“Matter” is my theme for this year. As in: What matters?
So far, it has been fun to ask this question in my personal life. What are the things I really need? Who are the people I really want to be around? I’m decluttering and prioritizing the people I care about.
When it comes to my work, however, asking this question hasn’t been fun at all. It’s throwing me for a massive loop. All writers eventually hit this wall. In my case, I look back at seven years and some 2,000 pieces, and when I ask, “Which ones did I really care to write?” the answer is “Shockingly few.”
When you’ve written every day for so long, there’s always another idea, always another fluff piece you could write. Fortunately or not, I’m so bored of fluff pieces. I’d rather not repeat myself for 50 years. So, how can my problem be to your benefit?
Well, in my investigation of “Which writing matters?” I couldn’t help but dig up the articles that mattered most to me over the years. The following nine are beacons of light I keep coming back to again and again. I hope you too will find their timeless wisdom worth revisiting.
1. The Cook and the Chef by Wait But Why
One of the hardest things in the world is to be an original thinker. This article can’t teach you to be one all the time, but it will show you what original thinking looks like and how you can think for yourself more than you let others do the thinking for you. It’s a guide to seeing the world with your eyes instead of everyone else’s, and that’s the only way to live an authentic life.
Tim’s post is long, packed with funny stories, great metaphors, and useful tools for getting what you want. By giving you a simple two-word framework through which you can look at the world, however, it also makes reading so many other articles unnecessary.
The words “cook” and “chef” seem kind of like synonyms. And in the real world, they’re often used interchangeably. But in this post, when I say chef, I don’t mean any ordinary chef. I mean the trailblazing chef — the kind of chef who invents recipes. And for our purposes, everyone else who enters a kitchen — all those who follow recipes — is a cook.
2. How To Be Successful by Sam Altman
Having interacted with thousands of founders at Y Combinator, Sam shares 13 patterns he observed in those who aren’t just rich on paper, but also rich humans — happy, calm, focused, and looking out for those around them.
Sam’s post helps me zoom out, take the long-term view, and not get bogged down in details while remembering there’s more to life than money and status. That said, here’s my favorite quote about winning big from the piece:
It’s useful to focus on adding another zero to whatever you define as your success metric — money, status, impact on the world, or whatever. I am willing to take as much time as needed between projects to find my next thing. But I always want it to be a project that, if successful, will make the rest of my career look like a footnote.
3. How To Get Rich Without Getting Lucky by Naval Ravikant
Countless scandals throughout history have proven: No matter how much money is demonized in public discourse, secretly, everyone wants money. The church wants money to the point of gambling with believers’ donations. Governments want money. Presidents want money. You and I want money.
Naval’s tweet storm that went around the world looks at everyone’s desire without judgment, and, next to a guide on how to get it, provides an important reminder: Money is just a tool — and if you use it well without getting addicted to it, it is a much better pursuit than fame or status.
Seek wealth, not money or status. Wealth is having assets that earn while you sleep. Money is how we transfer time and wealth. Status is your place in the social hierarchy.
4. 11 Reasons Not to Become Famous by Tim Ferriss
We’ve all imagined the glitz and glam while scrolling through the ‘gram. Oh, the perks of being an influencer! But what about — uh-oh — the jerks? The stalkers? The kidnappers?
Tim’s article is a crass reminder that attention-overwhelm is just the tip of the iceberg of the many downsides of fame. It’s a piece I think of often, because the images he conjures are as vivid as they are scary. There’s no shame in staying small, even when you’re trying to make it big.
Once in Central Asia, I had a driver show up at my hotel to take me to the airport, but…he used my real name, and I’d given the car service a fake name. To buy time, I asked him to wait while I made a few phone calls. About 10 minutes later, the real driver showed up to take me to the airport, using the designated pseudonym. The first fraudulent driver took off, and to this day, I have no idea how he knew where I was staying or when I was leaving. But it bears repeating: there are professionals who do this, and they will be very good at what they do.
5. The Million Dollar Question by Sebastian Marshall
Do you want to be you, or do you want to be who everyone wants you to be? This is the central question of Sebastian’s piece, which invokes a mental image you’ll remember for years to come: Him sitting on a bench at a rural Japanese train station, sipping canned iced coffee and observing idyllic suburban life.
This article is poetic and insightful. It reveals a fundamental truth and asks us to make an important, somewhat binary decision: Do I want to live my dreams, or do I want to feel understood? A timeless masterpiece.
The million dollar question… why don’t people take the large opportunities in front of them? Why don’t they allow their dreams to become realities?
Because it means you won’t be understood. And we need to be understood, fundamentally, it’s so important to us.
6. The Most Important Skill Nobody Taught You by Zat Rana
“We now live in a world where we’re connected to everything except ourselves,” Zat says in this piece about Blaise Pascal, the limits of technology, and the value of being by ourselves so we may know ourselves. It is only the pinnacle of his big body of enlightening work, but since it’s concerned with our most fundamental experience — existence — I return to it the most.
Why be alone when you never have to? Well, the answer is that never being alone is not the same thing as never feeling alone. Worse yet, the less comfortable you are with solitude, the more likely it is that you won’t know yourself. And then, you’ll spend even more time avoiding it to focus elsewhere. In the process, you’ll become addicted to the same technologies that were meant to set you free.
7. Managing Oneself by Peter Drucker
A surprising lesson I’ve learned in my career is that although it matters what you do for a living, how you do it matters just as much, if not more, when it comes to your happiness.
Working in a process-driven, meeting-laden management role simply does not work for the self-driven, highly creative internet savant. Figure out who you are, then assemble your work around yourself. This is a never-ending journey, and Peter Drucker has the map. The HBR article is a good start, but read the book too. The audio is only a 45-minute listen, but one you’ll likely repeat.
Most people think they know what they are good at. They are usually wrong. More often, people know what they are not good at — and even then more people are wrong than right. And yet, a person can perform only from strength. One cannot build performance on weaknesses, let alone on something one cannot do at all.
8. Cognitive Bias Cheat Sheet by Buster Benson
The number one thing that gets in our way is ourselves. Cognitive biases are mental loopholes that shortchange our thinking. The only way to avoid them is to constantly stay aware so you can recognize them in real-time.
Buster’s piece is a phenomenally helpful guide to developing said awareness, especially because it groups a big set of biases into four big problems they’re trying to solve. Remember those problems, and you’ll think a lot more clearly.
Every cognitive bias is there for a reason — primarily to save our brains time or energy. If you look at them by the problem they’re trying to solve, it becomes a lot easier to understand why they exist, how they’re useful, and the trade-offs (and resulting mental errors) that they introduce.
9. “Hell Yeah!” or “No” by Derek Sivers
Life is short. If we don’t want to waste a lot of the little time we have, we must constantly take action for what we truly believe in. Derek’s piece is a short but prudent reminder, one he has repeated in various forms for over ten years now. Even if he just did it for himself, I’m grateful I too can come back to it from time to time.
When deciding whether to do something, if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” — then say “no.”
When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”
What these pieces have in common is that they offer some analogy or story that makes them easy to remember. Not everyone will connect with them, but if you do, you’ll do so in a lasting way — because beyond an idea, the author has given you a powerful memory that’ll allow you to revisit the concept again and again.
“What matters?” is a hard, never-ending question. These articles won’t provide easy answers, but they’ll make facing it a little easier to endure. If you find yourself browsing them for the second time, think of me and smile — maybe that way, even I will find a shade of evergreen on the universe’s grand shelf.