The Obstacle Is The Way

The most important book I’ve ever read is The Obstacle Is The Way

Speaking in absolutes is one of my least favorite things. It’s something I try not to do in my own life, and it can cause me cringe-worthy feelings when other people do it. Here’s what I mean when I’m referring to speaking in absolutes: You launch a website for your new business, and on launch day, when you’ve built excitement and buzz leading up, your site is completely down. You think or say, “This is the worst day ever!”

Nope. That day is most certainly not “the worst day ever.”

I get it. Most people don’t actually mean it when they speak in absolutes. But it’s something that drives me nuts because absolutes stretch the reality of the situation. Things aren’t usually as cut and dry and people make them out to be, and absolutes make us lose perspective on what’s actually happening.

That said, I can unequivocally state with absolute fact that the most important book I’ve ever read is Ryan Holiday’s The Obstacle Is the Way.

This book, unlike any in the Harry Potter series (ahh, who am I kidding—I haven’t read more than a handful of pages in any of those books), has changed my life. The Obstacle Is the Way has made me a better person. And it has definitely made me a better business owner.

The obstacle is the way

The premise of this most important book I’ve ever read is stoicism

Google tells me the definition of this word: The endurance of pain or hardship without a display of feelings and without complaint.

I want to be clear that I haven’t become an emotionless robot because I read this book. Holiday walks you through stories of stoicism as they relate to business owners, the über-successful, and war heroes—they weren’t emotionless robots, either. And I didn’t have interest in becoming more like any of the people in the book as much as I wanted to overcome a big obstacle in my life that was holding me back: Thinking of my IWearYourShirt business as a failure.

When you do something for five years and pour your heart, soul, and nearly every waking hour into it, it’s not an easy thing to detach from. It becomes especially more difficult to detach from the negative thoughts and memories. After hanging up my final t-shirt in 2013, a dark cloud hovered over any thought or discussion involving IWearYourShirt. Sure, the business had generated over $1,200,000 during its 5-year tenure, but I didn’t have any of that money left; in fact, I was over $100,000 in debt (which we got out of last year!). I didn’t even like to bring up money in conversations about IWearYourShirt because I felt such shame about the financial situation I (and really, the business) had gotten into. This was the obstacle that I wanted to find my way over.

About a third of the way through the book, I started to see the light. I could begin to understand that having this unfortunate ending to the story of IWearYourShirt was not what defined the business, idea, and five years of my life. That ending was simply a stepping stone. Sure, it was a stepping stone that stepped on ME at times, leaving me hurt and stressed out.

But it wasn’t the final stepping stone. In fact, it was actually a very important piece of my entrepreneurial journey. In Ryan’s words:

“Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves.”

And here’s another quote that hit me at exactly the right place and time:

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

Why the obstacle IS the way

When an obstacle hits, it’s like standing at the foot of Mount Everest. How will we climb this insurmountable obstacle? How will we navigate all the unknown parts? How will we survive if Games of Thrones ever comes to an end???

For me, and for my IWearYourShirt business, I realized something that completely shifted my outlook on the ill-fated closing of that shirt wearing business: The shutting of IWearYourShirt opened doors to new ideas. The longer IWearYourShirt stayed open, the longer I’d have to wait to pursue other things.

Now, was I brimming with ideas? Was my brain overflowing with concepts and dreams I couldn’t wait to try out? Not really. On the contrary. IWearYourShirt, and the downturn of it, actually zapped me of most of my creative thoughts and aspirations. What started as an endless supply of creativity in 2009 ended in 2013 with what felt like nowhere to turn.

I thought the only option was to continue to iterate (insert industry buzzword bingo: pivot) my IWearYourShirt business again and again until something hit. And while that actually could have been a possibility, to land on another direction for that business, the more time I spent holding onto it, the more time I wasted allowing other possibilities to show up in my life. A big part of me was just ready to move on and challenge my brain to come up with another idea like IWearYourShirt. Could I could up with another truly original/unique/different idea? Or was I a one-hit wonder?

Finishing The Obstacle Is The Way gave me new perspective on what has happened for me between 2013 and now. And while it wasn’t an overnight shift in that perspective, it was actually much quicker than I thought. Sure, I was also having many-a-DM (deep and meaningful) conversation with my life partner, Caroline. That helped as well. But as we all know, even the people closest to us can give us the best advice, but when the advice comes from a credible outside source, like a book, we take it and are much quicker to accept it. What this book helped me learn to do was repeat these things to myself:

  • IWearYourShirt was not a complete failure.
  • You, Jason, are not a complete failure.
  • You, Jason, are not just IWearYourShirt.
  • You, Jason, can come up with more ideas and will go on to do other things.
  • You, Jason, could always just get a job at Target or Starbucks, and figure out a way to get by in life.
  • You, Jason, could always move home, suck it up for a bit, and remember that nothing is permanent.
  • You, Jason, need to stop talking to yourself in third person. It’s freaking people out.

How it made me a better person

It sounds silly, but Ryan’s book gave me the permission I needed to be more accepting of myself and the mistakes I’ve made. More importantly, it also gave me story after story and example after example of people who had screwed up WAY worse than I had and made huge comebacks from it.

Unfortunately, I have to drop another absolute on you. Ugh, I’m such a rule-breaker of my own rules. Writing my first book, Creativity For Sale, was the most cathartic thing I’ve done. With the help of my amazing book editor, Lizzie, I was able to let go of a lot of mental baggage. The reason that book got written and the subsequent catharsis happened was that IWearYourShirt failed. Had it kept going, I would have kept going. I would not have gone through the exercise of writing a book and hosting my own personal mental gymnastics.

The obstacle of shutting down IWearYourShirt was the stepping stone to writing a book. And writing a book opened me up as a person. That allowed me to move on and let go of a bunch of stuff I was holding inside. While IWearYourShirt was one big stepping stone towards writing my first book, it’s all the stories about building IWearYourShirt that were the tiny stepping stones that advanced me further and further across the river that is life.

How it made me a better entrepreneur

A year prior to shutting down IWearYourShirt, I had another obstacle get in the way. My mom went through a divorce, and it left me (and her!) with a last name we no longer wanted. This obstacle, having a last name that didn’t define who I wanted to be, sparked the idea for my BuyMyLastName project: a crazy idea to auction off my last name to the highest bidder in a 30-day auction. That project (I did two auctions in two years) netted me nearly $100,000. I was able to creatively overcome an obstacle in my life, make money from it, and also donate a sizable portion of that money to charitable organizations.

Selling my last name and writing my book were the stepping stones to leaving IWYS behind and believing I had more to offer the world. I began to believe I could come up with other unique ideas and they wouldn’t all end like IWYS did. So I set out to create my first online course in 2013, I searched high and low and couldn’t find a course platform that suited my needs. Everything was either too bloated with features, too difficult to set up, or worst of all, forced me to have a website plugin or house my course within a branded platform. This was my course-creation obstacle. I knew I could create the content. I knew I could sell the course. The obstacle was finding a platform that was technology agnostic (meaning: wasn’t forced into an existing ecosystem) and that would be easy to use over and over again. Stumbling into that obstacle was what led to the creation of Teachery, an online course platform I co-own with my friend Gerlando Piro. That initial obstacle has gone on to create a side business for me that pays my bills and provides an incredibly easy-to-use course creation platform for anyone in the world (at a very affordable monthly price, I might add).

I can look at every situation I’ve been in and every business I’ve created, even before IWearYourShirt, and clearly see an obstacle that led to the beginning of each business. Some problem. Some issue. Some event that needed to be overcome.

What obstacle is standing in your way?

You, most likely, are staring an obstacle in the face right now. It may not be one as insurmountable as standing at the foot of Mount Everest (I think we’re both thankful for that!) But I’m guessing something has happened in your life or business that you feel you can’t get past. Something that’s holding you back and keeping you from moving forward to the next stepping stone.

How can you change your perspective your obstacles?

Your website went down on launch day?

Truly a bummer. I’ve been there (many times). Can you use it as a teaching moment for anyone who looks up to you for inspiration? Can you use it as a moment to reward your loyal customers and extend some offer to them that wouldn’t have existed? Can you learn from the experience if you have the right customers for your business (ones that don’t scurry like roaches when the lights get turned on at the sight of any problems with your business)?

You end a long-term relationship?

Also truly a bummer and one I’ve experienced, too. Does this open the doors for you to find someone who is better suited for the person you’ve become? Does this allow your former partner to do the same thing (find someone they are a better match for)? Does it create the opportunity for both of you to live happier and healthier lives?

You close down a business that isn’t doing well?

I don’t even think I need to say much else here. Won’t closing down this business open the doors of opportunity that have been closed? (The answer is yes, and I can obviously attest to that.)

Obstacles suck. They are not fun.

They are not ice cream cones covered in fudge and sprinkles. They are plates of boiled chicken and broccoli. They are the difficult decisions we must make in our lives. They are the important decisions hiding behind awful events and circumstances. When you’re in the middle of dealing with an obstacle, it will feel like climbing Mount Everest. And even though you and I will probably never know that exact feeling, we can sure as hell take a wild guess at how difficult it would be.

Like climbing Everest, you overcome obstacles step by step (or stepping stone by stepping stone). You put one foot in front of the other. You swing your pickaxe into the next piece of frozen mountain, and you move forward. Eventually you reach whatever summit of your version of Mount Everest that will make the difference for you. Then, you get to look back on it. You get to see your life and all the new opportunities in front of you with more clarity, because you’ve overcome a difficult obstacle.

There will always be more obstacles.

But as Holiday talks about in his book, and as stoicism teaches, if you can endure the pain and hardship, and see it for exactly that, you can take a step back and not let it affect you. With every new obstacle that comes your way, you have the reflection of previously overcome obstacles to guide you. To have you take a deep breath. To have you take a step back. To have you realize today isn’t “the worst day ever.”