How to Make a Mid-Career Change (Without Blowing Up Your Life) w/ Jake Kennington

How to Make a Mid-Career Change (Without Blowing Up Your Life) w/ Jake Kennington

February 17, 2026 · 44 min · Episode 66

About this episode

Don Ross and Jake Kennington discuss recognizing the right time for a career change and how to navigate that transition wisely.

Every man hits a moment in his career when he wonders: Is this really what I’m meant to do? In this episode, Don sits down with Jake Kennington, a structural engineer turned coach, to talk about how men can recognize when it’s time for a career change — and how to make that pivot wisely. You’ll learn: • How to know the difference between a rough season and a wrong path • Why success on paper can still leave you empty • How to redefine success and build a life that fits your ...

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