Could Have, Would Have, Should Have — LIFE

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I had a young fellow catch me one day after class  and ask for advice. You know the kind of question — “What should I do with my life?” That’s a dangerous question to hand to an old man, because we’ve got more answers than anyone wants, and none of them are certain.

I told him this:

“Son, life’s a tricky thing. Folks like to say could have, would have, should have. Those three little phrases are the grammar of regret. They sound like harmless words, but they carry whole lives inside them. You think you can predict what might’ve happened if you’d taken that other turn, but you can’t. We can never have predicted what we could have done, should have done, or would have done, or what effects that would have had. Those words are always echoes, never trumpets.”

I leaned back and thought about my own life. “Little mistakes,” I said, “can lead to bigger things. Sometimes good, sometimes bad, and you just don’t know which it’ll be. People you thought were unimportant turn out to be key. Not because they mattered much to you, but because they mattered to somebody else, or they knocked your thoughts sideways, made you see things different. I can look back and see how small little choices led to years of good things and bad things, twisted together like roots under the ground. And it’s almost impossible to predict. That’s why advice is such a slippery thing.”

The boy nodded, but he still wanted something solid. So I gave him the best I had.

“All you know is the road only goes one way. You can’t turn back. At least we haven’t figured out how. So my advice is simple: yes, prepare yourself. Yes, plan. Be ready. But don’t think that planning means you’ve got control. Life is going to happen anyway, and you’ve got to take it as it comes.”

I watched his face, saw that spark of youth that still believes it can outwit the river. “It’s kind of like surfing,” I said. “You wait for the wave, you look for it, you try to catch it. You practice your balance, you study the currents, you keep your board ready. But in the end, sometimes it’s about luck. You don’t make the ocean. You don’t pick the wave. Sometimes you catch it, sometimes you wipe out so hard you’re spitting salt water for days. But every once in a while you grab the right one, and for a little while, you’re flying.”

The boy smiled. Maybe he thought I’d given him wisdom. Maybe he thought I’d just dodged his question. But the truth is, both were true.

And that’s life.


And then I got thinking for tomorrow lecture…

Could Have, Would Have, Should Have — and Money


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