The Weekly Review

by Chris Bowler

Can our digital tools help build habits?

Well, sure they can. I’ve mentioned several times here how I use a combination of paper and digital tools for journalling. And a big part of my journalling is tracking the activities that I want to turn into regular habits. That has been taking place on paper for me.

But I was recently intrigued by what Google has been doing with Calendar. If you use Google Calendar on your computer, you may not have seen what I’m referring to. An old post from David Kadavy recently resurfaced in my Medium feed (things must be slow). Titled What I Learned About Productivity While Working on Google Cal, he shares about Google’s acquisition of Timeful and how they were incorporating these features into Google Calendar. It caught my attention when I first read it and did so again.

The catch? These features have not been added to all versions of Google Calendar. Just on mobile.


The key feature is goals. On the mobile app, you can add 4 types of items to your calendar: events, reminders, goals, or an out of office period. Three of these are quite self-explanatory.

But the goals option is unique. With it, you can choose an activity you want to incorporate into your life on a regular basis. You tell the app how often you want to do it and for how long. It then finds spots in your calendar where the activity will fit.

Nothing terribly impressive so far. Of course, you could schedule in these things yourself (and if you don’t use an app for this, you should add them manually — things that get on your calendar get done).

Where it delights

I’ve enjoyed letting the app choose the days and times when I run. As I tend to look at my weekly schedule (usually a part of my weekly review) and pick 3–5 times myself, letting the machine do that for me has been a time saver. It’s just one less thing I need to do.

But what about when it chooses a time that doesn’t fit? This is what has made the tool a good experience for me so far.

First, I’m pretty flexible. So when I see that I have a run scheduled for the day, I don’t have to think about it much. If it’s a work day, I know it will happen around midday: I run on my lunch break and the exact time depends on booked meetings or my energy levels on meeting-less days.

Second, since the app itself can integrate with iOS’s Health app, I can just forget about the time. If GoogleCalendar chooses 8–9 AM for my run, I can run whenever I want, and the app adjusts itself accordingly.

Google Calendar, while poorly named, is nicely designed

You can see here that I ran around 12–1 PM. But while the event itself was originally scheduled for 8–9 AM, the integration ensures things are updated to reflect reality. And without me having to do anything. That’s a good experience.

Last, the app is supposed to learn from your tendencies over time and get better at picking those spots. I haven’t been using it long enough for that to happen, but based on the early experience, I’m betting it does this well.

So, can our apps help us build habits? Well, without the internal desire, no. But if you have a desire to change, then yes. By removing some friction and being adaptable, digital tools can help. I’m a big fan of Fantastical (it’s a great app and nicely ties together all my calendars from various sources), but I’ve been using both tools over the past few weeks.

I don’t see that changing any time soon.


3 ways to make the journaling habit stick

My most read piece on Medium is How I Journal. Since writing that, I’ve received a lot of questions about my journal, Day One, and how I put it all together. But there is one question that comes up more than all the others.

How can I start journaling and make the habit stick?

A lot of people see the value of keeping a journal, but struggle to fully adopt the habit. It’s very easy to try out an app like Day One, add several entries over a week, then forget all about it for a month. The world is full of empty paper journals with a couple of notes scratched into the first 3–4 pages.

So how does one adopt this habit?

There are plenty of good articles on this topic. And people like James Clear spend a lot of time talking about how to start a new habit. But as someone who has struggled with journaling regularly, I can share you with you what has helped me make this an almost daily occurrence.

Start Small

If you do not journal at all, envisioning yourself suddenly scribbling 800 words per day is not realistic. The best way to start journaling (or any other habit) is to start small.

This could mean a quick couple of lines at the end of your work day to sum up what you did. This would also apply at the end of the day before you go to bed, but you write about anything in life. Or it could mean adding a couple of images of your kids to an app like Day One without any commentary.

The important thing is to get started and to get some entries into whatever tool you’re going to use.

Use automation

One great way to achieve this very goal is to use some automation. There are activities you perform every day that can make good journal entries.

The perfect example for me is my reading journal. I have 5 journals in Day One, one of which is where I put quotes that resonated with me. I sometimes take pictures of a physical book I’m reading, but most of the entries are populated automatically without any work from me.

Using tools like IFTTT, I can populate my journal based on my reading habits. When I read an article in Instapaper, I can highlight sentences that I enjoy the most. A few minutes later, that highlight is added to Day One by an IFTTT recipe.

Quotes from Instapaper

I’ve done the same with my runs in Strava or my daily Fitbit summaries. The options are vast: your posts to Instagram, your tweets, posts to your blog.

With workflows like this, I’m building up a library of information that is of interest to me, but with no effort required on my part.

Review your entries

As I mentioned above, I have struggled myself to adopt the habit of journaling consistently. From 2012 to 2014, I wrote a lot of manual journal entries in Day One as a part of my morning routine. For whatever reason, I dropped that habit in the years after.

I still had Day One on all my devices. And when special occasions took place, I would tend to make a note or add some pictures. But I was not writing regular daily entries.

However, I was seeing the On This Day banner in Day One.

Day One includes this nice prompt to review all your entries for the current calendar day

And it was this banner that helped me see the value of keeping a journal. Every time I opened the app, I could see the 3–4 entries that had been written over the years on this specific day. The nostalgia from these captured thoughts and events immediately showed me how wonderful it is to have a repository for things your mind has forgotten about. Not every entry brings this feeling, but there’s value in the mundane daily activities as well as the special moments.

It’s all gold.

Over the past 3–4 years, I’ve persisted in increasing my use of a journal based largely on the value I’ve gotten from regularly reviewing my journal entries from the past. This is why starting small and using automation is so vital: you simply need to get some entries in there to see the value.

This is why building habits is hard. The return on the investment can take time. Even with Day One, you’d have to create a few entries and wait one year to see the value using On This Day.

So in order to see the value more quickly than that, force yourself to add some short entries, add some automation, then ensure you take some time to review what you’ve added.

Why Day One is so effective

I’ve mentioned the app enough times here already, but it’s worth pointing out why it’s so good. But let me state it plainly.

Day One makes it easy to get started, enables some nifty automated workflows, and even works well if you prefer a paper journal.

How I Journal now is a mix of paper and digital entries. But they’re all in Day One. When I sit down for morning devotions, my journaling starts in paper. But I always snap a picture of my notebook in a Day One entry. And my weekly review habit is also on paper, but each week also exists in Day One.

It's really the best option.

And that's how I've been able to keep journaling a regular part of my life over the last 8 years.


The Power of Regular Reviews

I’ve written about the value of regular weekly reviews before, even going back as far as 2008. It’s a key part of GTD or any other type of system you use to keep yourself organized. If you have a system that is not reviewed (and regularly), then you have a system you don’t fully trust because you can’t be sure that what’s in it is up-to-date and accurate.

Open loops are killer, yo!

After a lot of years of inconsistent weekly reviews, my using a paper notebook improved over the last two years enough so that this is now a regular habit. However, I’m finding value these days in even more frequent reviews.

The Daily’s

The weekly review is great for reviewing the whole picture and envisioning what a successful week would look like. You pull out 3–4 bigger goals you want to accomplish. But if you wait until the next week before you look at this once more, it’s very easy to get lost in the details and to miss your mark.

But if you take time to do smaller reviews, it’s a lot easier to ensure that your week does not slip away from you. And while any habit can be hard to adopt, daily reviews are quick and easy enough that they’re easier than making some big change.

Taking 10–15 minutes at the end of each day can bring a lot of peace of mind to your following morning.


One of the nice aspects of Things is the Anytime list. It shows you all tasks listed by Area of Responsibility and Project. You can quickly scan this list (quickly is relative — the time required is dependent on how many projects/tasks you have in there) to plan what to work on the next day.

Until recently, I did not make much use of the Anytime list and it’s been a wonderful addition to my workflow. And if you have a smart (yet simple) system of tags (review this article for an example of tagging in this manner), your can very quickly narrow down the Anytime to list to get to the important stuff.


As I go through my day, I send items to the Things Inbox. Towards the end of the day, I then open Things and process that Inbox. From there, I also review the Anytime list and see what items might fit well for my following day.

Again, this is not a long process — it’s nothing like a weekly review. But there is a lot of peace in taking a few minutes to check back in with my weekly review and ensure I’m still moving towards the goals I came into the week with.