A Baker’s Dozen of Writing Practices to Fuel Insight


Write a letter freely, without editing, to someone with whom you have unfinished business, or to someone you imagine would be a friendly audience for your thoughts.

Some people work stuff out with their parents (or children) this way, without ever sending the letter, or with people who have died or aren’t in our lives anymore.

You can also pick someone to write to who isn’t implicated in what you’re writing about. They don’t have to be someone you know personally or even be real — they just have to be someone you have a good feeling about. You can also write to your future imagined self or to the wisest part of you.

If you don’t have a specific thing you want to say, you can start the letter with, “I want to let you know what’s up with me. This is a time in my life when….” and then finish that sentence as many ways as come to you. Keep writing to this imagined other as much as feels helpful to you. Create a file where you keep these letters and re-read them on occasion to gain perspective about where you are in your life and what you might want next.


A sticky thought is one that is hard for your mind to let go of and usually comes with some unpleasant feeling. Sticky thoughts are often worries about the future or regret/guilt about the past.

Grab a piece of paper or open a document and start by writing the thought down. For instance: “What if this is the wrong relationship for me?” or “I’m not doing a good enough job at work.” Next, write this sentence, “And what would it mean if this thought were true?” Write the answer that comes, starting with, “It would mean that…”

Then, write the question again: “And what would it mean if that were true?” Keep going until no new content is emerging. The last answer you arrive at is likely to be a core fear you have. You can also read this article and follow their instructions at the bottom.


When you notice yourself ruminating on a thought, grab a card and start the sentence, “I’m having the thought …”

The thought could be, “what if I can’t finish this project on time?” or “The world seems awful this morning” or “Why am I so tired up all the time?” Make sure to start your sentence though with “I’m having the thought that…” because that helps frame the thought as a thought that is not necessarily reality. Put the date on the card and drop it into a folder or make it the beginning of a stack you’ll put a rubber band around. Add more cards to the folder as you have more sticky thoughts in the coming days and weeks.

For extra credit, you can come back to an index card any time later and add a thought to the back of the card that relates to what you put on the front. It could be “I’m having the thought that this still feels true” or it could be, “I’m having the thought that what feels true now is….” Put the date on that side of the card and re-file it. When you have a small collection of these cards, you can look through them and start to notice recurring themes in your thinking.

You can grab a piece of paper or open a document and start the sentence, “I notice in re-reading my index cards that my thoughts …” and record whatever you notice — it could be how your thoughts change over time, it could be noticing the ones that don’t change, noticing the ones you would like to be different, or noticing what kinds of thoughts are not represented. You can bring these observations to a friend, therapist, or trusted advisor to talk about what you’d like to change about your habitual thought patterns.


This comes from a wonderful book called Writing Alone and With Others by Pat Schneider. Grab a piece of paper or open a document and write a sentence that starts with, “I’m a person who…” And then finish that sentence as many ways as you can think of in that moment. Keep going until no more material comes. Keep that document on hand and add to it if more occurs to you about how to finish that sentence.

Let the document rest, make a date to come back to it in about a month and re-read what you’ve written. Grab a pen or highlight the sentences that particularly resonate for you today. Notice clusters of themes. Open another document or piece of paper and start the sentence, “from re-reading what I have to say about the kind of person I am, I notice that…” and write everything you notice until no other observations arise. You may only have one or two observations or you may have many.


Open a document or grab a piece of paper and write sentences that all start with, “I’m afraid that…” until no more sentences come.

You can do this about a specific situation that’s causing you trouble or you can do it anytime you’re feeling uncomfortable in a non-specific way. You can also do this with “I feel angry that…” Noticing the themes that repeatedly cause you fear or anger can be helpful for directing personal work (with a therapist, coach, or for further writing).


If you have any interest in the I Ching, you can use readings as a prompt for writing.

Pose a question to the I Ching like, “what is your image of me at this moment in my life?” or “what do I need to know this week?” Then with the material that comes back (either on this website or using a reputable I Ching version like this one), pull out words, images, and phrases from the reading that resonate for you.

You can make some notes after each excerpt you’ve pulled out saying why it grabbed you, or you can just write freely for ten minutes about how the reading overall feels relevant to you in this moment.

You might also note if your reflections on the reading raise follow-up questions and you can take those back to the I Ching. If you find working with the I Ching frustrating because the language is too obtuse, reach out to someone who does readings to help you learn to work with it (the woman whose website I link to above does and I do, and there are no doubt many others).


If Jungian psychology appeals to you and you’re interested in a rich, complex experience, take a look at Ira Progoff’s book At a Journal Workshop.

Progoff is a Jungian/Depth psychologist who developed a reflection and writing process called Intensive Journaling which he and others taught at workshops all around the world for years. His method is an absolute work of beauty and it takes a commitment to dive into it. If you like office supplies, you’re going to especially like this one.


James Pennebaker’s book Opening Up by Writing It Down: How Expressive Writing Improves Health and Eases Emotional Pain offers a path for using writing to process trauma, adversity, illness, the cost of keeping secrets, and other difficult experiences.

Here’s one exercise from the book:

“Find a quiet time and place for this next writing exercise. Think of a topic that you have not previously discussed or disclosed with others; perhaps you have even inhibited talking or thinking about it. Write about this topic for 20 to 30 minutes; as in prior exercises, try to write continuously and do not worry about style, spelling, and so forth. When done, reflect on how you felt physiologically — how did you feel during writing? After writing? Review your writing: Do you notice any patterns or insights to be gained? You might repeat this exercise in several days and see if additional changes or insights come.”


You don’t need any particular instruction, but you can look here and here for inspiration.

If you have trouble remembering your dreams, read this.

Another dream remembering trick I’ve found helpful is to rest your hand on the bed or on your body as soon as you are waking and press each finger down in turn as you remember five things from your dream. Later you can put your hand in the same position and see if you can retrieve the five things from the dream, which can be a thread to help remember more of the dream.


Take a favorite idea of yours, one that you feel strongly about or you find getting into arguments about, and test drive it in writing. Make the case to support your stance.

When you feel you’ve made all your arguments, take a break, go make a cup of tea or walk around the block. Come back and try to make some arguments against your stance. Don’t expect those arguments to come as easily or be as cogent — you’re building mental agility just by trying.

Next, see if there’s one thing about the opposing argument that you can appreciate at any level. And see if you can notice one thing about your own stance that you don’t particularly like.


When we’re struggling with a situation, it’s often because different parts of us are in conflict. It can help to give names to these parts and let them speak to each other. You can call them things like the Critic, the Child, or the Protector, but you can also call them things like Harry or Maude, whatever captures their personality best for you.

Fold a piece of paper in half vertically and put the name of each part at the top of each half of the page or you can just type it out like dialogue in a play. Imagine as you get started that you’re stepping off the stage and into the audience to witness this conversation; you’re transcribing it, not participating. Let your parts speak to each other about the issue in question until they both feel reasonably heard.

At the end of it you can say or write, “Thank you for speaking up. I’m taking all this in and will be considering it in the coming days. I’ll circle back to you if I have questions.” You don’t need to do any further work on this; the act of listening and recording this dialogue will do its own work on you and how you relate to the situation. Though you can pay attention as you go through your days to where these parts and others you may notice have opinions or reactions. Working with them in an ongoing way can be very helpful.


The hand we don’t normally write with can help us access unvoiced aspects of ourselves. There are lots of ways to work with this, I’ll give one example:

Let’s say you have a part of your body causing you trouble — a tight shoulder, a recurring headache, an unhappy gut. Whatever it is, let it speak through what you write with your non-dominant hand. You’re going to do this on paper with two different writing tools (pencil, crayon, pens of different color, etc). Let the non-dominant hand write with something you don’t normally use for everyday writing. Let your dominant hand write with something it usually uses. Take a moment before starting this exercise to relax your body and release the preoccupations of the day.

With your dominant hand, write at the top of the page, “I’m listening. Please tell me what’s going on with you.” Let your non-dominant hand answer in whatever way it can, even if it’s barely legible. Let it use “I” language if that feels okay. Maybe it doesn’t speak in full sentences and just offers a few words and images, that’s fine.

Ask it any questions about its experience that you want to know — write those questions with your dominant hand. You can also ask it, “What would you like me to understand?” and “How can I help?” When it seems like your body part has said what it came to say, write your thanks to it, adding something like, “I am going to take what you’ve said to heart and am going to try to help. I am also going to keep listening now, maybe in a way I haven’t before.” You can repeat this daily for a couple of weeks or every week for a few months. I’ve seen people release long-term chronic pain by doing this exercise.


Here’s an exercise that comes from this article on making tough decisions:

“Put aside time on a regular basis to mindfully reflect on the situation. The best way to do this is … using a diary or a computer, write down the costs and benefits of each option, and see if anything has changed since last time you did this.

“Try to imagine what life might be like – both the positives and the negatives – a) if you went down one path, and b) if you went down the other path. For most people, ten to fifteen minutes 3 or 4 times a week is more than enough reflection time – but you can put aside as little or as much as you like. The key thing is, make it focused; in other words, don’t try to do it at the same time as watching TV or doing housework or driving home or going to the gym or cooking dinner; just sit quietly with your pen and paper or a computer, and do nothing else but reflect, as above, for the allotted time.”

Read more here about making tough decisions.

Come back for more writing practices I’ll be posting in this space.