My 5 biggest regrets about riding the calendar year’s Triple Crown

W.When I set out to hike a National Scenic Trail for the first time in 2017, I had no idea I’d end up spending so much time hiking. Each hike is a completely unique experience, which is one of the things that has always attracted me to the trail.

You can hike as many miles per day as you like, spend as much or as little time in cities, take days off, do consistent mileage with no zero days, try to finish in a specific time frame, or take as much time as possible on the trail.

All of those options are wonderful and there has been a chapter in my life in which I have enjoyed each and every one of them. There have been times where I have loved going at a slower pace with a tram and doing all the side quests. And after diving into days of doing more miles, I found that I really enjoyed it too.

Prior to my calendar year 2025 Triple Crown attempt, I had completed the Triple Crown before and had hiked many different ways, but having to average 27.5 miles a day for the better part of a year was something else entirely. I wasn’t sure how it would go, how my body and mind would respond, and whether or not I would be able to finish the year.

Looking back now, months after completing the CYTC and then some, it’s been interesting to think about what I would have done differently. Honestly, I probably wouldn’t change a thing. Everything aligned perfectly, and even the negative things that happened were an important part of my growth and overall mission.

Today, however, I would like to share my few regrets from last year’s CYTC hike.

1. Being so hard on myself

When attempting a hike, especially something that covers higher mileage like the CYTC, you really have to be your own biggest cheerleader. There won’t be anyone else there day after day to cheer you up, wake you up early each morning, motivate you to keep going through the night even though you’re tired, or force you to leave town in the late afternoon because you know you can’t afford a lower mileage day. Every day I did that for myself because, frankly, I had to.

But most of the time I remember having a strong feeling of never being satisfied. Even if I did a huge mileage day, it never felt like enough. I could always have gone further, done more, and tried harder. It took a lot of self-talk to not focus too much on it at times and to be able to remind myself how good I was actually doing.

I wish I had been gentler and kinder to myself. There were times when I had that thought and took the time to talk to myself kindly and tell myself I was doing a good job. It sounds silly to pat yourself on the back like that. But you can easily become so focused on your goal that you forget to give yourself grace for how hard you’re trying and how much you’re asking of your body and mind.

If I could go back, I would have been kinder to that girl who walked 60 kilometers a day for more than two months straight, without a single day off.

2. Focus a lot on time

In a CYTC attempt, timing is everything. Last year it was very difficult to avoid harping on time and mileage every day. I certainly had a strong feeling that everything was going to work out and the timing always seemed to coincide very well. But it was still something I focused a lot on and had a lot of control over.

Worrying too much about a day or two here and there ended up costing me a lot more time in the long run. Last year my hip hurt a little when I was going through the White Mountains on the AT. As it turns out, a freak northeast storm hit in late May that dumped more than a foot of snow on the mountains of New Hampshire.

In retrospect, I should have taken a couple of days off to allow the snow to melt. Maybe even a handful of days. But instead, I climbed Franconia Notch in fresh, deep snow.

I would end up walking in freezing cold conditions, getting soaked, and moving as quickly as possible through the slippery snow to reach a warm shelter. My foot slipped out from under me a couple of times on steep snow-covered descents and I ended up severely tearing or spraining something in my hip. This would result in me having to take 17 consecutive days off to heal the injury and then having to do higher mileage again.

Looking back, it’s easy to say I should have been a little more patient and just waited out the snow. At the time, the idea of ​​sitting around for a couple of days waiting for the snow to melt seemed impossible.

Spending time at Shaw’s Hiker Hostel after getting injured in the White Mountains on the AT. Mentally, it was incredibly difficult to slow down. But I really needed it.

I think it’s also important to note that when attempting something like the Calendar Year Triple Crown, timing is incredibly important. I’ve seen many hikers end their attempts to stay behind on their mileage quotas and let them accumulate to the point where it’s no longer feasible.

But I’d like to think there can be a balance between focusing on your schedule and giving yourself enough time to achieve your goal without letting it take over every corner of your mind.

Getting big daily mileage on trails like the AT means getting up early in the morning, hiking in the dark, and hiking all day until it gets dark again.

3. Maintain such a poor diet on the road

I will say that I ate pretty well last year on my CYTC attempt, all things considered. Because I maintained higher daily mileage, I was able to go into cities much more frequently to resupply and also eat restaurant food. Thanks to this, I think I was able to maintain as healthy a weight as possible throughout the year.

All the “real” food in the city was definitely one of the things that made my diet on the road sustainable. At the beginning of the year, I made dinner at Mountain House every night to make sure I was getting a little more protein and nutrients. But over time, I got so tired that I only ate snacks throughout the day and also ate snacks for dinner.

Obviously, the strategy I was using worked well, because for the most part I avoided injuries all year. Overall, I felt strong and energized throughout my days. But outside of restaurant meals, my diet consisted exclusively of snacks and junk food. I was able to get slightly healthier junk food at larger grocery stores, but most of the time I bought my groceries for the next few days at a gas station.

For me, I think my only regret about eating a poor diet is more my curiosity about what my body could have done if I had fueled it properly. If I’m able to operate at such a high level while eating a surprisingly small amount of protein and working primarily on sugar, fat, and carbohydrates, then imagine what I could do if I fed myself what my body really wants and needs. That’s something that’s been on my mind a lot since completing my CYTC hike.

My diet during my 2025 CYTC walk was full of junk food and fast calories. Sure, I felt great and managed to keep the momentum going and walk big miles for an entire year. But I have wondered how my experience would have been different if I had focused more on nutrition.

4. Forget to be humble

Stay humble or you will be humiliated.

When I first embarked on the CYTC in 2025, I was sure it was going to be the hardest thing I could imagine doing. I had previously walked 30 miles a day for months, but I couldn’t even imagine the cumulative toll it would take to do it every day for an entire year, no matter what weather I encountered.

However, what ended up surprising me was how easy the whole process actually felt. At first, I remember joking that it really wasn’t that bad. Doing 30 kilometers a day became a routine, and with good weather and easy terrain that still left time in the day to rest well.

Of course, as time went on there would be many more obstacles along the way. But I just remember thinking that the first few thousand miles of the year were easier than I ever imagined. I think a part of me really started to believe that it wasn’t that bad and that I had it all under control.

In the end, I’m glad I had those thoughts, because the miles ahead would humble me more than I ever imagined. And after coming out the other side, overall I’m grateful for the entire experience.

When you feel good, walk strong, and go on a great run, it can be easy to get caught up in feeling like a superhero. You literally go further and faster than everyone around you, and it usually ends up being a topic of conversation with strangers who are curious about what you’re doing.

However, over time I tried to insist on the fact that there will always be easier times and more difficult times; It can be easy to forget when things are going well. Even if you are doing something that almost no one has done before, there will probably be someone who does it faster than you or who goes further than you. I have really come to try to have a greater respect for the path, its challenges and those who are suffering from all of this.

When you’re doing a big hike day after day, it can be easy to get caught up in a hike and take the little things for granted. Like your body, which does everything it can to keep you in the game. My experience at CYTC was humbling in the most beautiful way and I am continually grateful for that.

5. Foster a more human connection along the way

I know it really wasn’t practical most of the time, but I often think about how I wish I could have spent more time with all the wonderful people I met last year. I met so many strangers in the cities, got trouble and support, and met so many wonderful hikers along my trip.

Every now and then I had time to sit down and eat, hang out and talk for a while, or walk with someone for a few hours or even a few days. I spent hours traveling by car with kind new friends who offered to drive me from place to place to help me navigate the trail.

In many ways, my year was one of loneliness, but at the same time, I truly feel like the trail gave me exactly as much human interaction as I needed to get by. In a sense, my cup was always full. However, I wish I had slowed down from time to time and taken the time to really enjoy those human moments.

The times when I hung out with other hikers, shared a meal, or logged miles together were some of my favorites of the entire year. I have very fond memories of hiking the PCT with a couple of guys around the close of the Wrightwood Fire. And then doing the section before Burney Falls with some guys who were great to talk to. I even hiked for almost a week with Taco, a hiker I ran into in southern Maine on the AT.

Moments like that are priceless and helped me in ways I could barely understand. I really don’t know how much slower I could have gone and still achieved my goal, but in some ways I look back and wish I had more time for the people along the way.

Taking 17 consecutive days off due to injury during the CYTC was an incredibly stressful time. But in retrospect, being able to spend a few weeks of my year at Shaw’s Hiker Hostel was truly one of the highlights. My body needed to heal, and the connections I made there fueled me for the next stage of my journey, which involved arduous hiking and averaging more than 35 miles a day for months.