What Digging Holes Taught Me About Living a Meaningful Life

Craig Stanland
3 min readMay 16

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.

But those things never filled the void I felt from not pursuing my desire to create; if anything, they made the hole bigger.

Every so often, the pain would become enough that I’d get a little curious about exploring my desires,

“What did I truly want? What truly matters to me? What’s something I could do to make it happen?”

I’d start digging, and just like planting a tree, I’d strike an obstacle.

Fear, impostor syndrome, insecurities, and raging self-doubt.

But unlike planting a tree, I’d stop digging the moment I struck something and try to cover the hole like it never existed.

Digging hurt, so I stopped.

I never went past the superficial level and suffered as a result.

It took going to prison and losing everything for me to move past the superficial, to dig, and to dig as deep as I can, and when I think I’ve gotten to the…

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.