Sunday, August 16, 2015

8/17/15—Becoming Peggy Olson

Everywhere I looked this past week, it seems I was being reminded of the story of how I became a freelance advertising copywriter. Like many things in life, it all began with a crippling rejection. 

But first things first. An advertising copywriter is the person who writes the ads, brochures, mailers, TV commercials, websites, etc. that you see all around you. Think Peggy Olson on MadMen. It's a really creative job, because you're not just writing, you're thinking up the big-picture concepts (usually in partnership with an artist.) It's also really strategic, because there are certain parameters you have to work within—what is the client trying to accomplish and say? Who is the target market and what are they about? And what is the brand personality you have to adhere to? You can't just come up with a creative idea and go for it. No matter how "out of the box" your idea is, it still has to fit in a box. 

I remember reading a book in my early 20s about how to get a "glamour career", and copywriter was one of these careers. In reality, it's not as easy breezy as you would think. For one thing, the creative department gets none of the glamour in advertising (if there even is any glamour in advertising at all.) For another, it's high pressure, with daily deadlines and terrifying, ever-present expectations of brilliance. And since "brilliant" is a subjective term, you have to know what brilliant means to the people in power—the clients and creative directors who edit and judge your work. Finally, you can't just be creative. You have to think about marketing strategy and communication strategy and psychology and budgets and selling your work in big meetings and all kinds of stuff. 

But hey, that's what I wanted. So it's what I went for. But it's not easy to get one of these jobs. Unless you're talking about the very largest big-city agencies, most agencies might only have one or two writers on staff. So the jobs are few and far between. In fact, it's easily the hardest job to get in advertising when you're just starting out. As a result, I began my career in the creative department, but not doing anything creative. I was a traffic person, which is an administrative position, moving work through the agency. 

I did that job for three years, trying to break into copywriting the entire time. In an odd twist of fate, something I wrote "on the side" back then ended up earning one of the most coveted awards in the industry—a One Show award

This accolade got me a job interview at a place called Britches. Britches was a hip, cool, growing retail brand. They had an in-house advertising department, instead of an advertising agency. And while the vast majority of in-house advertising departments feature soul-sucking jobs, a slave-driver culture and zero potential for creativity, Britches was different. They were every creative's dream, mine included. 

My vision at that time in my career was that I would eventually become a creative director. Having a place like Britches on my resume could help make that happen. It was, in my mind, the best job in all of Washington, DC for a writer at the time. It could open up doors at Richmond agencies, which, in the '80s, were some of the most creative and award-winning shops in the world. And from there, I could go anywhere, do anything. 

Everything was riding on this interview. 


Well, I didn't get the job. I was devastated. Devastated. I remember laying on the floor of my apartment, crying my eyes out the night the rejection letter came. My career was over! I'd have to leave town or, worse, become an account executive...or, gah!, a media buyer! ;)

I eventually got a job writing in-house at a lesser retail chain, and then another even lesser retail chain. Remember those soul-sucking jobs I was talking about? Well, the second of those two jobs definitely fit that bill. After that, I got a job at an advertising agency with a good, strong reputation in the marketplace. So that was good. Then one thing led to another and I got tired of being underpaid and under-appreciated. So I set out on my own, even though it meant I'd probably need to leave my dreams of being a creative director behind. 

The four jobs that I had in the first 10 years of my career each gave me valuable gifts, primarily in terms of contacts. Two of those jobs yielded my two biggest clients—clients I've maintained pretty much throughout my 20-year freelance career. The last job gave me rare (at the time) subject matter expertise in the technology industry, which I parlayed into to many lucrative years during the high-tech and dot-com booms. I'm now someone who is fairly compensated and well appreciated, a blessing I am constantly grateful for. I've certainly had some bad years along the way. I've also had some bad experiences. But both, thankfully, have been few and far between. 

Best of all, my lifestyle is such that I can pursue my spiritual path, blog, create card decks and, from time to time, play professional psychic. I spend each and every day in undistracted silence, surrounded by three adoring dogs. And I can write books and pursue my future career as a spiritual self-help guru anytime I want during the workday, so long as I'm responsive to clients and meet all my deadlines. I would not trade my life right now for anything else in the world. 

Had I gotten that job at Britches, however, I would not be where I am today. I would have gotten on an agency track quicker, hopping from job to job. I would have learned better politics in better places. I would probably have at least 10 years as a creative director under my belt. I'd command a hefty, six-figure salary at a good agency in some city somewhere. I'd work 10-12 hour days. I'd have a coiffed 'do and respectable clothes. And you know what? I'd be really good at it. I'd totally go all Peggy Olson on that shizzz. 

But had I gotten that job, I would absolutely be a different human being. Without a doubt. I would never have had the opportunity to delve so deeply into my spirituality. I would have never had the time to create fortune-telling decks. Or blog. Or become a published expert in an art as complex as tarot. I probably wouldn't have three dogs. There's a lot that would be different, because that kind of life comes with certain lifestyle and personality requirements, some of which would benefit today's me and some of which, after 30 years in the shark tank, would have turned me into someone that today's me probably wouldn't like very much. 

Back when I interviewed at Britches, I had a passion for making an impact on others through advertising. I still have that passion, but it has, admittedly, waned over the years. However, in its wake, it's leaving me something even greater than passion. It's leaving me a mission. A mission to write and make a more soul-affirming impact on the world. I think if my career had gone the other way, I'd be left with nothing more than that waning passion, a considerable sleep deficit and unsightly stress sores.  

Turns out that night I laid on the floor of my bedroom crying was the luckiest night of my life. 

And that soul-sucking job I had? It netted me not just a good friend, but a long-standing client with whom I've done some of the work I'm proudest of in my career. Because of her, I've had a hand in creating some of the most lauded brands in the higher education marketplace—Maryland's Fear The Turtle and American University's WONK. In fact, the Fear The Turtle campaign was instrumental in redefining the landscape of higher ed marketing altogether, more than a decade ago. No matter where you work, those kinds of opportunities don't come around often, if at all.

Sometimes, even when you're eating glitter, it's hard to spot the sparkles in the shit. And sometimes it takes nearly 30 years to see the wisdom in the very thing that devastates you. But the wisdom is always there. It's difficult to see why something so painful to the human is so right for the soul. But if you hold enough space in your heart for the answers, they will eventually come. 


  1. Amazing, isn't it? I'm sometimes asked what I most regret in life, and I can honestly say "Nothing!". What point in regrets? I am who I am because of everything that has happened in my life, and I love who I am. Yes, I could have been someone totally different, or maybe I would have come round to this place via a totally different route, who can say? What I know is that I can find joy in where I am now :)

  2. I am so much like you in that regard! I can't even wrap my head around regret. It doesn't make sense to me. Regret is "I wish I could go back and make a different choice" or "I wish things had been different", but neither of those things are possible! So each time I set down that road, I can't make it very far, because my sense of logic overwhelms me. :) I consider this a special power I was given, because people get really stuck on regret and it has no power over me. That said, there's plenty of other stupid stuff I'm more than happy to get stuck on...haha.