If you got a beautiful journal for Christmas that you’re looking to start on January 1st, 2015, awesome! I don’t want to dictate what you do with it — I think keeping any sort of journal is worthwhile. But I am interested in the two most common failure modes:

1) Not knowing what to write about and being daunted by the blank page

2) Reading your filled journal, only to find its contents mundane or incomprehensible.

These two problems definitely feed into each other. If you feel pressured to write only things that will be meaningful later, of course it’s going to be harder to write! Here are some thoughts I have about identifying jackpot writing prompts: things that are both answerable now and interesting later.

One of my projects attempts to drill down the things that are commonly interesting but uniquely answerable.

As many of my friends approach their college graduations, I’m interviewing them about this time of transition. The finished products will be audio clips that are totally unremarkable now, boring next year, but hopefully unbelievable time capsules in 10 years. (I’m playing the long game here.) It’s like when you find what used to be your favorite jacket hidden in the back of a closet. You dig through the pockets; old receipts and some gum wrappers tumble out — the debris of who you used to be. I want the finished clips to sound just like that experience feels. A proper journal should do this too.

The secret? Things that might seem meaningless or mundane now reliably get infused with significance over time. On the flip side, it’s much harder to artificially generate significance. I can’t ask my friends questions that they don’t know the answer to yet: what’s most important about this stage of your life? what are you doing wrong? which of your relationships will last?

History demonstrates what journals can prove.

Historians might spend a lot of time on newspaper databases and Census records, but personal archives are always near the top in terms of potential. I’m working on a senior thesis now about the work of a fascinating lady, but most of her papers are inaccessible to me. That means that, despite all of my careful research, my writing is littered with instances of “it seems that” or “all signs point to” or “perhaps”. I cannot write “This happened because ___”. Having her journal would change that! Journals are smoking guns. People explicitly state their motivations, noting that their decisions were easy or hard, but ultimately came down to ___.

Does the digital age’s explosion of personal data change anything? I saw a fascinating discussion on whether social media reduces the need for archives. Here’s my takeaway: it is undeniably fun to look at Fitbit information, phone location data, email volume, or spending information, and to try and recreate your days from there. But this explosion in data doesn’t give us any information about intent. That’s what journals can provide! They’re places to record narratives about what compelled our actions.

I have kept tons of journals — many boring to reread.

I’ve tried so many different tacks over the years: gratitude journals, 5 Year diaries, a blog, countless apps. After painstakingly writing tens of thousands of words, I sit down to reread, eager to catch up with my former self. Most of the time, it’s way too boring! During one phase, I tried just writing down everything I did each day. That was something my phone could’ve told me! I also generally wrote waaay too much about crushes, which may seem all-consuming in the moment, but definitely do not make interesting reading. Here’s an actual quote: “Had an amazing conversation with you-know-who today!!” Unless this was a chat with Voldemort, which I think I would’ve remembered, I have no idea who I might’ve been referring to.

So, what works?

In the quest for an achievable, useful journal, I’ve generated some rules. Don’t try to ask questions you can’t readily answer — that’s a surefire way to get discouraged! Focus instead on things that you believe in and that might seem obvious now, but could change later on. The things you hold most important, your beliefs, your self-definition. I’ve got a list with 31 prompts like this in the next section.

History illuminates how and why we got to where we are. In its most potent form, a journal can do that for you, too! It can stage a conversation between past you and present you and finally, finally provide an answer to the everlasting enigma C.S. Lewis articulated:

Isn’t it funny how day by day nothing changes, but when you look back, everything is different?

5 Year Diary

In this type of journal, you have 1 page for each calendar date and 5 entries to a page. Here’s an idea: Take advantage of this layout and write about one topic on each date, so you can have a direct comparison of how you’ve changed over the years. Print out a list of 31 prompts, one for each day of the month. Be totally honest with yourself. Is each topic something you could see yourself writing about (12 times a year * 5 years) 60 times? If not, replace it!

Here’s a sample list that might be a good start for you.

Comment on:

1. the next thing you’re looking forward to

2. something happening in the news

3. your relationship with your family

4. what you’ve been watching

5. your hobbies

6. someone that inspires you

7. something you find funny

8. your health

9. something you’re worried about

10. your relationship with your coworkers

11. something you want to change

12. what you’ve been listening to

13. what you’ve been eating

14. your home

15. what’s going on at your job

16. something you’ve accomplished

17. a close friend

18. what you’ve been reading

19. a possession that’s meaningful to you

20. how you’d describe yourself

21. a relationship you’d like to improve

22. your neighbors/neighborhood

23. a routine you enjoy

24. a tough decision

25. something you’re learning

26. where you shop

27. your social network

28. something you find difficult

29. something touching

30. your finances

31. where you want to travel

Gratitude Journals

The rules are beautiful in their simplicity: Write down three things you’re grateful for, each night before you go to bed. Gratitude journals score incredibly well if you’re concerned about cost, ease, and effectiveness. It’s hard to imagine any habit that performs better across the board! They’re especially good if you tend to be very forward-looking, focusing on everything there is left to do and not taking the time to acknowledge how far you’ve come already.

One caveat: my gratitude journal was not so interesting to reread. Unless you’re a much more vivid writer than I am, this might be the case for you as well. That’s okay, though! I found that building the habit of reflecting and expressing gratitude was amply worth it in and of itself.

Take it to the next level: Have a close friend that you’re worried about keeping in touch with? Start a gratitude journal with them! Suddenly, you’ve got a built-in accountability buddy and an easy way of keeping up with the ebb and flow of their days. Phone calls each week or so can fill in the storytelling gaps of the entries.

Some Resources

StoryCorps has a list of questions.

I love using 750 Words as an online journal. It has stats and badges, if you’re into that sort of thing.

Here’s a 5 Year Diary I like and have gifted to friends.

Thanks

Header image: woodleywonderworks

5 Year image: DishOnDesignGal

Editing: @Anand Gupta