The Obstacle is the Way

First, see clearly.

Next, act correctly.

Finally, endure and accept the world as it is.

The Obstacle is the Way by Ryan Holiday introduces stoic philosophy. It’s a practical philosophy for thriving in life’s crucible. Stoics follow a path of understanding perception, acting correctly, and accepting things for what they are. The Obstacle is the Way introduces these concepts with real world examples and references from well known stoic philosophers like Seneca or Marcus Aurelius. In fact, Meditations is probably the most quoted source. This is no surprise given Marcus Aurelius prevalence in stoic circles. The text is approachable to a wider audience. No prior philosophical education is required. Reader will take away some practical advice for dealing with their struggles.

I immediately connected with the book. My life in the past few months has not been straight forward and new obstacles are appearing all the time. It’s natural to feel overwhelmed and awash in the current of uncontrollable events. The title is no accident. There’s only one way forward: through. Through the obstacles. I think we understand this deep down. We may be scared, intimidated, uncertain, unconfident, baffled, or anything else that prevents us from overcoming what ails us. These obstacles may seem too large upon initial inspection. That’s our emotions taking over. First we must understand our perception before acting.

Perception

There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.

The quote comes from part one on perception. We perceive events in two dimensions. There is the objective reality and the subjective story we tell ourselves. The story may sad: “how could this possibly happen to me!” or “what could I do to deserve this”. The may also be happy: “That worked out so much better than I thought!”. Those three narratives include the all powerful “I” context. That’s where things go off track and become emotional.

Humans are emotional and rational. Emotion comes before reason for many of us. Emotion tends to cloud reasonable action. However emotions cannot be ignored. That would mean to ignore what makes us human. Emotions should be domesticated. One should learn to let them move through and onward to act with a stoic cool headedness on the task at hand.

What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand. Think of it as selective editing — not to deceive others, but to properly orient ourselves.

Acting on the task requires categorizing what is under our control and not, then intensively moving the levers under our control. Putting energy into anything else creates disappointing since we never had control over the outcome in the first place. This orientation creates a new perception: one where we’re not seeing an obstacle, but an opportunity.

Action

We’ve all done it. Said: “I am so (choose one) overwhelmed, tired, stressed, busy, blocked, outmatched.”

And then what do we do about it? Go out and party. Or treat ourselves. Or sleep in. Or wait.

It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.

Stoicism relies on action. The only way forward is through. Going through requires action. Action to change the situation, adapt oneself, or find a way around. All actions may not take us to the desired place. The most desirable course of action may not be always be possible, in fact, it seems rarely achievable. This requires acceptance and will. The author puts it best:

It’s an infinitely elastic formula: In every situation, that which blocks our path actually presents a new path with a new part of us. If someone you love hurts you, there is a chance to practice forgiveness. If your business fails, now you can practice acceptance. If there is nothing else you can do for yourself, at least you can try to help others.

This is simple (not easy) because it requires strong will.

Will

Will is fortitude and wisdom — not just about specific obstacles but about life itself and where the obstacles we are facing fit within it. It gives us ultimate strength. As in: the strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome (which, as it happens, is the way of flipping the unflippable).

Part three covers will. Will is perseverance. All obstacles are not created equally. Consider Theadore Roosevelt who lost is mother and wife in the same day. One can only imagine the suffering on that day and will required to overcome it if not for ourselves then for others.

Part three includes the insight that we may not be able to make a difference for ourselves, but we can help others in similar situations. Thus, there is true in good in all situations.

The second insight is preparedness. We can always prepare ourselves for multiple outcomes. We can, and should, plan for scenario A, B, and C then accept and bear the outcomes. The author mentions Dwight Eisenhower on eve of invasion of Sicily. Everything had been analyzed and prepared in the event of success or failure. The only thing left was to roll the dice and see how things came out. Both possibilities were prepared for.

My last highlight comes from the end of part three:

On the contrary, the more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.

This likely rings true for many of us. We’ve felt our problems scale up as we grow older and life becomes more complicated. We get married, have children, start businesses, or move to different countries. Things are never going to get easier. Our successes breed bigger obstacles. Consider Bill Gates. His first obstacle was business. His next obstacle is improving the world via philanthropy and unique business ventures. Obstacles have shifted away from him and towards others. Hopefully more of us grow a sphere influence that large.

Closing Thoughts

“The Obstacle is the Way” contains practical advice for anyone looking to improve their life. It’s simple (but not easy). This reminds me of Rich Hickey’s talk on Simple Made Easy. The distinction is clear. It’s simple enough moderate perception, but not easy to domesticate our emotions. It’s simple to act with intent, but not easy when the path if fraught with trade-offs. It’s simple to maintain will, but not easy in the face of unending adversity (some call this life). Stoic tools make it easier. This book introduces the tools and sets you off.

Miscallenous Highlights on Perception

On understanding our emotional attachments:

Where one person sees a crisis, another can see opportunity. Where one is blinded by success, another sees reality with ruthless objectivity. Where one loses control of emotions, another can remain calm. Desperation, despair, fear, powerlessness — these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings.

On emotional influence:

Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things. Unhelpful perceptions can invade our minds — that sacred place of reason, action and will — and throw off our compass.

A cool head:

We must possess, as Voltaire once explained about the secret to the great military success of the first Duke of Marlborough, that “tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head.”

On the way through:

Defiance and acceptance come together well in the following principle: There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

On fear and uncertainty:

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity. Fortunately, unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty.

On unhelpful emotion:

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.

On one’s purpose:

What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand.

On perception:

Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph?

Miscellaneous Highlights on Action

On focus:

Remember and remind yourself of a phrase favored by Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

On being an asshole (one my favorites!):

Only self-absorbed assholes think they are too good for whatever their current station requires.

On moving sideways:

We wrongly assume that moving forward is the only way to progress, the only way we can win. Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path.

There is a certain humility required in the approach. It means accepting that the way you originally wanted to do things is not possible. You just haven’t got it in you to do it the “traditional” way. But so what?

On obstacles

At certain moments in our brief existences we are faced with great trials. Often those trials are frustrating, unfortunate, or unfair. They seem to come exactly when we think we need them the least. The question is: Do we accept this as an exclusively negative event, or can we get past whatever negativity or adversity it represents and mount an offensive? Or more precisely, can we see that this “problem” presents an opportunity for a solution that we have long been waiting for?

Miscellaneous Highlights from Will

On situational behavior:

In every situation: we can

Always prepare ourselves for more difficult times.

Always accept what we’re unable to change.

Always manage our expectations.

Always persevere.

Always learn to love our fate and what happens to us.

Always protect our inner self, retreat into ourselves.

Always submit to a greater, larger cause.

Always remind ourselves of our own mortality.

And, of course, prepare to start the cycle once more.

On traffic signals:

You know you’re not the only one who has to accept things you don’t necessarily like, right? It’s part of the human condition. If someone we knew took traffic signals personally, we would judge them insane.

On acceptance and smiling:

The next step after we discard our expectations and accept what happens to us, after understanding that certain things — particularly bad things — are outside our control, is this: loving whatever happens to us and facing it with unfailing cheerfulness.