You're Too Old to Think You Can't Still Make Mistakes: a Lesson from Cheryl Strayed's "Wild"
Too Old for This Sh*t: How to Take Your Life Back
Why Strayed is still one of my sheroes because of her mistakes
Why this tale remains one of my faves, and why Strayed’s lessons resonate for all of us.
Sierra leaned back in her chair.
“She was a moron,” she said with some venom. “I can’t believe she was so stupid. Totally unprepared.”
“I agree,” said Terri, sitting next to her. “How could anyone be so dumb?”
We were discussing the book Wild, which tells the story of a young woman’s trek up the Pacific Crest Trail (PCT). Cheryl Strayed, the author, recounts her rookie mistakes, and what she learned along the way while hiking one of American’s toughest through-routes.
I was watching the members of the book club excoriate Strayed’s inept preparation for her enormous undertaking. The dumb stuff she bought. Her incredibly overstuffed backpack. Mistake after rookie mistake.
These were members of the Outdoor Women’s Alliance, a growing online community of women who love the outdoors and represent a lot of talent in a broad range of outdoor activities. Experienced backpackers, climbers, hikers women. All thirty-plus years younger than I am.
All of whom, like Strayed, were also once total rookies. Like we all are just starting out.
Strayed’s book (as well as the subsequent movie from December 2014 starring Reese Witherspoon) has inspired thousands more people to attempt the PCT, many without any more preparation (or less) that Strayed had invested, and many with much the same results.
Many don’t get far at all.

Was Strayed so stupid?
Oh, I can give you stupid. I can give you unprepared. As a 70-year-old adventure traveler, I heard these women’s remarks in the context of someone who had done much the same or worse than Strayed.
The parts of Wild that made me hoot the hardest were those that reminded me of the same kinds of mistakes I’d made in 1983 when I had decided to walk the entire coast of Australia by myself. Of such hubris, stupidity and monumental lack of reality checks, great adventures are made.
Or, you die.
In 1983, I was laid off from what was then Martin Marietta Aerospace. Armed with a handful of cash for my trouble, and with a free promotional trip via United Mileage Plus to Australia, New Zealand and Fiji, I told all my corporate buddies that I was going to throw a backpack on my back and hike around the entire country. Um, YAH.
Like many others I had no clue how big the “entire country” of Australia actually was. Such claims are greeted with deep amusement by Aussies who work in the consulate, and who receive inquiries like mine.
I was ridiculous, full of the confidence of the clueless.
At REI, like Strayed, I bought one of everything. One prime example was a tiny device the size of a quarter which lit up from behind with the push of a button. It displayed maps.
The only problem was that the only maps it displayed were for Yellowstone National Park, which isn’t particularly handy when trekking the South Island of New Zealand.
Clueless.
If I could have packed the kitchen sink, I’d have found a way. I did, in fact, have a folding portable sink which trekked with me four years and untold miles without seeing a drop of water.
I had 35 pounds of “this might come in handy at some point.” Most of it never did.
By the time I finished, my backpack weighed nearly eighty pounds. I had no idea what would happen when I started walking. Especially uphill. Especially in the Rockies, where I lived, and was bound and determined to do a pre-trip practice run.
In September of 1983, I planned a weekend in the high country to test out all my fancy new gear, including a tiny telescoping fishing rod, candle lanterns to keep my tent lit at night. I drove to the base of St. Mary’s Glacier, west of Denver, and parked. It took me several minutes of struggling to get that pack on my back.
My knees sagged and my back shrieked.

I simply wasn’t prepared for that weight at that altitude. Each step was an agony of effort. So when I reached a green spot by the side of the road and noticed wild raspberries growing in abundance, I figured this was perfect excuse to rest, while picking a few for my evening’s dessert.
I had been walking for all of fifteen minutes.
Because it had taken so much effort to get my pack on in the first place, I decided not to remove it. But I had to have those juicy, ripe berries.
The second I leaned over to start picking, the weight of my pack whipped me over and downhill. I began sliding uncontrollably down the same steep incline I’d just climbed. I grasped crazily for anything to halt my slide, picking up speed, until I slammed to a molar-jarring stop against a big boulder.
I was on my back, legs and arms waving in the air like an upended turtle. Red-faced and cursing, I struggled to right myself. I couldn’t.
As I lay there in the bright September sunshine, the brilliant blue skies overhead, I was more worried about making an ass out of myself than anything else.
I was stopped on a hairpin turn. The corner boulder had prevented me from sailing over the edge of the clay road out into space, with nothing to stop me for a long ride down.
It took a while to lug the bag to a properly-sized rock, then wrestle it to the top, then get that leviathan on my aching spine.
I’d barely been gone two hours from the house. I was already filthy, exhausted, and ready to go home.
But I didn’t.
Berries picked, the pack secured, now covered with clay dust, I continued my hike upwards.
By the time I made it to my campsite, which was next to a lively trout stream, it was damned near nighttime. When you’re at treeline in the Rockies, especially past August, it gets terrifyingly cold terrifyingly fast.
In no time my one-man Marmot tent was set up, the candle lanterns lit, and I was eyeballing my Yellowstone National Park maps in my sleeping bag.
I’d had five hot chocolates right after dinner, so barely an hour later, I woke up with a full bladder. The candle lanterns had barely cooled. My feet were freezing. I sat up, knocking the lanterns in all directions.
Somehow I’d broken the two-way zipper on my down bag. Not only did I have to find a way to repair it but I also had to get outside to pee. As I thrashed around in my tent trying to find my flashlight, my head repeatedly hit the candle lanterns.
Finally I located my torch, unzipped the tent and padded around in my stocking feet to find a suitable spot.
And stepped right in the freezing cold water of the stream.
Now I can’t speak for anyone else. I already suffer from cold hands and feet, but stepping into the snow-fed waters of a high altitude stream will startle the hell out of anyone. Especially when you’re trying to find your way around in the dark.
In the woods. Above treeline. Freezing cold. And alone.
Now I had freezing feet, a broken zipper, and I had to find a repair kit in a hurry. Desperation did the job.
When I finally finished my repairs, I settled back into my sleeping bag after changing my socks, my feet still freezing , and eventually drifted off to sleep.
The next morning, I woke up to the sweet sussuration of winds in the high pines. I sat up and ran my hands through my long hair.
Or tried. I encountered solid masses of hardened wax, the result of having repeatedly collided with the still-warm candle lanterns.
After I made myself a breakfast of oatmeal and eggs, I spent three hours removing my candle wax helmet along with a considerable handful of hair.

At midday, I tried out the brand-new telescoping fish rod. I baited the hook and set it in the stream. Trout curved quietly in the eddies.
One big bastard in particular caught my eye. His ragged fins marked him a survivor of many winters. He ignored my bait, as did the other trout.
We all waited in silence, staring balefully at one another.
Suddenly inspired, I snuck up on the old trout, keeping my shadow out of his view. I slipped my left hand under his belly, and with a sudden motion tossed the terrified trout onto the grass.
I was so excited that I fell into the stream, where the trout badly wanted to return. My hiking boots were now soaking wet.
The icy cold water sent me flying back ashore where the old trout was flopping in a mad attempt to get back to where I’d just exited. I barely caught him in time. He was dinner.
I dumped the water out of my boots and set them on a sunny rock to dry. I was now barefoot for the rest of the afternoon.
The hell with the fishing rod. Trout tickling (I didn’t know there was such a thing until much later) was a lot easier. After I’d secured my still-swimming dinner I set about walking the area in the warmth of the early afternoon.
I stumbled on Porcini mushrooms, which were in early fall abundance. They’re edible (I didn’t know that at the time, but I assumed so, which was monumentally stupid on my part). I picked several armloads.
That night I cooked my trout and the Porcini mushrooms in butter, and had the raspberries for dessert. I ate mushrooms until my tummy was painfully full.
I was a true woodswoman, eating the results of my hard work.
I was supremely proud of myself, wax helmet head, wet boots and all. I can find my own food, I thought with pride.
That night, after falling into a blissful sleep, I awoke to severe stomach cramps.
It’s one thing to test a new food. It’s quite another to consume so much of an alien delicacy that your whole body revolts. I almost didn’t make it out of the tent in time.
The rest of that cold, moonlit night was punctuated by rapid-fire sprints into the shadow-patterned woods nearby.
I ran out of toilet paper. Of course I did.
You don’t want to run out of toilet paper when you have the runs.
I also invited an army of mosquitoes into my tent, which took full advantage of every bit of exposed skin. By morning my face and arms were covered with itchy red mounds.
The Great Woodswoman, indeed.
My shoes were wet. My gut was on fire. I was out of toilet paper. My pack was still 78 pounds. The trip back down the mountain was punctuated by stops to relieve myself of the previous night’s mushrooms and raspberries.
They were just as eager to leave my body as I was to get to a proper bathroom facility.
Bitten, bruised, embarrassed and thoroughly humbled, I stumbled back to my car for the short drive home.
I may well know precisely how Cheryl Strayed felt.
My trip to Australia, New Zealand and Fiji, which began with a serious thigh injury (there went walking “the entire country”), was a sheep dip in humility.
But here’s the piece.
When faced with insurmountable odds, you either learn to problem-solve and work with what you have, or you injure.
Or you die.
Nature has a way of getting rid of morons who climb fourteen-thousand-foot mountains in Keds and cotton shirts. Or who think that taking their iPhones guarantees a swift rescue.
However, She also presents opportunities to discover who we can be, what we can do, and how well we can problem-solve in the wild. Such is the learning arc. I’ve been on it. Still am.
If we survive that first outing, we’re remarkably better-prepared for the next.
Strayed’s story, which so deeply offended my much younger outdoor women friends, was to me a sweet reminder of our innocence any time we begin a great endeavor.
They themselves may wish to forget the mistakes they made on their first backpacking trip. We all do it. We have to.
Without those mistakes, we don’t respect our vulnerability. Conditions which demand our humility.
That leads to arrogance, and arrogance leads to disregard of real dangers. Arrogance kills.
Such opportunities for innocence happen until we die. Every time we try something new we’re vulnerable. The older we get, the more important it is to be open, soft and curious. To know when we’re ignorant.
To know when hubris can be fatal.
We are Too Old and too experienced to think we know it all.
To believe we’re invincible or incapable of serious error.
Strayed made it to the very end of those parts she committed to, all in one piece.
From 1984 to 1987 I hitched solo around three countries, learning to fly ultralights, diving the Great Barrier Reef, and pushing my boundaries.
I made countless ridiculous, laughable mistakes.
Mistakes I rarely make any more. Without them I would have no competence today, nor would I have a slew of screw-up stories.
Truth is I still screw up regularly. It’s the price we pay to explore. My feeling about those blunders today is a different. I frankly don’t care if anyone sees me. An audience for my face plants is half the fun.
Perhaps this is the benefit of age and perspective.
However, life-threatening conditions on multiple occasions have taught me that humor is life’s best weapon against mind-numbing fear.
I’ve been upside down in a kayak in ice-cold water more than once. I’m terrified of drowning.
Yet I recall thinking, “Well, this SUCKS. Hm. Cold water. Fast rapids. Rocks ahead. Huh. Better get the f*ck out of here, ya think?”
In seconds I was bobbing on the surface, my kayaking buddies helping snag my boat. Laughing.
The rigidity of our need to do it right the first time, every time is a recipe for disaster.
Strayed’s book was a fine reminder that we are all beginners at something. We will fall. We will fail. We will falter, which reminds me of my favorite Enya song, Book of Days.
And in doing so, we grow.
Strayed wasn’t stupid. She was ignorant, as are we all when we start something completely new. Nothing wrong with that.
What’s wrong is never trying, never starting out, and never giving ourselves permission to laugh at our mistakes.
I salute the Cheryl Strayeds of the world. At least they try. That’s more than I can say for too many of us.
The more permission I give myself to fall, the easier the landing, the wiser I get, the faster I get up.
At any age.
Let’s try. Let’s fail. Let’s make mistakes. Above all,
Let’s play.
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Great story telling. Loved it! And so much truth there.
This was an awesome story. I applaud people like you and Cheryl Strayed because I'm pretty sure I'm fine jusr watching other people do this 😁