My next book will focus on the launch decade—the now-extended era spanning ages 16 to 26 during which young people work toward financial independence. The phrase “failure to launch” has become so commonplace that it may no longer carry the heavy impact it did just a few years ago. To be clear, launching does not […]

Twenty Years In: What Actually Separates Our Biggest Successes I’ve been working with young adults for over two decades now. In that time, you start to notice patterns — not hunches, but real, repeatable conclusions about what separates the students who thrive from the students who merely get by. Two of those conclusions stand out […]

I remember working with John, a junior at Guilford High School in Connecticut, who possessed what I would call latent ambition. He wanted to accomplish something significant, but he did not yet know where to direct his energy. John had performed reasonably well during his freshman and sophomore years, but his sophomore-year PSAT score of […]

Connecticut Juniors: The PSAT Is the Real Kickoff to College Yes. I know. School has just started. If you’re a parent in Connecticut, school this week probably felt a bit overwhelming, both to you and your children. Some of that might have been fun, some of that might have been exciting, and, unquestionably, the busyness […]

It’s late August, and if you’re a Connecticut parent right now, you probably recognize this feeling: the calendar just got very full, very fast. Fall sports tryouts. Back-to-school nights. New teachers to figure out. Course schedules that don’t quite make sense. A rising junior who suddenly needs to think about the PSAT. A rising senior […]

I have taken on a handful of clients in the last few years: young adults – these happen to be young men – who are not meeting with me for “help” through a challenge but rather to affirmatively build their future. They are doing incredibly well. Much like it is with coaches of top athletes, […]

High School Kickoff: Navigating the Launch from Day One The transition into high school marks the official start of a student’s high-stakes developmental runway. For parents along coastal Connecticut and across the state, this moment often brings a mix of excitement and quiet anxiety. The cultural conversation surrounding college admissions, shifting career landscapes, and post-secondary […]

I was working with Tim and Janet, two kind parents from Madison, Connecticut. They had worked hard to provide their children with good lives. Neither of them came from money, and both paid for their own schooling. For that reason, they knew the value of a dollar. They also had a later start on wealth […]

When I wrote Motivate Your Son more than ten years ago, I made a prediction about the future of young people. I divided them into three broad groups: 10% would be on the path of abundance. 40% would be on the path of struggle. 50% would be on the path of disaster. These were not […]

Several summers ago, parents from Old Lyme, Connecticut, came to see me in something of a panic. Their oldest son—I’ll call him Jason—was about to begin his junior year of high school. Jason was athletic, bright, social, and generally a good student. But his parents didn’t like the direction he was heading. He had begun […]