Authentically successful

There’s a scene in Jerry Seinfeld’s Comedians in Cars Getting Coffee that I swear I saw but, of course, now can’t find. The gist is Seinfeld and Jim Gaffigan are talking about the role luck plays in career success. Seinfeld is dismissive. In his view, it’s about work, work, work: putting in hundreds of hours honing material; obsessing over every word; enduring bad stand-up sets but soldiering on. Gaffigan agrees, riffing about people who watch shows like Seinfeld and say, from the comfort of their sofa, "I could do that, if someone would just give me a chance.”

As I recall the Gaffigan bit, it’s at that moment that the door bursts open and a crack squad of unknown genius identifiers appears. “You’re right,” their leader says to the if-I-only-had-a-chance comedian on the sofa, who’s no doubt wearing boxer shorts and a t-shirt. “You are funnier than Seinfeld. We like to give you your own sitcom.”

Wouldn’t it be nice if it was that easy? I mean, I’m as guilty as anyone for maintaining a running commentary audible only to me where every daydream ends with, “I could do that if only someone would give me a chance!” But I’ve been an horrendously slow learner on the got-to-get-out-there front. This isn’t to suggest I haven’t been successful—that may have contributed to my failure to absorb the basic lesson about being in the arena. But as I examine who I truly am, what makes me tick, and how I can marry that with what I do, the issue of be, do, have keeps echoing.

Just yesterday, I was reading a book showcasing surf shacks—which is what you do when you’re thinking about the kind of home you’d like next—that quoted Australian furniture maker Mark Tuckey: “I think you kind of create your own luck if you put yourself out there. It’s like surfing; you’ve got to paddle around to find the waves. Sit still, wait for them to come to you, and you’ll miss everything.”

Then today, in an act of cosmic kismet, a piece of art I ordered a couple of months ago for my new apartment was delivered. It’s a beautiful textile piece that’s part of Ali Beletic’s Freerider Flags series, inspired by the words of Hunter S. Thompson—it’s the pic accompanying this post. The phrase I’d chosen? “Catch waves.”

Now, I’m not as dismissive as Seinfeld of the role luck plays in success. And I suspect even he’d admit that, deep down, there’s absolutely an element of serendipity in being in the right place at the right time. After all, you can throw a dart at any talent reality show and hit someone amazing whose gifts have, until that point in their life, been overlooked. But I take Seinfeld’s point to be that you’re exponentially more likely to find yourself in the right place at the right time if you’re actually out there, visibly and consistently.

The word place is possibly the one working hardest there (Steven Pressfield’s The War of Art underscores this). If you wanted to change the course of American literature, being in Paris in the 1920s was a pretty savvy move. The movie industry? It’s always been and remains LA. Ride the dotcom boom? Silicon Valley, any time in the 1990s. AI today? You probably want to be working for—or adjacent to—Microsoft and the exponentially expanding AI sector. It holds true for almost any industry and can get awfully specific. Rock’n’roll back in the day? New York City’s CBGB on the east coast; The Troubadour on the west. The surf industry? Torquay in the 1970s; SoCal ever since.

The bottom line is succeeding in any field is more likely when you’re surrounded by likeminded people in a creatively fertile environment. Now, it’s also true that your ability to sell all of your worldly goods and become a rockclimbing bum in Yosemite tends to narrow as you get older, your career becomes more calcified, and your willingness to take financial risks reduces. But there are two things that give me heart as I continue my journey to be more successful as defined by what’s authentic to me and who I am.

First, proximity remains important—for sure. Ideally, whatever field you want to excel in would be like finding yourself in The Outsiders in 1983 with unknown actors named Tom Cruise, Rob Lowe, Diane Lane, Patrick Swayze, Matt Dillon, Ralph Macchio, and Emilio Estevez (among others). But finding people who scratch your particular creative itch has never been easier, even if forging actual relationships is more difficult through a dodgy Zoom connection.

Second, one thing I’ve realized as I’ve progressed in my career is how it’s possible to both provide opportunities for others and be the grateful recipient of them. It’s really not a big deal to throw some work to someone when it makes sense, and it’s amazing how often one step leads to two, three, then a bright idea, and before you know it’s you’re doing something really interesting and gratifying.

So, the journey continues. Catch waves.