Welcome to my World:

Some people choose the writing life because it's their calling, because they have no choice other than to get the words in their head out. Some people choose it for the lifestyle and the dream that something they create will be read and loved by many. I chose the writing life because I hated law.

I was a senior in college, studying for the LSAT, when I realized a) I was bad at the LSAT, and b) I didn't really care. I was trapped in one of life's watershed moments, forced to choose between my passion and a job that would buy me a car with leather interior. I mulled this over for about a week, internally debating my path in life. It wasn't easy. I love leather interiors. But I realized I love writing more. It was something I never had to stop doing; no one can make you retire from writing. Also, selfishly, I got a rush from seeing my name in print, from knowing that people were reading words I crafted. Plus, I don't like to wear pants, a requirement in most law firms.

So, over Christmas my senior year of college, I broke the news to my parents that I was pursuing my dream, sacrificing wealth and security for a chance to do what I loved.

My family took this well.

"But I've never even seen you write," my mother said repeatedly. "You're a political science major. And a boy."

My father was more direct.

"I'm not paying for your heath insurance."

Even with their overwhelming support, in reality, I had no idea what pursuing my dream meant. The phrase sounds forthcoming and bold, and it made me appear goal-oriented, but I had no specific direction, no focus. So I applied to a master's program in journalism. I rationalized my choice of journalism over a standard writing program, thinking it would prepare me for a real job (something that might even have health insurance). But over the next year, it became clear that standard newspaper journalism wasn't my thing, either. I hated the quick deadlines, "just the facts ma'am," asking people awkward questions, the inverted pyramid, having to spell lead l-e-d-e, fact-checking, etc. Plus, I still had to wear pants.

The magazine classes were my escape. Being a lazy perfectionist, I had ample time to reject and re-edit drafts. And with some strong encouragement (otherwise known as prodding) from my adviser, I began to get rejected from real magazines. Everyone had an opinion on why I wasn't getting published.

"You need to write about something funny," my roommate Ramsey, a sales associate for a staffing firm, said. "Like clowns. Everyone loves clowns."

Yet, as the denials piled up, a strange thing happened. I embraced rejection. Well, that's a lie. I still cried, but only at night after locking my door. And slowly, my writing got better. Then, to everyone's surprise, I got published. First, by magazines that paid in subscriptions or canned goods, but eventually, by real magazines actually willing to pay me—in money. My parents were astonished.

"And the check was real," my mother said when I told her the news. "The bank accepted it?"

I won't bore you with the details but, from there, things began to snowball. A piece written for Boston Magazine led to a conversation with an agent about an essay I wrote for another magazine, which led me to expand that essay into three chapters of a memoir of my middle-school experience to present to agents as a nonfiction book proposal. Now I'm editing and re-editing, meeting with agents, hoping every new cell phone call is important, wondering what a gerund is, worrying if anything is really funny, trashing other memoirs, crying in private, etc.

And that's where this column comes in. My goals are twofold: to expose the process of trying to get my first book published and to write about the experience.

My reasoning is this: If readers can see how clueless, utterly confused and nervous I am about the whole thing, then hopefully it will help them avoid these pitfalls while saving me money on a therapist.

Also, I want to address some general writing problems—insecurity, procrastination, bad writing, remembering to eat—that we all deal with, and try to offer, if not solutions, then at least my perspective on getting through them.

But most of all, I want this column to be honest and fun. The one benefit of being young and unknown is that, unlike a more established writer, I don't have to think back to remember what it was like to get to the next level; I'm right in the middle of it. So you learn as I do. It'll be like a bad reality TV show. I'll make huge, easily avoidable mistakes, and everyone can have a good laugh as they wonder what the editors at Writer's Digest were thinking when they hired me.

From there it's anyone's guess. Part of what makes putting your writing in the public sphere so exciting and, at the same time, so scary, is the prospect of finding out what people think. Before I was published, I'd relish the simple joy of writing for myself, knowing that if I was satisfied then it was good enough. But afterward, I became obsessed with people's opinions of my work. I couldn't even write in my diary without ripping out the pages, walking into my den and asking one of my roommates, "Does it need more about what I ate? How's it flow?" I felt the need to constantly be "on." It reminds me of tap dancing on cue in front of my mom's friends: forced and—now that I think of it—really awkward. But, eventually, a revelation hit me that was neither profound nor really that original. My best writing was my personal writing. Impressed by this epiphany, I wrote a phrase above my desk to remind me what I need to do.

It says: No one wins at writing. You can only beat yourself.

So, now that we've been introduced, join me next month.

We'll see who wins.