How Thinking Deeply Will Transform Your Life with Josh Kaufman

Josh Kaufman is the bestselling author of books on business, applied psychology, and practical wisdom. His first book, The Personal MBA, is a top-selling business book worldwide, with more than 1 million copies sold. His second book, The First 20 Hours, introduced a universal research-based method of learning fun and useful skills. His third book, How to Fight a Hydra, a "fairy tale for the entrepreneur's journey," debuted at #1 in Modern Philosophy on Amazon.

This week, Barrett and Josh cover a wide range of topics from thoughtful entrepreneurship to heartful parenting. They talk about the profound impact of letting go of assumptions, the trap of pursuing status, and how to live with wisdom and intention. Josh shares his experiences with strategic self-publishing, why he thinks about his books like an investment portfolio, and what it looks like to define success on your own terms. They also discuss how to evaluate priorities, why emotional clarity is necessary for breaking down barriers to creativity and action, the importance of playing the long game, and much more.

In this episode:

[00:00] - Intro
[03:04] - The chocolate quality debate
[08:03] - Developing taste and preferences
[17:01] - The art of audio and narration
[30:53] - The business of books
[41:20] - Building a book portfolio
[46:27] - Choosing new projects and the paradox of choice
[01:02:07] - Status games and trade-offs
[01:15:49] - Setting the right priorities and dealing with trade-offs
[01:27:44] - The power of questioning assumptions
[01:34:30] - Parenting insights and reflections
[01:41:24] - Building a home with intentionality
[01:47:41] - Josh’s beautiful future
[01:49:28] - Who Josh is becoming

Key Takeaways

Questioning and letting go of societal expectations can unlock profound personal and professional transformation.
Strategic thinking and mental exercises, like “counterfactual simulation”, are vital tools for rethinking and reshaping ingrained assumptions.
Writing for emotional clarity is an effective technique for achieving greater self-awareness and overcoming barriers to creativity and action.
Prioritizing family and time freedom over fleeting status symbols leads to a more meaningful and fulfilling life.
Treating creative works, like books, as long-term investments can result in sustainable success and create ongoing value.

Quotes

“There’s a fundamental shift in perspective that comes from treating a book like a product. Yes, it is a means of self-expression. Yes, it is a way to get your name, experiences, reputation, thoughts, and worldview out into the world. But a book is also a product. And if you go about creating that product in an intelligent way, if you go about marketing it in an intelligent way, a lot of the systems that are designed to sell books and deliver books at this stage in human experience are very sophisticated.” ~ Josh Kaufman

“I really try to be clear on an introspective level. What do I actually care about? What do I want? What's important to me? If I'm going to make trade-offs between different areas of life and experience, I'd really like the benefit of getting more of what I actually want and getting less of what I actually don't.” ~ Josh Kaufman

“If family is going to be a big part of your life, then that means you're going to be trading off family considerations with something else that could otherwise be. The trick is being very clear and conscious and feeling good about the trade-offs that you're making.” ~ Josh Kaufman

“How would I go about this if I change some of the fundamental assumptions of either what I'm doing, why I'm doing it, or how I'm going to go about doing it? Every single time I've asked that question of a client or of myself, some sort of creative insight, some sort of new approach or strategy has always been the result.” ~ Josh Kaufman

Links