The Older I Get, the Less I Know For Sure

It Was Going So Well…

It happened again the other day, right in the middle of a conversation.

I was making a point—something I would have felt completely certain about not that many years ago—when, almost without warning, I felt that familiar shift. It’s hard to describe, but it’s like my mind quietly steps to the side and starts watching me talk. It’s like I’m still in the room, but no longer fully inside my own point of view. And from that vantage point, everything loosens. My argument. My certainty. Even the tone I’m using.

In the span of a few seconds, I can suddenly see how the other person might be hearing me. Or how the situation might look from a completely different angle. Or how what I’m saying might only be partially true, shaped more by my own bias than I’d like to admit.

And just like that, I lose my footing a little. There’s a slight hesitation as I try to keep the conversation moving without missing a beat. I don’t even know if the other person notices the shift. And if they do, I have no idea what they make of it.

This isn’t new. It’s been happening more and more over the past decade. And lately, I’ve started to wonder: is this what wisdom actually feels like… or is it something else entirely?

It doesn’t always stop there, either.

The Replay I Didn’t Ask For

Sometimes the conversation ends, I move on with my day, and everything feels settled enough. But later—often when I’m not even thinking about it directly—I’ll be doing something ordinary, like walking on the treadmill or working in the garden, and it comes back. And when it does, it rarely comes back the same way.

I’ll replay parts of it in my mind and start to see things I didn’t catch in the moment. A different interpretation. A shift in tone. Something the other person said that now lands differently. Or something I said that I’m no longer entirely sure I meant the way I thought I did.

And that’s usually the point where it starts to go a little further than I intended.

Once that door opens, it doesn’t stay contained to just that one conversation. It starts to pull in others. Similar situations. Patterns. And before long, I’m revisiting things from years ago—sometimes decades ago—with a completely different lens than the one I had at the time.

Even things from childhood, for goodness sake!

Moments where I walked away feeling like I understood what happened—why someone said what they said, or why something unfolded the way it did. At the time, I filled in the gaps the only way I knew how—with what felt like reasonable, even logical explanations.

But now, looking back, I can see how much of that was assumption.

Not intentionally. Just… the mind doing what it does when it needs a complete picture.

And lately I’ve been wondering—what if those assumptions weren’t accurate at all?

Assumptions about things I never actually witnessed or confirmed—just filled in because they seemed to make sense at the time. And now I find myself questioning how much of what I believed was built on something solid… and how much was constructed.

It’s an unsettling place to go, because there’s no real way to resolve it. Most of those moments are long gone. The people, the context, even who I was at the time—it’s all changed. There’s no clean way to go back and verify any of it.

So I find myself asking a different question: what’s the point of revisiting any of this if I can’t actually know the truth?

And yet, that doesn’t seem to stop it from happening.

They Still Think I Have Answers (teehee)

I see it show up in other ways too—especially in conversations with my kids.

They’ll come to me looking for a perspective, or an opinion, or sometimes just to talk something through. And more often than I would have expected, I find myself hesitating.

Not because I don’t want to help. But because I can see more than one way of looking at what they’re bringing me. I can see how different interpretations could all make sense, depending on what you assume, what you prioritize, or what you’ve experienced before.

I can see, through my own experience and watching others, how similar choices have played out in very different ways. The “what not to do” scenarios tend to stand out more.

And interestingly, when it comes to decisions in my own life, that wider lens feels like an advantage. It feels grounding, even empowering.

But when it comes to advising someone else, it feels different.

I don’t want to overcomplicate things for them. But I also don’t feel right offering a clean, confident answer when I can see how many ways it could be understood.

So instead of saying something definitive—the way I might have in my 30s or 40s—I’ll sometimes offer a few simple thoughts from different angles… and then stop.

“I don’t know,” I’ll say.

Big help there.

I don’t know the role to play here anymore. I was an involved parent while raising my children, a teacher for many years, and a product of a time that encouraged critical thinking and having a voice.

All of that shaped me to offer guidance, to help make sense of things, to provide direction.

But that part of me now sits alongside something else—an awareness that people have their own paths, their own interpretations, and their own outcomes. That my experience isn’t theirs. That there isn’t always a single “right” way to see something.

I’m also keenly aware that people interact with one another very differently than they have traditionally. Their values appear to have shifted so dramatically across all elements of life, family structure, workplaces, money systems, etc.

Advice from the past may, or may not, be relevant. I have absolutely no idea what the world is going to look like, even 10 years from now. I don’t know what to advise.

Are all past paradigms in fact, completely useless moving forward? Or, do we still value “history repeats itself if you don’t remember it”? Who knows. Are people, just people, no matter the decade or century? Or are we moving into something entirely unrecognizable that requires a whole new way of thinking?

This is Not How I Used to Show Up

The truth is, I don’t know in the way I used to. Not with the same certainty. Not with the same confidence that what I’m saying is the right way to see it.

I just know that there’s usually more to it than what first appears. That sometimes two conflicting truths can be true at the same time.

And I’m still trying to figure out if that’s a good thing (growth) or a bad thing (decline in brain power).

I’ve been starting to wonder if part of the discomfort isn’t coming from the questioning itself—but from what it’s replacing.

There was a time when things felt clearer. Not necessarily because they were clearer, but because I didn’t yet see how many gaps there were in my understanding. I filled them in without realizing I was doing it. Most of us do. We take what we know, add what feels logical, and build something that resembles a complete picture.

And for a long time, that works.

It gives you a sense of footing. A way to move through the world without constantly second-guessing every step.

This Might Be the Trade-Off

Maybe part of getting older isn’t about replacing certainty with clarity—but learning how to live without needing things to feel fully resolved.

And maybe saying “I don’t know” isn’t always a failure to arrive at an answer.

Maybe sometimes it’s just a more accurate place to stand.

It’s just not nearly as comfortable as it used to be.