I bought my hiking boots in September 2012 in advance of my first overnight hike. I was so excited that I only got about 45 minutes of sleep the night before. When my three buddies and I arrived at the trail, it was pouring. The boots are waterproof, but that didn’t matter. It rained so hard and for so long that the trail literally became a stream, and my feet were soaked within a few hours. No waterproofing on earth would have protected me from that flood.

We slept that night in an old barn that had been converted into a shelter. When we arrived, soaked to the bone and shivering, the barn stood empty. By the time it was dark, 28 people were camped out in there, and approximately 24 of them were smoking dope.

When I think of that hike, I think of the rain, all those potheads and the boots. I can still see my feet striding on opposite sides the trail-turned-stream, all too often slipping into it. I can feel the balls of my feet as I ran down the stairs of the barn. I can sense the heat as my toes pressed hard into the soles against the rocks that lined the fire pit.

They’re just pieces of leather and rubber and whatever all stitched together… but they’re far more than that. Those boots have taken me, literally and metaphorically, to places I never expected to go.

I didn’t know it then, but that two-day hike became a turning point in my life. Since then, wearing those Merrell boots, I have hiked hundreds of miles and climbed dozens of mountains. I have hiked with temperatures in the single digits and the triple digits, in rain, snow and fog, on perfectly calm days and in wind so fierce I couldn’t face it. I hiked first for fun and then for exercise, and eventually I started to get paid to hike and write about it.

Last week I went for a hike on my local greenway, and while trying to tiptoe around a puddle, I stepped in wet grass, and both my feet were immediately soaked. I have worn holes into my boots, and boots with holes do me no good. I have to get rid of them, and I’m bummed. They’re just pieces of leather and rubber and whatever all stitched together… but they’re far more than that. Those boots have taken me, literally and metaphorically, to places I never expected to go. I might keep them even though they’re useless.

We all own something like that, don’t we? It might be an old baseball hat or a concert t-shirt or a pair of jeans that used to be cool to wear out then were cool to wear around the house then were cool to cut the grass in and now you just can’t throw them away. A friend of mine has a pair of sweats he loves so much that when they became unwearable, his wife cut the legs off and sewed them onto a hoodie as sleeves. When he wears that thing, his arms look like the wings from a bird of my kid’s nightmares.

I thought saving clothes long past their usefulness was a guy thing, but two women friends separately told me they have T-shirts from 1994 that they still wear all the time and a third still wears her wedding shoes … and her 50th anniversary is later this year. Another friend first dyed her wedding shoes from white to black and then took them to the cobbler multiple times to get them resoled. They were expensive, comfortable, dance-in-them-able, and she wanted to keep wearing them for as long as possible. But this is how her beloved shoes met their end: “Over Christmas, I spilled maple syrup on them and realized they were finally done. I left them in a garbage can on Main Street outside of the cobbler’s shop. Now when I pass by that garbage can, I think of my shoes and where they’ve been.”

Sweatpants, hiking boots, wedding shoes—however disparate these items may be, they all connect us to vivid memories. However irrational it is to say out loud, giving up those items feels like giving up on the memory. Or worse, the item getting worn out reminds us that we’re getting worn out, too.

Such stories are so prevalent that writer Emily Spivack collected essays and turned them into a website, which became a book, called, appropriately enough, Worn Stories. In the intro to the New York Times bestseller, she describes our favorite items as “encoded with the stories of our lives.”

Sweatpants, hiking boots, wedding shoes—however disparate these items may be, they all connect us to vivid memories. However irrational it is to say out loud, giving up those items feels like giving up on the memory. Or worse, the item getting worn out reminds us that we’re getting worn out, too.

Maybe, like those brides, your item is tied to some particularly important event. Maybe it’s a Red Sox hat or your alma mater’s shirt, and you love it for the fun times it brings to mind. My boots combine the important and the fun. As horrible as the rain on that AT hike was, it was also awesome. And hiking, with the help of those boots, helped me get through the most difficult period of my professional life.

About six months after I bought the Merrells, I was laid off from my full-time magazine job. I was unemployed for the first time in my life, and the first few months after that are a blur of stress and despair. I tried to start a freelance writing career but discovered I knew how to write a story but didn’t know the first thing about selling a story. I tried to find a job but learned that the entire job hunting experience had completely changed since the last time I looked for one.

At one point I counted that I had sent 18 resumes for open positions and had not gotten even a “we received your application” email in return. I sent out story pitches, waited five minutes, then refreshed my inbox obsessively in anticipation of responses that never came. I spent long hours in my home office knowing I was missing something but clueless about what that something was. I had to get out of there. So I laced up my boots and hiked. A lot.

boots comp

I didn’t have any epiphanies on those hikes. I didn’t find what I was missing. I just went on them to stop myself from going crazy. This continued for several months until I slowly figured out how freelancing works. And even now that I have plenty of work to do, I keep hiking. I take my phone and digital recorder with me and conduct interviews from the middle of nowhere. If I am struggling with a particular part of a story, I use that as an excuse to go for a hike and think about it, and by the time I get back, the problem is solved. Sometimes I pack a lunch and a lawn chair in my car, drive to a local trailhead, sit in the chair, turn on my laptop, write for a few hours and then hike for a few hours.

My favorite story about my boots concerns the time I feared they’d get me busted by the TSA. Backstory: I write for the National Guard’s official magazine. The editors send me on all sorts of awesome assignments. A few years ago, I covered a combat engineers’ competition. Wearing my Merrells plus a Kevlar helmet and a Kevlar vest, I ventured into the demolition range with a team from West Virginia as they set up bombs. Even though we hid behind a concrete bunker, the concussive force shook my ribs.

A few days later, as I left for the airport, my military handler warned me that I had been around explosives all weekend, and that if I was flagged for TSA inspection, I would come up hot. He gave me a colonel’s phone number and told me to call him if anything happened.

And guess what happened? The TSA agent chose me for random inspection—the first and still only time that’s happened to me. He ran his swab all over my backpack. It came up hot, of course. I stood there thinking, my job is so cool I get busted by the TSA. I explained to him who I was and pointed to the dozens of Army guys sitting nearby, all of whom had been part of the competition. He was very nice and professional about it. I didn’t even have to call the colonel—the agent searched my backpack, gave me a more thorough pat down, and let me go.

I was told to never bring that backpack to the airport again because the sensors are so acute it would come up hot every time. The same logic applied to my boots, which were surely covered with explosive residue, considering I had walked exactly where hundreds of bombs had exploded.

Since then, I’ve left my boots at home when I’ve gone on the road. I usually try to sneak in a hike wherever I go and settled for doing that in my sneakers. But in October, I was assigned a story that required hiking in Maine, and the boots were a must. I had to bring so much camping gear in my luggage that I had no choice but to wear the boots through security. What if I got stopped again, and this TSA agent wasn’t as nice as the last one? Would they be confiscated? You can’t take a bottle of water through, so hot boots seemed like a legit concern.

I didn’t want to risk it, so I called the TSA, but the person on the phone was about as helpful as you would think someone on the phone at the TSA would be. Which is to say, the next thing I did was drive down to the airport with the boots. Maybe this sounds ridiculous, but I wanted them tested before I tried to bring them through security. The TSA agent there gave me a “you’re a nutjob” look (which I get a lot). She assured me that a) lots of things falsely set sensors off, so I shouldn’t worry (which was interesting but ignored the fact this would not be a false-positive, this would be a positive-positive) and b) TSA agents almost never check shoes anyway. A few days later, still a little nervous, I got through with no problem.

That was an all-time great hike, but I could sense that the end was near for my boots—the toes started to come apart. The soaking last week confirmed they were finished. So now I have to buy a new pair. My plan is to simply order another pair of the exact same Merrells. They’ll be the same, but they won’t be equal. The new ones won’t be heavy with memories. Not yet, at least. I plan on putting those things to work.