10 years ago, when I was living in the Bay Area, I found myself driving past the Half Moon Bay airport, staring at a large, red blimp tethered at the end of the runway. I’d driven past this airport many times – it was on my morning surf run, the route I would take if the surf might be good enough to justify a diversion of a couple hours to catch some waves – yet this was the first time I’d ever seen this. Big and red, the sun glinting off it’s polymer skin in the post-dawn light, it was quite a vision. I actually found myself pulling over to stare at it and read the lettering on the side

As I was reading I noticed a figure – the pilot? – inspecting the blimp and mooring lines, obviously making preparations to take off. I toyed briefly with the idea of stepping out of the car, hailing him and asking what he was up to, why there was a blimp here on this particular day. I even imagined that I might be able to talk him into letting me ride along, on a spontaneous mystery journey to wherever it was he was going. But it was getting late, and I needed to get to work. So I slowly pulled back into traffic and drove on, wondering about that blimp.

I won’t say it’s the biggest mistake I ever made, but that moment, that instant when I could have stepped out and maybe taken a ride in a big, red blimp to some unknown destination has come to epitomize the coulda-woulda-shoulda moments that slip by. To make matters worse, that lettering on the side? It was for a candy company named, “Robert’s”. Yup, A red blimp with, “Robert’s Chocolate” written on the side. You couldn’t ask for a more obvious and poetic sign from on high, yet I missed it entirely. As I drove away I thought to myself, “You know, I really should just go for it”, but I just never… quite… did. And the moment was gone.

When conversations turn to regrets, the blimp is always the first thing that comes to mind. I imagine my car sitting empty, parked hastily off to the side of the road, and me gawking through a round bubbly blimp-window at the land rolling by underneath as big blimp motors roar in the wind. And the journey’s end at some unexpected airport, possibly just across the Santa Cruz mountains within an easy taxi ride of my office, or possibly far away in San Diego, Portland, or Las Vegas, implying another adventure just to return home.

These moments are inevitable I suppose: The people we never quite muster the courage or energy to meet, the abandoned pet we fail to give a home, the trip we don’t have time for. The children born or unborn. One of life’s subtle cruelties is how mundane each missed opportunity seems at the time. It slides right past us, unnoticed for what it is, and only later does the faint sting of regret seep in as we begin to wonder what might have been. Each becomes a turning point, a fork in the road, marked by a missed milepost; mileposts that I find myself tying a little red, toy blimp to in the hopes that I’ll be back some day and get a chance to see where that other path leads.