Rod Stewart once sang, "I wish that I knew what I know now, when I was younger." I’m humming this to myself now as I close out 2025. Turns out, the guy was onto something (even if I can't carry a tune to save my life).
Here's the thing: moving from a high performer to an effective leader requires unlearning bad habits and adopting a learn-it-all mindset. Leadership development isn't about having all the answers. It's about being willing to fail, adapt, and grow.
And boy, have I failed. But I’ve also adapted and grown.
Kind of like the 12 Days of Christmas song we are all hearing right now, I want to share 12 truths I know now that I wish I knew earlier in my career. Think of these like gifts from my failures and adaptations (but no partridge and no pear tree).
These brutal truths shaped my journey from professional baseball player to receptionist to CEO of Learnit. My hope is that you can avoid these challenges and be more successful than you even are now.
The Brutal Truth: Time is your only non-renewable asset.
We can find more friends. We can make more money. We can even reclaim our physical health by changing our habits. But when it comes to time, once it's gone, it's gone.
The Leadership Lesson: Stop being the organizational bottleneck and learn to delegate to empower your team.
When I was growing up, I followed after my grandfather, Frank Lembi, who was legendary for putting in 60, 80 hours a week. I wanted to be like him. What I didn't realize at the time is that doing everything yourself doesn't make it the best way to get things done. By delegating to people around you, especially those with more strengths in certain areas, they learn more, trust you more, and you free up time to focus elsewhere.
Three quick time management priorities:
The Brutal Truth: Financial stress limits your leadership capabilities.
I wish they would have taught this in high school or college. If I had learned financial literacy early on, I would have saved tens of thousands of dollars. I made so many mistakes: buying things I couldn't afford, picking up checks for people who weren't even my good friends, thinking I could figure it out later.
Five pillars of financial literacy for leaders:
The Brutal Truth: Emotional decisions create long-term regret.
I'm pretty famous for buyer's remorse. You make a decision, buy something, and then a week later you're like, "Oh my gosh, why did I do that?" When I reflect back, it was because I had emotional energy and just didn't think through the whole situation.
The Tool: Purposeful Awfulizing. When facing a big decision (buying a house, hiring a COO, entering a relationship), think about the worst-case scenario one year out. If things go completely bonkers, can you overcome it? If you're unsure, step back and reflect. Are you thinking with a clear head or are you pumped up and ready to make a decision you'll regret?
Most major decisions don't need to happen automatically. Stop, reflect, walk around the block, talk to somebody. Take your time.
The Brutal Truth: Failure isn't the problem; avoidance is.
I failed so much in baseball, but even then I worried about what people would think. What I didn't realize is that growth only really happens outside your comfort zone. One of the biggest failures is just not trying at all or giving up too early.
Some of the best leaders I've interviewed aren't afraid to stick their neck out there and try. Every situation is a learning opportunity for leadership development. Get comfortable with failure.
The Brutal Truth: Don't stay stuck in bad jobs, habits, or relationships just because of time spent.
It's called the sunk cost fallacy. Don't feel like just because you've put time into something, whether it's a miserable relationship or a job where you're not enjoying yourself, that you have to stay. Otherwise you're going to look back and say, "Why did I stick with this for so long?"
I was like that with relationships. I was like that with some employees we kept around at Learnit that I knew weren't the best fit. The first step is just realizing you need to make a change. Don't stay stuck.
The Brutal Truth: Life and leadership rarely go as planned; you must learn to "zag."
Life isn't linear. When I was growing up, I was sure I was going to be a major league baseball player, have four kids, and have my dad watch me play in the big leagues. Here I am. My baseball career ended at 22. I never made it to the big leagues. My dad passed away at 60. And I have two amazing kids instead of four.
Never in my wildest dreams did I think I'd be in the learning and development world. Sometimes you can't control the detours. When life zigs, you've got to learn to zag. Adaptability is everything, especially in this fast-paced world.
The next time you run into a speed bump, don't play victim. Own up to it. Make the best out of it and keep going.
The Brutal Truth: Confidence comes from reps, not readiness.
Confidence doesn't come from sitting back and waiting. If you want to be great at something, you've got to get out there and do it.
Starting "absolutely awful" is the prerequisite for becoming "fantastic."
When my book first came out, I got on a podcast tour. I was scared to death. I jumped on my first podcast with my now friend Andy Storch of Talent Development Hot Seat, and I was absolutely awful. Embarrassing. But I asked Andy for advice and told myself I wanted to get good at this. The only way was to get back in the game. Since then, I've been on 150 podcasts. I still have a ways to go, but I know without a doubt that by this time next year I will be better than I am now.
You don't get good at something by waiting around. You get good by starting. Confidence comes from reps.
The Brutal Truth: Saying yes to everything is a fast track to burnout.
I've always wanted to be a people pleaser. But saying yes to everything leads to burnout, and you'll end up turning down things you should have said yes to because you don't have time.
The "VIP Curse": High producers get more work thrown at them until they stop being successful.
I see this all the time. I call it the VIP curse. You have two project managers. One never hits goals. One crushes it. So you throw more projects on the high performer. If this person doesn't set boundaries, they'll burn out or leave.
If you're that person, you have to learn to say no. Sit down with your boss and say, "Look at what I've got on my plate. Can we reprioritize?" Any decent boss will say, "Great point. Let's work this out." They don't want to lose you either.
The Brutal Truth: Poor leaders protect their comfort zones; great leaders protect their people.
I learned this from Gary Ridge, who has a great book called Any Dumbass Can Do It. He said poor leaders protect their comfort zone by avoiding tough conversations.
Feedback is a service that allows your team to learn and grow.
About a year ago, we had a sales rep who was underperforming. At first I thought, "This person will figure it out. I don't like having difficult conversations." Then I finally said, "I have to have this conversation." I sat down with them. They took it very well, thanked me, and immediately turned it around. If I had protected my comfort zone, they may not even be here now.
Leaders, you're doing your team members a disservice if you're avoiding those tough conversations. They deserve to learn and grow. A lot of times that can't happen without feedback.
The Brutal Truth: Your identity is who you are (integrity, humility), not what you do.
At 22 years old, my baseball career ended and I thought, "What am I going to do? I've only identified as a baseball player. Are any of my skills even transferable?" I was depressed.
But I didn’t know that I had what I’d later understand was my "Athletic Education": Transferring skills from one identity (like baseball) to another (CEO).
I started as a receptionist and worked my way up to become CEO of Learnit. I realized what I learned playing baseball (my athletic education) was all transferable. I wish I didn't go through that year or two where I was afraid to see people, thinking they'd ask, "You're not playing baseball anymore. What's wrong with you?"
It doesn't matter if I'm a baseball player or CEO. My identity is someone with high integrity who's humble and wants to be kind. Don't let a job loss or title define yourself-worth. Your real identity is who you are as a person.
The Brutal Truth: You will regret the chances you didn't take more than the ones you missed.
I'm 17 years old, sitting at the dining room table with my parents and Bill Serena, a famous scout from the Atlanta Braves. In front of me is a contract for $125,000 to play in the minor leagues. My parents said, "Damon, this is your decision. We'll support you."
I had a full ride to Pepperdine. Deep down, I wanted to take the contract, but I was scared and unsure of myself. I passed it over. I went to Pepperdine, then Arizona State. I had a great career, but you know what? I've never had a minor league at bat. I never got a hit in the minor leagues. I've gotten over it, but it's something I really regret.
If there's a situation (a person you want to ask out, a job, an idea), take that leap. Don't let fear or "what if" stop you from trying. Please learn from me on that.
The Brutal Truth: Travel and living abroad are leadership accelerators for problem-solving and empathy.
If you have an opportunity, especially while you're young, live overseas. I interviewed Erin Lewellen, CEO of Tilting Futures, about the incredible value of living and working abroad can bring to a person’s life. What you learn from living abroad is that it gets you out of your comfort zone. You become a better problem solver because you don't know the language or customs. It's an amazing way to get a different perspective.
When you're looking to hire leaders, find people who have explored and lived in different countries. They're more adaptable and can look at things from different perspectives.
I just shared 12 lessons I know now that I wish I knew earlier in my life.
Here's my challenge: Think about just one of them and apply it this week as 2025 winds down. Start the new year now. Whether it's saving money, having that difficult conversation you've put off, or going for that opportunity you've been hesitating on. Do it. Just do that one thing today.
Leadership development isn't about perfection. It's about progress. It's about being willing to fail, adapt, and grow. These brutal truths shaped my journey, and I hope they help you avoid some of the pitfalls I stumbled into along the way.
Find me on LinkedIn and share with me one thing you learned that you wish you knew when you were younger. I'd love to hear your story and connect with you.
Until next time everybody, stay curious, keep learning, and have a great holiday season.
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