Life advice upon turning 25, built from experiences shared with you

I should start with a disclaimer and acknowledge that age 25 is still considered to be in the nascent stages of maturity. I don’t disagree with that. But a lot of the times, we say the words we need to hear. So if you can, treat this less as a diatribe and more as a reminder to myself of how I intend to live the future days (and quarter centuries, now that I can say that).

I hope this list will grow over time. To that end, if you are a close friend or family member of mine reading this, please continue to share with me, and I will do the same. The list below, of course, is a reflection of your presence in my life. Thank you.

Another disclaimer before I start: I have never been afraid or shy of platitudes. 

1) "Work hard, be kind, and good things will happen to you."
This was stolen from Conan O'Brien's speech on his last episode of The Tonight Show. In moments of overwhelm and when I feel like I can rationalize myself onto either side of a decision, I revert to Conan’s simplification of…everything. At the end of the day, if you can work hard and be kind, good things will happen to you. 
Thank you Amanda, for bringing me to Team Conan at an early age. I think I was 12 when I first saw Triumph The Insult Comic Dog. My conscience has never been innocent since. 

2) "The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day. That is real freedom." 
I appreciate the entirety of David Foster Wallace’s This Is Water speech and I return to it periodically to remind myself that the hardest moments to maintain a sense of selflessness are in the mundane - the trips to the grocery store, the boarding of an airplane, driving in traffic. 

3) Make decisions.

4) Before making a major life decision, ask myself this: What would I do if I wasn’t afraid?
It is incredible how much clearer this can make decisions. 
Thank you Emily S., for being my big sister. 

5) Learn how to say yes. Then learn how to say no. 
A lot of my time in college and my first couple of years after college were spent saying yes. It’s a fairly easy thing to do in a place like New York City, where there are no shortages of events, activities, and people. But saying no is simply another way to reserve your energy for saying yes to the things that matter most. 
Thanks Dan, for showing me the power of essentialism. But I’m still waiting for my ficus tree. 

6) Never let the amount of time it takes to accomplish something stop you from doing it. That time will pass anyway.

7) Complain less.

8) You can remove a lot of anxieties by distilling your to-do list to the one true thing that needs to be accomplished on any given day.

9) Confidence is being able to say I don’t know, but I can try to find out. 

10) Friendship is like anything else in life. The more effort you put in, the more you get out. 
Thank you Dan, for letting me make a video on your birthday that makes fun of every habitual Dan-ism. And thank you Phil, Tony, and John for making that video with me.

11) Read more.
There are so many good books and each one of them has unique ideas and worlds. In this weird way, books are the most affordable ways to have experiences.
Thank you Michael R. for teaching me how to read critically. 

12) Find your own metrics of success.

13) Find a way to have an impact on the inequities our systems have set up. 
I used to think that tackling systemic inequities and inequalities were the kinds of problems that took centuries of years and masses of people to re-correct. But adopting that kind of thinking sometimes overlooks the many ways to make smaller contributions, like volunteering a weekend, becoming a mentor, donating wisely, or becoming fully informed on an issue.
Thank you Amit and Anish, for engaging with me every week on these challenges.

14) Some of the best advice that’s ever been given to me came from people who were really good at listening, not necessarily at speaking. 
Also not a bad way to think about business relationships and identifying areas of collaboration across multiple stakeholders. Not being able to listen well means not being able to identify and name the situation. 
Thank you Erika, John C., Matt, John T., Frank, and Yu-Im for showing me what this means in our work. 

15) Take calculated risks. 
Sometimes the riskiest choice is the one that seems the most safe. When I left Google, I remember asking myself, “If I can't make jumps in my career now, then how else was I going to teach myself the excitement and joy of new adventures?" What seemed to be riskier was depriving myself of experiences because of fearful decision making, especially this early in the game. 
Thank you Todd for the healthy hunger. And thanks, Jon A. for leading by example.

16) Try not to take yourself too seriously.
Thanks Charles, for not being ashamed of having the goofiest laugh on record, from the age of 12 when we first met until now. 

17) As much as possible, try to employ a mind of realistic optimism. 
Recently I was at a show - The Together At Last Tour with Pete Holmes and Rob Bell. Early in the first act, Rob Bell described three different frames of mindset. The first was naive optimism, the mind that sees the world glass half-full while turning a blind eye to the many challenges of the world. The second mindset was one of defeated pessimism, the mind that allows cynicism to override action. The third mindset expressed a hybrid of the two - realistic optimism, the mind that acknowledges all of the bad, but chooses to stay hopeful. The example given in the show was a meeting between Desmond Tutu (who has witnessed apartheid at its worst) and the Dalai Lama (an exile of his own homeland) where upon seeing each other for the first time in years, they hugged and laughed for entire minutes at a time. Rob Bell finished this story outlining how both of these figures have seen more of the bad than we might ever, but they still choose to live with realistic optimism. 

18) Focus on doing one thing at a time. Less multitasking.
Even with the small things. Brushing your teeth. Washing the dishes. Waiting in the elevator.
Thank you Tomas, for bringing a practice of daily meditation into my life. 

19) Say I love you to friends and family more.

20) Commitment is continually willing to try harder.
Thanks B.

21) F = F
Fat = flavor. Perhaps the biggest bang for your buck cooking tip. 
Thanks Julian for bringing me into the kitchen.

22) Don’t look at a phone or desktop for the first hour of the day.

23) A lot of success is keeping calm and coming up with a plan.
Try not immediately reacting to the disaster, and see what fixes itself organically. Because disasters always happen. Additionally, the really good people are able to define next steps instead of wallowing in the resistance. 

24) Savor the Beginner’s Mindset and the road to learning new things.
The other way to read this is to emphasize the process, not the product. The happiness of pursuit, not the pursuit of happiness. 
Thank you Mom, for putting me in more extracurricular activities than necessary while growing up, for showing me how to teach myself, and for showing me how to pick my strengths and weaknesses. But for the record, I still think I could have made it to the NBA. 

25) Spend some time strengthening weaknesses. They don’t have to be as well developed as your strengths, but don’t make them liabilities. 
Growing up I loved playing point guard and using my quickness to drive into the lane for quick lay-ups. But I was only able to do this with my right hand, which effectively cut off half the space on the floor for me to work with. I never got as good at shooting lay-ups with my left hand, but I eventually built up my left-hand weakness so that it didn’t give defenders an easy way to shut me down.
Thank you Dad for the shooting drills in the driveway and the hallway.

26) The days are long, but the decades are short.
Stolen from Sam Altman, my inspiration for this post. Each night, if possible, take a couple minutes to think about all the great things that happened that day.