An abandoned gas station says “Welcome to Port St. Lucie, Fla.,” an indifferent choice of locale for a first job. (Photo: Rob Colonna)

Cambridge Day is part of a project called Voices of MainStreet — a weekly, nationwide Q&A in which editors at the money and lifestyle site MainStreet.com ask questions and bloggers answer them. For this entry, I was asked about lessons from my first job.

My first job out of college taught me so many painful life lessons that thinking through the period is like watching all of BestWeekEver’s March Sadness bracket of the 64 saddest movies spliced together with the British “The Office” — except on fast-forward, because the entire experience lasted only four months.

There is the occasional lesson that wasn’t superlatively sad and awkward, although the one about eating jalapenos naked is unfortunately unspeakable. On the whole my self-imposed sentence in some of Florida’s least interesting cities seemed almost crafted to do what four years in college could not: teach an arrogant, careless, emotionally void young man he couldn’t pull off any of the three.

I left Boston with a cat, an attitude and not much else in a top-of-the-line used luxury car and in the blink of an eye had lost my cat and attitude and was taken to the heights of helplessness and hysteria by what seemed continual tire blowouts. (Life lesson No. 1, I guess, would be that cheap tires are not worth it. At all. Don’t keep replacing cheap tires with other cheap tires.)

How not to choose a workplace

My very presence was a mistake, a very literal mistake. Upon graduating journalism school in Boston, I decided I could get a job at a daily newspaper — look it up, kids — by playing the odds. The theory: If I applied to every daily in a specific place, surely one would come through and offer me a job. That’s pretty idiotic, but I figured out a way to make it even stupider by, I am not kidding, applying to every daily newspaper in Delaware. I didn’t want to be there, but it’s a very small state, and that meant less work applying.

It was an astonishingly whimsical notion for an era when it actually cost postage to send a resume, but it shows I was willing to go literally anywhere for a job, because starting my career was all that mattered.

When Delaware failed, somehow, I sent resumes to every daily newspaper in Broward County, Fla., which was especially appealing to me for its crime, corruption, sleaze and silliness. At the time, rap group the 2 Live Crew was not only banned there, but arrested on obscenity charges while performing there. Immediately afterward the county became known as, um, a flashpoint in the banning of thong bikinis from state beaches. For obvious reasons, I was thrilled to be hired by a newspaper near all the action and even more stoked to be the only one among the journalism grads to get a job at a daily right out of school, especially in such a bad economy. (Who knew? Every factor in this story is worse now.) I bought that car and drove down.

Much to my surprise, I learned while mapping my trip that the newspaper that hired me wasn’t in Broward County. It got added to my list, apparently, by mistake.

And that’s why I was in such trouble there. I didn’t check my facts.

How not to keep a job

The reason the paper had to run so many corrections for my stories wasn’t just that I was arrogant. Mainly it was that I was shy. I couldn’t take notes quickly enough to keep up with what people were saying and I was embarrassed to ask them to slow down, repeat themselves or clarify later. It didn’t help that failure compounded failure and I went through each workday with a searing bubble of panic in my chest. It’s hard to concentrate when you’re scared and nauseated, and that made me even sloppier.

I am to blame for this. My lack of rigor resulted from sticking so close to my tiny college campus, the little life I knew so well, instead of fighting for internships and freelance jobs that would have revealed my weaknesses and forced me to deal with them. I could have apprenticed myself to professionals who wouldn’t brook the amateurishness, but instead I clung to peers who knew no more than I did and teachers who gave me grades I could shrug off, not paychecks I needed to cash.

First the Florida paper told me I was in a trial period and technically didn’t have a job. Then I was told the trial was extended a month. Then I was told I wasn’t getting the job. I was happy to hear it because it meant I could run away, even though at the end — feeling much less pressure — I got over myself and did better in my work.

I had gone to Florida thinking I could leave behind my culture, friends, girlfriend and family to launch a brilliant career, but I failed at all of it. I fled back to Boston, to all those people and to start my career completely over, and strangely, much of that career has been as a copy editor obsessed with the most niggling details of reporting the news.

Lessons, kids? Well, first there’s that bit about cheap tires. But more important is that when you get that first job, the only thing that counts is doing it well. You may have to get over yourself, or your fears. And if you’re still in college, get off campus and start your career before you have to.

Also, family and friends count for more than you’d think, which is another lesson you’d learn from a lot of those movies I mentioned. My four months of failure has saved you 64 films worth of weeping.