So hard, in fact, that we have numerous words for it: persistence, consistency, grit, tenacity, resilience, perseverance, endurance, or what I like best: determination.
Often, difficulty is a telltale sign of something’s importance. So today we are going to talk about that, albeit from a very practical perspective. In particular, we will closely examine a commonly discussed tactic for sticking with things: streaks.
You’ve surely have heard of the popular method called Don’t Break The Chain (DBTC), where you mark off each day on a wall calendar with a big red cross, visually building a chain you strive to maintain as it grows longer. Many years ago, this idea went viral in productivity circles. But honestly, I’ve rarely seen anyone report exceptionally long streaks with it. If you have, please hit reply or leave a comment below.
It’s easy to promote an idea without any proof of its effectiveness. In fact, the origins of the method are questionable, and Jerry Seinfeld, to whom the method is attributed, even claimed he never proposed it. What’s more, if you look closely, “Don’t Break The Chain” is extremely simple—too simple. It’s incomplete advice at best, akin to telling a master procrastinator to “just do it” or advising someone obese to “just eat less.”
So, due to recent events, today I’ll share a quick musing on how I think streaks need to be tweaked to really make them work for you—or at least, I’ll tell you what worked for me to achieve a 1,000-day streak.
Spoiler: never breaking the chain is not nearly as important as quickly repairing it!
Leonardo.ai Prompt: A vibrant and energetic illustration of a person triumphantly standing in front of a massive, colorful calendar, with 1000 days marked in bold strokes, surrounded by floating productivity tools like pens, papers, and laptops, with a subtle cityscape or working space background, conveying a sense of accomplishment and motivation, the person having a beaming smile, bright, shining eyes, and an uplifting aura, with one arm raised in victory, and the other holding a cup of steaming coffee or a favorite motivational item, the overall style being playful, modern, and inspirational, with a mix of pastel and bold colors, and subtle textures, highlighting the idea of sticking to goals and celebrating milestones.
Two days from now marks an important milestone for me.
While it’s not as special as reaching the Enlightened level with Todoist, I’m still very proud. Here’s what will happen: I’ll hit a 1,000-day streak of completing my Daily Readwise, the daily review feature of the Readwise service.
Interlude
What Is Readwise?
Readwise is PKM middleware—it integrates countless tools in your PKM toolkit, allowing you to connect systems that wouldn’t otherwise work together. Specifically, it lets you automatically import your book highlights or notes on blog posts into your main notes app or personal knowledge companion (PKC).
The power of Readwise lies in its support for many sources and destinations. Most of my highlights come from analog books, PDFs, and blog posts. However, I also use my Kindle, Twitter, YouTube transcripts, and even podcasts—all of which are supported! Once set up, all your highlights are channeled into Readwise and then synced to your PKC. In my case, that’s Obsidian, but Readwise supports almost all popular note-taking tools on the market—from old dinosaurs like Evernote to newer tools like Tana or Heptabase. As new PKM apps emerge, it’s safe to assume that support will be added for those that gain traction.1
However, Readwise is more than just middleware. It offers additional features that many users don’t utilize. One of them is the daily review of highlights.
What is The Readwise Daily Review?
The Daily Review feature of Readwise selects random items from your entire repository of highlights and presents them in a spaced repetition format.
The Daily Review feature as shown in the Readwise Dashboard.
The Daily Review can be configured in various ways: you can adjust the number and recency of highlights, choose whether to include supplementary highlights from books you haven’t read (but others have highlighted), and exclude low-quality highlights made by mistake.
During the review, each highlight is presented as a card. From here, you can discard highlights, tag them, or add them to your favorites. You can also edit and progressively summarize them and share them as images.
A plain highlight that I am presented with the first time as indicated by the blue dot next to the book cover.
The same Readwise highlight, marked up with bold font and color.
The same Readwise highlight, with added personal notes.
The same highlight ready to be shared as an image.
For the last 998 days, I’ve consistently completed my Readwise Daily Review. The day after tomorrow marks the 1,000th time I’ll do that. I can’t think of anything else I’ve done so tenaciously and for so long, so I thought it’d be a worthwhile exercise to contemplate how I managed to reach this milestone in this particular case. Here’s what I found.
Key Factors for Maintaining a Very Long Streak
The Scope Is Flexible
Completing my review takes minimal time—sometimes just a minute or two, depending on the highlights. I can adjust the number of highlights per day during stressful periods. I’ve had phases where I reviewed ten highlights, but recently, I’ve been doing just three (the minimum) due to other commitments. On vacation, I do the same. Fewer highlights help on busy days, and sometimes, you can lower the qualification standards to go through the review more quickly.
The Activity Feels Valuable To Me
I enjoy the daily review and see its value. Many of my highlights, especially from analog books, aren’t well-formatted and may be incomplete due to the OCR process, which can be error-prone. Cleaning up these highlights is beneficial. Additionally, resurfacing random highlights allows me to tag or add them to relevant projects. If I disliked the activity or didn’t find value in it, I probably wouldn’t have maintained the streak.
The Level of Gamification Is Appropriate
Not everything lends itself to gamification. For instance, I never cared about a streak in Todoist, my task manager of chode; the “number of tasks completed” doesn’t mean much to me. However, the daily review in Readwise is a perfect use case. The Readwise streak is well-balanced—not too intrusive but still motivating. There’s a visual representation of the streak in a calendar format and even a leaderboard where users are ranked. The dashboard provides a small visual reminder of the streak’s existence, which I think the Readwise team has executed perfectly.
The Grace Period Makes All the Difference
The biggest reason I’ve kept up with the streak through sickness, vacations, and stressful periods is the grace period. Initially, this didn’t exist; missing a day would reset your streak to zero. This happened to me a few times when I had streaks over 100, which was frustrating, especially when there was a good reason for the miss.
My Readwise Daily Review Streak Overview from May 2020 - Feb 2021
My Readwise Daily Review Streak Overview from Feb 2021 - Nov 2021
The Readwise team must have realized this, and so, at some point, they added a way for you to recover your streak. Whenever you missed a day, you could now go back the next day and complete it after the fact to recover it and save your streak. Of course, you had to complete two reviews in a day, or even more, because the grace period is currently set to 7 days. You can recover everything from the last 7 days, but once you miss a whole week, your streak goes back to zero for good.
Some might say this is cheating since a streak is typically an unbroken series of events. However, if recovering a broken streak helps you get back on track, there’s no reason to condemn it. It’s similar to when I ran a marathon with minimal training using a “Run-Walk-Run” method, deliberately walking for a minute every 3 km. It got me over the finish line, my only goal back then.
Think about it: Recovering a 300-day streak after being sick or on a short vacation and continuing from 300 is far more motivating than starting from scratch. This even holds if the reason for your break was simply that you forgot to do it. So, I believe making the streak recoverable was a genius move by the Readwise team.
Summary: Designing a Successful Streak Strategy
So, if you are ever going to design a streak-based tactic for yourself, here are a few guidelines you can follow (at least I will do so, as I believe them to be genuine):
Choose an activity that is valuable for you to perform indefinitely.
Select an activity that you like or at least don’t dislike.
Ensure the activity is flexible in scope to accommodate capacity flux.
Opt for an activity where recovery makes sense and allow for a multiple-day grace period to maintain motivation over long periods.
Let me know your experience with streaks, and whether you think there’s something I should add to the list.
After writing this post, I felt inspired to explore whether streaks have been scientifically researched. Indeed, there’s evidence suggesting that streaks positively affect behavior. Most interestingly, a recent study examined “streak repair”—the ability to recover a broken streak. The study found that allowing participants to repair their streaks within their behavioral logs motivated them to continue engaging in the target behavior. While streak repair didn’t entirely eliminate the impact of a broken streak—perhaps because a repaired streak feels less authentic than an unbroken one—it still highlighted the importance people place on maintaining streaks. I wonder if this was the reason the Readwise team added streak recovery to their product. It shows that personal experience can often align with research findings. Now, I can somewhat generalize this effect to others.
P.P.S. — A Note on Readwise
Readwise is a paid service and isn’t cheap—it costs over $100 a year. They offer a 30-day trial if you’re interested. I’m not affiliated with Readwise, but I genuinely appreciate the team and their products. They also offer Reader, a read-later app for power users that’s included in a Readwise subscription. I’m happy to support them through my subscription and contributions, such as joining the Reader Beta program or writing this blog post.
Readwise Onesie — Tiny Reader, Big Dreams! I received this and other swa once I had reached a 800 day streak or so :)
Since PKM apps spawn these days like mushrooms after a rainstorm, some of the latest tools on the market may not yet be supported. The newest hype in the PKM community seems to be around Capacities.io, which feels like a fusion of Notion and Obsidian. Readwise does not yet support Capacities.io, but it’s almost certain that support will be added once the tool matures.
