Each year, I write an annual review and share it publicly. I think it’s useful to look back to ensure I’m in alignment with my core values and doing cool things with people I love. I encourage you to do the same. Here is my 2024 year-end review and a look ahead to 2025.
2024 Professional Review
Our Learning Leader Team of Coaches officially launched. Brook Cupps, Geron Stokes, Hall-of-Famer Sherri Coale, and Eli Leiker have joined me to amp up our leadership development business. This was particularly a big move for Brook, Geron, and Eli as they left their classrooms (all were high school teachers) and joined me full-time (in addition to their jobs as basketball and football coaches). We’ve had a big impact on our clients, and we’re pumped for a huge 2025 and beyond. I love working with them and being part of a team. Our core values are Curious (Invested Listening), Honest (Direct Feedback), and Intentional (Purposeful Action).
We built our Learning Leader Monthly Mastery Program. It’s a 12-month curriculum that has been a life changer for the leaders who’ve gone through it (and many more will in 2025 and beyond).
Brook Cupps and I published our book, The Score That Matters. It became a USA Today national bestseller. Pretty cool. We hosted an amazing book launch party with a lot of our family and friends. I had so much fun celebrating with people we love.
I delivered 26 paid keynote speeches in 12 states. Speaking on stage remains one of my favorite things to do. It’s the closest feeling I get to having an actual game day like I had when I played football. With that said, I scaled back in the fall during my daughters’ volleyball/soccer seasons so that I could be present for them.
I led two Learning Leader Circles (paid Mastermind groups). The caliber of people in our groups is amazing. Our new circle for 2025 is loaded with phenomenal leaders. And our veteran groups are a who’s who of high character, excellent people.
We hosted our annual Growth Summit in Columbus, Ohio, with 43 incredible leaders (primarily members of my Learning Leader Circles). Here’s a cool video recap of it.
I shipped 52 Mindful Monday emails. This exercise forces me to write and/or find the most useful essays/videos in the world for leaders. I’m proud of the Mindful Monday community we’ve built. I’ve written and emailed for the past 448 consecutive Mondays. If you want to start receiving these (you should), CLICK HERE.
I recorded 54 episodes of The Learning Leader Show. Apple Podcasts ranked us as high as #1 in business and #22 in all the podcasts in the world! Also, we rebranded to black and gold (shortly after we hit #1).
Top Podcasts of 2024
- Episode #562: Nikki Glaser – Life as a Comedian, The Creative Process
- Episode #564: Ariel Helwani – Conducting World-Class Interviews
- Episode #566: Jim Dethmer – Conscious Leadership
- Episode #568: Tony Robbins – Becoming More Valuable
- Episode #572: Mike Beckham – CEO of Simple Modern
- Episode #575: Brook Cupps – The Score That Matters
- Episode #576: Scott Belsky – Adding Texture to Time
- Episode #578: Scott Galloway – Adding Surplus Value
- Episode #581: Paul Rabil – The LeBron James of Lacrosse
- Episode #586: Erika Ayers Badan – Former Barstool CEO
- Episode #591: Ryan Holiday – LIVE! In Austin
- Episode #593: Kim “Killer Chick” Campbell – Responding to Adversity
- Episode #596: Arthur Brooks – The Art & Science of Happiness
- Episode #600: Keith & AJ Hawk – Setting the Standard
- Episode #602: The Learning Leader Team of Coaches
- Episode #605: Seth Godin – This is Strategy
- Episode #610: Jeff Janssen – The Commitment Continuum
2024 Personal Review
Some personal highlights of 2024:
- Hosting a Sweet 16 birthday party for one of our daughters and friends in Florida with my parents.
- Attending the Ohio State Buckeye Cruise for Cancer with my brother AJ. Great cause. Lots of fun.
- Skiing in Colorado. I had a speech in Denver and decided to extend the trip. It was our nine-year-old’s first time on skis. She spent one day at ski school and then skied with us for the rest of the trip.
- Going to Lake Tahoe with AJ for the 15th consecutive year of the American Century Celebrity Golf Tournament. Always one of the best weeks of our year.
- Having an amazing dad/daughter(s) experience watching Taylor Swift perform in Indianapolis.
- Enjoying a few Dave Matthews Band concerts with Miranda.
- Working as the in-game PA announcer for my daughter’s high school volleyball team. I took it way more seriously than I probably should have, but I loved it.
- Traveling to the Bahamas with Miranda and hanging out with our friends Rob & Cheri for a few days. We went snorkeling in a cave/grotto, jumped through THIS(!!), swam with sharks, fed iguanas, visited Exuma, went on all the waterslides at Atlantis, shared amazing meals, and more.
- Coaching our youngest daughter’s flag football team. Our girls’ toughness, resilience, and competitiveness inspired me. They played so hard and badly wanted to win.
- Renovating our kitchen to create more space for family meals and hosting loved ones.
Personal Goals Reached
- I got very clear on my values and the behaviors that make them true: Thoughtful (Be still), Thankful (Leave it better), Curious (Push competency zone), and Consistent (Show up).
- I pushed my body physically by working out every day.
- Miranda and I took over 180 walks together.
- We went on cool trips (see above) and created a lot of memory dividends with friends/family.
2024 Failures
- I didn’t write many thank you notes. I failed because I didn’t make it a priority.
- I said yes too much to things wayyyy in the future. It’s easy to say yes when it seems so far away. However, those events creep up on you. If it’s not a priority, I should say no immediately instead of not worrying about it in the moment. I need to act as if the thing I’m saying yes to will happen tomorrow. If I accept too many meetings, it gets in the way of preparing, creating (writing, podcast, video), and thinking. Those actions are critical to the current and future growth of my company.
- I only did one solo episode of The Learning Leader Show. I committed to doing six. I’ve thought about doing lots of different solo episodes but didn’t execute. I need to be better and do the thing.
- I committed to recording four episodes in person. I only did one. That one, with Ryan Holiday, was awesome. I need to do more. I have to be more diligent about planning, locking in the guests/location, and then executing.
- I did not land any of my dream guests (Doris Kearns Goodwin, Sara Blakely, Dave Matthews, Satya Nadella, Rick Rubin, Peyton Manning, Mike Rowe, Marques Brownlee, Brad Stevens, Claire Cormier Thielke) for The Learning Leader Show. I spoke with multiple companies, left voicemails, sent lots of emails, and FedEx’d letters, but have not landed one of them yet. If you know any person on that list, I would love an introduction.
- I have not earned my next book deal although I committed to doing so by the end of 2024. I’ve hired one of the best proposal consultants in the world (David Moldawer), and we’ve been working on my next book proposal for six months, but it’s still not ready. This is my fault because I keep writing and throwing it in the trash. I’m not interested in writing an average/good book. I want it to be excellent, and it isn’t yet.
2025 Goals
With clients
- Make fans feel heard. Block at least five hours a week to reply to every email from a listener/reader of my work. It is always a worthwhile investment to thank supporters and take a genuine interest in them. Do things that don’t scale.
- Create an excellent experience for all Leadership Circle members. Ensure they have tangible takeaways to make them a better spouse, parent, and leader at work.
- 10X our clients’ ROI. Set such ambitious standards for our work output that all clients feel they get at least a 10x return on what they invested in us.
- Earn standing ovations. Stir emotions in people so well that they look me in the eyes afterward and tell me, “Thank you. I needed that.”
Do more work in person
- I have scheduled a leadership retreat in January. I’ve rented a big house and invited 14 leaders I admire to be there with me. We will share great meals, hike, and learn from one another.
- I will host a Growth Summit for leadership circle members (and a few guests) in May.
- I will seek opportunities to be together with other leaders in person as much as possible.
- I will record at least four in-person podcasts.
Ship excellent work
- Finish the proposal for my next book.
- Publish 52 “Mindful Monday” emails.
- Publish at least 58 episodes of The Learning Leader Show.
- Record at least six solo Ask Me Anything (AMA) episodes.
- Record at least four episodes in person. The face-to-face experience 10x’s the relationship built with the guest.
- Update the “Things I’ve Learned” PPT and share it with Leadership Circle Members.
- 2025 podcast “people I want to talk to” list: Doris Kearns Goodwin, Sara Blakely, Dave Matthews, Satya Nadella, Brian Chesky, Kyle Brandt, Angela Duckworth, Shane Gillis, Joey Votto, Kara Lawson, Rick Rubin, Peyton Manning, Dave Chappelle, Mike Rowe, Caitlin Clark, Marques Brownlee, Brad Stevens, and Claire Cormier Thielke.
Take care of my mind and body
- Work out every day.
- Go on at least 180 walks with Miranda.
- Go on at least 365 walks total for the year.
- Minimize sugar intake.
- Read every day.
- Write every day.
- Write 52 thank-you notes.
Crazy Ideas?
- Should we create the biggest Leadership Development event of all time? I recently met Matt Middleton, the guy who started and runs Future Proof. In just three years, he created the biggest, coolest, incredibly well-run event for finance professionals. He and his backers invested millions to make the biggest/best financial services festival/conference ever. Three years into it, his business is profitable and looks like an experience unlike any other in the events space. I love his ambition and story. Does an event like this happen in the leadership space? Not that I’ve seen. Could I do this? Should I? What sacrifices would need to be made to create the greatest leadership conference/festival in the world? Is this a stupid idea?
- Launch The Learning Leader Circle for Coaches – The Learning Leader Team of Coaches (Sherri Coale, Brook Cupps, Geron Stokes, Eli Leiker) has been working hard to put together a Circle specifically for coaches. I’ve reviewed the content/curriculum, and I think it could be life-changing for the members who join. I think we could create the go-to place for coaches to have an open forum to meet, talk about struggles and wins, learn from one another, and understand the commonalities of the most effective coaches in the world. This could be massive.
- Could The Learning Leader Show become a TV show? When I met with Insight Global CEO Bert Bean, he encouraged me to think MUCH bigger about the impact I could have on leaders all over the world. He said, “Dude, I was hoping you’d come in here asking for millions of dollars to pitch a show to Netflix.” I LOVE that Bert thinks this way, and I want more people in my life that push me to think bigger. Is it realistic? I don’t know, but I’m not sure it’s helpful to be realistic all the time.
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Overall, 2024 was a great year. My business grew a lot and I met some amazing people. I’ve built relationships with clients that I intend to have in my life forever. In 2025, I am going to focus on surrounding myself with excellent people who have high standards and can help my business grow. I want to spend the majority of my time with optimistic people, doing things I want to do, and making as big of an impact as possible. Ultimately, the reward for great work is the opportunity to do more. I’m grateful for that opportunity and intend to make the most of it.
These quotes from Andrew Carnegie and Bruce Lee are 2025 North Stars for me.
“You are what you think. So just think big, believe big, act big, work big, give big, forgive big, laugh big, love big, and live big.” – Andrew Carnegie
“If you always put limits on what you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there. You must go beyond them.” – Bruce Lee
Love seeing you put in the work year over year, Ryan. Thanks for chopping the wood and inspiring your listeners!
That’s a ton of production. Congrats.