Surviving the Cotswold Way: The Tough Mudder of Leadership Challenges

I've championed long walks for leaders for years, have taken them myself and received glowing reports from those who did the same. This one, the one I just survived - yes, survived - was different. I kept thinking of the Sesame Street song: One of these things is not like the others.

Taking long walks is good for you, no question. They can be inspiring, invigorating and useful because in most cases, on day three, my life automatically properly reprioritizes itself. It was time for another physical, mental and spiritual re-boot. My friend, Jan, wanted to go with me.

The Cotswold Way seemed a good choice. A website describes it thus:

Almost the entire trail runs through the Cotswolds Area of Outstanding Natural Beauty and passes through a succession of enchanting English villages, featuring traditional Cotswold cottages and welcoming country pubs. Cross fields bounded by hedges and stone walls as the trail twists and turns through undulating and stunning landscapes. You will enjoy expansive views, stumble across Neolithic sites and be surprised by elegant village churches.

What's not to like? A company specializing in self-guided walking holidays promised handpicked accommodations and baggage transfers, so all Jan and I had to carry each day were our lunches, which would be provided each morning, our hiking poles, and a detailed guidebook. Signposts with acorns would point the way. We chose the 10-day version, which would have us walking between 8-13 miles a day.

I broke in my new boots by walking two miles on my treadmill each morning. When Jan and I met at the Seattle airport, we were ready, excited.

I've been home for a week now and during my recovery, it occurred to me that our journey seems a useful analogy between what a leader's expectations are and what he/she may encounter. The fantasy versus the reality, if you will.

CW Fantasy: After a good night's sleep in a cozy B&B, we would study our route for the day over coffee and breakfast, be handed our lunches, put on our boots, grab our sticks and set off.

CW Reality: When there is a prevalent smell of mildew in a stately but ancient home and your host's Jack Russell has regularly peed on a corner of your bed for the last eight years, it is hard to get a good night's sleep. These would have been tolerable if I could have had my morning coffee with cream. I don't smoke, rarely drink and don't do drugs, not even those that are legal in Washington. I do require coffee with cream. The English drink tea with milk, not cream. At a B&B, if you ask for cream for your coffee, your host will appear stunned, as if you'd requested a bit of roasted badger with your eggs. One rather severe host replied, "Cream is not allowed in this house!" But you're good with clotted cream on your scones and butter on your sandwiches, I wanted to point out. And didn't.

CW Fantasy: We would step out of the B&B onto a well-marked path each morning and spend the day enjoying "expansive" views, fill our lungs with sweet-smelling air, and stop on a peak for lunch. And of course, there would be signposts.

CW Reality: There weren't always signposts. Some had fallen to the ground and pointed nowhere. Some were confusing, like this one.


Some posts were absent altogether, and when two roads diverged in a yellow wood, we sometimes made the wrong choice, which made all the difference. On day three we walked 15 1/2 miles, as opposed to the 11 we were supposed to walk. Another wrong choice put us on this path.


That is mud and cow dung. I slipped and fell in it. When Jan tried to help me up, she fell on top of me. We should have taken a selfie.

CW Fantasy: I would make myself available to any messages the universe might send me. I'd listen to birds and bleating sheep and anticipated the green growth my mind would take from hills and pastures. I hoped the sun and wind would tell me what to do.

CW Reality: Pheasant shooting season began on day four and the playlist for the next few days was gunshot, which drowned out bleating sheep and the wind. You engage different muscles when you flinch and duck. My thoughts were not lofty. No insights, no clarity about my life. My thoughts were more along the lines of - How come my phone says we've walked five miles when it feels like 10? How many poor pheasants are being slaughtered? Why would anybody put butter on a ham and cheese sandwich? And arriving at another incredibly steep path - You've got to be kidding! Haven't the English heard of switchbacks? On day 4 my priorities did shift. Making it to a pub became #1. Speaking of pubs...

CW - Fantasy: Our daily reward would be arriving in a picturesque village each afternoon, in time for a wander, a meal in a pub called The Red Lion, The White Hart, The Black Swan, The Drunken Duck, or The Cat & the Custard Pot, then stroll to our nearby, cozy B&B.

CW - Reality: While a few of our B&B's were in picturesque villages with at least one excellent pub, most were near the path, quite a distance from a village or a pub. To get to a pub, we'd need to call a taxi. And another to return us to our B&B. On two nights, we were too tired to go anywhere.

CW Fantasy: The views will be worth it.

CW Reality: To get to "expansive views", we had to climb. Yes, "the trail twists and turns through undulating and stunning landscapes" but two miles on a slightly elevated treadmill at home did not even begin to prepare me for 10-13 miles ascending and descending seriously steep paths that required planting my hiking pole at every step. I recalled the last lines of Beckett's novel, The Unnamable, in which a character says.

I can't go on.
I'll go on.

It became our joke, our mantra.
Me: "I can't go on."
Jan: "I'll go on."

CW - Fantasy: I'd lose a few pounds.

CW - Reality: I didn't. Seriously unfair and how is that even possible?!

Let's consider leading, the fantasy and the reality of leadership.

Leadership - Fantasy: When you launch a company or take on a leadership role it's essential to have a clear and compelling picture of where you want to go. Robust work, global clients eager to provide case studies proving the value of what it is that you do, happy employees who demonstrate high levels of collaboration, accountability and a bias toward action. You will, of course, give others the credit for success, while savoring the satisfaction that your work, your ideas, your vision have come so fully to life. And you will be well compensated.

Leading - Reality: In reality, leadership demands everything you've got and a whole lot that you don't "got", so you have to go out and find it. Leading doesn't always show immediate signs of success. It's only when you make the effort each day, when you're tired and frustrated and somewhat lost in the complexity of your role, that good may later come of it

In my second book, Fierce Leadership, a memo to leaders begins:

"Congratulations. You are a leader. It's a heavy load but someone has to do it. The primary focus of your organization is growth. To help in this regard, it is your duty to lead change, manage and motivate a multi-generational workforce and execute initiatives that impact the top line and the bottom line while delivering short-term results. You must demonstrate agility, speed, inclusiveness, strategic acumen and innovation, manage uncertainty and risk and mitigate the impacts of globalization, off-shoring, a recession, global warming and the price of oil, etc., etc., etc.

Some time ago, the beloved founders who kept balance between order and chaos cashed out, either by dying or cashing in their chips. Since then, Forces of Darkness have been vying for the top spot. You are all that stands between them and the destruction of the collective organizational soul. If you fail, Darkness will cover the earth, the stock value will plummet and Chaos will reign."

Leadership - Reality:

You won't always get a good night's sleep.

You will encounter mud and worse.
There aren't always signposts.
You will take wrong turns.
You will have to climb many steep hills.
You won't always get a good night's sleep.

Even one toxic employee can soil your culture.
Some will take pot shots at you.
And as Simon Sinek points out, leaders eat last. Unless you're the CEO of a bank, golden parachute in hand, those who choose leadership sometimes find that they make less money than they did as an individual contributor.

But at times, the view will be glorious, worth every bad night of sleep or extra, unexpected effort to get there.

In spite of the challenges, I wouldn't take anything for my 10 days on the Cotswold Way and for the privilege of leadership. Leadership is not meant to be a straight path with few or no obstacles.

Perhaps leadership is a long walk, an extended conversation with yourself, your employees, your customers and the unknown future unfolding around you, not knowing what's over the next hill or what you will encounter each day, an exercise in orienteering, moving from point to point in diverse and unfamiliar terrain, often at speed and at times, sans map and compass.

If you've chosen leadership for the right reasons, if for example you intend to champion the common good over narrow self interest, though at times your thought may be: I can't go on. You'll go on.