What I Learned by Keeping a Journal for 1000 Days Straight

An antique typewriter and a cup of coffee on a wooden desk.
Photo by Min An from Pexels

A few weeks ago, I got a notification from the Daylio app on my phone that I had submitted a journal entry for each day in the last 1000. Here’s how I got there and what I learned in the process.

It can be a tricky habit to form
Entries can be meaningful even when they’re short
Don’t make too many rules
Use whatever technology is available
Get reminders
A personal record is more than worth the time you put in
Work backwards when you get behind

This was far from my first foray into journaling.

I started writing longhand, stream-of-consciousness “morning pages” when I was 16. Inspired by Julia Cameron’s “The Artists Way.” I have often returned to this practice whenever I had something resembling a regular schedule, admittedly more often writing a single page rather than the recommended three.

But it was only about four years ago, around the time my older child was turning three that I decided to try to make a habit of writing a journal in the evening about what had happened that day.

I’d tried doing this a few times before but always stopped after a few days. I was hoping that a place to record, wonder at and complain about the developments and antics of my kids would keep me going.

It didn’t work at first. I wrote faithfully every evening for about a week, then dropped down to every other day and soon was only writing an entry around every week. This was certainly better than nothing but not what I wanted to have.

A child making a snow angel on a concrete basketball court.
Feb 27, 2021: Last day of our winter “staycation.” Cold and snowy. Kids made snow-angels on the nearby basketball court

I started my current streak while on holiday. It was July 17, 2018, and my family and I were about to fly to Canada to visit my parents. My first entry was simple and not very memorable. It’s obvious that we were understandably busy that day. But it was a start.

July 17, 2018: Last day in Berlin before flying to Canada

I kept going, making short daily entries, that sometimes grew longer. With no pressure to write more than a sentence, the streak of entries started to build up.

Three children looking down at a valley from a mountain lookout.
July 26, 2019: Rode the Sulphur Mountain gondola. Ate dinner at a restaurant with family and friends.

When I feel guilty that I can only manage to write a short entry for a day, I try to remind myself why I’m doing this. It’s for me, not for anybody else. OK, sometimes I look back and reminisce with my partner about some particular milestone in the growth of our kids — can you believe it’s been two years since he lost his first tooth? But mostly it’s for me. So I can do what I want.

Some people might strive for a consistent style in writing. Personally, I haven’t felt the need for this. Sometimes it feels most appropriate to use half the journal entry to talk about five minutes in a day while skimming over the rest. When I’m feeling like I want to write a historical document, or explain the day in bullet points or include a sarcastic rant, I do that.

Since I’m making the rules myself, I dropped the requirements for entries to be of any particular length. They could be just enough to trigger a memory.

May 11 2019: Took the rubber dinghy out into a lake with the boys in the afternoon. Went to a concert in the evening.

The important thing is to keep writing.

A large machine demolishing a building.
October 11, 2018: Busy day at the office. Lots of noise from a building being demolished nearby. Kids stuffed a duvet cover with every soft thing they could find and took turns jumping on it.

We’re lucky to live in an age with many options for creating and preserving our journal entries. Purpose-built apps on phones, emails to yourself, auto-transcribed dictation — many tools are available for cheap or for free.

Almost a year before I started my current streak of entries I tried using a service called “Trailmix.” For a small monthly fee, Trailmix sends you daily emails with the subject: “How was your day?” When you reply to the email, Trailmix stores the reply on its servers with the date that it sent the email to you. That way you can catch up if you fall behind. Trailmix also allows you to attach a photo, so you can build up an image journal at the same time.

I usually write my journal on my phone, either typing on the screen or, if I feel like writing a longer entry, with an external keyboard. I rarely open my laptop to journal because I tend to write last thing before bed.

Writing a journal electronically also allows you the opportunity to back it up in multiple places so that fire, flood or hard drive failure won’t destroy it.

A table with wrapped gifts, balloons and a cake. A banner above reads “Happy Birthday.”
Sept 15, 2019: Tina came for coffee. Kids had swimming lessons then went for ice cream. Prepared for tomorrow’s birthday party. The big present is from Grandma.

Emails from Trailmix also function as a reminder to write journal entries. As a bonus, they also send out the text and photo from a previous, randomly selected entry, giving you something to reminisce about and maybe a realization about how your life has developed in recent times.

But of course, most apps can also send you notification reminders, and if you’d rather journal on paper you could set an alarm for “journal time.”

I started my current streak when I switched to journaling in an app called “Daylio.” I’m certainly not the only Medium blogger who enjoys Daylio, and there is even a subreddit dedicated to it.

A grown-up and a child riding on horses through some woods.
April 2, 2019: Took the boys horseback riding. Visited the same restaurant as yesterday, and retrieved a toy that the kids left behind.

Daylio has some advantages over Trailmix, including the option to track your mood and activities. It also allows you to make multiple entries in a day. Daylio recently added the option to include a photo with your entry.

Using the mood tracker gives a nice chart of your overall mental state and the activity tracker allows you to see daily or weekly streaks in other habits. For me though, the most important thing is having somewhere to record and revisit the adventures and misadventures of our growing family.

My kids will never be this age again. We’ll all be lucky to get more than 29,000 days in our lives. It’s wonderful to have some notes to help you revisit some of the good and challenging times along the way. Getting to look back on what happened one or two years ago in the life of a young child is quite priceless already. To borrow the name of one of my favourite parenting podcasts, for our family this is “The Longest Shortest Time” and it will never repeat.

In terms of personal development, being able to look back at what you were doing a year ago (or longer) helps you to gain perspective on how far you’ve come. Penn Jillette, of the famous magician duo “Penn & Teller” is an advocate of daily journaling. Part of his daily routine is to look back at what he was doing one year, 10 years and 20 years ago. I would love to have that ability too.

A cat looking lazy with its head rolled upside-down, lying on a chair.
October 12, 2019: Lazy day. In the evening we took the kids to see an animated projection on a nearby building. They were more impressed by seeing the full moon and the big dipper.

There have been times when I’ve fallen behind in my practice. When this happens, I try to start writing early in the evening, before I get too tired. When I feel like I can’t remember many details of previous days, I start with the current day and work backwards.

This has quite easily allowed me to fill in blanks when I’ve gotten behind. So far I’ve managed to avoid getting behind by more than five days at a stretch. The biggest reason for this is, now that I’m used to regular journaling, I really miss it when I don’t find the time.

Two children sitting by a river near to two bridges.
March 27, 2021: Got up early and made bread with the kids. Went for a walk along the river.

I hope this helps you in creating your own personal record, whether for posterity, to help trigger memories or just to give you a good place to rant.



I like helping people to discover their own potential. He/him. Full-time parent & software developer, part-time teacher & musician.

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Stuart McLean

I like helping people to discover their own potential. He/him. Full-time parent & software developer, part-time teacher & musician.