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9 Massive Mistakes I Made When I Was a Professionally Successful (but Unfulfilled)

Craig Stanland
2 min readApr 11, 2024

9 massive mistakes I made when I was professionally successful (but woefully unfulfilled).

Do any of these strike a chord with you?

🛑 I cruised on autopilot.

🛑 I was busy but not productive.

🛑 I believed my fears without testing them.

🛑 I didn’t prioritize meaningful activities I enjoyed.

🛑 I believed I wasn’t worthy of pursuing my childhood dreams.

🛑 I thought money and materialism were the paths to happiness, meaning, and fulfillment.

🛑 I believed I wasn’t capable of creating my childhood dreams without even genuinely trying.

🛑 I designed my life from a blueprint that wasn’t mine, so I was living a life that wasn’t actually mine. It was the shoulds, opinions, and expectations of others.

🛑 I didn’t try to understand the problem I was solving for and doubled down on money and materialism as the solution even though they weren’t solving anything (if anything, they were causing more pain).

I can’t change any of these; the past is written in the book of time for all eternity.

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Craig Stanland
Craig Stanland

Written by Craig Stanland

From corporate success to federal prison, I share my journey to rediscover joy, meaning, and purpose. Join me in reinventing your extraordinary second act!

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