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52 Things I Wish I Knew In My 20s

Jun 30, 2025

At the age of 52, I have been an entrepreneur for over 25 years, sold over $150 million worth of services and have failed many more times than I succeeded. My failures did not define me but instead redirected me to having a “rich life.” Here are 52 lessons I learned over the past 52 years:
 

  1. Success = Achievement + Fulfillment
  2. Be nice to everybody
  3. Want what you want
  4. Keep a journal
  5. Time, Money, and Health are life’s tools – they don’t mean everything unless you don’t have one of them
  6. Relationships and Purpose are life’s riches – you will fully invest in them once you have life’s tools out of survival mode
  7. How you do one thing is how you do all things
  8. Be healthy and fit – physically, mentally, and spiritually
  9. Don’t compare your timeline with others
  10. All things in life can be systemized, and these systems will give you the freedom you desire
  11. Your future should always be greater than your past
  12. Embrace your story – past, present, and future
  13. Focus on making revenue recurring
  14. Confidence = Certainty – Uncertainty + Faith
  15. Be grateful for all that you have
  16. Don’t fear loss – everything you have is borrowed
  17. Who you marry will be your most important decision
  18. Prioritize 8+ hours of sleep
  19. Money is exchanged for value
  20. Don’t lend money to anyone
  21. Plan your day the evening before
  22. Know the difference between good and bad debt
  23. An asset grows in value AND produces cash flow
  24. Don’t trade your time for money - get your money working for you
  25. Give to givers. Avoid takers and matchers.
  26. Don’t eat at night past dinner
  27. Learn to negotiate
  28. Money is an amplifier – not bad or good
  29. Do hard things first
  30. You become the average of the five people you spend the most time with
  31. Ideas are worthless without action
  32. Your greatest gift sits right next to your greatest trauma
  33. Recognize in public, criticize in private
  34. Find the joy in helping others grow
  35. Your network creates your net worth
  36. Avoid perfectionism before taking action
  37. Your reputation will make you magnetic – show up on time, do what you say you’re going to do, finish what you start, and say please / thank you / I’m sorry
  38. Learn how to delight others with positive surprises
  39. Define your core values – personal and business
  40. Create a three-year vision – personal and business
  41. Execute goals 90 days at a time
  42. Have a Sunday meeting to plan your week
  43. Limit your daily to-do list to three to five things of high value
  44. Focus on what you can change and accept what you can’t
  45. Your daily actions need to reflect your values and vision
  46. Everyone wants to FEEL: appreciated, important, and included
  47. Have rigorous honesty – with yourself and others
  48. The best way to continue learning is to teach
  49. Stock the cupboards during harvest season
  50. Leverage is the small actions that produce large results
  51. All business expenses should connect to gaining or retaining clients
  52. Each new level of success requires a positive change in habits

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