Two of the things I’ve recommended most in conversation (and on Substack!) in recent years were written by Henrik: Looking for Alice and Everything that turned out well in my life followed the same design process.
One is about finding your wife; the other about designing the rest of your life. Its hard to say exactly what stands out so much about them and Henrik’s writing, but I suppose the through line is that he takes such obvious, over-explained and over-advice’d topics and somehow finds a way to come at them in a new and intuitive way.
Perhaps his most powerful idea, and the approach he lives, is that combining deep introspection with experimental, iterative action produces a life that is unpredictable and yet wonderfully fit to who we are.
As we discuss, the name of Henrik’s blog, Escaping Flatland, is based on the Edwin Abbott story of a similar name in which a two-dimensional square who comes into contact with a three-dimensional sphere. Henrik often writes about people who are spheres: those who expand you and your world beyond imagining.
Henrik is surely a sphere for me, and for many of his readers and web of strangers (friends) he’s cultivated by way of writing.
I hope you enjoy the conversation as much as I did.
Dialectic Ep. 19: Henrik Karlsson - Cultivating a Life that Fits
Dialectic Episode 19: Henrik Karlsson - Cultivating a Life that Fits - is available on Spotify, Apple Podcasts, YouTube, and all podcast platforms.
Henrik Karlsson (Substack, X) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently recommended: on designing your life and finding your wife (or husband).
Henrik's always written, but lived a winding path across software programming, music, poetry, biology, an art gallery, and other odd jobs. A few years ago, Henrik and Johanna picked up their life in Sweden to move to a small island farm in Denmark so they could homeschool their daughters. He now writes on Substack full-time and lives an unusual dual-life: one is remote and intimate; the other is connected and wide.
My favorite theme of his writing is self-cultivation: introspection and action, designing a life that fits you by experimenting, how to think and how to learn, embracing being wrong and seeing past your blindspots, and living in concert with past and future selves.
I also love his writing on relationships: how to find your life partner, why writing helps others see the inside of your head, how to use the internet as a serendipity machine for finding your people, teaching and parenting, and what its like to be around exceptional people who make your world bigger.
He also writes about education, self-organizing systems, AI, exceptional childhoods, and more. But I find the topic rarely matters—all of his writing expands me. What a gift. I hope you enjoy the conversation as much as I did. May we all embrace the burden of freedom—freedom to iteratively unfold into a life we never could have imagined. If you enjoy the episode, please consider supporting Henrik's writing, as he is fully reader-supported.
This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.
Timestamps
2:36: Self-Cultivation, Introspection, and Larry Gagosian
8:46: Writing to Think
16:05: Using Strong Opinions as an Opportunity to Learn (and Willingness to Look Stupid)
21:53: "Not That" vs. "Maybe this?": Creativity and Formulating a Positive Possible Future
25:12: Self-Criticism and Kindness to Your Past Self and Ideas
28:44: Eclectic Interests (Poetry, Programming, Music) and a Winding Path to Becoming a Writer Pulling on the Threads of "Dead Ends"
33:10: Introspection, Agency and Being Sentenced to Freedom
38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments
49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us
1:04:16: The Role of Ambitious Goals in the Context of Unfolding
1:10:06: Hampton
1:11:41: Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible
1:26:53: Asking Questions that Push People Past their Cache
1:31:12: Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet
1:48:55: Ruthless Prioritization and Making Time to Get Better
1:57:05: Initial Spark and Connecting with People
2:05:58: Collaborating with Henrik's Wife Johanna
2:09:46: Living a Barbell Life Inside and Outside of the Computer and Henrik's Scale of Ambition
2:16:48: Sacrifice
2:18:57: Pseudonymity and Playing with Identities
2:20:57: Self-Organizing Systems
2:22:51: Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold
2:33:13: Writers Who Help Us See Ourselves
2:35:13: Writing and Thinking in Swedish vs. English
2:37:44: Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves – And Modeling That For Others
Links & References
6 lessons I learned working at an art gallery - Henrik Karlsson
Everything that turned out well in my life followed the same design process - Henrik Karlsson
On limitations that hide in your blindspot - Henrik Karlsson
Into the abyss | Death Row Documentary - Werner Herzog (0:00-5:29)
#003 - Henrik Karlsson on Creating Your Milieu, Writing, & Apprenticeships - Audience of One
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