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?
Coach Dana Cavalea: Change is sticky at first, like untangling a knotted ball of yarn. If you’ve never done it, get help—admit you lack accountability or a plan. Too many fail trying to do it alone. Start by deciding, “I’m going to optimize myself,” then find someone to guide you. Over time, it becomes part of who you are—the champion version of yourself. Physical training builds mental discipline too; it forces effort and confidence. I had Yankees players work out before games—not to tire them out, but to boost how they felt about themselves going into competition.
MLM: That’s a great idea. I do something similar: I schedule tough tasks right after workouts because I feel unstoppable then. How do you help people stack the deck in their favor like that?
Coach Dana Cavalea: It’s about strengthening your alpha—putting yourself in a dominant position. In sports, it’s me versus you; someone wins, someone loses. You stack the deck by training physically and mentally to maximize your victory frequency. For example, a client selling his company for a billion dollars met private equity guys on the golf course—where he excelled—making them see him as a leader. If mornings aren’t your best time, don’t schedule key meetings then. Set terms that favor you.
MLM: That’s proactive versus reactive. For midlife guys who’ve been reactive—pleasing others, not setting the table—how do they shift to offense?
Coach Dana Cavalea: Pull the emergency brake. Too many keep doing things the same way, even when it’s not right for them anymore, chasing false safety or money they could replace. Perception—like worrying how a CEO will view you if you reschedule—imprisons people. Say no, set your terms, and stand out. I tell people I wrestle alligators for a living—working with dominant, ego-driven men, crushing those egos, and refocusing them for real dominance without internal struggle.
Greg Scheinman: That brings up something I wanted to cover. You’ve transitioned from coaching Yankees to CEOs. How did that shift happen?
Coach Dana Cavalea: I used to give CEOs power based on their title, but I realized everyone’s just human behind the jersey or the desk. Athletes and CEOs have similar issues—different toughness thresholds, sure, but the same need to optimize. Athletes handle public failure better; CEOs often control to avoid it. My philosophy is: meet them where they are and help them improve from there.
Greg Scheinman: Who’s the typical person reaching out to you now?
Coach Dana Cavalea: High-expectation guys—often men with huge goals but timelines they can’t meet. They feel their confidence slipping, sense threats behind them, and wrestle with anxiety. They’re driven to leave no potential untapped, ensuring their legacy reflects excellence in their personal life, family, and business.
