How I became an entrepreneur; or, The greatest story ever told

I only became a full-time businessperson and entrepreneur a few years ago. I’d toyed with the idea of working for myself most of my life, and had even taken odd freelance gigs here and there as they presented themselves.

Still, I had never before completely severed the tether to consistent income and security until early 2012.

The reasons for it are varied. In retrospect, it was a perfect storm. I had just graduated college as a non-traditional student, and my mind was swimming with theories and ideas. Inspiration had recently come into my life. And, frankly, I didn’t have much else to do: I had applied to some decent jobs in the Bangor area with my new degree that ultimately went nowhere. So is life.

So I decided to strike out and capitalize on an idea. I had been entertaining a couple of ideas for years, but ultimately never acted on them. I still think some of them are quite good. Unfortunately, most of them took capital that I just didn’t have. So I latched onto one that took almost no capital, and dove into the cold waters.

It wasn’t easy. I mean, the work was easy: I had been doing it for years and I enjoyed it. But the transition to a life of living by the skin of my teeth, of uncertainty, of sheer terror, was jarring. I consulted, researched, read, and even wept once. The immensity of my decision was overwhelming.

They say that fortune favors the bold, and I believe that. I also believe that things always work out in the end, a maxim I often espouse (much to the chagrin of family and friends). Armed with these two guiding principles, I forged onward. Now, I oversee a sprawling empire of riches and avarice.

That’s not really true. I do own or co-own several enterprises, and as any business owner will tell you, things don’t always come up aces. Sometimes you don’t know what to do with your all your money, and sometimes you don’t know what to do because there’s literally zero money. Most frequently, you exist on a teeter-totter between the extremes, shifting your weight back and forth and trying to forecast the next breeze.

I’m not saying I’ve “made it”. I’m still in business. Something else that any business owner will tell you is that you live with this very real fear that any moment, the rug will be pulled out from underneath you. You prepare for that. There’s no safety net. You are the safety net.

Even at my most stressed, however, I tell people that I’m the happiest I’ve ever been. I look back on times walking on sunny San Diego beaches, the births of my daughters, my marriage in Jamaica, and all the other supernovae illuminating my memory, and they make me smile. They fill me with warmth. But the immense, continued satisfaction I get from charting my own course and being the master of my own fate is the most unendingly salient.

As a business owner, I have less time, but I also have way more freedom to use the time I have. My mind works triple-time. I lost friends who either couldn’t adjust to my diminished social freedom or who didn’t care to maintain it. I made new ones. I go longer without haircuts. Above all, I gained an incredible sense of self-empowerment and pride.

Being an entrepreneur isn’t for everyone. I don’t declare this from some gilded throne of success. I actually write this from a living room in Bangor, Maine, worrying about the next snowstorm as I sit next to a pellet stove that’s in constant need of repair. Anyone who thinks they’re going to work for themselves and immediately rake in money Scrooge McDuck-style is wrong. Really, really wrong. But, if you have a good idea, then have other good ideas, and make some of those ideas happen with tenacity, guile, and a decent goddamned attitude, you might make it. If you often find yourself blaming your friends/family/society/government/the weather for things that affect you, you won’t. You just won’t.

In order to be the master of your own fate, you have to start by being the master of your own fate. No one else will do it for you. If you want it, do it.

There’s a lot of advice floating around out there on how to start a business. This comes from family and friends (sometimes they’ll help, but usually they’ll scare your pants off) to bona fide business development organizations who will often tell you to continue working full time while you’re starting out in order to make ends meet, which also sounds horrifying to me.

I’m not you. You have to do what’s right for you. If you want to jump in, then do that (just have some sort of viable revenue plan, please). If you want to take baby steps, that’s fine too. Steve Jobs was incapable of working with other people and jumped into Apple whole-hog. J.K. Rowling wrote Harry Potter and the Sorcerer’s Stone over a period of seven years while teaching English in Puerto Rico and suffering from depression.

You’re not Steve Jobs and you’re not J.K. Rowling. Neither am I. I took a chance and I’m glad I took it. Do you want to be an entrepreneur? If the answer’s no, then hey, thanks for reading this post! But if the answer’s yes, well, it’s on the table.

You have to start by being the master of your own fate. No one else will do it for you. If you want it, do it.


Matthew Chabe

About Matthew Chabe

Matt Chabe is a principal at The Galleon Agency, an integrated marketing agency based in Bangor, Maine that helps businesses around the nation maximize growth. He is the chair of Bangor SCORE, a seven-year veteran of the U.S. Navy, and drives way too fast for his own good. Matt graduated from University of Maine with a BA in marketing and a minor in psychology.