In investing, you can't earn high returns without taking risks. If making 10% a year were easy and risk-free, everyone would do it. But what about investing in ourselves? I've been thinking a lot about money lately. Specifically, whether money motivates us to develop our talents—or actually gets in the way. As a teenager, I lived on an allowance. I hated the constraints. I couldn't buy everything my friends could. But those constraints taught me how to make decisions, how to

You Can Just Do Things by Cate Hall. Rarely does a book move me from thinking to doing. This one did. I love Cate's storytelling. Cate went from an elite legal career to becoming the world’s top-ranked female poker player, then through addiction and rebuilding her life. Along the way, she explores how we develop agency. For me, agency means recognizing that I can make a choice, take a step, and influence what happens next—even when I can’t control the whole situation. Sometim

Last Friday was not a particularly good day. I went to Pigskin Picnic at Westminster. Henry didn't really want me there. I looked around at all the younger kids and parents and wondered, What am I doing here? Earlier that week, a longtime client had passed away. The call telling me the news came from a nephew who wasn't particularly kind. By Saturday, I felt empty. - I could learn to play golf. - I could go shopping. - I could find another hobby. - I could certainly find more

New York, New York “If I can make it there…” Favorite line from the song, New York, New York by Frank Sinatra Returning to New York to speak at a conference a few days ago terrified me. I had once “made it” in New York —or at least I thought I had. And when I left, I worried that I might never make it anywhere else. My talk was about Steve Jobs’ famous idea - We cannot connect the dots looking forward; we can only connect them looking backward. Afterward, several men came up

About ten years ago, I got stuck. From the outside, my life looked pretty successful. But inside, I knew something wasn’t working. I had spent years building a life that looked good on paper, yet increasingly felt as though it had been underwritten by someone else. I needed to make a change. The problem was, I didn’t really know how. So I started to invest in myself—and I read a ton of books. Grit. Originals. The Edge. Think Like a Monk. Presence. The Subtle Art of Not Giving

At surf camp in Portugal. My career on Wall Street was a bit of a random walk. I started in investment banking because it seemed like the best place to learn about companies and finance without going to business school. And honestly, I liked the people. They were cool nerds. After business school, still not totally sure what I wanted to do, I went back to banking at Goldman Sachs because it seemed like the right path. But eventually I realized something about myself: I didn’t

Growing up in LA, my friends and I went everywhere. Before we could drive, we took buses, cabs or walked. Once we could drive, we’d head to parties in the Valley using a Thomas Guide to figure out where the hell we were going. I was the opposite of Clueless. (Great scene in the movie Clueless, the kids are using Thomas Guide to find a party in the Valley, just like we did :-) We all had a pretty good sense of direction because we had to. When my dad moved to Tokyo, I would sp

Georgetown. There's a scene in Mad Men where Peggy Olson watches a focus group of women trying on lipstick. There are dozens of shades sitting on the table. Why? Because every woman wants to find her color. I think about that scene a lot when I think about why my business has grown. Big companies need models. They need systems. They need to create models that clients fit into because that's how you scale. But people don't want to be put into boxes. They want to feel understoo

Houston, TX. When Caroline started violin at 3, it was painful. Private lessons were $25 for 30 minutes—which felt like a lot in 2011—and half the time she was rolling around on the carpet instead of listening to her teacher. I wanted to quit. It was embarrassing. It felt like a complete waste of time and money. But something inside me kept saying: I want her to learn how to do hard things. A few years ago, I thought about this while visiting a dorm at UPenn. I couldn't belie

Nantucket After a fun summer of traveling, visiting friends, and working on building my platform, I'm happy to be back home in Atlanta. This photo was taken outside the Handle Bar on Nantucket, which feels oddly appropriate for this time of year with the kids headed back to school and college. Because as we enter the second half of life, do we really have a handle on what we want? For years, one of my dreams was to own a second home on Nantucket. Nantucket—or ACK—holds some o

Nantucket and my mom's old house but renovated This week I’m visiting family and friends in Connecticut and Nantucket, and I couldn’t help but think about the childhood memories that shaped me. Back then, Nantucket was where so many New Canaan families spent their summers. To me, it represented a world I desperately wanted to belong to. One memory still makes me think and reflect. I was in fifth grade and wore my favorite Marona rugby shirt—the “it” brand at the time. By pure

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