Discover how retired financial professionals can blend sophisticated market analysis with outdoor pursuits like hiking and fly fishing, creating a fulfilling post-career life that balances intellectual stimulation with adventure.

The most fulfilling retirement transitions involve moving from success metrics to significance metrics—from accumulating wealth to creating meaning.
I am retired. I ran an RIA for 20 years as COO and CCO. I don’t want to hear about that shit any more. I do want to hear about hobbyist pursuits, hiking, fly fishing, exploring, and financial market deep dives for experts.


From Columbia University alumni built in San Francisco
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From Columbia University alumni built in San Francisco

Lena: Hey there, Miles! I've been thinking about our listener who recently retired after running an RIA for 20 years. They're done with the industry stuff but still want to stay engaged with financial markets as an expert hobbyist. It's such an interesting transition, isn't it?
Miles: Absolutely, Lena. There's this fascinating dichotomy I see with many retirees from the financial world. They want distance from the day-to-day grind but still crave that intellectual stimulation of market analysis. It's like what the Retired Investor site calls "the nastiest, hardest problem in finance" – the decumulation phase is so much more complex than accumulation.
Lena: Right! And I was reading on Bogleheads about someone who posted, "Is anyone happy with the customer service at their insurance company?" which got 80 responses! It seems like even expert investors struggle with these practical retirement questions.
Miles: You know, that's why I find the Go Curry Cracker approach so refreshing. They're documenting real-world retirement decisions – like their recent post about investing their mortgage proceeds as an inflation hedge. It's not theoretical; it's actual decisions with real money.
Lena: That's fascinating. So today let's explore how retired financial professionals can shift from managing other people's money to optimizing their own retirement while still keeping that market expertise sharp.