Preparing For An Adventure

January 15, 2021

I set personal goals a lot. I meet them a lot too, because I have this weird OCD which gives me this lovely amount of anxiety if I leave those goals undone. Unfortunately, that OCD doesn’t work on other things like cleaning my desk. That’s not to say I finish every goal I set for myself either, because that’s far from true. But I am not one to forget the expectations I set for myself, for better or worse.

Usually those goals revolve around my business, or work. But recently a piece of advice hit home for me from someone I’ve been following lately, Dan Milnor. He told a story about how his whole life revolved around photography, and it made him boring so he took up some other hobbies. I am sure I criminally misrepresented what he was saying, but it really made me think hard. It actually kinda haunted me for a bit… because I feel the same. Especially now that my primary photography income is from real estate photography. It’s not interesting at all. At least when I used to work on assignments, I was shooting things people might. be interested in… but no more. Over time, I took my hobby and my passion and turned it into work and I can’t remember the last time I put an emphasis on making things for myself.

A few years back, I took up cycling and it’s opened up a whole new world for me. Long ago John Lewin told me about riding a motorcycle around shooting photos. He liked it, because he could stop anywhere he wanted easily and take photos. It does seem cool, but Sadie won’t let me ride on a motorcycle… For some reason, though, she thinks a bike is much safer and an acceptable mode of transportation. So… naturally, I am going to push that safety to it’s absolute limits and am currently planning my first bikepacking trip for this year.


This road is criminal. It doesn’t go anywhere, it’s just an access road, but it’s a fun little gravel road which I would love to add to my daily ride and it’s just outside my neighborhood, but the sign says no bikes.

Bikepacking & Me

I am not particularly physically fit. I don’t know if I really ever even passed those Presidential fitness challenges we used to get when I was in elementary school… if I did, it was just barely. I remember reaching for my toes and thinking there is probably no more painful activity on the planet. Recently my Dr suggested I try yoga and I thought back to those days… I remember that little box, and the measurements and everything. It was a minor trauma for little kid Kyle.

I never tried yoga.

So, as you can probably imagine, this is going to take some work on my part. I’ve gone through spurts in the past of trying to get in shape. I’ve even managed to lose a significant amount of weight here and there by eating right and doing some basic workouts. But this will be much different. One of the routes we’re looking at has over 6k ft of climbing over 75 miles… to be done in 2 days. Yeah… that’s like… beyond anything I’ve ever done before. It’s not something I could ever attempt alone. At least not yet…

Which is why I enlisted two of my closest and oldest friends (and the roster might be growing!). They’re both way more accomplished than I am. Zac has ridden cross-country TWICE. And Drew has completed the Iron Man and I am pretty sure 100 mile runs. I’m way out of my league here. Luckily for me, they agreed to come along to push me and to hopefully share an unforgettable trip with two guys I’ve known most of my life.


This is my first ride around my neighborhood. I will use this ride as a measurement of my progress measuring how quickly I can do the same route.

The Trip

We’re currently planning and getting the last bit of gear and supplies, but it looks like we’ll be picking between one of two rides in western NC. They’re going to be hard (for me at least), with thousands of ft in elevation gain and “roughing it”. We’ll sleep outside, I am sleeping in a hammock, and drink water filtered from natural sources. I am a little nervous about those two items, and the weather. I’ll have two people I trust with my life alongside me, and that brings me solace.

Should this trip go smoothly, I hope to plan more in the future. I’d like to add them to my website as I focus it more on my passions than simply on getting work. I’ve got a lot to do to get ready, and this is just the beginning, but if you’re interested, I’d love you to follow along! Hopefully I can share some interesting words and photos along my journey.