Try and Fail

I’ve long held the belief that it’s better to try and fail, than to never even attempt doing something. Along with a few successes in life, I have had a very long list of failures to my name. Here’s a story about one such failure.

I was at a social gathering a few days ago and I had a conversation with someone about how I’d tried to paddle a canoe down the Mississippi in 2017.

Our conversation then turned to a dialogue about how I’ve tried a bunch of things outside my comfort zone over the years, and failed at many. Adventures, projects, businesses, making friends, and so on. Many people will never bother to even try doing hard things, only because they’re hard.

Paddling the Mississippi #

I’m certainly not the first person to try paddling the Mississippi, but very few people have managed to do it from the headwaters all the way to the gulf of Mexico. Additionally, few have done the entire trip solo.

I decided to bring a camera with me, with the goal of documenting my journey with a daily video log. Until now I didn’t bother doing anything with the video footage, because I didn’t think it would interest anyone.

Start of Day 1 #

I began day 1 in good spirits. I started at Lake Itasca and set out with the expectation that I’d be living in a canoe for 3 months. I was carrying a bunch of equipment with the assumption I’d have time for leisurely enjoyment of the open water: solar panels, camera gear, my laptop, speakers for listening to music, a ukulele, and a harmonica. I had around 200lbs worth of the wrong gear.

As things went on, my spirits declined. The water was incredibly shallow, so I spent most of the day dragging the boat over rocks with heavy gear on board. I (foolishly) did not prepare for this and it was exhausting. I had planned to be spending time paddling, not dragging a boat along the ground.

End of Day 1 #

By the end of day 1 I was exhausted, felt alone, had no cellphone reception, and wasn’t having the fun I expected. I only slept a few hours, and remember mostly laying awake waiting for the sun to start coming up so I could head out.

Before I tried to sleep for the night I recorded one final video.

Day 2 #

I thought that day 2 was going to be better, but it wasn’t. If anything, it was harder because all I could see was grass with no signs of civilization. My phone wasn’t working and I didn’t have offline maps.

I was approaching Lake Bemidji, which meant that I’d have to cross a lake, which can be very difficult in a canoe if there’s wind. Being near Bemidji also meant there was an opportunity to abort the adventure if I needed.

I was entering into a part of the river where I’d have to portage my canoe and equipment at a series of dams and weirs along the Mississippi, but it was going to be painfully slow and difficult with everything I was carrying.

I stopped once more and camped for the night on land that I think was used for cattle grazing.

Day 3 #

On the morning of the 3rd day I decided to quit. I had gotten quite close to Bemidji, but I wasn’t having fun and I didn’t want to continue. I didn’t think there was any point in doing something that I wasn’t enjoying.

I was not physically prepared, I had the wrong gear, and more than anything else I was not mentally prepared for this trip. I didn’t expect to feel disconnect and be in remote wilderness. I felt a lot of anxiety about continuing.

Try and Fail #

While I’m not overly proud of my lack of accomplishment in this particular case, I’m also not entirely ashamed. I will never have any regrets about not having tried to paddle down the Mississippi because I know that I did, in fact, try it once. I tried, and I failed.

Maybe some day I’ll give it another shot now that I have a better idea of what’s involved.