Confessions of an Entrepreneur

Rule One: It ain’t all that glamorous.

Sometimes the ‘entrepreneur’ word gets over-applied to include everyone who ever sold a used toilet brush on eBay. But that’s not what really hurts.

Others feel being an entrepreneur means millions in the bank, a ‘make your own rules’ rebel who’s untethered from the constraints of job haters everywhere.

Actually, the toilet brush example is closer. But here’s the ever-loving truth about being an entrepreneur...

An entrepreneur knows their ‘job’ isn’t selling, or marketing, risk-taking, freedom or having some boldly attractive new product. Because at its core an entrepreneur’s job is:

Lonely as heck.

You have a vision for betterment that most others can’t see. You almost get tired of telling it, so you get selective about sharing it. Sometimes you dismiss it entirely or reframe it to be spared from explaining yourself.

To give your vision a fighting chance to live, you had to fight for it. The foes were many, better equipped and can out ridicule you with one “that’ll never work” tied behind their back.

Most can’t even see why you’re in the battle. Others feel you just really need to stop working so hard and drink a beer. They entice you. “We’re done with work at 5. We’re gearing up for a weekend. Heading out on a 4-day hike and kayak trip. You?”

“Can’t. Working. Gotta get this done.” You knew what “done” meant. It darn near meant “never.” It definitely meant long hours, weekends that weren’t, checking stuff off an unending list. At times you could sense your competitors. You felt they were going to outflank, outmove, beat you to market if you didn’t do this one other thing tonight.

For 6 years while building Hudson, Ink, I spent at least two nights a year working around the clock, literally without any sleep, working solid through the next day. The vision was my muse and my menace.

You know what I mean.

You have worked on your vision because it wasn’t taking no for an answer.

You have paid the mortgage when your fingers hurt to write the check, for more than one reason.

You have paid employees more than you took home, and you did it smiling, grateful, but at some level with a sense of mild futility.

You have refunded customers because it was right, not because you could afford it.

You have told your wife “It’s fine” when it wasn’t, but your vision disallowed another answer. You wanted her belief, but she could feel the finest fissure in your confidence. In her support, she never revealed she knew the truth. You both lived on half-truths of full faith.

You told your friends little of the struggle. They had real jobs. Anyone who’d advised you “not” to do the thing were off-limits for the “I told you so” of predictable smugness. Like I said, a lonely place.

Then the tides shifted. Things formed where things weren’t before. Customers. Sales. Income. High fives. A sense of accomplishment. Systems to replicate. And the true mark of having value?

Suddenly insurance people appear, business cards in hand. Lenders who were in the “You’re an idiot!” camp now miraculously laud your vision, and welcome your signature on Page 4.

Others want to “know how you did it,” and you don’t know where to start.

I’ve seen people go one of two ways from here.

One: They announce how they did it. They were right all along. They had a better idea. It’s all rosy now. We’re wallowing in success.

Then they’re not. Muses do not like being left out of the final credits.

Two: They’re grateful beyond measure. They gained more lessons in the hardship than the soft landing. They thank the people who didn’t give up on them. They entitle themselves to the gift of having listened to a small voice saying “You can do this.”

At a time when I was really lonely.

I appreciate that in you too.