My son and I hiking Mt. Rainier in summer 2019.


We All Struggle.

A few years back, my oldest son, Santino, was skiing for the first time with me. He was 7 at the time. We had enrolled him in lessons, and he was learning the fundamentals. Then it was time to get on the chair with Dad and have some real fun!

When we loaded onto the chair lift, we high-fived and he told me excitedly, “Dad, I’m going to be better than Uncle Morgan!” He’d heard countless stories of his uncle heli-skiing in Alaska and made it clear to me that he wants to be the best. We high-fived again and I told him another Uncle Morgan story to fuel his ambition.

We skied a few of the lower runs and were having a blast. “Dad, I want to do the blue runs! Let’s do Golden Nugget and Alpine!” he exclaimed. He had no clue what these runs were aside from the stories I shared about the mountain. He just knew they were bigger and faster than the runs he’d just been on. “Heck yeah! Let’s go!” I said to him. We skied to a different chair and he beamed with excitement.

He wiped out several times on the new runs, but kept dusting off the snow. We laughed them off! I could see the mountain humbling him as we knocked out a few more runs, but he kept going. Before long, his confidence rose, and he believed he could tackle a black diamond run. I hugged him and said we needed to save that first black run for Mom. I told him that Mom is a better skier than Dad and he’ll need some really good tips from her so he can get as good as Uncle Morgan.


Every Struggle Teaches Us Something–The Gift

I learned to ski the hard way when I was 18 (my first time). My brothers thought it would be fun to put me on the chair lift, take me to the top, and watch me roll all the way down. It was fun…for them. Fortunately, I still thought I was invincible, and refused to give them the satisfaction of quitting. It was a very long day.

Although painful, I learned to ski quickly. I was in a hurry to get better. But my fundamentals were weak, and my improvement was forced as they overwhelmed me with instructions.

I had a similar struggle when I started my leadership journey. The first ten years were a lot like that first run: skiing fast, awkwardly, and downhill. My struggle was very much like my son’s ambition to ski. I wanted to do more, but felt like I had very little control over my ability.

I had yet to learn the lesson I share in Chapter 10 of The Gift of Struggle: more is not the answer. Like many aspiring leaders, my ambition was running faster than my ability to develop myself. I was trying to take everything in, but nothing was sticking.


Leadership is Sharing Those Gifts

When my son and I reached the top of his first blue run, the first thing we did was plan our route to the bottom. I had him follow me down and was very encouraging on the way. He was still in full control and I skied close, so he felt safe. My skiing guided him where to go, what to avoid, where to turn, and what lay ahead.

But I only coached him on one thing every run. The more I focused on less instruction-giving, the better he got.

Students of struggle do the same—they apply what they are learning to their strengths over some periods of discomfort. Compare this to the rush of doing as much as possible over a short period. They have figured out that the long way is the shortcut.

Flash forward two ski seasons; my son is doing the black runs and is also learning to do jumps on the way down. He consistently flirts with the boundaries of his ability….and his mom’s sanity! He now leads me down the runs he was dreaming about on that first chair. Look out Uncle Morgan!


Become a Student of Struggle

Aspiring leaders tend to over-complicate the steps they need to take to become the 2.0 version of the leader they are today.

Ask yourself the following to get started:

  1. What fundamental skill do I need to learn to become a better leader?
  2. What’s the next big step for me with this skill?
  3. Who’s a great guide or expert that I can learn from?

Pick one thing for every “run” you make and give it all your energy over a longer period.

Leaders that transform themselves know the key is to focus your energy on fewer concurrent improvements, giving more effort to each item. The fewer you work on at once, the more energy you have to pour into each. More is not the answer.

Hail the Underdogs!


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