I have been thinking recently about how it seems that most everyone my age isn’t happy with their life. Your relationships with people are made closer and stronger through a shared outside conflict and recently much of that conflict - as well as the stronger bond that comes from it - has come from sharing about the existential struggle that they have from their work. No matter where it seems that these people come from - Taiwan, Singapore, Sacramento, New York, Norway or more - it feels like many of my friends are dissatisfied with where they are in life, what they have achieved in terms of careers, who they are as people.

Maybe it just might be me. Totally possible. Perhaps the people I talk to - the types who enjoy talking to me - turn out to be the types who struggle with questions like these in their spare time. Upper middle class types with too much money and not enough struggle in their lives. I once talked to a girl on my flight back from Taiwan who truly was struggling in her life - my age, a college dropout, a go-nowhere job, and a true paycheck-to-paycheck existence. That’s truly a troubling situation - and if you were to take Maslow’s hierarchy of needs as gospel - then I am a privileged person to be even thinking about this sort of self-actualization crap.

Maybe we all feel terrible because it seems like to each everyone else that they all got their shit together. That someone out there has finally managed to grow up, figure it out, and get right on to living LIFE - whatever that might be. Might not even a real life person, might even be some sort of ideal image of a person, built up by the media, our peers and family’s expectations, and our own Facebook-clouded misperceptions. But SOMEONE out there. They finally got it licked. God, I wonder what that feels like.

But what I am getting in my data samples are just more of the same uncertainty, the same unhappiness. It’s like nobody’s got a real clue, which reminds me of my favorite quote on leadership (and possibly LIFE?!?) comes from a character in F. Scott Fitzgerald’s final (and unfinished) book named Monroe Stahr, the Last Tycoon:

Supposing there’s got to be a road through a mountain - a railroad or two or three surveyors and people come to you and you believe some of them and some of them you don’t believe, but all in all, there seem to be half a dozen possible roads through those mountains, each one of which so far as you can determine, is as good as the other. Now suppose you happen to be the top man, there’s a point where you don’t exercise the faculty of judgement in the ordinary way, but simply the faculty of arbitrary decision. You say, ‘Well, I think we will put the road there’ and you trace it with your finger and you know in your secret heart and no one else knows, that you have no reason for putting the road there rather than in several other different courses, but you’re the only person that knows that you don’t know why you’re doing it and you’ve got to stick to that and you’ve got to pretend that you know and that you did it for specific reasons, even though you’re utterly assailed by doubts at times as to the wisdom of your decision because all of these other possible decisions keep echoing in your ear. But when you’re planning a new enterprise on a grand scale, the people under you mustn’t ever know or guess that you’re in any doubt because they’ve all got to have something to look up to and they mustn’t ever dream that you’re in doubt about any decision. Those things keep occurring.

We are all building our own railroads through our own mountains. Other people have a lot of advice for us. Some ways we should definitely not go (meth addict), others would be cool but impractical (billionaire heir), while others do not seem all that different from each other (accountant, bookkeeper, insurance salesman, marketer?). We all end up at the same place, it is just how you get there.

Sometimes people ask me, why did I do this? Where am I going with this particular pathway? What I am kinda afraid of telling them (ESPECIALLY if they are older than me) is that I don’t really have a specific reason in mind. Just like Stahr said, I just put my finger down and said, “There we go”. And there’s no reason for it - I am lying when I pretend that I have a clue. I am just pretending to have a clue putting down my tracks - wagering my ENTIRE life’s efforts and time on it, by the way - and all the while looking over at everyone else’s tracks and thinking, “Well Gads, this guy looks like he knows where he’s going … and here I am just making this shit up as I go along.”