What Do Your Journal Entries Look Like?

A new reader contacted me with a question about format: Did I write entries like a letter to someone?

I don't have a specific format that I use, although I don't start entries with "Dear…" I suppose I do have a few different ways of doing it though.

  • If I just make an entry, not for anything specific, it's generally in a prose, story-telling kind of style. "Today was ok, work was fairly boring, Susan picked the girls up from camp. They didn't want to leave the place, so much for worry about their homesickness…"
  • If I'm recording an idea then it might just start with a brief heading, and then the idea. "Idea for website: Dorkwagons.com – let people post pictures of silly-looking or badly parked cars."
  • I might do a drawing or a bunch of doodles. Not related to anything, except that I just decide to do them. 
  • When I write a long entry and I'm changing subjects, I'll write a squiggly line between the paragraphs – not all the way across – to denote that I'm changing subjects. Otherwise it reads very strangely later!
  • When starting a new day I draw a heavy line across the page under the last entry, then write out the date. If there's a holiday or some other event, I write it next to the date – Happy 4th of July!

The only bad format is one that makes you unhappy but that you feel obligated to use. It's your book that you're writing, so write it how you want to. 

If you have some old entries to read, go back and read them and see what you think of them. Writing in a journal provides half the value, reading old entries is where the other half comes from. As you read them, you'll quickly develop a sense of what works and what doesn't. The trick is that it takes some time to create enough distance between now and an old entry to read it on it's own merits. I'd say weeks rather than days. 

There is a bit of a knack to keeping a journal. Sometimes you'll do very well, sometimes not. It's ok. The book won't judge, and you'll learn and adapt and make it better. 

Business notes – loose pages or notebook?

Yes, I know. You’re looking at me thinking I’m some kind of luddite. Here we are, sitting in a meeting and you’ve got your tablet out and I’ve got my pen and paper.

Yes, I work with software, databases, and data visualization, and therefore I should be technologically adept. I am. I also enjoy reaping the benefits that come from writing notes by hand, including greater levels of attention and retention.

I invite you, dear colleague, to keep typing.

For the rest of you folks who also keep notes by hand, or are thinking about switching, and are thinking about how, here are some observations I’ve made over time.

There are a couple major ways to organize paper:

Loose pages

The vision of carrying a portfolio or slim briefcase filled with file folders and a few legal pads. This is a very flexible system, but there’s a lot of carry. Sometimes just a legal pad or portfolio will do.

  • Easier to file
  • Easier to scan into Evernote
  • Irrelevant pages easily skipped
  • Change paper at any time – lined, unlined, fancy, cheap, etc.
  • Really awesome paper is available
  • Hard to carry in small format
  • Not many folders/portfolios handle a large stack well
  • Easier to lose a page


I’m always attracted to simplicity, and one notebook is pretty simple. I’ve never made this work for me, at least not for everything I need, but I do still keep one at work and use it for some note taking.

  • Everything is in the notebook
  • Still scannable using the Evernote app, particularly if done every day. Tedious if a lot needs to be done – no auto feed unless you cut the pages out.
  • Nothing gets lost, no obligation to file anything
  • Not easy to file – tear out a page, or make a copy
  • Gathering everything related to one project or subject is not easy.

What works for me

I like a legal pad or blank sheets for free writing, working out problems, or noodling on an idea. I also use loose sheets for implementing David Allen’s Getting Things Done system.

I use a notebook for business journaling and some note taking. It’s easy to carry the notebook, and most meetings I don’t write much except a few action items. I know that if I keep things there I can find them later, which makes it comfortable in a way.

Evernote adds search ability

Sometimes I feel a sense of obligation to stick with one method or the other – have only one method – consistency is the hobgoblin and all. I’m finding that Evernote relieves any angst about which to use. When I put things into Evernote I know I can find them later if I look for them. When I remember to put them in Evernote!

It sounds great, but it’s not always as good as I thought it would be. The other day I was looking for an old project and searched Evernote. I’d scanned in my handwritten project list, so it should have been easily found but nothing was turning up. I found it, by hand, but Evernote didn’t.

Search ability isn’t everything

Putting things in a better system for searching gives the impression that all is secure, but it’s a false impression. Having things easy to find is only of value when I think to look for them. What about when I don’t?

Sometimes I don’t think to look for important things. I’ve forgotten them. Having them buried in some database doesn’t help that.

Right Place/Right Time As Critical As Search

Sometimes having a piece of paper in the right place wins over search. When I look in the file folder, there it is. This particularly true for subjects that I visit only occasionally, like strategy, ideas for the future, etc. I might fill a sheet with far out thoughts and ideas that don’t address any immediate issue. In the file it goes until I need to tap the well for new ideas. This isn’t the same for a notebook, where I’d have to be paging through in order to find it.

These notes are like stashing mad money in my wallet. When I need some ideas or inspiration, I check a file and find all sorts of things I’d forgotten about.

In theory I could put all the right keywords on it but words like strategy, idea, and innovation get used so much that I don’t think it would be workable.

Keeping notes vs curation

It’s tempting to go too far in thinking about business notes. To feel like everything has to be easily found, indexed and at one’s fingertips. Most of the time most of the notes I keep serve no one including me, and it’s pretty rare that a serious decision or action hinges on a note of mine.

The notes are for me to help me work better and they do. To do that they don’t need to have Google-like efficiency. Half the value comes from writing the notes in the first place.

When Do You End Your Journal?

I was catching up on putting volume numbers on my last few books, and I was thinking that my current BookFactory blank book has about 49 pages left in it. It’s been a great book, is in great shape, and has held up better than any other book I’ve owned. Time to decide what to use next. I’m pretty sure I would like to use another of these, so I ordered a new one to replace my current book when it is full.

I write in a book until I either fill it up or decide to use another one for a while. When a book is full, I give it a volume number and on the shelf it goes and I start the next one. I’ve been attracted to thicker books because they hold more stuff, I’ve always liked the idea of having more history with me.

The downside of this approach is that thicker books aren’t as comfy to write in, and I don’t really know when the book will be full until it nearly is. Sometimes that’s been at home, sometimes it’s been very close to when we’re away. I’d prefer it to be in the middle of a long boring period.

Here’s the problem though – I will fill the current book sometime around the end of summer if I keep going at my current rate. A time when we have a large trip planned. I’d prefer not to be leaving on the trip with a journal with 5 pages left in it. Now, there’s never a good time to finish one book and start a new one but it got me thinking – why not align it to the end of the year? Or Tax day? Or my birthday? Or whatever?

It would mean using a thinner book. It would mean leaving perhaps a lot of pages unused in years when I don’t write as much. A nice row of books numbered by year on the shelf would be pretty cool.

Is anyone doing it this way? How’s it working for you?

Prompts for a Good Journal Entry About an Adventure

A few posts ago I wrote about the struggle to journal adventure – How do you make sure you get these events written down for posterity when the point of the doing them is to have the adventure? I get frustrated with myself for not doing a good job with this, and I’ve been ponding ideas to get better.

I’m not one for journaling prompts. I’ve never used them. But it occurred to me that since journaling an adventure is often just about straight reporting, a list of questions would help shape the story and make sure I considered details I might have missed. So I wrote these down, and I’m planning to put them on a small card I’ll stick in my notebook. We’ll see if it works!

  • Why did you go on the adventure?

  • Where did you go?

  • How was the weather?

  • Who went you?

  • What did you do while you were there?

  • How did you get there?

  • What went wrong?

  • How did you resolve the problem?

  • Why would you do it again?

  • If you wouldn’t do it again, why not?

  • If you would do it again, why?

  • What did you bring that you didn’t use?

  • What didn’t you bring that you wish you did?

  • Did anything funny happen?

  • What did you learn?

What I Wish I had Known When I Started Journaling

If I knew then what I know now, what would I tell my past self about journaling, pen buying, and all the rest?

  • Start sooner. I didn’t start journaling on any regular basis until my 30’s. A lot of interesting years got missed!

  • Less angsturbating! Reading about my worries is interesting for a sentence or two. More is boring to read and hasn’t helped me solve anything.

  • Immediately write something any notebook I buy, to render it usable. No book that was saved for a special purpose turned out better than the others. The precious ones tend to not be worth the wait.

  • Buy fewer notebooks. Skip the stockpile. Shop, caress, investigate, but buy only when there’s a need. Of course, one needs to have a spare notebook in house.

  • Spend less money on pens. All the best writers I have were less than $200 and the ones I most reach for cost a lot less than that. Save that money for interesting things to do, conferences, etc.

  • Worry less about using pencil or water soluble ink. It’s all good. I haven’t ever lost an entry to water or malicious erasure, and the few that have been smeared (but still readable) add a bit of drama. It’s fine to think about permanence, I just can’t let it keep me from writing when I should.

  • Start the kids journaling early. No, earlier. Compared to the cost of medicine, toys, clothes and food, the cost of their notebooks is microscopic.

  • Start a journal for each kid when they’re conceived, keep it for them. Keep it up during their young lives with entries about them during childhood, and give it to them when they enter high school.

  • Write a lot less drivel about my stuff, or how I disliked this or that about my life. A few sentences here and there is more than enough.

  • Focus on the good stuff. Really, most importantly, this means the good side of whatever is happening. There is almost always a good side.

  • Draw a lot more.

  • Use less of the pocket Moleskines. When I moved to larger books, I wrote more, more valuable stuff, and I enjoy looking through those larger books much more.

  • Write more about what was going on in my life. Worry less about the quality of prose, worry more about capturing what happened. I have an entire trip to Europe that had barely a few sentences.

  • Write less. On a good day, when things went well but all I did was go to work, and nothing happened, it is ok NOT TO WRITE. When I just feel like writing but I don’t really have anything to say, the result belongs on a legal pad, not my journal.

The Struggle to Journal Adventure

Some of the best stuff I put in my journal is the stuff that gets written while on vacation or on an adventure of some kind.

The problem is that by definition, adventure is what a trip turns into when things aren’t going as planned. How to remember to write in the journal under those circumstances?

Heck, even when things are going exactly as planned, how do we remember to write? In the heat of something we enjoy, it’s hard enough to find a spot to sit and write, let alone take the time to do so.

This year I’ve resolved to do a better job. I figure this breaks down into three major parts:

Make sure the tools are there

It’s hard to write in a notebook that isn’t there with a pen that isn’t there, so both have to be there. The good news is that for you folks who share office supply addiction, this is the perfect chance to try new materials. Especially disposable or inexpensive pens, pencils, etc. Not to mention the many paper notebooks folks are coming out with. It doesn’t have to be your main notebook, although if that works, by all means!

Reminders of what you want to accomplish

I usually have no trouble getting the tools along. I’m a packrat when I hike, wanting to be prepared and all that. The big challenge for me is that writing and drawing take time, and are usually an interruption. There isn’t really a trigger for that. State Parks often put up signs warning you to stay on the boardwalk, or throw trash in the receptacle, but they don’t have signs saying “write this down”. I always convince myself that I’ll write about it later.

I need to remember what I want to accomplish. Now, I’ll probably never get quite as good as The Hike Guy (Go look at his stuff. I’ll wait… It was worth a look, wasn’t it?) but that’s the feeling I want. I can’t get there while sitting at my desk or in the car on the way home. I have to sketch a bit while I’m there.

Make it a priority

It has to be something I make time for. I have to tell the family that I want to sit down and write for a while. If no one else is drawing, then it can be pretty boring. This can lead to kibitzing, and I really don’t write or draw well in front of an audience. Particularly an 8-year old one that’s saying “What’s that word?” or “What is that supposed to be?”

I will bring spare notebooks for the kids, along with a few extra pens. I may not get them as engrossed as I will hopefully be, but it should work for a while.

It’s not a perfect plan

I’m still figuring this out, and the only family hike we’ve been on so far saw zero writing or drawing. I didn’t even bring a pen, let alone a notebook. I will have to do better if I want to get what I’m after.

How do you make this happen?