Inspired by BlackBerry, Gawker commissioned former staff writer Richard Lawson to relay his boldest experience, and here it (they) is (are). Read his original, Northeast-spanning essay below to discover how '90s pop-punk outfit The Offspring and Menopause: The Musical altered the course of his life.

Talking about a bold thing I've done, something that's changed me, is hard. First off, crowing about our own boldness feels sort of arrogant, doesn't it? Obviously we're all the decided heroes in our own weird myths, but those legends are mostly kept quiet within ourselves, kept spirited and secreted away, only rarely spoken out loud while perched on bar stools or a therapist's couch. And second, we're usually so unaware of our own boldness when the actual act of boldness—or daring, or courage, or whatever—is occurring. So to try and sift through my own meager personal history and siphon out some good story about how I stepped boldly outside of myself and won in the end requires a somewhat depressing bit of self-analysis; it's easy to start to think that I've never done anything bold, that it was all just stuff I did once when it seemed like the right thing to do.

But of course I'm probably shorting myself. I have acted boldly! I have emboldened myself! When I was in sixth grade, I, with considerable goading from my friend Rob, publicly confessed to the deep, queasy ache I had in my heart for a girl named Alicia, whose best friend Rob was "dating" at the time, whom I was sort of forced into loving so we could, the four of us, become the perfect, square double couple. And do that I did, rather amazingly in hindsight, one day at recess—walked straight up to Alicia in front of her friends, told her I needed to talk to her, and under a tree in Newton, Massachusetts told her I liked her. I was bold twice more with her, giving her a birthday present (an Offspring CD, ugh) and a Valentine's Day gift right in the hallway for all to see. But I'm not sure that really qualifies, as that had probably more to do with social pressure than with some innate, sudden fire within myself.

I somehow, a few years later, found the boldness to audition for school plays. Though I continued to do so all the way through to senior year of college, which wasn't that long ago, the idea now that I used to, somewhat regularly, stand in front of friends or strangers (more than likely friends, but still) and do a whole monologue is pretty crazy. And that I would then, providing there were good results from the audition, go on to perform a play in front of an audience full of people, well that just seems insane. I guess that was bold of me, but again with the social stuff, I was joined by cast mates, by fellow auditioners—I was part of a team. Boldness in numbers counts, but probably not for this assignment.

So I think I'm going to have to say that, cheesy and simple as it is, the time in my life so far that I was boldest was when, a month after being laid off from my job and moving back to my parents' house on my birthday, I packed up the little details of the life I knew and left Boston for the first time, headed to New York on July 4th, 2006, winding into town on a bus and pretending that the fireworks fizzling over the river were all for me. I had just accepted a job three days prior, had nowhere to live, only knew a handful of scattered people in the city, and, as mentioned, had never really left Boston. The longest I'd ever been away from home was six weeks. But this new adventure was promising, if it worked out right, to be forever. Or at least as much of forever as a 23-year-old can imagine. Most importantly for the boldness of this, I was doing this by myself. My sister wasn't coming with me, my parents were only half-supportive (they encouraged me, they just thought I was crazy to do it like this, with so little planning), and, again, I had nowhere to live.

I was lucky enough to have a friend, a former coworker from Menopause: The Musical in Boston, on whose couch I could crash, so I at least had a place to lay my head. I know this doesn't sound terribly dramatic, or terribly bold (maybe it even sounds easy), but for a kid who tried valiantly his whole adolescent life to assert that he wasn't sheltered to put his money where his mouth was and actually prove that he could hack it in the bohemian circus of New York was, the more I think of it in ensuing years, pretty big. For me, at least, it was big.

And it worked out! Here I am writing a thing for a thing about this thing I did once and I had no idea or dream, even, that that could possibly happen as I sat on that bus almost six years ago and watched Connecticut yawn by. All I knew was that one day I woke up in Boston and I'd go to sleep in New York, and thus would begin many other nights of the same, thus would begin the long and strange and often very difficult process of taking my little paws and carving out a new home. I know this story is shared by lots of people, in different cities in many different places, so to that end I'd hope that we can all appreciate for ourselves just how bold we were—to leave home, to strike out, to do all that stuff that the Dixie Chicks sing about in "Wide Open Spaces." It's quite a thing, actually. And something we largely do on our own. So good for me. Good for us. How bold.

Actually, wait, strike that. The boldest thing I've ever done is just now admitting that I like the Dixie Chicks song "Wide Open Spaces." I'm not sure I'm proud of that one yet, though.

Have you lived as boldly as Richard has? Prove it: send your 500-word essay/blog post/epic poem/manifesto to Gawker at contests@gawker.com with "My Boldest Experience" as the subject line. The best (funniest, most compelling, least lame) of the bunch will be published here on Friday, and then you can revel in that particular glory and gloat to all of your friends who have Internet access. Entries are due by noon EST on Thursday, March 1, 2012.


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Richard Lawson is the senior arts and entertainment writer for The Atlantic Wire, and has previously written for The Awl, Out magazine, The Guardian, and, for four years, Gawker.com.