As we meander through life we carry a figurative bucket filled to the brim with coulda/shouldas, decision points where we screwed up. As a certain milestone birthday approaches, I pawed through the bucket and unearthed dozens of epic, awesomely blockheaded and consequential screwups.

Surely, I reflected, no one person could have made so many egregious mistakes, missed so many obvious opportunities and displayed such profound ignorance of the world around him.

So here are a few, including one ringer. Guess which one is fake, and I’ll join you for a beer after work and give you free investment tips!

• 1956 — In Aspen with pals, hoping we can get served at one of the low-rent downtown bars. Walking through the then-shabby little town, I noticed a For Sale sign in front of a stately brick house on a big lot surrounded by a wrought-iron fence. The sign noted a recent price cut to $15,500. My thought: Who would be crazy enough to pay that much for some Aspen dump?

• 1958 — I had a sweet little 1956 MGA roadster. In Denver one afternoon, I stopped at a vintage car dealership. The owner pitched me on a Duesenberg SJ — he’d take the MGA in trade, and I’d have to make payments for a few years. I demurred — why would I want something that big, that old and that impractical? Had I bought the SJ, stuck it in a garage and sent it to Barrett-Jackson this year, I could retire with a comfortable seven-figure bank balance. And had I kept the MGA, I’d have a nice little appreciating asset. Instead, I’m driving a broken-down 2002 Nissan Xterra.

• 1964 — In Tahiti, just married and trying to figure out what to do with my life. I could have stayed in paradise, chartered my sailboat and invested for the future. An opportunity: 100 acres of beachfront land in Puna’auia, a then sparsely populated area a few miles from Papeete. The price: $30,000. I passed, and left the island.

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• 1970 — In New York City, my childhood friend and NYC resident Tim Collins was an art collector. At a party at his townhouse I met Alice Neel, an artist who had painted portraits of both Tim and his mom. Neel, a lively 70-year-old, offered to paint me.

“You don’t have to pay me unless you want the painting,” she said. “But there’s a condition — no clothes.”

Ashamed of my then-flabby bod, I declined. Neel is now considered to be the greatest American portraitist of the 20th century.

• 1972 — I was living in New York at 27 Washington Square North. The city was close to rock bottom, three years before the famous Daily News headline (Ford to City: Drop Dead!). The owner of the building wanted to condo it, giving existing tenants first dibs. I was no fool — I knew that New York City real estate, however prime, would never be worth anything. I moved to another rental.

• 1981 — Back to Colorado Springs, we rented a house in Rockrimmon and looked for a place to buy. A three-story Victorian on Tejon Street was for sale, just steps from my childhood house. The price: $70,000. I liked it, but my then-spouse didn’t. It reminded her of houses in a ramshackle, dangerous neighborhood of the eastern city where she grew up. I caved, and we stayed in the Rockrimmon rental.

• 1986 — My stockbroker, Dennis, called and pitched me on a stock that was about to go public. I brusquely interrupted his pitch.

“Dennis, it’s a software company,” said I with uninformed authority. “All software companies go broke, and this is no exception.”

“I can get you 500 shares,” Dennis continued. “There’s a lot of interest in this company — I think it’ll stick around.”

The company: Microsoft. Those 500 shares would be worth $3.6 million today.

• 2003 — Swapping brags about our clever descendants, a college friend told me about his grandson, Mark Zuckerberg.

“He’s scary, he’s so brilliant,” he said. “Someday he’ll rule the world. He’s about to drop out of Harvard and start a company. We should all invest.”

I told him my son did a high-tech startup a few years back, and it didn’t work out.

“So I think I’ll pass,” I said.

The point: When opportunity knocks, it’s disruptive, inconvenient and unrecognizable. It’s also persistent — so much so that I expect a few more shots at the brass ring.  n CSBJ