ourselves, or we hustle for someone else. It doesn’t really matter.

What I am suggesting, is that until you’re willing to stoke those embers (with possibly everything you own) – and walk with the soles of your feet on fire just to see if you could get to the other side – you probably won't appreciate the profound beauty and simplicity in the fact that you’ve always been the guy.

Keep going.

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