Appreciative Reflection – Copywriter
Bill Cavanaugh, another project participant, has been talking about his friend Sheryl who
has been working on major national accounts as creative director and copywriter for as
long as I can remember. It kind of became a joke when I asked Sheryl to be a participant in
this project even though we had never met before. Every time Bill would say, “my friend
Sheryl.” I would respond, “you mean MY friend Sheryl.” After we finally met and had our
conversation – I can honestly say she’s MY friend too.
Sheryl is one of those rare people who operated primarily as a freelance writer for more
than 35+ years in the highly charged New York City advertising arena and that is nothing
short of astounding. Sheryl used to commute from her apartment in Manhattan to her
home in Woodstock every weekend to decompress. In the last few months, she has given
up her New York City apartment and has migrated to the quieter area of Woodstock, New
York and continues to work as a copywriter in her rustic cabin-like home in the woods.
Although the stress from living in the city has somewhat abated, the demands of making a
living in the advertising industry are still there.
The 35+ Year Freelancer – Embracing The New
Sheryl is candid about her career, “I started at a major global ad agency in Ohio as a junior.
I was there about six months and they decided to close the office. I was in Cleveland and
everyone was moving to New York and I wasn’t -- so I flew myself to New York. It’s kind of
like the show ‘Mad Men’ -- everybody smoked, drank, and all the people in charge had
three-hour lunches and came back ‘shnockered.’ I didn’t last long there because my
drunken boss didn’t like me. I was forced on her basically. I got fired and that was a real
wakeup call. It was my first job. So I started freelancing for the next ten years. I would go
from freelance to staff jobs – because a company would force me to take a staff job
because of some laws or whatever. I always preferred freelancing because if you don’t like
it you leave. You’re always on to something new -- and always meet new people. You
have a bit more autonomy -- not a lot. You work a lot harder when you’re freelancing.”