Friends in all the wrong places

Rebooting is a biweekly newsletter about using technology as a tool for empowerment, rather than productivity, so we can better tend to the things we love.

An enemy once told me that dating in my 30s would be harder than dating in my 20s. Thankfully, that hasn't been my experience. Making friends in your 30s, on the other hand, is a discouraging journey that I wish someone would have warned me about.

Recently, a year-long friendship came crumbling down over cocktails. A day after I broke things off with someone I’d been seeing, that friend and I met to grab a drink. I thought I’d be venting about my late-in-life realization that even being the person ending things hurts, but instead, I had to prep myself for another breakup. The story was barely out of my mouth before this friend grossly blurted out their attraction towards said person. Expressing my discomfort didn’t stop him from doubling down, responding with a quick, “Would it really bug you, though?” Dating is nothing when friendships are like this.

Thankfully, most of the people you encounter will be notably more respectful of common sense boundaries. Along the journey of friendship, you may realize you’re headed in a different direction than people you thought would always be in your life. You might also reconnect with people you never thought you’d hear from again, or find that a fun first date can turn into an even more fun friendship. I’ve learned it’s best to look at first dates more as an opportunity to meet new people, rather than the next chance to meet my soulmate—that search is on indefinite hiatus.

It takes some getting used to, and building new friendships requires a lot of work and vulnerability that even romantic relationships don’t always involve. I’ve had to wonder if the personality flaws I haven’t worked out quite yet will be deal breakers for new people who haven’t had years to forgive me for them. 

Since I’ve abandoned dating in favor of the hermit life, and am still trying to navigate the search for new friendships, I have plenty of time to catch up on my reading. I finished Britt Frank’s The Science of Stuck after mentioning it in my last newsletter, and it’s been instrumental in helping me break my old patterns and focus on things that truly matter to me, like spending more time outdoors with my pups, riding my bike, and drawing. Turns out, all I needed was a change in perspective to get back on track.

Breaking the habit

You might be aware that you’re avoiding your ever-growing to-do list, but it isn’t always easy to recognize the patterns and understand how to break them. As Frank says in her book:

In my case, one of my recent epiphanies was noticing that I go back to the same two depressing shows every time life gets hard, giving me something other than my own life to be sad about. They’re good shows, but it’s not healthy to let sadness stew for so long.

I took Frank’s advice and started picking up on the physical cues my body gave whenever I struggled to focus on something I’ve been meaning to get to. As I started listening, I realized that I’d put off things like writing outside of work, starting a new workout and diet plan, and reading more books, in favor of things that didn’t trigger my impostor syndrome or abandonment issues—like those sad shows I love.

Once that realization came into view, I found ways to assure myself those fears, while understandable, aren’t grounded in reality. The more validation I gave myself, the more those fears retreated. Suddenly, I stopped worrying that writing more would expose cracks in my capabilities, or that if I spent too much time focusing on myself, my friends would leave.  That’s when I finally started knocking things off my to-do list.

Going to the good place

Important as it is, emotional growth is only part of the journey towards getting things in order. All the affirmations and healthy outlets in the world can’t help you follow-up on all your unreplied emails or finish that writing project your friends have been hearing about for months. For that, you’ll need to find a way to restructure your digital life  to better suit the way you think and organize.

Bryan Jenks, a YouTuber who covers topics like knowledge management and note-taking, has built his entire knowledge system around making things searchable. “I don’t wanna file anything,” he says. “I just wanna connect everything together and then when I need it, I search for it. I never lose my shit.”

In my case, folders and unorganized stacks of files on my desktop can lead to a days-long endeavor of triaging all the things I’ve amassed as my scattered brain struggles to keep a grip of it all. I didn’t want a strict organization system that gives every file, every note, and every link just one place to live. Instead, I’ve developed a system that ties relevant things together and makes them searchable from a central place. That way, I can find everything I need without having to remember where I filed it.

For my notes (which I store in Drafts and Obsidian), I use a system of searchable tags to find everything relevant to a topic or project I need to dive into. If I search the tag “Rebooting” I’ll find drafts I’m working on or have published. And under “Rebooting links” I’ll find highlights from articles I may want to include in the links roundups, and I can add more tags to them like “AI” or “software” so those notes can live outside of the newsletter. I also tag things as “quotes” for things I didn’t write, and “thots” for original thoughts (the wording’s just a little more fun).

Whenever I read an interesting article in my read-it-later app of choice (right now that’s Readwise Reader), I add relevant tags that’ll get transferred into my notes after I read them. So even if I have dozens of articles tagged “software,” and I don’t remember an exact quote or where I read a piece of information, I can narrow them down with other tags like “iOS” or “subscriptions” to quickly get to what I want to read without endlessly scrolling. 

In my to-do list, I separate things by time, so I can search “1hr” for things that’ll take me an hour, and “15min” for things I can knock out in a jiffy. I can add another tag like “chores” to remember what I’ve been putting off around the house, or make tags for names of people related to a given task. Then, I search for multiple tags to find all tasks tied to a certain location and duration, or any other combination of tags I’ve created. 

Tags aren’t the only way to broaden the horizons of all the data you’ve amassed, but they’re the most flexible. Unlike folders, tags can be added or removed at any time without having to drag and drop, then remembering where your notes or other files went. If you need to switch from tagging things by duration to locations, like “work” or “home,” you can just change it without having to delete any preexisting tags.

Think of restructuring your digital life the way Frank describes moving past being stuck: “Getting curious about your behaviors (without shaming yourself) gets you out of stuck.” Once you reflect on the way your brain operates, and what’s causing you to avoid what you know you actually want or need to do, the doors to a more seamless digital life will swing wide open.

📚 Good Reads:

Push notifications are out of control (The Atlantic): A friend recently called me out on the fact that my phone’s always on Do Not Disturb, asking if it’s a power move to be the one making the call. I’m not self-aware enough to totally answer that question, but even if it is true, I also do it because I cannot stay on top of all the apps that have managed to find their way into my notification center. Amanda Mull writes:

So, if you downloaded an app for a store you frequently shop at, you might get a notification that your order shipped, but you might also get pinged to let you know about the latest, objectively irresistible deals you can’t miss. It’s not just our notifications, either; ads are even trickling into our settings apps. 

BlackBerry is a movie that portrays tech dreams honestly—finally (Wired): Most of my friends will tell you that I always have a show or movie to gush about, and that they usually don’t end up watching them. That’s fine, I can’t tell anyone what to do with their time, but I’m grateful to have met a friend earlier this year who can go on just as long about her favorite shows as I can about mine. We recently went to see BlackBerry, and I can’t recommend it highly enough. But don’t take my word for it, John Semley has a much more insightful take: 

Too much music (Maybe, Baby): Even on my days off, my body refuses to let me sleep in later than 7, and I’m usually up before 6. That used to be frustrating, especially after a night I stayed up too late watching Regular Show or plummeting down another Wikipedia rabbit hole, but I’ve learned to make the most of it. Most mornings, I like to make myself a latte, head outside with the dogs, and enjoy the quiet before the world’s awake. It’s just me, the pups, and the birds singing to each other. As much as I love listening to music, there’s no better soundtrack to wake up to than the song of a desert morning. As Haley Nahman puts it:

🌐 Just Browsing:

☎️ Voicemail refuses to die 🐶 Your dog doesn’t feel shame 🏢 The return to the office won’t save the office ▶️ YouTube videos that play nothing on purpose are kind of great 👾 The collectors who save video-game history from oblivion  👨🏼‍🎨 Where memory ends and generative AI begins 📲 Just buy the cheap phone, or last year’s model ✊🏼 Unions are good, and they might be our best defense against AI 👯‍♀️ How different cultures define "a good friend" 💻 AI is pretty bad at writing fanfic, and misses some of the genre’s essential components 📺 Screen time can be a tricky issue for parents, but it’s not all bad 🤖 Here’s how AI will come for your job 🐳 How to sink a yacht (if you’re an orca) ✅ Optimization is a sinkhole

🔧 Toolkit:

• When to just quit already

• How to save battery life on your iPhone

• Why you shouldn’t call the police on houseless people, and what to do instead

• The Arc Browser is my favorite new app, and it’s an excellent Chrome replacement for power users

• How to get started on journaling

👥 From the team:

• I wrote about everything I use to manage my ADHD

• Medea reviewed a heated mini massager that sounds awesome

💕 And now, here’s something we hope you’ll really like:

There’s no way to verify if the sourcing is accurate, but I recently came across a Henry Winkler quote that a Redditor said they’d heard when they met Winkler:

It seems like a Winkler thing to say, but even if it’s not, it’s a good thing to keep in mind. Your negative thoughts don’t define you, and neither are the feelings they bring about. Carry that sentence to something more positive and reassuring; you may just find yourself starting to get unstuck.

Also, here are some pieces about Barry that I’ve really enjoyed since finishing the finale (which, wow): Sarah Goldberg on Barry starting as a comedy, but ending as a morality tale about the choices we make. Barry’s message that “Those who deny their true selves will be punished, while those who endure the pain of seeing themselves with clear eyes will be shown mercy.” It’s also about the impossibility of redemption. Barry and Fuches’s relationship was the dark heart of the show. The show ends with the perfect crime. Henry Winkler talks about Gene's final scene. And here’s one of my favorite clips; I’m going to miss this show so much. 

As always, if you have any questions, feedback, or just want to say hello, drop a comment below or just reply to this email.

My thanks to Medea Giordano for editing this issue.