Streak Stories

4,000 Days with Jason Shanahan

Introducing Streak Stories, a new series that celebrates Day One journalers and their recent milestone of consecutive days of journaling. Each interview features questions about how they built their journaling habit and their best tips for building a long streak. We also explore what they’ve learned from keeping a journal.

Jason Shanahan recently crossed the impressive milestone of 4,000 consecutive days of journaling. Jason, a teacher, is originally from Canada, but has lived in Hong Kong for the past fourteen years.

In this interview, we asked Jason about the importance of journaling and for advice on how to build a meaningful journaling habit that lasts.

How long have you been keeping a journal?

I have been keeping a journal in some form or another since I was eleven years old. Back then I would have been writing the old fashioned way with pen and paper.

I got my first smartphone in 2011 (a bit later than most people, I know) and Day One was among the first apps I downloaded. I have been using it consistently ever since.

I still like to write in longhand occasionally. There’s something about the tactile quality of putting pen to paper that I find aesthetically pleasing, but my Day One entries are my source material. I have all the raw information I need, and then I can polish it further.

What makes journaling important to you? 

My journal is the story of my life. We only live once, so journaling is a record of how I spent my time here. Even if I’m the only one who ever reads it, which is the most likely scenario, it’s important enough to me to make it a worthwhile exercise.

What do you usually journal about?

I usually write about anything that happens during the day that seems like it might be worth remembering. That could start with my recollection of the dream I had the night before, the commute to work, anything noteworthy that happens at work (more on that later), books I read, movies I watch, etc. I dine out frequently so I describe the details of the meals I have (more on that later too). I also make note of how much everything costs, so it’s been a useful way to monitor how prices have increased over the years.

“My journal is the story of my life. We only live once, so journaling is a record of how I spent my time here. Even if I’m the only one who ever reads it, which is the most likely scenario, it’s important enough to me to make it a worthwhile exercise.”

Most importantly, perhaps, is travel. I travel extensively to other countries (at least I did in the pre-Covid era). I’ve always been in the habit of keeping a travel journal. Day One makes that easier because I can make notes on the go without having to sit down and scribble something on paper. At the end of the trip, I can review all of the entries I made and compile them in a more presentable form.

When do you journal each day?

When writing by hand in a traditional journal, it would have to be at a moment when I have time to sit down at a desk and write about what happened during the day. That would typically be during the evening hours, or whenever I have a sufficient period of free time on my hands.

The beauty of the Day One app is that I don’t need to designate a particular time of day to use it. Thanks to the versatility of smartphones, I can make entries at any time of the day throughout the entire day. This can occur when I’m waiting in line for something, or riding the MTR. These are situations in which it would not be feasible to pull out a pen and notebook and start writing by hand, but with smartphones it’s not only possible but very convenient. I can jot down ideas the moment they occur to me so I don’t have to rely on my memory to recall them later.

What tips or advice would you give others who want to build a journaling habit?

I think the most important thing is to just do it. There is no need to overthink it or be preoccupied with setting things down perfectly. There are no rules to follow. There is no right or wrong way to create a journal. Just make it a habit and soon enough you will discover the style that suits you.

What have you learned from keeping a journal for over 4,000 days?

One thing I’ve noticed, particularly upon reviewing entries from years ago, is that it’s unwise to devote too much time and energy writing about annoying things that happened at work. These details cease to have any relevance once I switch jobs and am no longer at the same workplace. While it may have been useful to vent about certain frustrations in the moment, as a means of decompressing from a stressful day, these are the sort of details that are not necessarily worth preserving for posterity.

What is your favorite thing about the Day One app? 

My favourite thing about the Day One app is the search function. For instance, when I’m dining out, I can quickly perform a keyword search using the name of the restaurant. All my previous entries about that restaurant will instantly appear, and any observations I made in the past, like if one choice of side dish would have been better than another, it helps me make the right decision in the present.

I also appreciate the ability to export entries as a PDF. I usually do that at the end of each calendar year, creating a file containing twelve months’ worth of entries.

How has Day One helped you journal consistently for 4,000 days? 

The accessibility of the Day One app certainly helps. It doesn’t require any effort to pull out my phone and create an entry. Having something to write about is also important. It can be something as simple as an observation. At one point I had said to myself, if I ever have a day on which nothing interesting happens or there doesn’t appear to be anything worth commenting on, I would simply make that observation my journal entry for the day. Looking back over the past eleven years, I don’t believe I’ve ever had to do that. There’s always been something worth writing about.

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Did you recently cross a journaling streak milestone? We’d love to hear your story! Tell us your Streak Story here.

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