In September, 2009, I quit my job at The New York Times to focus on stand-up comedy and writing. Abandoning the comforts of corporate America to pursue one’s “art” is almost trite. It might be bold and romantic, but it’s hardly unique – especially in New York City where one can eavesdrop on similar stories of “bravery” at any cafe on Tuesdays at noon. Turning my back on one stereotype, I was concerned about becoming another. I worried about quitting.

If I never responded appropriately to the discipline of a real job, how could I possibly do anything when deadlines were self-imposed?

For the first 4 months, I talked a lot about what I was going to do. “I’m going to put together a set for Conan.” “I’m going to finish the screenplay.” I felt productive committing to things, then angry when I failed to follow through. I would quell that anger with a promise to infuse more energy into my next commitment, only to fail again. I was lucky and thankful to be spending so much time with my wife and kids, and to this day, it’s been the best part of the experience, but I wasn’t supposed to be retired. I needed to build a structure that excuses couldn’t topple.

I thought of it like this: The differences between dieting and getting sober are vast. Dieting means eating less, and you’re constantly tempted with morsels of your addiction. Being sober – though difficult in practice – is an easier concept:  never drink again. I made a similarly unambiguous commitment to writing. If I tried the diet method, committing to three blog posts a week, the temptation to procrastinate would undermine the much needed routine.

I told everyone willing to listen, that I would write something every day for a year. I had no other goal but to write and self-publish each day. There was no expectation of success beyond that. I believed I would do it, but was also haunted by my awful track record of promise keeping. The first few posts were filled with self-flagellation and doubt.

Excerpt from Day 1:

One of the things I wanted to do when I quit  was “blog about my daily progress (progress toward what, I’m not entirely sure). This is the first post. I could pretend like this is really day 1, but I think the fact that it took me 4 months to even do the first post teaches you more about me than 120 posts ever could. I spend all my waking hours disappointing myself.

What few readers I had appreciated the honesty. Some even reached out to offer encouragement. One of them said, “You won’t make it past April,” but he meant it in a loving way.

By week two, I was still punishing myself for past failures.

Excerpt from Day 14:

This is the first thing I’ve ever done for two weeks straight besides penicillin.

But I was also beginning to have fun, and see hints of my voice coming through. In the same post, I wrote about returning to Brooklyn for the first time after having moved to New Jersey,

It’s amazing how we can romanticize our past. We went to our old coffee shop, remembering how amazing it was. When we walked in I thought, “Wow, I forgot that everyone brings their dog in here.” The coffee is great and you can’t get a decent coffee in New Jersey, but lord can hipsters make a family uncomfortable without even trying. Hey dude with the macbook, wingtips and bulldog, you aren’t even looking at me, but I can tell by your hair that my kids are annoying you.”

It wasn’t long before my commitment to the blog began to mirror my sobriety; I’d done it for long enough that the idea of starting over provided all the fear I needed to keep going. It was also now a household ritual that even my three year-old understood, “Daddy, are you going upstairs to write your blog?” My wife’s support was tireless, and still is, fifty two weeks later. In addition to emotional support, she reads every single word before I send it out.

At the beginning of the third month, I started to feel like I was a writer. But when I read Dave Eggers, T.C. Boyle, Jonathan Ames, or David Sedaris, I often felt the same way about writing as I did about stand-up the first time I saw Patrice O’Neal. “Wait a minute, I have no idea what I’m doing.” At that point, you can either quit while you’re behind, or dig in and do the hard work it takes to shrink that gap. A quote from Ira Glass explains this best. Here’s part of it:

All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.

At least I could blame my self-doubt on the burden of having good taste.

The blog wasn’t my only creative project. I was also writing a 30-minute comedy pilot for television titled Making Good. It’s about a father striving, and mostly failing, to maintain a job, a career in stand-up comedy, and a happy home life. I was more focused on the success of Making Good, than I was Most of my days were spent tweaking and rewriting the script, while trying to squeeze in a quick blog entry sometime around lunch.

After completing that project, I wrote another comedy pilot, called “Kustard Kings” about an economically divided town awkwardly drawn together when the family of an idealistic Marxism professor inherits the local ice cream truck business. Shortly after clicking “save as” and typing “Kustard Kings draft 1_complete,” everything changed. In a 20 minute flurry, I listed  what I thought went through my 2 year-old son’s head over the course of 3 minutes. I was glad to have gotten that day’s entry out of the way so quickly. When I showed it to Lindsay and my mom, they each laughed so hard they cried. I should mention they’d been drinking, but still, it seemed like maybe I’d created something special.

Day 215: Approximately 3 Minutes Inside the Head of My 2-year-old  quickly went viral. Though the majority of people read that one entry and left, there were enough who stuck around and poked through other entries, that I was beginning to build an audience. Parenting is hard, and I’d enjoyed writing about my kids so much already, that I decided to do more of it.

A Toddler Rite of Passage, The Saturation Failureand Great Jobs for New Parents all seemed to speak to fellow child rearers. Though I was sharing the very specific details of my own experience as a father and husband, it was that specificity which drew people in. It’s ridiculous, funny and complicated to be so in love with tiny people who are often frustrating and unpredictable.

A month after posting Approximately 3 Minutes Inside the Head of My 2 Year Old, I received an email from an editor at Bloomsbury Publishing. She’d come across the post in her Facebook feed and asked me if I’d be interested in making it into a children’s book.  I responded with a polite, “Oh, I think that’s a great idea.” The book is due to come out in 2013, with two more to follow, the topics of which are yet to be determined.

As you might imagine, I got a great boost of confidence from the recognition. Yes, that attention was coming from a list of thoughts I wrote in 20 minutes, and not from one of my more writerly entries, but it didn’t really matter. I felt like I was on the right path.

A few weeks later I was approached by a different publisher to do a gift book for new parents. I passed on that offer in hopes that my first “real book” might be something more significant. Whether that was the right decision or not, I still don’t know. I was told that if I wanted a career writing books, I should “start how you want to finish.” In other words, if I’m going to write  books, make sure the first one sets me on a path I’m interested in taking.

I had also started to connect with some of the more memoir style writing I was doing. A piece about my father-in-law titled, The Blue Blazer, as well as the two about my grandfathers, The Pinewood Derby, and Edwin Good, felt right and real. I was getting more comfortable seasoning my acerbic voice with some tenderness. Considering how uncomfortable I am with that last sentence, I still have some work to do in that area.

At the same time, I was also connecting viscerally with chronicling my daily life. Lindsay, Silas or Arlo would do something funny, and I’d write about it the next day. I was keeping a journal, really; taking snapshots in my brain and expanding on them the next day. Those posts will provide far more emotional value than any picture or video.

A big chunk of my sense of humor comes from criticizing and making fun of myself. I’ve painted my life in this blog with that set of brushes. It’s easier for me to make light of poor choices, honest mistakes, moments of panic, and times of frustration, than it is success, happiness, serenity, and cuteness. The picture you have of my family might be one of four people run amuck  – of an ear picking, foot rubbing husband struggling to enjoy life;  a wife who never sleeps and can’t remember simple words; and their two young children who stomp all over them. If I could tackle the amazing stuff head-on and make it funny, I would. I hope, though, that through the harsh realities I communicate about my life, you see that I’m lucky, and thankful; that my kids are amazingly perfect, and my wife, the strongest most giving person I’ve ever met.

I set out to change my life, and all of you helped me do that.

I'm a contributing writer to Parents Magazine, GQ, Psychology Today and some others. My book, "This is Ridiculous. This is Amazing: Parenthood in 71 Lists" is available here Look for two more books in 2015: "Must. Push. Buttons (Bloomsbury Kids), and an as-of-yet untitled memoir I’ve appeared on Comedy Central’s “Live at Gotham” and “Nick Mom’s Night Out." I live in New Jersey with my wife and two sons and enjoy making them laugh more than anyone else.

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