I turned 40 over the weekend. Oof.

For as long as I can remember, I’ve collected quotes and ideas. I used to jot them in the margins of high-school binders and fill my college notebooks with them. Every few months I skim those fragments and drop the best into the Notes app on my phone. It’s become a bit of a ritual, and I enjoy the entire process.

I’m usually drawn to the pragmatic stuff—principles I can actually use. So this year, as I hit the 40-year mark, I thought I would select a few of my favorites, the ones I keep returning to the most in my work life in case you find them helpful to.

1. Reality has a surprising amount of detail

This is summed up with the old quote:

“We did not do it because it would be easy. We did it because we thought it would be easy.”

There is usually a good reason why things are how they are. Respect the complexity so you can meet it head-on. And the next time you complain about how booking a flight sucks, remember this.

2. Activity will always take the place of a goal

Time spent ≠ Progress. A lot of modern knowledge work is coordinating activities and people.

Make a plan. Send it for feedback. Follow said plan. And so on. But it’s easy to miss the most critical thing—what is the actual goal here, and did we make progress against it?

This is a reminder to push back.

3. Intensity is the strategy

The most successful strategy for long-term success is intensity over a sustained period of time. Nothing else is even close. Picking the right strategy is important, but intensity to move it forward will always drive more outcomes. I find a lot of freedom in this because it places the emphasis on something you can always do – work hard at it.

4. Everyone has something to teach you

It’s easy to poke holes in things and feel smart. Negativity is a constant drumbeat of the media.

Self-select out of it. People are good and the world is a positive place. Wisdom and earned experience can be found everywhere. Just ask and listen.

5. Be a big target for luck

If I could recommend a single thing to actively “do,” it’s this: increase your surface area for luck. Try things, meet people, read books, ask questions, experiment with new tools, be an active participant, seek out expertise. Take an intelligently applied work ethic directed at continual improvement and be deeply committed to learning and teaching.

6. Meaningful = Hard

If something worthwhile appears easy, it means I got lucky. Most things that are meaningful are hard for a reason. The toil is required to access the next level of whatever game you’re playing. Don’t be fooled by lucky breaks disguised as perceived “earned” wins. (It doesn't end well)

7. Slow down and respect everything around you as someone else’s life work

My Opa and my Dad taught me this. Every detail—from the building lobby you walk through to the sandbags over sewer grates—was created out of nothing by someone. Pay attention to the details and appreciate the people behind them and the world takes on a whole new perspective.

8. Be more interested than interesting

I’ve had to learn this again and again. There’s a lot of value in asking questions to understand, not impress. Be curious, not judgmental. Everyone has a story, and they’ll share it—if you prompt it.

9. Accelerate what you can control

Only focus on the things I can directly influence. There is no point in sitting around moping about the state of the world and unfair bounces. Lean into the things I can directly influence, as this always results in the highest throughput. Let the rest fall into place.

Reminder: The future is owned by optimists.

10. Don’t aim to be successful, aim to be useful

This mindset shift is subtle but powerful. People gravitate to those who just want to help move things forward. Chances are you know who the most high-agency people are in your life. Be someone who gets things done.

Success is a byproduct of action.

11. If you let it, the urgent will always overwhelm the important

The best way I have found to fight this urge is to maintain strong habits and focus. But the most progress is made when the important takes priority over whatever the day throws at you. Most of modern work tools like email and Teams are designed to be optimized for the urgent—take back control of your day and the productivity will follow.

12. Invert: Aim to minimize negative outcomes

Charlie Munger’s idea to “invert” is always with me when I make strategic decisions. Avoiding failure is often easier than defining exact steps to a successful outcome.

Ask: What are the worst outcomes here? Then plan to avoid them.

13. Choose things with a good base rate of success

The average of how others perform is often the best predictor of my results.

I want to be in situations where the base rate is attractive—where I don’t need to hit a home run to win. This idea of picking a good base rate from Brent Beshore has stuck with me. Why choose games with bad odds?

14. Win and help win

The world isn’t zero-sum. Helping others win is just as rewarding as winning yourself.  Helping win is more than just being a cheerleader. It’s playing an active role in supporting, connecting, and building up the people around you in their careers.

15. Pick opportunities with asymmetric outcomes

There are endless opportunities. Look for things where the upside is 3–4x the downside. Rule #1 of investing time or money: don’t get wiped out. Rule #2: look for asymmetric upside. And if you don't think its there, avoid forcing it to make it look that way. The best opportunities don't make you squint.

16. Life is messy

People, business, relationships—me included. Expect chaos. Meet it with grace. Setbacks are part of the game, not the exception. Don’t fear the messiness—navigate it. The truth is, if things feel smooth, its either temporary or you are missing something.

17. Never stop exploring

“Your archive paints your future, so build a rich repository.” I love that line. Build an deep archive of ideas, notes, experiences. Revisit and remix what you’ve learned. Life is full of unexpected connections just waiting to be made, so build a big internal library.

18. In business, maximization is the minimization of joy

I don’t thrive in environments where the game is endless optimization. That’s probably a “me” thing, but I have found that individuals and teams really come alive when they apply creativity to how they approach or tackle problems first. Optimization is part of the game—but not the whole game.

19. Don’t bet on stasis

The world is always changing. Bet on that. If something “isn’t done that way,” it doesn’t mean it won’t be. Embrace change. Be skeptical of blue-chip certainty and Excel models with perfect curves.

‍