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A few months ago I had to let someone on my team go. She’d been with us for two years, she was well-liked by everyone else on the team, and the reason for letting her go had nothing to do with effort. The role had changed shape underneath her, and she no longer had the skill set it now required.
I knew this conversation was coming for about three weeks before I actually had it. In that time, I found every possible reason to delay it. I told myself I needed to think it through more. I told myself the timing wasn’t quite right. I told myself I wanted to be fair and give her one more chance to prove herself, even though I already knew, with total clarity, what the outcome would be.
None of that was really about fairness. It was about not wanting to be the person in the room saying the hard thing.
What “Uncool” Actually Means
There’s a category of situations in life that offer no flattering angle.
Breaking up with someone. Firing an employee. Standing your ground in a conflict with someone you love. Being insulted, publicly or privately, and having to decide how to respond.
None of these situations photograph well. There’s no highlight reel version of firing someone with kindness, no viral clip of a breakup handled with grace, no applause waiting for you after you’ve stayed calm while someone tried to provoke you. Even done as well as they can possibly be done, these moments still cost you something.
Somebody walks away hurt. Somebody thinks less of you. You don’t get to leave feeling like the hero.
Compare that to the moments we usually associate with being mentally strong: the early morning workout, the calm meditation session, the disciplined diet.
All real, all valuable — and all rewarded.
Someone notices them. You get to feel proud, maybe even talk about it. There’s a version of “working on yourself” that comes with an audience, and a version that never will. The second one is where mental fitness actually gets built and tested.
How you deal with these uncool situations is one of the most fundamental but powerful mental skills you can develop.
Two Ways We Get These Moments Wrong
Across all four situations I mentioned, people tend to fail in one of two directions, and the direction usually depends on which kind of discomfort scares them more.
The first direction is over-softening.
- This is the breakup that gets dragged out over six weeks of mixed signals because the person can’t say the sentence out loud.
- It’s the firing that gets buried under so much positive framing that the employee leaves the meeting still unsure whether they’ve been let go or why.
- It’s swallowing an insult with a tight smile because saying anything back feels like starting a war.
The person here is optimizing for exactly one thing: not being disliked in the room. We all have the tendency to want to avoid being disliked. We don’t want to be someone who is disliked or hated by their tribe and so we do everything in our power to avoid being in a situation or saying anything that might result into people disliking us.
The second direction is over-defending.
- This is the breakup delivered with a list of the other person’s flaws, so the deliverer gets to feel justified instead of sad.
- It’s the firing handled so coldly and clinically that no human warmth survives the conversation.
- It’s firing back at an insult twice as hard, needing the other person to visibly lose before the moment can end.
The person here is optimizing for something else: never feeling exposed or overpowered.In this scenario, our survival instincts quickly come into play and we begin to operate from our fight or flight responses. To protect self, we start being aggressively dismissive toward the other person.
Both directions share the same root. Neither one is really about the other person, or about handling the situation well. Both are about managing your own discomfort as fast as possible — one by disappearing into agreeableness, the other by armouring up into control.
What was actually driving my three weeks of delay with my team member wasn’t kindness. It was the first pattern — softening dressed up as consideration, when really I just didn’t want to sit in a room with someone’s disappointment directed at me.
The Version That Actually Works
When I finally had the conversation, I did it differently than I would have a few years earlier. I said, plainly, that the role had changed and she no longer had the skill set it required. I didn’t pad it with a gigantic list of her strengths as a way of softening my own discomfort, and I didn’t rush through it coldly to get it over with. I sat with the silence after I said it instead of filling it. I answered her questions honestly, including the ones that were hard to answer. It took twenty minutes, and it was still one of the worst twenty minutes of my month.
But I left that room without needing her to think well of me, and without needing to prove I was tough enough to say hard things.
Both of those needs, if they’d been in the driver’s seat, would have pulled the conversation somewhere else entirely — toward comfort or toward control. Neither would have served her and neither would have told the truth.
The Empty Room Test
Here’s a question worth asking before any “uncool” conversation like this:
Would I handle it the same way if there were no story to tell about it afterward, and no one around to think well or badly of me for how I handled it?
If the honest answer is no, that’s worth paying attention to. It usually means part of the plan is built around managing an audience rather than handling the actual situation — whether that audience is the other person, a friend you’ll debrief with later, or just the version of yourself watching from a slight distance, keeping score.
The people who handle breakups, firings, conflict, and insults with real steadiness aren’t the ones who feel nothing. They still feel the pull toward softening or toward armour, same as everyone else. What separates them is that they’ve built enough tolerance for discomfort to let the pull pass through without letting it decide their words for them.
That tolerance isn’t built in the moments that get applauded. It’s built in exactly the moments this post is about — the ones nobody claps for, and the ones most people spend their whole lives trying to get out of quickly, one way or another.
Until next week,
Dimple V
P.S. Is there an “uncool” conversation you’ve been putting off — one with no flattering version, the kind nobody hands out credit for having? Notice which direction you tend to pull toward when you finally have it: softening, or armour. Comment below and tell me which one you recognize in yourself. I read every response.
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Mental Fitness Coaching: If staying steady in moments like these is something you want real practice with rather than just theory, our Mental Fitness Coaching Program includes live weekly sessions where we work through exactly this kind of situation together. Learn more here.