Getting Lost and Found

In 2016, my wife and I got lost backpacking in the Rockies. Unless you count a few modest camping trips, we were "lightly experienced" in mountain backpacking, despite some bucks dropped at REI.

It was also September, which bring swift changes in weather. Experienced hikers will have the long list of factors (read risks) that come with hiking especially at elevation, starting with getting lost, getting hurt, freezing to death, running out of water…you're in the wild and off the grid, so knowing what you’re doing is sort of a pre-req for not dying.

I made two critical mistakes (along with 22 minor ones) that put us in danger.  The first critical mistake was getting off the marked trail.  We ended up on what appeared to be “a trail” but not the one we intended to take. There are thousands of trails in the Rockies - hiking trails, animal trails, old logging and mining paths, etc. and guess what, it’s important for survival to know the difference! 

The second and much more dangerous mistake was that for the next 5 hours, I proceeded to interpret “signs” as indicators we were “on the right trail” (A baseball hat, an empty soda can...) as we ascended up past 12,000ft. I was bending reality to fit my plan. We were getting higher in elevation, further from our destination and weaker in the legs thanks to our weighty backpacks. My delusion finally broke when I looked behind me after a particularly strenuous ascent and could not even identify a path from where we had just come; we were waaaaay lost.  

“Reality is that which, when you stop believing in it, doesn’t go away.”

- Phillip K. Dick

After getting home, I picked up a great book (Deep Survival) that discussed why some people survive being lost and others do not. It lists among the causes of bad outcomes, my “bending reality” mistake and its role in whether someone survives. (I also later took a Wilderness First Responder (WFR) training class, but that’s another post with an even more humbling lesson.  And yes, the irony of doing both these things AFTER the hiking trip is not lost on me). 

In the book (Deep Survival), there are powerful parallels to startup life. It turns out that it’s quite common to mis-interpret cues from the work environment when it does not match our mental models.  You only have to ask a sales rep what they think about their pipeline to get an example of how common it is to confuse “wanting something to happen” with “what is really happening.”

At work, we all want things to go well. I’ve been susceptible to finding evidence that things were going well, even when there was contradictory evidence suggesting otherwise; apparently my mind wasn’t willing to see that alternative. As it turns out, losing objectivity is quite easy as we pursue our passions.  

After being “lost” enough times at work, I realized I needed the most objective sources I could find to navigate a clearer path. This became most obvious when I led sales teams into unfamiliar or new parts of the market for growth - we had to find the truth quickly.

Who should I believe regarding our product market fit in these unfamiliar markets?  How could I quickly determine what the reality was?  After deploying sales and marketing resources over the past four startups, here is my  prioritized list of sources, and some suggestions on how to better stay on the trail.

A few suggestions here: 

1. Take care not to hire out research to people who want to “smooth out” the insights coming from the market. You should be looking for the “unvarnished” truth, even “scary” truth, not a pat on the back and a refined marketing message.

2. Focus intently on better understanding the problems that people in your market have, how they have been dealing with them and what makes dealing with them challenging. Notice that this does not include introducing your solution; you are not focused on that yet as you want a clear and current picture of the problems.

3. Keep learning. A couple of helpful resources for asking good questions are:

The Mom Test.   A great, short read on asking non-leading questions every professional should have integrated into their practice. 

Deep Survival.  About why people survive (or don’t) when getting lost outdoors.   Also a great parallel to work, a guide when we get lost indoors. 

As my wife and I scrambled back down an unknown “path,” I was more concerned than I wanted to admit; I had no idea what side of the mountain we had come up so as we descended, I knew we could quite easily end up miles from our trailhead.  By sheer luck, we eventually ran right into the exact trail (and a hiker, who knew what she was doing, confirmed it).  

I was spent by both the exertion and the worry, and suggested we head back to the car. My wife wanted to head back UP the trail to the lake to camp. We compromised and headed back UP the trail to the lake to camp.  

Mother Nature doesn’t care how prepared you are and at 2am that night she flexed, with temperatures dropping to the mid-40s followed by torrential rains and winds pounding our small tent. Wide awake in the dark, I worried about the rainfly getting ripped off the tent or 12 inches of snow falling, leaving us wet, cold, alone and with no bad-weather gear. But the rainfly held; another lucky break.

I love having learned (and not suffered too much), both in the woods and in work.  So yes, I’ll keep trying.

“I am always ready to learn although I do not always like being taught”

- Winston Churchill