I Journaled Everyday for a Year - How I Got Started

As long as I can remember I’ve wanted to keep a journal. I’ve never been able to keep it up though. Over the years I’ve bought a lot of fancy journals, only to have them lay around with only a few if any pages touched by a pen.

Sometimes I would have a pretty good streak, A week here and there but that’s about it. One time in 2017 I actually made it a whole three weeks. But that was my record.



So why did I want to journal? I wanted to be able to look back on what I’ve done, who I used to be, what I was thinking.

I didn’t expect it to help me so much in the moment. With my state of mind, my goals, and my self development. But it did.



How it started was really strange.

Last year I was thinking about buying an Ipad.

Now I’m very picky about my tech purchases, I don’t like spending money on non necessities, and I’ve spent the last few years as an aspiring minimalist, trying to simplify my life.

Adding another device to complicate it and probably just add distraction, gave me a lot of hesitation.

Still it did appeal to me, mostly because I do a lot of photography and being able to edit photos reasonably well in the field without lugging around my laptop seemed like a dream.


A quick side note: I know this is the epitome of a first world problem but I’m a firm believer in working on first world problems. I’m an optimist about humanity, I think we’re going to keep advancing and growing, if I’m right then very soon we’re going to have billions more people experiencing first world problems. So as someone who experiences these problems now, figuring them out is not wasted energy, and the root of this problem “over consumption” is a serious first world problem. So… so there. Now back to the story.

I was really conflicted about it, so I decided to write out a good old pros and cons list. As I started typing it out I was able to sort through a lot of my thoughts about it. Then I started to write about other things. Things that were going on in my life. It felt great.

I’m actually not sure when in the process I decided to start writing every day as a practice.

I didn’t write it down.

I think because I didn’t want to jinx it.



I started free-writing daily, at least one sentence everyday. Only one sentence by design, it’s such a small bar that it’s ridiculous not to do it. And the small barrier for entry makes it much easier to get started. Once I start writing, I almost always get into it and write more, I’ve only had a handful of one sentence days this past year.

I’m not at all embarrassed by those days, this was always about building a habit, not writing as much as possible.



The other thing I did is made sure I did it every day. When you have an unbroken chain like that, the longer it gets the more you want to keep it going. It also becomes a part of your routine. Humans love to form habits. Both good and bad. Good ones are often harder to make, but you can do it.



I go digital with my journal, while there’s something undeniably romantic about a physical journal. For me, taking it around everywhere is not something that I want to do. Having my journal in the cloud and easily accessible from any device fits into my life much better, and having it easily searchable has come in handy more often then I would have thought.

Now I do write in a physical journal every once in a while, sometimes it’s just nice, and I also like to have nature days and going camping. Part of that for me is unplugging from the digital world, so on those days I exclusively use a physical journal. Then when I’m back in the fake world I scan the pages and make a journal entry for those days.


I use Google Drive but there are a ton of services you can use. I honestly might switch soon. Because Google has enough of my data without me actively pouring my stream of consciousness into their servers. But Drive works great.


Another thing I use is a lightweight blue-tooth keyboard. I’ll throw this into my bag so I can connect it to my phone when I’m away from my computer. Does it look weird?

Yes absolutely.

Does it make free-writing on my phone nicer?

Also yes.

Now I’ve done many an entry with my thumbs, but when I have the keyboard, it’s nicer.

Don’t feel like you have to get one, but if you only have a smartphone you can get one of these for pretty cheap and I think it’s worth it.



This is my workflow, but if you want to start free-writing, try some different stuff. Maybe the physical journal is for you, that’s awesome! I honestly wish I did it that way. But don’t feel like you need a fancy journal or an expensive pen. I’d bet that right now you can come up with a pen and some paper to get started, and spending money so your future self will take goals seriously doesn’t work. If it did I feel like more people would actually use their gym memberships.

Just get the habit started however you can.



The two biggest tips I have for getting started and following through are:

1) keep the barrier for starting small. Just a sentence a day.

2) do it every day.

If you end up missing a day, it’s not the end of the world, but don’t go into this feeling like it’s ok to miss one. Go into it with the intention that you’re going to do this every day.

These tips also work for any daily practice you want to start. Keep it simple, easy to start, and do it every day.



After I had been free-writing for a while I successfully added more daily practices with these same principles. But I’ll save those stories for another day.



Trapezoidal Drift is also a youtube channel, and a podcast, if either of those are your thing.



Next time I’ll be going over the benefits I’ve found from journaling every day for over a year.



Thank you, I hope your day’s going great.



Oh I never did end up getting that Ipad. I might someday though, I’m still conflicted about it.