Rebooting is a newsletter about using gadgets and software as tools for empowerment, rather than productivity, so we can better tend to the things we love. It’s written by Jordan McMahon and edited by Medea Giordano
It’s always the questions you don’t see coming that devastate you the most.
After giving a friend a tour of my house recently, they asked me why my living room is full of art while my bedroom walls are completely barren. As I stuttered in place of answering, a twinge of anxiety told me that this goes deeper than not having time to go shopping. I had some reflection to do. My friend couldn’t help but notice my joy at this epiphany.
Later on, I ran a self-interrogation on why I’d let my empty walls remain that way for nearly my entire lease, even though I hate having bland rooms without decorations. I shuffled through explanations: I could be worried people would think I have bad taste (fair), that I’d be exposed as knowing an embarrassingly tiny amount about art (true), or that I wouldn’t find anything I’d like enough to keep on my walls for longer than a week. That last one stung, so I leaned into it, ultimately seeing that somewhere between now and my last art spree several years ago, I started to fear commitment. Not in the “I’m not ready for a relationship” sort of way, but in the “everything ends so don’t get too comfortable, even in your own bed” sort of way.
This bombshell was news to me. It made sense, though: ever since my grandparents died, I could never fully invest in any new relationship, friendship, or hobby (even if I thought I’d given it my all) as long as a part of me remained convinced that my default state would always be my lowest point.
Trouncing those fears is going to take more than a night or two of examination, and I’m working on it, but I’m already starting to see the benefits of that work. The anxiety of impermanence and the skewed view it’s given me haven’t gone away completely, but they’re less opaque. I’ve found myself less stuck in getting my work done and more capable of focusing on personal projects I’ve been putting off like fixing up my bike and writing a fictional story that’s been brewing in my head for ages. I still have the woes of ADHD to deal with, but I don’t feel the same amount of anxiety whenever I go to start a task, and inspiration is striking more than it has in the past couple years. That feels like a pretty good start.
What’s stopping you?
I doubt my friend expected a simple question to spark such a realization, but a few months earlier, I read Britt Frank’s The Science of Stuck, which dives into what holds us back from doing the things we actually want and need to do. I highly recommend giving it a read, but for brevity’s sake I’ll just say that anxiety and fear of facing our problems play a big role in keeping us stuck in cycles of procrastination. For all the talk about the problems with using phones and social media as escapism, Frank suggests looking elsewhere when trying to curb your habits. “Tech is more of a symptom of the human condition than the source of our problems,” she told me in an interview.
Avoiding the stress and pain of our lives isn’t a problem on its own. As Frank says, “Escapism is healthy up to the point where you stop feeling like you’re making a choice; if I’m on my phone for hour six, but I really want to be writing something, I’m no longer in choice, so it’s no longer healthy.” If you’ve ever found yourself on the tail end of a long, retina-burning TikTok session that you promised was only going to last a few videos, you can probably relate.
Unhealthy habits can be broken, though. The starting point, Frank says, is to get curious and be honest with ourselves about why we’re avoiding the things that truly matter to us, and then deciding what you’re willing and able to do about it today. If that's not a dang thing, Frank says that’s totally fine, maybe tomorrow will be different.
While it’s not as easy as just finding the answer and getting to work, Frank has a solution that’s been instrumental in my project of getting back on track. In her book, she introduces the concept of micro-yeses—the smallest possible step you’re willing to take towards a goal or project. If you’re not doing it, she says, make it smaller. If you’re trying to curb your social media time but can’t seem to make it stick, she suggests interrupting the cycle by doing things like standing up for 30 seconds, or even just taking the time to acknowledge that even though you know you should stop, you don’t want to, and asking yourself what purpose that avoidance is serving. “Everyone gets so focused on behavior modification, we forget that these addictive behaviors in our tech serve a function,” Frank says. “If you don’t identify the function, it’s unlikely you’re going to modify your way out of excess tech use.”
She also says that rather than taking an all-or-nothing approach to unplugging or detaching from your tech, consider the harm-reduction model. You may not be ready to end the habit of scrolling for a few hours after work, but maybe some of that time could be spent scrolling through articles of interest rather than the ever-enticing For You Page.
Have it your way
If you’re unsure of where to start with breaking your unhealthy attachment to your apps or gadgets, Frank suggests taking an honest inventory at the end of the day. Specifically, she says looking at what you’re doing rather than how long you’re doing it (sorry, Screen Time) will tell you a lot about yourself, what you’re struggling with, and why you’re dodging it.
You can take that any way that meshes with your brain. For me, what’s helped the most is adding everything I have to do into my to-do list, being diligent about adding due-dates, and forcing myself to add a note to any task I defer to a later date explaining why I’m putting it off.
Frank emphasizes the importance of leaving shame out of these examinations, so keep that in mind and be sure that you’re using these questions as a way to find solutions to your problems. Don’t use them as a way to validate your own fears and anxieties.
There’s no magic app that can solve these problems. While tech can be a great tool of empowerment (that’s the whole thesis of this newsletter), it can’t be the direct solution to the problems it introduces. Your note-taking apps won’t make you smarter (ask me and my iPhone’s 236 apps how we know), and searching for the perfect tools to get work done can be a distraction all on their own. If you’re spending all your time downloading every to-do list or note-taking app, Frank says it may benefit you to ask yourself how the disorganization you’re trying to alleviate is benefitting you, then building from there.
Apps like Goblin.tools can automate a form of micro-yeses by breaking tasks down into smaller tasks, but Frank says one of the keys to making these changes stick is slowing your brain down to examine the issue at hand; a robot can’t do that. Still, it can be a good place to start, so if you do go that route she recommends breaking the tasks the app gives you into even smaller tasks. From there, pick three to get started on. That way you’re not overloading yourself with tasks and can still take some pause to consider what’s really getting in your way.
“It’s hard to ignore painful truth: tech can help us access truth, and it can help us avoid and deny truth,” Frank says. “Both are really powerful, but one is helpful, one is not.” Once you’ve found out where it’s hurting or hindering your aspirations, you can get started on making it a tool that helps you rather than keeps you stuck.
📚 Good Reads:
Your project management software can’t save you (Wired): Matt Alston writes on how the labor practices of the industrial revolution continue to influence workplace culture today, to our detriment:
Workforce software is offloading the job of managing projects to countless mini-projects, each only as useful as the skill and utility of the individual user. And we can’t expect each user to be both a maker and a self-manager, especially with the imperfect tools on the market.
It’s true: most workplace tools alone aren’t sufficient for managing one’s own workload. Chances are, in addition to whatever systems your office has in place, you have your own task manager, planner, or system of Post-It notes that help you keep track of everything on your plate. These layers of complication add friction to our work, and can often make simple tasks feel overwhelming before we even get started. It can be easy to believe a new to-do list app can make your life more manageable—I just tried, unsuccessfully, to try Omnifocus for a week— but having the right practices is just as important as using the right tools. So, before you run off trying to find a new app or service to make work feel less daunting, figure out whether the fault lies within your own handling of tasks, or if the problem’s bigger than you. Don’t give yourself the work of learning a new app that ultimately can’t solve a problem that’s larger than you.
Rethinking “self-care” (Maybe, Baby): There’s been a lot of deconstruction of the notions behind self-care and its self-indulgent nature. No matter how daunting a task, or how stacked our workload may be, much of the advice seems to boil down to finding moments to treat ourselves between trudges of work, or simply finding new ways to look at and manage things. Haley Nahman gets to a larger point, that self-care is about more than just doing what we need for ourselves, it’s knowing when to lean on others, and when to offer support to those who may not know to ask:
The self-care myth is seductive. The calls to care for ourselves have never been louder, more urgent, more prescriptive, more convincing. It’s nice to imagine that with the right routine and the right state of mind we might single-handedly change our lot in life. The counter-intuitive truth is that the most productive forms of self-care—adequate rest, nourishment, agency—require a decent amount of social and economic support from our families, our bosses, our communities, our government
🌐 Just Browsing:
👻 What horror can teach us about grief and loss 🎥 Speaking of horror, The Fall of the House of Usher is here just in time for spooky season, and it’s very good 🎤 For good measure, some more Usher 🧠 A look at what our healthcare system gets wrong about concussions 💼 The youths love LinkedIn! 🚙 As the owner of a crossover, the case against them is pretty strong 💺 Fun fact: airline point-earning cards make more money than the airlines themselves 🏡 Cities are upset they can’t fine unhoused people for sleeping 💬 A friendly reminder that you don't have to engage in the discourse 🎧 A very New Yorker-y ode to audiobooks 🛹 Tony Hawk’s Pro Skater is as much about cities as it is about skating 🕸 This piece about how we browse the web made me miss StumbleUpon 🚽 Until one of the kids I volunteer with tried to explain it to me, I hadn’t heard of Skibidi Toilet, Gen Alpha’s YouTube series of the moment. It’s wild and hard to explain or understand, which is making some Gen Z-ers feel old. But maybe aging out of things isn't so bad 🧓 On that note, a good essay on the responsibilities of millennials as we start to age 🛩️ Farewell to small phones 🐘 I’ve avoided Twitter alternatives because since my hiatus a few years ago, I’ve forgotten how to post, but the case for Mastodon being pretty good is strong 🚦 It’s true, traffic is terrible ➕ A quick word on the benefits of going outside 🕜 A video essay on the tyranny of the clock ❤️🩹 The importance of convalescence 🛒 Self-checkout is terrible 💰 Thief Simulator sounds like a fun lil’ game ⌚ The new Apple Watch’s double tap gesture could be a big deal 📑 Being a serial tab-hoarder isn’t so bad
🔧 Toolkit:
If you like trying out new apps, but don’t want to deal with free trials or a dozen subscriptions, Setapp is a service that gives you access to dozens of premium apps for one monthly fee. I’ve been spending a lot of time in NotePlan and Ulysses
A rundown of all the new messaging features in iOS 17 (transcribe voice notes are a game-changer)
From this piece on writing as collage, Bernadette Mayer's writing experiments
👥 From the team:
I’ve long loved Kindles, but I’ve hopped on the Kobo train
I also replaced my bedroom TV with a tablet
Medea wrote about how to claim a refund for taxed period products
She also wrote a lovely piece about physical photo albums
💕 And now, here’s something we hope you’ll really like:
From Jordan: I’ve been obsessed with the Apple TV+ show, Foundation, for the past month. It’s based on the Isaac Asimov book (also great), and feels like a mix between Star Wars and Game of Thrones. The first season is a bit hit-or-miss (mostly hit), but the second season is excellent. Lee Pace’s performance alone is worth the price of admission.
From Medea: If you haven’t listened to Bad Omens yet, you need to. It’s been a long time since I’ve discovered new music and then become immediately obsessed, but fortunately/unfortunately, they’ve become my new hyperfixation and I’m only mad it took this long for me to find them. Their entire discography is worth a listen, but 2022’s Death of Peace of Mind is particularly great. Even if you don’t normally like metalcore, you might still appreciate the haunting beauty in Noah Sebastian’s vocal abilities.