ter law school, I started working for a
large New York firm, Simpson Thacher &
Bartlett. Because I had some interest in
property law and zoning, I found myself
doing real estate and corporate work.
How did you decide to leave the law?
AC: Simpson Thacher was a great firm
and I had an excellent time, but I realized
pretty quickly both that the practice of
corporate law, and the traditional practice of law in general, really weren’t for
me. There’s the old line that becoming
partner at a law firm is like winning a
pie-eating contest and the prize is more
pie. I looked into the future and thought,
“I do not want to eat that much pie.” So I
figured I would just cut my losses.
Around the same time that I concluded
that I didn’t want to be a partner, I also realized that I wanted to be a writer. So the
question was not if I was going to leave,
but when. I was only at Simpson Thacher
for 15 months so my transition probably
seemed abrupt to some, but it wasn’t for
me. I had already been planning to leave
for three to six months.
Was leaving scary? I know many lawyers find that to be a difficult transition.
AC: Leaving was a bit intimidating. Of
course I was concerned about paying
off student loans and how I was going to
make a go of being a writer. However, I felt
good about my choice to leave because I
knew the longer I stayed, the harder it
would ultimately be to go. There’s sort of
a “golden handcuffs” issue.
More generally, however, I think that
So, as you prepared to leave, what were
lawyers are a particularly risk-averse
lot. This is borne out partly in the fact
that you went to law school: you worked
hard to be able to have the privilege
of doing the safer, more conservative,
thing. But also in law school and prac-
ticing, you hear about all the horrible
things that can happen. You’re always
supposed to think about all the worst-
case scenarios. I think that you’re sort
of prevented from looking at the upside
of things and taking chances.
your plans and how did you land?
AC: I was definitely concerned as I prepared to exit the law firm. When I left
Simpson Thacher, I took a pay cut of
over 50 percent. I moved into a smaller
apartment and budgeted in other ways to
make sure that I had enough to live on for
a while. I was nervous but optimistic that
I could find something.
And you did find something.
Yes. Who Wants to Be a Millionaire?
started in the summer of 1999 with Regis Philbin as the host. At some point
they realized the show had larger potential, so they put out a call in New
York for game show writers. To my
advantage, there were no game show
writers living in New York, and there
hadn’t been a game show produced
here in decades, so anyone could apply.
I applied and I was fortunate enough
to be one of the first writers hired on
the prime-time show. The funny thing
is that when I signed on they said that
the contract was for only five weeks; I
wound up working there off-and-on for
almost 10 years, and it’s led to jobs on
other shows, such as Cash Cab, The
World Series of Pop Culture, and Stump
the Schwab. Currently, I’m the puzzle
editor and one of the on-air “puzzle gurus” on the National Public Radio show
Ask Me Another.
To date, Who Wants to Be a Millionaire?
is probably your most well-known cred-
it. What did that show teach you?
AC: That lawyers like to be on televi-
sion! We had so many contestants who
were lawyers. I think that the reason is
twofold: First, lawyers know a lot of trivia
and, second, they want to show the world
that they know a lot of trivia. And also,
lawyers like to complain when they get
knocked off the show.
Has your legal training helped you in
your professional path and, if so, how?
AC: Absolutely. I regularly use my legal
writing skills to make sure that I write
and think clearly. Also, you wind up getting into arguments that have a very legalistic flavor in trivia. It’s helped me to
keep my thinking sharp — and also to win
some of those trivia arguments.
Any advice to lawyers who are interest-
ed in becoming writers or game show
AC: If you’re an aspiring writer, I would
say to just keep writing. Throughout my
time at Yale and in law school, I spent a
lot of time writing for the school paper. As
I mentioned, when I was in law school, I
also wrote for Time Out New York. By the
time I was preparing to leave Simpson
Thacher, I had a portfolio of written work
that I could show to potential employers.
Today, you may not even need to seek
out opportunities for formal publication
— you could just maintain a blog writing
about your passion.
Second, take a chance. Lawyers can
be too risk-averse. Your training and
maybe even temperament make you
inclined to see a downside in a lot of
choices, but there’s never a perfect time
to make the jump. NWL
Dan Lear is an attorney in Seattle.
He maintains a business and technology advising practice at Ragen
Swan PLLC. He is active in various
groups thinking about the practice
of law, legal education, and lawyer
professional development. He blogs
com and you can follow him on Twitter, too: @rightbrainlaw.
I regularly use my legal writing skills to make sure
that I write and think clearly. Also, you wind up getting into arguments that have a very legalistic flavor
in trivia. It’s helped me to keep my thinking sharp —
and also to win some of those trivia arguments.