When Reflection Turns on You

The line between learning from a moment and getting stuck in it.

Have you ever done something you thought was wrong, and then kicked yourself immediately after?

It’s a very common pattern. And to a certain extent, its quite normal.

But, the force of that kick can land extra heavy for those of us who are highly self-aware.

Several years ago, I jumped into a stretch role at work. My third week in, I facilitated a 2-day planning event with over 100 people on a call. At one point, while guiding an exercise, I over analyzed a risk in real time in front of EVERYONE. I paused longer than I should have to the point where it felt like I froze.

It felt embarrassing.

I couldn’t stop replaying the moment in my head.

It wasn’t until a trusted colleague and friend congratulated me on getting through the event that something shifted. I was so focused on that one negative moment, I had not given myself ANY credit just for getting through the event, which was an accomplishment in itself.

I also realized I was still stuck in a moment that had already passed.

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Lately, I’ve been trying to understand why it’s so easy to get stuck replaying moments where we feel like we got something wrong. And I’ve noticed a pattern that looks something like this:

Awareness → reflection → over-analysis → self-criticism

So why is it easy to get stuck in this loop?

I have started exploring this question more and I come back to a few key things below.

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1. Self-awareness

For those of us who are self-aware, we notice everything. We focus on what we say, how something landed, and what could have been better.

Don’t get me wrong. Self-awareness is a strength. In fact, Aristotle had something to say about this.

“Knowing yourself is the beginning of all wisdom.”

But without a stopping point, it can turn inward and start a not-so-pleasant cycle.

2. We are trained to always improve and we care deeply

We want to show up well. We want to be respected. We care about our work.

So when something feels ‘off’, our first instinct is to try and correct it or do better. This continuous improvement mindset can be healthy, but we have to ensure the improvement desire doesn’t turn into vigilance.

What doesn’t always help is that everywhere we look around, we see things such as:

• “Optimize the way you work”

• “Save time by using this new tool”

• “Get the very best out of your notes” (Had to throw in a Substack example!)

We’re trained to find the gap and fix it.

Over time, this mindset (if we’re not careful) can bleed into how we think of ourselves, not just our work.

Personally, I sometimes find myself saying something like “I didn’t handle that well'“, instead of a healthier reframe such as “that didn’t land well.”

The former turns it into an identity problem. The latter keeps it as a moment.

4. There’s a subtle protectionism mechanism

If we critique ourselves first after a mistake, we stay in control. Judging ourselves first allows us to get ahead of any other person’s judgement. While it may feel like we’re tightening things up before anyone notices, the costs becomes internal.

What feels like protection on the surface can quietly turn into self-inflicted pressure underneath.

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Photo by Ümit Bulut

So how do we prevent this loop? It’s easier said than done. But we can do this.

In my opinion, we should aim for a shorter loop:

Awareness → Reflection → Move on.

The key isn’t to stop reflecting. In fact I firmly believe we are better human beings if we reflect regularly.

The key is to reflect with a boundary.

I’m working on asking myself, “Did I already learn what I needed for this?” Especially after it feels like I screwed up on something.

Reflection helps us grow. It’s healthy. But it eventually hits a point of diminishing return. And past that point, it doesn’t create clarity. It just keeps us in the moment longer than we need to be.

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The next time you make a mistake, give yourself some grace. Learn from the moment and let it belong to the past.

Consider following the advice from Brené Brown.

“Talk to yourself like you would to someone you love.”

Both / And is about making decisions you can live with.

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