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Gender Update

🏳️‍⚧️ Today marks 5 years since I came out as trans on the internet . Time for a little ✨ gender update ✨. 💖 Check the release notes for all the details!

WWDC 2024 Wishlist

In line with tradition, I’ve compiled my wishlist for this year’s Worldwide Developers Conference announcements. I’m hoping for thoughtful integration of LLMs across the OSes, performance and reliability updates for core services, and the introduction of a few power-user tweaks and long-missing features. Some of these ideas have been inspired by others’ wishlists, and where applicable, I’ve…

Making Magic →

My wife Kate Sloan’s new podcast, Making Magic , dropped this week. It’s a fascinating ten-episode series about the history and impact of the world’s most famous vibrator . Plus, I make a special guest appearance in the first episode. Subscribe & listen now wherever you get your podcasts. And hey, if you like it, leave a review or tell a friend. 🪄

Under Construction →

What if something was designed one day, one change at a time? What if every day, it got just a tiny bit better? With time, revealed more of itself. A new project , where this website is redesigned one day, one rule at a time.

Absolutely Crushed →

In more mb -media news: earlier this year I launched a new podcast with my friend Syd Andrerson , called Absolutely Crushed . It’s a bi-weekly comedy interview show in which we gossip with a guest about their biggest celebrity or character crush and hilarity ensues. Imagine you’re at a sleepover with your closest friends talking about that hot person they have a crush on and lightly teasing them…

beestung Issue #12 →

I’ve been a fan of beestung magazine , a quarterly publication publishing poetry by nonbinary writers since I discovered it a few years ago. This week, they published Issue 12 on the theme of trans futures, guest edited by Cavar . I’m honored that two of my poems are included in the issue alongside fantastically inventive work by other nonbinary poets. It would a lot to me if you gave it a look as…

The Travel Focus Mode

Last summer, I visited Toronto to see my wife after being separated by pandemic-related border closures for months. While preparing for the trip, I realized that no matter how much I travel, it’s always a little stressful and now moreso with the addition of necessary safety measures like testing and vaccine checks. Add the difficulties of quickly finding boarding passes, managing delays, and…

5 Shortcuts I Use Daily

This Friday, I spent an hour and a half chatting with Matthew Cassinelli about using Apple’s Shortcuts app to simplify my work and life. We went through 13 of my 156 shortcuts, showing how they work, explaining how I built them, and answering questions from the chat. As promised on the stream, here are 5 of those shortcuts that I use every day, with a brief explanation of why they save me so much…

Stacking the Deck

PowerPoint presentations get a bad reputation. That’s because most of them are terrible —they’re boring, they’re too long, and they’re full of tiny text and awkward animations. On the other end of the spectrum, there are the highly-produced Keynotes from Apple that have been agonized over by legions of designers to sell you the company’s latest products. These decks are so intricate that they seem…

Software Paper Cuts

I’ve been using software every day for almost 20 years. I use it to do my work, create things in my spare time, socialize, relax, and so much more. And if you’ve met me or been reading this site for a while, you know I have very strong opinions about how it should be designed and crafted . But by far, my strongest belief about software is that almost no one pays enough attention to the paper cuts.…

Things You’re Allowed to Do →

This is a list of things you’re allowed to do that you thought you couldn’t, or didn’t even know you could. I haven’t tried everything on this list, mainly due to cost. But you’d be surprised how cheap most of the things on this list are (especially the free ones). I love this list from Milan Cvitkovic reminding us of the things we’re allowed to do but that we often forget are options. Some…

Are You Gonna Finish That?

I’m a completionist by nature. I love checking everything off my to-do list for the day. When I discover a blog , podcast , or webcomic I love, my curiosity pulls me toward consuming its entire backlog. I spend hours spelunking the archives, finishing every last morsel of media. Growing up, I attended Catholic school and was taught by nuns to finish my lunch because there were children starving…

How to Not Know Things

In May 2010, I was offered a job at the Apple Store at the King of Prussia Mall , one of the biggest shopping destinations in the United States. It was my first and only retail job, and in my three months working there, I became the top-selling salesperson (or as Apple called it, “Specialist”) on the sales floor (or as Apple called it, “The Red Zone”). I did this by sharing my passion, knowledge,…

The Case for “Mark as Unread” in Messages

For decades, email apps like Gmail, Outlook, and Apple Mail have all included a button to mark a message or thread as “unread”. But why? The software knows the message has been read; why is it allowing the user to override that truth and rewrite history? There’s a simple answer: it’s useful ! The unread state of messages in an email app controls things like the number next to the current folder,…

31<sup>st</sup> Birthday Livestream

Well, I’m doing it again. Last year for my 30 th birthday, we raised over $7,000 for charity on a super fun livestream. This year, I’ll once again be gathering some pals online and streaming Jackbox Games to raise money for The Audre Lorde Project : The Audre Lorde Project is a Lesbian, Gay, Bisexual, Two Spirit, Trans and Gender Non Conforming People of Color center for community organizing,…

Clockwise #430: Misinformation Tracing →

Clockwise #430: Misinformation Tracing I was thrilled to guest on episode #430 the Clockwise podcast today where we talked about the last apps we purchased, how we’d handle third-party payment options on our Apple devices, our experience with Exposure Notifications, and how we track our resolutions, themes, and habits for the new year. Give it a listen and let me know on Twitter what your answer…

Thought Technology

I was first introduced to the phrase “thought technology” by Merlin Mann and John Roderick on their long-running podcast Roderick on the Line . A thought technology isn’t quite the same as a belief or a philosophy, and it’s more than just a simple lesson. “ Keep moving & get out of the way” is an example from their first ever episode about how to best traverse a city. Thought technologies like…

Let’s Hang Out →

I’m an extrovert, and lately it’s felt so good to be able to see and meet people again that I want to do a lot more of that in the next few months. So, if you’re in or around New York, let’s hang out ! I made a cute little form to keep things organized. Don’t be scared, don’t be shy, come on in the water’s fine . ✌️

Uses This →

I’ve been reading Daniel Bogan’s Uses This ( née The Setup ) interview series since I was a teenager. They chronicle interesting people’s hardware and software setups and end up being a fascinating window into the subject’s priorities and tastes when it comes to tools and toys. My own interview just went up on the site, so now you can read all the nerdy details of my setup. Let me know what you…

Software Sommelier on Clubhouse →

A few years ago, I let folks on Twitter ask for software recommendations for any problem they need solved with an app. People loved it and I loved helping people find the perfect software solutions to their quandaries. This Friday at 3 PM ET, I’m experimenting with a version of the same thing on Clubhouse co-hosted by my friend and colleague, Jillian Meehan . It’ll be be a fun, nerdy time and we’d…

2021 Theme: Invest

My 2021 yearly theme is Invest 📈. Spend time, attention, & money on things with potential. 🕰 Build systems, relationships, & habits to last. 🏛 Evaluate bets consistently and adjust. ⚖️ Last year’s theme was about making commitments. Getting married was one of them, but so was writing more consistently on my site. This year builds on those commitments with a focus on things with longer…

Birthday Stream Thank You

Thanks to everyone who dropped by the livestream last night and donated to Trans Lifeline. Thanks to the generosity of 108 of you, we raised $6,963 to help trans people in need. Best birthday ever. 🏳️‍⚧️🎂

30 Lessons from 30 Years

I turned 30 years old today so I spent some time this afternoon reflecting and collecting 30 lessons I’ve learned in my time on earth so far and (as best as I could remember) where I learned them from. Merlin and Roderick sometimes call these types of lessons “thought technologies” and that certainly feels fitting considering how useful and applicable they’ve been for me. Each one of them has…

30<sup>th</sup> Birthday

This Wednesday, December 30th is my 30th birthday! (It also happens to be my golden birthday .) While normally I’d spend it with friends and family, the pandemic is making that pretty difficult. So instead, I’ll be gathering with my pals online and streaming Jackbox Games to raise money for Trans Lifeline . Join us on 12/30 at 9 PM ET over on Twitch and donate here .

Ethical Design Guide →

Tech is always political. The way data is collected and handled is often biased, and many products are neither accessible nor inclusive. Ethical Design Guide is made to share resources on how to create ethical products that don’t cause harm. Sarah L. Fossheim just released this wonderful collection of resources (and monthly newsletter) on how to make digital products more inclusive. It covers…

Now Page Music

The now page now includes a playlist of music I’m enjoying lately called Heavy Rotation . In totally unrelated news, I miss Rdio .

Reasons You Aren't Updating Your Personal Site →

This was the first year in many that I managed to regularly update and publish content on my personal site. In past years I started strong (usually around New Years) with fresh writing, energy, and enthusiasm. But somewhere around February or March, things died off and I could never find that momentum again. Why was this year different? In this post I've tried to tease apart factors that made…

Clyde Common Egg Nog

For the last few years, every time the holidays roll around, I make a big batch of Jeffrey Morgenthaler’s Clyde Common Egg Nog for my family and friends. Since I won’t be seeing them this year due to the pandemic, I made a video showing everyone how to make it ( which Jeff seemed to like ). Enjoy! And let me know what you think if you end up making a batch.

How to Start a Real Relationship Online →

For Sloan and her partner, the answer became clear after the two spent a couple months together at the beginning of the pandemic because of COVID-related travel restrictions—and they decided to choose both. “I knew this was the person I wanted to marry, and I wanted that so strongly that the odd circumstances didn’t even bother me.” said Sloan. Though they’re still living in different countries…

Tone Is Hard to Grasp Online. Can Tone Indicators Help? →

Tone indicators are most popular within some Twitter and Tumblr communities of young people with overlapping interests in identity representation, anime and K-pop fandom, twee aesthetics, and sensitivity toward mental health and gender issues. It’s a milieu where inclusivity is considered a paramount virtue. These people use and like tone indicators because they want to help others have better…

Everyday Robots #63: Build and Watch →

This week I was excited to appear as a guest on the Everyday Robots podcast , hosted by Jonathan Ruiz. We discussed my career as an iOS developer, the making of Buildwatch , and the latest Apple event. Listen below or wherever you get your podcasts. Everyday Robots #63: Build and Watch

Buildwatch →

We launched a new app yesterday at Lickability . Buildwatch is a brand new Mac menu bar app for iOS developers that lets you track, graph, and analyze your Xcode compile times. I’ve wished this app existed for a long time, and now it does. 📊

Where Do We Go From Here? →

The latest episode of 99% Invisible details the history of and hopeful future for bathroom design. With a focus on the needs of trans and nonbinary people, Susan Stryker and the other members of a project called Stalled! have recently won a major victory in the International Building Code that will allow for better bathrooms for everyone . In her words: What I feel is so elegant about the Stalled!…

My Nonbinary Child →

If you’re a parent or thinking of becoming one, read this essay about my friend Sarah (they/them) and how their mom, who’s an anthropologist, responded when they came out to her as agender. I was already crying five sentences into this piece, but the conclusion is what really got me. I am thankful for their permission to tell a part of their story here. As I think how best to end this essay, I am…

WWDC 2020

Apple’s first online-only Worldwide Developers Conference is just a couple days away, and I’m excited to watch as many sessions as I can and chat with new and old friends in the Apple developer community. We’re even opening up the Lickability Discord server so we have a place to meetup and watch talks together. Come join us! This week, Apple is also under pressure from the developers of Hey and…

Black Lives Matter Resources →

Things are changing. People around the country are finally recognizing what black people have been telling us forever: that white supremacy, structural racism, and police violence are endemic in our culture, and it’s killing them. If you’re overwhelmed or having a hard time figuring out what to do right now, my friend Jillian Meehan collected this list of places to start. #blacklivesmatter

Jorge Quinteros: FaceTime Shoots Are Not as Bad as I Thought →

If there’s one aspect quarantine life has shown me is that there’s a wide orbit of things you’ll refrain from wanting to do because the results may not come close to what what you’re use to. There’s limitations. The quality may be different. Heck, the actual process of doing this new thing may require a different side of you that you probably haven’t developed yet and on top of that the people you…

Apps for All: Making Software Accessible

What does it take to build software that’s truly usable for as many people as possible? This morning, I’m giving a talk on this topic at App Builders 2020 . The presentation focuses on improving the accessibility of the software we build. Drawing on examples from the fields of architecture and design, as well as my experience, it explores the how and why of iOS accessibility in the broader…

Stand Clear of the Closing Doors Please

Stand clear of the closing doors please . This NYC subway soundboard app , by my pal Elle Lewis, made my day yesterday. If you’re a New Yorker, you should have this on your phone. 🚇

Perils of the Overworld →

I’m not much of a gamer, but I am a nerd about the creative process. As such, I’ve really been enjoying Robin Sloan’s new development diary newsletter where he is chronicling the creation of a game called Perils of the Overworld . Consider subscribing if you’re nerdy about maps, game making, typography, sound design, or interactive fiction. 🗺

Being Generous with Your Time →

There is no gate keeping, no screening, just a calendar form. I just show up to whatever appointments folks booked on my calendar with hopefully a little context of what they’d like to discuss. I don’t think I’m some industry pundit, but I do recognize that anyone who has been doing roughly the same thing for 10 years might be able to provide advice for someone earlier on in their career. Also, it…

Contact Page

In addition to the now page that launched last week, there’s now a short and sweet contact page with lots of ways to get in touch with yours truly. ✌️

Let’s All Wear a Mask →

On Friday, the Centers for Disease Control recommended that every American wear a face covering when in public. Masks will be the hot, bold look for summer. The medical evidence for the practice is overwhelming. The post-SARS countries in East Asia have known this for a long time, and America and Europe are finally coming around. I’ve put a bunch of resources about the medical benefits of mask…

Lickability Blog: Tooling at Home →

While there are lots of great guides on how to work remote from companies like Notion, Zapier, and Slack, we thought share some of the specific tools we’re using to make this easier for our team. Hopefully, if you’re a newly remote employee or manager, you’ll see something here that can help smooth out a part of your workflow. I wrote a new blog post over on the Lickability blog about the new…

App Critique: Learn Your Lines! →

As I mentioned the other day , I’m bringing back my App Critique video series, and the first submission is the app Learn Your Lines! from Andrew Cote . In this video , I walk through the app as a brand new user and point out some potential areas for improvement in the app’s UX and UI. Want your app critiqued like this? Submit it here .

xkcd: Pathogen Resistance →

This xkcd is exactly what I needed today. Well, that, and some pasta.

Now Page →

Since starting on the site redesign last year, I’ve known I wanted the website to have a now page : Most websites have a link that says “about”. It goes to a page that tells you something about the background of this person or business. For short, people just call it an “about page”. Most websites have a link that says “contact”. It goes to a page that tells you how to contact this person or…

App Critique

As I mentioned on Twitter yesterday, I’m bringing back a project I did in 2016 called App Critique 🧐. The goal is to show how I evaluate the design of software with short video design reviews. If you’d like your app design scrutinized, fill out this form . Preference will be given to indie devs and small companies.

MSCHF App →

The delightful weirdos over at performance art/tech company MSCHF just launched a new app. The app does what they used to do via text messages until the phone companies starting blocking their numbers: allows you to chat with them and sends you a notification every two weeks when they announce drop their new project. It’s good to see that even in a global pandemic, the crew over there will…

Helpful Engineering →

Helpful Engineering is designing, sourcing and executing projects to help people suffering from the COVID-19 crisis worldwide. We are an open community of volunteers without a commercial purpose. We believe that through a utilitarian approach, we can do the most good in the quickest time. Applying unused engineering and manufacturing resources, we can help the world cope with the threat of…