The obstacle is the way



Reading time:

15 minutes
I recently read The Obstacle is the Way by Ryan Holiday. It’s a book that is mentioned frequently by Tim Ferriss and is also part of his book club (his shortlist of important books to read). Ryan Holiday was also recently on the Rich Roll Podcast.
The Obstacle is the Way is basically a modern take on stoicism, something I’ve vaguely came across at some point before but never really took any interest in it. However, stoicism has somehow come up frequently in my conversations and especially in the podcasts I listen to this year. I’m so glad I’ve picked up the habit of listening to podcasts. Such a damn good use of time while I’m riding or walking; it has greatly expanded my mind and change my perspective on many things.
I really enjoyed the book a lot, so here are my notes/reflections from the book that I know I’ll be referring back to time and again. Hopefully it’ll be of some use to anyone else out there reading too. I’ll try to be as concise as possible.

What is stoicism?

Stoicism is a mindset and a practice that helps you get past obstacles and see them in a different light. It may help you to greet adversity with cheerfulness; to treat obstacles as opportunities; to take action and control of our lives; to stop blaming the world and others for the situation you in right now; to stop being a victim, and be empowered.
A key part of stoicism is being aware of our emotions when something disruptive happens to us, and taking emotion out of the equation. Apparently this led to the joke that stoicism is like a cow standing in the rain, unfazed. Haha, but it’s definitely more than that.
I’m sure most people have unknowingly practiced stoicism at some point in their lives but it doesn’t usually come naturally. Like meditation, it takes conscious and deliberate practice.
Stoicism can be seen embodied in many prominent people throughout history. One of the most famous stoics is Marcus Aurelius, the second king of Rome, and the person who the movie Gladiator is based on. I didn’t realise who he was until I read this book. A lot of insights about stoicism can be found in Aurelius’s person diary, Meditations – it is next on my books to read. Other famous stoics include Seneca.

Breaking it down

Stoicism can be broken down into three essential parts: Perception, Action and Will.
Perception is the objective judgement we try to make to determine our attitude and approach to problems.
Action is the unselfish step(s) we take to turn obstacles into opportunities.
Will is the willing acceptance of all external events. It is what helps us handle defeat and difficulty.


  • Objective judgement – to see events, clear of distractions, exaggerations, and misperceptions.
  • When normal people are faced with a problem, their perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues”
  • Objective judgement is helpful, subjective judgement is not. Change perception, change reaction.
  • It isn’t about being positive but to learn to be ceaselessly creative and opportunistic.
  • It’s not “this isn’t so bad”, but it’s “I can make this good” – You want the challenge! Enjoy the ups and downs, embrace change and uncertainty because life would be boring if you knew all possible outcomes
  • Changing perspective is more than just seeing the glass half full. It looks past the glass through to the other side to the positive.

“desperation, despair, fear, powerlessness – these reactions are functions of our perceptions […] you must realise: nothing makes us feel this way; we choose to give in to such feelings.”

  • E.g. regarding “fat shaming”, a recent topic in mainstream media – There’s that idea that nobody else can shame you except yourself. It would be ideal if people can snap out of feeling sorry for themselves and being offended, but as Holiday mentions in the book, the process of objective judgement is simple to understand but may be difficult to execute.
  • We are living in a great time in human history – “we’re soft, entitled, and scared of conflict. Great times are great softener” – Wim Hof, “The Ice Man”.
  • Don’t let yourself get too comfortable, it makes you soft.
  • When you find yourself reacting emotionally, and losing perspective. Have self-discipline and try to be aware of that state of mind – stop (calm down), reflect (focus on the things you can control), meditate (revert to the present moment), and go to bed (?).
  • Method to be objective: remove “you” the subjective part – from the equation. Think of it as you are giving advice to someone else and not you. Do it with clarity, not sympathy.


  • the action then is to greet our obstacles with:
    • energy, persistence, a coherent and deliberate process, interation and resilience, pragmatism, strategic vision, craftiness and savvy, and an eye for opportunity and pivotal moments
  • Practice persistence and resistance
    • Persist – To know you want to quit but continue to take the next step towards your goal is persistence.
      • never in a hurry
      • never worried
      • never desperate
      • never stopping short
    • e.g when I’m cycling up a grade 10% hill and want to stop but I take a deep breath, try to relax my shoulders, and just keep thinking of pushing one foot after the other

My thoughts:

But what if you completely have a change of heart and your goal has changed? I guess it would depend on how broad the goal is because you may change methods for achieving that goal. But if you’re really changing goals, I think as long as you are honest with yourself and not making a decision out of fear, that’s fine.

  • Resist – giving in to distraction, discouragement, or disorder
    • e.g. Wim Hof in the TFS said his advice to his 30 year old self was to have faith that his breathing method, which he believes enhances the human immune system, and now it is scientifically proven. But before it became credible, people around him, even his family, didn’t take him seriously and called him crazy but he was persistent and resistant to their remarks. Now he is famous for the “Wim Hof breathing method” and people take him seriously.
  • Great line to answer with when people ask “how’s it going”: “we’re working on it. we’re getting closer. when setbacks come, we respond by working twice as hard.”
  • When shit happens and you feel that anxiety building up ask yourself: “do I need to freak out about this?”
    • Answer would probably be: NO (you damn fool *with attitude), because I practiced for this situation and I can control myself. Or, NO, because I caught myself and I’m able to realise that that does’t add anything constructive.
  • But the ability to not act on impulse is difficult that’s why both physical and mental practice is important –
    • Pushes the point why mental strength is clearly so important in MMA for instance. In episode 3 of TUF, coach Conor Mcgregor flips out when his fighter doesn’t listen and isn’t “patient” and doesn’t “adjust for position first over submission”. His fighter had received a lot of hard hits from his opponent and was “broken” meaning he lost his heart to fight and wasn’t thinking clearly and strategically anymore – this is also strongly linked to the concept of Will later.
  • We can’t change the obstacle, the obstacle is the way. What we can change is how we look at things.
    • what we can control, our, emotions, judgements, creativity, attitude, perspective, desires, decisions, determination.
  • The benefits of seeing obstacles as opportunities is that our best ideas come from there, where obstacles illuminate new options.
  • “it’s our preconceptions that are the problem. they tell us that things should or need to be a certain way, so when they’re not, we naturally assume that we are at a disadvantage or that we’d be wasting our time to pursue an alternate course. When really, it’s all fair game, and every situation is an opportunity for us to act.” – strive to challenge assumptions.
  • When you are at the end of your rope and at what you think is your lowest point, that you got nothing else to lose. It’s a unique chance to grow and improve yourself, and experiment with different solutions, try different tactics, or take on new projects to add to your skill set.
  • An example for scientists: if you had a hypothesis and it turned out to be wrong it teaches two things: that your instinct was wrong, and the kind of appetite for risk you really have.

My thoughts:

This reminds me of the growth vs fixed mindset. Someone with a growth mindset doesn’t see limitations in his/her abilities. Someone with a fixed mindset doesn’t believe they can grow or are fixed in their ways. How to cultivate a growth mindset in kids? When they do something well, explain to them, “You did A then B and that’s why you achieved C!”. Don’t tell them, “Wow, you are so smart that you achieved C!” They would think it’s only because they are smart that they are worthy. When they do not succeed in the future, they would feel shame because they did not live up to their “label”. They will feel like they failed. However, the kid with a growth mindset will be able to get past failure quicker and understand that he/she is able to succeed with determination.

  • It doesn’t matter what happens or where you come from, all that matters is what you do after what happens and what you’ve been given.
  • It’s okay to get frustrated or emotional or see things negatively for a moment, just don’t take too long to see past it and get back to work!
  • The most important step is the next step, or starting. Like an aeroplane, you need to gain momentum first before you can fly. And this also involves consistency, no starting and stopping, you’re just wasting energy (momentum).
  • Don’t fear taking action. Don’t wait for the perfect moment. Don’t wait to feel 100%. Take action to feel a 100%. If you want momentum you gotta create it yourself. Get up and get started.
  • When trying to convince people – show them new ways of looking at or understanding the world; don’t challenge their longest and most firmly held opinions.
    • find common ground and work from there
    • or look for leverage to make them listen.
    • or create an alternative with so much support from other people that the opposite voluntarily abandons its views and joins your camp
  • When you feel you are “cheating” – you don’t have to succumb to pressure to match people move for move, stick to what works for you isn’t cheating – you are acting like a real strategist.
  • When the situation seems like a disaster, learn to press forward. See the moment differently, and act accordingly. E.g. if you’re stuck in bed recovering, use that time to do something you always planned to do. Put the disruptive event in your life to good use. You can make a negative event exclusively negative, or you can get past whatever adversity it represents and see the opportunity it presents for a solution.
  • When we perceive things well, act rightly, and fail anyway: in every situation, that which blocks our path actually presents a new path for us; an opportunity to practice some other virtue or skill. Do just your best not the impossible.


If perception and action are disciplines of the mind and body then will is the discipline of the heart and soul.
  • Will is the one thing we control completely always. Whereas I can try to mitigate harmful perceptions and give 100 % of my energy to actions, those attempts can be thwarted or inhibited. My will is different, because it is within me.
    • E.g. it’s that moment when you’re trembling, you feel heavy, your heart is pounding, and you just want to stop during some sort of conditioning exercise, but you’re coach is shouting “20 more seconds, 20 more seconds!”. Do you have the will to push through?
    • E.g. when things just aren’t going smoothly and you encounter obstacle after obstacle, do you have the will to keep pushing forward? But note, this doesn’t meet you keep trying the same thing. It means to keep learning from experience and not sink into despair or hopelessness.
  • Will is fortitude and wisdom. It puts obstacles into context. It gives us ultimate strength, and derive meaning from the obstacles we cannot simply overcome.
  • “to comfort those who suffer too” – it is part of will that allows us to think of others, to make the best of a terrible situation that we tried to prevent but could not, to deal with fate with cheerfulness and compassion.
    • E.g. living a life of service to others. A better world is one where there are no losers. Where we focus on lifting people up instead of bringing them down. Where we stop marginalising people. That means e.g. not denying people basic human rights like food, water, shelter (which are all linked to a minimum wage), or marriage if they want to. And of course not torturing non-human beings who have a ability to suffer and feel pain.
  • The stoic maxim: sustain et abstain. Bear and forbear. Acknowledge the pain but trod onward in your task.
  • Will allows us to think, act, and finally adjust to a world that is inherently unpredictable. It is what prepares us for this and protects us against it, and allows us to thrive and be happy in spite of it.
  • What helps is when we are prepared for obstacles, for things to get tough.
  • How do we build our strength in will? Keep putting pressure on it. Don’t get comfortable. keep putting yourself through challenges, keep practicing. Soon it will be second nature and we can intuitively respond to every situation.
  • Especially when times are good, we should strengthen ourselves and our bodies so that during difficult times, we can depend on it – the reason why we go through practice sessions in sports and encourage errors to be made in practice so that they don’t happen in the real game.
  • Anticipation: visualise every possible bad scenario that could happen. Ask yourself “what if…”. It might be pessimistic but it is better to seem like a downer than to be blindsided or caught off guard.
  • What happens when we practice anticipation: we understand the range of potential outcomes and know that they are not all good. We can accommodate ourselves to any of them. We understand that it could possibly all go wrong and now we can get back to the task at hand.
  • The person who has rehearsed in their mind what could go wrong will not be caught by surprise. The person ready to be disappointed won’t be. They will have the strength to bear it. They are not as likely to get discouraged or shirk from the task that lies before them, or make a mistake in the face of it.
  • Stop focusing on things you would rather have or how you rather things turn out to be. Be grateful for what you have now, imagine how much worse things could have been.

My thoughts:

Something I learnt from the RRP in an episode with his wife Julie – it helps to think of yourself as the servant of a god or whatever higher power that works for you. It can help you cope with adversity because you release your attachment to whatever the outcome is, i.e. you are engaged in detached action. You do what you gotta do, but you are not attached to the outcome. Although I’m not religious, I am somewhat of a spiritual person, and thinking this way really does have a calming effect for me. The stoics often considered events to be the “will of the Gods”. There’s nothing you can do about it (after there is an outcome).

  • Somethings are simply out of our control. So discard your expectation and accept what happens. Love whatever happens to us, and face it with unfailing cheerfulness. It is the act of turning what we must do into what we get to do.
  • When you’re tired or unmotivated think: I get to run today. I get to play Ultimate today. I get to learn something new today. I get to go to school today.

My final thoughts:

In the book Ryan Holiday says, “We don’t get to choose what happens to us but we can always choose how we feel about it. and why on earth would you choose to feel anything but good?”. While I understand where he’s coming from, it’s interesting that meditation expert, Light Watkins, wrote a book called The Inner Gym: 30 exercises for strengthening happiness because happiness is not a choice. In his book he provides steps to practice and train our happiness muscles, which is essentially just meditation!

Happiness is a byproduct of building an inner strength. Once you cultivate this you can be happy without having to think about being happy. Happiness isn’t a choice, it is a practice. Do the inner exercises that will strengthen your happiness muscles.

– Light Watkins

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