Life Lessons | Aging

The Unfiltered Truth About Midlife Choices and Second Chances

Os Ishmael
5 min read3 days ago

It’s never too late to reflect but don’t go blaming yourself.

A bear contemplating at 50.
Refelcting on the past. Image by author via DALL-E

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I often wonder who I would be today if I’d never taken certain risks, stayed more cautious, and followed better advice.

I probably would have avoided some regrets and might have fewer things to worry about now instead of dealing with unnecessary stress and complications. I might be at peace instead of constantly thinking about the what-ifs. Or maybe not.

My father was a risk-taker although he settled down in his mid-40s, as did I, but I’m the one who got into more trouble. It bothers me that he is still thriving in his 80s while I’m not even 60, and sometimes I feel I can’t escape the past.

He had minor regrets in his career. I feel I have them in spades. I lost opportunities, he didn’t. I faced setbacks, he didn’t. I don’t know who to blame for my missteps at times, I’m the only one in my family to make them.

The one regret I feel I can’t blame myself for I blame him for — or at least is his influence. We both faced challenges — midlife crises — but he got through them later, at 70. Me — 50. I had the advantage of hindsight, however, so I…

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Os Ishmael

Over 50 + Storyteller + Brand Builder. Award-winning marketer looking to my next 50 years and sharing experiences along the way.