As we head into spring break, I had a small breakthrough. Yesterday I presented to the Harvard Business School Women’s Association. They reached out after I posted an article about my career pivot and the lessons I learned along the way. The title of the talk: From Net-Worth to Self-Worth: What Markets Taught Me About Identity, Loss, and Personal Alpha. I told the truth about the dips and valleys in my life and career. I talked about not avoiding pain — because if you lean in

I was running along the banks in Boston, leftover snow crunching under my feet. Cold. Dry. But there was light. I was there on a college tour with Caroline. And something hit me mid-stride: I sometimes feel frozen.  This is a turning point.  An ending, yes, but also a brand new beginning. Previously, we attended a rehearsal for Cambridge Common Voices. The energy in that room — voices blending, harmonies swelling — was electric. The kids loved having Caroline there. And watch

New Canaan, CT Men's Club What I Told Men in New Canaan About Their Wives and Money While everyone knows there are two certainties in life: death and taxes. There's a third topic most couples hate discussing even more. Money. Tuesday, I spoke to my dad's men's club  (after my snowy run in Old Greenwich) —a room full of retired guys who've spent decades building portfolios. The topic?  How to talk to your partner about the stock market and money. I started with a question: Wha

Last year, Kiki and I stood at the top of Tower Three  (a Double Black Diamond run at Jackson Hole). The run looked terrifying — steep drops, trees, rocks, no easy way down. We could've taken the groomed trail. The safe route. Instead, we pointed our skis downhill and went. That's how I've come to see most of life's big choices. Ten years ago, I sat down one night and drew something (A Decision Tree) that quietly shifted everything. Just two possible trajectories on a piece o

(Photo: Henry noticed where my attention was and took one of my 6 CFP books I was reading to pass my Certified Financial Planning exam. ;-)  Greenwich → Houston → Atlanta. Each move for Rich's career meant starting over.  New city, new schools, zero network. But the real kicker came when Morgan Stanley held Rich's stock plan. As a "courtesy," they assigned us a financial advisor. When Rich kept dodging the guy's calls, he finally said, "Just talk to my wife." I was between ca

The world is constantly giving you feedback. Most of us just don’t slow down long enough to listen. A few weeks ago in Nashville, I put my whole life on hold for Caroline’s audition. And the experience taught me more about lanes, identity, and money than I expected. The Moment Everything Got Quiet The producers kept asking her:  “Are you country?  Are you pop?  What’s your style?” Caroline said the truth — she likes to sing everything and she appreciates all kinds of music. B

boat to Martha's Vineyard (2019) Six years ago — summer of 2019 — we were having dinner with close friends from Houston on Martha’s...

Fearless Girl When I worked at a hedge fund, pitching investment ideas to my boss was an adrenaline rush. I’d research a company, prepare...

(Like parallel park between two Porsches—one worth $700,000) I used to think my childhood struggles were unique.  But as I’ve gotten...

My high school year book title ;-) I used to walk from my mom's crappy apartment to Beverly Hills High School and pass by the tiny stucco...

I love March.  Spring is coming, and the weather is getting a little warmer. I grow to miss the cold winter days of my runs because I...

During a quiet three-day weekend, I discovered the ultimate way to think about taking a chance and if something in life is worth it.  I...

Photo is of me as a teen in Africa where planes land on grass with no pavement Many of us suffer from anxiety, and it’s hard to figure...

(photo credit to one of my kids while I was thinking deeply at lunch in La Jolla)  When A.J. Brown, a Philadelphia Eagles wide receiver,...

Early settlers in the North had to figure out ways to stay warm. That discomfort drove innovation. It makes me wonder about the recurring...

Every Christmas, we head to California to visit my college friends  Torrey McClary  and  Elissa Brown  and Rich’s parents. This year,...

I love finding inspiration from movies!  This vlog is all about rethinking how we can break free from the rat race and uncover the truth...

On a cold December morning, I found myself wrestling with the concept of leadership—not in the traditional sense of leading others, but...

Going to Beverly Hills High School was surreal -  It was the time of the hit show 'Beverly Hills 90210',  the movie 'Less than Zero', and...

Over Fall break, we attended a beautiful wedding, visited a college in Connecticut, and, of course, spent some time in New York City....