The Obstacle Is the Way by Ryan Holiday Book Review & My Reflections

A review of Ryan Holiday's 'The Obstacle Is the Way.' Practical insights into overcoming life's challenges through Stoic principles.

Hey guys, The time and date are as per usual. So today I hit a milestone. I’ve listened to 26 hours of Audible this month - which is very likely my all-time record for a month. I aim to get it to 45 hours per month from June onwards (i.e. 90 minutes per day), with a baseline of 30 hours (60 minutes per day) and that is to be the standard moving forward. So the milestone is having finished 5 books in the last 2-weeks. Atomic Habits, Digital Minimalism, Deep Work, Essentialism & now The Obstacle is the way. The final being by Ryan Holiday is the subject of today’s blog. From that list of five, this book has had the least impact upon me I think (which doesn’t mean it’s not good!) - but that may be well to do with the fact that I had some huge errors that needed resolving in my general routines. Holiday’s book is inspired by Stoic philosophy (something which I thought I knew to be - but realise that I’ve grown up with a Stoic - more on this later). Seneca, Marcus Aurelius, Epictetus and more - authors whose works I’ve never read. The guiding philosophy for Ryan’s book is one that I admire. It centres around the idea that we should focus upon only that which is within our locus of power. We should not decry anything that befalls us. We shouldn’t complain, and we should shut up and get on with it. The ‘aha’ moments that came from reading this book were thinking about our mortality - that many of us walk around acting like we’re immortal when in fact death is a certainty and we’re all dying. This gives life a lot more meaning I think and means you should live powerfully. For someone who struggles with mindset, pushing through and taking yourself to the next level I think there’s a lot to be taken from this book. Indeed I got some snippets of insights about persistence, not genius nor insight being the key to success. The assumption that some discovery will lead to outstanding results is false - and that success is founded upon dogged persistence and finding 10,000 ways that will not work until you find the one that does. There are a couple of reasons why perhaps this book didn’t leave me as ‘wowed’ as the others that I read. [convertful id="197358"] It’s the lack of practical guidance/practical application to these concepts in my life. There weren’t enough ‘aha’ moments in the book where I read something and felt I could correlate that with immediate action in my life. That could well be for a couple of reasons which I’ll briefly outline:
  1. The British have a relatively stoic mindset - i.e the ‘stiff upper lip’ mentality
  2. Being from a migrant family, putting up and shutting up is a big part of the working class + immigrant ethos instilled in us
  3. My dad worked for 40+ years without ever complaining about his situation, money or his work. He didn’t say anything unless it was necessary much of the time as well - he’s a stoic in my ways
  4. Having spent a little bit of time running ultras, competing in Ironmen, applying to the SAS, and reading David Goggins ‘Can’t Hurt Me’ - I feel the parallels
I think, being honest - this is why this book might have had less of an emotional impact upon me. Of course - it could also well be that before reading this I’d already got through 20 hours of listening time and therefore 35 hours of audio. I.e my brain said enough! Looking at the table of contents though - there are a couple of snippets that feel memorable and useful - ‘Live In The Present Moment’ is good - similar to Mckeown’s ‘What’s Important Now’? Rather than worrying about X/Y/Z strategy or competitor or otherwise - the focus upon problems you can solve here and now and immediately is powerful. This is something I like to do a lot - ultimately taking massive action in the present moment and then fine-tuning and adjusting as you go. The same way I’ve got through 45.5 hours worth of content in the last 2 weeks. Don’t overthink things - just go for an all-out assault and solve problems as they come up along the way. The chapter on ‘Steady Your Nerves’ is excellent as well. Something I’ve never done very well is cope with stressful situations. I often let my emotions (and NOT the situation) get the better of me and become defensive/aggressive/accusatory in such environments. The idea then that we need to throw ourselves headfirst into such environments then to build familiarity with to lose the emotions sounds really effective. Something I definitely don’t do! Part two and part three are dedicated to Action and Will The book for me finished stronger than it started. Action is something that hugely speaks to me - and focusing more on reflection and education these last two weeks has certainly been a challenge for me. Practising persistence as a cornerstone of success is something that I need to get more effective at - and Holiday always demonstrates with each recommendation he has - plenty of evidence to support his argument. Focussing upon the process rather than the outcome is huge also. i.e forget about your £x target. Just aim to be on 5 sales calls a day and the rest will follow! I think that my process has suffered as I’ve seen more success - and I lost some of the fundamentals. There are several other lessons Holiday teaches all captured within the book - which is worth reading. Especially if you’re someone who gets lost in their own head. I know I certainly do, and in several areas of my life I’m ultimately taking the easy road and not seeing the results I should be having as a consequence. In short - I definitely would recommend this book to anyone who feels they would benefit from having a stronger mindset. My biggest takeaway from this is realising I’m taking the easy path with Word Pigeon in trying to hire a CEO - first of all, I need to focus upon delivering sales myself and seeing what results that brings. Ultimately it goes back to Cal Newport’s ‘Deep Work’ and the great learning I had from there. That I can’t focus, I barely do deep work and getting there will take time. But I will keep pushing no matter what - as Holiday recommends! Push through, go around, or don’t react but respond to the obstacle (whether death, drugs, disease, business failure or anything else). Because the Obstacle is the way.