The man at the bar in Monterey

Bill told me a lot of things, that man at the bar, but he had that rare demeanor of someone who more often than not is asking for details as opposed to speaking of his own conquests and aspirations and vacuous desires. We went back and forth on a lot: the strange path my life has taken, balancing risk and adventure; the ins and outs of San Francisco, which soon I will understand; his challenging personal situation, one that made him look tired, which at one time I could certainly relate to. It was refreshing all around, over a couple cold pale ales, and in my long history of sitting down at random bars in sidelined cities, clamoring away from most conversations that just don’t seem to end and people who do not know when to shut up, I recognize you don’t run into Bill-like characters every day.

I should explain more about Bill. He is seemingly straight-laced, probably early 50s, no children, recently divorced, and a financial planner. Naturally, in one of my more introspective moments, expecting a bland and by-the-book response, I asked him for advice. I asked what he would recommend to a young budding 25 year old who wants to balance experiences these days with security in future days, and as a response, he gave me without hesitation two short stories.

In the first, a client with an especially well-designed retirement package found out one day, out of nowhere, that he had terminal cancer with a year to live. That money, as these things go, would then go to his only son, who has proven himself to be especially irresponsible and impulsive in his late adolescent years. There was understandably a tone of tragedy and hopelessness to this one.

Then I was told of a man who, though everything is done, continues to come back to Bill seeking advice. Bill tells him the same thing again and again: you are fine, you have done everything right, now go do what you want to do and enjoy. “But I just don’t know what to do with all this spare time,” he continuously replies. Arguably some retirement stories solicit more empathy than others.

In a world where we are all navigating future outlooks and obsessing over risk, and perhaps even some utopian time yet to come, this all meant a lot to me from the horses mouth. There may come a time that I wish vaguely I had set more aside, planned this or that, had a 401K going at 23, and many other fiscally responsible ventures. That time may come indeed. But I’ll never regret those days cruising slowly up the Pacific Coast Highway, and the night I landed in Monterey, before that great storm blew in out along the Pineapple Express.