The Second Half of Life: Why Creating is Better Than Chasing

Craig Stanland
3 min readMay 11

I checked all the boxes I thought I had to check.

I had the career, the cars, the homes, the watches, the clothes, and the VIP status at the hot restaurants.

I did more than check them; I excelled at them.

But there was one box that wasn’t checked, and I was chasing and checking all those other boxes, thinking that one box would be checked one day.

I thought all those other boxes would eventually reach a critical mass and allow me to check that box, but no matter what I did, it hung over me — unchecked.

What was that one box?


And my life was empty without it.

I was chasing meaning through professional success and materialism and was too blind to see my actions would never create the outcome I desired.

So I doubled down on the chase, and when that didn’t work, I doubled down on the escapes (alcohol/materialism/sex).

I had a success-sized hole in the middle of my life and was throwing sand into a sieve.

Here’s something I learned:

Meaning isn’t difficult to create.

However, it is slightly more difficult than living a numb, existing but not living life set on autopilot where I was chasing short-term high after short-term high.

It took going to prison, losing everything, and rebuilding from scratch to learn that meaning isn’t something to chase.

Meaning is cultivated and created — and it doesn’t have to cost a thing other than time, and I can’t think of a better investment.

3 Simple Ways I Create Meaning Now:

1. Connect with nature. I get outside as much as possible and experience awe and wonder.

2. Who can I help today? Pre-prison, the world revolved around me; post-prison, I put the focus on others.

3. Life Calling. I invest as much time as possible in my Life’s Calling, which is communication — taking my experience of corporate success, federal prison, suicide ideation, rebuilding from scratch, and now living a life of mission, meaning, purpose, and…

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.