I quit my job last December to hike the the entire 2189.1 mile Appalachian Trail. On July 4th, 2016, I completed my goal and summited Katahdin after 4 months and 6 days. The journey changed my life. My takeaways are many, ranging from the mundane (e.g. food dramatically impacts your mood, ability to hike, and ability to think) to the more nuanced (e.g. my purpose is to maximize my happiness). Read about my initial takeaways here. Above all, I learned self confidence.


Washington Summit - Learning Self Confidence

80% of thru hikers quit hiking the AT. Hikers wake up each day and walk, regardless of terrain, weather, or other non-trivial factors. The daily grind is both physically and mentally taxing. The monotony challenged me the most. Trees look similar, whether they are the first or the thousandth . Eventually I would find a picturesque setting to snap a quick photo, but I would hike hours to find it. I did not have a seriously social hike, I hiked ~60% of the trail alone and rarely listened to music.

I hiked the AT because I wanted self confidence.

The difficulty inspired me to hike. 80% of hikers might not be able to finish, but I knew I could. The AT would evaluate my level of grit and show me whether I could accomplish my larger goals. I wanted the self confidence to pursue my own goals. Society has a typical success trajectory; I wanted to feel comfortable pursuing my own.

Before the AT, I did have confidence. I graduated from Dartmouth and went to work at a PE consulting firm in Boston. On the outside my choices were typical and successful. They were easy. I have been privileged with a great education and an amazing support network. At each junction, I took the typically successful path because I thought that was expected of me. While I had self confidence, I did not have the self confidence that comes from making choices at odds with society’s expectations. I hadn’t learned real self confidence, because I relied on society to guide my decisions.


Then in 2015, I started an email gratitude journal. If happiness is my end goal, gratitude journals are frequently the means. Gratitude journals are scientifically proven to increase happiness. I wanted to use these findings to to spread happiness among my friends. Though it sputtered out after a few months, this project exposed me to a wealth of happiness research as I searched content for subscribers.

Gratitude Journals are Good

These resources hammered home that true happiness comes from within, society’s expectations be damned.

I started looking for atypical success trajectories that more closely aligned with my interests. During my email gratitude journal phase, a friend and I went on a hike. Somehow the Appalachian Trail came up and we decided to hike the following year. I decided to hike for many reasons. They changed as I got closer to my departure date, and they changed during the hike itself.

Through these changes, one theme stayed constant, self confidence. I wanted to learn real self confidence and feel comfortable following my own ideals of success. In order to learn this self confidence, I knew I needed to finish the Appalachian Trail. Quitting would ruin any semblance of independence I hoped to cultivate.

For the past 7 years, I worked on 5 separate projects that I hoped would flourish to something much larger. They all failed. I made easy excuses for the failure; I needed to graduate college, or I had a well paying job. During each project, I had been obsessed with the final outcome, with little thought about the grit required to get to that outcome. The AT would be different. I couldn’t fail in a goal like the AT because I knew the consequences of failure. I had quit my job, and I told everyone my goal. Quitting would ruin my self confidence and I would never be able to start a successful venture.

So I embarked on the Appalachian Trail and a little over four months later, I finished. I hiked the trail fast because I liked the challenge and I would not give myself excuses to be lazy.

If I have the mental strength to walk 18 miles every day, regardless of weather and terrain, I know I can start something that is lasting.

I learned self confidence through finishing. Having completed one large goal, I have a more realistic expectation of the barriers that it takes to finish something great. Grit is the key, and I know I have it. The end goal is not accomplished overnight. It takes daily effort. I would not have made it to Katahdin had I thought about the thousands of miles I had yet to hike. I know I can create similar daily routines for my next projects.

My next goals will be more difficult. I hope to expand this blog, establish a location independent lifestyle, and grow my gratitude journal. I have less of a blueprint to success, because I can’t simply wake up, eat food, and walk.

My self confidence is still a work in progress. I don’t know exactly how I will succeed, but I feel confident that I can figure it out. I am excited to explore the world and work on my ventures, because I know that is what makes me happy, and that is all that matters right now.


  • Prior to my Appalachian Trail thru hike, I conformed to society’s rules of success and had little self confidence to embark on my own.
  • True happiness comes from within and society shouldn’t dictate happiness or success.
  • On the AT, I gained self confidence and know I can choose my own path to success.
  • While I don’t have a clear blueprint for my next ventures, the grit I learned will prove invaluable to my future goals.

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