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My Favorite Posts of 2021

4 min

Hello! And Happy Holidays.

First off, let me say: I am so, so grateful that you are here, reading what I write. To say that I appreciate it is a gross understatement. Thank you.

I don’t often rest well. It takes me at least a solid week before I actually start to “unwind.”

But rest is critical - resting both the body and our critical faculties. Every religion in the world has an extended period of “rest” on the calendar… a time to disconnect from the world and rejuvenate.

To that end, I’ll be taking the end of the year off from Better Questions. No worries, though - we’ll be back to our regularly scheduled programming in January (and paid subscribers to BQ will still get their issue of the Weekly Roundup on Thursday!)

2021 was a big year for Better Questions - We went from 2,000 to over 8,000 subscribers, I moved the blog from Wordpress to Ghost, launched the paid version, and much more.

I wanted to take a moment and look back on some of my favorite pieces from the year - and, if I’m being honest, to pat myself on the back a bit.

It’s hard to write a blog post a week for an entire year on top of everything else I do. We (and by we, I mean “I”) don’t celebrate our wins all that often - we’re too busy criticizing our shortcomings. Consider this week an opportunity for me to correct that a bit - and for you to catch up on some cool posts you might have missed.

So, without any further ado - my favorite posts from 2021.

The Elephants

How can you build something if you don’t know what it’s supposed to be?

One piece at a time.

As close to a manifesto as Better Questions gets. For me, the creative process is a discipline - a religious practice, meant to stave off the dark. There’s a reason I show up here every week - and it certainly isn’t to make money.

It’s because I believe, as deeply as I believe in anything, in the transformative power of reaching out and trying to communicate with another person. Hopefully, even if only one or two times a year, I manage to do that with these letters.

You Must Lift

When the time comes,

you will need to bear aloft an enormous weight,

an unimaginable burden:

You know it's possible, and no one believes you.

It probably doesn’t come as any surprise, but every letter I write for Better Questions is auto-biographical.

In You Must Lift, I seek to remind myself that struggle - and the growth that ensues - is how we get the strength needed to change the world.

No lifting, no growth.

The Personal Values Series

My wife and I had a conversation this year about personal values. She said she wasn’t 100% clear on what mine really were.

At first, I was a bit insulted - but it makes sense. I’m ambivalent about a LOT of things that people around me believe quite deeply. I often feel I simply don’t have enough information to believe strongly one way or the other. This can lead to the impression that I don’t believe much of anything at all.

But that isn’t true. I do have some deeply held beliefs - on the value of inquiry, on our responsibility to act rationally, on our responsibilities to one another.

This series was an attempt to get those down in writing. They are, as follows:

The Ethics of Raising Cobras

Freedom of Speech

Freedom From Fear

Freedom From Want

Freedom Of Conscience

Somedays, It’s Just Your Turn

Written on a week where I just could not get my planned piece done.

what do you do, on the days when it's your turn?

What do you do when the world is against you, and your brain isn't working, and you can't bring yourself to do the things you know you need to do, the things that would be good for you, the things that would help?

When you simply can't bear the thought of rolling that boulder uphill one more god-damn time?

You say what I said:

"Somedays, it's just your turn...

But it'll be better tomorrow."

The Quarterly Review Series

Consistently, the single most valuable thing I do is check in with myself every Monday to ask: “what the heck just happened?”

Figuring out what went well, what didn’t, and whether I need to change creates a powerful feedback loop that keeps me on track…and believe me, I have a tendency to go off track.

Quite a bit of theory on the why of it all, plus the brass-tacks breakdown of how I actually get it done.

Proximal and Distal Causes



The Review

The Personal DanBan Series

A deep dive on the only productivity system I’ve stuck with consistently. Highly modular and hackable, requires nearly ZERO upfront investment, and super-fast to set up.

Experiment and see how it goes.

The Iron Laws

The System

Without Anxiety of Imperfection

Our enemies are internal.

My critical voice is particularly strong, and sometimes it feels like it’s going to run me into the ground. I have a sense that you sometimes feel the same.

Naming the internal critic for what it is, embracing it, accepting it, and ultimately moving past it…that, I think, is going to be the great work of my next 5-10 years.

No Time

A reminder to myself to think carefully about the raw materials I put into my brain.

Try to pick the forms of culture that:

And for the no-less-practical, but more philosophically-inclined among you:

Choose well how you spend your time.

We don’t have much left.

Before I go, let me say just one more time:

Thank you so much for being here.

I don't know if I'd be writing this if you weren't reading it. It means the world to me.

Happy Holidays,


Cool Stuff To Read


An old one from the incredibe Slate Star Codex. This changed the way I think about the "social safety net," and is unlike any argument you've likely heard about the issue.

Not technical, not about policy, but about philosophy, and what each of us owes to the society that surrounds us.


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