Checkpointing.

Checkpoints are ubiquitous in games. I grew up playing Roblox, and a popular genre of games I’d play was “obbies”, or obstacle courses¹. These had hundreds or thousands of stages, where your blocky character would leap from precariously angled platform to platform. You’d dodge the ’lava’ tiles and the rotating Wipeout arm, holding your breath until you landed safely on the spawnpoint, emblazoned with a sawblade icon. Sometimes, you wouldn’t quite make it: you’d clip the edge of an obnoxiously saturated red block. You’d teleport back to the previous checkpoint, groan, and start delicately maneuvering again.

Checkpoints in games were primarily used for saving the current state of the game to disk so the player can load it again in the future. I think most people expect savepoints in games nowadays. Games without checkpoints, like Bennett Foddy’s Getting Over It feel extra frustrating: you make all this progress, only to not have any record of it and no way to get back to where you were before.

Productivity and mindfulness habits like journalling and weekly reviews bring video game checkpoints into our everyday lives. When you think back to the past year, what does your mind land on? Folks naturally fall back on the start and end of projects, new adventures, and major milestones as a sort of personal checkpoint in their life.

I think it’s fairly common for people to get caught up in the swing of things, jump from task to task, forget the wins they’ve earned, and end up feeling like they haven’t made any progress towards their goals and intentions at the end of the year (itself another checkpoint). Explicit checkpoints serve to highlight these landmarks, even if they’re not as grandiose as what one set out to accomplish. Just like Roblox obby spawnpoints, checkpoints give us a chance to appreciate the progress we’ve made and create opportunities for reflection. Checkpoints let us stop and think a little, before continuing to move forward.

This is a post about framing the ways we self-reflect as checkpoints. While forcibly gamifying productivity is usually a bit of a gimmick, the concept of game checkpoints is one that I think clearly maps to the way our minds center around past milestones.

Checkpoints as Deltas

Intuitively, checkpoints are like landmarks that demarcate single, instantaneous moments in time. The New Year might be a checkpoint. Graduation, finding your first job, or hitting a milestone of newsletter subscribers might be as well. They’re a natural way for your brain to keep track of time and organize events: checkpoint X happened, then next checkpoint Y, and so on. However, I also see checkpoints as a way to visualize progress. To me, checkpoints are more about recalling the deltas in between checkpoints — about reflecting on the journey, not the final destination.

If you’ve ever visited the visual, more artsy, Bullet Journal community, you’ll know about habit trackers. The Bullet Journal method is a popular way to organize your planning, and habit trackers are a common extension to the core ‘method’. Most folks create grids or bar charts each month with a row for each habit to track and columns for each day, then find creative ways to decorate their tracker throughout the month. Many have noted that the visual cues of the tracker and its presence close to their daily planning pages remind them to complete their habit, if only so they can have the fun of completing a tangible marker of progress. When you’re in between checkpoints in Roblox obbies, you want to keep going successfully through to the next checkpoint. With bullet journalling, habit trackers play the same role: people are motivated to make it to the next checkpoint, especially with such a visible reminder each day. Habit trackers serve as progress bars IRL, and the process of creating a new tracker for each month’s setup acts as a checkpoint.

Steph Ango’s 40 questions to ask yourself every year is another example of using checkpoints to reflect on deltas. I particularly like question 18: “Compared to this time last year, are you: happier or sadder? Thinner or fatter? Richer or poorer?” While these are shallow, arbitrary binaries, these questions tacitly invite us to think about the events along the year that caused us to turn out happier (or sadder) and why. Some questions are also rather targetted (question 26: “What was your greatest musical discovery of the year?”) so your answer might not be from the last few months. I find that I typically suffer from recency bias when reflecting, so questions like these helps to zoom out from the hot new discoveries fresh in my mind from the later bit of the year, to think about my mindset from the beginning of the year. Ango’s call for us to complete these questions each year makes the yearly habit a checkpoint and opens up opportunities to compare your life delta across years.

Checkpoints as Interrupts

A core idea of Daniel Kahneman’s Thinking, Fast and Slow is that our brains operate in two tracks: System 1, the impulsive, fast-acting mode that handles emotional reactions and quick decisions; and System 2, the slow, logical mode that activates when we do deeper thinking and visualize mental models. Our mind’s default track is System 1, and part of what Kahneman shows is that it takes some effort to engage System 2. For example, our brains often operate with inherent stereotyping (System 1), and we need to take conscious action and be aware of our biases in order to treat people fairly (System 2).

Productivity checkpoints, like the reflection activities mentioned above, are opportunities for this context switching to occur. It’s easy to run in System 1 all the time, but we need some System 2 thinking every so often to learn from our past mistakes. To borrow my operating system class’s terminology, checkpoints are hardware interrupts to let our System 2 software run. Checkpoints force a stricter delineation between your typical state of action and a reflective state of mind. Because checkpoints are like landmarks, they’re times for us to catch our breath, spinning down System 1 for a bit, which gives System 2 an opportunity to jump in.

Another common productivity habit is the weekly review. I most like Ben Kuhn’s take on the process: reading life advice essays that resonate and motivate you, review what happened over the week since the last review (a checkpoint!), then write on a list of impromptu and recurring prompts. Reviewing your progress and reminding yourself about your intentions and goals week-to-week is useful, since otherwise you often forget about your resolutions and get caught up easily in the daily monotony. Even small, granular checkpoints like weekly reviews can be useful — checkpoints aren’t just for yearly, exhaustive, or otherwise mentally ’expensive’ reflection.

Making checkpoints a habit curiously allows you to leverage your System 1 to shut itself down. By making checkpoints a weekly, recurring process, your System 1 can start to automatically internalize that it needs to let your System 2 get a word in edgewise. This is also why habit trackers seem so effective for folks: filling in the habit tracker becomes a habit, so it feels odd if you haven’t completed the habit and can’t tick the box.

Checkpoint Creation

While I was talking through the idea of this post with a good friend, they asked if checkpoints were encountered or actively created. I think there are examples of both. Birthdays, the start of a new quarter, and New Year’s are sort of societally imposed checkpoints. You don’t choose to pass them by: they’re stamped into your calendar as givens. These types of checkpoints are not actively initiated, but are still just as valid for checking in with yourself. As a bonus, their socially recognized nature makes you more likely to be in a thoughtful mood, making it less effortful for your System 2 to take over to reflect.

On the other hand, creating checkpoints via productivity habits for yourself is intentional. These require more activation energy to get started with and to build the habit for: you’re doing it for you, and no one is reminding you to commit.

One unique activity I see as a “created checkpoint” is applying to jobs and programs. I have a personal thesis that people should submit at least one application per year (swap out ‘one’ and ‘year’ for the frequency appropriate to your current life phase). Every time I fill in an application for something, I get to really dial in on my values and how they’ve changed since the last form I filled out. I take the opportunity to “Tell me about yourself” to think about what makes me me now, what made me me previously in my last application, and what’s changed in between. I add new lines to my resume, remove old ones to make room for new achievements, and reword bullet points to better match what I’m interested in now. Each application is one of my checkpoints, and even if I don’t get to see what I wrote ever again, I still find it a useful exercise in recalling how I’ve grown over time. If you choose to create more reflection checkpoints via this route, a nice side effect is that you’ll likely get access to some new resources and opportunities along the way.

Creating checkpoints should be done carefully and mindfully, though. Some checkpoints are more emotionally charged than others. For me, career-focused applications are a delicate balance: I try to be proud of what I’ve achieved recently, but find it hard to write about things effectively. (‘Effectiveness’ is also subjective here, and depends what my intention for the checkpoint is.) It’s hard because you have all the vibes and vague ideas of personal missions and ambitions in your head, but reifying that into words on paper is challenging. For opportunities I’m really excited about, I also naturally focus on my successes and spinning my experiences a certain way. If I fill in a form and realize I haven’t really done anything new, or that there haven’t been any recent relevant achievements, that can feel a little disappointing. This all puts some more stress into the process, which really shouldn’t be what checkpoints are about.

Conclusion

I think checkpoints speak to me especially because I’m so drawn to lists and neat organization. Framing my personal productivity habits as checkpoints helps me compartmentalize and create structure on which I can reflect. I surround myself with a lot of busy people — there’s a whole other discussion to be had on what the point of all this busyness is, but busy people in particular need checkpoints. I know all too well that being busy makes me go into whack-a-mole mode, where I’m just putting out fires for the day to day without thinking about my overarching goals. Little checkpoints, like trackers, weekly reviews, and job applications, bring a reminder of intentionality back to my life.

Maybe I’ll amend my thesis from above: people should create at least one checkpoint each year, just for the sake of having a checkpoint. Checkpoints should be about pushing yourself to break out of your usual cycles of work without taking yourself too seriously. Reflect on how you’ve changed and what’s fueled that change since the last checkpoint, and take a pause. Then, just like in the Roblox obbies of my childhood: keep going, keep growing, and keep making your way onwards to your next checkpoint.