“The future in flux always is.” ~ Yoda

Alert: This is a longer than usual post.

Last June I wrote about my son Dave’s thru-hike of the Appalachian Trail – 2,200 miles from Springer Mountain, GA to Mount Katahdin, ME. At the time, he was just about a third of the way into his trek. I’ve posted a link to that post at the bottom of the page.

In early October he completed the AT. Camille and I met him and his girlfriend in Millinocket, Maine, at the end of the trail, and brought them back to our house in southern Maine.

Dave spent the next week with us decompressing (his girlfriend had to get back to Washington, DC for work). From mid-March until early October, he had spent most of his time on the AT. He needed time to prepare for re-entry back into “civilization.” He got to sleep in a bed every night, shower every day, eat real food – food with a life cycle – and interact again with people, traffic, and technology.

Hike Your Own Hike

Needless to say, he had a lot of stories to tell – about continuously changing weather as he moved north from Georgia at the end of winter; to Tennessee, North Carolina and Virginia in mid-summer; to New England as autumn approached; and the need to adapt to often-sudden changes. He talked about the terrain and how the two states at the end of the AT – New Hampshire and Maine – were the most difficult; and his mileage dipped from 15 and 17 miles a day, to 1 mile in three hours.

He talked about other hikers – of all ages – he met along the way. And he talked about “trail magic,” where people known as “trail angels” provided food, lodging, and transport to grateful hikers.

He talked about the differences among day hikers, section hikers, and thru-hikers; and how he learned not to personalize it when the former maneuvered upwind away from him and his thru-hiking buddies. And he learned to appreciate the AT adage: “Hike your own hike,” which meant one didn’t get engaged in others’ issues or drama along the trail.


After a few days though, his talk shifted to the future. The near future – the very near future. He started talking about where he was going to live back in DC, getting a job, getting his car back on the road, and the next steps in his life.

Dave had undertaken the AT thru-hike in large part because he was trying to figure out what he wanted to do next. He had been a case manager for a social services agency that provided transitional housing for chronically homeless families. While he enjoyed much of the work – especially with the youth – he quickly tired of the bureaucratic issues he had to deal with. And he knew he’d have to start thinking about grad school if he wanted to continue to do the work he wanted with young people. So after 18 frustrating months, he quit and literally hit the trail.

Unlike the apostle Paul on the road to Damascus, there was no big epiphany. He didn’t appear at the foot of Mount Katahdin with all the answers to the rest of his life. He did, however, have some firm beliefs on lifestyle choices and an awareness of what he didn’t want to do.

Career Design Thinking

(You knew I’d tie all this to careers.)

My friend Erik recently turned me on to a podcast “Getting Unstuck” (link at the bottom of the page), which talked about the use of design thinking in problem-solving. Basically, it pondered the question “how do you build something when you don’t know what to build?”

This question is really relevant to folks who find their way to me for coaching. So many people begin our conversation with “I just don’t know what I want to be when I grow up.” These are folks in their 20s, their 40s, and even late 50s to mid-60s. They’re all searching for the perfect career.

The podcast discussion distinguished between tame problems you know how to solve, and wicked problems, unstable problems with changing criteria that require inconsistent solutions. It talked about wayfinding,” getting comfortable with the idea of multiple destinations, where there may be more than one right answer, vs. navigating, where there’s a clear path to resolution.

While Dave navigated the AT – following a relatively pre-determined path – he was confronted with wicked problems – what worked on one part of the trail, didn’t necessarily work farther along. Planning a career would be different…a lot different. In that case, he – and most of us – will be wayfinding through wicked problems.

Design thinking is one way to work in these circumstances. The heart of design thinking is looking hard at your circumstances for room to maneuver. Always taking action on the problems you’re confronted with; adjusting and moving forward. No one can know the future, we design it as we go along. It’s life and careers in beta. And we keep doing it indefinitely.

There’s no one ideal job for us. The best we can do is to find out what we need to consider for the next 2 to 5 years. We should develop alternative scenarios and prototypes that address the actual problem we’re trying to solve at the time.

And we do this throughout our careers.

Over to You

So, as always, over to you. Can you apply the aspects of design thinking to your career? What problems and issues do you need to consider for the next 5 years? Are they tame problems or wicked problems? Can you develop prototypes for their resolution?

Here are the links I mentioned earlier:

My earlier post about Dave’s on the AT: Resilience.

The “Getting Unstuck” podcast from Hidden Brain.


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