in: Behavior, Character, Featured

• Last updated: June 3, 2021

31 Journaling Prompts for Building Greater Self-Reliance

Poster about 31 days to greater self-reliance by Art of Manliness.

Editor’s note: This is a guest article by Kyle Eschenroeder, author of The Pocket Guide to Self-Reliance.

“The writer is an explorer. Every step is an advance into a new land.” ―Ralph Waldo Emerson

The goal of self-reliance is to achieve sovereignty in our connected, civilized world. It’s to remember that your judgments are valid — even if, especially if, they’re unpopular. It’s remembering you don’t need to be on a side, that the team colors people try to throw on you may not actually represent who you are.

There’s no magic bullet for self-reliance. There’s no step-by-step system to achieve it. There are, however, some practices that will help us move towards it. I, along with countless others, have found journaling to be a particularly effective one.

Below you’ll find 31 journaling prompts designed to help nudge you toward self-reliance. They’ll help you think about and articulate pieces of yourself you might not have considered before — at least not explicitly. They’ll help you recognize your beliefs and find areas where you’re not sure what you believe. They’ll help you think about situations you’re in and decisions you’re making and what to do about them. In general, they’ll just help you look in the right direction.

The aim is to help you go deeper into yourself so that you might better reset your relationships to yourself, the world, and the people you spend time with.

I’d recommend writing on each prompt for at least twenty minutes. It’s likely that these will serve as jumping-off points and you’ll end your writing session on a completely different topic having followed your ideas on an open-ended — and self-reliant — course.

You can start working on these prompts at any time, and do as many a day as you’d like (though I don’t recommend tackling more than two a day, to make sure you give each sufficient space and time for reflection). However, the number of prompts — 31 — makes them particularly suitable for tackling one a day as part of a month-long exercise. Commit to making the 31 days ahead the month where you finally begin to live a life in which you make decisions with primary respect to your own experience of the world. When you finally begin to pay less attention to the opinions of others, and start really being true to yourself. When you finally start trusting yourself.

Day 1

“The primary cause of disorder in ourselves is the seeking of reality promised by another.” ―Jiddu Krishnamurti

What is something you have or are pursuing, that other people say is worthwhile, but you haven’t found valuable? Do you continue to pursue it based on the promises of others?

Day 2

“The virtue in most request is conformity.” ―Emerson

“People say that what we’re all seeking is a meaning for life. I don’t think that’s what we’re really seeking. I think that what we’re seeking is an experience of being alive, so that our life experiences on the purely physical plane will have resonances with our own innermost being and reality, so that we actually feel the rapture of being alive.” ―Joseph Campbell

Where do you find the most meaning in life and feel the most fully alive? Is there something you’d love to do but don’t because the world thinks it’s silly or worthless or wrong? Is there anything you do that you consider virtuous yet the world looks down on? How do you handle the tension?

Day 3

“I would write on the lintels of the doorpost, Whim. I hope it is somewhat better than whim at last, but we cannot spend the day in explanation.” ―Emerson

If we don’t trust our whims to guide our exploration of possibilities for our lives, we’ll quickly find ourselves relying on others for answers.

What areas of your life have you shut off to whims? Are there any you’ve written off? How might you try following them responsibly? (Is it writing an outline for a ridiculous-sounding blog post? Picking up that book that feels “unproductive”? Joining the boxing gym you pass daily? Asking that girl out you’ve had your eye on? Booking the trip you’ve been thinking about?)

Day 4

“The objection to conforming to usages that have become dead to you is, that it scatters your force.” ―Emerson

What pieces of your old identity do you hold onto that are no longer serving you or you no longer believe in wholeheartedly? Are they worth letting go of?

Day 5

To compete is to choose to play somebody else’s game. This can be a massive source of energy, but it’s also a dangerous game. The billionaire investor and founder of PayPal, Peter Thiel, said that the fierce competition in his college career nearly kept him from doing what he actually was meant to do. He later wrote in Zero to One, “All failed companies are the same: they failed to escape competition.”

When we’re locked in competition we tend to obsess on doing the same thing but faster, bigger, or cheaper. Competition can blind us to opportunities to truly distinguish ourselves.

In fact, the fiercer the competition, the more similar things get. Harvard Professor Youngme Moon writes in her book Different: Escaping the Competitive Herd that, “The dynamic [of competition] is not unlike a popularity contest in which everyone tries to win by being equal parts friendly, happy, active, and fun. Or an election campaign in which all the candidates try to be charming, serious, humble, and strong. Once everyone starts doing it, no one stands out.”

Put simply, Moon has found that, “The more diligently firms compete with each other, the less differentiated they can become.”

Even more often than businesses, individual lives are ruined by being too preoccupied with competition to look around. Where are you competing in your life that you don’t actually want to be (e.g., money, audience, position, possessions, looks, awards, travel, experiences etc.)? If you weren’t worried about winning that, what would you focus on?

Day 6

“These are the voices which we hear in solitude, but they grow faint and inaudible as we enter into the world.” ―Emerson

Self-reliance often means following our quiet, inner voice more faithfully. It means not just listening to what we say, or even to what we think, but paying more attention to what usually lies beneath our consciousness. Picasso himself knew that what he wanted to express wasn’t his own idea:

“To know what you’re going to draw, you have to begin drawing. . . . When I find myself facing a blank page, that’s always going through my head. What I capture in spite of myself interests me more than my own ideas.”

Picasso wasn’t aiming to express his ideas but ideas that seemed to be beyond him. He understood that self-reliance wasn’t about absolute control and knowing the answer ahead of time, but diving into the unknown and trusting himself to navigate.

Write about a time you listened to that inner voice, then a time you ignored it. How did each turn out? How did the conversations with your inner voice differ? How can you become better attuned to those subtle nudgings?

Day 7

Ultimately, we come to self-reliance by forgetting ourselves. It’s the kind of self-trust many new parents feel because they finally have this thing outside themselves that matters much more than themselves. We can access it by caring about anything properly (a project, a movement, an idea, a person, etc.).

Milton Mayeroff describes this dynamic in On Caring:

“Direction that comes from the growth of the other should not be confused with being ‘other directed,’ where this refers to the kind of conformity in which I lose touch with both myself and the other. Rather, by following the growth of the other, I am more responsive to myself, just as the musician is more in touch with himself when he is absorbed in the needs of the music.”

Ironically, no matter how physically self-reliant we become, if we never truly care for something outside of ourselves we’ll never become self-reliant.

What do you care most about? As in, what do you give yourself to most freely? How could you care for it a little more perfectly? How does caring for this thing outside yourself actually help you trust yourself more?

Day 8

“[W]e go to far less trouble about making ourselves happy than about appearing to be so.” ―La Rochefoucauld

“These are the voices which we hear in solitude, but they grow faint and inaudible as we enter into the world.” ―Emerson

Many times we want what we want for no other reason than other people want it!

Take time today to ask what you want to want. Not what you want, but what you want to want.

Some example shifts: from wanting attention to wanting to help; from wanting an easy life to wanting the struggle; from wanting fame to wanting relationships.

Not all these sets are mutually exclusive, but one usually comes at the cost of the other. If you could choose your desires, what would they be?

“It is easy in the world to live after the world’s opinion; it is easy in solitude to live after our own; but the great man is he who in the midst of the crowd keeps with perfect sweetness the independence of solitude.” ―Emerson

Day 9

Our posture toward the information we take in matters a lot.

How do you approach your nonfiction reading (offline and online)? How do you treat different authors or personalities? Are you having a conversation with the articles and books you read? Are you marking disagreements you have with them? Are you making connections between them?

Day 10

Self-reliance doesn’t demand that you make public every belief you hold. If you were to talk openly about every controversial opinion you have you’d be pressured to defend those ideas as well. For some, that could turn into a full-time job.

What are your most controversial opinions? Why do you believe them? Even if they’re not worth talking about publicly, it’s worth exploring them yourself.

Day 11

“I do not wish to expiate, but to live. My life is for itself and not a spectacle.” ―Emerson

Is your life a show you’re putting on for others? Do you use social media to connect with others or to erect a facade?

How would you live differently if it wasn’t about the show but about creating the best life for you, your loved ones, and the other humans you share this planet with?

Day 12

“The big question about how people behave is whether they’ve got an Inner Scorecard or an Outer Scorecard. It helps if you can be satisfied with an Inner Scorecard.” —Warren Buffett

An inner scorecard is something we can create ourselves and then look at to know whether or not we’re doing well. An outer scorecard is something the world creates for us and then judges us by. If we accept an outer scorecard we forfeit our self-reliance.

In investing, Buffett has often acted against the crowd — sometimes losing money when others are winning and missing out on massive trends — and has credited his inner scorecard for helping him stay the course when otherwise he might have abandoned ship.

Today, make a draft of your internal scorecard. Make a list of things that will help you know whether you’re on the right course — even if the world’s outer scorecard can’t see the wins.

Day 13

“Envy is ignorance.” —Emerson

Envy of someone’s wealth is ignorance of the relationships, life experiences, and health that may have been sacrificed to gain it. Envy of someone’s power is ignorance of the tragic sense of inadequacy that may have provided the drive to achieve it.

Even though we often use Social Media Highlight Reels to gauge a life, we know we shouldn’t. Divorces can be preceded by a slew of romantic travel pictures. Few go to Facebook to talk about their crippling mental illnesses. One doesn’t post updates about familial turmoil online.

Make a list of people you envy.

Would you trade places with them? Would you give up your whole life for their whole life? Would you switch spouses, health, history, mental health, etc. with them? What are the potential downsides to their position in life? What sacrifices might you have to make in order to get the piece of their life you want?

Day 14

Self-reliance isn’t standing alone. Asking for help from friends, family, or professionals is an important skill.

Joseph Campbell has said that, “The problem of the psychiatrist is to disintegrate [the] dragon, break him up, so that you may expand to a larger field of relationships.”

It’s not about giving up or using other people as crutches. It’s about being self-aware enough to know when you need a hand or where you could use an outside opinion.

How could you better use the help of those around you? Where and how is your ego holding you back from getting assistance?

Day 15

List a few big events from your past that caused you suffering. Was there some growth — or even some good — that came from them? What growth? What good?

More challenging: can you do this with the situations that are currently causing you suffering?

This is a baby step toward Nietzsche’s amor fati — the love of your fate. Which is no small thing:

“My formula for human greatness is amor fati: that one wants to have nothing different, not forward, not backward, not in all eternity. Not merely to bear the necessary, still less to conceal it . . . but to love it.”

Day 16

In The Gay Science, Friedrich Nietzsche introduces the idea of “Eternal Return”:

“What, if some day or night a demon were to steal after you into your loneliest loneliness and say to you: ‘This life as you now live it and have lived it, you will have to live once more and innumerable times more; and there will be nothing new in it, but every pain and every joy and every thought and sigh and everything unutterably small or great in your life will have to return to you, all in the same succession and sequence — even this spider and this moonlight between the trees, and even this moment and I myself. The eternal hourglass of existence is turned upside down again and again, and you with it, speck of dust!'”

Basically, Nietzsche asks the reader to imagine repeating this life, as it is lived this time, over and over again for eternity. Nothing would change. You couldn’t make different decisions or take on different attitudes. And you wouldn’t be conscious that you’re reliving your life.

If you knew you would undergo an endless cycle of Eternal Return, what changes in your attitudes and actions would you make to your life right now? If there are things in your life you wouldn’t want to repeat for eternity, why haven’t you changed them yet? Remember, the goal is not just to endure this life, but to love it — all of it. To amor fati.

(If you’re interested in going deeper into this thought experiment, check out the full article on the subject.)

Day 17

“A man should learn to detect and watch that gleam of light which flashes across his mind from within, more than the lustre of the firmament of bards and sages. Yet he dismisses without notice his thought, because it is his. In every work of genius we recognize our own rejected thoughts: they come back to us with a certain alienated majesty.” —Emerson

Recall a time or two in which you had an idea for something, left it as an idea, and saw someone take advantage of it later. Are you glad you didn’t pursue the thing? If not, what can you do differently in the future when an idea grabs you? Try to be specific; a bold claim of, “I’ll seize the opportunity!” will likely leave you in the same situation again. What’s the plan?

Day 18

After hearing Emerson debase the value of novels, a young college student, Charles Woodbury, became deeply disappointed in the mentor he nearly worshipped. Nervously, with “quivering lips,” Woodbury said he simply couldn’t agree with the philosopher’s stance.

“Very well,” Emerson answered with a twinkling eye. “I do not wish disciples.”

This moment, Woodbury later remembered, “was a long step toward manhood.”

If you want to think independently, it can be dangerous to become a “disciple” of another person. (You can know them personally or not.) Is there someone you reflexively agree with? Take some time to humanize them. List off their scandals and mistakes. Write down something they might be wrong about. How does this change the way you read, listen to, or converse with them? Does it loosen their hold over your opinions? Are you able to think more critically about them?

Day 19

Make a list of areas where you’re deferring your life. Things you’re waiting to do. How can you skip or dramatically reduce the wait?

Why are you waiting? Are your concerns based in reality?

If they are, how can you make sure you never actually “wait”? What kind of active preparation can you engage in now to be ready when your time comes?

Day 20

List the 5 activities that energize you the most. How can you spend more time with them?

List the 5 activities that drain you the most. How can you spend less time with them?

Day 21

“God will not have his work made manifest by cowards.” —Emerson

Our ennui often comes from holding back, from half-assing what we should be fully committed to. Where could you break through if you went all the way? Where are you holding back? What feels stagnant?

How can you give it everything you have? Does it need more time? More intensity? More care?

Day 22

“Enlightenment means taking full responsibility for your life.” —William Blake

“This is not your responsibility, but it is your problem.” —Cheryl Strayed

We’re responsible for our lives. Even when crap happens we had nothing to do with, it’s still our problem. We may not be responsible for causing it, but it’s still our responsibility to figure out how to deal with it. What areas of your life do you blame others for? Or society? The economy? Your genes? How can you take responsibility for the situation they threw you into?

Day 23

“[I]mitation is suicide.” —Emerson

How have you modeled your life after others? Have you lost yourself in the process?

Day 24

“A man must consider what a blindman’s-buff is this game of conformity.” —Emerson

Make a longer list (15+) of your basic assumptions about life. Go back and look at each critically. Is this true? Why do you believe this thing? Because someone told you it’s the truth or because you’ve seen it proven? Or because it’s something you’ve chosen to have faith in?

Day 25

“A foolish consistency is the hobgoblin of little minds, adored by little statesmen and philosophers and divines.” —Emerson

When is the last time you changed your mind about a deep-seated belief? Is there a belief you’re holding onto, despite an accumulation of contrary evidence, because you’re stubborn, or don’t want to feel inconsistent, or simply are afraid to let it go?

Day 26

“The voyage of the best ship is a zigzag line of a hundred tacks. See the line from a sufficient distance and it strengthens itself to the average tendency. Your genuine action will explain itself, and will explain your other genuine actions. Your conformity explains nothing.” —Emerson

Recall a time where you were thrown off course only to find yourself where you intended to be — or somewhere better.

How can you focus less on the end destination, and more on doing what’s right, right now, when you’re forced to take a detour?

Day 27

“If we live truly, we shall see truly.” —Emerson

Nassim Nicholas Taleb wrote, “Mental clarity is the child of courage, not the other way around.”

Is there an area where confidence or action could actually straighten out your thinking more than another book?

Day 28

“At times the whole world seems to be in conspiracy to importune you with emphatic trifles. Friend, client, child, sickness, fear, want, charity, all knock at once at thy closet door, and say — ‘Come unto us.’ But keep thy state; come not into their confusion. The power men possess to annoy me, I give them by a weak curiosity. No man can come near me but through my act.” —Emerson

Emerson’s exhortation that “The man must be so much that he must make all circumstances indifferent” is intimidating. It’s hard to be indifferent to all circumstances; still, we can work to become indifferent to more of them.

To Emerson, self-possession matters greatly, but the point was never to become disconnected from your humanity. The sentence that precedes the above quote: “But your isolation must not be mechanical, but spiritual, that is, must be elevation.

When the world seems intent on outraging you, how can you maintain your sanity without becoming a misanthrope?

Is it caring about the right things? Is it being so focused on your aim that every obstacle is just fuel for the fire? Is it learning to tame your desires? To be more aware of silly frustrations? What will work for you?

Day 29

“When we blather about trivial things, we ourselves become trivial . . . You become what you give your attention to.” —Epictetus

Reflect on how you distribute your attention throughout the day. How much of it is directed to what is truly important? How often do you allow yourself to become trivial? If we become what we focus on, what are you becoming?

Day 30

“All life is an experiment. The more experiments you make the better.” —Ralph Waldo Emerson

“When we imagine future circumstances, we fill in details that won’t really come to pass and leave out details that will. When we imagine future feelings, we find it impossible to ignore what we are feeling now and impossible to recognize how we will think about the things that happen later.” —Daniel Gilbert

If we are to rely on our own experience about something, we’ve got to have experience with it in the first place!

We’re terrible at imagining how we might like something or how we might perform. We’ve got to experiment. To get our hands dirty and find out firsthand whether or not we like the thing, or if the study applies to us, or if the thing we’ve been dreaming about is really what we want to tackle.

Where have you been indecisive, stuck between two choices about which you only have abstract information? Where have you been making assumptions? How can you test those assumptions? How can you conduct an experiment to get firsthand experience of something?

Day 31

Having the help of others is one of the best gifts in life. No matter how much help we get, though, there is always a step that only we can take. Joseph Campbell talks about this beautifully. Here he is in conversation with Bill Moyers for The Power of Myth:

Moyers: “When I take that journey and go down there and slay those dragons, do I have to go alone?”

Campbell: “If you have someone who can help you, that’s fine, too. But, ultimately, the last deed has to be done by oneself. Psychologically, the dragon is one’s own binding of oneself to one’s ego. The ultimate dragon is within you, it is your ego clamping you down.”

Which dragon are you battling now? How and where is your ego holding you back from making progress? Have you been preparing too long to act? Have you been waiting for others to finish the battle for you? Have you been using others to avoid the next step you know you must take?

Are you ready to slay the dragon yourself?


Kyle Eschenroeder is a writer and entrepreneur. He previously authored The Pocket Guide to Action: 116 Meditations on the Art of Doing. Once a week he sends out a letter with 5 important ideas; click here if you’d like to be included. 

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