Trip Planning as Strategy

Vocabulary and communication are key.

I once brewed five gallons of a basic pale ale and then hopped each one-gallon batch with a different hop variety, hitting each all the old school additions: bittering, flavor, aroma. It was a fun exercise to get to know each variety. I had a friend over to taste them and, quite the opposite of my mediocre vocabulary, he would smell and taste each and immediately say what the flavor was. “Black Magic Marker.” That was one of them, for Magnum, if I recall correctly. There is no way I would have ever said that, but once he did I got it. He was absolutely correct.

Vocabulary, and the ability to community using that vocabulary, are key in high stakes situations.

In the spring of 2024, I enrolled in Luc Mehl’s Start and End at Home course. I have always been a detailed—very detailed—planner, putting together big planning documents for trips. The course added to my thinking about the planning process, which I appreciated, but where I believe it really shined for me was in the discussion of risk.

I’ve studied risk from an academic perspective, I’ve modeled it in a professional setting, and I’ve read about it in the context of survival and disaster psychology. I am very much familiar with the academic and practical application of risk management. Despite that experience, the course enhanced my grasp and application of risk communication: internally monitoring it and externally communicating it. I developed the habit of monitoring and communicating risk tolerance, and with that term I have adopted two meanings: one is discrete and the other cumulative. Exposed cliff? That’s a discrete case of, “yes, I’m good,” or, “no, let’s go another way.” Personally, I’m going to avoid that and other kinds of exposure. However, there are countless other risk exposures on a longer adventure, and over time I believe those exposures can add up, along with other stressors (lack of sleep, high calorie expenditure, reduced calorie consumption, etc.), resulting in a cumulative risk load.

I used to only think about risk tolerance in the discrete sense. I now think about it cumulatively, as well, and it has become a tool for making good decisions in the wilderness.

How does this apply to planning and strategy? I will write another time about the detailed planning process I use for adventures, but for now the important point is that it includes route development, which involves looking at ridges and valleys, rivers and glaciers, tree lines and boulder fields. When I develop ideas for a route, I know what makes for good—fast, safe, low risk—travel. I do a lot of research to support the process and, in the end, ideally I will have come up with a good route option or two that will limit exposure to discrete risks as well as attempt to lower the cumulative risk load. That’s the plan and the start of the strategy.

When I’m out in the environment, I continue to take in data, connect actual conditions to what my planning had shown me, and make adjustments to the route. During an adventure in 2025, what had looked to be a good route during planning was quickly dismissed when we laid our eyes on the massive peak with a boulder field from head to toe, across which we had originally planned to traverse. Nope! That led us to make a tactical decision. We pored over the maps and developed another route. (I reached—and communicated—my cumulative risk tolerance limit on the alternative route, but that is for another story!)

Strategy is so much more than just risk, but this article is focused on that side of a plan: how you plan for, think about, and make course corrections to adjust for risk. Project risk management plans talk of workarounds, contingency plans, risk tolerance of the different stakeholders, and the like. However, risk can present itself differently as you go from textbook to the field. It’s worth it in advance to have those frank conversations about how much risk tolerance you—your team, your company—have in the face of life/company-ending consequences.

What are the turnaround conditions, the situations in which you’re not willing to accept the risk and will shift to plan B? What is the acceptable exposure you’re willing to face, whether that’s a deep water crossing or a potential major financial loss? Where do we stand with very low probability but very high consequence risks? How many high probability, low consequence risks can we tolerate cumulatively? What will we do if—when—things go wrong?