What Digging Holes Taught Me About Living a Meaningful Life

Craig Stanland
3 min readMay 16, 2023

I was a landscaper in my teens and early twenties, and I planted hundreds of trees during that time.

The homeowner would show me where they wanted their tree planted, and I would trace a circle in the grass outlining where I would dig.

Shovel in hand and a pick at the ready, I’d break ground.

Living in the Northeast, the glaciers left behind a plethora of rocks in the soil, and I would inevitably strike one (many) of them or a root.

Little by little, I’d chip away, switching tools and changing angles until the obstruction was removed and the tree placed in its new home.

I had little choice but to do whatever was needed to place the tree where the owner requested.

I had to dig.

25 plus years later, I like to imagine how those trees have grown.

Before prison, I had a deep desire to create.

Whether it was a screenplay, an invention, or a business of my own.

It was deep inside, buried under what I thought I needed to do to be happy.

Land the coveted job title, land the marque accounts, earn big bucks, and buy lots of things.



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.