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The Lie We Tell Ourselves: ‘When I’m Successful, Then I’ll Start Living’

4 min readSep 16, 2025
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I had coffee with an acquaintance recently.

We actually live in the same small town, but our only connection was through social media.

They reached out and asked if I’d be up for coffee. The idea of meeting and chatting in real life is something that’s missing from my life.

We grabbed our coffees, found some seats, and dove right in.

Unfortunately, they’d lost their very high-profile C-level position the week before. They knew I’d been through some stuff and wanted to chat.

We talked about next steps, and I asked him,

“How do you define success?”

He answered along the lines of,

“I always thought it was more money and the next big thing, the next big job title.”

I nodded the nod of total understanding and asked him,

“You achieved that definition of success, but let me ask you, did you feel successful?”

His answer was an immediate,

“No, not even close. I wasn’t fulfilled.”

Professional and financial success are only two components of our lives, yet we often make them the sole metrics for measuring our lives.

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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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