Middle aged Nice Guys

There’s a lot of different types of Nice Guys, and there’s a certain type that come to me for confidence and integrity work in their middle-age, late 30s, 40s, sometimes 50s.

These are a particularly unfortunate type of Nice Guy. The reason they come to me later in life is because being nice has actually kind of worked well enough for them over the last few decades that it’s never really hurt enough to make them want to change.

Like slowly boiling a frog in water, they couldn’t quite see that they were being cooked.

They only come to me after the big crisis finally happens.

I was lucky. I had my crisis when I was in my mid-20s. It hurt sharply enough to want to change this shit early.

But had I done a bit better with women, and perhaps succeeded a bit more with money or something, I might have just kept going with that strategy for even longer.

I often imagine if my first proper girlfriend hadn’t left me, I probably would have married her and ended up getting divorced like 10-20 years later, like many of my clients who end up getting divorced or having a career crisis in their 40s.

So one thing you’ve got to be wary of if you’re a people pleaser and it’s working “well” (people often like you and you’re mostly comfortable): The crash is going to come later but it’s going to be much bigger.

And no matter how “well” people pleasing seems to be going for you, the crash is still going to happen. You simply cannot be fake for decades and hope that it will end in psychological wellbeing.

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One Response

  1. Usually the quickest way to break this cycle early is to commit to being honest about your preferences, no matter the reaction.

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