Summary from obstacle is the way

I am reading Ryan Holiday’s classic “Obstacle is the way”. Here is the gist (points) and my takes on it:

  • Marcus Aurelias wrote a formula for himself to thrive NOT in spite whatever happens to you but BECAUSE of it.
  • Just one paragraph:

Our actions may be impeded … but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting … The impediment to action advances action. What stands in the way becomes the way

(In the same way, Sri Aurobindo, the Indian mystic wrote, “Ego was the helper, ego is the bar”. )

  • The struggle is the ONE constant
  • Asks Holliday, “Whatever we face, we have a choice: will we be blocked by obstacles or will we advance through and over them?”

I am reading this at a time in my life, when nothing seems to work. There are obstacles all the way. I have known thousands of obstacles on my path. I work with people who would block, find negative things, habitual naysayers, and oppose me in every possible way they can. People are impervious to new ideas and it takes years before an idea gets accepted. Even then, I do not progress a bit. More obstacles. Once a while a good sould struts and sees some value in what I do, and possibly put a good word.

Shall I break down and quit? Join the naysayers and inhibit others? Or shall I break through? I know my choice, and here are some possible pointers and tools.

Move on. He says,

  • Every obstacle is unique but not our responses: fear, frustration, confusion, helplessness, depression, anger.
  • Holliday says achieving success is not the same thing as overcoming failure. While there are books and manuals for success, nothing exists for overcoming failure.
  • But how? Holliday contends that great individuals find a way to transform weaknesses into their strengths. He asks how do they do that?

Holliday has a theory. When faced with obstacles, some of us are gripped with paralytic fear and depression and we end up not doing anything about it. Others transcend this and use this opportunity to transform their lives, and these are the winners. Is there a formula or a model?

Now we are reading the philosophy of the stoics.

  • Use the obstacle as a “fuel” to turn things around.
  • This solution is simple not easy.
  • Ruthless pragmatism
  • Relentless persistence
  • Indefatiguable ingenuity
  • This king places a large boulder in front of the gateway of a city to block entry to the city, then watched hiding at a distance. People came and got turned away, or cursed the king for this action. Then came a peasant, and figured out a way to remove the boulder. As soon as he did so, he was rewarded with gold coins and a note from the king that the obstacle in the path becomes the path and every obstacle is an opportunity.
  • Just as the peasant turned an obstacle into wealth, so can we. Holliday contends that most of our “obstacles” are “internal” (professional frustration, unmet expectations, “learned helplessness”, we have “too much”), less “external”.
  • Three critical steps:
  • Attitude/Approach (“Perception”)
  • Creatively turn them to opportunities (“Action”)
  • Inner will/determinism (“Will”)
  • How we see and understand the world/events around us
  • If you are emotional, subjective, short-sighted — spells doom
  • Limit passions and do not allow passions control lives
  • Learn to see things as they are and be “imperturbable” — events.

(This brings back to notions in insight meditation and zen traditions. Where the teaching is to see things as they are, not what they evoke. For example, if you sit down for meditation and hear a train hooting, note the hooting sound, NOT think that the hooting sound came from a train. It takes a while to get this around. But this is the way you start seeing things as they are. Here, insert notes from Zen and meditation books, will be handy).

  • When Rockefeller was not Rockefeller and a clerk with poor family background; was working on a salary and found himself in the middle of a nationwide financial meltdown. Rockefeller was a cool-headed person, took this as an opportunity to learn. Looked for opportunities (does not tell us how he “learned” to look for opportunities. It cannot be just level headedness, must be something more than that). Then he went on a survey of oil fields but _resisted the temptation_ to purchase. This was the second quality Holliday highlights: self-discipline + objectivity. He was not born with these things (resilience, calmness, adaptable), he learned on the way. Lesson from Rockefeller: “where one person sees crisis, another can see opportunity; where one is blinded by success, other sees reality with ruthless objectivity”. Then he comes up with this line which I felt was brilliant, “Outward appearances are deceptive; what’s within them or beneath them is what matters”.
  • Learn to filter feelings. Stop yourself at the point of reaction. Getting to that precise point takes time. One practice that helps is deliberate mindfulness meditation. Focus on the breath, or when you walk, walking. Listen to your mind, and try to watch yourself.
  • Recipe from Holliday:
  • Be objective
  • Control emotions, keep an even keel
  • Choose to see the “good” (this is the toughest one!)
  • Steady nerves
  • Ignore what disturbs or limits (I’d diverge here: I’d say acknowledge. There is this principle of RAIN — recognise that it is disturbing you, acknowledge that it is OK to be disturbed, investigate the nature of the “suffering” you are undergoing, and do the N = non-attachment, very deliberately detach yourself from the suffering, noting that it is causing you grief, acknowledge that it is OK. I’d probably not IGNORE
  • Place things in perspective (very important)
  • “Revert” to the present moment (absolutely. Do not brood over the past, do not speculate about the future, steady yourself in the immediate moment. Develop a moment-to-moment awareness, very important)
  • Focus on what CAN be controlled. It turns out that you can control your own state, or anything that is within your OWN control. You cannot control others’ decisions.
  • Story of Rubin Carter; a boxer who was unjustly incriminated and jailed. He was primly dressed when he went to jail and told his guards that he would not give up “himself” (his self was in his control). Holliday quotes him saying that he would not allow himself be treated like a prisoner and never be “powerless”.

(My notes: a similar story is told of King Porus of India when he confronted Alexander the Great and was defeated in the war and was taken prisoner. Alexander apparently asked him how would he like to be treated and he responded, “Like a king”. )

Stay put.

Believe in yourself. Have faith in yourself. If you do not believe in yourself, no one will.

Holliday claims that Carter was furious but did not rage. After long years of litigation and legal fightback he was released, but Holliday reminds us a lesson from his life: “I might not have wanted it to happen, but I DECIDE how it will affect me: no one else has the right”. Very similar story with Nelson Mandela in his prison life.

Take control.

If you decide for yourself you’re screwed, that’s when obstacles become obstacles. You do not have to be deluded that everything is rosy, but acknowledge things as they are and refuse to change or cower down.

Let the mistake become a tool of training.

  • Be graceful. Be poised.
  • Holliday quotes Voltaire, who explained the secret of success to Duke of Marlborough, “tranquil courage in the middle of tumult and serenity of soul in danger, which the English call a cool head”. Cool head is very very important.
  • Steel yourself.
  • Do not panic!
  • Story of astronauts who circled the earth and yet controlled their heart beats
  • Calm equianimity. Apathia.

Once again, the allusion to insight meditation comes to mind. A great tool to cultivate this sense of apathia and equianimity. Nothing can move you.

“No, thank you. I cannot panic”.

“Do not panic” is also the mantra of the Hitchhikers’ guide to the galaxy.

If you do not panic, you can spend your energy to SOLVE the problem, not reacting to them.


“What am I choosing NOT to see RIGHT now?” (Gavin de Beker)

“Does getting upset provide me with more options in THIS instance?”

“Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?” No? now, get back to work.

(my notes: if your answer is “yes”, start reading from the top again. You are in a loop. Get out of the loop)

“Do I need to freak out?”

The answer is no!

  • “The perceiving eye is weak, the observing eye is strong” (Miyamoto Mushashi, “Book of five rings”)
  • Perception is a problem
  • When you feel intimidated by someone try visualising that person having sex. (Reminds me of the story of The Buddha where he advised his followers how the body of a beautiful dancer/actress was nothing but a rotting corpse after death: Marcus Aurelias’ description of wine as fermenting grapes)
  • Being objective == removing “you”
  • Perspective is everything
  • When you break apart X and look at it from a new angle, it loses its power
  • When fear strikes, break it apart
  • RH cites the story of George Clooney, who got several rejections, till he started analysing the selection process from the perspective of other teams and producers. This was his turnaround
  • Tommy John’s phenomenal long run in baseball was because he was dour and resilient, and always gave his 100%.
  • Remember the Serenity Prayer, “ God, grant me the serenity to accept things I cannot change; the courage to change things I can, and the wisdom to know the difference”
  • Very important to differentiate between what is up to us/What is NOT up to us
  • What is up to us: (emotion, judgment, creativity, attitude, perspective, desire, decision, determination); not up to us (everything else)
  • My promotion decision is NOT up to me: but to push for more publications, apply for a million fundings till I get one, relentlessly pushing the boundaries till they notice is up to me.
  • Stop wasting time on things that are not up to you, but need to know what is not up to you. Don’t spend time on that.
  • What matters is that right now is RIGHT NOW
  • Things that can pull us in the present moment:
  • Strenuous exercise, unplugging, walk in the park, gardening, meditation, pet,
  • Catch your mind, do not day dream. Catch when you are daydreaming and come back to the present
  • Steve Jobs: reality distortion field
  • “There shall be no Alps” (Napoleon)
  • Be open. Question everything!
  • Do not listen to naysayers, do not naysay (but be prepared for the worst and do pre-mortem, see later)!
  • Story of Mac: if they could do in two weeks, they could do in one week!
  • Tell yourself: I can do it! Set deadlines, impossible goals, reach for the stars!
  • When failure strikes, ask “what went wrong here? what can be improved? what am I missing?”
  • Do not be wedded to a position
  • Do not be afraid to lose
  • Do not be bitter or embarrassed
  • Do not stay out of the game for long
  • Slip as many times as you have to, but do not fall!
  • Failure is the best teacher. Learn from failures!
  • Failure tells us what ISN’T the way
  • Break down everything to pieces
  • Then do what is needed NOW!
  • Do it well, move to the next step
  • FINISH what you are doing now, no matter what it is! Finish.

(notes: as Jim Romeis says, a “done thesis” is a good thesis. Finish)

(note: a similar lesson was with Saurav Ganguly, the cricketer. He used to play the game ball by ball, session by session. Just do what is needed now).

  • Connect everything. Order them. Do them.
  • Do not be distracted. Do not be disordered/disorganised.
  • the process is about doing right things RIGHT NOW.
  • Work hard. Be honest. Help others as best as possible. Keep doing.
  • Don’t go expecting Plato’s republic.
  • Think progress not perfection
  • If you are faced with a tough opponent or tough situation, remember that you can’t push back, instead keep pull until the opponents lose their balance, then make your move!
  • Soren Kierkegaard’s example: he did not lecture but write under pseudonyms (“indirect communication”), offering multiple perspectives. When you find people who won’t move from their positions, find first a common ground, or create an alternative with so much support from other people that the oppostion voluntarily abandons the views.

(Example: I once tried to push R/open source software to my workplace and figured out that people did not like that idea. They would rather use an expensive non-free solution. But I also found that when I did not force, or try too hard, but stuck to my own practice practice, I could get more and more interested people around me, then use data/software carpentry and build the strength with more interested people, then watch how their dominoes fall over and they join your camp. Do not force, but bypass)

  • Don’t waste your energy with ego and pride. (notes: Sri Aurobindo’s advice: ego was the helper, ego is the bar)
  • Sometimes the longest way around is the shortest way home.
  • Gandhiji’s example:
  • Withdraw and let them attack you, and then turn them against themselves
  • Meet physical force with soul force
  • Use the power of opposites
  • Restraint might be a better option. Wait for temporary obstacles to fizzle out.
  • Don’t spin your tires in the mud or dig a deeper rut.

(Yihui Xie’s dictum in knitr in a nutshell, “… when you are in a hole, stop digging”)

  • Moving forward is NOT the only way to success, sometimes staying put and going sideways works equally well.
  • Arthur Ashe would mask his emotions etc on court but channelled this energy to make his game fluid.
  • Be free inside, there it matters!
  • Joe Louis, steely, blank
  • Be physically loose but mentally restrained. Do not have to show your emotions. It doesn’t matter. Work. Act where it matters.
  • “You do not want a serious crisis to go waste. Things we had postponed for too long are now immediate and must be dealt with. A crisis provides the opportunity to do things that you did not do before”, RH cites Rahm Emanuel, and tells the story of Obama campaign of 2008.
  • Nothing can ever prevent us from trying.
  • Problems are a chance for us to do our best (Duke Ellington)
  • Be cheerful even in dark times
  • Quiet humility, resilience, and flexibility
  • Story of Abraham Lincoln, never gave in to hopelessness
  • “This too shall pass”
  • “Inner citadel” — fortress inside us, must be built, we are not born with it.
  • Strengthen yourself during good times so that you can sustain during bad times
  • Premortem or premeditation of evil
  • Make concessions for the world around you. If these come as constant surprises each time they occur, something’s wrong
  • “Beware the calm before the storm; hope for the best, but prepare for the worst, the worst is yet to come, and it gets worse before it gets better”
  • Learn to say, “C’est la vie. It’s all fine”
  • Appreciate that “things could be worse”
  • Persist and persevere
  • We’re just humans. Someone before me has gone through this, someone after me will go through this. I am not unique but I can do what I can to help others. Be selfless
  • Behind mountains are more mountains. Elysium is a myth. Life is a marathon. Never be rattled.
  • See clearly. Act correctly. Endure and accept the world as it is.
  • A stoic is a person who transforms fear into prudence, pain into transformation, mistakes into initiation, and desire into undertaking” (Nassim Nicholas Taleb)
  • See things what they are. Do what we can. Endure and bear what we must.

A great takeaway from the book is to read “Meditations” by Marcus Aurealias. My next project.



Professor @ University of Canterbury, Doctor, scholar, data scientist, Cantabrian. ENS: arinbasu.eth & mastodon instance:

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Arindam Basu

Professor @ University of Canterbury, Doctor, scholar, data scientist, Cantabrian. ENS: arinbasu.eth & mastodon instance: