8: Steph Ango - Tools for Amplifying Our Light

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Feb 4, 2025

In this enlightening conversation, Steph Ango, CEO of Obsidian, shares his multifaceted journey as a designer and entrepreneur. He emphasizes how creative constraints can enhance innovation and the delicate balance between freedom and discipline in the creative process. Steph discusses the importance of thoughtful tool design, privacy in a tech-dominated world, and the significance of personal agency. He also explores the transformative power of genuine passion and curiosity, urging listeners to cultivate resilience and engage deeply with their creative pursuits.

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ADVICE

Embrace Constraints

Constraints can empower creativity by providing a focused canvas.
Embrace constraints in design and life to foster innovation.

ANECDOTE

Winamp Skin Constraints

Early Winamp skin designs required working within strict pixel limitations.
This constraint fostered creative problem-solving in a limited space.

ADVICE

Self-Imposed Constraints

Self-imposed constraints, like short-form writing, can be empowering.
They create a recognizable style and make creation easier.

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1984

None

George Orwell

Published in 1949, '1984' is a cautionary tale by George Orwell that explores the dangers of totalitarianism. The novel is set in a dystopian future where the world is divided into three super-states, with the protagonist Winston Smith living in Oceania, ruled by the mysterious and omnipotent leader Big Brother. Winston works at the Ministry of Truth, where he rewrites historical records to conform to the Party's ever-changing narrative. He begins an illicit love affair with Julia and starts to rebel against the Party, but they are eventually caught and subjected to brutal torture and indoctrination. The novel highlights themes of government surveillance, manipulation of language and history, and the suppression of individual freedom and independent thought.

Erewhon

or, Over the Range

George Orwell

Samuel Butler's "Erewhon" is a satirical utopian novel exploring themes of social critique and technological advancement. Published in 1872, it presents a fictional society with unique customs and laws, offering a commentary on Victorian England. The novel's exploration of technology and its potential consequences is particularly noteworthy, with its prescient warnings about the dangers of unchecked technological progress. Butler's work anticipates many concerns about artificial intelligence and its impact on humanity, making it a relevant read even today. The novel's enduring appeal lies in its blend of satire, social commentary, and philosophical depth.

Tomorrow, and Tomorrow, and Tomorrow

Gabrielle Zevin

Spanning thirty years, 'Tomorrow, and Tomorrow, and Tomorrow' by Gabrielle Zevin is a sweeping narrative that explores the lives of Sam and Sadie, two friends united by their love of video games. From their childhood encounters to their adulthood as successful game developers, the book delves into themes of identity, creativity, disability, and the redemptive possibilities in play. It is a coming-of-age story that examines the multifaceted nature of human relationships and the need to connect, love, and be loved. The novel is praised for its mature and nuanced portrayal of characters and its ability to engage readers even without prior knowledge of the video game industry.

Tools for Conviviality

Ivan Illich

Ivan Illich's "Tools for Conviviality" is a critical examination of industrial society's impact on human life. Illich argues that modern technologies, while offering efficiency, often lead to dependence and a loss of control. He challenges the notion of progress as solely technological advancement, emphasizing the importance of human scale and self-determination. The book explores the ways in which industrialization has shaped various aspects of life, from work and education to healthcare and transportation, highlighting the negative consequences of these systems. Illich's work serves as a call for a more human-centered approach to technology and social organization, advocating for conviviality as a guiding principle for a more just and sustainable society.

The Beginning of Infinity

Explanations That Transform the World

David Deutsch

In this groundbreaking book, David Deutsch argues that explanations have a fundamental place in the universe and that improving them is the basic regulating principle of all successful human endeavor. The book takes readers on a journey through various fields of science, history of civilization, art, moral values, and the theory of political institutions. Deutsch explains how we form new explanations and drop bad ones, and discusses the conditions under which progress, which he argues is potentially boundless, can and cannot happen. He emphasizes the importance of good explanations, which he defines as those that are 'hard to vary' and have 'reach', and argues that these explanations are central to the Enlightenment way of thinking and to all scientific and philosophical progress.

Non-Things

Byung-Chul Han

Byung-Chul Han's "Non-Things" delves into the pervasive influence of digital technologies on contemporary society. Han argues that the digital realm fosters a culture of distraction and superficiality, hindering genuine engagement and critical thinking. He explores the concept of "digital exhaustion" and the ways in which constant connectivity leads to a sense of emptiness and alienation. The book critiques the commodification of experience and the erosion of traditional forms of social interaction. Han's analysis offers a compelling critique of the digital age, prompting readers to consider the impact of technology on their lives and the broader social fabric.

Steph Ango aka Kepano (Website, X) is a designer, writer, entrepreneur,and toolmaker, best known as the CEO of Obsidian, a powerful and flexible writing and thinking tool.

Steph's education is in biology and industrial design, but he is true multi-hyphenate creative, working across mediums including software, hardware, supply chain and packaging, words, wood, furniture, ink, color schemes, open-source systems, video, podcasts, and more. Above all, he makes tools—deeply opinionated ones—designed to reduce friction for himself and others in the act of creating.

Steph joined Obsidian after initially contributing as a fan and enthusiast and impressing its co-founders, Shida Li and Erica Xu. Under his leadership, Obsidian has grown into one of the most beloved and powerful independent software tools in the world, with millions of users. As a daily user myself, I rely on Obsidian for my research and thinking for this podcast. Before Obsidian, Steph founded Lumi and Inkodye, the former of which was acquired by Narvar.

Beyond design, Steph is one of my favorite writers. His concise, sub-500-word essays have shaped my thinking on design, software, learning, agency, constraints, and creativity. While we couldn’t cover all of his ideas in this conversation, we explored many of them in what became my longest conversation to date—one that is packed with wisdom. I believe these ideas will challenge you in unexpected ways and push you to be more creative, agentic, and optimistic.

Transcript for episode 8.

Timestamps:

(1:56): Constraints and style
(11:51): Aggressively planting creative seeds but being patient for them to grow
(17:42): Stadium of past and future selves
(22:34): Asking what can be removed and making incremental progress
(28:47): Building a product and company (Obsidian) with the "constraint" of ideology and principles
(38:52): Using Obsidian makes Steph better at building Obsidian
(44:09): What makes for good design and seeing the world as something designed (by nature or man)
(53:11): What makes a good tool?
(56:20): Thinking tools and Obsidian
(1:04:32): "In good hands" and caring more than anyone else
(1:21:38): Engaging all five senses
(1:24:46): Creating cohesion or your own cinematic universe
(1:30:43): How to time travel
(1:33:08): Designing for digital durability or permanence & "File over app"
(1:56:46): Investment and "selfishness" in extending your light
(2:05:54): Choosing problems to work on
(2:09:10): "Nibble and your appetite will grow"
(2:12:31): Compounding
(2:19:55): "Caloric energy is precious"
(2:26:21): "Earth is becoming sentient"
(2:39:31): Busy being born and sharing along the way
(2:42:11): Love and freedom

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