Failure #3: Birthdays Are a Terrible Way to Measure Success
Aug 03, 2025I’m turning 42 next week.
Admittedly, 42 isn’t one of those big, milestone birthdays. Well, not unless you’re a Douglas Adams fan (IYKYK). There’s certainly nothing symbolic about the big 4-2… no zeroes, thankfully. It’s just a number.
However, I’ve been doing the same type of reflective thinking everyone does when they finish another lap around the sun. And the results, as usual, are humbling.
That’s the sneaky thing about birthdays. Even the quiet ones have a way of turning into personal performance reviews. For most of us, once we start measuring the distance between the life we imagined and the life we’re actually living, we can’t help but feel like failures.
But that feeling — common as it is — assumes we all had some sort of “correct” timeline in the first place. We imagine we were supposed to hit certain milestones by certain ages, and if we accidentally wandered off that timeline — perhaps gotten stuck, or maybe taken the long way around — then we must have done something wrong.
That’s what failure is, right? Falling behind?
Except… behind what? Whose timeline are we actually following?
Running a Race Without Clear Milestones
Most of us never consciously chose the expectations we use to measure ourselves. By that I mean, we didn’t sit down at age twelve and draft a life plan. Instead, we picked things up by proximity — from our families, our teachers, our peers, and every TV show or movie that hinted at what adulthood was supposed to look like. Somewhere along the way, those inputs turned into deadlines.
Graduate by 21.
Dream job by 25.
Marriage by 30.
Financial stability by 35.
Emotional clarity by 40.
How realistic are any of those milestones? If you’re lucky, you’ll hit a few. But even if you do, you’ll almost certainly still feel behind because no matter how much you accomplish, you’re always going to encounter someone doing it faster, or younger, or with better lighting on Instagram.
The real trap of birthdays isn’t the fact we’re getting older. We’re all getting older all the time, so birthdays aren’t technically any different. Instead, birthdays push us to measure ourselves against timelines we’ve forgotten were imaginary to begin with. At best, they’re poorly informed guesses. More likely, they’re some combination of cultural generalizations and vague expectations from people we probably wouldn’t trade places with even if we could.
Unfortunately, when we mistake those comparisons for truths, we start judging ourselves unfairly, and we call ourselves failures when we’re really just confronting variance.
Knowing the Right Timeline for Your Life
Next time you're faced with a moment — intentional or accidental — where you’re forced to compare yourself to whatever version of you you dreamed of in your head as a kid, I want you to pause, take a deep breath, and remind yourself that the people we admire most rarely got where they are by following a clean, predictable path. In fact, I suspect if you were to ask them, they’d be the first to tell you their success stories are full of detours and delays. They missed deadlines. They changed directions. They wandered and rebuilt and tried again.
That’s not failure. That’s how life works.
So no, on the eve of turning 42, I haven’t magically uncovered the answer to life, the universe, and everything in between. But it have been reminded of something we all probably need to hear more often than we do:
Don’t judge the life you’re living by a timeline you set when you knew less about yourself and the world.
At some point, the goals you once held might stop making sense, and the markers you thought would define success might lose their meaning. That doesn’t mean you’ve failed. It means you’ve grown. And growth almost never happens according to schedule.
You’re not late. You’re just moving at the speed of reality. And that’s not failure. It’s exactly what progress looks like when it’s honest. And, yes, it’s worth celebrating with an extra slice of cake.
- Dr. D
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