How to Maximize Your Victory Frequency

For Midlife Men, By Midlife Men

Author

Greg Scheinman
March 09, 2025

Today’s Midlife Male includes:

  • ‘HOW DANA CAVALEA SEES IT’ - How to Maximize Your Victory Frequency
    → On Training World Champions, What Works with Coaching Top CEOs and How Vulnerability Breeds Doubt

  • VIEWPOINT: Ted Williams, 98 Years of Tradition & Why RIGHT NOW is the Time to Make Memories

    → The Bliss of Spring Training, Grandsons, Fathers & Sons and the Importance of Shared Passions Between Generations

  • The 6Fs (Family, Fitness, Finance, Fashion, Food, Fun)

    →Ruck When You Can, Netflix Founder on Why Work Isn’t Family, a Breakfast to Be Jealous Of and more…

Morning, Greg here! Welcome to Midlife Male, the fastest-growing, #1 newsletter and lifestyle brand for men 40+. Hundreds of readers are joining us every day for actionable, relatable, curated interviews, columns and content you’ll find nowhere else. If a fellow MLM reader shared this with you, subscribe here:

In partnership with:

I'm thrilled to introduce Dana Cavalea—author, speaker, and ex-performance coach for the New York Yankees—as our latest "How I See It" interview. Dana recently joined our Midlife Male Inner Circle community call (here’s how you can become a member!) and left us fired up with his no-BS, transparent coaching style. 

Now an entrepreneur running Freedom Farms in upstate New York, married, and with a wealth of experience from working with top athletes and execs, Dana brings a powerful perspective on midlife challenges like burnout, confidence dips, and adapting routines. His insights on performance, recovery, and life have been game-changers for me and many others. You can follow Dana through his website, his books, talks, and thoughtful daily LinkedIn posts. This is how Dana Cavalea sees it:

MLM: Dana, I came across your profile on LinkedIn and started following your content daily because it’s so valuable. Can you tell us a bit about your background and how you got started as a high-performance coach?

Coach Dana Cavalea: Thanks for having me! I’m excited to be here. I started as a baseball player growing up on Long Island, New York, dreaming of playing for the Yankees. I didn’t make it as a player, but I went to the University of South Florida and got into strength and conditioning. I worked with the football team there, and then luck struck—spring training for the Yankees was nearby. I went from snapping photos of players like Derek Jeter through a fence as a fan to interning with the team the next day. They gave me a lanyard with clubhouse and field access, and suddenly I was in the middle of the Yankees’ team stretch. It showed me how fast life can change with positioning, circumstance, and a bit of luck.

MLM: That’s incredible! You went from one side of the fence to the other so quickly. How did you seize that opportunity once you were in?

Coach Dana Cavalea: I was just an intern who didn’t know much yet, but I’ve always been a question-asker—trying to understand why things are done a certain way. That curiosity helped me later as a consultant. With the Yankees, I noticed the scouting department focused on talent but not injury risk or player potential. So I created a “Player Performance Scouting Report” to measure things like shoulder and hip mobility, color-coding risks for each player. I’d take these reports in a yellow envelope to Brian Cashman, the GM, pitching my ideas. Eventually, after injuries hit and the guy above me was fired, I moved into an interim role. It happened fast—I was in my mid-20s—but I believe it’s your job to create opportunities and then make them better by adding value.

MLM: I love that idea of creating value. Time management seems key to all this. How do you approach time as a resource?

Coach Dana Cavalea: Time is my most precious resource. I decide where and with whom I spend it, which puts me in an offensive, alpha position. I need time daily for workouts, meals, work, rest, and creative pursuits. If I carve out time for those, I’m capable of anything. If I don’t, I feel a deficit—a vulnerability that breeds doubt. I learned from players like Derek Jeter: when a weakness (like his decreasing mobility) was pointed out, he addressed it strategically with time and effort, turning doubt into confidence. Wasting time is the greatest risk, and people do it constantly.

MLM: That ties into something I say: “Show me your calendar, and I’ll show you your priorities.” I used to think avoiding planning kept me free-spirited, but I’ve learned discipline equals freedom. How do you help people prioritize, especially with strengths versus weaknesses?

Coach Dana Cavalea: I focus on internal weaknesses—the ones you feel within yourself that you know you can improve, not just tasks you dislike that you can delegate. For example, if someone’s overweight and knows they eat poorly, that’s a weakness they wrestle with daily. They need a plan—eating structure, training schedule—baked into their day to automate change. As for strengths versus weaknesses, it’s not all-or-nothing. Strengthen what makes you vulnerable if it’s holding you back, but double down on strengths where you can. The key is identifying what’s diminishing inside you and scheduling time to fix it.

MLM: For someone who knows what to do but doesn’t act—like the guy who’s out of shape—how do they bridge that gap to become a high performer?

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Ted Williams, 98 Years of Tradition & Why RIGHT NOW is the Time to Make Generational Memories

By Jon Finkel

My grandfather spent all eighty four years of his life as a die hard Red Sox fan and at one point, every player on the team was a bum. Every manager was no good. If the Sox were down by a few runs, regardless of inning, it was over. Down three-to-one in the bottom of the 2nd? Game’s done. Down four-to-two in the fifth? Forget it. Of course, he spent the bulk of his life in the midst of the 86-year “Curse of the Bambino”, where the Sox always choked and never won a title. But still, his pessimism was legendary:

Pedro Martinez? Great pitcher. Bum. David Ortiz? Amazing hitter. Bum. Jason Varitek? Incredible leader. Bum.

He hated every manager from John McNamara to Grady Little (really hated Grady, as we all did). He tolerated Terry Francona. Yep, World Series winning, curse-breaking Terry Francona.

But all this negativity about his favorite team?

It brings a huge smile to my face. 

And to the face of my dad, his son (now 74). And to my brother’s face. And to our kid’s faces (12, 11, 9) as we reminisce about Papa Finkel, my grandfather, who died before my kids and my brother’s kids were born. He was a funny guy. Great storyteller. Hard ass. Big forearms. Sold meat for a living. Old school.

This past Sunday, while sitting in a row at a Red Sox vs. Mets Spring Training game with my dad and my brother and our kids in Fort Myers, doing impressions of my grandfather (he really hit the ‘B’ hard when he said bums), it occurred to me that our Spring Training trip in 2025 wouldn’t have happened if in, say, 1938 or so, my grandfather didn’t fall in love with the Red Sox and make them his team. 

Because if he wasn’t a fan, maybe he wouldn’t have raised my dad to be a fan and maybe my dad wouldn’t have raised me and my brother to be fans and now, nearly one hundred years later, maybe we wouldn’t be raising our kids as Red Sox fans.

It’s insane to think about the length of time we’re dealing with here. 

We’re talking about a near century-long family bond across four generations because 13-year-old Donald Finkel in Roxbury, Mass was mesmerized by Ted Williams’ swing.

And sure, some like to dismiss this stuff with a trite, “it’s just sports.”

And if you say that, you have no idea what you’re talking about.

Because when it comes to favorite teams passed down from dads to kids through the years, sports are almost certainly about way more than sports. They’re part of the fabric that unites generations.

Take a walk around a baseball stadium during a Spring Training game. Any time. Any town. And what you see is the best of what sports can be from the spectator side.

You’ve got fathers and adult kids sitting in the seats reminiscing about the games they went to over the years. You’ve got grandfathers explaining the game to their grandkids, filling out scorecards. You’ve got grandparents and parents and young children wrapping their arms around each other to sing “Take Me Out to the Ballgame.”

You’ve got joy. You’ve got happiness. You’ve got lifelong memories happening in real time. And it hits every generation simultaneously. 

If you’re a nine-year-old kid who loves baseball, what could be better than going to the ballpark with your dad and grandpa?

If you’re a grown man and you have a kid who likes baseball and a father who is still alive who likes baseball, what could be better than going to the ballpark with your dad and your kids?

And if you’re a…

I love this comment from Reed Hastings because I’ve long believed that corporate culture is mostly bullshit. Nearly every company on earth will fire you at the drop of a hat if they can save money by replacing you or finding a cheaper alternative. That’s not family. That’s cutthroat business. Don’t mix the two. - Greg

Ruck When You Can

We’re now fully into Spring sports for the kids and now twice a week I’ve got my son at one end of our town’s sports complex working on his Tae Kwon Do (high blue belt) and my daughter completely on the other end at beach volleyball practice.

Instead of hanging to watch just one, I decided to make a little ruck out of it. I grabbed my pack and now I walk a nice 45 minute figure-eight loop along a trail from the window into the Tae Kwon Do class to watch my son and along the courts to watch my daughter. Everyone wins.

If this seems like an awesome idea, and you don’t have a pack, visit GoRuck’s website HERE to grab yours. - Jon

We made a huge announcement this week that we’re pumped to share with you all. You can check it out in the link above. As you all know, the conversations and content at Midlife Male are relatable, credible and aspirational, and that's why they resonate and why our backing continues to grow. Men need this and it's our mission to meet them where they are and give them what they need - and we're just getting started. Thank you for all the support. We're changing the way men see and live in middle age and we’re grateful to have you on board. - Greg

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Join the Inner Circle

The MLM Inner Circle is a community for midlife men, by midlife men. Our members are accomplished men over 40 looking to level-up across every area of their lives.

Some have been married for decades, others are divorced, most are fathers. All of our members seek improvement, access, insights, and support in a group of like-minded men. They are committed to making the next phase of their lives, the best phase of their lives, living happier, healthier, wealthier, stronger and having more fun in business and in life.

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MLM Founder: Greg Scheinman / Follow Greg on Instagram & LinkedIn

“You either define midlife, or it’ll define you.” - Greg

MLM Editor-in-Chief: Jon Finkel / Follow Jon on Twitter/X and Instagram

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming.” - Teddy Roosevelt

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