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Then and Now: How I Make Better Decisions

Craig Stanland
4 min readJun 23, 2024

It was around October 2012 when I made the choice that would shatter my life.

I was a successful Senior Enterprise Account manager for a large tech firm, working with some of the world’s most prominent banks and hedge funds.

The products I was selling were becoming commoditized, profit margins on deals were razor-thin, and my paychecks were shrinking.

I was so caught up in living a luxurious lifestyle that I was not working as hard as I should have been, and my paychecks were shrinking.

I was living an inauthentic life and felt empty inside, but I believed the luxury would eventually fill the void.

My identity, self-worth, and sense of adequacy became inextricably interwoven with my money and materialism.

Shrinking paychecks threatened to strip my identity away, leaving me exposed, and one of my greatest fears brought to light:

I was, in fact, unworthy and not enough.

My vision was sucked into a tunnel, with only two options available.

1. Be honest with myself and my wife at the time and admit that I couldn’t afford the lifestyle anymore and wanted to do something different.

or

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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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