33 Takeaways

From entrepreneurship and engineering to health and wellness, I’ve never learned so much in a single year from so many incredible people.

When I say “learned”, I don’t mean “heard” or “observed”—I mean truly, deeply, and measureably experienced these lessons first-hand.

What follows are my 33 takeaways of the year. Each includes bracketed initials crediting the friend, colleague, client, or family member who best embodies the lesson as I understand it today.

1. If whatever you’re doing now isn’t the greatest thing you’ve ever done, you’re headed in the wrong direction. Maintain nonnegotiable standards to filter high volumes of opportunity. [MW]
2. From girlfriends to customers, people deserve clarity. Even if they don’t like what you have to say, they’ll appreciate your transparency in the long run. [TZ]
3. All tools have inbuilt limitations. If you recognize these limitations, most tools become twice as valuable. [TK]
4. True “experts” know not what they’ve learned, or how much, but what they haven’t. It’s not immediately clear to me why anyone is particularly qualified for anything. [EG]
5. To help others solve problems, don’t tell the answer—facilitate their thinking to help them arrive at your solution independently. They’ll adopt it more eagerly, completley, and creatively. [MW]
6. If you’re smart, nothing is a big deal. If you haven’t solved a problem, it’s usually because you haven’t tried and are lying to yourself. [TR]
7. Success is built on failure. If you haven’t failed along the way, it’s an indication you probably aren’t approaching success. [SS]
8. You’re only done learning when you choose to be. If there was nothing useful left to learn, you’d rule the planet. And you don’t. [AM]
9. Genius, unlike stupidity, is bound by ego. Transcend the self to transcend the problem. [RV]
10. Distributing more risk is often safer than consolidating less risk. The only thing you have to fear is risk itself. [SvS]
11. Semantics aren’t semantics. Words matter, and don’t deserve to be an afterthought. [LP]
12. When making strategic decisions under pressure, consider three key criteria: sustainability, scalability, and stability. Also consider what kinds of capital it can cultivate: economic, social, intellectual, individual, political, human, risk, spiritual, brand, or legal. [JW]
13. Authenticity is liberation. Don’t fall in love with anything that doesn’t involve you at your truest and your best. [TZ]
14. Constraints can be good. They force you to expose what you value. [RS]
15. “But” is the wrong word 99% of the time. Often, no conjunction is needed. [OA]
16. You haven’t “empowered” someone until they’re able to empower others. Accessibility, freedom, motivation and capacity are hallmarks of empowerment. [BE]
17. Hierarchy works because it’s natural. Horizontalism works because everyone tries harder. [GK]
18. How you think about how you think, matters. Do you think of yourself as realistic? Or are you actually pessimistic or optimistic? [BO]
19. Failure “per se” is not a good thing, as many people believe. That doesn’t mean it’s not valuable. And it’s OK to be OK with failure. [KR]
20. “Lead from the back, and let others believe they are in the front.” It doesn’t matter that you’re the leader, only that you’re good at what you do. [BE]
21. When used properly, money is not a motivation, but a measure of motivation. And untainted motivation is usually self-perpetuating. [DE]
22. Organization hinges on three things: control flow, intent, and function. Everything else is superfluous. [MW]
23. People prioritize intent. It’s what they pay for, fall in love for, and go to war over most of the time. [RK]
24. Flip a coin. Just before it lands, you’ll know what you want. [AK]
25. Most opportunities are just accidents captured and capitalized upon. They’re neither the most nor least significant path to a win. [YF]
26. Truth is a state of mind. And everyone has their own opinion. [MK]
27. “Human systems move in the direction of the questions they ask.” Asking what question to ask is often underrated. [DC]
28. Teaching and selling are just two sides of the same coin. Teaching is making someone care enough to understand; selling is teaching someone to love something the way you do. [EG]
29. “A poem is never finished as long as you’re still breathing.” There’s always impulse for improvement or change. [JB]
30. “Reality divided by expectations equals happiness.” Likewise, you are under no obligation to give people what they expect. [SW]
31. Assumptions are everywhere. Identify them pathologically. [RA]
32. There’s no such thing as “luck”. Either you make your own luck, or the people around you make it for you. [SS]
33. The difference between confidence and arrogance is empathy. Leaders know this and claim responsibility for it. [CB]

To all those who have made me a better person, I thank you. In a very real way, I wouldn’t be the learner I am today if not for each of you. To everyone else, I encourage you to broaden my horizons: please, leave your comments in the margins to question, support, or extend these nuggets.

After all, there’s nothing like a good conversation to uncork the New Year. ■