I had been thinking about this for a long time.

In May of 2018 I cycled from North Dakota to Georgia. I went through Minnesota, Wisconsin, Illinois, Tenessee, Alabama, then ended in Atlanta, Georgia. It was only 5 short months after finishing my skate across the country, and I did it on extremely limited funds. It was a fantastic trip, but one thing stuck to me during the whole thing: what next?

I already knew what was next. When I stopped in Wisconsin at a kind person’s house along the Mississippi, they told me that normally they don’t get cyclists going through – they got kayakers or paddlers in general. Apparently, and I had never known this, people frequently kayaked along the Mississippi from Itasca State Park in Minnesota to the Gulf of Mexico way down south. I had never even considered it, but the more stories I was told of people passing through, the more it stuck with me.

I knew I was an accomplished endurance athlete. I managed four 100-mile rides on my cycle trip that took less than two weeks and made an incredible pace that surprised me to no end because it had been nearly a decade since I even sat on a bike. Despite all the seat rash, tired calves, and bugged out or sweaty days, I pushed on. I took no rest days and had time to spare before then skateboarding 188 miles in the direction I came from. Seeing my prowess on a method of transportation I didn’t necessarily covet gave me the idea that kayaking the Mississippi was, without a doubt, the next adventure for me.

I read a story about a guy who had just cycled the California coast, then realized he still had time from his work leave to keep going once it was over. He booked a flight to Minneapolis the next day, rented a kayak, and got moving. I found that to be extremely inspiring because not only did he completely skip the planning phase of the adventure, but he also did it on a whim. The same whim I had when I was feeling as if the world just wasn’t the same after skating across the USA. It’s this unmistakable itchy feeling you get day and night until you say, “I gotta get out of here.”

I think Caroline and I have been feeling that all over again. I’ve settled quite a bit more into my career, using everyday skills to get better however I can from behind my desk and three monitors. Caroline has been cooped inside recovering from ACL surgery, and the common denominator between us is that the adventure is gone.

Our lives have become quite codependent, however. We can’t just pick up and go. We pay rent now, and I work 40 hours a week. We have two cats, and a large space to occupy us with cleaning and preparing for whatever happens. It just wouldn’t be feasible, though it would be possible, to get up and head out on another adventure.

So this is my first step. I’ve decided that in the summer 2021 I will kayak the Mississippi River from Itasca State Park to New Orleans. 2021 seems so far, considering the turn of the decade was…today, but in reality, it’s a fantastic goal to set for me. I’ve been so preoccupied with training for Ultraskate and planning trips (or just paying for them in my case) that I can buffer the time with legitimate training. Once I achieve all my other goals, this one will replace them. So where now I am putting a major focus on leg strength and endurance, I can shift eventually to the upper body and especially core strength. I can take mini-trips, for the practical application, and I can gather gear in the interim.

I know nothing about kayaking. When my friend Brian drowned after falling into a quarry in my hometown back in 2007, I developed an irrational and unhealthy fear of dark water. That has eventually exasperated into thalassophobia and submechanophobia, but what better way to confront those demons than to spend two months on the water facing certain death? It’s not drowning that scares me (though that would be horrible) – it’s the darkness and the unknown that comes with it. The Mississippi will toss me in barges with delivery ships, in tiny alcoves with water mocassins, and on top of everything else my fingers don’t want to type while my brain thinks of them.

One thing that separates this trip from any other is that there isn’t much of a course to plan. I could look at each day and try to see how far and where to stop each day, but since I’m a novice paddler as it is with a penchant for training, it would be useless. The better thing to do for now would be to start following other traveler’s stories. Who finished? Who didn’t? Why? There’s a lot of unknowns and I’d be remiss if I didn’t put care into learning about them. The next step after that is to slowly start building a gear list and keep tabs open to check the classifieds in case there’s a sale. One thing I learned about these adventures is that you definitely don’t need the best gear or the most gear. But it sure does help.

So with a trip nearly 1.5 years away and a hunger to get there, the best thing to do is to stay humble, stay hungry, and stay interested. Avoiding things that will delay the trip or make it impossible is probably the number one thing I can do for myself until the planning part becomes necessary. All in all, I’m just glad that of the millions of ideas I’ve had, the ones I’ve always followed through on have been these adventures. Needless to say – I’m looking forward to it.