Redefining Success: Lessons From a Life of Wealth

Craig Stanland
4 min readDec 13, 2024

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. The work had meaning, purpose, and a deep sense of fulfillment.

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, one of the most storied estates in all of Greenwich.

I estimate that my client’s home was valued at around $12M to $15M.

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,

--

--

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!

No responses yet