Many say that the hardest part of writing is moving from daily activities to being able to create work that transcends the daily. There are ways, though, to launch new writing that unexpectedly gets you to your deepest material while allowing you to make the shift easily.

What follows is an exercise that is meant to take five days to accomplish; that’s good because for a few days you’ll have an assignment and be able to get to work without wondering what to write about.

Here are five freewrites and a final step to do over a period of time. If you can’t write consecutively over five days and need to write from more than one prompt a day, separate your writing spurts by a few hours so when you start again you are fresh. And, please, try not to look ahead at the prompts. The writing will serve you best if you know only one at a time as you move through the writing exercise.

If I were in the room, I would not tell you what the next prompts are. For the best results, pretend I am in the room each day dealing out the prompts as surprises, each one after you have finished the one before.

Prompt #1:

a) List five concerns you have that you don’t feel you can address right now, whether that is because the concerns are about others and/or involve dealing with those you can’t influence or because the problem seems overwhelming and you can’t find a way into a solution or you need more information. The list should contain both large and small concerns. Nothing is worthless in writing. Sometimes the smallest moment leads to the largest insight.

b) Next, go to a window wherever you write or, even better, a window in some place you have never written. Choose one of the items on your list. You’ll know which one has energy for you at the moment by trusting your pick, or use whichever item your eye falls on if you can’t trust that.

c) Set a timer for 20 minutes.

d) Close your eyes and in your mind’s eye see the words of the concern you picked just as you wrote them.

e) Without using those words or describing that concern, freewrite about what you see outside the window where you are sitting. Be sure to fill your writing with the specifics of what you see, hear, smell, taste and touch, outside the window and inside where you sit. Some of what you see, hear, smell, taste and touch can be remembered from other situations and times. Leaps of association are welcome in this writing. Keep your fingers typing or pen moving until the buzzer goes off.

f) When the buzzer goes off, continue writing in this way if you want to but you don’t have to. You’ve already fulfilled your goal if you kept on writing for 20 minutes after you imprinted the concern on your mind and in your heart.

Prompt #2:

a) List five things (one for each concern or several for some of them) that you or others involved in the concerns have said.

b) Choose one of the pieces of dialog you remember and imagine saying it today, now, to someone or an object unrelated to the concern.

c) Set your timer for 20 minutes and write a fantasy conversation with that audience or a monologue meant for that audience or one from that audience to you. Of course, you cannot mention the concern or the context from which you took the original words, but you can use those words to start off your freewrite or as a title for it.

Prompt #3:

a) List five objects that are involved in the concerns or that you associate with the concerns, one for each of the concerns or several from one or more of them up to five in all. This might be someone’s scarf or mole, say, or a specific chair or afghan or oatmeal raisin cookies baking in the oven or a toaster popping its bagel or English muffin up. Allow yourself to range widely but specifically in your list of images.

b) Set your timer for 20 minutes.

c) Describe each of the objects you’ve listed using words that appeal to the five senses. You will be writing what it looks like, feels like, tastes and smells and sounds like or what was in your mouth or the air or your ears at a time when this concern came up or just now when you think about it. Still, of course, you are not to mention the concern that generated your list but to stick only with the description of the objects you have listed.

d) If you’d like to title this list piece, you can use a phrase like “What Calls to Me.”

Prompt #4:

a) Set your timer for 20 minutes.

b) Write an anecdote about something that amused you lately—something you saw on television or while shopping or something that happened at home or in your neighborhood.

c) Be sure to tell the story with specifics—where you were, what it looked and sounded and felt like, who was there, what others and/or you said.

Prompt #5:

a) Set your timer for 20 minutes.

b) Write an anecdote from the past about something that worried or upset you or made you laugh. It can be from your childhood or teen years or anytime at least a decade ago.

c) Again, stay specific—who was there, if anyone, what the room or outdoors looked like, what you said or wanted to say, what anyone else said.

d) Other than because you have decided to write from this prompt, why might you be thinking about this event today? Write that as you end your writing time.

The Next Step

Good writing taps the unconscious by a kind of layering—we write about one thing, something seemingly unrelated, to explore what is deep inside of us. We often feel as if our experience of being alive is bottled up because the circumstances we live in don’t allow its full expression.

a) To begin to unbottle your deepest writing and self, look into the five freewrites you’ve done and underline those words and phrases and passages that have energy for you, that move you now. Look also for words that come up again and again throughout your writing.

b) Take three to seven or more of the passages, long and short, that you’ve identified in the freewrites as having energy for you and title each one with a word that you have been using often in your writing or with one of those words over and over, as if each passage is a new take on that word.

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My hope is that you see a resulting personal essay (built from separate parts) that explores something you have been dwelling on that you perhaps hadn’t noticed. I hope you see that your way of being concerned keeps you present to the world and contributes richness to your writing.