I Was Forced to Admit the Unglamorous Truth About Entrepreneurship

And it wasn’t very difficult.

“What are the unglamorous parts of entrepreneurship?”

That’s an actual question I was asked by one of my students. He came to my office hours looking for career advice, and the way he asked his question surprised me. It was as though he’d only ever heard great things about being an entrepreneur, and he was suspicious. I could almost hear him wondering: How could any job be so incredible? Surely there has to be something negative. Will this guy please let me in on all the dirty little secrets so I know what I’m really getting into if I launch a startup?

His question — and the underlying concerns they implied — perfectly illustrate the fundamental misperception between what people think entrepreneurship is like and what it’s actually like.

Before I spend the remainder of this article lamenting the challenges of #startuplife, I should clarify that being an entrepreneur — especially the type that pursues the kind of “professional entrepreneurship” I discuss in my articles — is an enormous privilege. I don’t mean the work is always easy or fun or glamorous, and I don’t mean everything in a professional entrepreneur’s life is perfect. I just mean professional entrepreneurs are rarely dealing with immense tragedy or hardship. For example, they’re not likely to be battling stage-four cancer simultaneously with launching startups; they’re not cowering in basements because air raid sirens are going off all around them; they have electricity and Internet, a decent phone, a fancy computer, and so on.

So… yes… professional entrepreneurs like me (and, quite possibly, you) are incredibly privileged. But that doesn’t make the work glamorous in the way my student was imagining it.

The vast majority of entrepreneurship consists of exhausting, frustrating, time-consuming, expensive, and occasionally soul-crushing work. If all that doesn’t sound bad enough on its own, in addition to all the hard work and crushed souls, entrepreneurs rarely achieve their intended outcomes, which I imagine is about as pleasant as jumping into the ocean with a thousand paper cuts.

Despite the struggles and challenges of entrepreneurship, I also felt like I knew exactly why my student had asked his question. From an outsider’s perspective, being an entrepreneur can, indeed, look quite glamorous. After all, plenty of the world’s richest and most famous people are entrepreneurs. What could be so terrible?

My student’s naivety caused me to laugh longer and louder than what was professionally appropriate. I caught my breath as I apologized for laughing, and I eventually managed to choke out a response to his question. “The unglamorous parts of entrepreneurship?” I guffawed, incredulously. “What do you think are the glamorous parts?”

“Being an entrepreneur seems amazing,” my student replied. “You get to be the boss of your company and manage lots of people. You get to raise millions of dollars. You get to be the featured speaker at all sorts of events. Every day people rely on your product to improve their lives. What could be bad about any of that?”

I shook my head and sighed. He wasn’t necessarily wrong. In fact, I remember being excited imagining the same kinds of opportunities for myself when I first envisioned being a successful entrepreneur. However, what I didn’t understand was that all those things that seem prestigious and glamorous are also core parts of an entrepreneur’s job. And, like most jobs, they’re hard work. I don’t mean they can’t be enjoyable, but enjoyable isn’t the same as glamorous.

“Being the boss and managing people can be cool,” I conceded. “But being the boss also means having to discipline people and sometimes even fire them. It means you have to manage interpersonal conflict and infighting. Those are things that’ll create enormous amounts of stress, and, when you genuinely care about your employees — like most entrepreneurs do — they’re the kinds of things that’ll keep you up at night and even give you nightmares.”

“Oh yeah,” said my student. “I hadn’t thought about that.”

“The same kinds of things are true with raising millions of dollars in funding,” I continued. “Raising venture capital requires an enormous amount of work. Plus, when you succeed, it’s not like you’ll suddenly have millions of dollars in your bank account you can use to send yourself on vacation to Fiji. The money you get from venture capitalists represents an enormous responsibility you’ve been entrusted with. Remember, lots of VC money comes from things like pension funds and retirement funds. Are you prepared to be responsible for the personal savings and financial wellbeing of thousands of complete strangers? Even worse, you’re supposed to use their retirement money to accomplish a task that’s nearly impossible. In other words, If you fail — which, by the way, is the most likely outcome — you’re not just losing a VC’s money. You’re losing money from hardworking people who are, in part, depending on you for their long term wellbeing. What’s so glamorous about that?”

“VC money comes from pension funds?” he repeated. “I didn’t realize that.”

“Not all of it,” I replied. “But some of it does. And even if it doesn’t, you’re still taking other people’s money and they’re trusting you to accomplish a job that’s nearly impossible. It’s exciting and thrilling, but it’s also stressful and terrifying.”

“When you put it like that,” he replied, “I guess it’s not as glamorous as I thought.”

“No, it’s not,” I agreed. “Even the speaking engagements you mentioned aren’t as great as they seem. Preparing for a speaking event can take tons of work, and the events themselves can create lots of scrutiny. Similarly, getting your product in people’s hands is thrilling, but it’s also scary as hell. What if your product doesn’t work like people expect and they’re mad about losing their money? What if it injures someone? What if, heaven forbid, your product kills someone? In other words, being an entrepreneur creates lots more responsibility than what you’re imagining, and nothing is as carefree as it seems”

“No, I guess not,” he conceded. “Now you’ve got me thinking maybe I don’t want to be an entrepreneur after all.”

“I’m not trying to scare you away from startups,” I clarified. “I love being an entrepreneur. I enjoy every second. Even the exhausting, stressful, terrifying seconds. I’m just making sure you understand what you’re getting yourself into. The outside world loves to glamorize entrepreneurship, and that’s great because it helps attract brilliant young people into the startup ecosystem — people like you… people who have the intelligence and drive and passion to change the world. But changing the world isn’t glamorous. Changing the world is hard work. Are you ready to do it?”