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The “Should” Life vs. Your True Self: A Midlife Reckoning

3 min readApr 18, 2025

We have 2 lives, but how often do we only breathe life into one of them?

What are our two lives?

The “Should” Life and Our Authentic Life

The “Should” life is as it sounds; it’s all the steps and actions we believe we should be taking.

Why?

To be happy, successful, fit in, and please our parents, to name a few.

It’s the hand-me-down blueprint of life.

By the time we reach the midpoint of our lives, our “Should” life is firmly established, including our career, family, and a certain kind of lifestyle.

It’s become our identity.

It’s also around the midpoint of our lives when we begin to take inventory of our lives and find something’s missing.

We’ve checked all the “Should” boxes, and yet when we do a personal inventory, we find ourselves asking through a veil of disillusionment and disappointment,

“Is this all there is?”

The reason we ask this question is simple, we’ve sacrificed our authentic selves to fit the mold of the “Should” life.

So, while we may have checked all the “Should” boxes, we’re missing authentic expression.

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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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