Financial Wisdom from a Retired Catcher

Nick Levinson Life with Money

This edition of Life with Money is going to involve a lot of baseball talk. This may thrill you or bore you, but I promise that after the history lesson and personal reflections, there will be some relevance to personal finance.

Baseball and Mitt

Baseball has been an important part of the Levinson family for many years. Vic was a Brooklyn Dodgers fan who converted to the Yankees when the Bums moved to Los Angeles in the late 1950s. He coached me and Tom in little league in Tenafly, New Jersey, and Riverdale, the Bronx. I also helped coach a few of Tom’s little league teams before he moved on to pitch for the Horace Mann Lions in high school.

We were staunch Yankee fans growing up, suffering through the Horace Clark/Fred Stanley era before George Steinbrenner (love him or hate him) brought us the late 70s teams of Reggie Jackson, Thurman Munson, and Catfish Hunter. We struggled some more with Dave Winfield and Don Mattingly in the 80s and early 90s, before being blessed with the four-time champions led by Derek Jeter, Mariano Rivera, Jorge Posada, and Bernie Williams. Despite all of the money lavished on players since then, there’s only been one championship in the last two decades.

For me, fandom turned closer to home. I had the great pleasure of coaching Nate (going on 25) and his two brothers, Owen (almost 22) and Ben (turning 20 this Sunday!) from the ages of about six through 13. We got to share the thrill of victory and the agony of defeat, and I’m sure I learned more from them about being a parent and coach than they learned from me about baseball. With better coaching leading up to and in high school, they all went on to play for the Piedmont (CA) Highlanders. Nate moved on to catch at Macalester College, Owen is currently an infielder for Case Western Reserve, and Ben is pitching, also at Macalester. Julie and I have been extremely fortunate to see most of their high school games and many of their college games, and we look forward to the four seasons remaining for Owen and Ben.

Baseball is loved (and hated by some) for its slow pace and time for contemplation, and in this spirit we read with interest a recent New York Times article about retired major leaguer John Jaso. Jaso was not a star but a solid catcher/first baseman for four teams in his nine-year career. He caught a perfect game (no hits, walks, or errors allowed) and hit for the cycle (single, double, triple, and home run in the same game). But the most interesting thing about Jaso from our perspective is that he walked away early from a lucrative career to spend his retirement (at least so far) sailing.

Jaso retired at the end of the 2017 season and hasn’t looked back. “Sometimes I’ll just be out on the boat bobbing in the water, not sailing or even fishing, and I’ll think to myself: ‘There’s nowhere else on the planet I’d rather be than right here. It’s been the perfect fit for who I am.’”

He enjoyed playing professional baseball, but not everything about it. “Baseball set me up for life. I love it, and I respect it. But it was part of this culture of consumerism and overconsumption that began to weigh really heavily on me. Even when I retired, people said, ‘You might be walking away from millions of dollars!’ But I’d already made millions of dollars. Why do we always have to have more, more, more?”

Jaso craved a less complicated, less materialistic life. “I want my life to be simple, and it doesn’t get simpler than being on a sailboat. You treat the boat right, and she treats you right. That’s all there is to it.” He added that “when you’re sailing, you’re going back to something primitive. You’re removing yourself from the material world – this concrete, electronic world. And you’re returning to this sense of wonder. It’s the same sense you get when you’re holding a newborn baby, looking into their eyes, and feeling the world disappear around you.”

In addition to his poetic sentiments, we think Jaso has hit upon a few important concepts related to financial advice and the way we provide it to PPA clients:


Jaso was of course fortunate to earn almost $20 million dollars in his playing career, but at the age of 34 he realized that he didn’t need more for the sake of having more. He focused on what made him happiest and has avoided other materialistic pursuits. This is a concept we often discuss with PPA clients. At some point (and this is of course different for everyone), you have enough money to live the rest of your life, and in many cases to provide for children and grandchildren as well. Once you’ve reached that level, you can afford to take less risk in the markets, focusing instead on capital preservation and income generation. If you’re still working, you can pursue a volunteer or non-profit opportunity if that’s important to you. Helping clients figure out what’s enough for them is a vital part of what we do at PPA.


This is related to the concept of enough. At some point, having more possessions and commitments can become a burden rather than a joy, as Jaso’s experience demonstrates. In many cases, pursuing and having fewer things can make the time you spend on them more precious. There’s nothing inherently wrong, of course, with complexity, but we encourage clients to focus on what’s really important to you.


Jaso got his sailboat, but since then he’s been sailing and enjoying other experiences. He and his girlfriend sailed for three months in the Caribbean in 2022. He’s also “taken several trips to Europe, discovering a passion for exploring his father’s ancestral land in the Basque Country of Northern Spain. And he has driven a camper van around Australia and Indonesia.” These might not be your preferences, of course, but the key is to figure out what you really like to do, and do it as much as possible. If you can bring family and friends along to share in the experiences, even better. We advocate for clients setting aside funds to travel, pursue hobbies, and get involved in the local community. As we’ve written before, numerous studies have shown that you’re more likely to treasure the memories from a great experience than merely having another possession.

If you’re interested, please don’t hesitate to bring up any of these ideas the next time we’re discussing your personal situation. And we’ll let you know how Case Western and Macalester do this season.

Read “Financial Wisdom from a Retired Catcher” in the Piedmont Exedra.