September 19

35 Pieces of Life Advice We Should Get, But are Never Given

People ask me what I’ve learned from talking to all these people. And this morning, I woke up somewhat jet-lagged with a flurry of thoughts.

First, as Nikki Groom taught me, everyone has a story worth telling, and anybody can teach you something. I’ve received education from bank robbers, drug dealers, psychologist and billionaires. I also got a degree from Berkeley. I would describe these thoughts as life advice we should get but are never given:

1. Figuring out what you were born to do requires trial and error. This process is not linear despite that fact that we are educated to approach life in a linear fashion. If there’s one commonality between the 700 plus people I’ve interviewed, it’s that their path wasn’t linear.

2. The only place you can go by following someone else’s map is to a destination that’s already been reached. To do what’s never been done, you have to be willing to take a detour, assume nothing is sacred, and use a compass instead of a map.

3. It’s hard to expand your horizons when your perspective is limited to one town, one country, one bubble. Some countries have traffic that makes crossing the street a near-death experience. If you spend your life in suburbia, you’ll never learn to tolerate the stress of bigger and bolder things.

4. Every choice, how you spend your time, the friends you make, and the job you take are leading you in a direction. Make sure it’s what you want.

5. On the anniversary of 9/11, I remembered the CEO of our first company. He came into our sales office that day and asked how our sales calls were going. The lack of empathy was a huge red flag. The board eventually fired him.

6. It’s one of the great paradoxes of life that you get what you want when you don’t need it. When you expect nothing, everything comes to you. When you start to get what you want, you’ll be delighted. But this kind of delight is the enemy of detachment. It causes you to cling to what you have, and forget that it can be taken away from you.

7. Learn to be committed but detached, flexible but focused, agile but relentless.

8. If you have to choose between increasing your rank or expanding your skills, choose the latter. At least this way, no matter what, you’ll have the skills. An increase in rank is temporary. Expansion of skills is permanent. Rank can be taken away from you, your skills can’t.

9. You might finish school, but your education is never done. It’s never too late to learn more, acquire new skills, and become a better version of yourself.

10. In the pursuit of anything that matters, you will be tested. You will enter periods of darkness. As Justine Musk said to me, the darker times teach you what you need to know to get where you want to go. In the darkness, you discover your capacity for light. In your setbacks, you develop the mindset that leads to comebacks.

11. Often, we lose what we have to make space for what we need. You lose a client, a girlfriend, or something else. Loss creates an opening in our lives. If we don’t fill that space with panic and anxiety, whatever replaces what we lost will be better. It just won’t ever seem that way in the moment.

12. Someone will let you down and you will let someone down. The inability to go through life without unintentionally hurting someone is the fatal flaw of our humanity. If I haven’t let you down yet, just wait. We probably haven’t known each other long enough.

13. Second impressions will reveal far more than first impressions. In second impressions, you learn who a person really is and what they’re really like. Our first impressions are often clouded by emotion. Who a person is on day 100 is going to tell you more than who they are on day 10. People don’t reveal their character with one kind deed; they reveal it with their actions over time. And one unkind deed can undo 100.

14. Don’t punish the people in your future for the actions of the people in your past. They had nothing do with it. Until you stop doing this, your future will continue to look like your past.

15. You are more than your job title, the bullet points on your resume, or relationship status. To define ourselves based on external markers and labels, is to limit ourselves and our sense of possibility.

16. Social capital works differently than other currency. You make deposits by helping people, but you never check the balance, or even measure it. That’s the difference between a connection and a transaction.

17. Influence is not fans, followers, and websites with lots of traffic. Don’t confuse metrics with influence. The most influential people in all of our lives are often unsung heroes like public school teachers and sports coaches.

18. Out of the spotlight, behind the scenes are people who manage the lives of rockstars and celebrities. Meaningful influence can’t be measured with vanity metrics. My most influential mentor had 100 followers on twitter.

19. Any life choice you make based on status is by definition impermanent. Status always fluctuates. The hottest girl in school ages. Today’s superstar might be tomorrow’s afterthought.

20. If you pursue an unconventional path, you will be misunderstood for a long time by parents, peers, and society. Decide what is more important: validation of the people who will never live with your choices or the life you want.

21. In any endeavor, faith, conviction, optimism and unwavering belief are necessary. This is especially true for extreme success. These will be tested when you deviate from a tried and true path.

22. Without solitude, silence, and reflection you’ll be drowning in the noise of other people’s opinions of what you should do with your life. One way to cultivate more is to stop reading shit like this and quit Facebook.

23. If you want to do more than meet the expectations of society’s life plan, come up with your own definition of success. This definition isn’t just a series of boxes you check. It continually evolves because of the eternal gap between who we are and who we want to be.

24. The job, the car, the stock options, the McMansion… all of them can be taken away from you. Don’t let your possessions define you or determine your self-worth.

25. Almost nothing is the catastrophe we make it out to be. I lost my sim card after buying a new one in India. When I sat down, I remembered Naval’s advice about valuing your time. I could read and write for the next two hours or go searching for a sim card that I can’t even use until 3 weeks from now.

26. All advice is context-driven. It’s based on one person’s experience. Of course, the person who sells a podcasting course is going to shout from the mountaintops that everyone should start a podcast. Same goes for all the investors who say everyone needs to be on some social platform.

27. Treat advice like ingredients. But come up with your own recipes. YOU are the blatantly obvious variable that will throw off every formula for success.

28. You can live your life based on the things that will go on you resume. Or you can live it based on what people will say in your eulogy. The second is what David Brooks calls the road to character.

29. Don’t ever forget the role that luck, privilege and class have played in your accomplishments. If you have parents who valued your education, didn’t grow up in poverty, and had people who loved you unconditionally, that’s privilege.

30. Even the most successful people are aware of the role that luck plays. David Letterman told Obama he’d been nothing but lucky.

31. Everybody has something you don’t. And you have something they don’t. One of my best friends is crushing it in his business, met his wife, and is about to have a baby. But when he came to my 41st bday at my parent’s house, he told me how lucky I was to be that close to my family.

32. Treat the time you have with the people who matter most to you as your most precious resource because it is.

33. Develop a tolerance for discomfort. Learn to navigate ambiguity, and keep moving forward in the face of uncertainty. Unless you can do this, you’ll always be at the mercy of other people.

34. If you start and build things, nobody will ever care about those things as much as you do.

35. If there is such a thing as the divine order of the universe, you can’t force that timeline. Some people succeed later in life, and hit major milestones on a different timeline. One thing that helps with accepting this is to be less skeptical about new-age bullshit. Become a spiritual skeptic (which is how I’d describe my view on the things I can’t explain). I’m open-minded about it, but still skeptical.


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