The Art of the Gamble


Don’t ignore opportunity, but definitely play hard to get.
By Elizabeth Cutright

I am not sure if I’ve told this story before. During those first years after law school, I struggled to find gainful employment as a writer. Because most of my experience at the time involved school newspapers, I focused on journalism. Most of my interviews went nowhere fast – you’d be surprised how many employers view a JD with suspicion (they wonder why you aren’t off making millions suing tobacco companies I guess) – but a lucky few produced some freelance assignments.

For about a year, as a part-time gig, I wrote about school board meetings and country regulations and the occasional rally or political protest. I think I earned about $35 a story (the first check arrived in my mailbox with a sticky note from the editor, “Don’t spend it all in one place!”).

While I toiled away at my day job, I picked up assignments whenever possible. I also pitched and queried and sent a resume to any employment listing that seemed mildly related to writing. I tried to apply to one job per week, which meant thinking outside that proverbial box and sometimes gambling on whether or not an hour or more commute was in my future.

But this post isn’t about my employment struggles. It’s about the opportunity: seizing it and letting go. As Kenny Rogers once wisely rambled, “you’ve got to know when to hold ‘em, know when to fold em.”

Sometimes you have to walk away (sometimes you have to run), and other times the hardest thing to do is stand your ground and make the case for your cause.

My first opportunity came about six months into my freelance journalism stint with a local weekly paper. A new publisher was on the scene, and he’d asked the editor to provide him with a short list of potential staff writers. I got the call for an interview, and over coffee, I was asked about my ambitions and my vision regarding the periodical and journalism in general. Without actually meaning to, I inadvertently pitched a series of investigative pieces on homeless in our community. The publisher loved the idea, and before I knew it, I’d agreed to the assignment.

I was, of course, in waaay over my head! I’d taken a sociology class that had discussed homelessness. I’d interned at the public defender’s office in my youth as part of the mental health assessment team, and so had some knowledge of how mental illness impacts homelessness. I even had a contact with the Sheriff’s department.

But I was scared. This was a big project. Success would mean a full-time job as a journalist with a promised salary well above what I was making as a legal document processor. Failure seemed destined to doom me to a life of office drudgery.

It felt like a “make it or break it” moment, and I crumbled under the pressure. I never wrote a word. I never conducted an interview. I never returned the publisher’s calls. I just melted back into the anonymity the like those ghosts returning to the corn fields in Field of Dreams.

For a while, I was devastated. I felt as though I’d turned my back on opportunity. I felt like that was my one shot, and I’d missed….spectacularly.

It was rough going. Eventually, I just got back to the business of living and writing. I kept up my morning pages. I slowly started looking at the want ads. Eventually, I mustered up the courage to send out resumes, and all the while I gave myself pep talks about the nature of ambition and the capriciousness of timing.

The second time around, I went on a couple of interviews and was quickly offered a position at a real estate start-up looking to create a presence on the web. The basic nature of start-up requires most employees to work for pennies (often with no benefits) and gamble on eventual success and million dollar stock options. I have friends of friends who anted up and one big, working for the likes of Microsoft, Google, and Yahoo. Of course, they young and just out of college at the time – which is the perfect moment in life to embrace poverty wages in the hopes of a better future.

It’s a little harder when you’ve got law school loans, a car payment and dreams of going to the dentist without having a panic attack. So I considered, and I bargained, and I strategized.

And in the end, I declined. To say “yes” would have meant a 20% pay cut on my already measly salary, and that was a hardship I could not shoulder. It was hard to say “no”; the start-up team was so full of enthusiasm, they seemed destined to succeed.

But scary as it was to turn my back on opportunity yet again, I had to suck it up and walk away.

About two weeks later I got the call for a staff writer at a national publication and thus began my editorial career. By saying “no” the “not quite perfect” situation, I’d left myself open for something better.

It’s a balancing act – the “yes” the “no” and the “maybe.”

Just remember, as Ralph Waldo Emerson advised, “Heartily know…When half-gods go…The gods arrive.”

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