A few years ago, I belonged to a small group of advisors where we shared our experiences. We brought in a consultant to help us better understand the psychology of the people we work with. During one session, an older male advisor shared that a client of his simply couldn't make a decision on life insurance. He then added that his wife also had a notoriously hard time making decisions. I recently found myself wondering: Why is this the case? While listening to "Mindset That U

New Canaan, CT Sometimes, my day involves tedious tasks. - I don't love it. - But when I finish, I feel good. I've realized that part of the process is turning it into a game —how can I solve this puzzle best? But more importantly, it has led me to a deeper understanding: we discover who we are through doing the work. Work is a struggle, much like working out. This past Sunday, I tackled a grueling 6-mile run in New Canaan. It was 80 degrees, humid, and full of hills up Frogt

How to Cheat on Your Boss I was lucky enough to take Alexandra and Katherine out to dinner in the city this past Monday night. We took a trip down memory lane, stopping by the Monkey Bar, where Rich and I had our very first date. We also visited the Carlyle Hotel, the venue for Alexandra’s baby shower back in 2006 — two years before the Great Financial Crisis hit. When kids are interning in New York City, they quickly learn just how staggeringly expensive it is. They start to

I've been watching my kids this summer, feeling both proud and a little envious. - My daughter Alexandra is interning at Book of the Month Club in NYC — reading books in Central Park on weekends, fully absorbing the city. - My daughter Caroline is getting ready for college, working at a summer camp and tutoring, but lit up when I suggested she learn Billy Joel's New York State of Mind on the piano. - My son Henry is coaching younger swimmers while quietly shattering his own P

Cool mom! There were some real lessons I learned out on the water that apply just as well to life on land. 1. Don't overthink it. Getting your body up on the board while keeping your balance takes a few steps: hold the sides, rise to your knees, then plant your feet perpendicular to the board. I tried to follow every step perfectly without any muscle memory to guide me, and I kept messing it up — until one of my daughter's friends said, "Don't overthink it." A few more tries

Boston's Freedom Trail I recently attended my 25th Harvard Business School reunion in Boston. Reunions are funny. We arrive carrying our highlight reels. - Promotions. - Successful businesses. - Impressive titles. - Net worth. It's easy to fall into the trap of keeping up with the Joneses. The problem is that keeping up often requires something else: - A facade. - Looking successful. - Sounding successful. Acting like you have everything figured out. Ten years ago, at my 15th

Mahjong, Money, and Art of Playing the Right Hand A few years ago, some friends invited me to learn Mahjong. At first, I was completely lost. I had no idea what I was doing. The teachers told us what to discard, explained the routines, and threw around jargon that sounded like a completely different language. Bams. Craks. Dots. Charleston. Jokers. The card looked like hieroglyphics. There I sat, staring at it as if it had been written by aliens. But that's what surprised me m

On Wall Street, traders talk about the "pain trade." It's the outcome nobody wants because they're positioned for something else. Ironically, it's often the direction the market eventually goes. Lately, I've been thinking about how the pain trade applies to life. Ten years ago, during my midlife crisis, I found myself confronting something I had spent decades trying to outrun. Carl Jung called it "the shadow." The hidden part of ourselves we don't want to acknowledge. The fea

If you’ve ever ridden a mechanical bull, you quickly learn one thing: the only way to stay on is to counteract the force. When the bull bucks left, you shift right. When it drives forward, you lean back. You don’t fight it by going rigid, and you certainly don’t just hold on and hope for the best. You read it, react, and play offense. Sound familiar? Riding a bull market is no different. When the market dips, the instinct for many is to panic, sell, and brace for impact — ess

Running through Central Park on the west side of Manhattan — the financial capital of the world, and arguably the easiest city on earth to compare yourself to others. Skyscrapers to your left. Young ambition on the right. And there I was, ten years ago, deeply jealous of a more successful friend. But in investing, we compare companies with one another to see if one is cheaper or more expensive. If there is a catalyst to either short the expensive one and/or buy the cheaper st

A student in the Emory financial planning class asked me in front of everyone: "How should I think about my career if I don't come from money?" I looked at her and said: "Your being poor is your superpower." She looked at me like I had two heads. But also backed it up with the famous line from the 1987 movie Wall Street when Michael Douglas (as Gordon Gekko) tells Bud Fox (Charlie Sheen) to avoid hiring Ivy League graduates, "Most of these Harvard M.B.A. types, they don't add

My husband is from San Diego. The movie Almost Famous is one of our family favorites — a throwback to SD in the 70s. The whole film is about a young journalist who gets the band to reveal their true insecurities. That vulnerability? It made them real. And it made the Rolling Stone article unforgettable. I've been living my own version of this the past few days. First, I spoke to Professor Usha Rackliffe, a financial planning class at Emory's Goizueta Business School my th

Beverly Hills High School Graduation 1991 The Best Lessons Came From What Mom Got Wrong A friend once asked me: "Does your mom find your posts offensive?" I told her the truth: My mom isn't on LinkedIn. But even if she was, she knows — I wouldn't be where I am today without learning what NOT to do from her. She was my anti-role model. And here's what I've come to believe: Humans can learn from others' mistakes. Watching someone else fail is a shortcut. You skip the emotional

Jackson Hole Dec 2024 The most valuable model I ever built had nothing to do with Excel. On Wall Street, I loved modeling. Not walking the runway—financial modeling (plus I'm way too short to model) Projecting cash flows. Stress-testing assumptions. Seeing a company's potential future. Now as a CFP, I do the same thing for people. Can they retire? Will they be okay? The model tells the story. But this spring break, I discovered a deeper kind of modeling. Henry went skiing in

Beverly Hills High School Pep Rally Fall 1990 I’ve been thinking a lot lately about what really drove me to Wall Street. Why I chose a world of sharp elbows. Why I was willing to compete in rooms where I wasn’t “one of the guys.” Why I stayed—and ultimately thrived—in a game that wasn’t built for me. For years, I was told a simple story: Finance is one of the best games in town. If you can learn it, play it, and stay in it—you can build real independence. And I still believe

I just finished reading 𝘚𝘵𝘳𝘢𝘯𝘨𝘦𝘳𝘴 by Belle Burden. It's one of the best books I've read on what NOT to do with your money in a marriage. Belle was married to a successful hedge fund manager. Big house. Nice life. She thought she was set. But she made 3 mistakes that cost her millions: 𝟭. 𝗦𝗵𝗲 𝗹𝗲𝘁 𝗵𝗶𝗺 𝗵𝗮𝗻𝗱𝗹𝗲 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴. All the investments. All the bills. She had no idea how much money they were spending. Clueless. 𝟮. 𝗦𝗵𝗲 𝗻𝗲𝘃𝗲𝗿 𝗹𝗼𝗼

The happiest people I know aren't doing more. They're doing less. On Wall Street, I was always running. – From one meeting to another – Chasing more titles – Looking for proof that I was enough I worked until I weighed 98 pounds. I’d look at my ring on the subway and wonder if I needed a bigger one. Everyone around me was optimizing every minute of their lives. I loved it. But I was exhausted. Here’s what I’ve learned since climbing my second mountain: The happiest people are

As we celebrated Caroline’s cum laude ceremony last night… and get ready for her to head off to college next year… I found myself thinking about one of my favorite Modern Family episodes—Phil-osophy—when Phil sends Haley off to college. So instead of Phil’s book of wisdom… I thought I’d share my own version—this time about money: Mom-ology: 10 Things I Want My Girls to Know About Money (and Life) 1. If you get dumped by a boyfriend, focus on work. When you make more money, h

NYC last summer I remember when I first got engaged. I loved looking at my diamond ring Two carats. Clear. Beautiful. I felt lucky. I had just started my career on Wall Street, riding the subway every morning as my boss did. After getting married, having babies, a nanny, and a wonderful husband, my career took off. But something funny happened one morning on the subway. I looked down at my ring and thought: Maybe I deserve a bigger one. Around me was the wealth of New York—

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