I was watching an episode of Jerry Seinfeld’s new project Comedians in Cars Getting Coffee. It seems an alternative title could also be Almost-Billionaires In The Twilight of Their Careers. In an episode where he sits down with Howard Stern there was a moment of conversation that caught my attention. They were discussing how when they were younger the idea of owning a production company, hiring talented artists to be creative, and having the opportunity to pick what gets developed would be a dream. The following dialogue starts at 8:40 in the episode:

Seinfeld: Would you like to play god with shows? And make shows? And say ‘I like this guy, I wanna do this with him’? How come you haven’t done that?

Stern: I had a production company and I had ten shows sold and in production. And I walked away from it. There’s nothing more exciting than the announcement. ‘Howard Stern now is head of his own network!’ You know, whatever, some big announcement.

Seinfeld: Yeah.

Stern: That’s a great high! But then you actually have to go out and get it done.

Seinfeld: Right (laughing).

Stern: And then you have no life. And that’s the problem. I love the announcement.

Seinfeld: It’s so funny how it works isn’t it? That you get to the point to get that thing. And you don’t want it.

Stern: No (agreeing)

Seinfeld: Why is life so fucking twisted like that?


Why indeed! It seems there is something demotivating about financial independence. When you actually have the time, the money, the skills to do that great project you would have loved to had the resources to do when you were in college, suddenly it just doesn’t seem like such a great idea anymore.

Maybe it’s wisdom. – A realization that those kinds of things like big projects or businesses, even though there would be some positive things, some fun aspects, and many good moments, ultimately really just don’t make some people happy and they know enough to keep a distance. Making a priority of family and just enjoying a more carefree life is more important.

Maybe it’s plain laziness and that, ultimately, given the opportunity to avoid the headaches of work, some just default to inaction over action. Though I doubt this is the case. Because people who reach financial independence early, or people like Stern or Seinfeld who amass great wealth, almost always do so through years of hard work and perseverance. Though maybe we’re only born with the ability to tolerate that for so many years before we run out of fuel.

I do see a lot of people with grand plans for when they reach financial independence. – Things like starting companies. – Or making art, movies, novels, or software. – Or working with or starting an organization to fight for an important cause. And there certainly do exist people with enough passion and drive for some things that they actually do pull off those grand plans.

But I also think a lot of people, when they actually get the point where they can make it a reality, succumb to the temptation of comfort and enjoying a quiet life.

My own approach is to just keep the door open. I don’t have any big projects planned. Though I can see how building a business could be fun. Especially if you can do it without the stress of facing potential starvation and financial ruin if you don’t succeed. Or making a independent film would be fun. Or a video game. But I also keep in the forefront of my mind that things are more easily begun, than finished. And what seems like a lot of fun when you’re in the planning stages often ends up being a source of stress, frustration and regret only six months later. And again. I don’t know if that’s wisdom or just plain laziness.

My instinct is to go build something huge. My experience tells me to hold on a minute.


Seinfeld & Stern talking.

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  1. TallMike
    Posted May 13, 2014 at 2:32 pm | Permalink

    An alternative hypothesis, perhaps specific to Jerry Seinfeld but perhaps generalizable to others: some people who attain a high level of success in a given field become obsessed with the “first principles” of whatever their field of achievement is.

    In the case of Seinfeld, I’m drawing on a profile the NY Times did about him in 2012 that included this selection:

    ‘ “Developing jokes as glacially as he does, Seinfeld says, allows for breakthroughs he wouldn’t reach otherwise. He gave me an example. “I had a joke: ‘Marriage is a bit of a chess game, except the board is made of flowing water and the pieces are made of smoke,’ ” he said. “This is a good joke, I love it, I’ve spent years on it. There’s a little hitch: ‘The board is made of flowing water.’ I’d always lose the audience there. Flowing water? What does he mean? And repeating ‘made of’ was hurting things. So how can I say ‘the board is made of flowing water’ without saying ‘made of’? A very small problem, but I could hear the confusion. A laugh to me is not a laugh. I see it, like at Caltech when they look at the tectonic plates. If I’m in the dark up there and I can just listen, I know exactly what’s going on. I know exactly when their attention has moved off me a little.

    “So,” he continued, “I was obsessed with figuring that out. The way I figure it out is I try different things, night after night, and I’ll stumble into it at some point, or not. If I love the joke, I’ll wait. If it takes me three years, I’ll wait.” Finally, in late August, during a performance, the cricket cage snapped into place. “The breakthrough was doing this”— Seinfeld traced a square in the air with his fingers, drawing the board. “Now I can just say, ‘The board is flowing water,’ and do this, and they get it. A board that was made of flowing water was too much data. Here, I’m doing some of the work for you. So now I’m starting to get applause on it, after years of work. They don’t think about it. They just laugh.” ‘

    (That’s the end of the quote, just in case it was too long to keep track.)

    I am a teacher and I am amazed at JS’s attention to craft in that anecdote. Clearly he doesn’t NEED to pay that level of attention to be financially independent, but the close detail to the finest granularity of how humor works is gratifying to him. I’ve seen similar things in other people who become fascinated by specific nuances and details in a given field in which they have already had recognizable success and don’t really need to keep pushing.

  2. Posted May 16, 2014 at 11:46 am | Permalink

    What I read in Stern’s response: “And then you have no life. And that’s the problem. I love the announcement.” is that he wanted the external validation for the project. He was not intrinsically motivated. Once he got the payoff of the work being in the public eye, the high was gone. Many people with the funds to pursue their dreams do so, work hard and create great things. But they do it for themselves. Outside recognition is just a side effect, not the driver. We just have to pursue what drives us. What brings us joy…whether the projects are big or small and what others think of them should not matter.