The Obstacle is the Way
The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do. Its many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), an NBC sportscaster (Michele Tafoya), and the coaches and players of winning teams like the New England Patriots, Seattle Seahawks, Chicago Cubs, and University of Texas men’s basketball team. The book draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.” Ryan Holiday shows us how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck. If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era.
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47recommend
74mentions
62people
2014–2025years
74% recommend20% neutral5% critical
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What Hacker News says
- A related read: 'The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph' by Ryan Holiday
- You'd like this book
- The Obstacle is the Way - Ryan Holiday
Holiday, in most of his books, makes stoic philosophy relatable and gives examples of we'd be familiar with in modern day. It's a fairly easy read, and I gift it the most as well.
As a software engineer, I found his less popular book Perennial Seller to also be very good. It describes his writing style, which honestly is very similar to coding, but also talks about his approach to marketing his books, which drives the content.
Play Bigger by Al Ramadan (and a few others) which talks about category design. I haven't tried their newer books, but I'm somewhat tempted.
- That sounds stressful.
There's a short book I like called The Obstacle is the Way by Ryan Holiday that talks about dealing with adversity like this.
The secret is to take full responsibility for your situation. Nobody will be more invested in your success than you are.
Ask yourself - why do you feel stagnant, and what can you do about it?
For example, talking to your manager about it, making a plan and working toward a promotion as an IC, taking over a struggling project and leading it to success, or transitioning into leading a team.
If it's changing jobs, take responsibility for understanding your goals and finding a role that fits.
And don't lie, that stuff catches up to you.
- Probably myself. I am pretty much always content.
Though, I get the sense that because I am chill and not manic, others sometimes think "something is up" when I'm just thinking about black holes or something. The key point here may be "the happiest person you know may not be obvious." I tend to equate manic happiness with stress and anxiety.
Some perhaps key points:
- I constantly run into challenges and roadblocks in life, but acknowledge they are a normal part of growth. I recently read the popular book The Obstacle Is The Way and it felt like somebody was stealing parts of my life philosophy out of my head.
- I'm not really into "gamification", but I tend to treat everything like a game or a puzzle to solve, especially hardships.
- Often things don't happen to you. They happen regardless of you. Or you caused it, so fix it.
- Exercise to think and de-stress. Often, no music or podcasts, to force the former.
- I used a lot of hallucinogens in my younger years and had a few key trips that really framed life and reality for me. Rather than attempt to explain and fumble it, I'll point you to another book that does a better job of it: Illusions by Richard Bach.
- There is no single answer. You search for and decide what makes life meaningful for you.
There are a lot of great answers in this thread, I particularly like inphovore and Waterluvian's, but yours might be different.
You need some minimal things to find happiness, enough food, shelter, and health. Sadly, in the US, we don't get those things, but there are places that can help you. You may need to move. You may need to live with family, friends, or strangers to get started on your journey. But, you must start your journey and only you can do it.
Read quotes from Mark Twain, The Obstacle is the Way, and The Conquest of Happiness.
Do something that brings you joy and embrace it -- this is particular hard for me. I'm still searching after 50 years.
