Greg here! This past weekend, I was asked to speak at the “Win Where It Matters” retreat. I was drawn to speak and attend both days of the event because I wanted to learn from other speakers about a topic that feels essential in midlife:

What does “winning where it matters” mean? What truly matters to us? And how can we define and design our lives around a personal metric of success—one that is uniquely ours, not borrowed from someone else’s playbook or societal expectations?

I took a ton of notes and condensed them down into 26 takeaways that I wanted to share with you.

  1. The Work Starts When You Leave the Room.
  2. Stop Talking, Start Doing.
  3. Challenges Are Constant; How We Handle Them Gets Better. Everything is Hard.
  4. Empowerment over Entitlement.
  5. Action > Outcome.
  6. Don’t Quit Your Job to Follow Your Passion. That Could Be One of the Most Irresponsible Things You Can Do.
  7. Chasing Authenticity Where Authenticity Does Not Exist is Exhausting.
  8. Maintain Momentum and Flexibility.
  9. Complexity Fails, Simplicity Scales.
  10. You May Not Be the CEO of Your Company, but You Are the CEO of Your Own Life.
  11. We’re All Consistent. The Key is Making Consistently Good Choices Rather Than Consistently Poor Choices.
  12. Embrace Curiosity and Be Open to Change.
  13. Fulfillment Over Applause.
  14. Minimum Effective Dose.
  15. Focus on Standards, Not Just Goals.
  16. We Attract and Repel Exactly What We Deserve.
  17. Situations and Circumstances Can Either Defeat Us or Define Us.
  18. Mediocrity Happens by Default. Maximization Happens by Design.
  19. Master the Middle. Success is Not Found in the Extremes.
  20. It depends.  
  21. Don’t break the promises you make to yourself, don’t break the promises you make to others, and don’t make too many promises period.
  22. It’s not what you’re doing, it’s what you’re not doing.
  23. Don’t major in the minors.
  24. Motivation is fleeting, discipline is the muscle you need to train most. 
  25. You’ll never graduate from any of this so you may as well learn how to enjoy the process. There’s no day where you get to stop and things stay just as you want them
  26. Reserve the right to change your mind.