Overthinking the email you sent? Here’s what’s really going on

Digital art of a white field mouse in front of a laptop, surrounded by cheese. Generated by Bing Image Creator.

Digital art of a white field mouse in front of a laptop, surrounded by cheese. Generated by Bing Image Creator.

I'm a recovering email-checker. I could try on an email in a thousand recipient's voices. And tell you exactly what I thought they'd think.

Maybe for you it's not email. It could be your calendar. That report you sent. The meeting agenda.

Whatever it is, it really isn't about that.

When we’re revisiting and ruminating

Through hundreds of personal development conversations with others, I keep returning to the same conclusion:

Everyone wants to feel like they are doing ok.

That we’re on top of things. Prepared for whatever happens next. Especially if that might involve damage control.

So we begin searching for evidence. We check. And over-check.

This is basically a self-soothing behaviour — a self-defense against the future. Emotional armour for the unknown.

Unfortunately, it comes with a cost.

The drawbacks of over-preparedness

Keeping constant vigilance — especially over the mundane — can be exhausting and time-consuming. Aside from sapping our energy, it wastes our time.

It’s also not very effective.

If only because we’re not mind-readers. Whatever we think they're thinking, they're probably not. And we have no way of knowing for sure.

We’re just looking for a story to tell ourselves. One that that we think is most likely. Or makes the most sense to complement our carefully curated tower of beliefs.

How to stop re-reading the email you just sent

For me, making the change involved three steps:

  1. I started noticing what I was doing.

  2. I accepted the underlying need.

  3. And then surprisingly, I indulged myself. With love and limits.

Here’s what I mean by all that.

The first step to any behavior change is noticing

Before we can change course, we have to be aware of the path we’re on.

Sure, we could accidentally get to where we’re intending to go. But without awareness, we just as easily could veer right back off into the weeds. Plus, unintentional success is hard to replicate.

Next, deal with reality

I’m not suggesting you accept all reality, just the fact that, yes, this small behaviour is an issue for you right now. That it’s something you’re working on. That means it’s real, it has emotions that go with it, and you probably don’t like it very much.

The sooner we accept statements like, yes, I’m an email over-checker (or whatever it is for you), the easier it’ll be to go down the path of change. Acceptance propels us forward; resistance holds us back.

At this point, you may be telling yourself how silly you are that this is even a thing. That’s self- judgement on top of pesky resistance. Go back to step one on noticing this. Sometimes our work has layers.

Give into it (a little bit)

Behind the behavior is an unmet need. And at some point we recognise that the current behavior is a crappy way of going about meeting that need. Hence, we want to change things up.

Yet, a lot of reasons that behavior change doesn’t work is because we’re doing something different but still not addressing the underlying need. Sometimes we actually make things worse.

What if we didn’t do that?

What if we allowed ourself the moment to self-sooth? To prepare? To reassure?

With email over-checking, I found that giving myself time to re-read things, but only 1 minute. And questioning the payoff from that behaviour.

Did I really need to do that?

Was it that satisfying?

Could I do something better next time?

What we learn from our leanings

Once we understand the unmet need that the behaviour serves, we can start to find other, more productive ways to feel fulfilled.

When you build on your awareness—and do it over time—the unwanted behaviour becomes less interesting and productive to pursue.

For me, constantly checking my emails felt less like a compulsion once I recognised how the behaviour was about my need to feel like I was doing what was asked (and therefore good at my job). I was lacking information and feedback, which was leading me to doubt myself. As a result, I was searching for answers in my sent emails.

Slowly, I began seeking other, more direct ways to get the information I needed to feel secure about my work. I held onto positive feedback too, moving those emails into a folder labelled ‘Awesome feedback’. This label also means it sits right at the top of my folder hierarchy, making the cue to check it much more visible.

Putting limits on our email-checking or creating a feedback folder aren’t the only ways to go about this.

Other strategies to meet our needs

When we start to recognize that our current strategies (e.g., behaviors) aren’t serving us well, we can start trying and adopting more effective ones. Here are some ideas:

  • Talk it through with someone — conversation and connection often lend to insights in ways that thinking alone can’t.

  • Express how you’re feeling in writing, doodling or another medium — getting through the emotional cruft often clears a way forward.

  • Explicitly ask for feedback — sometimes direct is the shortest path to what we want.

  • Collect examples that reassure or validate your experience — what do you already have or know and may be overlooking here?

  • Do some research — give yourself limits and a definition of done on this one, so that you don’t inadvertently create new unwanted behaviors, such as procrasti-learning…ask me how I know.

  • Create a mini-plan of action — this can be as simple as two steps, such as “when I notice X, I will make an effort to do Y.”

Again, all of these strategies aim to support a core idea: we just want to feel like we’re on it, that we’re doing it right. Taking action that may serve us better is a huge step in that direction. We may even find that we’re already there; we just need to keep going.

Re-reading is sometimes OK…

Sometimes it is beneficial to re-check or review something. You know best where that desire is coming from. There is a qualitative difference between:

  • “Did I remember to mention the time in the email?” and

  • “Let me just re-read this again through my manager’s eyes and scan for anything that comes off weird.”

The former helps us move on; the latter may keep us stuck.

Summing things up, here are four points to consider:

  • The more you practice noticing, the better you get at it.

  • We’re never going to get where we want to go by ignoring our needs.

  • Get curious about what’s going on. Do a little digging to see what’s underneath.

  • Then let yourself get what you need, with compassion and sensible limits.

What, if anything, did you find useful here?


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