Why High Achievers Are So Afraid of Happiness

Help! Nothing’s wrong!

Jason R. Waller
7 min readOct 23, 2020

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Photo by averie woodard on Unsplash

How do I relate my success to satisfaction and happiness? Am I chasing something meaningful or just “something”? The more I sit with these questions, the more I have to challenge myself and realize: I’m not really happy with being happy.

It sounds odd, but in my own personal development work (and in my coaching work), I’ve grown to appreciate a really important paradox: high achievers are uncomfortable with real, meaningful achievement.

We’re like dogs chasing a car — we wouldn’t know what to do if we caught it.

This sounds a little far-fetched but, let me tell you, I see it time and time again. I watch highly driven executives finally get to their next big win and what happens then? After about two seconds of celebrating, a new and often bigger anxiety creeps in to ask “what’s next?”

Let’s unpack this idea a bit, because by understanding what’s happening here we might just be able to do something about it.

We’re All Telling Ourselves a Story

While I’m talking about high achievers here, you could just as easily say “perfectionist” or “overachiever.” Not exactly the same ideas, but a lot of overlap. And all have one thing in common: like everyone, there’s…

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Jason R. Waller
Jason R. Waller

Written by Jason R. Waller

Executive coach to CEOs and leaders. Partner at evolution.team. Speaker, combat veteran, ex-consultant. Top writer in Leadership. www.jasonrwaller.com

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