Books Like
The Obstacle Is the Way

If you liked The Obstacle Is the Way, the closest books are Meditations by Marcus Aurelius, Ego Is the Enemy by Ryan Holiday, Man’s Search for Meaning by Viktor Frankl, You Are Capable of More by Chris Sund, A Guide to the Good Life by William B. Irvine, How to Think Like a Roman Emperor by Donald Robertson, Option B by Sheryl Sandberg and Adam Grant, and Antifragile by Nassim Nicholas Taleb. Meditations is the natural next read, because so much of Holiday’s book grows out of it.

What The Obstacle Is the Way does well, and what it leaves out

Holiday took a single line from Marcus Aurelius, rendered in the Gregory Hays translation as “the impediment to action advances action; what stands in the way becomes the way,” and built a short, readable book around it in three parts: how you see a problem, what you do about it, and the will to keep going when doing is not enough. His real gift is that he makes an ancient philosophy feel like something you could use at work this afternoon, without asking you to read any ancient philosophy first. That is no small thing.

What it leaves out is ordinary life. Most of the stories are about famous people facing famous obstacles, which can quietly suggest that resilience belongs to extraordinary people, when most of us are dealing with a missed promotion, a hard conversation or a week that simply did not go the way we hoped. When I surveyed more than 200 working adults for my own book, 71 percent said they fall short of their own expectations every week, and 92 percent said they were capable of more than they were doing. For most people, setbacks are not a once-in-a-lifetime test. They are a Tuesday.

One

Meditations by Marcus Aurelius (Gregory Hays translation, 2002)

These are the private notes a Roman emperor wrote to himself, in the second century, while he was leading an empire through war and plague, and they were never meant for anyone else to read. That is exactly what makes them so moving, because you are watching a person talk himself back to patience and courage on hard days, and the Hays translation makes it read like plain modern English.

It is not a book with a plan or a clear order, and it repeats itself often. It works best kept by the bed and opened a page at a time, rather than read straight through like a self-help book.

Two

Ego Is the Enemy by Ryan Holiday (2016)

Holiday’s next book turns the lens inward, arguing that the obstacle we most often face is the one we create ourselves, through pride when things are going well and through self-pity when they are not. It uses the same short chapters and story-driven style, so readers who enjoyed the first will feel right at home.

That familiarity is also its weakness. If you have just finished The Obstacle Is the Way, some of the structure and a few of the characters will feel like ground you have already walked.

Three

Man’s Search for Meaning by Viktor Frankl (1946)

Frankl, a psychiatrist, survived the Nazi concentration camps and wrote about what he saw there: that the people who held on longest were often those who still had something to live for, and that even when everything else is taken, a person can still choose their attitude toward what is happening. It is the deepest book on this list, and the strongest proof that the Stoic idea is not just a productivity trick.

It is heavy reading, as it should be, and the second half on Frankl’s own therapy method is drier and more clinical than the first. It is not a how-to book, and it should not be read as one.

Five

A Guide to the Good Life by William B. Irvine (2009)

Irvine is a philosophy professor who set out to practice Stoicism himself, and this is the clearest plain-language guide to how it works day to day, including techniques like imagining losing what you have so you appreciate it more, and sorting what is in your control from what is not. If Holiday made you curious about the philosophy itself, this is the most patient place to learn it.

It is more academic than Holiday in places, and some readers feel Irvine’s modern adjustments drift a little from what the ancient Stoics actually taught.

Six

How to Think Like a Roman Emperor by Donald Robertson (2019)

Robertson is a cognitive behavioral therapist, and he weaves the life of Marcus Aurelius together with practical exercises drawn from modern therapy, which shows how closely the two traditions line up. It is the best book on this list for readers who want to understand why the Stoic approach to setbacks works, not just that it does.

Because it alternates between biography and technique, it moves more slowly than Holiday. Casual readers may find it more than they wanted.

Seven

Option B by Sheryl Sandberg and Adam Grant (2017)

Sandberg wrote this with Grant after the sudden death of her husband, combining her own grief with research on how people rebuild after loss. I include it as the gentle counterweight, because not every obstacle is an opportunity in disguise, and some setbacks need to be grieved before they can ever become fuel.

It is written from a position of wealth and support that most readers do not have, which the authors acknowledge. Even so, its kindness toward people who are struggling fills a real gap in the Stoic shelf.

Eight

Antifragile by Nassim Nicholas Taleb (2012)

Taleb argues that some things do not just survive stress and disorder but actually grow stronger because of it, and he applies that idea to bodies, businesses and whole societies. It is the big-picture version of Holiday’s theme, and it gives a useful name to the hope that hard seasons can leave us better than they found us.

It is long, wandering and often combative in tone. Many readers will get the most from skimming for the central ideas rather than reading every page.

Which one to pick

If you want one, read Meditations. If the setback in front of you feels too personal for philosophy, start smaller, with something you can do this week, and there is a gentle guide to that in how to learn from a setback without carrying it.

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