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Writer's pictureCraig Whitton

Sunday Story: The Leadership Road Trip Series Finale - Take Care of Yourself First!

Welcome back to the fifth and final instalment of our Leadership Road Trip Series. Throughout this series, we’ve shared lessons learned from our tiny-space adventures to the most remote areas in the world. We’ve talked about the importance of choosing your team, how critical it is to spend time organizing your processes and systems, and why you shouldn’t fear getting stuck - it’s part of the fun. Last week we wrote about how leaders need a lot less than they think, and this week we’re back with the most important lesson of all: Take care of yourself first.


This is a leadership lesson that you’ve probably read and said “That’s nothing new” and that’s true. Leaders have been talking about the importance of self-care since I started my career nearly 20 years ago.


And leaders are still really bad at self care, so even if it’s nothing new I’m still going to write about it today.


But, let’s keep the theme alive here and tell you a little story that illustrates how important this is. Recognizing there’s been a lot written on this topic, there are two specific examples that this article will focus on.



A cat sitting in a camp chair.
After 5 articles, proof that we do indeed bring our cat camping.

The first specific example is one that I know a lot of leaders fall into: the Fake Break. Stay with me here and see if this sounds like you: A Leader takes a day off work so that instead of sending emails and making decisions in the office all day, they can escape to that nice mountain cabin or beachside resort so that they can…send emails and make decisions from there instead? I’m not just talking about the occasional response to an email on vacation - we all do some of that. I’m talking about leaders who pretend to take a break but never actually disengage from the thing they are working on.


I’m not talking about burnout here - though that can definitely be a part of this conversation and we’ll talk more about it later. I’m talking about leaders who already know how to balance their lives and work within their capacity with good boundaries, and often because they are so good at this balance, they feel they can always maintain that tether to their leadership responsibilities (and they can). However, severing that tether temporarily has all kinds of benefits - when we take a step away from something we often come back with fresh eyes and new perspectives that take it to the next level, but it’s amazing how rarely leaders in this example take this time.


I would definitely be in this category, but our adventures make it impossible - being off grid and away from cell phone reception means that work problems can’t bother us, even if I really wanted them to. We do have emergency communications via satellite, but if you thought it was frustrating to make a decision when someone in the office has a slow Zoom connection, imagine what it’s like trying to do meetings via 140-charachter limited text message with 20-30 minute delays in sending. It’s enough communication to have peace of mind, but not enough to truly meaningfully engage in my 9-5 work, so it forces me to disengage from my work and truly step back.


The other huge benefit to truly setting down your leadership responsibilities is that it allows you to see how many fingers you have in the dam of your organization. Remember that classic cartoon trope, where the dam springs a leak and the character on screen sticks their finger in the hole to stop the water flow, and then usually a moment later another hole appears, then another, and the character is forced to respond in a panic to keep the water at bay? Lots of leaders are in that position and they don’t even realize it. Taking a step away allows you to see where your systems might be failing you (the dam breaking) so that you can proactively enhance those systems instead of waiting for catastrophe. More importantly, it allows those you lead to step up and flex their own leadership chops - they’ll never be able to do that if your leadership is always only an email, teams call, or text message away.


The second element I wanted to talk about is about the aforementioned burnout: leaders tend to care deeply about those they serve in their leadership, but one of my favourite sayings is that “you cannot sustainably keep others warm by setting yourself on fire”, and if you are doing everything you can but those you lead are still struggling “light yourself more on fire” is rarely the right answer. Often though, leaders fall into that trap - again, I’m one of them - where we forgo essential self-care because of a felt sense of obligations and responsibilities. Leadership roles tend to attract people who have a tough time letting those obligations and responsibilities fall by the wayside. But if a leader is struggling in their leadership too much, that’s exactly what they should do - just like when we are on an adventure, sometimes it’s the moments we choose to not make progress that are the most important.


A man and a small child sitting next to a fire, the child is warming his hands by the fire.
Teaching him essential camping skills, like how to warm hands near a fire.

There are so many of our adventures where taking a break made the difference between a good story or a tragic outcome; it’s hard to pick one, so we’ll talk about a general theme instead. As we discussed in part 3, we’re no strangers to getting stuck. The first thing we do when we get stuck is to grab our traction boards - sticking them under the wheels is an easy solution that works 80% of the time, which means most of the time that’s all we need to do and we’re back on our way. But about 20% of the time, that doesn’t work right away. The next best step is always this: turn off the car, make a cup of tea, and drink it.

This second step might take only 10 minutes, but in that 10 minutes we’ve done a lot. First, we’ve gotten some calories in us. Thinking on an empty stomach is never effective, and the emotional resiliency required to fix a problem is always greater with managed blood sugar. Second, we are giving ourselves a bit of time to sit with the challenge at hand. In this time, we’re likely to notice things like big rocks, trees, or better approaches that later serve our recovery. And finally, it allows us to reset - when we got stuck, we probably had a goal like “let’s get up the hill” or “let’s find that campsite”; if we don’t intentionally take a break and reset, that goal remains - and that means getting the car out is a barrier to the goal. In this situation, we are likely to feel time pressure will be related to the goal - the setting sun, a hungry toddler, etc. - and that time pressure might make us try to take shortcuts in our vehicle recovery. Shortcuts in this situation can often result in people getting really badly hurt or killed.


But by taking a break, we’re actually changing what the goal is, and sometimes Leaders need to do that too, especially if they are struggling. By disengaging entirely on the problem of the stuck vehicle, and instead focusing on the problem of making a cup of tea, we’re focusing our minds on something entirely unrelated to the problem at hand. And, when we finally finish the tea and put our focus back on the car, the problem isn’t about the campsite or the hill anymore. It’s about getting the car out.


When leaders are at max capacity, feeling burned out because things aren’t going right, a lot of them will tend to think that working harder is the solution - and sometimes that may be true - but often this is an indication that taking a step away is what is needed. As a leader, putting down your leadership responsibilities - not for long, even just for a weekend - can be the same as making a cup of tea in the middle of a muddy mess. It allows you to disconnect and return with fresh eyes, a fresh perspective and probably fresh solutions.



a family of three with a dog sleeping in a tent smiling at the camera.
Happy adventuring (and leading!) from our family to yours!

There’s so many more lessons we have learned from adventuring out of our tiny truck and living in our tiny home, and we may do a second series in the future, but this concludes the 2024 edition of the Leadership Road Trip Series. Thanks for reading, and we’ll see you next Sunday with a brand new topic to help you reflect on your leadership and thrive during disruption.

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