40 Lessons I’ve Learned by Age 40 (Part Two: 21-40)

Two weeks ago I celebrated my 40th birthday. In the weeks leading up to it, I reflected on my life and all that I’ve learned so far. I compiled 40 lessons I want to highlight. Below are lessons 21-40. Click here to read lessons 1-20.    

21. What you do matters more than what you say. This is true with everything, but it’s especially visible with kids. My kids see everything I do. Any inconsistency is immediately recognized. A few months back, my seven year old asked, “Dad, how come you tell us to eat healthy but I always see you eating chocolate chips.” Ooof. 

Early in a coaching partnership, I invite clients to identify their core values. These are the things they say are most important to them. I then challenge them to rank how they’re living their values. This uncovers any disconnect between what’s said and what’s done. We can say something is important, but how we spend our time reveals far more.   

22. Marry well. I was 24 when I got married. We were both still in college. I had a full-time job lined up at Lehman Brothers, but almost no money. Young and in love, my wife and I moved to the Bay Area a few months after marrying. One month later, Lehman went under and I found myself unemployed for what felt like an eternity. At first I felt hope and optimism. But as time passed and the rejections piled up, that hope and optimism gradually faded. 

One day I sat on the couch, unable to keep going. My wife came home from work and I was sitting in the exact spot as when she’d left. I’d spent the day paralyzed, wallowing in self pity. She looked me in the eyes and said, “So, is this it? Are you just going to give up?” 

I felt a flash of anger, then humiliation. But she was right. Most of the time she’s kind and compassionate. But at that moment, she was direct. I needed her tough love. My wife has been there every step of the way, supporting me through all the twists and turns. I’ve tried to do the same for her. 

23. Have kids early (if you can). Two years into our marriage, my wife invited me to dinner. It felt like more of a demand. I was an investment banker and she worked for a venture capital firm. We rarely saw each other during the week. I told her I was busy and asked if we could find another time. She said no. Over dinner, she told me she was pregnant. I was in shock. I was working 80+ hour weeks and could barely take care of myself. The thought of becoming a dad seemed overwhelming. The words of a Kenny Chesney song flashed through my mind: Hell, I’m just a kid myself. How am I gonna raise one?

Thankfully, it takes 9 months to make a baby. By the time our daughter was born, I was ready. She recently turned 13. We have four kids now. They mean the world to me. Each one opened a new chamber in my heart and made me better. Being a dad is one of the best things that could have happened to me. Too often we only hear about the pains and hassles of being a parent. But the joy of raising children far outweighs the challenges. I’m grateful we had kids early. 

24. Prepare the child for the road, not the road for the child. As a parent, my natural inclination is to make things easier for my children. But we all benefit by learning to do hard things, especially kids. I’ve learned that my energy is far better spent preparing them for future challenges they’ll face, not making things easier. (Note: I highly recommend reading The Coddling of the American Mind. Once you see it, you can’t unsee it.) 

25. Money will never solve your real problems. Money is a powerful tool. And it can solve problems. But it can only solve your money problems. It can’t solve your relationship problems. It can’t solve your self-esteem problems. It can’t solve your happiness problems. In fact, more money may actually make all those problems harder to solve. 

26. Collect advice, but don’t take it. Tom Peterson is one of my favorite professors and he often told us to collect advice but not take it. Few people know you well enough to cater advice to your unique circumstances. But as we all know, that doesn’t stop most from trying. I’m as guilty of this as anyone. 🙂

All advice is autobiographical. When someone tells you what you should do, they’re looking at the situation from their own life experiences. Listen to their advice. Get their perspective. Then do what’s best for you. 

27. Serve, even when it’s inconvenient. One Sunday I took our two oldest to church while my wife stayed home with our newborn daughter. After the first hour, one of the leaders pulled me into a room. He asked if I would serve as a counselor to our bishop, a responsibility that would require a substantial commitment of time and energy. 

With three young children and a busy job, I thought of several reasons why I should say no. However, I felt strongly that accepting the invitation to serve was the right thing to do. My wife felt slightly overwhelmed by the thought but was 100% supportive. Sundays were no longer a day to sleep in. I had church meetings that started at 6:30 AM and I didn’t get home until after lunch. Every Sunday morning, my wife got the kids ready and took them to church on her own.

Six months later I joined DoorDash. The job was far more demanding than my prior one and I now had a long commute to San Francisco. Once again, I questioned whether we’d be able to make it all work. I ended up serving in that church assignment for 3.5 years. The timing may have been inconvenient, but our lives were blessed in countless ways during that period. Serving helped me stay centered on the things that matter most. 

28. The fear never fully goes away. Whenever I’ve started a new job or project, I’m faced with an element of fear. Do I know enough? Am I good enough? Who am I to do this? As I take action, the fear subsides, but never fully goes away. While I’ve found this frustrating at times, I’ve come to embrace the fact that this will likely always be the case. I’ve also found that a little fear is good. It requires you to fully show up and give your best effort. Learning to take action in the face of fear is a requirement for doing anything of meaning. 

29. Create a gratitude practice. One day I came home from work frustrated. I could only think about the bad things in my life. I couldn’t shake it. I was invited to do a 30 day gratitude challenge. Each day I would write a post about one thing I was grateful for. It was life changing. When the thirty days ended, I altered my approach. I created a spreadsheet and now write down one thing I’m grateful for and why. 

I started seven years ago. Today is day 2,447. This practice takes about 30 seconds and helps me start my day from a place of abundance. 

30. Live within your means. I took a pay cut to join DoorDash. I took a pay cut to join Neighbor. I walked away from a steady salary to launch my coaching business. All of these proved to be excellent long-term decisions, but they wouldn’t have been possible if my lifestyle demanded I remain at my prior income. Living below our means was not easy. My family lived off a single income in a city with a very high cost of living. We rented a small home. We seldomly went out to eat. We made a lot of sacrifices. 

Over the years I’ve spoken to many who say they want to join a startup or take some career risk. But it requires a financial sacrifice they can’t afford to make. Their lifestyle demands they maintain their current income. There are many blessings of living below your means. Increased career options is an underappreciated one. 

31. Establish a daily practice. Over the years I’ve built a daily practice that helps me show up strong and consistent. This daily practice now comprises five core activities. I’ve found that if I do all five activities, I’m almost guaranteed to have a productive and fulfilling day. When I look back on a particularly challenging day, 9 times out of 10 it’s because I didn’t do these core activities. Completing my daily practice isn’t always convenient, but it’s essential. 

32. Show up. Talent is overrated. Over the years I’ve worked with insanely talented people who accomplished very little. They didn’t show up consistently. Things got hard and they moved onto something else. Woody Allen is quoted as saying, “80 percent of success in life is just showing up.” 

Show up. That’s it. Show up today. Show up tomorrow. Show up every day. The rest will take care of itself. 

33. Avoid toxic people. There are people who want to tear you down. There are people who are miserable and want to bring you down with them. It’s been said that you’re the average of the five people you spend the most time with. If one of those people is a net negative in your life, either severely limit or completely eliminate your interactions with them. This isn’t running away from people who need you. This is avoiding people who want to see the world burn. 

34. Write your goals down every day. Dr. Gail Matthews found that people who wrote their goals were 42% more likely to achieve them. I’ve been writing my goals for several years now. Every morning, I pull out my legal pad and jot them down. 

Writing down my goals forces me to clarify what I want to achieve. Writing my goals keeps them at the forefront of my mind. It’s difficult to achieve a goal you can’t remember. The more you consciously think about your goals, the more you’ll automatically create plans to achieve them. On both a conscious and unconscious level, you’ll strategize, evaluate how much progress you’ve made, and break down barriers getting in your way. 

35. Efficiency is overrated. I’ve found that many of my best ideas come when I am bored. And I can’t get bored if I’m hyper-efficient. I invite you to carve out time to think. Create some slack in your life. Let your mind wander. Follow your curiosity. What do you think about when you aren’t forced to think about anything? Get bored. A bit of inefficiency is a good thing. 

36. Go on a walk. When I’m frustrated or stressed, I go on a walk. When I need sunshine or a boost of energy, I go on a walk. When I have a problem I can’t solve, I go on a walk. Walking improves my mood. The monotony of putting one foot in front of the other produces clarity of thought. Walking boosts my creativity. I love walks. 

37. Small, consistent effort can lead to massive improvement. I’ve seen this in all aspects of my life, but I’ll share a triathlon example. My brother Jordan and I did our first triathlon in 2011. We only trained for a few weeks. It was a lot of fun, but our times weren’t competitive. We finished in the bottom 25%. The following year we did the same race. I trained more this time but only saw a slight improvement. We’ve done 10+ triathlons since, all of varying distances.

Four years ago we decided to train year-round. We increased our training load gradually. Despite these changes, my improvement was insignificant. I only saw gradual gains. But earlier this year I saw a step-function improvement. My times on the swim, bike, and run all got significantly faster. My brother and I went from below average triathletes to qualifying for the national championships. A week after doing that, I finished 2nd overall in a triathlon that fielded 500+ athletes, something I never thought was possible.

There’s often a major lag between your efforts and your results. You put in the work, but your growth feels immaterial at first. You don’t see the progress you’re looking for. But you don’t give up. You trust the process. You keep going. Then one day you look back at the person you were years ago and can’t believe how far you’ve progressed. The results will come. We need to be patient and let time work its magic. 

38. Things can always get worse. There are several times in my life where I had several setbacks in a short window. I remember thinking, things can’t get any worse. Often, they got worse. 

I’m all for optimism. But, to quote Jim Collins, “You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.” We all need hope, but hope is not a strategy. 

39. There is no finish line. You’re never going to feel like you’ve made it. We tell ourselves that once we buy a home, get that promotion, or reach a certain financial goal then we’ll feel like we made it. But it’s not true. We shift the goalposts. I’ve seen this in my clients. I’ve seen this in myself. Once we realize we’ll never feel like we’ve made it, we can start asking ourselves real questions around what motivates and drives us. Then we can make true progress. 

40. Turning 40 is much better than turning 30. At least it was for me. Turning 30 was a low point in my life. I was in grad school living off savings. I had a full-time job lined up but felt like I was waiting for my life to begin. I was insecure and felt like I hadn’t accomplished anything. 

10 years later, I still have a long way to go. I get defensive too quickly. I place too much emphasis on accomplishments. I have a lot to work on, but I’ve gotten more comfortable in my own skin. I’ve better discovered how I can leverage my talents to help others. I spend less energy on things that don’t matter. I’m learning to find joy in the day to day. 

Thank you for reading 40 Lessons I’ve Learned by Age 40. If one of these resonated, I’d love to hear from you. Click here to read lessons 1-20