Season 2 - Episode 17
The Leadership Journey - Season 2
Leadership is a journey, and one that often requires facing change. In this episode, host Seth Dobbs wraps up the season by sharing a personal story from a challenging training hike, using it to illustrate five key leadership lessons.
First, Seth discusses the inevitability of change, comparing it to how trail conditions can shift unexpectedly, requiring leaders to recognize and adapt to new realities rather than ignoring them.
Second, he emphasizes the importance of reassessing your vision and holding true to your values, even when faced with tempting but misaligned opportunities.
Third, Seth highlights that preparation isn’t about perfection but about being ready to adapt, just as hikers must be prepared for unpredictable weather and trail conditions.
Fourth, he notes that clean starts and ends are rare in both hiking and leadership, urging leaders to embrace the complexity of ongoing processes rather than seeking neat conclusions.
Lastly, Seth underscores the essence of leadership as the ability to harness and align the energy of many individuals to create meaningful change, much like coordinating a team on a challenging hike.
These five lessons serve as powerful reminders for leaders to remain flexible, value-driven, and focused on their ultimate goals, no matter what challenges they face.
Audio
Video (with CC)
Transcript
Seth Dobbs (he/him): Do you feel ready to take the next step in your leadership journey? Are you daunted by potential changes that might upset your plans? Are you uncertain what’s next for you? Hi, I’m Seth Dobbs, and this is the Principle Driven Leadership podcast, where I share principles of leadership, along with examples of how to apply them to help make you be the best leader you can be. These principles are based on my years of experience as an executive leader, in building organizations and in coaching others to become leaders themselves. And I believe that not only can anyone develop leadership skills, but that everyone can and should develop leadership skills. I think they’re essential in helping you achieve your best in whatever way you might be trying to make an impact. And that’s because leadership skills help you better influence others to effectively create durable results. And leadership is a journey. I’m going to wrap up this season with more personal stories involving physical and leadership journeys of my own. At the end of season one, I spoke a lot about preparing for and hiking a fourteener, which is an ascent to an elevation of 14,000 feet or higher. This time, I’d like to share a story of one of my training hikes in preparation for that.
Now it was early in the season.
It was late April, which in the Front Range of the Western U.S. means we were in for some snow hiking. Now we expected that and we packed our micro spikes, appropriate layers of clothing and so forth so we could be ready for it.
This was early in our training and so at this stage, our goal was just to go a certain distance and ascend a certain amount of altitude. We weren’t looking to go to a particular height per se, but simply condition our legs to climbing over a distance. Now, as it turns out, there was more than just some snow for the season,
there was actually a ton of snow on the trail and beyond. Or more specifically before we even got to the trail.
We actually had to start our hike about a mile away from the trail head, because snow had made the road to the trail head in passable by car or SUV. So even before we started, there’s already a change in our plans. And once we reach the trail head, it was really an experience because the trail itself wasn’t visible at all. At a guess, we were hiking on around five feet of snow on average. It was actually so deep that at one point , when we did see a sign for the trail, it was not how you would normally see them. They’re typically around my height, but in this case, the sign was barely over the tops of our boots,
just peeking out from the snow. We use a hiking app to guide us on the trails. This is really to help make sure we don’t get lost. Don’t take the wrong fork where there’s a complex network of trails. It also will help us anticipate changes in steepness of the trail and other things. But this time we realized pretty quickly that we were better off walking, where we could see that the snow was solid than to try to follow the actual trail, according to the map and the plan. Because that trail didn’t really exist.
It was below five feet of snow. And trying to follow where it was supposed to be, in some places, would have immediately landed us five deep in snow, if not deeper.
So a lot of this hike was assessing conditions and deciding what we felt was the best way to proceed in the moment. And we met several other hikers along the way that were having similar experiences. And as happens on these trails, we would periodically pass each other depending on different paces, depending on how we each were taking our breaks. And at one point, we actually took each other’s pictures at this really nice outlook over a frozen lake.
And that’s really worth mentioning , because there were a couple of cabins on one side of the lake that you could only see the top story of sticking out of the snow. Now shortly after that rest point, was the final ascent to the summit. It was a fairly steep climb to a ridgeline that was pretty open to the elements and offered little in the way of cover. Now on a normal day that might not have been too bad. On this day. It was actually a lot more challenging.
And so we saw another group that was ahead of us, attempting to make that ascent. We watched as these very fit men and women were trying to scale it. And high winds blew down on them. They’re coming down the mountain side and these hikers hunkered down against it and we could see they were struggling.
So we decided that we clearly were not going to be successful in that ascent. Being lighter weight and not nearly as fit as they were and seeing how much trouble they were having, we realized we just shouldn’t even try. We were a little disappointed and we didn’t really want to turn back and head home yet either. Then we reminded ourselves that our desired outcome for the day, wasn’t about reaching the peak. But rather to condition our legs, our cardio on distance and on the ascent. And so with that, we actually went back down to the bottom of the steepest part that we had already climbed so far and went back up.
And we did that a couple more times so that we in the end reached our goals on distance and on altitude change. And with that goal accomplished, we headed back down to our car, happy with our outing.
That in some ways, very simple hike, captured many lessons about leadership and change. Leadership is a journey. And one that is full of changes, some changes that we can ignore. Some changes that we should adapt to, and some changes that we should instigate. So let’s talk about a few of the observations I made based on that hike and how it relates to leadership.
One change is always occurring and change can range from the very subtle to the very obvious. Now, as hikers, particularly as a mountain hiker, you might see this all the time. Trail conditions can change from day to day. A still morning can turn into high winds or storms in the afternoon; they can sweep down from behind a peak. Snow in the morning can shift to ice as sun and cold hits it at the same time, water can flow and change the trail. Things can even look different when heading up than when you’re heading back down a trail. And the thing is, if you don’t see anything changing, you might not be looking hard enough because there’s always something shifting. We didn’t realize at first that we had left the trail for example, but when we did realize that we were very deliberate about our choices in the face of that change, that we were forced to take a different path. And that’s the thing you can’t address change if you can’t face reality. Once you recognize that things have changed, you can decide to ignore the change, adapt to it, or even instigate a change of your own.
The second lesson is that doggedly following the plan in the face of other evidence can really get you into trouble. If we had stuck to the trail, as marked as designated, we would have been waist deep in snow and potentially in a lot of trouble in a very short amount of time. Now, I’ve talked about concepts related to this in episodes eight and nine of this season, but it’s really worth repeating here since the impact would have been fairly quick and potentially harmful on the trail. And if we had gotten into trouble by following the plan, by sticking to the trail, I can assure you that, trying to further stick with a plan, that is stay on the marked trail, would not have been the way out of it.
So lesson three. Check your vision in the face of change and hold true to your values and the face of tempting, but not well aligned opportunity. When hiking, there’s always a next peak, always the next vista, and it’s always tempting to continue to pursue it; going just a little further, pushing, just a little more. But sometimes doing that takes you on a path that’s rife with danger. And in this case as tempting has getting to the summit was to us, and it was supposed to have a great view, conditions had changed.
And so we re centered on our goals and outcomes and adapted to the change by taking a different path to achieve what we had actually set out to achieve
following a much different path than we had originally planned. So, whether you’re leading a project, a team, a department or company, it’s easy to be distracted by these peaks, the summits, these tempting opportunities. But if those opportunities aren’t aligned with your goals, your vision -if those opportunities present danger and risk, you should think carefully about giving in. And we even briefly considered giving it a shot since we saw some of the others setting out on the path. But again, we realized it wasn’t the right path for us to follow. We didn’t need to follow it to reach our goals.
And this is the case in leadership as well. Just because another team, another leader, another project, another company is attempting something doesn’t mean you should.
So lesson four. Preparing for the journey isn’t about perfection. It’s about adaptation.
I usually don’t know exactly what I’m going to face on any given hike. And so to try and have the perfect plan, especially out in the Front Range, the mountains in Colorado, isn’t realistic because of how rapidly things can change. Instead my co hikers prepare by packing things that are useful and we have techniques to handle different things and different obstacles.
And so we watch the trail and conditions as we progress, looking for signs of change, looking for the unexpected. And then we adapt noting that sometimes we need to slow down, reconsider and even take a different path than we had set out on. Same goes with leadership. You can’t form the perfect detailed plan to take on something new. You need to know what you’re trying to accomplish for sure. And you certainly need to have some notion of how you’re getting there, and you need to scan and be ready to change even with all of that preparation. The leadership principles I provide in these podcasts, as well as your own principles should serve as your tools and techniques for adaptation and adjustment. And your vision, your desired outcomes serve as the guide to help you understand how to adapt when you recognize change and opportunity.
And final lesson number five from this. Clean starts and ends seldom exist in real life.
Even trails, which will often sort of have guides of start and finish, this trail effectively actually started nearly a mile sooner than it would’ve if there was no snow. So immediately all our plans, all our thinking of what constituted to start an end of our journey that day were wrong, wasn’t nearly as clean as a trail guide
might’ve implied, and that’s not unusual in hiking or in life. But it was made really clear by how extreme a difference it was and why it was different.
Now, it makes me think about a while back a friend told me about the coming departure of a leader at her work. And she described it as the beginning of the end, or at least the end of an era. We talked a bit about what that really meant. What factors might already have been in play that led to the person departing. How maybe some of those factors might really have been the beginning of the end. That perhaps some might even see it instead as the end of the beginning of something new. That there were probably multiple events and decisions in play that led to that moment that all could be considered different points of change. And that while we like to see things in a clean way, it’s actually seldom that there are single moments of clear demarcation.
There are always threads and channels, events, and decisions that lead to a moment. So personal note, I read a lot, I mean, a lot. Typically somewhere around 70 plus books a year typically, and most genres, and for what it’s worth, I’m working on reading at least one book from every nation in the world. Now there’s others who watch the equivalent in movies and TV shows and so forth. The thing is,
I think one of the things that makes certain kinds of stories appealing to many of us, regardless of how you consume them, is that they typically have a clean beginning and an end. Now some of the modern fiction I’ve read have neither, and I often really enjoy that for what it’s worth, but it’s nice to see challenges arise, be met and get resolved neatly and cleanly. I think that’s in part because it is so unlike our reality. Now of course, to manage our work and our lives, it’s convenient to create these lines of demarcation. But on the flip side, it’s also useful to understand that whatever is happening as cleanly as we might want to look at it, it all exists in a much larger context.
And seeing the larger context helps bring a more holistic view to your leadership perspective.
Your life, your work, your volunteering, whatever you’re engaging in seldom has clean start and then boundaries, even though you might have a specific start date and an end date. And that’s the thing it’s easier to categorize and process things as if they had these clean starts and ending as if you’re the main character in a story.
And actually you are, you are the main character. In your story. But that means there are billions of stories and billions of main characters in the world, all of which are potential vectors of change to your story. And this is what to me makes the craft of leadership so compelling to think about, to talk about.
And most importantly, to execute. The craft of leadership is about harnessing all of that energy for something more. It’s about aligning many vectors of change, many individual stories together to create something more than any of you could achieve on your own. Whether you’re running a business, leading a team, volunteering, organizing a movement, whatever it might be. Getting the opportunity to create change, to realize a vision, to overcome obstacles in the way and bring others together, at least for a moment in time to create outcomes together, it’s an incredible thing.
Whether you’re changing the lives of a few individuals or billions or anything in between. This is the work of leadership. This is our journey. Thanks so much for joining me this season. Please comment, subscribe, share with a friend if you liked it. Send thoughts and questions to contact@pdlpodcast.com and we’ll address more in a future season.
And join me next season, where I’ll explore more enabling principles to help you continue on your leadership journey.