That probably isn’t the type of quote that you have grown to expect from my blog. It’s certainly more colorful than what I am used to sharing. However, when I heard Ryan Holiday say that on Ryan Hawk’s podcast, The Learning Leader Show, I knew I was going to have to write about it.

Ryan Holiday is an incredibly interesting cat. He’s the author of multiple books such as Trust Me, I’m Lying: Confessions of a Media Manipulator, Ego is the Enemy, Perennial Seller: The Art of Making and Marketing Work That Lasts, and The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph. I just finished reading The Obstacle is the Way yesterday, and I can tell that it is going to be one of those books that I go back to again and again.

Ryan has been on the Learning Leaders Show three times, and on this particular episode (episode 88), they were discussing The Obstacle is the Way and how to view obstacles as opportunities. He brought up a story that he shares in the book about Amelia Earhart. When she was first approached about being the first female to fly across the Atlantic, she was told that the plane would be piloted by two men, that she would keep the flight log, and that she would be paid considerably less than either of them.

According to Holiday, she didn’t hesitate. She said yes. She didn’t argue about money or about equality, which she absolutely had a right to do. She knew that taking a few small steps back would lead to giant leaps forward in her career…. and it did.

He then jumped into another story about a time when Sheryl Sandberg, the COO of Facebook, was offering unpaid internships, and a lot of people were furious with her. “She’s a billionaire. She can afford to pay (and should pay) her interns.” To this thought, Ryan made a couple of points.

First, an hour of her time is worth A LOT of money. Second, she was offering people the opportunity of a lifetime to learn first-hand from her on a daily basis. The fact that people felt entitled to have her not only give them her advice, but that they also felt entitled to have HER PAY THEM for that opportunity is asinine. When you have the opportunity to sit at the feet of the most successful people in the world in your chosen field, you don’t ask how much they are going to pay you. You seize the opportunity and get it done. Period.

If somebody offers you an amazing opportunity but you are not sure you can do it, say yes – then learn how to do it later!

– Richard Branson

My Story

About two and a half years ago, my wife and I decided it was time to step away from coaching football in order to pursue a position in administration. We had wrestled with that decision for a while, and it had finally become clear to us that it was time to pull the trigger. We knew where we wanted to live, and we knew that administrative jobs in that district were VERY difficult to get.

I sent in my application, and I never heard anything back. This was really hard for me to accept. In a previous school district, I had been offered administrative opportunities, but we weren’t ready to give up football at that particular time. That experience told me that I was qualified, so the fact that I couldn’t even get a pool interview two years later was crushing. I would be lying if I didn’t say that I started doubting myself and my decision to pursue administration at that point.

About three months went by, and I still hadn’t heard anything. I began talking to some friends that I had in that school district, and most of them said the same thing, “If you’re not already an administrator, you don’t have a shot unless you’re in the district. It’s just too competitive.” I don’t think that was necessarily true, but I took it to heart and decided to take a different approach.

Another friend of mine told me about a coaching position that had just opened up in that district. It was a head wrestling job that would not require me to coach football. It was an opportunity to get into the district while still having the time I needed to work on developing the skills necessary to become a successful administrator sometime down the road.

Not one to sit idly on the sidelines and hope that something good would happen, I took action. I went and talked to the athletic director about it, and then I applied for the job. About a week later, I was the new head wrestling coach. I wasn’t really sure what the next step would be, but I at least created some momentum in the right direction.

A year later, I accepted an assistant principal position at the same school.

That seemed pretty easy, right?

Well, there were a few struggles along the way. For example, I had to take a 20% cut in pay when I took that wrestling job. That was a TOUGH pill to swallow considering we had no savings and that we were already living paycheck to paycheck, but here’s the thing. I would do it that same way over and over again. That paycut allowed me to get back into the district that I knew I wanted to be in. It allowed me to move my kids into phenomenal schools. It allowed us to move back into the house that we had built 12 years earlier. It allowed me to become a part of the leadership cadre in the district and share my thoughts/ideas with district leaders. It provided me the opportunity that I needed to prove that I wasn’t “just a coach,” which is most likely what my resume had conveyed to them a year earlier.

When I heard Ryan talking about being willing to “eat sh..” for a while, I immediately thought back to this part of my story. It wasn’t comfortable. We had to make some sacrifices and figure out a way to make it work. It was definitely a “step back” on a number of levels. However, it was that step back that catapulted me into my current role as a school administrator. I am not going to pretend that luck didn’t play a role. I was very fortunate, and there were a lot of dominoes that had to fall perfectly in order for me to end up in my current role. The one thing that I do know is that if I had not turned that obstacle into an opportunity and taken that job as a head wrestling coach, I would not be where I am today. Being willing to “eat sh..” for a little while paid off for me and my family.

What are you willing to do in order to get where you want to be?

Thanks for reading today! If you haven’t read The Obstacle is the Way, I highly recommend it. A good buddy of mine turned me on to Ryan Holiday last year, and it took me a while to finally get to this book. It’s an easy read. It’s actionable, and you can get a lot out of it while reading it in small chunks. Also, if you haven’t listened to that episode of The Learning Leader Show, make time for it. You won’t regret it.

I also want to thank everyone who read my blog last week! It was the biggest week my blog has ever had in terms of number of visitors and number of views. I am fully aware of the fact that it had more to do with Jennifer, Cissy, Becky, and their story than it had to do with my writing. Nonetheless, I am grateful for the opportunity to share their story with the hundreds of people that read it. Hopefully, it will lead to more leaders creating those types of awesome experiences for their people. If you missed it, check it out here.

See you next week!