The Outside Adventure Grant: Gone and Back Again

We gave a former corporate lawyer $10,000 to fund his back-of-the-napkin plan to sea kayak from Minnesota to Florida. He made it all the way—then he turned around and started paddling home. Here's why.

Daniel Alvarez

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I could have quit. I’d done what I set out to do when I won Outside’s 2012 Adventure Grant: Kayak from the northernmost tip of the contiguous United States to the southernmost point, 4,000 miles from Minnesota’s Northwest Angle to Key West, Florida.

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Daniel catches the sunset on an oak tree in North Carolina. Daniel catches the sunset on an oak tree in North Carolina.
A manatee swims up near Daniel in Florida. A manatee swims up near Daniel in Florida.
Daniel at the start of his adventure. Daniel at the start of his adventure.
Daniel takes part in a turtle rescue. Daniel takes part in a turtle rescue.

The trip took nine months. I portaged across dozens of northern lakes, dodged barges in the Mississippi River, and skirted waves in the Gulf of Mexico, but this past March 11, standing across the finish line in Key West, I didn’t feel finished.

“What will you do when you get there?” a man asked seven months earlier on a dock in Minnesota. “Paddle back?”

I laughed and covered my ears in mock horror.

“Don’t give me crazy ideas,” I said.

It was a nothing moment, a joke between strangers. I don’t remember what he looked like or where it was because it happened again and again, month after month, from Minnesota to the Gulf Coast, always the same joke, the same laughter, and the same disbelief at the possibility.

The idea of paddling back felt like the far-fetched adventures I dreamed up when I was a lawyer in San Francisco and stacks of paper made my office walls feel tight. I’d stare out my window at rows of corporate towers and think of walking from Mexico to Canada on the Continental Divide or hitch-hiking on sailboats around the world. Then I’d turn back, pick up a stack of paper, and start marking up hundred page credit agreements.

“Well that’s just silly,” a woman said in Florida after her husband made the joke about turning back. “You can’t paddle up the Mississippi.”

Then we all laughed on cue, like the current of the Mississippi was what made the idea ridiculous. I smiled like always, but I knew I didn’t have to paddle back on the Mississippi. The joke had been growing on me and I’d looked at a map. I could head up the East Coast to New York, connect to the Great Lakes through the Hudson River, and make a loop out of the whole thing, end it right where I began.

I had a thousand reasons why it wouldn’t work. I wasn’t ready to go back. I didn’t have another grant to cover my costs, just a thinning bank account and a credit card. My body felt as worn as my equipment looked, full of ripped seams, scratched plastic, and rusted metal. Winter would freeze Minnesota’s lakes in seven months and it took me nine to reach Key West. The only research I’d done was chat on docks with power boaters, glance at a map, and figure they get those saltwater freighters into the Great Lakes somehow.

“I wish I could do it,” I thought to myself. “But…”

It’s the same thing people say to me when they hear what I’m doing. “I wish I could do that,” they say again and again. I’ve heard it on every trip I’ve ever taken, always followed by a parade of excuses.

“If I were younger…”

“If I didn’t have my career…”

“If I only had the money…”

People always sound like they don’t quite believe their words and they’re convincing themselves of the truth. I’m never sure what to say back because I think the truth is that it’s easier to blame the world than yourself, that there will always be excuses not to go if you want them, that we’re trying to rob ourselves of the decision, but that’s a hard truth and most people don’t like to face it. I know I didn’t.

I met a one-legged hiker on the Appalachian Trail. I finished the Continental Divide with a 72-year-old. I swapped stories with a one-handed man who celebrated Lewis and Clark’s anniversary by trying to paddle up the Missouri River. They had excuses, too.

Today, I’m on the Outer Banks of North Carolina. I’ve paddled a thousand miles from Key West. My gear is still ragged. I barely know the route ahead. I haven’t showered in two weeks. Salt has worn my skin raw. My muscles ache. Two nights ago, I slept in a rotting, shit-covered duck blind because I couldn’t find a campsite. And I’m running out of food.

But last night a sunset transformed the sky and ocean into a canvas of pink and made me forget everything in the world for a moment. I’ve passed ancient Spanish forts and launch pads that send spaceships into orbit. I traded mangroves for palm trees and palm trees for pines and gnarled oaks. I stood on the wall at Fort Sumter and imagined the start of the civil war. I shared a plate of fried chicken and pitchers of sweet tea with a table of strangers in a old boarding house. I watched clergy bless shrimp boats parading past a dock and saw wild horses race across beaches.

But I could have quit in Key West.

New York is five hundred miles north along the coast. Montreal is another four hundred up the Hudson and through Lake Champlain. From there, a thousand miles will take me across the Ottawa River, Lake Huron, and Lake Superior to Thunder Bay. Then three hundred miles of lakes, rivers, and old portage trails gets me back to the Northwest Angle.

There’s an old metal obelisk there marking the border. I remember kissing it for luck and snapping a picture. Now the picture makes me laugh because I had no idea on that day that I wasn’t only standing at the beginning of my journey, I was standing at the end. At least, I hope so. I may make it, I may not, but I’m going with all my heart so I’ll never say “I wish.”

Adventure is a choice. Don’t steal it away from yourself. Make it. Be bold. Go.

The application deadline for the 2013 Outside Adventure Grant, a $10,000 endowment to fund your dream expedition, is June 1.  Follow Daniel Alvarez’s progress back to Minnesota at