I turn 40 in a few days. This feels incredibly weird because in my mind I’m still 25 or something. But the gray hairs I see in the mirror tell a different story. 😂

Over the past weeks, I’ve been reflecting on my life and all that I’ve learned. There are 40 lessons I want to highlight. Below are the first 20. Click here to read lessons 21-40

1) Take charge of the stories you tell yourself. Too many people let self-defeating stories thwart their growth. For years I told myself I was not creative, that I wasn’t a writer, and that I couldn’t run. For years I believed those stories. Finally, I decided it was time to tell new stories. I then started acting in a way that made my new stories a reality. I became a creative. I became a writer. I became a runner. My old stories gave me excuses for being mediocre. Don’t be a victim. Take charge of your story.  

2) You don’t have to be unhappy just because others are. Scholar Deirdre McCloskey says, “For reasons I have never understood, people like to hear that the world is going to hell.” Yes, there is evil in the world. Yes, bad things will happen to us and those we love. No, you don’t have to be miserable because of it. In the words of Russell M. Nelson, “The joy we feel has little to do with the circumstances of our lives and everything to do with the focus of our lives.” You have the power to choose what you focus on.  

3) Relationships are everything. Over Thanksgiving, my family threw a surprise birthday party where they got me 40 gifts. But it was more of a roast than anything else. My kids teased me for my idiosyncrasies. My siblings shared stories of my most embarrassing moments. My wife poked fun at me. We all laughed hard. I felt a lot of love. These relationships mean the world to me. 

4) Play the right game. Several years ago I stumbled on this quote from Kwame Anthony Appiah: “In life, the challenge is not so much to figure out how best to play the game; the challenge is to figure out what game you’re playing.” You’ve been given a set of gifts and strengths that no one else has. You’re far better off identifying games that play to your strengths. How can you stack the deck in your favor?

5) Do you actually need more information? I often pose this question to my clients. Better information certainly leads to better decisions and actions, but often we let a lack of information be an excuse for postponing action. When in doubt, assume that balance is found with more action. In the words of Derek Sivers, “If more information was the answer, then we’d all be billionaires with perfect abs.”

6) Read a lot. In 2014, I made the commitment to read 30 books a year. I’ve done that every year since. In the words of General Jim Mattis, “If you haven’t read hundreds of books, you are functionally illiterate, and you will be incompetent, because your personal experiences alone aren’t broad enough to sustain you.” To meet the challenges in front of us, we need additional perspectives. Our firsthand experiences may be limited, but through reading we can learn through the experiences of others. 

7) Say no to say yes. Shortly after Steve Jobs returned to Apple in 1997, he met with Jony Ive. Apple had 40 products on the market. “Jony, how many things have you said no to?” Jobs asked. 

Ive was confused. “You have to understand,” Jobs said, “There are measures of focus, and one of them is how often you say no. What focus means is saying no to something that you—with every bone in your body—think is a phenomenal idea, and you wake up thinking about it, but you say no to it because you’re focusing on something else.” I’ve learned that we must say no to good things so we can say yes to the best things. 

8) Make a list of the things you should worry about. In 1958, F. Scott Fitzgerald sent a letter to his daughter. In it, the author of The Great Gatsby outlined a handful of things we should worry about (courage, cleanliness, efficiency) then shared a long list of things we should not worry about (the past, the future, failure, others getting ahead of us, etc.). 

I’m a natural worrier and in moments of stress I’ve learned to hit pause and write down my worries. On paper, most of them seem silly. Fitzgerald’s letter is a needed reminder that the list of things we should worry about is very short. 

9) Set a clear vision for yourself. Five years ago, I created a doc called My Life in 5 Years. I wrote down the job I wanted to have, goals I wanted to reach, attributes I wanted to cultivate, milestones I wanted to hit, key relationships I wanted to invest in, etc. That doc provided clarity on the person I wanted to become. Much of my vision for myself has come true. Some of it has not. Parts of my vision look silly in hindsight. But there’s immense power in having a clear vision for yourself. Yes, it will likely change, but take the time to create a roadmap for your life. Set ambitious goals. Find a north star. Pivot as needed. 

10) Ignorance is a superpower. In an interview with the BBC, Welles was asked where he got the confidence as a first-time director to make Citizen Kane, a film so radically different from contemporary cinema. His response: “Ignorance. Ignorance. Sheer ignorance. You know, there’s no confidence to equal it. It’s only when you know something about a profession, I think, that you’re timid, or careful…”

I’ve witnessed many young leaders use their lack of experience to their advantage. They push the boundaries. They have courage to take risks. They break convention. They succeed at things people said would never work. They ignored the naysayers. In short, ignorance was their superpower. 

11) Pause before placing judgment. Throughout my career, countless things have happened (getting layered, new manager, team reorg, etc.) that on the surface seemed negative. In the moment, I’d get frustrated and let it derail me. Most of these situations, though difficult at the time, turned out to be just what I needed. 

Endlessly debating whether an event is good or bad is a waste of time and energy. Let things play out. Pause before placing judgment. I strive to live by the motto: Come what may and love it. We can’t always control what happens to us, but we can control our mindset. 

12) The safe path is the risky path. Many of my career decisions were viewed as risky. I pivoted from Finance to HR. I left a comfortable job at LinkedIn to join DoorDash. I left a well-funded startup to become a full-time coach. Yes, these decisions had short-term risk, but playing it safe and not developing new skills would have been far riskier. Short-term safe = long-term risky. Short-term risky = long-term safe. 

13) Optimize for learning and impact. While on the subject of risky vs. safe, I have always tried to optimize for learning and impact. When I joined DoorDash there was a reasonable chance that within a year the company would fail or I’d get fired. But I was confident that if that happened I would be better off because I would have learned a ton and had a meaningful impact on the business. Optimizing for learning and impact may not make the most financial sense in the short-term, but it always pays off in the long-term. 

14) Bet on yourself. My most career defining moments came when I made decisions that many viewed as foolish. I took action that made sense to me but didn’t make sense to others. No one knows you better than you. Bet on yourself. You may take some losses, but in the end you’ll win. 

15) Focus on the inputs. In the things that matter most, there will be a 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 must be patient. Don’t give up. Trust the process. Keep going. Then one day you look back at the person you were years ago and can’t believe how far you’ve come.

When you focus on the right inputs, and do so consistently, the results will eventually follow. Or as Bill Walsh taught, the score will take care of itself.

16) Decide where you’ll intentionally underperform. There’s a popular saying we hear all the time: “How you do anything is how you do everything.” It sounds catchy, but it’s a load of garbage. You can’t give everything your full energy. You’ll go crazy trying to do so. To do great work, you need to find areas you’ll intentionally underperform in. You need to proactively decide what you’re going to let slide. If everything is important, nothing is important. 

17) Focus on the gain, not the gap. Top performers are keen at identifying the gap from where they are today and where they want to be. Herculean effort gets poured into closing that gap. But often that gap can feel so distant it becomes paralyzing. We lose the motivation to move forward.

When I see clients beat themselves up on this, I challenge them to do the opposite: focus on the gain. A simple question gets them there: “Go back to the person you were 12 months ago. What would that person think of the person you are today? What progress have you made?” They’re always surprised by how far they’ve come. We then spend time celebrating those wins and highlighting personal growth. That creates energy which is fuel for pushing forward. 

18) Celebrate your wins. Too often we hit a milestone and immediately jump to what’s next. I regularly ask my clients to stop and celebrate their wins and successes. When I became a full-time coach, I did the same for myself. For the first few months, every time a new client signed I would celebrate with the kids. These were mostly small celebrations. Sometimes it was ice cream. Sometimes it was a bag of chips. Sometimes we’d go out to dinner. Celebrating with them was fun and it motivated me to keep pushing. 

19) Do hard things. Our brain naturally looks for ways to avoid discomfort. But as Michael Easter says, “Fewer problems don’t lead to more satisfaction, they lead us to lower our threshold for what is considered a problem.” We combat this by doing hard things. If life isn’t throwing hard things at you, you need to actively seek discomfort. This is the way. 

20) Find and utilize your gifts. I think about this passage a lot. “When I was growing up, my next-door neighbor Mr. Lewin shared a powerful bit of wisdom with me. I’ve kept it in mind for more than fifty years. On Judgment Day, Mr. Lewin said, God will not ask, “Why were you not Moses?” He will ask, “Why were you not Sam Lewin?” The goal in life is not to attain some imaginary ideal; it is to find and fully use our own gifts.”

Thank you for reading. I’ll share lessons 21-40 in a follow-up piece.