The Obstacle Is The Way: The Timeless Art of Turning Trails into Triumph

We cannot recommend this book enough to literally everyone! The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph, by Ryan Holiday is packed full of killer stories and timeless quotes that so nicely illustrate powerful directives about self growth and development. Literally our favorite topic here at Market Mamas!

It really is a great straight to the point and impactful book! Author Ryan Holiday draws his inspiration for this book from the concept of stoicism, an ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Already sounds like the tough trader skin we’ve developed right?! Stoics focus on the things they can control, purposefully let go of everything else, and choose to turn every new obstacle into an opportunity to get better and stronger. Holiday shows us how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart — who applied stoicism to overcome difficult or even impossible situations. The way they embraced these principles ultimately mattered more than their natural intelligence, talents, or luck. And the lessons he extracted from their lives and presents to his readers gives us really such a powerful framework that we can apply to our own lives! The way that Holiday presents these points and their impact is very inspiring!

“It’s ok to be discouraged. It’s not ok to quit. To know you want to quit but to plant your feet and keep inching closer until you take the impenetrable fortress you’ve decided to lay siege to in your own life - that’s persistence.”

Check out our full discussion in the podcast below, including more of our favorite quotes and how we’ve adapted the advice into our own trading journeys and lives.

 The gems come at you fast and steadily with this book. Case in point: “When you have a goal, obstacles are actually teaching you how to get where you want to go - carving you a path. ‘The things which hurt.’ Benjamin Franklin wrote, ‘instruct.’” Yes! This is a core element of this whole book! An obstacle may very well hurt, derail and slow you. But, it doesn’t mean you aren’t still on your way and there was a lesson to be learned from that time. Even if you felt pain, choose to see and grow from the instruction that was given to you by that obstacle. And then maybe, the next time you encounter a similar situation, you will respond in a slightly more effective way. And so, growth!

Similarly, “See things for what they are, do what we can, endure and bear what we must. What blocked your path, now is a path, what once impeded action advances action. The obstacle is the way.” This whole concept is just so powerful. How we choose to advance through life is really what our life becomes. Some task or project that was such a struggle for so long can give you that extra push to be more resourceful and strengthen your skillset. And that, in turn, gives birth to a more advanced version of yourself that you needed to become. Another excerpt, at a different place in the book, Holiday said: “Turn every obstacle into an advantage.” People who hold this perspective are our tribe. We can accept the challenge, we can do hard things, we can make a way out of no way. We can do it scared, tired, confused, discouraged, but keep on advancing anyway. Being willing to still show up and do the work even during the least favorable circumstances is our ADVANTAGE! 

 We really appreciated the quote in the book where it says: “Focus on the moment, not the monsters that may or may not be up ahead.” This is how we do best, execute best, make small gains time and time again towards our ultimate goals. Just organized, head down, one task, one trade, one check off the to-do list after another to maximize our time each day and keep us in this headspace. At the end of each day, we can review and plan for the next day. F the monsters that may throw us off track - if that happens, we will deal with it at that time. But until then, we’ve got work to do! Such a powerful and functional way to get things done!

Along those same lines, Holiday also wrote: “Choose not to be harmed - and you won’t feel harmed. Don’t feel harmed - and you haven’t been.” That is awesome because it really reinforces the power we have to extract what serves us the best out of every interaction. If something hurts, say, a losing trade - well, we can sit and feel crappy about the loss and let that negative energy steal the day, or we can take the lessons learned and use it to further our progress by giving us more experience that we needed to be stronger moving forward. Don’t feel harmed and I wasn’t harmed. So much better!!

This next bit is longer but so so spoke to us. It reads: “We’ve all done it. Said: “I am so (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.” This is an important concept to grasp and acknowledge if it is something you are prone to doing, and decide to do better. We have been there. But, those in the moment band aids do not serve or propel us. They pause our growth. Or worse - they can actually feed into a setback of momentum. I think that is a part of maturing. Everyone tuning into Market Mamas is an adult. So, we are mature, right? Well, we all know there are MANY layers to maturity, far beyond just age. And this is an important one. Being able to, in real time, call out our feeding a feeling and pivot that response into more constructive choices. Journaling, talking it out with your partner, a study session over what you need more emphasis on, exercise, a walk, a solid night of deep sleep. These are all much more mature and effective responses to what ails us day to day.  

Holiday similarly put this idea in his book when he said: “In every situation, life is asking us a question, and our actions are the answer.” Right? What we DO is the life we are ultimately living and building. Life will throw us questions, ideas, opportunities, relationships, experiences… What we DO with those is how we are creating our future. We should take that responsibility seriously and make it freaking amazing! With every chance we get. Pedal to the metal energy - Because we are worth the best things. But they are not free. 

This next one is solid and highly relevant! Ryan wrote: “To do great things, we need to be able to endure tragedy and setbacks. We’ve got to love what we do and all that it entails. Good and bad, we have to learn to find joy in every single thing that happens.” This is a big deal. The growth mindset that one needs to have to not only reach your goals, but to enjoy the process is a full time job to cultivate and maintain! So much has been studied and taught about the power of living in the now. I love the saying, “Don’t let the future steal from your present”. It’s hard, especially when you're hard at work to change the future. We are not guaranteed that time will come that we are hoping to impact, or even tomorrow. We are actively pushing towards so many life-changing goals, but also want to always live each day to the fullest and enjoy who and what is around us now. Even on our heavy lesson days, we are still amazing and deserve to be celebrated, these are the moments of our life and they are a blessing. Recognizing that joy each day with gratitude grants us the ability to endure the setbacks and wait on the greener days that are always closer than they feel! This energy field is one we try with all our intention to uphold and transfer to others. 

 Let’s talk failure for a minute. Holiday wrote: “Failure shows us the way - by showing us what isn’t the way.” This is such a great statement! It’s another way of saying what we always say - take the lessons from every failure. When we try something, say a trade based on a level and a setup we are working to master. And the trade fails and we take a loss. Was that a loss on every front? Hell no. It was a lesson to show us the flaws in that plan so that we can learn and find the right trade for that setup for next time. The failed outcome was just feedback that will guide us if we look at it for what it showed us and not with negative energy. We are far from perfect with this, but love this energy so much and try very hard to improve with this outlook every day!

This next sentiment in the book says, “Nothing stands in my way. Everything guides me along my way.” This is the spirit to have to lead us on our paths to greatness. Things are happening for us. People, places, and things are being orchestrated on our behalf to serve us in my purpose. There is evidence all around us when we are on the right track, when we are open to see it, and that can really help us gain clarity, confirmation, and momentum by acknowledging that! 

This podcast episode is full of these and many more great reminders for us all, so please check it out in it’s entirety. This advice is truly timeless and highly relevant to any massive goal getter!

The Obstacle It They Way has a 4.7 star rating on audible!
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