35 Reflections on Life and Business

Recently I celebrated my 42nd birthday. I took some time to reflect on life and business. Here are some of the top things I have learned:

1. Relationships with depth, trust, and intimacy are the primary way to achieve lasting contentment in life.

2. Have a clearly defined personal mission. The reasons behind your actions have a profound impact on how others experience you—having a clear why serves as a north star during trying times and inspires others to join in the journey with you.

3. Who you are is more important than what you do. A wise mentor has emphasized this to me over time. Ultimately your character is far more important than your resume or accomplishments. The Bible says it best: “What does it profit a man to gain the whole world but lose his soul?”

4. Don’t be too proud to ask for forgiveness. Forgiveness doesn’t change the past, but it does enlarge the future

5. Generosity is the antidote for greed. Be generous with everyone. Give to people and situations where you don’t stand to gain anything in return.

6. Affirmation and encouragement are among the most encouraging and life-giving things we can offer to others. The best part of all is that they don’t cost us anything. Be generous with your words of praise.

7. The best parts of life are a result of compounding. At 42, I can trace out how my favorite things have resulted from repeatedly prioritizing and working on the same essential things.

8. Be transparent and honest. It is tempting to try to manage how others perceive us, but it always backfires in the end. When there is integrity between the perception of others and our reality is much less stressful.

9. Ask others for feedback and be willing to change. We cannot grow unless we understand how others experience us. Instead of being defensive when we receive hard feedback, assume it is accurate and look for applications.

10. Think backward when making major life decisions. How will you feel about this decision when you are 80 or on your deathbed? It is incredible how much this helps me at forks in the road points in life.

11. Cultivate thankfulness in your heart. Find ways to deliberately identify and give thanks for the things that bring joy and happiness to your life. Thankfulness is the vaccine against bitterness as we age.

12. Investigating what the Bible says about Jesus was life-changing for me.

13. Fulfillment comes from a life that is devoted to something larger than self. Reject the idea that fulfillment comes from chasing all your internal desires.

14. Reading biographies is one of the easiest ways to learn from the experiences of others. It also makes people from different eras more relatable and accessible. The great people that came before us dealt with all the same challenges and desires that we experience.

15. Having discernment about when to forge ahead or strategically quit is a superpower. My tendency to persist has been my biggest strength and biggest weakness at different points in my life.

16. View mistakes as tuition. The lost resources (time, money, etc.) offer the potential to learn a valuable lesson for the future.

17. Develop a growth mindset. Intentionally challenge yourself to grow in areas that are uncomfortable or where you lack natural talent. The process of getting better through effort and determination is empowering.

18. The culture you immerse in will shape the person that you become. A steak gradually takes on the flavor of a marinade it sits in, and similarly, we become a reflection of the cultures we are a part of every day. Choose the friends, spouse, and jobs that promote a healthy culture.

19. Learn through doing. The internet has made it easier than ever to gain knowledge about any subject you desire, but we learn best through doing. Don’t settle for acquiring knowledge. Find ways to start applying that knowledge in your life immediately.

20. The world is more complex than ever before. Our natural response is to simplify, but complicated things aren’t simple or black and white. The answer to complexity isn’t simplicity; it’s focus. Reject simplistic narratives and embrace nuance.

21. Compete with yourself instead of others. Instead of fixating on being “the best,” spend time focusing on reaching “your best.”

22. Achieving excellence comes through iterative improvement. The paradox of excellence is that it can only be achieved by practicing at a less than excellent level for a long time.

23. Life is full of trade-offs and opportunity costs. Saying “yes” to one thing means saying “no” to countless other things simultaneously. Learn to say “no” frequently so you have the margin to say “yes” to the right things.

24. Help others to believe in themselves. Everyone needs an encourager that helps them to see their full potential.

25. Make asymmetric bets. Find places where you can invest time and resources with a fixed downside, but the upside could be 10x or 100x. Some examples are mentoring, investing, and going on a first date.

26. When planning a business, identify how you can create moats (sustainable competitive advantages). Building a company is hard work and will take years of your life. Build something defensible from the beginning so that you don’t have to watch the market erode what you have built.

27. Don’t settle when hiring. Be slow to hire and prioritize character, competency, curiosity, and hunger.

28. Entitlement is like emotional cancer. Pat Riley once described it as “the disease of me,” and in my experience, it is the number one risk to successful teams. Focus on treating other people better than they deserve instead of focusing on how you should be treated.

29.  Constantly cast vision to those that you are leading. “If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

30. The best entrepreneurs I know are like scientists. They are constantly forming theories and designing experiments to test those theories and learn more about the world.

31. The most successful individuals have plenty of failures in their careers. What makes them successful is that they keep taking swings. Be more afraid of never hitting a home run than of striking out.

32. If you start a business, bootstrap for as long as you can before raising money. One of the most freeing aspects of Simple Modern is that we don’t answer to outside investors. We are a stronger, more generous company as a result.

33. The very best way to learn about business is to join a high-growth startup. There is no better place to grow your skill set, advance your career, and learn how to build a company.

34. Focus on process over results. I have found that results and the process are often less correlated than I would expect. I cannot control outcomes, but I can dictate how I approach the process. Over time, this is a winning strategy.

35. Life requires a bias to action. There will be countless times when it is unclear what is the right next step; making an imperfect choice and iterating is almost always better than doing nothing.

Which of these resonate with you?


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