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I Won

Posted on April 8, 2024April 9, 2024 by Steve Ainslie

I was listening to a podcast last week about the grind and hustle involved with building a business. The speakers worked hard (and got lucky) and as a result, had made millions from their businesses while attaining a modest level of fame and accolades. They had already attained success and were expanding their businesses.

As I was listening, I felt a little wistful. When I was working for startups, I was driven to “change the world” and “make an impact”. I had dreams, goals and ambitions. It was exciting and intoxicating and energizing. I thought I could accomplish anything through hard work, intelligence and effort.

I was driven by a desire to ensure my wife and kids would be financially secure and taken care of. I wanted to experience the freedom I imagined would come with being in charge and wealthy.

But, despite my best efforts, I never did make millions of dollars. Nor did I become the founder or CEO of a wildly successful business.


And then, as I listened some more this thought came to me:

I’ve already won.

I retired at 50.

I worked my way up from minimum wage service jobs into a career that spanned high paying tech sales & management roles despite my lack of a college degree.

I dug my way out of poverty, a chaotic upbringing and what should have been a series of low-paid jobs burdened by a lifetime of insurmountable debt to a stable, solidly middle-class lifestyle.


I played the game. And due to circumstances, hard work, luck, frugality, good timing and lifestyle choices, I don’t need to replay it again.

I’ve already won.

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