3 Lessons From my First Week of Riding

I’ve been on the road for about a week now, albeit with a couple off-days sprinkled in to rest while I build up my mileage.

I’ve already ridden against headwinds and in the pouring rain, up hills I thought I’d never get to the top of, and through endless stretches with no services and only the occasional driver passing me by.

My legs are shot, my stomach is growling, and my face and ears are recovering from sunburn.

But if you were to ask me if I regretted quitting my job and setting off down this road, my answer would be a confident “no”.

To be honest, I’ve never had a career. I really don’t even know what a "career" is.

I’ve essentially been living on the road for the past several years now. And it’s gotten to the point that I’m not even interested in a 9-to-5 anymore.

What I do want is to help you, my dear reader.

I want to help you reject the status quo and create your own adventure out of this wild ride we call life.

So in this first blog post from the road, I wanted to take the time to share with you three lessons I’ve already learned from my first week of riding.

Lesson #1: Focused effort is a more efficient use of your time than "winging it".

When I initially had the idea of doing a training ride before heading up to Prudhoe Bay, I thought about biking around southern Alaska willy-nilly until it came time for me to fly north.

That plan might have been okay in theory. But I’ve found that if I don’t have a set idea of what I intend to do – in a day, a week, or even a year’s time – I tend to sit around staring out the window.

I grab a snack because I’m bored, and then keep eating because I don’t know what else to do. Then I maybe watch a show or go on a walk. And when my friends say they’re going out, I tag along and eat more food that’s terrible for me.

You know what I’m not doing on those kinds of days? Anything that brings value to my life or to the lives of the people around me.

Oh sure, if you sit enough monkeys down in front of typewriters, eventually they might write the entire works of Shakespeare.

But the process will be a lot more painful and take a lot longer than it took the Bard to plan out and write his own works.

And you’d have to clean up a lot more monkey dung, too.

So that is to say, give yourself a goal. Preferably one that’s SMART: Specific, Measurable, Attainable, Realistic, and Time-bound.

For example, I said I’m going to ride my bicycle 585 miles from Homer, AK, to Fairbanks beginning on May 15th, 2025, for a period of about two and a half to three weeks. So far, I’ve ridden 238 miles with two(ish) weeks left to go.

When you make a goal like that, “all the universe conspires in helping you to achieve it”, so says Paulo Coelho in The Alchemist.

Lesson #2: Taking a day to rest doesn’t mean you’re being lazy

When I biked around a bend on Day 3 and saw the sign I’d been looking for all day, my whole face lit up. I’d made it to the lodge I’d been working at for the previous two summers, and I was exhausted.

It was only my third day of riding, but when you go from biking an hour a day a few times per week to biking 6-8 hours a day for three days straight, your body tends to not be so pleased with you.

All I wanted to do was take a warm shower and eat a hot meal, then crash onto a mattress and sleep until I woke up.

You hear stories of people completing incredible feats with little to no training or achieving one accomplishment after another in seemingly impossible fashion.

We all marvel at these people and wish we could be like them.

Let me be the first to tell you that I am not one of those people.

In the process of training for my first marathon in 2024, I developed what I only later learned was runner’s knee.

Apparently, according to an orthopedic specialist I saw afterwards, most people's legs are about 5% out of alignment.

But my legs are closer to 10% out of alignment. My lower legs bow outwards.

So any repeated impact I make with the ground over long stretches of time – say, as in running long distances – forces more pressure against the insides of my knees.

About a month out from my race, my left knee had had enough. It became excruciatingly painful to run just one mile. So I’d rest a couple days and try again. Still painful.

I rested the entire week leading up to race day. I decided to still race. The morning of, I was feeling good. It was a beautiful day, and my knee didn’t hurt after a warm-up run. Good to go. Or so I thought.

I ran the first seven miles no problem. I had a smile on my face. I was unbreakable.

I hit the first aid station and slowed down to sip an electrolyte drink. And that’s when it felt like somebody had flipped a switch in my body.

Out of nowhere, pain shot up my left leg. My knee buckled as I turned away from the aid station and I went from a light jog to a slow walk, and then to a pathetic hobble in just a couple of minutes.

I hobbled for six more miles, cursing and telling myself I was being a wuss for not running, until I reached the halfway mark and had to call a friend to come pick me up and bring me back to the starting line.

I’d been defeated. And at the time, that meant I was a loser.

But having to bow out of my first marathon showed me the importance of listening to my body. If it needs rest, I give it rest. If it needs to move, I get up and I move it. If it starts to stink, I wash it.

Taking time to allow yourself to recover from doing hard things isn’t a sign that you weren’t meant to do those hard things in the first place.

It simply means that you, like everyone else, are made of flesh and bone. Not steel.

So rest. And don’t apologize or be ashamed of it.

Lesson #3: Figure out what you want, then make a plan and do the work to get there

Last year was supposed to be the year I ran my first half and full marathons. Instead, I ran one half and hobbled another.

This year is supposed to be the year I ride a bicycle across America. But if something happens that forces me to re-evaluate my plans, I have no qualms about doing so.

If you’re someone who, like me, enjoys challenging him/herself and takes pride in doing what you say you’re going to do, it’s easy to see every failure or setback as a sign that says you’re just not cut out to do great things.

You’re not made with the right stuff. You haven’t trained hard enough. You’re just not meant to live up to your full potential.

Go lie back down on the couch and watch Netflix until your eyes melt into your skull.

Newsflash: That’s not the lesson here.

If all we were meant to do was lie around and stuff our faces with Cheetos, then why do we hold the people who don’t do those things in such high regard?

Why do we celebrate champions? Why do we reward people who accomplish great feats?

Because, deep down, we all know that the only thing that really separates those people from the rest of us is that they chose to do the hard things that we didn’t. We give them trophies and awards because they do the work that we simply weren’t willing to put in.

And so the question then becomes: What work are you willing to pour yourself into, and continue pouring yourself into long after everyone else around you quits?

If you love to mow lawns, you’ll mow more lawns than someone who just wants a J-O-B for the summer. And you'll make more money in the process.

If you love building software that helps people grow their small businesses and do more of what they love, then you’re far more likely to do so than someone who just wants to be known by his peers and superiors as some whiz kid software engineer.

And if you love riding bicycles and sharing your experiences with others, you’re going to ride across America through all kinds of weather, up hills, and in the most remote parts of the country, even when all you feel like doing is lying in your tent with your sleeping bag pulled up around your nose.

This life is what you make it. So figure out what you want and then learn what you need to learn to grow into the person you want to become.

And then become the person who serves the people around you by simply doing what you love. With focused effort over time, you’ll start to make some traction to the point where you can do that thing full-time.

Then it’s "look out, world". Because there ain’t no stopping you now.