Rich and I love rewatching Mad Men. On the surface, it's about a Madison Avenue advertising agency in 1960s New York. But underneath, it's about something much deeper. It's about identity. After years of chasing success, Don Draper walks away. At a retreat in California, he admits he's been living under another man's name, breaking his vows, and pretending to be someone he isn't. Peggy Olson begs him to come back to New York and work on the Coca-Cola account. He does eventual

New Canaan, CT I used to think my story was about money. Lately, I've realized it's really about agency. As a kid, I loved Legos and hated Barbies. Looking back, I don't think it was about the toys. Barbie lived in a world someone else had already built for her. With Legos, you built your own. Later in high school, one afternoon, I came home from school to find a pink notice on our front door—our phone was about to be disconnected. I could either ignore it and hope someone el

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