Photo on 8-6-16 at 5.45 PM #3

Peter and I listen to The Tim Ferriss Show every week. As a result, we are richer intellectually, physically and spiritually. The only way we aren’t richer is financially, since we’re suckers for the books Tim recommends. We figure it’s a worthwhile trade off.

The Obstacle is the Way by Ryan Holiday is one such recommendation: arriving on our doorstep mere days after it was mentioned on the podcast (Marry me, Amazon Prime!).

The book is based around the Roman philosophy of stoicism. Stoicism is something that is practiced by those who would prefer to maintain calmness in the face of frustration.

The philosopher and writer Nassim Nicholas Taleb describes a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.”

Um, yeah, okay – sign me up for that. Sounds very zen.

In all seriousness, as someone who has actively avoided anything with “philosophy” in the description, I was surprised at how inspiring I found this book. Holiday does an excellent job breaking down Stoic philosophers’ ideas into modern day advice. (And I freaking LOVE modern day advice.)

Here’s some key takeaways for me. About half of these are now personal mantras. (I told you it was a good book!)

Loving your fate

A key idea, reinforced frequently throughout the book, is “amor fati” – love your fate. Anything that happens around you, or to you, must not only be okay with you, but be the best thing that could have happened.

Holiday writes, “No-one is talking glass half full platitudes here. This must be a complete flip. Seeing through the negative, past its underside, and into its corollary: the positive.”

This isn’t an excuse not to reach your goals, to love your fate no matter what and not reach for more. No – Holiday argues that by loving your fate (the things you can’t control) you can more easily navigate past the obstacles towards your goals, with a clear head and happy heart. Loving the journey without being attached to any one route.

“Think water. When dammed by a man-made obstacle, it does not simply sit stagnant. Instead its energy is stored and deployed, fueling the power plants that run entire cities.”

Becoming Immune to External Stressors and Limitations

We’ve all met someone (or in my case, live with someone) who never seems ruffled, concerned, or angry. When faced with adversity, they break down the tasks in front of them into pieces and calmly get back  to business.

Isn’t that annoying?

Holiday says that advantage is available for each of us to gain. We can all be that calm person unfazed by traffic, a bad boss, a stolen laptop, a missed opportunity.

He writes of Stoicism: “It’s a power that drives our opponents and competitors nuts. They think we’re toying with them. It’s maddening – like we aren’t even trying, like we’ve tuned out the world. Like we’re immune to external stressors and limitations on the march toward our goals. Because we are.”

Embracing Crisis

Holiday quotes Obama’s advisor, Rahm Emanuel, “You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. A crisis provides the opportunity for us to do things that you could not do before.”

Loving the crisis (loving your fate) is the way to embrace the stress, use it to your advantage, to push past barriers, and get stuff done.

(Which explains why writing a college essay the night before it’s due is always so much easier…)

Enjoying the process

Stoicism encourages us to “Think progress, not perfection”, to break down obstacles in front of us into small pieces.

“And when you really get it right, even the hardest things become manageable. Because the process is relaxing. Under its influence, we needn’t panic. Even mammoth tasks become just a series of component parts.”



Expecting and preparing for tough times

The only thing we can change is ourselves. The world isn’t going to get easier to live in, work won’t magically become less stressful. Holiday explains, “You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is – at best – indifferent to your existence.”

Holiday pushes us to not only like (or love) tough times – but to expect and prepare for them.

I especially love this section:

“Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel? Because these things will happen to you. No one knows when or how but their appearance is certain. And life will demand an answer. You chose this for yourself, a life of doing things. Now you better be prepared for what it entails.”

^(Repeat to yourself each morning while brushing your teeth).

Flipping the obstacles

Winston Churchill had an acronym he would return to frequently: KBO. Keep Buggering On. (This will probably be my future tattoo).

Loving tough times, expecting tough times, and then pushing through tough times relentlessly takes a special kind of strength.

Holiday says the only way to gain this strength is to practice by doing, building mental muscle.

“Passing one obstacle simply says you’re worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt. Simply flipping the obstacles that life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round.”


It’s not about you

These are all inner tactics and techniques to steal your mind. But sometimes the best way to get out of your own suffering, to get out of your own head and love the struggle, is to think about others.

Holiday encourages us all to step out of our selfish struggles and to understand that someday we will die. Our individual legacy is small. But we have the opportunity to be part of a greater whole, feeling the same feelings, and experiencing the same struggle.

“Embrace this power, this sense of being part of a large whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive, and in the process, inch the world forward a little bit. Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.”

The Stoic Mantra

See things for what they are

Do what we can.

Endure and bear what we must.

What blocked the path now is a path.

What once impeded action advances action.

The Obstacle is the Way.