G Sharp Turns One!

Reflecting on the Rigors and Realities of Self-Employment.

Almost two years ago I asked my then-fiance / now-wife, “How would you feel if I left [a pretty darn good full time] job to start working for myself?” She didn’t hesitate in her support of this ambition, and I want to begin by saying how much that mattered to me. I never would have gone for it without her vote of confidence. So I researched and planned and socked away savings and a year later—which is now a year ago—G Sharp Design LLC opened for business.

Since then I’ve completed about 160 projects of all shapes and sizes for clients in 21 US states and 8 different countries. Books, magazines, logos, coffee bags, event posters, album art, company signage, marketing materials, websites and plenty more beyond. It’s been an enriching and validating experience, but not an easy one.

I’d dreamt of a freelance career since my days as a design student, but I didn’t quite see the whole picture. Back then it seemed like the Promised Land. The golden pasture you reach by paying your dues in the 9-to-5 world. Once you’d found a way to support yourself on your own terms, the velvet rope is unlatched and you cross the threshold into a Bohemian Dreamscape. No more company meetings or bureaucratic parameters! It was all coffee shops and sleeping late and a simple transactional business model—I do the work, you pay me, we both go home happy.

I quickly discovered that running a practice was every bit as challenging as full time employment was, if not more. Even a dozen years removed from college, there was still a part of me that thought it wouldn’t be. One of my first clients, a fellow solo act who works in the coaching/speaking realm, told me, “Get ready to work harder than you ever have,” and I sort of pegged it for a platitude. How would I work harder? I found the Promised Land!

And there really are so many great things about it. But much of what I considered a luxury of self-employment was more of a reality. Yes, you get to be your own boss. But unfortunately this means you have to be your own boss. Turns out your boss does a lot of stuff. So do all those other departments in your company. It all falls on you.

Spinning All the Plates

A distinction worth making is that freelancing itself is easy. Earn a hundred bucks a month on odd-jobs and, hey, you’re technically freelancing. However, maintaining a livelihood while issuing meaningful work, keeping yourself on task, and managing all the corners of your business is decidedly not easy. That’s the big message I try to get across to anyone who says they’re also interested in exploring self-employment in a creative field. There are many great things about it, especially at the onset. But prepare yourself for the many plates that will need spinning.

Back when I was working as the creative director at my old company, I interviewed a job candidate who was prepared to pivot out of freelancing after a decades-long run. His reason: “I’d rather be working than looking for work.”

He didn’t mean to say that his opportunities had dried up. He meant that a dedicated, full time graphic design role had become more attractive than the steady rigors of managing a solo practice. The status meetings and commutes and business casual dress code were now all preferable to the demands of client outreach, sales calls, project management, bookkeeping, personal marketing, and countless other ancillary responsibilities of the sole proprietor. Interestingly enough, it was simplicity that was drawing him back to the 9-to-5 world. Simplicity: the very factor I was citing as a reason for setting off on my own.

Making the Right Call

I could argue that G Sharp actually has been simpler in some ways. But in other ways it’s invited a layer of complexity into my career, which I suppose was to be expected. The most drastically increased factor since moving from full time to self-employment? Unpredictability.

Office life is supposed to be predictable. I did it for almost 12 years, and while curveballs abounded, part of the allure of a full time job is structured rhythms that make your job and life a bit easier to manage. Direct deposit every two weeks, a benefits package, a clearly defined schedule and job expectations. While every 9-to-5 job calls for some degree of flexibility, there is comfort in having a specific role. I was deeply ingrained in that state of being, and reprogramming myself was something I struggled with in the early going.

Now, unpredictability is an expectation that calls for a sharpened sense of foresight, adaptability, and opportunism. Part of the job is reacting sensibly to the challenges that will inevitably present themselves.

The good news: I get to decide how to confront these challenges. A year ago, I might have considered this bad news. In a way, that shift in perspective is why the last year’s been worth it to me.

And it’s why I can’t help but be excited about the future.

* * *

I’ll close out by thanking everyone who’s worked with G Sharp Design in the past year. It’s truly humbling for your idea to be recognized as a resource. I’ll also thank anyone who said, “You should do it.” That includes my wife, parents, in-laws, friends, and even my former bosses and colleagues when I informed them of my plans. Whatever confidence I have is simply a function of the confidence people had in me.

The decision to leave a comfortable job to start from scratch was not whimsical or rash. It was predicated on many discussions with trusted peers and mentors, reading books on small business finance and management, on a careful and objective analysis of my family’s ability to run on a severely reduced household income for a period of time. This isn’t to say there was no risk involved, but I sought to mitigate as much of it as I could before factoring in answers to the major rhetorical questions: Am I capable of pulling this off? Will people want to work with me? Will I be happier? So far, at least, the answer appears to be yes.

And now, off to start year two. I’ll let you know how it goes!