252. The Mid-Career Solopreneur Myth That’s Holding You Back

In this episode, Will Simpson gets honest about the moment he realized he didn’t want a boss. He breaks down the identity crisis that hit after leaving decades of COO/CTO life, the surprising advantage founders over 40 actually have, why solopreneurs must unlearn corporate thinking, and how embracing “good enough” is the key to launching anything.

If you’ve ever wondered whether you’re too late, too structured, too corporate, or too unsure to build something of your own…this conversation is the permission slip you’ve been waiting for.

FAQs From The Episode

What makes this episode valuable for solopreneurs who come from the corporate world?

Will explains exactly why corporate experience does translate, just not in the ways you think. He talks through the mindset traps, the “ambient stress” you leave behind, and how to rewire yourself for small-ball thinking, fast execution, and building something that actually energizes you.

Does Will think it’s harder to become a founder after 40?

Not at all, he argues the opposite. According to Will, founders over 40 bring unmatched domain expertise, resilience, and clarity. The data supports it, and he shares why experience gives mid-career professionals an overlooked edge that younger founders simply can’t replicate.

What’s Will’s top advice for solopreneurs who want to use AI or no-code tools?

He stresses that AI can help you build prototypes fast, but not without structure, constraints, and actual expertise guiding it. He breaks down why you can’t “speak” a fully functional app into existence, how to think like a builder instead of a coder, and why you should ship an MVP that’s slightly embarrassing.

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