Each year, I write my annual review and I share it publicly. I think it’s useful to look back and answer a series of prompts to ensure I’m living in alignment with my core values. I encourage you to do the same. Here is my 2023 year-end review and a look ahead to 2024.

**Note: Now is the perfect time to pre-order our new book, The Score That Matters. I think it has the opportunity to change your life if you’ll let it :)

Looking back at 2023

What were your most significant accomplishments this year?

Living in alignment with my core values:

  • Thoughtful: My mantra for being “thoughtful” is silence and reflection. How I do this: early mornings alone before my family wakes up, long walks with my dog, and journaling (Homework For Life).
  • Thankful: My mantra for “thankful” is to leave people, places, and things better than I found them. This means showing up for each meeting with a person with the intention to leave them better. It means picking up the trash at the park. It means saying thank you to people all the time.
  • Curious: My mantra for curious is to “stretch my zone of competency.” This means I need to regularly talk with and listen to people who are wiser than me. Interested > Interesting. I’ve been fortunate to have many deep, long-form, 1:1 conversations throughout the year. My skills as an interviewer have improved through all of the reps. Listening is a critical skill to continue to develop to live out my value of curiosity.
  • Consistent: My mantra for consistency is “Show Up.” I published 53 episodes of The Learning Leader Show. I shipped 52 “Mindful Monday” emails. Never missed.
  • Learning Leader achievements:
    • Ran three Learning Leader Circles.
    • Hosted our fourth annual Learning Leader Growth Summit in Columbus, OH, in May. (You can WATCH the highlights HERE)
      • Had James Clear as a surprise live podcast guest to end the event on a high. (I’m not sure if I’ll ever be able to top that)
    • Built the next Circle, which will launch in 2024.
    • I finished the manuscript for my next book (which comes out on March 26, 2024).
  • Keynotes
    • Did 26 paid keynote speeches in 14 states.
    • Did 9 virtual keynotes for leadership teams from all over the world (The UK, Netherlands, and multiple states in the U.S.).
      • Built new long-term working relationships (speaking engagements, consulting, and advising) with some world-leading companies.
        • My business has evolved to be a media + advising/consulting company. I regularly create useful content (podcasts, essays, books) and the result of that work is requests to work with leaders from businesses all over the world. This is not what I intended to do when I launched The Learning Leader Show, but I’m grateful that it’s worked out this way.
        • As part of this, I’ve built a great team of coaches (Sherri Coale, Brook Cupps, Geron Stokes, and Eli Leiker) to help me deliver excellent value to my clients.
  • Insight Global achievements:
    • Completed our second IG Learning Leader Circle, creating a positive impact on 24 leaders and all they lead.
    • Had 1:1 calls with every IG teammate who asked.
    • Taught multiple electives as part of Insight Global University.
    • Worked with teammates from the IG Leadership Academy to help create new curriculum for leaders.
    • Did 4 keynote speeches for every new employee who joined the company in the summer/fall months.
    • Participated in the IG The Pursuit of Excellence book club.



  • In February, I had a keynote in Las Vegas. Immediately after I finished on stage, we drove to Zion National Park and hiked for 3 days…

  • In November, we went to Sedona, AZ to hike for three days. Being outside, seeing the beautiful mountains from the bottom… And then the top is as good as it gets.

Taylor Swift

  • Had an epic Dad/Daughter trip to Detroit to watch Taylor Swift put on a show…


  • Spent a week in beautiful Lake Tahoe walking 18 holes a day with my brother. So grateful.

Where did you fall short, and why?

  • For the second year in a row, I didn’t write many thank you notes. I failed because I didn’t make it a priority. Need to do better.
  • I said yes too much. After reviewing my calendar, I noticed that I had too many meetings and not enough time to reflect, think, and create. I need to find a better balance to do the necessary work to build my business AND block 3-4 hour blocks of time that are focused on deep work.
  • I did not land any of my dream guests 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. I have updated my list of dream guests (see below) and will keep at it.

What did you learn from this year that you’ll apply to next year?

  • The best way to build my business is with my existing clients. I’ve learned that if I do good work and help my clients become more effective, they will ask for more. I’m going to lean more into this in 2024 and beyond. This also eliminates any need for “selling” what I do. My focus is on helping my clients be better leaders. When I do that, good things seem to happen for my business.
    • There are different ways to “scale,” and I like being a high-value, high-dollar, boutique provider.
  • There is huge potential to grow my leadership circles. The demand (measured in applications) has increased in 2023. We could have 5 or 6 high caliber circles if I had the team in place to facilitate and run them. I am maxed out at how many I can personally run. It would be wise to hire someone to help with the entire program (organization, scheduling, teaching, facilitating, and communication with members).
    • Action step: I have identified a few facilitators to lead Circles for clients who want a deep focus on learning new skills for a year. I’ve noticed that the best facilitators are those who have been in my circles for years.
  • I didn’t create any new digital products in 2023. I intend to do more of this in 2024. I like Jack Butcher’s “Build Once, Sell Twice,” mentality for digital products.

My Top Podcasts of 2023

Looking ahead to 2024

What are the most important things you want to achieve next year?

  • Live true to my core values (thoughtful, thankful, curious, consistent). My behaviors must line up with my values.
  • Work out every day. I get one body. If it fails, nothing else matters. Take care of it.
  • Go on at least 180 walks with Miranda.
  • Create memorable moments for my teammates and clients:
    • Do such great work that at least one Insight Global teammate sends a note (every week) that my work has positively impacted their life.
    • Wow audiences from the stage. 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.”
    • 10X their return. Set such ambitious standards for my work output that all clients feel they get at least a 10X return on what they invested in me.
    • Do things that don’t scale. Respond to emails from listeners/readers of my work.
    • 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.
  • Ship excellent work:
    • Publish my third book, The Score That Matters, on March 26, 2024.
    • Publish at least 52 “Mindful Monday” emails.
    • Publish at least 58 episodes of The Learning Leader Show.
      • Record at least 6 solo, AMA (Ask Me Anything), episodes. (If you have a question, send me an email: Ryan (at) LearningLeader dot com
      • Record at least 4 episodes in person. The face-to-face experience 10x’s the relationship built with the guest.
    • 2024 Podcast dream-guest list: Doris Kearns Goodwin, Marques Brownlee, Sara Blakely, Dave Matthews, Satya Nadella, Dave Chappelle, Rick Rubin, Peyton Manning, Aaron Sorkin, Mike Rowe, Brad Stevens, Novak Djokovic, Claire Cormier Thielke.

Overall, 2023 was a step in the right direction. My business grew and I met some amazing people on the road speaking. I’ve built relationships with some clients that I intend to work with for life. I am going to focus this year on surrounding myself with others who can help my business grow so that I’m spending the majority of my time with the people I want, doing the things I want to do, and having 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.

This quote from Lawrence Pearsall Jacks (that I shared in chapter 6 of The Pursuit of Excellence) is a north star for me:

“A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing, and leaves others to determine whether he is working or playing. To himself, he always appears to be doing both.”