On the road again

How Apple Maps’s Guides gave me a way to safely go on adventures through town. 

Rebooting is a biweekly newsletter about how we can use technology to take better care of ourselves.


Nobody exits their twenties unscathed. There’s going to be some damage, whether it’s heartbreak, early career blunders, financial stress, or the general sense that you may not actually know what the hell you’re doing. The right therapist and a supportive crew of friends go a long way in recovering, but there’s no accounting for the traumas and insecurities a pandemic can uncover.

If not for the six months of quarantine I spent back in my hometown, it may not have occurred to me that since I moved away in 2017, I’ve struggled to make any other place really feel like home. Long Beach has come close, but my first year here was too tumultuous to really get much grounding, and I kicked off my second year right before heading back to Arizona. I tried to make New York work, but even a daily dose of the tastiest bagel I’ll ever get my hands on couldn’t save me from a city I wasn’t equipped to take on.

I only lived in San Francisco for about seven months, but that was just enough time for it to stake its claim as the only city outside of Tucson to ever leave me homesick. The novelty of living outside my hometown for the first time paired with the excitement of starting my career in journalism managed to keep a smile on my face as I clenched my wallet and tried to make ends meet.

There were certainly things I loved about the city—its chilly weather brought a welcome break from Tucson’s unbearable heat—but the Bay Area’s high cost of living meant spending most of my weekend behind the bar rather than exploring the town. It made for some good stories, and the pay was enough to keep me from stressing too much, but there wasn’t much time for me to do anything else. Even when I did have an hour or two to spare, it usually came after a Friday shift at my media job, followed by a closing shift at the bar. On the rare night that I didn’t embarrassingly pass out on my Lyft ride home, I usually tried to spend any free time I had tidying up my room and trying to get rid of the bar stench that had sunk into my clothes all weekend.

When I managed to squeeze in some free time, I tried to make the most of it by journeying into the city, camera in hand and a raspberry-flavored edible about to kick in. On my ride into town, I’d scroll through Spotify, queue up a few albums to shuffle through, and kick back until I found a good place to hop off. From there, I’d explore any areas I hadn’t been to before and peek into any shops or restaurants that caught my eye. Sometimes this led me to someone who suggested a spot where I ended up taking one of my favorite pictures. Other times, I walked away with a meal that, edible-induced spaciness aside, would’ve been unforgettable.

Those days didn’t come often, but some of my favorite meals, photos, and memories spurred out of them. More than my nights plopping into bed after working the last ten days, embarrassing first dates, or the adorable squeals my roommate’s pup made every time I walked in, those adventures gave me a sense of belonging in San Francisco that I might not have otherwise been able to get with the time I had.

Even though I’ve lived in Long Beach for about two years now, I’ve never lived in it during a pandemic, and my last few days back have been pretty weird. Kind smiles from passersby have turned into masks being quickly drawn over faces as they approach others, and stores just down the block have closed up shop and turned to GoFundMe for help. Even talking to my neighbor, a historically funny and good dude, has gotten difficult as he presses on whether I should be so worried about this pandemic at all. After spending the last six months back with my parents, being in Long Beach feels even less like home than it did when I first moved here.

Put a Pin In It

Edibles are easy to come by in SoCal, but the sense of adventure I found in San Francisco can be tough to muster up in the middle of lockdown. With stores limiting how many people can go into a shop at once, many places being closed entirely, and the risk of exposure being too high to just frolic about, that same kind of wandering isn’t feasible anymore. Good news, though! As long as you have access to Google or Apple Maps, you can recreate a bit of that sense of adventure and begin to (safely) navigate your city once more. Since Guides are new in iOS 14, I’ll be talking about Apple Maps, but you can replicate most of this in Google Maps if you so choose.

With Guides, you can make lists of businesses, landmarks, and really anything within Apple Maps, that are easily sortable by distance so you know how far you’ll be venturing. Like with any sort of lists, you could easily spend all day plotting how to best sort your favorite burger joints and local markets, but it wouldn’t do you much good. Given the current state of the world, I’ve sorted my Long Beach spots into three guides: Take Out, Delivery, and Essentials, and they cover all my bases for errands and munchie satisfaction.

We’re lucky that most restaurants in our neighborhood are being careful about their outdoor dining, but we’re still keeping that to a minimum. Instead, I’ve built my main guide around restaurants, breweries, coffee shops, and bakeries that offer take-out, and lumped them all together so I can sort by distance. This way, whenever I’m getting a craving for some sourdough but don’t want to have to ride my bike too far, I can peek at what’s open and how far I’ll have to go without doing too much on-the-spot Yelping. I also have guides for places that only offer delivery, and an ‘essentials’ list that keeps the places we need to visit from the places we may like to go.

That’s the boring part. The fun part—at least as much as this sort of thing can be fun while the world’s falling apart—is how you go about building these guides. Since you can’t really stroll through town, peeking in and out of restaurants until you find one that speaks to your tummy, you’ll have to do your adventuring from home. Still, it can be fun to browse through pictures of places you didn’t know were there, reading the menus and salivating over what might be your next tasty meal.

Instagram’s follow recommendations can lead you to a few good gems, too. If you go follow one of your favorite neighborhood spots, a little carousel will drop down suggesting more accounts, usually other restaurants, for you to follow. I like to spend a little while tapping through their stories, getting a peek at what sorts of tasty dishes they’re working on, and plotting out what I’d get if I were to order something on the spot. It’s how my girlfriend and I found a pop-up burger joint that only sells their burgers twice a week in the back of a coffee shop. Sure, I got us lost on the ride there and we were both pretty hangry, but a week later I’m still thinking about that breakfast burger, so the algorithm works.

If you want to get cute, you can make your own cover images for your guides for better association. I used some pictures I took last year in Long Beach, tossed some text over them in the app Over, and went on with my day. It’s a tiny change, but it makes the whole thing feel more official, and a little eye candy never hurts.

Before I Forget

To keep our exposure down, we’ve been making the most of our outings by grouping them together so we don’t make too many trips. It’s effective, but trying to juggle a bunch of errands at once can be overwhelming for me. So, if left unchecked, my flighty mind will certainly neglect a responsibility or two on my list of things to get done. Luckily I don’t live too far from any of my essentials, but few things can ruin a day like realizing you forgot to pick up your meds just as you sink into the couch and kick off your shoes.

I’ve been using Grocery, a beefed up version of Apple’s Reminders app focused on shopping lists, to keep me on task whenever I venture out past our quarantined walls. You can make shopping lists separated by store, and you can share your lists with roommates, partners, or anyone else you may be sharing your goods with. It’ll also keep track of everything in your fridge and pantry, even down to when things will expire. My favorite feature, though, is its location-based reminders. Whenever you arrive at your next stop on your errand run, Grocery will pop up with a notification to open that list, so you don’t forget it’s there. If you’re prone to forgetting your next destination, you can even set up stops along your path in Google Maps, so nothing gets missed along the way.

Back when I first moved here, it wasn’t uncommon for me to make my way to the local Von’s four or five times a week, and since it was only a five minute walk, forgetting something wasn’t too much of a hassle. I live further away now, and even if I didn’t it’s not worth the exposure risk. By having a list of everywhere I’ll need or want to go, and a way to automate getting the lists of things I need in front of me, I can make sure that my exposure to other people stays down, and I still get to feel like I’m going on a little bit of an adventure from time to time.

📚 Good Reads:

Evernote’s CEO on the company’s long, tricky journey to fix itself (Protocol): Note taking apps will always have a special place in my heart; back in 2017, in the application that got me my first writing job, I wrote about what my ideal notes app would look like. I’d hoped that by now I’d be able to have a single app that covered all my bases, and I’d be free of having to pick and choose based on my needs at a given moment. That hasn’t really panned out! But even if you don’t obsess over every feature a notes app has to offer, as more of us are stuck working from home, it’s good to know the state of productivity tools millions of users have come to rely on.

Evernote’s been in a weird state of being just-fine-enough to stick around, but barely. In this interview with Evernote’s CEO, David Pierce does a great job of looking at where Evernote’s gotten it wrong, how they’re trying to get better, and being realistic about how they’ll get there.

Facebook leaks show Mark Zuckerberg defending his decisions to angry employees (The Verge): With the number of stories Facebook becomes the center of, it can be tough to keep track of them all. Casey Newton’s piece from last week gives insight into Zuckerberg’s thinking, and how even the decisions that leave us with our jaws dropped probably have some numbers to back them up. And if you haven’t already done so, subscribe to Newton’s new newsletter covering social media, platforms, and democracy, Platformer.

On r/unemployment, Desperate People Seek Unemployment Help (The Cut): Normally, stories about communities finding solidarity and comfort would be heartwarming. Not when they’ve been brought together by the fallout of a government that’s failed them in the midst of a pandemic. As Bridget Read highlights, there’s power in being able to use these platforms to share useful information with others who are dealing with similar problems; you never know who will need your expertise in getting a management company to actually move on an issue.

The Hidden Costs of Streaming Music (The New Yorker): Alex Ross breaks down the points in Kyle Devine’s new book, Decomposed: The Political Ecology of Music. If you’re a Spotify user, this piece is absolutely worth a read. Now’s not a bad time to invest in a spec’d out iPod Classic

🌐 Just Browsing:

👉 iOS Shortcuts have gotten even better with iOS 14. Get started on Shortcuts, or beef up your workflow, with something from Matthew Cassinelli’s Shortcuts Catalog. ▶️ Patriot might be one of my favorite binge watches of the year. Its smart, hilarious writing and short-run make it an entertaining and easy watch. 📚 Looking for an alternative to the Kindle store or Audible? This Redditor has compiled a list of the best options. 🧠 Jordan Bowman over at The Strategist has a great roundup of the best mental health apps for BIPOC. 👀 The Markup explains the cost of “free” apps. ✏️ iPadOS 14’s handwriting recognition is a joy to mess around with, and I find myself using it a lot more than I’d thought despite it sometimes taking a bit longer than using my keyboard.🎓 What happens when you binge watch everything on Masterclass.📱 Hanif Abdurraqib has put together a project of the songs from 1968 to 2005 that most impacted his life, complete with playlists and great writing.

🔧 Toolkit:

I’ve been thinking about doomscolling and content exhaustion lately. With the news ramping up by the hour, logging on is a tiring experience. Since iOS 14 and related third-party app updates have released, I’ve been tweaking my home screen a lot. After way too many attempts at getting it just right, I found a way to fight back against that tired feeling while having a first screen that I don’t see changing any time soon: a reading screen. All I have on it is my highlighting app for quick note taking, my reading tracker, and a few news-related apps I can check in on when my brain’s hungry for stimulation that Twitter just isn’t suited for anymore. Try it out, you might feel a little better.  

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

A fun little reminder to bee kind.


As always, if you have any questions, feedback, or just want to say hello, feel free to drop me a line on Twitter.

My thanks to Medea Giordano for editing this issue.