Big, Dumb Stallion

Part IV of the “Self-Annoyed: Solopreneurship Done Write” series, where I openly battle for control over my mindset + wrestle with cultural myths about success.

I’ve always believed, deep down, that successful business building is about more than just working hard – there’s a bit of luck involved, too. You can only get so far in life by waiting for things to happen to you, but you also can’t force your way into your destiny. It happens one step at a time. I’m still waiting on my call from Oprah to feature on her show and share my myriad talents, which will obviously launch me to instant, lifelong fame… but until my ship comes in, I plan to keep hustling, making the most of every small opportunity.

Like life, this entrepreneurial gig is a torturously winding road, the goal being to wind up someplace better, cleaner, bigger, and shinier than you started. The good news (and bad news, I suppose) is that you never know when your next “big break” will be. Each seemingly miniscule decision to do (or not do) something could alter your course entirely, and for that reason, I agonize over every opportunity that comes my way. After all, it just might be my Golden Moment. And, quite honestly, I’m trying to avoid entrepreneurial FOMO. #TheStruggleIsReal

So, when an intriguing job posting appeared in my inbox last month, it gave me pause. A company out of Montreal was looking for a copywriter. Hey, I’ve never been to Montreal… and I’M a copywriter… Immediately, as is the norm, my “Mommy mind” jumped into action. You can’t possibly consider this. They want you to fly to Montreal twice a year. It’s more hours than you’ve worked previously. You simply can’t be a mom, wife AND do this. It’s impossible. Truthfully, the position was a big leap for me in a lot of ways. But before hitting delete, I took some time to mull it over with my trusted business advisor (my husband, Nick).

After much deliberation, we decided that it might actually be a worthwhile opportunity, both for me (because I’d get to be an “officially” paid copywriter *SWOON*) and for us as a family (because the paycheck had to be enormous… it just had to be). Despite the warnings about a long application process and the inevitability of semi-regular air travel – a sizeable difficulty from my current location, to say the least – I chose to go for it. Grab life by the balls, as they say.

The next three weeks were a blur. Every day was a carefully orchestrated balance of time with family, writing projects for my freelance clients, and timed copywriting tasks for my job application. It was tough and sometimes tedious work – particularly because my computer imploded, leaving me with nothing but an iPhone and the will to survive – but it felt invigorating to try something new and completely out of my comfort zone. With visions of posh vacations and yachts swimming around my brain, I ruthlessly hammered out every assignment, determined to earn that six-figure income I clearly had coming. (Let’s face it: entrepreneurial life and delusions of grandeur come hand-in-hand; sometimes, they’re all that keeps you going).

Slowly but surely, I made it through four rounds of writing tests, holding my own against other, perhaps more professional copywriters with far more experience and, presumably, a working laptop. I endured the insanely rigorous process thanks to blind ambition, pure and simple. Each time I received an email notifying me that I’d passed the previous round, I felt both encouraged about my writing skills and completely uncertain that this was what I actually wanted. No matter – there would be time for deliberation later. My goal was simply to complete each task set before me, following the footsteps toward my Golden Moment.

Eventually, after completing multiple hours of writing tasks, online skills assessments, and an introductory interview, I reached the final round. Having convinced myself that this opportunity was my next big break (or, maybe because I just didn’t want to miss out) I dove optimistically into the last interview with the company’s founder and CEO. Everything moved along smoothly, until, a few minutes into our Skype conversation, I was asked a pivotal question: are you sure that, after freelancing and running your own schedule, you’re ready to work for just one company?

In the moment, I didn’t realize the weight of those words. Out of habit, I answered how a good applicant should – that of course I’m ready, because I want a more stable workflow and to feel part of a team. Still, the question haunted me long after the interview ended. Was I ready to be locked down? My polished, professional side voted “yes.” You need this, it will look great on your resume. You’ll finally be an ACTUAL, legit copywriter, plus you’ll get PAID.

But my heart said otherwise. Your favorite part about freelancing is running your own schedule and picking your own projects – you crave variety and new challenges, and this job will stifle you. Still, it’s hard for the heart to compete with cash money. In the end, I quieted my conscience by striking a compromise: if the job paid a certain amount, I would take it. Hands down.

The offer letter arrived just hours later, and I resisted the urge to open it right away. I wanted to exist in the realm of dreams and possibility for just awhile longer before succumbing to the “real world” of difficult decision making. When I finally read the letter, I felt oddly relieved. The pay was much less than I’d anticipated. Certainly not enough to power me through months or years of repetitive marketing copywriting and bi-annual trips to Montreal (although I’d still love to visit someday).

Within thirty minutes, I’d composed and sent a polite but straightforward rejection email. I stood my ground, placed my bets firmly on myself, and I’d never felt more like an asshole. My corporate American brain wouldn’t let up. You applied for a job, then got the job, then TURNED IT DOWN?



For the moment, I wasn’t sure of the answer to that question. I’d never turned down a job before, and the decision seemed either very badass, or incredibly stupid. My decision countered everything society trained me to hold sacred: a steady paycheck, a solid resume builder, job security. I had just walked away from all of those things. And for what?

Sure, I’d received a few phone calls from some of my favorite clients to partner on big projects – that definitely helped ease the initial panic. But, as I’ve learned time and again in my short freelancing career, no project is ever set in stone. The road ahead wasn’t particularly rosier than it had been previously. In fact, immediately after turning the job down, I finished up a handful of client projects and dropped right into two solid weeks of no work.


So, what was the point? Because there has to be one. Otherwise, I wasted a heck of a lot of time on an opportunity that pretty much landed me right where I started. Was I supposed to take the job? Am I about to suffer from major biz building FOMO? I don’t think so. For one thing, the process taught me a great deal about my capabilities, my potential, and about what I really want from my career. It forced me to nail down exactly why I’m doing what I’m doing, whether or not I truly enjoy it, and whether or not a steady paycheck outweighs the somewhat idealistic pure and simple love of work.

To this day, two weeks into a dry desert stretch of no projects, I don’t regret my decision. When I consider that I could be busting my hump to complete 35-40 hours of direct marketing copywriting on someone else’s timeline, feeling underpaid and unappreciated, I’m glad to sit here in this dark hole of forgotten writers awaiting my next big break. Despite the rampant fear and stress present in the wait, here’s also a strange hopefulness in it. My future has yet to be written. I’m still a wild stallion. Nobody can saddle me with months’ worth of projects and dictate how I proceed – at least, not until I say so.

I think at some point in every entrepreneur’s journey, they begin to look back and wonder if they’re better off in relative “safety.” That can mean something different to everyone. To me, safety is apparently a 9-to-5 job where the pay is steady, the ladder upward is somewhat clear, and the workload semi-predictable.

It felt like a milestone, coming face to face with the opportunity to go back into the fold and to resist. It helped me realize that safety isn’t worth compromising the life I know I can build, if I give myself half a chance (and happen upon a little bit of luck). It also helped me recognize that nowhere is truly safe – you can lose a job, or worse: spend your life chasing after other people’s goals at the expense of your soul – and end up no better off than someone who took a more circuitous route.  

Perhaps, at some point, a full-time job will feel like a good fit for me. Maybe when I’ve tried every way I know how to build a business and gotten absolutely nowhere. Maybe when the clients seem horrible and the work feels boring. Maybe when I decide the risk doesn’t feel all that exhilarating anymore. Maybe you’re reading this right now and shaking your head at what a complete idiot you think I am.

Okay, maybe I am. It’s quite possible that I just took the biggest gamble of my life without even realizing it, only to spend years wandering the desert – a big, dumb stallion fueled by dreams of lush prairies I may never find.

Today, I’m not terribly concerned with the future. My task is to walk this path, step by step, working hard and keeping alive the hope of many Golden Moments to come.

And, with any luck, I’ll find them.

Wanna carpool with me on the highway to “success” (whatever that means)? FOLLOW MY BLOG (scroll to bottom and click) for regular installments of the “Self-Annoyed: Solopreneurship Done Write” series, and let’s feel every shred of the crazy/ excited/ terrified/ badass together.

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