One Person's Heaven Is Another Person's Hell: Leading Every Type of Hiker

This article is adapted from Ted's Smart Thinking podcast Episode 394: when Your Heaven is Someone Else's Hell: Leading through Divergent Minds.

“I don’t understand why they want us to do this.” “I don’t know how anyone thinks this is a good idea.” “What is wrong with people?”

Sound familiar? I hear stem sentences like these all the time, and lately I keep answering them with the same phrase: One person’s heaven is another person’s hell.

What brings me joy might be your torture. The thing I’d happily do all day might bring you great misery, and vice versa. Put me in a room full of optimistic problem solvers and I’m energized. For someone else, that’s exhausting. Meanwhile, a room full of people bonding over complaints about workloads and other people’s ideas? That’s somebody’s heaven, too. Misery loves company.

This gap matters, especially as we head into winter. It’s a big reason so many initiatives launched in July die around Thanksgiving, and why the ones launched in January fade right before Mother’s Day. Some people have the will and the skill. Others have a little of each, or neither. And somehow, we still have to come together to meet our mission and support others.

Three National Parks and One Crowded Trail

This past summer, my family took a multiple thousand mile driving loop from Wisconsin to three national parks. We hiked the Badlands (pro tip: July in the Badlands is a bad idea, which is probably why they call it that). We spent a week in Glacier National Park. And on the way home, I had what my kids called a “fever dream” touring my favorite president’s new presidential library, then watching herds of buffalo roam Theodore Roosevelt National Park ten minutes later.

In Glacier, we picked a hike all four of us could do: Avalanche Lake. About four miles round trip, roughly 700 feet of elevation gain, through an ancient cedar forest along a creek, ending at a crystal clear lake framed by cliffs and towering waterfalls. A must, everyone said.

What we didn’t plan for was the Fourth of July crowd. When we pulled into the parking lot, I got a feeling in my stomach. My heaven was creeping toward my hell. I said, “This is going to be tough.” My son said, “Get over it. It’s going to be beautiful.” My wife handed me her massive water bottle to carry, and off we went.

The Four Types of People on Every Trail

When you spend a lot of time outdoors, you start to recognize people. On that trail, we saw all four of my mental categories, over and over:

• The Naturalists. Experienced, prepared, and they know the rules. Like the couple in their 80s hiking this trail on July 5th for the 50th year in a row, laughing and stopping to admire things they’d seen dozens of times.
• The Enthusiasts. They’ve prepared in some way, but they’ve never done this before. Like the four college guys hauling pizzas up the mountain, hoping they’d still be hot at the top.
• The Wannabes. Big energy, little preparation. Think dress shoes, Crocs, and flip flops on a trail that always turns into roots and rocks. They start strong and peter out well before the end.
• The Hostages. They clearly don’t want to be there. You can see it in their shoulders, their head, their walk. They carry a cloud above them and let everyone know it.

Anyone can be any one of these, at any age and at any level of a family or an organization. And as the trail got more crowded, with people littering, yelling, and parking themselves in the middle of the path, I could feel my patience dropping. It felt like Costco on a Saturday.

That’s when my wife leaned in and said, “Teddy, one person’s heaven is another person’s hell.” The message was clear: turn down the judgy attitude and be empathetic about what they’re experiencing.

The Kid with the Bear Spray

A little farther up, I saw a teenager twirling a can of bear spray like a cowboy with a pistol. On a packed trail. Nobody was paying attention, and I felt an obligation. (My family, of course, immediately sped away from me.)

Picture this: bright orange trail runners, a big red backpack with patches and a Snoopy keychain, bear spray and a compass on my chest straps, and the unmistakable aura of a dad and school teacher in his mid fifties. I walked up and asked, “Do you know what’s in that can?”

He smiled and said, politely, “Not a clue, bruh.”

I explained that if it went off, he and everyone around him would share a burning feeling none of us had ever experienced, and his nose would run for a month. His mom, a naturalist, smiled and said she’d told him that a hundred times. Then he handed her the can and said, “I don’t want this. I don’t want to be here. I just want to go back to the cabin.”

He was a hostage.

His mom told me they were at a family reunion with more than 70 people staying at one campground for ten days, and everyone had decided to hike together. It was contentious. Parents, kids, grandparents, aunts, and uncles were all frustrated. When I said, “One person’s heaven is another person’s hell,” she said, “They’re making my heaven hell. I want a t-shirt that says that.”

Then she asked what I’d do with 75 people. My answer: I wouldn’t make them all do the same thing. I’d offer ten choices and let people pick.

The Destination Changes Everything

When I finally caught up with my family, we’d broken away from the crowd. We could hear the creek. We were unified in the beauty, the shared experience, and the fact that we were together. Then we rounded a bend and saw the pebble beach of Avalanche Lake, the immense cliffs, and the waterfalls rushing down. It was surreal.

We sat on a log for over an hour. I ate my peanut butter and jelly sandwich with a Granny Smith apple while friendly chipmunks climbed onto my foot for sunflower seeds. And I watched almost every person we’d passed arrive, and watched their conflict and frustration wash away.

That’s when it hit me. This heavenly spot was a hell of a journey for many of them. For me, the heaven was the journey, the company, and the destination. For them, only the destination was heaven. But we all shared the same view.

Matching Skill and Will

So what do we do when our heaven, our expectations, or our mission is someone else’s hell? We name what’s happening, claim responsibility, and address it together. One tool I love is Max Landsberg’s skill/will matrix. The idea is simple: effective leadership isn’t treating everyone the same. It’s matching your approach to each person’s readiness and motivation.

• Naturalists (high skill, high will): Delegate. Give them space to lead segments of the trail, but coach them not to run ahead of the group.
• Enthusiasts (moderate skill, high will): Coach. Help them turn preparation into real world experience without overwhelming them.
• Wannabes (low skill, high will): Direct. Create guardrails, short term milestones, training, and lots of positive reinforcement so their energy doesn’t turn into early burnout.
• Hostages (variable skill, low will): Restore agency. Listen with empathy, show them where they have choice and voice, and co-create as much as possible.

How to Lead Each Group Forward

If you’re a naturalist leader, slow down. I know this one personally. I can walk into a room, get everyone fired up, walk out, and come back two hours later to faces wondering how in the world they’re going to do this. Drop to the middle of the pack, where the terrain gets tough for others. And replace obnoxious optimism with validation. Constantly saying “It’s going to be fine” becomes toxic positivity. Try instead: “This is demanding and the terrain is steep, but here’s why it matters and how we’ll navigate it together.”

Bridge theory to practice for enthusiasts. Think of the new assistant principal with the degree, the energy, and some wonky situations ahead. Give them ownership of low risk, high visibility projects. Debrief at key waypoints: What worked? What didn’t? What did you learn?

Build scaffolding for wannabes. Break long deliverables into small checkpoints so they don’t burn all their energy on day one. Pair them with naturalists or enthusiasts who can mentor them when their energy dips.

Give hostages real choices. Ask, “What conditions would make this worth your effort?” Give them authentic responsibility within their strengths, like risk management, quality control, or process review. They don’t always have to run the whole marathon. Maybe they work the water table. Maybe they keep time. Keep offering options within their skills to grow their will.

And here’s the hard part. If someone continues to work against everyone, call it out. Not all the kids get to go on the field trip. A behavior ignored is a behavior reinforced. Hostages aren’t truly held against their will. They act as if they are. Sometimes the kindest thing is to set them free to find success on a different project or somewhere else.

Just don’t hear that anyone who disagrees with you is on a forced march. Include dissenting ideas. Validate real concerns and solve them together. Celebrate big hurdles, share lessons learned, and fail fast. People find engagement when they have choice, agency, and recognition for their effort.

My Heaven, Her Hell

Let me leave you with one of my hells. I’m drawn to activity like a moth to light. My absolute hell is being idle with nothing to do. And yet I’m in love with an amazing woman whose heaven couldn’t be more different.

During the school year, her Friday night heaven is a big blanket on the couch, feet up, gradebook open, papers everywhere, and a Hallmark movie or an old episode of Friends on TV. Her hell? An overstimulated husband named Ted walking in wanting to do anything else.

Do I have the skill to sit still? Questionable. The will? Not really. But I have determination and commitment. So in winter, I light a fire, pop in my AirPods, grab a book, and get up every four minutes to move the logs around and work off my energy. She’s in heaven because I’m there with her. Summer brings her along on my hikes. The school year anchors me to the couch.

Relationships, and teams, aren’t just about compromise. They’re about empathy and putting others’ needs above our own, not once in a while, but most of the while.

Let’s Do Some Smart Thinking

1. Describe something you view as heavenly that others see as hellish.
2. Which of the four profiles describes your best behavior on a journey with other people?
3. List the people you support. Are they naturalists, enthusiasts, wannabes, or hostages? How will you lead each one differently?

Your altitude is determined by your attitude. Whether the journey is a real mountain or a quiet night on the couch, it’s up to us to find the skills, the will, and the determination to help everyone around us succeed. That’s a storm worth running into, and a trail worth navigating.

Want to go deeper? Pick up my book, Go to Your Storm, at CESA6.org. A facilitated book study guide and lessons for teaching it in schools are coming soon.