When I decided to hike the Appalachian Trail, I did my share of reading. Of the books I read, Appalachian Trials: A Psychological and Emotional Guide To Thru-Hike the Appalachian Trail (Volume 1)* prepared me the best. It advocated for strong mental preparation prior to embarking on the Appalachian Trail. One strategy on goal-setting helped me in particular. I took a sheet of paper and divided it into three categories: Why are you hiking the Appalachian Trail? What will you get if you complete the Appalachian Trail? What will you lose if you quit the Appalachian Trail? I brainstormed answers for a while.

Mental Preparation Piece of Paper

If I were to quit my job, I must know exactly why I was hiking.

This mental preparation helped me finish the trail because I knew why I was hiking, what I would get out of it, and the implications of quitting. When answering these questions, I could not lie to myself or I risked defeating the purpose of this preparation. After brainstorming, I committed myself to the answers. I wrote them on a piece of paper, along with a few choice inspirational quotes, laminated it, and put it in my AT journal. This paper served as a reminder of my motivations and as an inspirational tool during tough times. I never needed to reference my paper, but I valued it above all my gear. Money couldn’t buy it.

Why did I hike the Appalachian Trail?

Snow on the AT

I wanted to live simply outside. [Accomplished]

Prior to my hike, I believed my life complex. I rarely took a step back. Work filled my days. Living outside for a couple of months interested me as a period of enforced solitude in which I could reflect. In Boston, I rarely experienced the outdoors like I did at Dartmouth. Living outdoors could strip society’s complexity. Thoreau’s classic quote resonated with me.

 “I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.” – Thoreau

I want to outline a manifesto for my life. What matters to me? Why? [Failed]

Creating a manifesto on the trail seemed an excellent idea. I had already spent significant time writing down my thoughts on life, morality, and religion. Spending hours hiking could declutter society’s detritus riddling my brain. A manifesto never came out of the trail. I learned the wilderness can be just as distracting as society.

I want to eliminate my privileged safety net. [Accomplished]

I am a white male, Ivy League graduate who consulted for private equity firms. I am privileged. When I stepped onto Springer, this privilege lessened. I was still lucky to have the time, finances, and physical ability. But having privilege didn’t make walking any easier, and I did not finish because of it. On the trail, I was simply “Stuck,” the ginger bearded, no mustached, man from NJ.

I want to eliminate external validation. [Accomplished (Sort-of)]

Let’s be clear, I told everyone and their mother about the Appalachian Trail. I would shame myself into finishing. Finishing is a status symbol, but hiking let me sidestep the traditional forms of validation, such as wealth, career, and education. These factors play only a limited role in one’s happiness. So why do people care so much? By going into the woods, I escaped these status symbols.

I want to meet new people and be self-sufficient. [Accomplished]

I have a strong group of friends, most of whom moved to either New York or Boston after graduation. We were highly educated North Easterners. Hiking the trail would expose me to many different types of people I had little exposure to. It was true, on the trail I met many former military and many religious people. Both these populations I interacted with rarely at Dartmouth and in Boston. Interacting with different people helps me better understand others’ perspective. I also wanted to be self-sufficient. I had read Emerson’s “Self-Reliance” and appreciated the power he bestows on individuality. While always an individual, I wanted to more fully live on my own terms.

I want change. [Accomplished]

I felt comfortable at my job and had a great group of friends. I knew I needed to change things up to increase the rate at which I was learning. Hiking the Appalachian Trail would teach me things that were way outside of my comfort zone. For one, hitchhiking. By experiencing discomfort in new life situations, I could force personal growth. After answering, why I was hiking the trail, I next answered “What will I get if I complete the trail?” These answers were similar in nature, but required that I reach Katahdin to accomplish them.

What will I get if I complete the trail?

Katahdin Summit

I can overcome any challenge. [Accomplished]

Finishing the trail required flexibility. If I can survive outside for 2200 miles, I could overcome society’s first world challenges.

I will be a doer. [Accomplished]

Millennials talk a lot. I know I do. “How cool would it be if I do X or Y?” Few people follow through with their musings. Life gets in the way, and I realize that. But I did not want to be a talker. When I said I was going to hike the trail, I made sure that I would. Friends, family, and acquaintances would know when I say I will do something, I will.

My purpose will be clearer. [Failed]

I figured I would reach Katahdin with all life’s answers. I would strip away all my superficiality and emerge new and pure. This obviously didn’t happen. Spending so much time in my head just confused me more. Additional life trajectories I had never pondered sprung up as legitimate next steps.

I will experience novelty, and I will be different. [Accomplished]

I equate novel experiences with personal growth. I live one life so I might as well try new things. Difference shows agency in pursuing personal growth. Looking back, the reasons I hiked the trail and what I would get if I completed the trail were similar. These first two questions helped me understand my motivations. Yet, I found answering the next question, “What will happen if I quit?” the most impactful. Instead of looking at the AT positively, the question evaluated the negative implications of quitting. Had I stopped and only answered the first two questions, I could have justified quitting mid-hike by deluding myself that I had accomplished my goals. By looking at the act of quitting itself, I disallowed myself from mid-hike delusions.

What will happen if I quit?

Grey Stones

Everyone will know.

If I were to quit everyone would know, because I told them my hiking plans. Had I quit, I would always wonder if people treated me differently. I could not have that.

I will be a quitter.

My brother wrote the following searing Instagram post on the day I quit my job.

“I believe we all have the capacity to do great things in life. Some people have to wait until they are older to achieve these great things but in rare instances, someone models greatness every single moment of their life. Ginge, from day one you have been a quitter and I’ve always looked up to you for it. Whether it was the time you wanted to be a Navy SEAL and then realized what that actually entails, the time you bought Rosetta stone to learn Italian and then got bored, the times you stopped the viola or the piano or soccer, or any number of passions you once had, you have quit everything you ever started in life and I am so proud of you. You inspire me every day and I think the world should hear your story – you could write a book about it but I guess it wouldn’t ever get finished. Here’s to another thing you’ve quit [my job] and here’s to quitting your next big undertaking.”

Though I knew he wrote in jest, I hated it. And it was true, I had quit a lot of things before. But I envision myself as a Navy SEAL, and I’m pretty sure I made at least a couple of right decisions. I did not want to be a quitter. I wrote down my brother’s post as part of the supplementary content on my laminated paper. It reminded me about the consequences of quitting.

I will lose confidence. I will not change the world.

I believe that I can change the world. Yes, I have an ego, but I try to keep it in check. I knew quitting limited my ambition because who can change the world that can’t walk for a couple months?

I will be a talker.

Instead of a doer, everyone will know that I am a talker. Others can’t trust me to follow through.

I will waste 5 months and a promising career trajectory.

I am crafting a personal narrative. An Appalachian Trail thru hike is easy to include in this narrative. 20-something searches for meaning. Easy. Quitting is not part of that narrative. How do I tell friends, family, employers, and investors that I quit. I can’t leverage my trip, in fact, it’s a net negative.

I will never be able to look at myself. I will always think “what if?”

Life is a bunch of tradeoffs. Each decision impacts another. Had I not finished, I would always wonder if my life would have been better. I knew my thoughts would follow the path of “I didn’t get the job because I quit,” “my relationships deteriorated because I’m a quitter.”

All my conclusions seem absurd in hindsight, but I did this purposely. The ante was so high that I had to finish. I carried this piece of laminated paper with all my mental preparation throughout the hike. It was my most valuable piece of gear. After so much time thinking, writing, and finding material for it, I actually referenced it rarely.

My mental preparation gave me a positive mindset.

By escalating the consequences of quitting so high, the thought never crossed my mind. Extensive mental preparation can do wonders for accomplishing goals. It helped me evaluate my hike and make sure I had the motivation. I will use this framework for future large goals as I credit it with helping me finish.

As I mentioned earlier, I included supplemental inspirational quotes on this piece of paper. They are below.

Inspirational Quotes I Carried

Inspirational Sunrise from Wildcat

If  (Rudyard Kipling)

If you can keep your head when all about you
Are losing theirs and blaming it on you,
If you can trust yourself when all men doubt you,
But make allowance for their doubting too;
If you can wait and not be tired by waiting,
Or being lied about, don’t deal in lies,
Or being hated, don’t give way to hating,
And yet don’t look too good, nor talk too wise:

If you can dream—and not make dreams your master;
If you can think—and not make thoughts your aim;
If you can meet with Triumph and Disaster
And treat those two impostors just the same;
If you can bear to hear the truth you’ve spoken
Twisted by knaves to make a trap for fools,
Or watch the things you gave your life to, broken,
And stoop and build ’em up with worn-out tools:

If you can make one heap of all your winnings
And risk it on one turn of pitch-and-toss,
And lose, and start again at your beginnings
And never breathe a word about your loss;
If you can force your heart and nerve and sinew
To serve your turn long after they are gone,
And so hold on when there is nothing in you
Except the Will which says to them: ‘Hold on!’

If you can talk with crowds and keep your virtue,
Or walk with Kings—nor lose the common touch,
If neither foes nor loving friends can hurt you,
If all men count with you, but none too much;
If you can fill the unforgiving minute
With sixty seconds’ worth of distance run,
Yours is the Earth and everything that’s in it,
And—which is more—you’ll be a Man, my son!

On Providence (Seneca)

“For experience is necessary to get a knowledge of one’s self. No man has learned his powers except by trial. Therefore some men have voluntarily exposed themselves to misfortunes which were passing them by and sought an opportunity for their virtue- about to pass into obscurity – to distinguish itself. Great men, I say, rejoice at times in adversities, just as brave soldiers do in war.”

On the Happy Life (Seneca)

“What is the happy life? It is peace of mind, and lasting tranquility. This will be yours if you possess greatness of soul; it will be yours if you possess the steadfastness that regularly clings to a good judgment just reached. How does a man reach this condition? By gaining a complete view of truth, by maintain in all that he does, order, measure, fitness, and a will that is inoffensive and kindles, that is intent upon reason and never departs therefrom, that commands at the same time love and admiration.”


Song of Myself  (Walt Whitman)

1. I Celebrate myself, and sing myself,
And what I assume you shall assume,
For every atom belonging to me as good belongs to you.

I loafe and invite my soul,
I lean and loafe at my ease observing a spear of summer grass.

My tongue, every atom of my blood, form’d from this soil, this air,
Born here of parents born here from parents the same, and their parents the same,
I, now thirty-seven years old in perfect health begin,
Hoping to cease not till death.

Creeds and schools in abeyance,
Retiring back a while sufficed at what they are, but never forgotten,
I harbor for good or bad, I permit to speak at every hazard,
Nature without check with original energy.
I have said that the soul is not more than the body,
And I have said that the body is not more than the soul,
And nothing, not God, is greater to one than one’s self is,
And whoever walks a furlong without sympathy walks to his own funeral drest in his shroud,
And I or you pocketless of a dime may purchase the pick of the earth,

And to glance with an eye or show a bean in its pod confounds the learning of all times,
And there is no trade or employment but the young man following it may become a hero,
And there is no object so soft but it makes a hub for the wheel’d universe,
And I say to any man or woman, Let your soul stand cool and composed before a million universes.
And I say to mankind, Be not curious about God,
For I who am curious about each am not curious about God,
(No array of terms can say how much I am at peace about God and about death.)
I hear and behold God in every object, yet understand God not in the least,
Nor do I understand who there can be more wonderful than myself.
Why should I wish to see God better than this day?
I see something of God each hour of the twenty-four, and each moment then,
In the faces of men and women I see God, and in my own face in the glass,
I find letters from God dropt in the street, and every one is sign’d by God’s name,
And I leave them where they are, for I know that wheresoe’er I go,
Others will punctually come for ever and ever.

Litany Against Fear (Dune, by Frank Herbert)

I must not fear.
Fear is the mind killer.
Fear is the little death that brings total obliteration.
I will face my fear.
I will permit it to pass over and through me.
And when it is past gone I will turn the inner eye to see its path.
Where the fear has gone there will be nothing.
Only I will remain.


Self Reliance (Emerson)

“To believe your own thought, to believe that what is true for you in your private heart is true for all men, that is genius.”

“The power which resides in him is new in nature, and name but he knows what that is which he can do, nor does he know until he has tried.”

“Nothing is at last sacred but the integrity of your own mind.”

“No law can be sacred to me but that of my nature. Good and bad are but names readily transferable to that or this; the only right is what is after my constitution, the only wrong what is against it.”

“But men postpones or remembers; he does not live in the present, but with reverted eye laments the past, or heedless of the riches that surround him, stands on tiptoe to foresee the future. He cannot be happy and strong until he too lives with nature in the present, about him.”

“Let a stoic open the resources of man, and tell men they are not leaning willows, but can and must detach themselves that with the exercise of self-truist new powers shall appear, that a man is the word made flesh, born to shed healing to the nations that he should be ashamed of our compassion, and that the moment he acts from himself, tossing the laws, the books, idolatries, and customs out of the window, we pity him no more, but thank and revere him – and that teacher shall restore the life of man to splendor, and make his name dear to all history.”


  • I asked myself “Why am I hiking the Appalachian Trail?” “What will I get if I complete the Appalachian Trail?” and “What will happen if I quit?” as a form of mental preparation.
  • My answers to “why I hiked” and “what I would get if I completed the Appalachian Trail” were similar. I hoped to live simply and gain confidence through self-sufficiency.
  • I escalated the consequences when I answered “what happens if I were to quit.” Knowing other people would identify me as a quitter was a powerful motivator.
  • I wrote down my answers along with inspirational quotes on a piece of paper and carried this during my hike.
  • Through extensive mental preparation, I retained a positive perspective.

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