Question: If everything stays the same, what one change would create the most impact? Framework: Emerson's Definition of Success

Join me as I sit down with my friend Dr. Robert Waldinger, the director of the Harvard Study of Adult Development, which is the longest-running study on adult life, health, and happiness in the world. The study tracked the lives of 700+ original participants and 1,300+ descendants over 85 years. Dr. Waldinger's Ted Talk has been viewed nearly 50 million times and his book, The Good Life, was an instant New York Times best-seller. We dive deep into the study's most intriguing and surprising...

It all started with a simple journal prompt: Your entire life will change the moment you... A few years ago, I wrote that prompt on a blank sheet of paper. Each time I made any life adjustment or adaptation that had a profound impact, I added it to my running list. Tiny actions, mindset shifts, behavior changes, life hacks, and everything in between. The list is comprised of things I have (or currently am) struggling with. I'm not alone: These struggles are universal, but when we confront...

Question: Where am I avoiding a hard conversation that I need to have? Framework: 3 levels of listening.

The greatest discoveries in life come not from finding the right answers, but from asking the right questions. For the last several years, I've been adding to a list of questions that have changed the way I work, move, live, and love. This piece shares 7 questions that have had a dramatic impact on my life.

Question: What is one positive decision you can make to improve yourself today? Framework: Leaves, Branches, & Roots

I just completed 100 straight days of doing a cold plunge every morning. I pride myself on my consistency and discipline, but this 100-day streak pushed me to a new level. The journey included several frozen rivers, awkward interactions with hotel housekeeping departments, and one hotel requiring a lifeguard to monitor me during the plunge. I learned a lot of important lessons on the journey that have nothing to do with cold plunging (and everything to do with life). This piece shares 10...

Question: Are you listening to understand or just waiting to speak? Framework: The Law of Reversed Effort

One of the great joys of my life is that I get to spend time with some of the world's foremost experts and builders and call it work. I've recently decided that I'd like to try to record and share the insights from some of these natural conversations so that everyone can benefit from them in the way that I have. Dr. Robert Waldinger is the director of the Harvard Study of Adult Development, which is the longest-running study on adult life, health, and happiness in the world. 5 lessons from...

Question: How can I bring the after into the before? Framework: The Gold Medal Fallacy

Compounding is a magical force for growth in your life—one Albert Einstein is rumored to have referred to as the "Eighth Wonder of the World"—but it can also be your worst enemy. The stacking of negatives has the potential to knock you out of the game if you aren't careful. 3 steps to avoid the dark side of compounding: (1) Create space, (2) Evaluate the new situation, and (3) Execute.

Question: What would you attempt if you knew you couldn’t fail? Framework: The Red Team

The 2 pillars of strong relationships: High expectations and high support. High expectations are the belief that the other person is capable of excellence, that their potential is only limited by their own views. High support is the ability and willingness to provide the love, support, and engagement to help the person meet those high expectations. Both are necessary to achieve a strong relationship.

Question: What are three examples of times you've accomplished something you didn't think was possible? Framework: Circles of Success

Last week, I went on a whirlwind event tour of India. 2,000+ attendees at 6 events in 6 days across 3 different cities. I met and spent time with hundreds of people, doing my best to provide perspectives and guidance on the questions they asked. I believe that the questions are universal, so in today’s piece, I’d like to share the insights and perspectives that I offered in response to them. 6 insights from 6 days: (1) Discipline is the ultimate act of service to your future self, (2)...

Question: If someone observed your actions for a week, what would they say your priorities are? Framework: The Power Down Ritual

I'm not a morning person (at least not naturally). For most of my childhood, I'd hit snooze a million times and my mom would have to drag me out of bed to make it to school on time. In my college years, the morning hours were forced upon me by pre-class baseball practices and lifts. At first, I struggled mightily with the adjustment. I knew that if I wanted to perform, I had to figure out a system: I had to become a morning person. Somewhere along the way, it clicked, and for the last 10...

Question: How can I build my recovery into my days? Framework: The Sinatra Test

Last week, I had the opportunity to meet up for a drink with Gary Vaynerchuk, the entrepreneur, creator, and investor perhaps best known as Gary V. We were chatting about what enables this longevity, when he casually dropped a single, incredibly powerful line: "You've gotta love the dirt." The dirt is where you start. It's where you're built. It's where you find your initial success. We all start in the dirt on the journey to success, but few are willing to remain there. Few fall in love with...

Question: What is the tiny first step that will move you closer to your big, scary goal? Framework: Kintsugi is a Japanese art form that involves the repair of broken pottery with a special lacquer mixed with powdered precious metals (like gold, silver, or platinum).

I just co-hosted a retreat for a small group of very successful entrepreneurs in Cabo, Mexico. The explicit goal of the retreat was to help work through a big challenge facing each attendee. My goal is to “bring you into the room” so that you can feel the impact of the experience in your own careers and lives. With that in mind, this piece shares my 9 non-obvious learnings from the retreat.

Question: How am I creating the situation that I don’t want? Framework: The Bricklayer Mentality

Because of the gigantic shift in my life over the last three years, I'm often asked about how to take the metaphorical leap of faith. To answer that question for anyone who has asked, and anyone who might be thinking about it, here's my definitive player's guide to the leap of faith. The leap of faith you want to take in life is so scary because of the size of the change. It is a 100 foot gap from where you are to where you want to be, with nothingness in between. The 100 foot gap is the...

Question: If you knew you would die in 10 years, what would you do today? Framework: Use the Difficulty