Write/Right

75 Writing Prompts // Middle & High School

I am a teacher and I love my job. I love it to the point where I wish we could totally change the way that schools are run and the way education is organized so that it sort of never ended. Any worthwhile learning shouldn’t have an ‘end date’. Alas, school does have an end date, and as such, I’m constantly asked questions like, ‘How can I prepare my child for next year?’ Well, aside from fostering their passions, encouraging creativity and imagination, and listening to them, you can encourage them to write and read, the two most valuable things you can do to become a better writer, reader, and thinker.

At the end of the year I provide the students with an empty composition book, a list of seventy-five prompts, and a promise that for every student that takes the time to answer every single one in a page or more, I’ll take the time to respond to each prompt. Is it a small offer? Nope. Is it a worthwhile one? Most definitely.

Writing and reading and learning and improving are lifelong endeavors, not bound by time constraints. Make the time to write, every single day, and if you’d like to share them with someone, send them over to me, I’ll respond. Maybe you don’t want to share them, that is fine as well. Here’s one thing I do know, if you do this, you’ll feel accomplished, you’ll have written a novella (or more) of your opinions, and you’ll likely feel inspired to write more. Worth a shot for just a few minutes a day, right?

1. Now that school is over I am going to…

2. If I could work anywhere right now, I would work…

3. The greatest song ever is ________, because…

4. If I were a cartoon character I would be…

5. In ten years I will…

6. You’d have never guessed it but this past school year, I…

7. If I could be any animal I would be…

8. If I could have dinner with any five people in the world, they would be ______, because…

9. If I could cure any disease, it would be…

10. If I was offered the job of President I would take it/not take it because…

11. If I were a food I would be…

12. If I were a door-to-door salesperson, I would sell…

13. Cool is…

14. The best smell in the world is…

15. If I could have any one talent, it would be…

16. If I could give myself any one nickname, it would be ______, because…

17. High school will be (or was)…

18. The summer is...

19. My family is…

20. Whether it’s for better or worse, there’s no place like home because…

21. My best friend(s) is/are….

22. I will change the world by...

23. The greatest movie ever is _____, because…

24. I’ve never laughed as hard as when…

25. The thing I’m most excited for about high school is...

26. My dream vacation is…

27. I promise myself I will never…

28. The Fourth of July is…

29. My favorite holiday is…

30. I will miss __________ about this past year the most because…

31. When I was little I wanted to be _______ when I grew up because…

32. If I had to be stuck in a store overnight I’d want it to be ______, because…

33. The best gift I ever got was _______, because…

34. The best gift I ever gave was _______, because…

35. This world needs more…

36. This world needs less…

37. If I could have invented any one product it would be ______, because…

38. If I could move anywhere in the country it would be _______, because…

39. The worst TV show ever is…

40. If my life had a motto it’d be…

41. When I daydream I daydream about…

42. The funniest thing I’ve ever done is…

43. The last dream I remember is…

44. In twenty years, America will be…

45. If I could create one law it would be…

46. If wishes and buts were candy and nuts…

47. I would like to convince my parents that…

48. Why didn’t I…

49. If I could only eat one type of food for the rest of my life it would be ______, because…

50. The worst time I’ve ever had was…

51. What color represents you? Why?

52. I think that Facebook/IG/Snapchat/whatever is...

53. Our town should have a _________ Club, because…

54. I believe that animals are…

55. The biggest risk I’ve ever taken is…

56. I’m most creative at/in…

57. Write a poem.

58. Go interview someone about a topic of your choice and transcribe it here.

59. What is your most valued possession and why?

60. What are you optimistic about? What are you pessimistic about?

61. What do you think the world needs now?

62. What makes a good friend?

63. What do you consider to be beautiful?

64. How do you feel on the first day of school?

65. How do you feel about your appearance? Why?

66. The last time I cried was _______, because…

67. When I have a problem I talk to ______, because…

68. I used to think…

69. I am most afraid of ______, because…

70. If I could add words to the dictionary, these would be six of them with their definitions…

71. List twenty rules you’ve broken. If you don't have 20, get breaking and chronicle them here.

72. What dangers would you face if you were a squirrel and how would you overcome them? And what would your name be?

73. Close your eyes, you are in your favorite place ever, describe it...

74. The most important issue in our world today is…

75. I’m going to change the world by…

The Magical, Mythical Poet // Christoper Roof

Christopher Roof and His Impact on Concord, Massachusetts

Christopher Roof was of the wrong generation, of the wrong time period maybe, or maybe even of the wrong world.  So maybe it should have come as no surprise when he disappeared in 2010 – he was never really meant for here and now in the first place.

As a child growing up in Concord, Massachusetts, it was impossible to not know Mr. Roof.  He was Alcott’s most beloved substitute, he led Sunday school classes at the First Parish Church, and he was forever wandering, like a modern-day Thoreau, through the streets of Concord.  His appearance in a classroom would be cause for celebration – there would be no testing, no correcting papers, there’d be no work other than play.  We would spend the day imagining, creating, all the while listening to his poetry in that calm and peaceful voice of his.  As a child growing up in Concord, Mr. Roof was a light in an otherwise dark hallway, not because the other teachers were poor (in fact, every teacher I had at Alcott was exceptional in different ways) but because he was different, he was unlike the world around him and it made him stand out, it made him shine.

When it comes to Christopher’s childhood, it was a far cry from the ordinary life of the average Concord child.  The child of fortune and fame (and later infamy), Chris was the son of the daughter who inherited a great deal of the Sheraton Hotel fortune.  After spending his early childhood years in India, spending time with the family of Gandhi (amongst others), being introduced to the world of non-violence and peaceful protest by his parents (who were clearly in the process of their own spiritual journey), he returned to the states in 1957.  In 1961 at 10 years old, his parents divorced and their paths went very different ways. 

Chris’s high school years were spent studying at the Cambridge School of Weston where he was remembered fondly as a lover of fantasy writing.  He was a solid student and a passionate writer who was considered shy by teachers.

When he graduated high school, Roof took a tour of Britain with his high school roommate Mark.  His poetic voice was already forming and he said he felt very much at home in his travels in a journal he kept while traveling.  It’s hard to tell from the writing of his that survived if Chris ever felt this sort of contentedness again.  During his trip he traveled by bicycle (upwards of 80 miles some days), hiked, and hitchhiked regularly.  Although he found joy in his debates with his travel partner, the scenery, and the food, his journal shows that the most profound source of joy was his interaction with children along the way.

It’s unclear exactly what it was that made this time spent with young people more meaningful, whether it was his own mindset immersed in a fantasy world only children could appreciate or something else, but his reflections from this trip show the beginnings of his connections with young people – and hint at his troubles with communicating effectively with everyone else.

In the fall of 1970, he was one of the 250 inaugural students accepted into the first class at Hampshire College.  In 1972 he transferred to Emerson where he graduated with honors in 1974.  One of his more influential professors at Emerson, Charlotte Winslow, remembered him as quiet and kind, saying, “He did not seem that much of a loner in spite of his admiration for Thoreau.  Christopher was rather a gentle person who loved fantasy as evidenced by his writings and enjoyed playing with words.”  He lauded Jane Austen, criticized Wordsworth, and compared Coleridge to J.R.R. Tolkien – in his writing, there was passion and there was confidence. 

The juxtaposition of his love of fantasy and his desire to make a meaningful difference in the world explains how a man obsessed with Tolkien and Thoreau could also be arrested four times for civil disobedience and refuse in writing to his draft board to be involved with Vietnam (very appropriately, in a letter saturated with Thoreau quotes).  It’s also this which might have led to a much more difficult life for Christopher as he got older, as he hadn’t necessarily learned how to separate his idealism and fantasy from reality and facts. 

His mother’s disappearance and the media sensationalism surrounding her murder in 1979 definitely fostered tension in his family but it’s unclear how this actually impacted Chris at the time.  His only recorded comments on the incident share little about his feelings and he never publicly wrote about the topic.  It’s also something that managed to not make it to the ears of the children he would soon start working with in the Concord Public Schools. 

Through the 1980s, Christopher wrote a number of children’s books, books that starred peers of mine in writing or illustration, that were dedicated to children in town, books that made us feel like we were being taught by a world-famous poet every time we were fortunate enough to have him as our substitute teacher in class.  These books were all over the map even from one poem to another in the same collection.  Roof was a technical poetic genius, using advanced rhyme and meter flawlessly in poems for elementary school students.  He also appeared bipolar, one moment being incredibly childish and the next almost inappropriately mature for his intended audience.  There were huge brushstrokes of him in his writing that we’d never have noticed as children but one can only wonder how more parents and townsfolk didn’t notice – or didn’t stop to think about what it all meant.  “The Eccentric Young Fellow” is about a poet who lives in a church steeple and is misunderstood by everyone around him except children.  There were hints of his desire to escape the confines of the small town and his fear of commercial failure that he was seeing come true with every single rejection letter he received – and he received many over the years.

“And that nonsense he writes couldn’t possibly sell/ So Bartholomew drifted around like a ghost/ His appearance becoming forlorn… Now he wished he was back in his steeple again/ If the people would leave him alone.”

It’s unclear how autobiographical any of this is, after being encouraged by his friend Kristina Joyce, Christopher decided to donate his papers to the Concord Public Library and seemingly haphazardly chose what writing to share, leaving it up to the public to glean what they could from it.  It’s also unclear what happened that led to Christopher’s leaving his post at the First Parish and stopping his work in schools in Concord, but it is clear that at some point he stopped feeling that Concord was his home.  Long-time friend Joyce says that he moved north saying that he, “liked New Hampshire because of the anonymity.”  Although for the most part he was able to escape the people of Concord, and possibly memories of whatever happened that led to his feeling of being removed from that community, he wasn’t able to escape what he viewed as a failed career as a writer.

The fact is that Christopher Roof was a skilled writer, but it’s clear from the few people who had an opportunity to get close to him, that he lived in a world different than everyone else, a world removed. One writing peer, whose relationship with Roof didn’t last long, believed that he lived in an “atmosphere that was simply too rarefied”, likening his writing to that of a “precocious seventh grader” because of the simplicity and childishness of the problems and solutions presented. His aunt, wife of celebrated author Robin Moore, told him in a letter to him that she thought one of his stories was “wonderful” and that “with the right illustrations, I think it could easily become a children’s classic!” When asked about his uncle’s literary success, Roof expressed resentment to another friend in Concord, pointing out that his own writing was of much higher quality than Moore’s.

It wasn’t just his uncle or friends that Christopher ran into trouble with when it came to his beliefs or opinions – his immediate family found it challenging as well – and it’s possible that his unique idealism, this view of how he thought the world should look – and his opinion that his view was the only correct view, caused far more harm than good in his life. His brother Jonathan, who he was in and out of touch with throughout his adult life told me that even though they, “always got along well, it was kind a hard to engage with Chris” due to the fact that Chris “had very definite opinions about things and didn’t want to hear others' opinions about things.”

None of Christopher’s books ever were picked up by publishing houses and he opted to release them on his own with the money that he hadn’t otherwise been donating quietly (and in large sums) over the years to various Concord historical and nature societies (especially the Thoreau Society, where he was very involved for quite some time).

We may not have the answer as to where Christopher Roof is right now but we do know that after over thirty years of being a staple in Concord, he moved to New Hampshire, then up and disappeared – and all of a sudden it was like he never existed. There was no frantic search for him, there was little more than a Facebook page made – where one poster had the audacity to tell people not to bother looking for him because maybe he wanted not to be found.  And now, over a year after his lease expired on his rented Nashua home, no one, not the family members who were willing to speak to me or his closest friends, have any idea what happened and where he is.

Maybe he was providing a clue when he told his close friend Kristina Joyce, “I can get on a bus and go anywhere from Nashua,” maybe he’s out wandering some other small town (like his hero Thoreau). Or possibly as the protagonist in his poem “A Visit From the Muse” from the Mythical Magical Poetry Book, maybe he had “written everything he had to write,” and it was time for him to take his leave of this world (or as his brother Jonathan worded it, maybe he just decided to “hang it up”), a world that he felt, and I’d agree, never quite appreciated him enough while he was a part of it. 

What I do know is that Christopher Roof’s life mattered, a lot, and not just to me. In a world where it’s hard to tell how people feel about you and it’s hard to tell whether someone is on your side or not – there was never any question as to where Mr. Roof stood. He stood with kindness, and he stood with young people. Christopher Roof stood for believing in a more magical and more beautiful world and I only wish I’d had the opportunity to let him know that I stand with him, a great number of us did. Wherever he happens to be right now, we can only hope that he knows the impact he was able to make in our lives, and hopefully, it will teach us to make sure that we let the people around us know just how much they mean to us – and for that, he was the most valuable teacher in Concord.

Thru (on what it takes to thru-hike the Appalachian Trail).

I never really thought that I'd end up hiking the Appalachian Trail. It had crossed my mind as something that could happen. I even remember being about 21 and heading down to Georgia and hiking the beginning of it - but it never really struck me as something that I really needed to do. It never called out to me, and to be honest, it never sounded all that compelling either. I don't particularly enjoy camping, and most of the things I really enjoy about hiking have historically sort of been ruined for me when I had to carry a bunch of stuff on my back. And yet, just three weeks ago I completed the 2,186 mile thru-hike of the Appalachian Trail in one hundred thirty seven days. Why?

The primary reason for hiking the AT for me was a relationship. Not the love of nature and the woods (although I do love nature, I do love the woods). Not the love of adventure and excitement (I do love adventure, as well as excitement). I was dating someone and hiking the Appalachian Trail was something she'd always wanted to do. As a result of the fact that I (almost) obsessively believe that you should follow your dreams (and want to encourage people I care about to do the same), I suggested that we just go ahead and hike the trail.

Yes, it was that simple. Let me repeat, for the sake of making my point. I just decided it was what we should do, then we planned, then we did it.

Again, there's not much more to it.

Why harp on that fact? Well, although it wasn't on my short list of life goals, I realize that it is on a lot of other people's lists. And the sad fact is that a huge number of those people aren't going to ever hike it. I'll get to that later though. Let's go back to the beginning of the hike.

In order to hike the trail, I had to be willing to take a year off from the thing that I love doing most in the world, teaching. I love teaching. If you were a bully in 4th grade and heard me say that, I'd respond to your follow-up taunt by saying, "Yes, if teaching were a person, I would marry it." I love it. I love working in a classroom, I love encouraging young people, I love to challenge them and love when they challenge me. It's the best thing I believe I could be doing with my limited time here on Earth. And I had to be willing to give this up for a year to attempt something that only about 25% of folks who start complete. I believe in taking chances though, so I did it, and I went into it confident that we would complete the entire hike.

Why did I have such confidence? Because there was no way I was going to give up a year of doing what I love to not complete it.

Now, preparing for the trail wasn't a huge deal. It was more fun than anything else really. I did some reading about it, I looked up stuff online, I got in touch with other folks who'd hiked it and asked questions, I looked at some maps, I made some care packages, I did some stair climbing. And it was all pretty much useless.

Well, that's not completely true - but it's pretty close.

The amount of information available these days online is absurd, and the great majority of it (no matter what you're looking up) is useless. It's exponentially more useless when it's all opinion (very little of what I looked up was factual information about the trail). Everyone has an opinion it seems (wait, isn't this an opinion?) and everyone believes their opinion is right (if this isn't, why am I writing it?) So there are hundreds of people out there telling you exactly how to pack, what food you need and don't need, what supplies you must take with you, what you'd be a fool to carry, how challenging different terrain will be, what you must fear, everything you should expect. And yeah, it's useless.

Nothing would have prepared me for this hike properly except section hikes of the trail, and that would have only prepared me for the section of the trail (assuming I also reached it in identical weather and feeling exactly the same mentally and physically as I did the first time). That's not to say some info wasn't helpful (much better to choose a stove that works for you, or know what the average temps will be so you can be prepared). Some was incredibly helpful (and I've gone ahead and listed the helpful info below). Most was totally useless.

And the silly thing is that one of the most common things I read before the hike actually was the most useful thing, but it sounds totally useless.

Hike your own hike.

Really, this cutesy little phrase should just be 'live your own life' and everyone should follow it and no one would ever be afraid to take big chances and live the life they want to live but since that might not happen anytime soon, let me relate it back to the Appalachian Trail.

I believe that the only thing you need to do to successfully complete a thru-hike of the AT is to hike your own hike. Yes, a 15 pound pack will put less wear on your knees (so if you have busted knees, the hike you should want to hike is one that's kind to them), but you don't need anything specific to be successful other than the right mindset and a willingness to let your hike be the hike you want and need. This is a big deal on the trail and in life.

Hike your own hike is probably the most common phrase I heard on the trail, and also one of the least followed. Akin to 'be yourself' in regular life, people loved saying it but were really concerned about what everyone else was doing and what everyone else thought about what they were doing. I met people who had spent their whole life dreaming about hiking the Appalachian Trail and then spent (seemingly) their whole hike fretting over whether they were doing it 'properly'. The idea that there is a right way or a wrong way to do it blew my mind the first time it became clear that there were a lot of folks who believed there was a proper way to do it. People were obsessive about critiquing other folks on their choice of gear, their choices for mileage, anyone who believed something different than they did about slackpacking. Basically, anything you believed that didn't jibe with their belief, they'd be sure to let you know they thought you were doing it wrong. And did many of these folks probably hike the Appalachian Trail? Yup, I'd guess about a quarter of them finished (well, maybe less), but they didn't get as much out of it as they could have, I'm certain of that (the same way I'm certain that folks who constantly criticize others aren't getting as much out of life).

See, life isn't about what other people are doing. And I understand that it's really difficult to acknowledge that because then you have to look closely at what you are doing and determine whether or not you respect that. It's a whole lot more work to improve yourself than it is to criticize someone else and remain stagnant (I know, I've done it before). The thing is that you gain nothing when you do that.

Hiking with my girlfriend was certainly a different experience because you can't completely hike your own hike when you're with someone else every moment of every day. The phrase managed to be just as meaningful (if not even more) for me because it made me realize that I needed to respect and try to understand where my hiking partner was coming from at all times, and I also needed to not sacrifice my needs. For us, it was a matter of hiking our own hike, and really, because we didn't waste much time judging each others actions, we were able to do just that. We were able to because we hiked the hike we needed to.

Are we special? Well, I don't want to sell us short but not really. I mean, we don't have genius smarts and we're not pro-athlete fit, so other than hiking our own hike, why were we able to finish something that such a small percentage of folks finish?

Well, aside from the fact that an alarmingly large number of people who start at Springer Mountain are totally inappropriately prepared mentally and/or physically for the hike even in the smallest possible ways, it also has to do with attitude. The hike isn't a ton of fun all the time. It's a 2,186 mile walk. Humans haven't been doing walks that far a really long time and there's a reason for that - it's physically demanding and incredibly monotonous. And so the most valuable thing you can have isn't the perfect sleeping bag, or the sweetest looking ultralight pack, it's a positive attitude.

This year it rained...a lot. And that isn't always so much fun, being out in the rain day after day. In order to be alright with that it really helps to be able to summon a positive attitude on a daily basis. That doesn't mean you have to love parts of it (if you love every minute of it, you should probably just move into the woods because you belong there), but you have to find parts of it that you do love all the time or you'll not likely make it without some serious help.

When we finished, I was pretty excited to return to a life of incredible comfort (I don't think people realize how good we've got it here). I was sad to know that I'd be parting from some terrific friends that I made along the way, but otherwise, I was ready to return to teaching and my regular life. And I'm certain that it'll be a few years before I really am able to understand how this experience impacted me as a person, but I know that it helped me remind myself that whatever I really put my mind to, I'm able to accomplish. It also taught me a lot about myself and how I view the world and the people around me and gave me ideas on how to improve myself.

It also reminded me that anything truly is possible. The only thing that holds any of us back is ourselves - our belief in our abilities and our willingness to put forth the effort to accomplish what we want to in life.

And this life is your hike. So if you're someone who has always dreamed about hiking the Appalachian Trail, what are you waiting for? There is nothing that's stopping you from accomplishing anything you want, you just have to be willing to take a chance. Then, and only then, can you really start to hike your own hike, and I promise you that it's worth it.

(Incredibly helpful things to look up and do before you hike the Appalachian Trail - understand what weather is possible and have clothing that will keep you warm/dry/safe, make sure you know where to get food and have a good idea of how much food you need to stay full/happy, maybe go ahead and take a multi-day hike to see whether you enjoy it or not and if the stuff you have is reasonable to carry and works to your liking...that's about it).