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The Free(lance) Life, Reflecting on Year One

My good friend, an owner of a successful business, recently asked if I’d ever consider going back to an agency full time.

I shook my head. “Nope.”

He pressed on. “Not even for another creative director role?”


“Is there a certain number you’d go back for?”


You’d think that last question would be a toughie. But truth is, going off on my own has been nothing short of a revelation. Even with all the uncertainty of being out in the wild, I’ve never been happier in my career than I am now. Would I sell that happiness for a quarter million dollars and an excellent bonus package? What’s my happiness worth in US currency? It’s not a tough question at all. Both my wife and daughter would back me up on that. In general, they see a less stressed, more purposeful, more open-to-change version of me every day. Now, I’ll be the first to admit that if someday freelancing stops covering the bills, I’ll dutifully reconsider my stance.

So, it’s been a year. A year of reconnecting with my network. A year of seeking out new opportunities. A year of recalibrating my definition of success. All in all, it’s been a year I’ll not soon forget, one that clearly stands apart from any other in my advertising career. It got me to reflecting.

For two and a half decades as a full-time employee, I found myself feeling captive — trapped by meetings I didn’t schedule, deadlines I didn’t promise and goals I didn’t set. But my undying loyalty and my unyielding sense of responsibility always kept me there, churning away. I’d forego running important personal errands in fear of the possible optics. I’d martyr through multiple projects when I should’ve taken one of many unused sick days. And worst of all, I’d spend many nights lying awake, stressing over ridiculous office politics. It wasn’t until I realized I was my own captor that I was finally able to break free.

Now, my days are mostly on my terms. I can be as busy or not busy as I want to be. I don’t have to put off household duties and errands until the weekend. I read and listen to more news than ever before. And though I have a perfectly lovely office at my disposal complete with a power standing desk, I choose to work on the living room couch, near the fireplace, with my feet up on a Moroccan pouf. Not ideal for my posture, but sure does wonders for my spirit.

Though adapting to my newfound freedom has been rather easy, finding work can sometimes be a challenge. Seems agencies aren’t always in the market for freelancers, so I’ve had to track down some clients of my own. I used to dread new business because it meant days and nights of pitch work and high-pressure presentations. And even if we won, there was no guarantee we’d be staffing up to accommodate it, which meant more client work piling up on my already full plate. Today, working for myself, I see the value of pursuing new business, and I welcome every new prospect, every opportunity and every win with open arms.

When I decided to go freelance, one thing I thought I’d be leaving behind was the chance to win industry awards. I suspected I’d be assigned the projects that would keep the mill turning, allowing other agency writers to chase the sexier work. But during this first year, I was honored to help two local agencies take home awards at The Show. They were humble recognitions to be fair, but entering work – much less winning – hadn’t even figured into my early expectations. This experience has helped shift my mindset moving forward. As it turns out, becoming a freelancer didn’t suddenly make me a second-class creative, so I simply can’t sell myself or my work short ever again. That should prove beneficial for both my career and my self-esteem.

Now, as the Year One sheen fades away, I ponder what’s to come in my sophomore year. The way I see it, as the novelty wanes, so does my margin for error. Freelancers are easily forgotten, so I need to keep getting better at my craft and at connecting. I need to cherish and celebrate the ups, while refusing to let the downs break my spirit. Most of all, I need to keep reminding myself that happiness is an endless pursuit, and that it can never be measured in material things.

Back to that conversation with my friend. Eventually I turned his question back on him. “What about you, would you ever give up being the boss?”

He shook his head. “Nope. You’re doing the right thing.”

Welcome to my workspace. 100% warmth and comfort, 0% weird office politics.

#freelance #copywriter #copywriting #advertising #bestlife #selfemployment #freedom #boss