Like life, climbing to the top of Diamond Head requires perseverance

“It’s not the mountain that we conquer, but ourselves.” – Sir Edmund Hillary 

I was recently on vacation on the island of Oahu in Hawaii. As one who enjoys the outdoors, Hawaii is a paradise. In addition to exploring a cave, hiking to numerouswaterfalls, and lighthouses, I also made the notorious climb to the top of Diamond Head. 

In my younger years, this would not have been one of the harder climbs that I have taken. But at my age now, it was more of a challenge than I expected. On top of that, I was fighting a bad head cold and congestion. Our reservation time for the hike was in the middle of the afternoon, so with the heat added to the mix, I had my work cut out for me. 

For those unfamiliar with the Diamond Head hike, you make your climb on a paved trail that eventually turns into switchbacks on the ascent to the top. The final section is a steep set of stairs that takes you to the summit. 

A few times on the climb, I was offered the sympathetic, “It’s okay if you want to go back down and not do it,” knowing that my breathing was difficult at times. But I was determined to reach the summit. I certainly didn’t set any records for the best time getting there, but I got there. And it was worth it! 

The climb to the top reminded me of a few important leadership lessons I benefited from. Perhaps they will speak to you as well.  

Great views come after great challenges 

The views from the peak of Diamond Head are breathtaking. The view was worth every step, every stop, every pause to catch my breath, and every opportunity given to turn back. 

Significant impact and making a difference come not by taking the easy path, but by taking the hard ones. Some decisions you make are hard, some conversations are difficult, and at times your perseverance will be tested. It comes with the territory. But you will never experience the reward of the summit view if you give up. It’swhen you embrace the challenge that you get the reward of the view from the top. 

Getting to the top will be hard 

I chose to hike to the top of Diamond Head not because it was hard, but because of what I knew awaited me when I got there. 

I could have been discouraged by little kids outpacing me, the heat, or the fact that the climb exposed the uncomfortable truth that I am no longer in the athletic shape of my youth.  

In leadership, distractions are a constant companion. We have to prioritize our day, make important decisions, and not get distracted from keeping our eyes on the mission before us. In other words, the struggle is real. And sometimes the obstacles and struggles appear larger than they truly are.  

As I made the climb, I kept reminding myself it would all be worth it. I had to tune out the distractions around me and press on. Once I was at the top enjoying the view, the struggles were out of mind. 

We are better together 

At the summit, the view is spectacular. But another part worth noting is the encouragement hikers gave each other along the way, and the celebrations with families and friends, taking pictures together at the top.  

Leadership is not about reaching the top alone. Successful leaders help and encourage one another and go out of their way to create a culture where everyone reaches the top. It’s not a competition; it’s a shared journey where leaders want to see everyone win. 

It’s been said that a true leader measures success not by how high they climb, but by how many people they bring with them.  
Diamond Head reminded me that leadership is, in many ways, a climb. It can be hard and steep, and not everyone will want to make it with you. But when you persevere, you will enjoy a view unlike any other. 

Learn more at dougdickerson.net/ or email Doug at Dougdickersonleadership@gmail.com. ©2026 Doug Dickerson