You Might Just Be Smarter

Or you would have started your own business by now

Photo by Ezequiel Garrido on Unsplash

It wasn’t my best presentation, to say the least.

I was distracted by the fact that my toddler son was perched on top of a stack of ballroom chairs in the busy hallway behind me in the banquet kitchen. I’d managed to communicate to a kind dishwasher who spoke little English that I’d pay him $20 to keep an eye on my kid, and told one of the conference servers I had an unlimited budget for ice cream and that she should keep his bowl full until I was done.

It had been a last minute decision to bring my son on my work trip due to extenuating circumstances at home. I couldn’t call in sick to my boss or supervisor, or request that a colleague fill in on my behalf. Foregoing the pay-day from a booked speaking presentation was not an option, so there I was in a less than ideal situation, duct-taping my way through it.

I jumped off-stage, ignored a small queue of attendees wanting to have a word, and made for the kitchen galley where my kid’s clothes were indistinguishable in color from the ice cream, some of which had presumably been ingested as evidenced by the large smile on his sticky adorable face. I had packed just one change of clothes for a three-year old on a two-day trip. That was the sort of dad-math my wife would roll her eyes at and correct when we traveled as a family, but I’d left her behind fighting a bad flu with our newborn. All on my own, I was now discovering that the smug, paternal way I calculated the traveling needs of a small child bore no semblance to reality.

Colliding challenges like this have been the norm in the last 30 years of self-employment.

The holy grail of autonomy—that coveted prize of being one’s own boss—gave me complete freedom to decide which 20 hours of each day I’d be working. With the track record of an above average income, I could create my own system, course, or set of instructions for how to be married with children and run your own business, claiming that if you followed the same steps you’d succeed and be happy like me. And it would be a complete lie.

There is no way—no map, no traceable path that can be passed along from one entrepreneur to another.

In my case, the system would have to include developing deep-seated authority issues that make you unemployable, moving homes as often as you get an oil change, living off of donations from street performing for ten years, becoming a dual citizen and inheriting the privilege of filing four tax returns each year in two countries, being solely responsible for the marketing, sales, technology, accounting, legal, and delivery of services for your own company, making sure your autism remains undiagnosed until you’re 60, leaving your first marriage with your immaturity fully intact, and dragging your children across the country to leave them in the hands of strangers while you attempt to work.

The decision to start one’s own business has a big effect on other human beings. When we launch into it unprepared, we put other people in the crosshairs of our inexperience. Self-employment is going to make your life and the lives of others . . . complicated.

You’d think the gravity of such a commitment would motivate anyone to take it on in a thoughtful and considered fashion. That doesn’t seem to be the case, however. Some of us leap into self-employment with surprisingly little friction and, in some cases, on the tailwinds of enthusiastic encouragement from others to throw caution to the wind and go for it. Never mind that when we have no idea what going for it entails down the road, it just feels good to say yes in the moment. Kind of like having kids.

There comes a moment when it feels like you’re simultaneously trying to solve several five-sided Rubik's cubes while riding a Disneyland roller coaster and assembling an Ikea cabinet all at the same time.

If you’ve had an idea for starting a business and if you’ve shared that idea with anyone else, especially if it’s a good idea, you’ve likely been at the effect of internal, external (and probably nocturnal) voices that keep whispering, “Hey, when are you going to start that business?” And for every day that passes from the inception of your idea, some part of you or your circle of family and friends is judging you for not taking action.

Well, I’m here to put your sense of inadequacy and incompetency to rest, because the very likely reason you haven’t started that business by now is that you’re smarter than most people, not less courageous.

You’ve accurately intuited the lay of the land and you sense that launching a start-up to do your own thing is not going to be a walk in the park.

And you’re 100% right.

Here is a list of values you might hold that are causing you to pause in relation to launching your own business.

• You have absolutely no desire to add another product or service to the moon-high stack of companies bombarding the good people of planet Earth with ploys to capture and dominate their attention in order to meet sales quotas.

• You don’t want to fill 20 hours of every day with work-related activity because you actually like your family and friends and you want to spend some time with them.

• You like the thing your business proposes to do, you have some expertise in it, and you’re afraid you wouldn’t get to do much of what you love as you try to build a business around it. (Professional photographer Matthew Jordan Smith admits that he spends approximately 1% of his time actually shooting photos.)

• You value your mental health and don’t wish to add whether you’re going to get paid next month to your list of concerns.

• You like having supervision that provides clear expectations that you can achieve so you can feel good about something you’re contributing to instead of starting each day staring at a list of 217 possible tasks and then spending 90% of that day hand-wringing over which ones to tackle first.

• You don’t want employees, especially remote ones, and the responsibility of structuring their days and focus when you can barely provide direction for yourself.

It seems to be true that we’re all different types and some people just cannot work for somebody else. There is such a thing as an entrepreneurial spirit, and some people are just predisposed psychologically to be self-starting and self-employed. And if you are such a person, you’re probably not reading this. You’re out there doing your thing already.

On the other hand, if you are still here reading this, some part of you is probably questioning the whole entrepreneurial ballgame and wondering if you should get on the playing field.

Let me just say that I deeply wish I could not be an entrepreneur but, after 50 years, to sign up to be somebody’s employee would be an act of rapid and gruesome unraveling that no one would benefit from witnessing. I’d be staging a hostile makeover of the organization in my own mind before my first lunch break, cuz that’s what enterprising brains like to do.

Despite the energy and promise of pop-culture hustle memes—which if you follow them back to their origins all probably have DNA traces from Gary Vaynerchuk’s toothbrush—having an entrepreneurial spirit is at least as much of a curse as it is a blessing.

So regarding this entrepreneurial spirit, if it’s in your bloodstream, so be it. But if you don’t already have that spirit in your veins, why in the world are you thinking about trying to inject it?

There are so many ways to improve your lot in life that don’t require falling asleep at your desk at 2 a.m. and waking up in a puddle of drool that has stained the grant application you need to make it through the next month.

Go home at 5 p.m., have dinner with your family, play Monopoly to satiate your entrepreneurial fantasies, get a good night’s sleep, and have the bandwidth in the morning to hug your kid, walk your dog, or dance in your vegetable garden while the sun rises.

There’s a lot to be said for a life like that.

I wish I could join you.