Knowing when to quit

Nature is a great guide in knowing when to quit. It's not always as obvious in business settings.

Back below 5,000 feet

It sounded simple enough. Hike up the flank of Mt. Hood for an early season easy overnight, 20 miles out and back, to get some milage and elevation gain in, and test out our gear. My friend was preparing for the Wonderland loop around Mt. Rainier, and I was happy to be her training partner what with my own Timberline loop and Eagle Cap Wilderness adventures coming up.

Fun fact: we hadn’t seen each other in 10+ years, but were familiar with each other’s hiking and backpacking skills through a mutual friend. So off we went, using the drive to the trailhead to get reacquainted, and set off on a rainy June day. Nothing unusual in that, it’s Oregon, after all 🤣. Catching up on kids, careers and outdoor adventures made the time fly by, and before you know it we were trekking up the mountain at a good clip. We’d easily make our designated camping designation, and were well matched in pace and attitude.

We hadn’t done any kind of hiking or adventuring together, and it might be a testament to how women in their 50s communicate with each other, but we arrived at the same conclusion at roughly the same time. About 3 miles into our trip we started encountering more rain and snow than the forecast had led us to expect, and the waterproofing on our hiking boots began to fail. Next thing you know we were breaking trail in about a foot of snow, and heading into whiteout conditions at about 6,000 feet. It became apparent that any of the overnight camping spots we had planned for would all be above the snow line we were encountering, and likely on the windward side of what was quickly becoming an unpleasant late spring storm.

So we huddled and decided we had learned enough about our equipment, had nothing to prove to anyone, and turned around. We took the picture above once we had dropped well below the snow line again—behold all the bear grass! And then retraced our steps back to the trailhead. 1,800 feet elevation gain over 6 miles, 17,0000 steps and 2,400 calories is a good weekend outing, and we were pleased to discover, in talking to some hikers at an alternate trailhead that the creek we avoided crossing was indeed running high and fast. We stopped at an awesome BBQ place on the way back to town, defrosted our toes, and congratulated ourselves on our wisdom.

We mildly wondered about the dude we met on our way down, whose Weimaraner was shivering when we stopped to chat. Hopefully he turned around not long after us, but 🤷‍♀️.

All this to say, Nature has a really obvious way of letting you know when it’s time to quit, or pivot, and you literally risk your life when you ignore her call.

On this adventure, we might have persevered if getting from Point A to Point B was somehow mission critical, but it wasn’t. We were just there for a limited test of our endurance and equipment, and it was easy to say, “OK, that’s good enough, let’s turn around and adjust.” We had a lovely time getting warmed up and chowing down on a BBQ meal at a delightful place on the way home.

Now translate that to what you might be encountering in your work environment.

Just recently, a friend exited a toxic business environment where a charismatic founder was not able to maintain the minimal requirements of sound business practices and governance. It was hard on my friend, who is passionate about the industry and has a lot of experience and wisdom to offer, just not at the cost of her integrity.

Another friend was abruptly laid off from a global humanitarian aid organization, a victim of both the ruthless defunding of US international aid under the Trump regime and a board of directors that’s skewing transactional in an industry that’s fundamentally relational.

In both cases, my friends were both not surprised and a little caught off guard by the pivots required for their integrity and mental health. Both of them talked about the unease they were experiencing over some period of time before quitting, and a creeping sense of misalignment with their respective boards and bosses, before their working relationship became untenable.

My adventure buddy and I were practicing a form of expedition mindset that's applicable to the challenges that my other friends were facing, as well as to leadership under uncertainty more generally. Is your team, your board, your staff ready to follow you around the mountain? Are you ready to take them there? Is it safe? Are you prepared to deal with sudden changes in the weather? I’ll more to say on what I mean by an expeditionary approach to leadership in a future post, but in the meantime here is a LinkedIn article that does an adequate job outlining some of what I am sensing into.

Knowing when to quit a particular pursuit or a leadership role is one of the hardest things to do, and there is no right or wrong way to do it. My June hiking adventure exemplifies the thought process for figuring out when it’s time to quit, but here it is as a short recipe: