The Wisconsin River cuts a brown snake through a dense Midwestern forest, maybe 300 yards across. We paddle along the south shore, chasing the bubbles that indicate a faster current.
Five days and 125 miles in, I’m exhausted. We all are. Fifty miles on foot. Fifty miles on a bike. Now 25 miles to go in our green canoe.
A September breeze softens the harsh sun. Paddles dig through the water. I settle into a perfect calm — until someone cries out behind me.
There are 10 men in our group, in five canoes spread across the water. We turn to find the doctor and the pastor are stuck on a submerged tree. As we all shout instructions, they try to paddle forward, then backward, but their canoe won’t budge. Another team tries to tow them out, to no avail. My mind races with nightmare scenarios. What if they capsize? What if they fall underwater and get stuck in the branches?
I had envisioned this trip as a celebration, a test, a respite from anxiety. I called it 50-50-50 in honor of my looming 50th birthday. But honestly, the past year had been horrific. I’d survived COVID-19, as had my children, only to see my mother succumb to cancer. Forced to confront mortality, I’d hardly slept since the funeral. I needed relief and hoped an adventure with my friends would bring it. I wanted to do something hard, but this isn’t what I had in mind.
On day one, we gather before dawn in the parking lot of my church in suburban St. Louis and convoy six and a half hours north, in two pickups and my old hatchback. By afternoon we’re on the Ice Age Trail, not far from Madison, 10 men at various stages of middle age. We hike a meandering dirt path over rolling hills and through thick forest. Yellow rectangles called blazes painted on trees mark the way, which crosses a couple of rural roads. I bounce between the front and the back, eager to lead, just as eager to hang back and talk.
We all belong to an outdoor fitness group, and I often organize physical challenges like 250-mile bike rides, paddling trips on the Missouri River, or doing 100 burpees every day for a month. Today’s 15-mile hike is the first leg in an itinerary cobbled together across southern Wisconsin. But it’s easy to get lost in the moment out here. Like when the trees part, revealing a small lake rippling in the wind. The day is three steps short of perfect. Back at the trailhead, the mechanic rolls his ankle and tumbles down the stairs to the parking lot. Before long it swells to the size of his calf.
Back at our Airbnb, I take a private room, hoping it will help me sleep. Instead, I toss and turn for four hours, worried about his ankle.
It’s worse the next morning, with 20 miles to cover. The doctor, a gastroenterologist, wraps the ankle, joking, “I finally get to use my first-aid kit.” On the trail, I study the mechanic’s stride from behind. He’s limping and his right shoe pops loose with every step. He keeps up the pace, but I can’t help worrying. What if his ankle snaps six miles from the car?
After a dark foreboding section of trail thick with bushes and weeds, we descend into another stretch cleared of undergrowth. Pine trees stripped of low branches look like scattered telephone poles that form an optical illusion, as if I can see into infinity. I see aging metaphors everywhere — even in the leaves’ apparent resistance to change colors.
There is no resisting: Death comes for us all, and it’s coming for me sooner than I’d like. It’s easy to look back at my first 50 years and wonder what I’ve done with my life. I try not to do that, but it’s one of the uncomfortable realities of middle age: Sometimes it’s easier to look back rather than forward.
The mechanic’s bike comes off the truck with a broken tire stem, but changing a tube is quick work. Soon we’re cruising west on the Glacial Drumlin State Trail, a converted train line that runs 52 miles from Milwaukee to Madison, with no cars or big hills. We roll past cornfields and small towns, old railroad depots and waterways. When the group stops at a gas station for snacks, the pastor and I rest in the shade of a small tunnel. The respite is short-lived. “I’m finished,” the mechanic texts to the group.
His ankle is holding up, but his derailleur has snapped and his nerves aren’t far behind. We brainstorm a fix, removing the offending part and trimming the chain to fit, converting his 18-speed bike into a hipster single-speed. It gets us moving, albeit more slowly, interrupted whenever the mechanic howls that the chain has slipped again. Each time, we gather around, shine our lights and encourage him as he puts it back on, cursing.
The sky glows purple and orange as the sun drops behind a marsh. Bugs ping against my face. My headlight catches a rabbit darting into the trees. As we climb the last knoll, the chain slips again and the mechanic surrenders, coasting downhill to the pastor’s pickup.
That night, I lie in bed, eyes wide open. Hours tick by. I take cough syrup, the kind that makes you drowsy. But every time I’m about to drift off, I jerk myself awake. My mind feels like I’m watching a fireworks display, only in place of the dark sky there’s a strobe light and instead of oohs and aahs I want to scream.
I’ve struggled with insomnia, but never so bad as the months since I gave my mother’s eulogy. The cancer in her jaw came back last year, right around the shutdown. She made it nine months, enduring shingles, a gallbladder problem and a couple of falls. We tried to visit my parents for the holidays, but my daughters and I tested positive for COVID-19, so we had to settle for a video chat on Christmas Day. She looked like she was on the verge of death. I knew I’d never see her again.
My mom was all smiles and friendly energy. If you went with her to the grocery store, it could take two hours, and you’d surely get to know the cashier, the manager, even the stocking clerk. She didn’t want a funeral. She wanted a party, so we threw her one when the pandemic allowed, with drinks and a taco bar. I found myself pondering my own life and what people might say about me when it’s my turn to go. I wanted to give them plenty of material to work with. More than anything, I wanted my eulogy to be like my mom’s.
That’s how I ended up here, waiting for a morsel of sleep.
Heading to the river, I can barely function. Two hours of sleep last night, 16 over four days. I can’t drive my own car. I try to say something about floor mats, but the term won’t come. I call them “the thing in the car you put your feet on.” At the put-in spot, a bald eagle sits on a thumb of sand and I watch in a stupor. My brain is a moth without a light.
I pair up with the pilot because he has arms like a lumberjack and he used to fly a fighter jet, so I trust his nerve. He steers the canoe while I paddle weakly in front, snarfing candy and electrolytes until I start to feel like myself.
As the afternoon heat burns off, we find an island to spend the night. I set up my tent and inflate my mattress and pillow, ready to pass out. Instead I rally to enjoy tacos and stories by the fire with my friends. The soft sand makes my best bed all week, and it’s a good thing.
By midmorning on day five, the canoe is stuck and so are my friends, trapped by their own weight. Somebody’s got to get out. It’s risky. They’re wearing life jackets, but they could still get sucked under the tree or swept downstream. The doctor goes first, standing on a slick branch to steady himself before slipping off. Another team pulls him to shore. Now it’s the pastor’s turn. He is my pastor. His wife teaches my daughter piano. His kids go to youth group with mine. He lowers himself out of the boat and disappears into the water.
Pop back up, man.
POP BACK UP.
Finally, his salt-and-pepper hair resurfaces.
The canoe gives, and he holds it against the current until we can tow it to shore.
Later, we stop at a roadside diner where Amish families roll by in horse-drawn carriages. We stink of sweat and muck, and I feel for the server. There’s no vegan menu, so the doctor orders his first burger in years. I soak fried catfish in tartar sauce while the pilot mulls a second meal. Already we’re reliving our grand, exhausting, scary adventure.
I’m 50, and no, I won’t live forever. In fact, I’m closer to the end than the beginning. This is unsettling, to say the least.
But I want to keep my focus on what still lies ahead. I want to get the most from my talents— including the ability to form and strengthen deep and meaningful relationships. It’s one way I remember my mom and honor what she taught me.
I know there will be ups and downs, accidents and injuries and mechanical failures. But there will also be awesome, sweet, small moments I never want to forget, like the taste of tartar sauce on fried catfish at a roadside diner with my best friends. I want more of that.