Regrets, I've Had a Few

“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” -- H. Jackson Brown (often misattributed to Mark Twain)

I don't generally do New Year's resolutions, and I'm not really planning to start now. I do have something I'd like to work on, though, so I'm telling you about it in hopes you'll hold me accountable.

I'm a flawed and imperfect man in ways to numerous to count. For the purposes of this post, we'll stick to just one thing (though I'm sure you'll feel free to enumerate others in the comments). Today, we're here to talk about my general inability to go from inspiration to execution.

I get lots of ideas. Get 'em all the time, really. Big ideas, small ideas, crazy ideas, inspired ideas - I get all kinds. Sometimes I even tell people about my ideas, in the hopes that naming them will force me to follow through. It doesn't. I can't get over the walls, almost always self-built, that block my path. I'm a dreamer. But I'm not a doer.

This blog, even as it's lasted more than 11 years, is an example. Started in a righteous flurry of creative inspiration, it wouldn't exist today if Teejay hadn't picked up the ball when I grew tired after the first dozen posts or so. Teej, at first alone and later with Whitney, carried G:TB through the wilderness of 2004-2007 until a combination of William & Mary basketball success and external validation roused me from a long blog-slumber. None of that happens if I'm the one that has to make the effort.

Not this Socrates

Socrates is credited with saying, 'the unexamined life is not worth living'. I started to examine myself, trying to figure out why I can't finish anything, but I got distracted. But I did hit on one fairly obvious truth: I'm too often willing to settle for the comfortable known rather than striking out towards a possibly awesome but certainly scary unknown. Here's an example:

I met the late Mark McCormack in 1997, while I was a graduate student. He attended several cocktail parties at a friend's parents' house, and I struck up an acquaintance. Tiger Woods was in his ascendancy, and Mr. McCormack would often seek me out at these parties to ask how his most lucrative property had performed that day. He knew me by name. As my graduation approached, I got a call from Mr. McCormack's secretary, telling me that IMG had a job opening that might interest me. When I called the hiring executive, he let me know that Mr. McCormack had recommended me for the job, which was, as I recall, a very cool opportunity in IMG's television production business.

It was also an unpaid internship. In Manhattan.

I had recently become engaged, had a negative net worth, and was staring down the barrel of $40,000 in student loans. A more ambitious and adventurous man would've thrown caution to the wind, figured out how to get a job waiting tables or tending bar, and jumped in with both feet. I, as you know by now, did not. I couldn't get past the negative, the worry about how I could make it work, to get to the upside. I had lots of practical reasons to turn the opportunity down, and I kept the bowlines securely fashioned, safe in the harbor.

Life has worked out okay for me thus far. Better than that, if we're being honest. But I remain stuck with a nagging sense of what might have been. With that opportunity, and with half a dozen other decisions that were never made, projects that never got off the drawing board (with several other guys in the late 90s, I started talking about a cloud computing start-up, well before that marketing catchphrase existed - kept talking, too, but didn't actually do anything), recurring blog features that didn't recur, risks untaken.



I frequently tell people that I don't know what I want to do when I grow up. Partly because it's true, and partly because it's a convenient excuse to not think too hard about it. I suspect I'm not alone on this (or much of what I've written in this post, really). Rachel Gillett of Fast Company wrote about this phenomenon in an article about conducting a life audit, describing her level of intimidation when forced to actually write out her life goals and share them with others.

Wrote Gillett, "I felt nervous that 1) I wouldn’t have enough goals and I would realize that my existence is pretty pitiful and, 2) I have a ton of goals but I will forget all of them in the moment or not know enough or have done enough research in my daily life to know what any of it means."

I don't have any illusion that writing all this down and sharing it with you will make me suddenly a risk-taking, devil-may-care free spirit. My New England pragmatism is far too ingrained for that. But my goal for this year is to channel Miles in Risky Business. I want to say "What the fuck" more often. As Miles says, "What the fuck gives you freedom. Freedom brings opportunity. Opportunity makes your future."

I'll test my resolve on this early. I'm working on a couple of projects with other Gheorghies. Normal me would stop in a week or so because that's the easy way out. Nothing ventured, nothing gained, nobody gets hurt. What the fuck? What's the worst thing that can happen?

Tell you at the end of the year.