Being a Lousy Employee Made Me a Successful Entrepreneur
Whenever a young person asks me how they can make a career out of being an entrepreneur, I try really hard not to disillusion them. But I feel like it’s my duty to warn them that being an entrepreneur is a terrible career choice.
Don’t get me wrong: There is nothing I would rather do with my life than start businesses, grow companies, and help and advise other entrepreneurs to build their own businesses. Being an entrepreneur makes for an awesome life — just not an awesome career.
I’ve faced a ton of challenges founding, leading, and advising companies for over 20 years, but the toughest among them is the fact that I’m this deep into the startup game still haven’t found what I’m looking for. The biggest hurdle in my entrepreneurial career is that I still don’t feel like I have a career at all.
Is this you too? Are you fighting an uphill battle explaining to friends and strangers what you do, struggling with problems and decisions no one else worries about, and maybe getting a little jealous when corporate perks are thrown at your peers?
If so, you’re not alone. Let me tell you how I discovered that walking your own path, especially when you have to create that path while you walk it, requires redefining your goals, but can ultimately wind up being the best choice you ever make.
I was that kid with the briefcase
I was not a child entrepreneur. I never so much as opened a lazy summertime lemonade stand.
When I was growing up, if you had told me that I would spend my life working for a Fortune 500 company for 40 years — with bosses to please and reports to write and big accounts to win and promotions to chase — I would have happily signed up on the spot.
I’m a second-generation American and the son of a music teacher and a nurse. My version of the American dream was filled with sharp-looking suits, palatial boardrooms, flights to big meetings, and all those accoutrements that seemed like business in the movies. I wanted all that.
Eleven months into my childhood dream job, I made the decision to quit.
Then when I finally got it, I hated almost every minute of it. I felt like half of my day was wasted completing self-justifying tasks — paperwork for paperwork’s sake, meetings to talk about meetings, hour-long debates on a single word in documentation for some process that I could actually explain in five minutes.
And because I was 23 years old and therefore felt like I already knew everything there was to learn in the universe, my response to this corporate malaise was to become a shitty employee. I started to question everything, started asking “why are we doing this?” too many times and to the wrong people, started to rebel.
Eleven months into my childhood dream job, I made the decision to quit. They would have probably fired me if I hadn’t. It took me two more months to find a job I thought I wouldn’t hate — which turned out to be doing something for which I had no formal training at a three-person startup no one had ever heard of.
I was immediately hooked.
The best startup career advice I ever got
Not long after, I got a chance to see Bob Young, former co-founder and CEO of the software company Red Hat, speak at a local event.
He opened his remarks with a lighthearted anecdote about how when people asked why he chose to become an entrepreneur, he said it was because when he discovered an idea he was truly passionate about, he would go all-in on it — 24 hours a day, 7 days a week. Then, once he learned about 60% of everything there was to know about this new obsession, he got bored and didn’t want anything more to do with it. After realizing he’d never make a good corporate employee because of this trait — corporate bosses would not take kindly to this kind of behavior, he reckoned — he left with the prospect of becoming an entrepreneur instead.
I immediately thought to myself — “Holy shit. That’s me.”
I had a friend who ran a local scrappy startup print magazine, and I convinced him to let me “interview” Bob for an article. I spent an hour with Bob asking every question I could about entrepreneurship and career and how those two things never really intersected. By the time our hour was up, I realized I’d have to redefine everything I had held true about work and career and climbing the professional ladder.
Entrepreneurship is not a career choice
An entrepreneur has to be a 60-percenter, because great ideas take a huge amount of thinking and effort to get off the ground, like the massive amount of fuel it takes to launch a rocket. But once that rocket escapes orbit, keeping it there requires more nuanced engineering and guidance systems.
The passion that drives a startup’s inception and its focus on growth and proving viability can often turn into boredom and malaise once the company matures.
The folks who are best equipped to get a startup off the ground are usually lousy at managing a big, established company. Don’t get me wrong, those two stages are not mutually exclusive — and in fact, over time, I’ve learned to become pretty good at the other 40%. But the passion that drives a startup’s inception and its focus on growth and proving viability can often turn into boredom and malaise once the company matures.
One personality type is always seeking out serial experimentation and launching new ventures, the other type is focused on maintaining profitability. For that reason, being an entrepreneur makes it tough to forge a career. I mean, how do you make being an entrepreneur a sustainable profession when it’s naturally built around trying something new?
You can try rising through the ranks at a startup, which can feel like corporate America repackaged for open-plan offices. You can succeed with your own startup, which is an awesome ride, but almost always a temporary one; the glow tends to fade after a couple of years of success. You can try to enter the world of venture capital and become an investor, which some entrepreneurs eventually do, but in reality those aren’t the same jobs at all despite them existing in parallel fields.
What I’ve learned is that the more an entrepreneur fits the 60-percent persona, the more consistently successful they are for a longer period of time. But only if they’ve pushed through the other 40% by honing those other skills and surrounding themselves with people who can fill their 40% gaps.
But wisdom taught me that just because I forge my own path doesn’t mean I don’t have to play the game. I still had to learn how to be a good employee, and eventually I did.
I get it now: Paperwork for paperwork’s sake, meetings to talk about meetings, hour-long debates on a single word in documentation. There are reasons for all of that. And they may not be the reasons that drive me to be my best, but for the most part, they’re there to keep the rocket in orbit. (Or maybe they’re there for me to challenge — but I don’t have to be a shitty employee while I do it.)
Redefine and reinvent what your career means
I’m a recovering 60-percenter, along with a lot of my entrepreneurial peers, but learning how to finally be a good employee didn’t lead me to find what I was looking for. Instead, I had to redefine what I was looking for.
I still have trouble explaining what I do to strangers — and even to my mom. My day-to-day doesn’t make for good cocktail party talk. There’s rarely an occasion where I meet someone new and can “talk shop” about the industry, because the industry I’m in now isn’t the industry I was in last year, or even last month. Or maybe my current industry is one that no one else is in yet.
I’ll admit that I get that little jealous twinge when big company bonus checks go out, or a friend gets a corporate junket to a place I’ve never been but would love to see.
I had to ignore everything I believe in about upward mobility and convert it into a sort of sideways mobility. Sure, I’m climbing a career ladder, but I’m also building each rung before I step up, and that can be maddening. And I’ll admit that I get that little jealous twinge when big company bonus checks go out, or a friend gets a corporate junket to a place I’ve never been but would love to see.
But I’m glad I had that corporate “fail year,” because it helps me remind myself that I don’t want a traditional office career. I get to choose what I do, who I do it for, how I give back, and exactly where my happiness comes from.
Here’s one battle I still fight: I still struggle with the fact that when I do actual work — work that generates value for me or someone else, whether that’s a customer, a colleague, an investor, or a partner — it doesn’t feel like work. It feels like I’m goofing off. After all this time and all this learning, it feels like I should be getting back to what I’m supposed to be doing.
If you can live with that, entrepreneurism may be an unorthodox and complicated career choice, but it’s a wonderful and satisfying life.