What I Didn’t Believe About Being an Entrepreneur


In August 2014, I began to think of myself as a true entrepreneur.

The feeling lasted a couple of weeks. Then began the roller coaster ride of struggle, success, self-doubt, and high-fives.

Let me be clear, this isn’t a “what I wish I knew seven months ago” type of post, because many entrepreneurs have been very open and honest about the struggles and challenges of startups. I simply didn’t believe them.

Since I graduated the University of Florida in December 2006 until August 2014, I had been employed for all but 12 hours of that span. When I switched jobs from startup sports marketer and coach to summer camp assistant director, I spent the night with my old roommate, hitched a ride from Atlanta to Asheville, and was right back in the saddle. For 6.5 years, I had never missed a paycheck.

In fact, I was ready to be on my own. A steady informational diet of Seth GodinPat FlynnJason FriedEric RiesJoel & Leo, and Gary Vaynerchuk had built the mindset that I was ready to strike out on my own, build a business, and be location independent. I was tired of being told all five W’s and the H:

  • What to do
  • When to do it
  • Where to do it
  • Who to do it for
  • Why I/we do it
  • How to do it

Sound familiar? The whole live-anywhere-do-anything entrepreneur ethos was ripe for the taking, and I was going to take it.

The story since then? Simply days of hard work, great experiences, cussing at myself in the woods, depression, elation, flexibility, demands, and patience.

I didn’t believe I would be just as pressed for time, meeting the needs and demands of clients. I was location-independent, but not time-independent.

I didn’t believe I would need to work part-time, and feel the embarassment of telling people at parties that while I’m an entreprenuer, I also sling cardboard for UPS.

I didn’t believe I would suddenly try to abandon my startup hopes and look for a job, placing my self-worth in someone else’s hands, wanting them to tell me I was good enough, smart enough to work for them.

I didn’t believe I would mentally rely on the affirmation of other people, or be jealous of their success.

I didn’t believe I would take so long to figure what I should concentrate on, and be so willing to jump at any opportunity. I’ve called myself a web developer, writer, brand manager, social media marketer, artist, podcaster, and growth hacker. Which doesn’t include my “legitimate” side jobs at UPS, substitute teaching, and Lyft.

I didn’t think I’d be running through the woods cussing myself out for being selfish and lazy, then laying awake at night thinking about client projects.

I didn’t think I’d be so tentative and desperate in pricing, and willing to price my talent so low, and then work really hard.

I didn’t think adjusting my buying habits would be so difficult, since I had convinced myself I was “above” such consumerism and worldliness. If you asked me now, I could rattle off list of things I want to possess.

Finally, I didn’t think the mental challenges of building a business and getting work done would be as daunting as they are.

What I do know now is very similar to other lessons I’ve learned in my life. Most lessons need to be learned personally, in the struggle and success of the arena. We cannot sit in the stands and only read about what those daring greatly are doing, their tactics and advice. Of course, doing so is immeasurably helpful, but as Mike Tyson famously said,

Everyone has a plan until they get punched

I’ve been getting punched, but now I’m punching back. There’s no substitute for getting the in the ring and seeing what you’re made of. Train hard, do your research, and have people in your corner, but eventually you’ll need to step in to the arena and dare greatly.

I believe that with my whole heart.

Did this resonate with you? I’d love to hear your thoughts and stories. Please leave a comment below, or connect on Twitter. And yes, I drew the picture, impressed?