It’s a year and a half since I left my last job, left meetings, left acount executives, left downsizing, left that tight feeling between my shoulderblades. For the next year, I managed to do a lot of drawing and travelling. I created this blog, worked on the staff of the Morning News and the New York Times, and finally achieved my dream of being paid to be an illustrator. I finished one book and then conceived and wrote another, the book I have always wanted to read. I spent a lot more time with the people I had abandoned during my four years of senior management: I picked Jack up from school, I sat in the kitchen and talked to Patti every morning, unencumbered by bosses and office gossip. I met hundreds of great creative people around the world. A happy time.
Somewhere in the back of my head, probably on a nerve that connects right to that tightness in my shoulders, a little voice continued to murmur. “You’ll never make enough money. You’ll never be able to afford the standard of living you had during all those years in advertising. You are still a rank amateur. What will you do when you’re sixty? Seventy? What if you live as long as your grandfather? You can’t survive to 95 on scraps. Wipe that smile off your face.”
On and off, I freelanced in ad agencies. I had steady clients who brought me back in time and again. In one day of advertising freelancing, I could make what took me a couple of weeks of illustration and so I did both.
And I enjoyed it. I enjoyed it like I hadn’t in years. I was being hired just to sit around and come up with ideas, to make things. Not to hold clients’ hands or draw up lists of people to fire or listen to my boss quote from his most recently read book on management techniques. All they wanted was ideas and I have become a fire hose of those. At the end of each assignment, I would throw on my suit and present the work to the client and most everything was well received.
Then last summer, just before I went on my cross-country trip, I came up with a campaign that won a small agency an account worth about a quarter of a billion dollars. When I finished my trip, visiting Andrea in San Francisco, I got a call on my cellphone while walking down Market Street. They wanted me to come back and run the account.
It was exciting to have been part of this sort of victory. We had beaten the biggest, most famous agencies in the country, based on a line I’d thought of at the urinal one afternoon. The agency has done a lot of good work and it is on a phenomenal wave of success. Right after the big win, we reeled in one of the leading sneaker companies, then an international beer, and now we are on the verge of three other huge new accounts.Our success is like nothing in the recent history of advertising and there are just a meager overworked handful of us doing it.
Like the tsunami that hit Asia, this agency’s momentum has threatened to devestate all of the changes I made to my life over the past couple of years. It is easy to succumb and work sixteen hours a day, seven days a week. I can give up this blog, see my family only in their pyjamas, stop drawing altogether.
I can also succumb to the tension and fever pitch and not even enjoy the incredible creative opportunities on my plate. I just got the go-ahead to shoot a dozen commercials, each with a budget over a million dollars. I’ll be traveling around the country to do it and yet I can still make myself feel miserable about it. Miserable because I worry about what I am losing, breaking my commitment to myself. Miserable because I can worry about not living up to expectations. Miserable because I’m an ad guy again.
It has been a struggle not to succumb. I know that sounds dreadful and there are so many people who would do anything to be in my place. What I am wrestling with, truely, is the danger that I could slide back under the waves, go back to how I felt a half dozen years ago, when I didn’t draw, didn’t share my feelings, couldn’t conceive of myself as an artist.
But guess what. I can and am and will continue to win that battle. I am not the person I was. And even though I am in the world I left, I am a new man. My year off was transformative. My imagination works better than it ever did. My confidence and self-knowledge are magnified.
If you are considering chucking a job or career or a direction that stifles you, I hope my experience is helpful. You can decide to walk away and then to walk back without feeling like your experiment was a failure. You will return, if you do, changed and smarter and knowing where the exits are in case you feel like you need fresh air ever again in the future. Or perhaps you will stay on the new path and never look back. All that really matters is that you take each day as it comes, look for the beauty in it, abandon preconceptions and focus on what you want to be. A healthy, creative, complete person.
I wish it for you. And for me.
Danny Gregory 
Wow!
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