Tools to Create Healthy Habits

If happiness is the goal, habits are the means. Habits are systems to nurture your mind and body. I cannot will myself to be happy. However, by creating healthy habits, I leverage the subconscious influence of my environment to enhance my wellbeing. Below I break down a couple important considerations that I use when I create a habit.

It takes 66 days to create a full habit on average.

I break down my habits into smaller bite size pieces. 66 days can seem long. If I wanted to start a meditation practice today (everyone should meditate), my first goal is to meditate today. I make habits manageable by decreasing the time frame. The 66-day mark is too far away. I need to meditate today and make sure I meditate tomorrow. Soon I will have meditated for a week. The 66 days becomes 59 days. If I can meditate for a week, then I can meditate for the next week. Adding up a couple weeks together, and I have meditated for a month. I’m halfway through creating a healthy habit. By breaking down my goals, I can establish long term habits.

Habits are best created when started at the beginning of a new experience.

It is called the Fresh Start Effect. When a new week starts, I have the mindset that I am a new person from the last week. The imperfections of my previous habits are erased at the start of a week. The fresh start effect can be applied to weeks, months, and years. We create New Year resolutions and goals for habits after a birthday. Beyond these temporal landmarks, new locations can create fresh start effects as well. When I moved to SF, I engaged in many new behaviors. I’ve been running, meditating, writing, and journaling every day since I moved.

Streaking is a good thing.

Streaking does not have to do with nudity. It means performing a task every day and not breaking the streak. Humans are loss averse, and would rather not lose something than gain a reward. Breaking a streak is a powerful negative motivator that uses loss aversion to strengthen habits. I stopped drinking for 8 months to prepare for the Appalachian Trail. Not drinking was easy. I could justify to myself that I hadn’t drank for months, so I wasn’t going to then. After the trail, I was hesitant to break my non-drinking streak because I knew recreating the streak would be difficult.

My dad has created an excellent habit of running by streaking. He runs every day and has been running every day since July 2014. He started by creating a goal to run every day of July. He expanded that goal to run every day since. Even when it is cold, wet, and gross out, he runs. Even when injured, he runs. His impressive history motivates him to continue.

Sometimes streaking can feel like cheating. I’d like to know I have the mental fortitude to start a habit at will. However, habits are difficult to form. If streaking is the only way to keep a habit, it’s a great tool. I would rather rely on streaking as a method than limit the habits that I create.

Limit barriers.

Our subconscious would love to sit on a couch, eat fried food, and watch Netflix. If I want to change how I act I must make it super easy. I have to actively work against my subconscious. To start a habit, I must make it insanely easy to perform the action.

I set out my clothes to run the night before so that I don’t look for them in the morning. I put my journal next to my bed so I can easily journal when I go to sleep. If I want to eat healthy, I need to have a fully stocked fridge of healthy items. When I browse for food, the healthy options are immediately apparent. Every small barrier to goal completion reduces the likelihood I complete a task. By identifying and eliminating barriers, I can more easily accomplish my tasks.

Start Small.

I came off the Appalachian Trail thinking I would make a daily habit of running 10 miles a day. For a thru hiker, this didn’t seem absurd. Only an hour and a half a day of exercise paled in comparison to my previous exercise levels. I never created this habit; I couldn’t run for the first month after my trip. My knees hurt too much, and I thought I’d give myself a rest. Running 10 miles a day seems excessive now.

I could try to run 10 miles a day, but creating that habit from scratch is difficult. I might be able to run that much for a couple days in the row, but eventually I would lose motivation. Motivation will ebb and flow, but systems stick. By creating a system where I run at least a mile a day in the morning, I can create healthy habits. Small goals can add up to significant achievements. Setting manageable expectations is important because happiness is the difference between expectations and reality.

I create habits to subconsciously impact my happiness levels.

I rely on starting with small accomplishable goals to create long-term habits.

Letting Go of Summer

Summer is like happiness. Both are fleeting and appreciated most in their absence. Sometimes I wish I could stay in summer and not face reality. “Where will I be? What should I do?” Living with these questions unanswered takes a toll. I feel directionless and stressed, but I know I must let go and search for new experiences.

Summer is special because it is different. I can relax because I know summer is not forever. If I wanted to, I could continue living as I did in summer. At least for a while. I don’t need to answer all these life questions immediately. I could sit on a couch for a week or two. But even if I could escape reality for a little longer, I wouldn’t. I value summer because it coincides with my friends’ summers. We can relax and be carefree together.

Fall changes our shared experience. People go back to school or work. Sitting around doing nothing might be joyful when accompanied by others, but I know it is not joyful alone. Even though I do not have work requirements, I still feel real life’s presence because experiences are valuable when shared.

To be happy, I must embrace fall’s catalyst for change.  Change pushes me to new experiences, even better than the last. I loved college, but by leaving I could hike the AT, a new and equally significant life experience. By letting go of an experience I recognize its significance. This week I let go of my beard, shaving for the first time since February. I didn’t know how I would look clean shaven, but I needed to see. More importantly, I needed to bring closure to my AT experience. I shaved because I am excited about new and better things. To further adventure, I must let go of my old adventures. Shaving symbolized my transition.

It was still uncomfortable. Letting go usually is. I have to confront uncertainty. “What is in store for me now? How will I remember?” Letting go forces closure, when the closure might not be easy.

But closure opens doors. I am not beholden to past experiences. I can live fully in the present. After an incredible summer and Appalachian Trail journey, I look to the fall and see new beginnings. I am living in San Francisco for at least September. It’s a new city with old friends. I may end up here. Who is to say? I don’t have to make that decision yet. But I do need to let go of summer.

Mental Preparation and a Piece of Paper

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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It’s Best to Be Uncomfortable

My overall happiness levels increase when I grow. Growth and comfort are linked. When I feel comfortable I also feel like I have limited growth opportunities. I think it is best to be uncomfortable because discomfort is a clear indicator of personal growth. Embracing discomfort does not give me immediate pleasure in the short term, but I know it has serious impacts on my future happiness levels.

It is best to be uncomfortable because I do not grow when I am comfortable.

Comfort means that I understand the outcome of an event or interaction. If I understand the outcome of an event, there is no need for me to accomplish the event, because I understand its outcome. I will naturally feel uncomfortable if I don’t know how the event will unfold. If I set an expectation for myself and am not confident in performing to that level, I will feel uncomfortable. Those feelings of discomfort indicate that I am pushing myself.

Discomfort is rooted in the fear of the unknown.

I am unsure whether I will perform to the expectation I set myself and therefore I fear the result. For instance, I feel uncomfortable when public speaking because I do not know how people will perceive my performance. How will they react? Will they understand and be persuaded by my pitch? Do I come off as intelligent? However I know I will learn disproportionately more if I were to put myself on a stage than if I were not to. 

One of the most common forms of discomfort is when interacting with others. We frequently feel uncomfortable because it can be difficult to understand other’s reactions. Do people like interacting with me? Does my boss appreciate my insights? These types of questions are naturally difficult to answer when faced with interacting with new people and settings. On the flip side, we rarely feel uncomfortable around friends and family because we have such a better sense of how they will react.

Comfort is a form of settling.

When I am comfortable, I know that I am not pushing myself. I am comfortable with the people I interact with, I am comfortable with the work that I am outputting. For me that means something needs to change. I need to experience the unknown in order to grow. As an independent man with few family responsibilities, the risk of failure is relatively low. I know if I don’t take risks I limit my growth opportunities.

I hold to the mantra that I should start experiences before I feel ready. If I feel ready, then I probably could shoot for something more. If I feel ready that means I have set a bar that I know I can achieve. The outcome is known to me. By setting the bar higher and shooting for points of failure, I can grow even faster. I may not reach the bar I set, but I know I will perform above a bar that I feel comfortable setting.

Quitting my job and hiking the AT is the most significantly uncomfortable event that I have experienced.

I told everyone I was hiking the AT. I’d hiked a max of 70 miles in a row previously. 2200 is a completely different ball game. I was not ready to quit my job when I did, but I knew it was best to be uncomfortable. I knew I feared the unknown. By setting such a high bar for myself I grew tremendously in a short 4 months. Read about some of my takeaways here: Appalachian Trail Takeaways Part 1.

My next adventure is to travel and write the Happyness Journal blog. I don’t know whether I can sustain myself or how I am going to make ends meet.

Best to Be Uncomfortable - Appalachian Trail Image

I could find a new full time job, and I may still look for one. Full time employment is tantalizing because it is comfortable. I know that if I must apply to a full time job, I need to feel uncomfortable in that space. I lose growth from my incredible AT experience if I settle with full time employment in a known space. Because it is best to be uncomfortable, I’ve decided to push myself and grow and try out new life choices.


  • It is best to be uncomfortable because discomfort indicates growth experiences.
  • Comfort indicates limited growth.
  • I feel uncomfortable when I start experiences before I am ready, but I know that is a good thing for me.
  • I feel uncomfortable with the trajectory of the Happyness Journal and that excites me.

Gratitude is Good

How do we achieve happiness? I could list banal platitudes that humans have repeatedly vocalized. These remarks are so individualized and anecdotal that they minimize their impact. However the growth of positive psychology can redefine our perception of happiness by scientifically understanding the sources of pleasure and meaning in our lives. One concrete takeaway from the positive psychology field is that gratitude is good.

People that practice gratitude regularly experience significant physical and mental benefits.

They have stronger immune systems with lower blood pressure, higher levels of positive emotions, more joy, and optimism. They act more generously and compassionately, and feel less lonely and isolated. In terms of gratitude, the science is clear; by focusing on the positive, people can train their brains to think happier and more positively.

Gratitude is good, and it is so easy.

Think about three things for which you are grateful. Write them anywhere. The ideas do not need to be fully fleshed out. Events can be simplified to a single placeholder word. An amazing afternoon of swimming at the beach could be conveyed through the single word “ocean.” There is no time requirement for gratitude. 15 minutes of grateful reflection are just as significant as two. By taking the time, however short, to be grateful, baseline levels increase happiness. Writing isn’t even a requirement for living a grateful life; it is, however, a good way to create a habit and look back at previous happy moments.

Gratitude Is Good - Gratitude Journal

My future self thanks me when I write my grateful moments down in detail. Though I can experience gratitude with a single word such as “ocean,” years from now this word has little meaning. Longer journal entries provide context and nuance to my gratitude. Additionally, by attending to the moment that makes me grateful, I can better remember it.

I like using a small journal that can fit in my pocket to carry throughout the day. My notebook is both a place to ideate and journal. I do not prefer ruled paper as it confines me to write linearly. Brainstorming with unruled or graph paper is much easier. Journals such as Shinola and Moleskine are perfect for my needs. They fit in your pocket, have a good paper quality, and are durable. Carrying a journal throughout the day reminds me that gratitude is good.

Gratitude is a habit.

Habits can be difficult to continue after the initial excitement. Journaling can get tedious. I know I periodically stop journaling because I am tired, don’t think it will do much, or simply forget. However, when I compare my journaling self, to my non-journaling self, I recognize the difference in my happiness levels. Gratitude is good, and it works.

The best way to continue journaling is to carry a notebook around everywhere. When I actually carry the notebook in a pocket, I journal more frequently because it is just large enough to be regularly noticeable. By keeping a journal in my pocket, I also remember to put it by my bedside. If I haven’t journaled during the day, I just made it easy to be grateful right before bed. I typically try to journal before bed anyway because habits are best formed when repeated at a similar time each day. By journaling right before bed, I train myself to be grateful when I’m falling asleep.

What about mobile apps?

There are a few mobile apps  that provide some journaling functionality beyond simple text entry. The more advanced ones allow you to tag people, places, events, emotions, weather, and photos. I do not use these apps because they do not leverage technology enough to overwhelm the joy I have writing with simple pen and paper. Writing on paper is more organic.

I do believe that journaling on mobile platforms is coming, and I believe that data driven journaling will move people to journal mobily. is a good example of an early stage data driven writing tool. It provides limited emotional feedback while keeping stats on your writing habits. Mobile is the next frontier for journaling because phones have notification features and are carried everywhere. Once data entry more closely aligns to writing on unruled paper, I see little reason a person would carry both their phone and a journal.

One of my goals on my Impossible List is to create a mobile app. Because I know gratitude is good and I love journaling, I hope to use data driven journaling as my first foray into the space. Stay tuned.


  • Gratitude is good. Science proves it increases your happiness.
  • Gratitude is easy. It can take as little as two minutes a day to cultivate gratitude.
  • Journals such as Shinola and Moleskine are great tools to start a journaling habit.
  • Journaling apps exist, but none that are better than pen and paper to me.

Intro to the Happyness Journal

I am starting a blog called the Happyness Journal.

The name refers to the gratitude journal I experimented with in 2015. The blog will focus on the four categories core to my approach to personal fulfillment: travel, minimalism, mindfulness, and happiness. The blog commits me to writing, teaching, and learning about these topics. If at a minimum the blog makes me write, I will be happy.

I will write one to two blog posts a week. Email is sacred. Subscribers trust me with a direct line to their inbox. I will not abuse this trust and so will limit my contact to one or two emails a week. These emails will include my blog posts and additional content from across the internet that I find particularly noteworthy or educational.

I want to create an engaged community.

Travel, minimalism, mindfulness, and happiness are powerful ideas. I want to form a large and engaged audience made up of friends, family, and others interested in these topics. This community could teach me many things.

I want subscribers engaged. What posts work and what don’t? What content areas am I missing? How should my writing style change to facilitate my message?  I am active on email and will respond promptly to all feedback.

Content is king.

All content I send must answer “yes” to the following questions: 1) Does the post/content make me think? 2) Does the post/content have actionable strategies to enhance living? 3) Is the post/content interesting? I will not share content that is not revelatory. Content will focus on the four pillars: travel, minimalism, mindfulness, and happiness. Post types will vary and will include but are not limited to: experience overviews, thought pieces, product guides, and city highlights.

I do not expect profit from the Happyness Journal.

The blog lets me create an engaged community while exploring intriguing ideas. There will be no overt ads anywhere on the site. When evangelizing about a product I love, I may use affiliate links, but I will let you know when I do.

While not working on the Happyness Journal, I work on startups aligned with my four pillars.

Working on startups is my career path of choice. I am currently working on pitching investors / working on an MVP for a quantified self startup. If you are interested in talking startups, please email me.

Email me.

Seriously – I will respond promptly to any questions / concerns / compliments.

Please send this to people you think might be interested.

I want to grow the Happyness Journal community beyond people that I know intimately. If you know anyone interested in a weekly blog on travel, minimalism, mindfulness, and happiness, please forward this to them.

Thank you.

Access a treasure trove of happiness content!

- The subscriber only resource section has over 50 articles and videos focused on happiness!

- Receive weekly updates on themes such as mindfulness, minimalism, and travel.

Check your email to confirm! Welcome to the Happyness Journal!