In this episode of Successfully Retired, I sit down with Scott MacKillop, — a true adventurer in both life and work. Scott started his career as a securities lawyer in Washington D.C., went on to lead five TAMPs, and founded First Ascent Asset Management, the first flat-fee investment platform in the industry.
We talk about what happens after the climb — when you’ve built, led, and achieved so much, and then step away to ask, What’s next? Scott shares how he’s approached that transition, the challenges of leaving behind a lifelong identity, and how he’s redefining purpose in this new stage of life.
It’s a thoughtful conversation about reinvention, meaning, and what fulfillment really looks like beyond the business world — whether you’re retired, semi-retired, or just starting to think about your own next chapter.

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