Chris Guillebeau's Book Recommendations (Updated for 2026)

1

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

Ryan Holiday

4.4

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

We are stuck, stymied, frustrated. But it needn’t be this way. There is a formula for success that’s been followed by the icons of history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—a formula that let them turn obstacles into opportunities. Faced with impossible si

Recommended by James Altucher, Marvin Liao, Alok Kejriwal, and 19 others.

Chris Guillebeau

First came Marcus Aurelius, then Frederick the Great... and now there's you. This surprising book shows you how to craft a life of wonder by embracing obstacles and challenge. [source]

James Altucher

Founder/StockPickr

My life has been beset with obstacles. It takes practice (and pain) to surmount them and achieve success. This author’s book is a how-to guide for just that. [source]

Marvin Liao

Partner/500 Startups

My list would be (besides the ones I mentioned in answer to the previous question) both business & Fiction/Sci-Fi and ones I personally found helpful to myself. The business books explain just exactly how business, work & investing are in reality & how to think properly & differentiate yourself. On the non-business side, a mix of History & classic fiction to understand people, philosophy to make sense of life and Science fiction to picture what the future could be like (not always utopian). [source]

2

Juliet's School of Possibilities: A Little Story about the Power of Priorities

Laura Vanderkam

4.3

A charming, life-changing fable that will help you rethink your whole approach to time, priorities, and possibilities.

Riley Jenkins is in trouble. An ambitious, hardworking consultant in her late twenties, she's used to a lifetime of nearly perfect evaluations - until she gets a terrible performance review from her boss. How is that possible when Riley does everything her clients want - including

Recommended by Gretchen Rubin, Alissa Carpenter, and Chris Guillebeau.

Chris Guillebeau

Laura is my go-to expert for time management and Juliet's School of Possibilities is a delightful book. You can read it in a couple of short sittings, then go away with a lifetime of application. [source]

Gretchen Rubin

Author

Thousands of books explain how we should set priorities, stay focused, and make time for what truly matters—but that advice, however sound, is all too easy to ignore. Laura Vanderkam takes a different approach. By harnessing the irresistible power of story-telling, she makes those aims vivid and compelling in an entirely new way, to show us how and why we can make room for possibilities. [source]

Alissa Carpenter

One of my favorite experts on time management and productivity @lvanderkam released a new book, Juliet's School of Possibilities! https://t.co/12kBFrvimV She's also giving away a free time makeover guide and time sheet and I needed to share! https://t.co/fXrE63NHX6 [source]

3

Superfans: The Easy Way to Stand Out, Grow Your Tribe, and Build a Successful Business

Pat Flynn

4.5

Preview Summary

Customers, followers, subscribers.

It's easy to just look at the numbers. How many likes? How many purchases? How many email subscribers?

But as entrepreneurs, we have to remember that there are people behind all that data. People who are looking to us to be a leader, to give advice, and to care. In this dog-eat-dog world, these are the people who are looking for someone who they can trust, and who

Recommended by Amy Porterfield, Chris Ducker, Chris Guillebeau, and 2 others.

Chris Guillebeau

After you read it, you'll go away feeling motivated and ready to work. [source]

Amy Porterfield

Superfans should be required reading for anyone wanting to build an authentic business that lasts forever. [source]

Chris Ducker

Have you pre-ordered your copy of @PatFlynn's new book, "Superfans" yet?! If not, jump on before August 13th and he'll throw in the AudioBook version for free, too! It's a GREAT read, y'all. Pre-order here: https://t.co/6B2Jb5qjYq https://t.co/gQlzkGBfcy [source]

4

Lost and Founder: The Mostly Awful, Sometimes Awesome Truth about Building a Tech Startup

Rand Fishkin

4.5

Rand Fishkin, the founder and former CEO of Moz, reveals how traditional Silicon Valley "wisdom" leads far too many startups astray, with the transparency and humor that his hundreds of thousands of blog readers have come to love.

Everyone knows how a startup story is supposed to go: A young, brilliant entrepreneur has an cool idea, drops out of college, defies the doubters, overcomes all odds, m

Recommended by Nir Eyal, Seth Godin, Chris Guillebeau, and 2 others.

Chris Guillebeau

This is a truly courageous book. It's one part business-building guide and two parts Indiana Jones-style adventure memoir. And if you've ever wondered if the 'timeless wisdom' you often hear about startups is bullsh*t, here's the proof. [source]

Nir Eyal

Author/Hooked

You won't find a more honest, raw, and helpful look into the trenches of founding a tech startup than this book. Rand Fishkin shares the rare hard-won insight no one else dares tell you. [source]

Seth Godin

Author, Marketer, Entrepreneur

Rand Fishkin is the real deal. This book is an honest, generous and useful look at what actually happens when you build a company, including the downs as well as the ups... I wish I had read it thirty years ago. [source]

5

Ultralearning: Master Hard Skills, Outsmart the Competition, and Accelerate Your Career

Scott H. Young

4.3

Preview Summary

Now a Wall Street Journal bestseller.

Learn a new talent, stay relevant, reinvent yourself, and adapt to whatever the workplace throws your way. Ultralearning offers nine principles to master hard skills quickly. This is the essential guide to future-proof your career and maximize your competitive advantage through self-education.

In these tumultuous times of economic and technological change, stayi

Recommended by Cal Newport, Barbara Oakley, Chris Guillebeau, and 2 others.

Chris Guillebeau

This book is an invaluable tool to help you master complicated skills in a short period of time. Read Ultralearning and level up your life! [source]

Cal Newport

Author

Ultralearning is like a superpower in our competitive economy. Read this book! It will change your life. [source]

Barbara Oakley

Ultralearning is the best book on learning I’ve ever read. It’s a beautifully written, brilliantly researched, and immediately useful masterpiece. If you are looking for the magic match to help light your learning, Ultralearning is it. If you want to learn anything, do yourself a favor and read this book. Now. [source]

6

Company of One: Why Staying Small Is the Next Big Thing for Business

Paul Jarvis

4.2

Preview Summary

What if the real key to a richer and more fulfilling career was not to create and scale a new start-up, but rather, to be able to work for yourself, determine your own hours, and become a (highly profitable) and sustainable company of one? Suppose the better—and smarter—solution is simply to remain small? This book explains how to do just that.

Company of One is a refreshingly new approach centered

Recommended by Cal Newport, Ben Chestnut, Chris Guillebeau, and 1 others.

Chris Guillebeau

You’re not a machine, so why would you run your business like one? Company of One shows you another way. If you’ve ever wondered how to have a business that works for you—instead of the other way around—you need this book. [source]

Cal Newport

Author

Jarvis makes a compelling case for making your business better instead of bigger. Company of One is a must-read for any entrepreneur who prioritizes a rich life over riches. [source]

Ben Chestnut

Founder & CEO/MailChimp

Ever since starting MailChimp 18 years ago, I’ve always been told that my way was wrong. My way has never been to “be big.” My way was always to “be useful.” My company has become a global brand with millions of customers, over $525 million in annual revenue, and almost 1000 employees united by a single mission to help companies of one and entrepreneurs. Go figure. There’s not one, right way. Only your way. Paul’s book, Company of One, can help you find your way. [source]