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I Wasn’t Enough, So Enough Would Never Be Enough

Craig Stanland
2 min readApr 1, 2024

Pre-Prison, I was playing basketball, hoping to score a touchdown.

That’s a funny way of saying I knew what I wanted in my life, but I wasn’t taking action to support it.

I was playing the wrong game and expecting a different outcome.

I said I wanted freedom and was trying to buy it through a lifestyle of excess.

The idea was this,

“When I achieve the lifestyle I want, then I’ll have the freedom to create what I want.”

There are several significant issues with this:

I didn’t know I was enough, so enough would never be enough.

Since enough would never be enough, the goalpost was a moving target. Acquire a level of success;

“Oh, it’s not quite right; maybe when I achieve more.”

I didn’t need financial or lifestyle freedom to create what I wanted; I needed emotional freedom to pursue my dreams.

When I told myself, “When I…, then I…” I was telling myself I wasn’t worthy, adequate, or capable.

I capitulated to fear.

We’ll never find freedom on the other side of “having” enough.

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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!

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