One Powerful Question to Ensure You’re Climbing the Correct Mountain

Craig Stanland
3 min readMar 7, 2022

I was a personal trainer in my early twenties. I would travel to my client’s homes, either bringing the gym to them or utilizing their home gym.

I made great money and met some incredible individuals.

I loved it.

One of my clients lived on Round Hill Road in Greenwich, CT, one of the wealthiest towns in the country. Their home was next to Dunnellen Hall, the most storied estate in all of Greenwich. It was the former home of Leona Helmsley.

I estimate that my client’s home was valued at around $10M to $12M.

They owned nice cars; their closets were filled with hundreds of thousands of dollars worth of designer labels. The art on the walls was well beyond my 20 something-year-old brain, but I knew it was special.

I’ll never forget one snowy evening, walking into their grand entrance hall and wiping my shoes on the entryway carpet before proceeding into the house.

My client’s wife told me,

“You know you just wiped your feet on a fifteen thousand dollar carpet.”

I was immediately mortified and went to apologize; she quickly said,

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Craig Stanland

I write about my journey from corporate success to federal prison and finding joy, mission, meaning, and fulfillment beyond professional and financial success.