Exploring Goal Clarity and Personal Connections

Full transcript and all links: dialectic.fm/henrik-karlsson

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.

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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

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