What it’s really like starting a business

For years I’ve said that starting a business is like jumping off of a cliff and learning to fly.

Somehow I flew.

Rent wasn’t cheap. It was 2008, and I was living in New York City. I was in my early thirties, single and stupid enough to leap off of a cliff without a parachute. All I had was a dream to be my own boss and some savings. So I wasn’t that stupid.

Jobless and hopeful, I went looking for my destiny. Friends kept on asking me when I was going to look for a job. And when I told them I was starting my own business, they laughed.

Things looked laughable. My appearance went from beautiful suits to shorts, clean shaven to scruffy. Before I was jobless, my practice was to be the first one out of my apartment; afterward, I was barely out of my bedroom after my roommates left. I was feral.

I was free-time rich but paycheck poor. Every day was free and open. Time was entirely my own to do with as I pleased. There was no routine, structure, external motivator.

The only thing I can compare it to is college: When you got dropped off your freshman year, and you realize that your parents are no longer with you to tell you what to do. You could skip classes, drink beer in the morning, if you were into that, and do whatever whenever you wanted. My life was like that, except I was in my thirties, not eighteen. And I had an NYC sized rent to pay.

The freedom wasn’t free. The price was stress. It was heavier than anything I had ever felt before. It was the fear of failure.

Some days it was too much. So in the morning, I would walk out of my apartment building, in shorts and scruffy, to watch a matinee movie. It was five dollars of relief from the vice grip of stress my head was in.

And what added to that was the waiting. When entrepreneurs tell their stories, they sound so action-packed. But what they don’t mention are the long periods of silence and solitude that fill the gaps between the action.

It can drive a person mad. Those parts are dull and miserable. They involve deep bouts of fear, worry, being curled up in a fetal position on the floor, murmuring unintelligible prayers to God. But they are a part of the process.

I had to learn to be still and pray (not in a fetal position) and get zen. I also watched Iron Man five times in the theater. But that’s beside the point. I had to learn how to wait well.

Curbing my spending habits was a part of survival. When I worked for someone else, I ate every meal out every day. When I started my own thing, I cooked.

Well, calling it that is generous. Bachelor food was all I could conjure up. So I didn’t cook. I microwaved.

Two hotdogs on a tortilla, with a piece of American cheese, slapped on top of the dogs, nuked for about a minute was my go-to meal. Then I took that hot gooey mess and wrapped it up into what looked like a weird burrito and devoured it like a wild animal. It was cheap, fast, and delicious. It was bachelor bliss.

Figuring out what kind of company I should start was harder than I thought it would be. I daydreamed, took walks, begged God, read books, and pounded my head against the wall. Then, instead of me finding it, it found me.

When I wasn’t watching movies in the middle of the morning or enjoying my James Beard Award worthy meal, or daydreaming about my future, I was meeting with people.

One of them was a client of mine from the bank where I used to work. We got along well. He was retired. I was feral. We both loved ideas and business and had the same faith. His favorite sushi shop and pub were our usual haunts. And we’d chew food and words; they were sweet memories.

One day, he asked me to help him with his hotel, which became my first paying gig. He hired me to build him a new website. I was relieved. I actually had income. It was a gift.

That relief quickly turned into a new terror. Now that I had a paying project, it dawned on me that I would have to deliver on what I promised I could do.

The only problem was that I was utterly under-qualified. I wasn’t a developer nor a designer. Sure, I had led a small volunteer arts group for my church, and oversaw the design of that website. But this was different. Real money was involved. And this website was for my friend’s business. I didn’t want to fail him. I didn’t want to fail myself. But I pushed forward, taking one step at a time.

But let me tell you something, that income felt incredible. It was very different from getting a paycheck from my jobs. This was someone paying me–directly. And the payment resulted from my meeting and talking about what value I could provide. It had originated from my work. Yes, it was mostly luck, but there was still a smidge of something that I did. I showed up. And money started to flow. It felt like magic. It was magic.

The project finished with my client sending me to Northern Ireland (as seen in pic above) to stay at his boutique hotel to take pictures of it and the surrounding landscape. It was a dream. And the best part was that my friend appreciated the work and even recommended me to others. He was the gift that kept on giving.

When I reflect on that time, I see how little I did. Yes, I jumped off of that analogous cliff, but somehow I was guided by something or someone. The timing was just right, the experiences I had prepared me just enough to try, and I had a network that worked in my favor.

I didn’t learn to fly.

I was lifted up.

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