What Hiking Taught Me About Business

Hiking in the mountains is one of my favorite things. I do it whenever I can.

Over the years I’ve started to notice that the same mistakes show up on the trail that show up in business. When you’re new to hiking, most of your attention goes to the next rock or root. You spend your energy avoiding the obvious dangers right in front of you. You don’t look up much, and when you do, you’ve already missed something.

This weekend I was on a call with a new coaching client and we got to talking about how things go sideways in a business. The hiking parallel came back to me. I made all six of the mistakes below in my early years as an owner. A few of them cost me a lot of money. Here they are.

Mistake #1. Charisma vs. Competence

On a hike, you can hire a guide based on their charisma and end up halfway up the mountain before you realize they don’t know the trail.

The same thing happens when hiring for a business. The candidate is great in the interview. Six months later, you’re cleaning up something they should have been handling.

I hired someone to manage our accounts receivable. A few months in, I found a drawer stuffed with invoices she hadn’t processed. She didn’t know how. About $40,000 was sitting there uncollected. Ouch.

The lesson stuck. Confidence reads well in an interview. Competence is what holds up over time. Reagan said it as “Trust, but verify.”

Mistake #2. Dangerous Assumptions

A hiker sees a clear morning sky and decides it’s a perfect day. They don’t check the full forecast. By noon they’re caught in a storm they could have seen coming.

In my early years, I assumed our excellent service would drive our business. We were known for it. It seemed obvious to me that good service would bring in patients.

Reality was more complicated. Some referral sources cared about service. Others cared about financial incentives from competitors. What I valued wasn’t always what they valued.

If I had checked the full forecast instead of looking at the sky, I would have seen that earlier. Test the assumption before you bet on it.

Mistake #3. The Beaten Path That Isn’t

There’s a kind of climber who believes a well-marked trail always leads to a crowded summit. Entrepreneurs believe their own version: “build it and they will come.” Sometimes a climber reaches the top and finds it deserted. Sometimes an owner launches a product and finds no demand.

I had this happen. One of our better customers gave me strong feedback that pointed toward a specialized service line. I committed. I invested $125,000 and hired two new employees to run it.

We launched. The market’s response was silence. The return was about $10,000. We shut the program down.

It was more than a financial hit. It was a reminder to test the market before committing to it. Climbers scout the route. Owners should scout the demand.

Mistake #4. The Overpacked Backpack

An inexperienced hiker loads their backpack with every piece of gear they own. They believe more equipment means more readiness. The extra weight makes the hike harder.

The business version is what I call feature-itis. You’re trying to build the perfect product, so you keep adding features. The product gets heavier. The buyer gets confused. The thing you were trying to make irresistible becomes harder to want.

I did this with a piece of technology I bought for the business. The advantages seemed obvious to me and to my team. We never paused to ask our customers if they wanted it. They didn’t. The technology became an expensive distraction.

The lesson: light but right. In business as in hiking, what you carry has to earn its weight.

Mistake #5. Vanity Metrics

On the trail, you can follow signs that look authoritative and end up off course. In business, you can chase metrics that look authoritative and end up off course in the same way.

Early on I was focused on growth. I was adding clients. I wasn’t asking whether the clients we were adding were good for the business or whether the cost of serving them exceeded what they paid us.

When I started asking that question, our objectives changed. We retrained the team. We shifted from chasing growth to chasing profitable growth. Like trading a misleading trail marker for a compass and a map.

Mistake #6. Blind Optimism

This was the hardest one for me to overcome.

A careful hiker looks at the path for signs of instability before they trust it. They don’t assume the rocks are solid because they want them to be.

I trusted too easily. I wanted things to work out. I gave people the benefit of the doubt when the signs were already telling me something else.

One of the books that changed this for me was Jim Collins‘ Good to Great. He talks about the Stockdale Paradox, named after Admiral Jim Stockdale, who survived years as a Vietnam War POW.

The paradox has two parts.

Confront the brutal facts. Accept the realities of your situation. Not pessimism. Just facing the truth.

Maintain unwavering faith. Believe you will get through it. No matter what.

Stockdale held both at the same time. He never lost his conviction that he would survive. He also never deceived himself about how bad it was.

I had to learn to hold both. Believe the business would work. Refuse to lie to myself about what wasn’t working.

At the Summit

Hiking and business owe a lot to the same skills. Diligence. Preparation. The willingness to look at the path honestly. The patience to take one step at a time and the discipline to look up often enough to know where you’re going.

I learned each of the six lessons above the hard way. I’m hoping you can learn them an easier way.