Dillying & Dallying To Greatness(?)

When to pack it in and when to push forward

If you were to look at some of my past posts you could very easily get a sense of wandering, dabbling, and dilettantism. “Oh so he’s writing country songs now? Whatever happened to that site he made around recommendations for where to live? Seems like he hasn’t posted on the blog recently either, guess that’s another thing that didn’t last…”

That would not be an entirely unfair assessment. In the beginning, I was just bopping around, pulled in different directions by impulse and interest. In my free time I would work on something up until the point where it was ready to interact with the outside world, and then I would move on. Country songs I wrote basically for myself. I got them to a finished product, something I was proud of, then declined to cross the massive chasm that separates creative completion from commercial success. It’s a chasm so rarely conquered, and I decided it wasn’t worth my time and energy. 

Same with RELO, the recommendation platform I built for where to live. I finished it, people could use it, and I even leaned on it to get some insights on where Marisa and I should move next. But then figuring out how to get other people to visit and use it? To figure out what advertising looked like? To, I don’t know, get an influencer to mention it on TikTok? That was a massive effort and might have been a good amount of money as well. In the end, I didn’t think the opportunity was big enough, nor the amount of time I could commit to it great enough to merit continuing. (And thank god I didn’t. AI + Redfin is pretty cool.)

It turns out that with these endeavors I had a vague sense of strategy that has since crystallized in hindsight: to pursue and build something up to the point where I could properly evaluate if it had legs. For country music and RELO, the answer was no (at least for now). But eventually, the theory was that if I pursued enough things, I would find one where I believed the effort to commercialize it would be worth it. I would be convinced enough of its viability that I would be willing to run against all the requisite brick walls until one cracked.

And So I Wrote A Book

This meant that in late November when I told myself I was finally going to write the book on my time acting in L.A., I couldn’t know if the end result was going to be another creative exercise or the thing that finally hit. The beauty of writing the blog, building an algorithm and website from scratch, and writing country songs was that I knew I would at least enjoy the adventure, and thus the adventure was worth taking - regardless of the outcome. All of my previous endeavors also underpinned the feeling that I had reached a point of confidence and competency to tackle a whole book. I had no guarantee other people would enjoy reading it, but I felt well-enough equipped to at least complete the project.

Fortunately I did finish it, but unfortunately a book is the thing I’m deciding to pursue commercially. I say unfortunately because I’m not a celebrity, not a known entity in the literary world, and didn’t escape the Taliban - in other words, my memoir has almost no chance of getting professionally published.

But that’s what makes this so exciting. I get to learn from all the mistakes I made acting in L.A. in pursuit of getting a book published about acting in L.A. How fun! For example, every publishing industry process and rule is designed to keep me out, which means I can’t actually follow the industry rulebook. And unlike my time acting, I don’t pay the rent through writing so I can afford to play the long game, a precious advantage. Finally, unlike my acting skills, I think the book is very good, something worthy of being published. As any salesperson will tell you, it’s a hell of a lot easier to sell something you believe in.

My next post will be about the absolute blast that was writing the book and some things I learned along the way, but for now, I leave you with a quick synopsis. Whether in six months or six years, I hope we’ll all be able to pick it up in a bookstore. (Know any agents? I wouldn’t mind talking with them…)

How to Lose It All In L.A.: A Quarter-Life Crisis Gone Hilariously Wrong

In this comedic memoir a twentysomething investment banker leaves everything he knows to pursue acting in L.A. As he descends deeper into the dark recesses of the entertainment industry, Colby meets Hollywood’s shadiest characters, endures debilitatingly embarrassing auditions, and loses his life’s savings twice over. Unsparingly honest, How To Lose It All In L.A. is a hilarious and poignant recounting of the truly questionable decision-making of a man learning everything the hard way.

It's Liar’s Poker meets The Kid Stays in the Picture with a heavy seasoning of David Sedaris’ clear-eyed satire and wit. It’s a story of a quarter-life crisis that is both timely and timeless.