The first installment of the “Self-Annoyed: Solo-preneurship Done Write” series, where I openly battle for control over my mindset + wrestle with cultural myths about success.

Four years ago, I quit my job. I ditched a short-lived, mediocre, accidental career in hospitality armed with nothing but a dream (or, rather, the dream of having dream) and a small pile of savings with which to make Something Big happen… or at least pay for groceries while I made my indelible mark on the world.

Did I feel scared? No. I was thiiiis close to popping out my first baby, and the magical “mama positivity” hormones were flowing. On a continuous sugar high that stemmed from my pregnancy-induced cravings for caramel cake, there was no doubt in my mind that my quitting gainful employment would lead to stardom.

Did I think it would be hard? Kinda. I’d heard that the entrepreneurial road was rough. But dude, I had a master’s degree. I was almost 30. And while I had no idea what, exactly, I was going to do, I totally had this thing in the bag.

Over the ensuing four years, I used my fancy-pants master’s degree to master the art of mastering nothing. First, I tried my hand at private mediation, then coaching — initially for new parents, then newly-married couples, then absolutely anyone experiencing relational conflict.

On paper, I did everything right: developed my client avatar, created a mission statement, decided on that all-important value proposition. Nothing worked. Nothing fit. Nothing added a single penny to my bank account.

In a panic, I grasped at a few more hat trick ideas.

Go back to school? Okay, that would offer a bit of direction and focus, while giving me some time to delineate my Life’s Purpose. But with a second baby on the way, sheer exhaustion precluded me from scoping out a school or degree program, and my debt-to-income ratio from previous dealings with higher education left me void of any desire to go that route.

Write a book? Hell yes. I’m sure I have something important to say to this generation of young moms. After all, I’m a young mom with goals, ambitions, and mad spelling skills. I sat down and outlined the nine chapters of my soon-to-be bestseller, but lost steam somewhere around page one of the manuscript.

Then, I joined a MLM company and annoyed the shit out of all my Facebook friends, losing some in the process.

Hello, rock bottom. Nice to meet you.

It was there, in the pit of despair and self-loathing, that a conversation with a close friend changed my entire perspective and altered my course completely.

Friend: What do you like to do?

Me: Write.

Friend: Why don’t you become a freelance writer?

Me: You can’t make any money doing that.

Friend: Why don’t you just try? You’ve got nothing to lose.

BOOM. Truth bomb.

From the moment I quit my job, I worked incredibly hard to avoid doing the ONE thing I’d always secretly wanted to do, because I’d become absolutely certain that it would lead me nowhere. I spent so much money, time, and precious energy talking myself out of freelance writing, it almost felt like sweet relief to stop fighting so hard and just move forward.

This time, I didn’t allow myself to hope for success. I didn’t entertain great visions of grandeur. I didn’t even make business cards. All I did was shrug my shoulders, accept my fate, and begin introducing myself at networking meetings as, simply, “a freelance writer.”

And suddenly, I was. Slowly but surely, folks began calling with writing needs. I began taking on small projects, then landed my first ongoing client. Out of sheer necessity, and still with an air of reluctance, I formed an LLC, set up a simple website, and updated my social media accounts. Soon, I purchased an inexpensive package of freelance contract templates to protect my business, because I finally had an actual business to protect.

Deep into my first year as an official “freelancer/ consultant,” I have both kicked ass and had my ass handed to me through hard and humbling lessons. You can’t understand, nor prepare for, the freelance life beforehand, just by peeking in. You have to live it. You have to learn lessons on the ground, as you go.

This journey is equal parts adequate preparation and flying by the seat of your pants as you face down the unforeseen aspects of client expectations, projects that call for a quick update of your skill set, or that are simply outside your normal scope of work. You learn when to say yes, when to say no, and when to keep your mouth shut.

Freelancing (and self-employment in general) is, in part, about proactive preparation and effective time management, which happen to be strengths of mine. Even so, being a freelancer is fucking hard, for one glaring reason: my own mind is my enemy.

Here’s a quick snapshot…

When things are going good, I have to actively quiet the parts of my mind that tell me I’m the most awesome person ever and nothing will ever cripple my success. When things are going badly, I must battle against the thought that everything is crashing down around me, that I’ll never amount to anything, and that my kids will someday hate me for even trying to do something with my life.

As intense as this inner struggle feels, it pales in comparison to comparison itself. All day long I’m confronted on social media and in real life by people (who appear to be) doing much better than me at this entrepreneur thing. I’m confronted with messages about how to “get more followers,” “diversify my income,” and “network better.”

As a result, my mind is constantly flooded with questions: Should I be creating passive income right now? How do I even do that? Do I need to create a sales funnel? Why have I not figured this stuff out yet? Why don’t I have any ideas about this? Am I a total idiot? Oh my God, I’m going to fucking fail at this, hard.

I’m determined to be a fucking awesome entrepreneur, therefore I’m tasked with facing down my inner demons and gaining control over a mind working against its own success. This path is often portrayed as a yellow brick road to an emerald city of riches and glory, but it’s littered with landmines and the battered souls of those who came before me. (And is that emerald city actually just grass huts covered in moss?)

This is a brutal climb up the steepest mountain, and many days, we’re groping in complete darkness to gain a foothold and advance a single inch. If we’re going to make it to the summit, we need hope. We need comfort. We need realistic goals.

Instead, we’re offered “5 Easy Steps to Success” by doing more, being louder, and spreading ourselves so thin, we’re invisible. It isn’t tough to find advice on how to build your business, or become a successful entrepreneur. The tough part is deciphering which advice is worth following, and which — though perhaps created with helpful intentions — is just crap covered in glitter that will get your wheels spinning in place.

I don’t know about you, but some days, my experience of entrepreneurship is pretty dark. Oftentimes, I feel like I’m groping around in a dimly-lit cave, lost and forgotten. But I know I’m not the only one in here. You’re in here, too, wrestling with the same insecurities, self-doubt, and fear that I do. You’re riding the rollercoaster with me, dreaming of a future where your climb isn’t met with sudden gut-wrenching drops, and your falls are less of a plummet, more of a glide.

We’re in this together. Why don’t we hold hands for solidarity?

Wanna carpool with me on the highway to “success” (whatever that means)? Follow my blog for regular installments of the “Self-Annoyed: Solo-preneurship Done Write” series, and let’s feel every shred of the crazy/ excited/ terrified/ badass together.

Psst… Visit my website to discover why I’m the gal to craft killer creative content + copywriting to level-up your business.

Writing + abiding in Montana (or wherever’s clever).