Leadership on the Edge: 7 Lessons From a Dangerous Mountain

For 20 years, I swore I’d never climb New Hampshire’s Mount Washington. A woman I’d admired in college named Cheryl had died hiking down it one early spring. Her curly brown hair, warm heart, and bright smile left a lasting impression on many. The university held a large memorial; her death stayed with me.

Though I’d hiked many nearby peaks since, I avoided Mount Washington like the plague. But seven years ago, logistics—and a helpful Appalachian Mountain Club staffer—led me to book a stay at Lakes of the Clouds Hut, just 1.5 miles from the summit. I went solo, in honor of Cheryl. At the top, a woman asked to photograph me, sweaty with my heavy pack and trekking poles, to inspire her adult daughter. That moment felt like a link in a chain: from Cheryl to me to this woman and her daughter. Courage, passed forward.

Five years later, I hiked the same 20-mile trail solo in reverse. Both trips were hard, with mud, steep drop-offs, dense fog, and long stretches of solitude, but also filled with breathtaking views and deep reflection. These hikes built confidence and strength.

Still, I had one unfulfilled dream: learning to mountaineer. I’d known about a mountaineering school in North Conway, NH since college. More than 30 years later, just after my own child left for college, I signed up. The location of their introductory course? Mount Washington.

I couldn’t take the course in deep winter, so I booked for mid-March—the same time of year Cheryl had died. A work conflict meant it would be a private, weekday course: just me and my guide, Katie.

On our first day, I told Katie Cheryl’s story. She encouraged me to dedicate the climb to her. The next morning, I said a quiet prayer of gratitude, thought about Cheryl and what she had meant in my life, and started up the mountain, ice axe in hand.

The first 1,500 feet went surprisingly well. We camped near the Harvard Cabin at 3,500 feet. That night, fierce winds woke me. We’d known 45–75 mph winds were forecast, and I assumed we’d scrap the summit attempt.

At 5:30 a.m., I asked Katie what she thought. “This is normal weather here,” she said. “Skies are clear. Let’s go.” Surprised, but trusting her, I agreed.

We ate oatmeal, packed our gear, and started hiking, headlamps reflecting on the snow. Soon, we broke tree line to a brilliant sunrise, with a view of low clouds in the valley and lush green undulating mountains as far as the eye could see. Snow gave way to exposed boulders. The wind picked up. Despite poles and ice axe, I struggled to stay upright.

I yelled to Katie, “I’m scared! Is this safe? It seems like it’s only going to get worse as we get higher, and I’m worried it might not be smart to go ahead.” She was only a few steps ahead of me, but couldn’t communicate over the howling wind, so she returned to my side and replied, “I’ve done this every week for three years. This is normal. Why are you questioning my judgment?”

“I’m not,” I said. “I’m just really scared. It feels like it’s going to get worse.”

“If you want to go down, we can,” she said. “But this is a good day. No sleet, no rain. The sun is shining.”

So I followed her up.

The wind worsened. We pressed on to Lion Head, a rocky outcrop 1,000 feet below the summit. In the wind-sheltered crook of the rocks, we ate protein bars and took photos.

Katie asked if I was ready to continue. I said yes. But as we stepped around the protective rocks, a gust knocked me sideways. I got up, and we tried again. Same result.

As we regrouped, Katie asked me if I wanted to try to walk around the corner one more time. I thought about it, and while I didn’t want to do anything life-endangering, I was also curious, and I didn’t want to turn around and go down the mountain without being sure that it was impossible to continue. I said yes. We walked around the corner again. And again, I immediately got knocked down by the wind.

Leaning against the large rock I’d been pegged to, I knew Katie wouldn’t be able to hear me over the whipping wind, so I motioned with my hand cuttinghorizontally across my neck to signal to her, “I’m done. Let’s turn around now.” She gestured for me to wait. Moments later, she returned. “I checked ahead. It’s not safe to continue to the summit. The winds are too fierce.”

Disappointment, relief, anger, and hurt flooded me. I was disappointed but also relieved to turn back, and frustrated I hadn’t trusted myself sooner. I’d felt accused of doubting her expertise.

We descended through calmer winds, rappelled icy slopes, and returned to the car safely.

As with all difficult experiences, I looked for lessons—especially ones I could share. Here are seven leadership insights I took from the mountain:

1. Trust your gut—even when an expert says otherwise.
When I heard the howling wind that night, my instincts told me we wouldn’t climb. But I didn’t ask Katie about her decision-making process—I simply deferred. Later, when I felt unsafe, I asked, “Do you think it’s safe?” instead of saying, “I want to stop.” Upon returning home, a seasoned guide told me: forecasts of 50+ mph winds often mean a trip should be canceled or altered. I hadn’t known that figure, but my gut did. Trusting your instincts doesn’t mean disrespecting expertise—it means giving equal weight to your own.

2. Your body has a built-in early warning system. Use it.
Between the forecast, my fear, and the ability to think ahead, I sensed danger early. Yet I dismissed my fear, recalling advice like “FEAR = False Evidence Appearing Real.” For years, I’d internalized the idea that emotions are barriers to overcome on the path to achievement. But emotions, data, and foresight combined are powerful. Listen and use them; there’s wisdom in them.

3. Know your values.
As the wind howled, two values clarified my choice: healthy living and love for my family. Pushing ahead would have violated both. Clarity beforehand helped me decide in the moment.

4. Know your purpose.
My original purposes were to learn to mountaineer and enjoy nature. Summitting may have become an implicit goal as we’d started to ascend, and my guide may have assumed it, but it had never been my original purpose. That became clearer only when I had to choose between pushing forward or turning back. Define your purpose before starting a task—it’ll guide you when things get tough, and help you make better, faster decisions.

5. Match the type of experience to the situation.
Katie had the technical experience I needed—for example, to get up the ice. But I had more life experience. Experience comes in all forms: technical, specific to a particular project, and life experience that tends to be correlated with age. Great teams—and great decisions—depend on discerning which types of experience are most relevant when.

6. Communicate future-oriented concerns in ways that land.
Katie was present-oriented. I’m future-oriented. I used data and intuition to forecast trouble. She focused on now, confident she’d adapt later. This difference in our orientations to life made it easy for her to misread my concern as criticism. If you’re future-oriented and trying to influence others, speak in terms that will make sense to them. Perhaps add a qualifier like, “I know it might sound crazy…” or “It’s hard for me to explain it rationally…” or some other cue that what you’re saying is not about them, it’s about what you (intuitively) know.

7. Most decisions aren’t life-or-death.
Getting knocked down at Lion Head reminded me: some decisions are life-or-death. But most aren’t. We treat many decisions—change jobs, move cities, hire someone new—like they’ll make or break us. But they rarely do. When I was 22, trying to choose between living in two different cities, my first therapist said, “You have two good options. Either one could work. Choose one and commit.” That’s still good advice.

As a leader, you’re constantly making decisions—some high-stakes, others routine. The next time you face a crossroads, ask yourself:

• What are my emotions signaling to me (even if I’m not sure why I’m feeling them)?
• What are my values and purposes for the task at hand?
• What type of experience is most relevant here?
• How can I best communicate my perspective in a way that others can hear it?
• Is this a life-or-death situation? Or does it only feel that way?

Then pause to listen, not just to the experts around you, but to the wisdom within.