The Peri-Winkle Wellness Blog

A few weeks ago, I ran a live workshop as an executive function coach, where a group of women built out their September calendars together, in real time. We spent an hour doing something most people never sit down to do deliberately: mapping out an entire month, day by day, before it actually arrived. Partway through, one mom mentioned something that’s stuck with me ever since: when she sat down to map out everything a child’s birthday party required, she was stunned by how much was hiding behind a single calendar entry.

We’ve all had the if onlys. If only I had waited to get married. If only I had landed that job. If only I hadn’t let people treat me that way.

It’s easy to look back on our lives with everything we know now and fall into regret or self-judgment. With years of experience behind us, our perspective sharpens, but it can also become unforgiving. Therapists call this hindsight bias: the tendency to evaluate past decisions with the clarity we didn’t have at the time. In midlife, when reflection feels almost inevitable, hindsight bias can make earlier choices seem flawed or shortsighted, even when they weren’t.

I tried to ignore it for as long as I could. But no matter how hard I tried, it slapped me square in the face every time I looked in that damn mirror. I was aging. Not gradually, not subtly—but undeniably. The crow’s feet, the pesky bunny lines, the unwelcome age spots all conspired against me. But what unsettled me most was something harder to name. My entire countenance seemed to be changing. The longer I looked, the more unfamiliar I appeared. It was as if I were turning into someone else.