3 Experiences That Inspired Me to Become an Entrepreneur

I’ll be honest with you — I never wanted to be an entrepreneur.

My theory is that some people are born with that fire: they know they want to create, they want to lead, they want to build something bigger than themselves. I’ve admired them. I’ve envied them. I still do both, to an extent. Because despite the fact that I am an entrepreneur*, it’s not where I imagined I’d ever end up.

This statement begs an interesting question that goes along the lines of, “well then, Renee, what in the world are you doing?” And as the Number One Expert in asking myself that question (1-3 times daily, on average), I’m here to tell you how I ended up starting my own freelance business…because I have a hunch that I’m not the only entrepreneur who ever woke up to find themselves an entrepreneur and ask, “how did I get here?”

WHY DIDN’T I WANT THIS?

To make a very long story very short: It sounded hard. It seemed like a lot of responsibility, and I didn’t believe I could do it.

Entrepreneurs deal with so many things that I knew nothing about, and I even felt intimated to learn about them. For instance, could I figure out anything about complex business finances on my own? I didn’t even figure out how to manage a normal, basic budget until my mid-twenties (thanks, high school, for teaching me advanced geometry, though).

Did I have the drive to pitch myself constantly, to network relentlessly, to hustle even when I didn’t have the motivation?

Did I have the follow-through to create my own schedule and stick to it? Or the organization to keep track of my systems and products? Or the confidence to make people think that I knew exactly what I was doing even when I was figuring it out on the fly?

Did I have the fortitude to set my own prices and not waiver if/when people tried to talk me down? Also how do you decide on pricing? Also should you post your pricing or make people call you for it? Also before I talk about pricing, is there even a market for what I offer? Also what about marketing? Also helphelphelp.

These questions scared me and, in a common response to fear, I shied away from them and the whole entrepreneurial concept in general. If the answer to any one of these was, “no,” then I would fail, of course. And failure is scary and sad and embarrassing, of course. And I can’t allow any of those things to happen to me, of course. So even when I started answering a tentative “yes” to some of these questions, my fear of failure managed to outweigh everything else. Until…

WHEN I KNEW

…until three things happened within the span of a year and half, in this order: I took a month-long cross-country road trip, I worked my first ever full-time job (at a wonderful company) and I worked for The Worst Boss On Earth (at a terrible company).

REASON #1: I TASTED FREEDOM

The road trip was from San Diego, CA to Asheville, NC and it took about a dozen detours, zig-zagging up and down California, Arizona, Utah and Colorado before bee-lining across the midwest to western NC. I made the trip with my partner and we camped almost the entire way, living out his Jetta which was packed to the brim with all of our belongings.

It wasn’t glamorous. It was cramped. It was dirty. It was the best five weeks of my life.

Mostly, it was freedom. It was nature and fresh air and limited cell reception. It was lounging on the banks of rivers and hiking massive mountains and building fires and going to sleep with the stars as our ceiling. Before I moved to California less than a year earlier, I’d never been further west than New Orleans. Now I was sleeping in National Parks I’d only ever seen in pictures.

I spent a few restless nights under those stars thinking about how going home meant getting a full-time job, which meant that we’d maybe have two weeks a year to do things like this from here on out. I knew it was time for me to Be An Adult and Get A Real Job and I knew limited vacation time was part of that, but the concept already felt stifling (I feel like I should also mention that I’m a Gemini, an Enneagram 7 and an ENFP. So if any of this resistance is surprising…it shouldn’t be).

REASON #2: I TASTED CONVENTION

So when I got home and got my first ever full-time job (I’d been a dedicated-student-with-multiple-part-time-jobs gal before then) and I was given a little less than two weeks of PTO as a new employee, I was deflated by how spot-on I’d been.

But I had health benefits. And I loved the company and what they did. I enjoyed the stability and the guaranteed paycheck (an absolute dream for someone who spent a large portion of her working life depending on tips). It was four 10-hour days, so I had three days off per week. The job itself was rarely too hard or stressful. I fell madly in love with almost every person who worked there. In fact, I had no real plans to leave, figuring I’d coast along and maybe work a mobile side gig that I could eventually turn into a full-time thing down the line.

But.

But in essence, it wasn’t freedom. And fresh-from-a-cross-country-road-trip Renee became depressed at the idea that that was what all the fuss had been about all these years — get your education, take part in the right extracurriculars, get the right internships and rack up the right experience so that you’ll be appealing to the right salaried positions. Make money, aim for promotions that get you more money, take your allotted vacation (when you can), make sure you save a little PTO in case you need it for sick days, and welcome to the system by which you will live the rest of your life.

*insert cartoon dust trail left behind by the Roadrunner as he dashed away at impossibly high speeds*

I started aiming for freedom with baby steps. My partner and I bought a van. We began making plans to build it out and travel around. I began thinking more critically about a mobile job so that I could work from the road.

So when another opportunity arose with a more flexible local business that had a more generous and flexible time-off plan with more creative liberties and more growth opportunities (and a $6/hr raise, hellooo), I accepted. It felt like a step in the right direction: more freedom, more flexibility, more creativity and more growth — four things I’d realized were important to me in a professional setting.

If only I’d known that the local business that offered me this position came with the worst boss I’d ever have.

REASON #3: I TASTED INSANITY…AND USED IT AS MY LAUNCHING PAD

To be honest, I still would have taken the job. If I could go back, even knowing how terrible it would be, I’d still accept the position. Because dealing with That Boss is what launched me (with the speed and intensity of a launching cannon) into my entrepreneurial pursuits.

I won’t get into the nitty gritty of what made this person a horrendous boss. We’ve all had one (or currently have one, and if you do…my spirit is standing in solidarity with yours). A terrible boss is nothing new, unfortunately. Poor leadership happens, and the effects of its incompetence and/or abuse are both unfair and infuriating for the genuinely competent people who work for them. Some people simply shouldn’t be bosses. Some people should really only be in charge of themselves because you get the feeling that that’s hard enough for them already.

I will say this: the way this person operated (and especially the way they treated others) caused, within me, an irrepressible need to escape like I’ve never experienced before in my life (which is saying a lot for a Gemini/Ennegram 7/ENFP). Somewhere in the world are people -much better people- who would understand this person’s extreme, immature and passive aggressive behavior as insecurity and approach it with compassion. I approached it with equal amounts of fight and flight, in that order.

Which is why I have found, in my time since leaving that position, that I am actually quite grateful for that terrible boss.

Because honestly, without the intensity of the circumstances, I might very well still be there.

If That Boss had been even marginally more competent (or, heaven forbid, had been a Great Boss), I’d likely be there now, glad for the stability and semi-decent paycheck, too nervous or guilty to leave, feeling partially content but mostly restless, knowing that I could do so much more if only I had the motivation.

Luckily for me, they were not a Great Boss (hard understatement, but you feel me). Yet I still had a dilemma.

I couldn’t (wouldn’t) go back to a regular salary job with fixed hours and fixed time off. I’d learned that it wasn’t for me, and it was (is) scary to think about how few options that knowledge left me with. What job would allow me to choose what I wanted to do, choose my own hours, choose my own boss, choose my own co-workers, travel whenever I felt like it AND still, by some miracle, make a living?

To this day, I’ve only ever found one answer to that question: start your own business. Become your own boss.

And that answer is how I ended up here: an entrepreneur/solopreneur/freelancer who builds websites and writes things. And “here” isn’t always sunshine and rainbows. It’s mostly learning how to exist in a constant state of learning, reaching, trying, experimenting, and figuring things out as you go. Despite my penchant for freedom, it’s a level of autonomy that tends to scare me just as much as it inspires me. And it takes courage to exist there, in that state, and I don’t always have courage in spades. It’s a roller coaster - and I don’t know how long the ride will be, but I’m strapped in and ready for it.

Because “here” has everything I realized I wanted over the last couple of years: freedom, flexibility, creativity and endless potential for growth. And at the end of the day, that’s what it’s all about: realizing what you need and want from your work and making it your reality — even if that is a 9-to-5 job, even if what you need/want changes every few years, even if you haven’t figured it out yet. Simply following wherever your growth leads — to me, that is success.

Because for a while, I thought I stumbled into entrepreneurship, but it turns out I grew into it. I was always headed here — it just took me a handful of years, an epic road trip, a conventional job and a crazy boss to figure it out. Sometimes it takes you a while to grow into the things you were meant for. Be patient with yourself. Regardless of how lost or stuck you may feel sometimes, you’re always on your way.

So whether you were born with the fire, found yourself in the middle of it or are still gazing at it from afar, wondering if its for you — however you get there is the right way to get there. However long it takes you is the right amount of time. And whatever your reasons are, they’re the right reasons for you. Keep on truckin’.

Because while a world of uncertainty may await you, a world of freedom, growth and possibility does, too.