Conversation as a Superpower

When the Buffalo Went Away

I had been thinking about a quote from Plenty Coups, the last great Chief of the Crow Nation. He famously said that when the world changed so fast that “the buffalo went away,” it wasn’t just a shift—it was the end of one life and the messy start of another.

That’s exactly how I’m framing my current “Second Transformation.” Honestly, I can’t tell if this is a mid-life crisis fueled by a layoff, or if I was always supposed to end up here. The last time I went through a pivot this big, it involved a lot of couples counseling with a therapist who was basically the real-life version of the guy from Shrinking (seriously, that show is sooo good!). That’s a blog post for another time.
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The Retirement That Wasn’t

After nearly thirty years in the tech trenches at Microsoft and Salesforce, I figured I was so ready for retirement. My wife, Cat, had already retired, and I was seriously burnt out. We spent a few months the previous years experimenting with “Play Time“—eating our way through Michelin-starred restaurants globally and deciding that Hermès is essentially the only store I need for clothes (mostly because Cat loves it, but also because I’ve developed a weirdly specific appreciation for their “costly vs. expensive” product engineering).

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The Financial Reality Check

I thought I’d earned 100% play time. But after four weeks of aggressively KonMari-ing the house—which resulted in 20+ trips to Goodwill—my financial advisors dropped some “good news/bad news.” The good news: we can retire. The bad news: only if we “maintain our current lifestyle.”

Trying to squeeze a Fat FIRE dream into a “maintenance” budget felt about as safe as an 80-year-old trying to redline a Porsche through downtown Bellevue. The engine might do it, but the stress isn’t worth the thrill.
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The Problem With Too Much Time

With no schedule and no real urgency (I told myself I should probably take some time off before making any big financial decisions), I did what any rational person would do:

I opened 47 tabs in my brain and started “exploring.” I went down a few very reasonable, definitely-focused paths:

• Learned multi-family real estate development
  (maybe this is the part where I become a “real asset” guy and pretend I always liked cap rates more than code)
• Joined UHNW platforms and poked around alternative investments
  (translation: can I make even more money, but with fancier words?)
• Tried to understand estate planning and tax strategies
  (how do I keep more of said money… legally)
• Thought a lot about how not to raise a kid who assumes inheritance is a career path
  (how do I not accidentally undo everything above)

Somewhere in between all that, a slightly more uncomfortable question kept showing up:

What do I actually want to do next?

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The Coffee That Changed Direction

I pinged a former teammate from ~20 years ago—the kind of reach-out where I half expected the usual “silence”

Back then, he told me he was getting into property development. I remember thinking: ah yes, the classic “I couldn’t make it in tech” pivot. Meanwhile, I was busy convincing myself the only real money (and intelligence, obviously) lived inside technology and software.

Fast forward to coffee in Kirkland, where I was served a generous, artisanal portion of humble pie.

We skipped the usual “what are you building / doing/ disrupting” script and went straight into real life—my son, my dad, his journey in real estate (casually mentioned he was up hundreds of millions at one point, like it was a side quest), the future of white-collar work in an AI world, and the self proclaimed declaration that I was done with tech.

It was the first conversation in years where I didn’t feel like I was there to extract something—no mental note-taking, no “how can I use this later,” no invisible scoreboard.

Just… a conversation.

The kind where you walk away and think:

Huh. That felt… different.

We kept meeting after that. More coffee, more conversations—each one stretching my perspective a little further than the last. Not in a loud, “life hack” kind of way, but in a slow, uncomfortable, oh… maybe I’ve been looking at this wrong kind of way.

It’s rare to meet people who are both wildly successful and genuinely grounded. Even rarer to find someone who seems to be living life on purpose—not optimized, not maximized, just… intentional.

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The Unexpected Turn

Today, my life is reimagined through the lens of Radical Hope. The distinction between “core work” and “side projects” has effectively dissolved. I am no longer “employed”; I am now an investor that’s deployed across a portfolio of high-leverage bets:

• MistryOS.com: Tackling the unaddressed $ trillion opportunity in blue-collar and other industries ripe for AI disruption.
• Housing: Solving the housing crisis (including affordable homes) in the Pacific Northwest through modular development.
• Mentorship and Lead Investor: Serving as a product mentor for a Gen AI coaching startup, helping to humanize the world as AI redefines the nature of work.

The biggest surprise? The reading list my coach gave me. I used to think philosophy was just theoretical BS for people who didn’t have to deal with the real world. I was wrong. Books like Learning to Learn and Conversations for Action showed me that ontological philosophy is actually the ultimate operating system for building companies and how to live one’s life to the maximum.

I’m still in pure learning mode, but it’s been a revelation to find that the hardest problems in the world aren’t solved with raw intelligence—they’re solved with better conversations. I’m hoping the rest of this journey stays this insightful, even if the buffalo never come back.

For #ELF#