Dickie's Digest - Life Interviews, Optionality, Rabbit Holes, Consistency, and First Principles

Jan 18, 2021

Hey there, happy Sunday.

This week was the closest I’ve come to skipping an edition of the Digest. I put it off all day, instead spending time “reinventing” my personal organization system for what feels like the hundredth time. But alas, here we are! And there are some absolute gems in this week’s Digest, so be sure to scroll all the way through.

Two things from me this week:

Sign-ups for the Ship 30 for 30 February cohort are still going. I’m hooking Digest readers up with $100 off. If you’re interested, reply to this email and I’ll send you the code. Over 161 members are signed up for February, ready to kickstart their writing habit.
My most popular Atomic Essays this week were on just-in-time learning and asking the Hamming questions.

That’s it from me! In this week’s Digest:

Have an epic week!

Dickie

⁉️ How to Interview Your Parents

This document is a blueprint for conducting a life interview, aimed at children interviewing their parents. I think this is such a cool concept. There are so many things I want to know about my parents, their upbringing, how they spent their 20s, all of that. So when I saw this list of questions, I bookmarked it immediately, knowing I would want to revisit it in the future.

The questions are grouped into four buckets:

Childhood
Adulthood, Personal Identity
The Present
Aging

The questions inside cover everything you would ever want to know about your parents. And doing it in a recorded, interview-style format means you’ll have them forever. This is high on my list to complete in 2021.

Read more: How to interview your parents

📖 Richard Meadows and Optionality

This week I listened to an episode of Modern Wisdom with Richard Meadows, author of the book Optionality: How to Survive and Thrive in an Unknowable World, and the blog deepdish.org.

To say he and I see the world similarly would be a remarkable understatement. His core thesis is optimizing for optionality when you are young. This means keeping expenses low, attachments loose, and opportunities open. And in his book, he presents a system and way of thinking for doing optionality optimization in a concise, actionable format.

His blog is also an incredible rabbit hole to learn more about minimalism, travel, financial independence, health and fitness, and the power of writing. Here were a few of my favorite posts of his:

There’s plenty more good stuff on there if you’re looking for a nice afternoon rabbit hole.

Read more: Optionality and Deepdish.org

🔥 Last week’s most popular link

waitwho.is

🎧This Week in Podcasts

If you love the Digest and its weekly podcast recommendations, consider checking out the Digest Podcast Compendium. It’s a curation of my favorite podcast episodes ever recorded, tagged, and summarized with three key takeaways. Supporters get three new podcasts and summaries every week plus an invitation to a private Slack group to chat about the best episodes.

Andrew Wilkinson on the Creator Lab Podcast
Andrew Wilkinson talks, I listen. Such a simple, first-principles approach to thinking, investing, and building. He’s scaling the Berkshire Hathaway of the internet, and I surely wouldn’t bet against him.
Khe Hy on the Compound Writing Podcast
Khe Hy is the reason I am on edition 55 of Dickie’s Digest. In January of 2020, I attended a RadReads happy hour in NYC. And I asked Khe for advice on starting a newsletter. He said one thing very simply: commit to doing it for 52 weeks. Everyone either quits by then or figures it out. And here we are! He shares such good advice in this conversation, I highly recommend it.
Richard Meadows on the Modern Wisdom Podcast
This podcast was like hopping into the world’s deepest echo chamber. I agreed with literally every word in this conversation, which probably means I need to diversify my content diet. Either way, this one was a gem and sent me down the rabbit hole of Richard Meadows’ blog.