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.

In this home-grown edition of the podcast, I do the unthinkable:

In this episode, I talk about retirement mindset—why happiness in retirement isn’t about money but about curiosity, creativity, and purpose.

I share personal examples, read an excerpt from a book, and leave with a story of some of my clients who reinvented their lives in retirement. All that and more on successfully retired.

Rick advertises his Feng Shui episode.

I scour the corners of LinkedIn for rage bait.

We ask the question you've all been wondering, what's a good reason you should keep working with your financial advisor?

"If you don't know where you're going, any road will get you there."

The problem? 

Tune in to hear the whole conversation.

Ever heard of looking for a needle in a haystack?

But is it a good strategy?

It's no surprise to most of us that work is a big part of our identity. Whether it's at a networking event, a little league game, or the neighborhood BBQ people's first question is often "What do you do for work?" 

Listen in as Rick and I share stories of clients who have successfully found their purpose once the paycheck ends, questions we ask our clients that help them reframe their thinking in the years leading up to it, and what can go wrong if you wait too long to find hobbies outside of work. 

One of the cruel ironies of money is that if you're a really good saver, spending down your investments is a tough mental switch. 

"Money is fuel, it only serves it's purpose when it's burnt." 

Listen in on real-life stories from retirees who made that transition successfully, and ones who struggled to stick the landing. 

It's the thing they're not making any more of - and no I don't mean bitcoin. Real estate.

Adding real estate to your investment portfolio is, for many people, a huge way to accelerate their wealth. I'm saying that and I don't even have a course I can sell you on how to 10x leverage yourself into an early AirBnb retirement.

But should you own real estate in a self-directed IRA?

In this episode Hamilton and Rick break down the best ways to save for a child’s future—comparing 529 plans, UTMA custodial accounts, and joint brokerage accounts. They cover the pros, cons, and recent 529 rule changes that add flexibility, including Roth IRA rollovers. The takeaway: don’t default to a 529—match the account type to your goals, control needs, and tax situation.