One thing I want to add to my previous post is my method for capturing screenshots. Since December 2017 I’ve used Droplr for taking screenshots. I haven’t seen anyone else use this method so I want to share it here. When I’m writing down todos in Things 3, or Apple Notes, I often need to include visuals along with those todos. But I don’t want to deal with inserting images inline, and I want to maintain the rhythm of my typing.  

I’m a product designer in my day job, and often in team meetings we share screens. If a teammate shares their screen, more often than not they want to reference another design idea, a note, a tool, a ticket, or some sort of visual. The conversation flows quickly, and often I only have a split second to see what they’re sharing before things move on. 

Outside of meetings I also have dozens of times a day where I want to reference something I saw, and include it with text I’m typing. 

I could record my screen constantly, so that I could search later. But as we’ve seen with the news from Microsoft Recall, I don’t think that’s ready for primetime. I’ve heard from others that Rewind has a lot of potential, and I may consider that at some point, but it doesn’t sit right with me yet. And it also doesn’t really fit with how I think and work. 

A second option would be to keep Zoom recording things during team work sessions, and check the video logs later. But that brings on a ton of friction, and changes the tenor of the conversation when we all know our words are being recorded.

A third option is to use some sort of AI bot to summarize the meeting. 

That’s not good enough, though. I don’t need just words, I need the visual context around what we discussed. If I was in a Figma file and saw a great idea, then a colleague dropped a link to an app with a specific screen in Slack, and then we referenced a ticket in Linear—well you can see it gets messy real quick. 

Words alone aren’t enough to convey that chaos. 

But, a tool like Droplr is perfect for this. 

Years ago I was lucky enough to get a lifetime license to Droplr, so I paid one time and haven’t had to pay again. I’m very thankful for that, and keep hoping I won’t get kicked off my plan. In case you’re looking for a similar tool, Cleanshot X seems to do the job just as well. 

Whenever I need to capture a visual on my Mac I’ll press my custom keyboard command (Shift+Command+3) to select an area of the screen. Next I quickly drag the area I want and let go of my cursor. This triggers Droplr (or Cleanshot X) to save that image, upload it to the cloud, and give me a custom URL. I paste that url into my notes doc (or wherever I’m typing) and have a visual I can reference or share with colleagues. The process takes two seconds, and I’m able to drop links to visuals inline with the words I’m sharing. 

It’s the perfect blend of words and images. 

Imagine I’m typing out a task:

“Move the button inside option A up beside the list in option B”

If I type that out on a Friday and come back to work on Monday I’ll have zero clue with that means. But if I took a quick screenshot of what I was looking at, and include the link; I suddenly have much more context on what I was thinking in that moment. So instead it would look like:

“Move the button inside option A up beside the list in option B [https://d.pr/f/exampleurl]”

This may look messy, but it allows me to stay in my stream of consciousness and pick up later if needed. Then, if I didn’t remember what the heck options A or B were about, I can look at the screenshot and connect the dots. 

This method is glorious. Whenever I setup a new computer I instantly install the screenshot capture tool. I’ve also tried every other tool out there (as of today) and these two are the only ones that meet my needs. 

For settings you’ll want to turn off any previews, disable retina images (it slows down the apps and upload time), don’t allow the image to save to your computer, make sure it uploads straight to the, and turn off any notifications.

The app should just quietly exist in the background, available at a moments notice when your shortcut is invoked, and not cause any visual clutter to your workflow otherwise. It all should happen so quickly that you don’t even skip a beat when typing out your thoughts. 

I took notes for a 30 minutes session today where we asked a user to review our app. During that session I included 17 inline screenshot links. That help to give context to what we were looking at and line it up to my written out notes. 

P.S. I also have a shorcut setup for annotations (shift+command+4), where I set the app to bring up its preview window with arrows and text, where sometimes I want to draw a big red arrow to the part of the screenshot I’m referencing; and include a few words. I need this far less; probably 5-10% of the time, but still find it useful enough to setup. 

P.P.S. Droplr is acting up on Sequoia if you’re on the betas. Cleanshot X just released an update this week, so it’s back to working. 

The only thing that’s worked reliably for me for more than a decade has been simple tools and habits.

I add items to a handful of bulleted lists, and pick a few to do that day.

After a lot of tweaking and testing of every productivity system around I’ve landed on something similar. I use Things 3 to list out my daily todos. At the end of the day I check everything off or (and in most cases) move remaining items to the next day or a few days later. 

If a todo item is more complicated, I reference a similiar named Apple Notes doc with more checkmarks on it.

That’s it. 

This system works for everything. Even work related items. If I have to track tasks in a company tool, such as Linear, I reference the ticket number in Things 3 or the related Apple Notes doc, and either check it off or move it to a future day. 

(Via adhdftw)

Over the last year and a half I’ve been growing out my hair. As I’ve learned there are a lot of ways to deal with messy longer hair. The simplest is to wear a hat. I’ve tried a number of different hats and don’t like how they fit and look. 

I recently picked up the REI On The Trail Cap, and love it. It’s got a shallow top, is light and breathable, and has a drawstring cinch on the back. It’s currently my favorite hat. 

Since Double Dap was announced I’ve wanted to use it on all my Apple Watch apps. Though it has some problems, namely that it has a lag and doesn’t respond as soon as I think it will, it’s a cool feature that I want to build a habit around. 

Because Apple is sometimes a bit slower to release public APIs on things, they’ve spent the last year allowing it on their own apps—and per WWDC’s announcement, plan to launch as a public API this Fall. I don’t know if the feature is actually good enough to really build into my way of using apps, but I’m intrigued to find out.

Most of my audio listening is done via Apple Music, Audible, and Overcast. That means 2 out of 3 of my top used apps on Apple Watch don’t benefit from Double Tap. I’m excited to see if I can actually use this feature.

I’ve struggled to figure out how to take things I like—such as great articles written by others—and how to save them. When I read something that stands out to me, speaks to me, I often look for a way to do something with that. 

Over the years this has led to me taking thousands of screenshots, saving into bookmarks, saving into the various apps I consume, and generally trying to store those things away. 

I’m trying a different tack now, something inspired by John Gruber. Whenever I see something interesting I save a link to an Apple Note. Over time that doc builds up with dozens, if not hundreds of links. Then, through the various podcasts I’ve hosted, or through my blog, I editorialize and publish my thoughts on the great things I’ve read.

It’s a calmer way of writing. I don’t have to force myself to think. I just go to the treasure chest of goodies I’ve saved over time, look through things, remix my own thoughts, and Steal Like an Artist. It’s a lot of fun. 

I don’t have a goal anymore of an article a day, or a specific wordcount. Instead I eagerly await the quiet moments where I can sit down and type out my thoughts. 

If, like me, you’ve been working in technology for a while, you’ve likely felt that tightening in your chest as ore and more news of layoffs and AI breakthroughs piles up. This feels different than before. I’ve been at this line of work for 17 years now. 

Shifts in tech have come and gone. I’ve been a web designer, graphic designer, illustrator, web developer, product manager, team leader, visual designer, and most recently a product designer (UI/UX design). 

When I meet people outside the tech space I tell them I design apps and websites for a living. 

The shifts in my work haven’t always been because I wanted them. Instead I modified my skillsets based on the overlap of work I enjoyed, what I was good at, and where I thought things were going. Oh and I wanted to make a decent living to provide for my family at the same time.

At one point I seriously comtemplated becoming a developer full time. But, half a dozen failed attempts I stopped trying and focused on what I was good at. 

So, I’ve managed to weather big shifts and keep moving forward with a mind full of curiosity, and have met amazing people along the way to work together with. 

I find myself watching the latest wave pouring in and wondering a few things. I wonder if this will hurt my ability to provide for my family as a career, I wonder if it will discourage new entrants into the field, and I also wonder if it will open up new opportunities that I just can’t see at this point. 

Where I try to land is that I know I can help others, and I enjoy making things. If I can continue to do those two elements, then I may be alright. Over the last few years I’ve focused my design skills more on the wide open and nebulous problem space, and less on the specific interface details. That may be a good thing. 

We’ll see what happens. Time to buckle up!

I’ve been away from work the last week, so I’ve been catching up on little bits and pieces of Config 2024. The biggest thing to come out of it, and the most impactful to designers, is the AI elements. I haven’t had a chance to test things yet; I fired up Figma and updated, but it doesn’t seem like anything is available on my end. 

Along with many other designers I felt this pit in my stomach catching the news of the AI features. It seems—again I don’t know until I test it—that the AI features will do basic UI things, along the lines of ChatGPT prompts. That’s not a concern for what I do as a designer, but it does have me wondering where all this is headed. 

For my part I focus on asking questions when I approach a design project. I am more curious about the problem a stakeholder is facing than immediately understanding any solution. Then I take that whole spaghetti of chaos and sketch it out, by hand, until I see something that starts to make sense. This is something I love deeply, and it’s more of the user experience side of design. That’s something I hope isn’t up for grabs by AI. If it is, I’d find myself rather sad. 

I’ll be watching all these new features and seeing where it goes, and am curious to see how other designers and business owners respond. 

At least I have my integrity. The machine may grind on, but I’m glad to have stepped off the treadmill.

Joan’s openness on the topic of being involved in tech’s greater whole is so refreshing. To feel hampered, unable to share the words you actually feel, to couch everything in a specific language catered to a specific audience, to always filtering what you think through the lens of ensuring it won’t cause problems—frankly it can get overwhelming. 

And for the first time in years, when I look in the mirror, I can recognize the person looking back. 

I’ve left out the far juicer parts of the post, and encourage anyone feeling stuck in the tech wheel to think through Joan’s words.

For me I’m trying to understand how I can continue to do the things I love, work with a few people I really connect well with, and make sure that I maintain that original nugget of care I had for this thing called design. 

I’m not at a point of leaving it behind, but I do think it’s important to make sure I’m taking time each day for the things that matter.

Nobody tells people who are beginners — and I really wish somebody had told this to me — is that all of us who do creative work … we get into it because we have good taste. But it’s like there’s a gap, that for the first couple years that you’re making stuff, what you’re making isn’t so good, OK? It’s not that great.

I’ve thought a lot about this quote in the last few days and have been blending it with another thought. People can be incredibly creative. You might be artistically minded in a way that the world recognizes, or in other ways where you mix words and communication and thought to inspire change. 

The piece for me, in all this, is finding a way to be kind and gracious while each of us strive to match our creative abilities to the taste we have in our mind. It’s hard, it’s a lifetime of work, but it’s worth it when you start to see your abilities improve. 

I’d also venture that taste morphs and twists and grows, and your abilities can follow it. 

We must be kind to ourselves and others in this journey. You can drive yourself to insanity thinking you’re not good enough, but you can also encourage yourself to keep trying, to keep pushing, and to find a balance between giving up and going crazy. 

(Via goodreads)

Things 3 is my main to-do list. Its design is simple, elegant, and fits well with how my brain works.

The funny thing (ha) is, Things 3 is not too dissimilar from Apple’s built-in Reminders app. The app’s layouts are strikingly similar; there are two columns: one for lists, one for tasks. The features are similar: both support lists, sections inside lists, “folders” (called “Areas” in Things), tags, smart lists, due dates, etc. And both apps have similar platform support, with each supporting iPhone, iPad, Mac, and Apple Watch.

I tried an experiment last Fall, switching from Things 3 to Reminders. I moved everything; but within a week had to move back. My life runs very tightly across Things and Apple Calendar (recently switched from Google Calendar) and I haven’t found a way to get Reminders to work the way I want.

I understand that’s part of the problem. If I want to use Apple Reminders I need to adjust how I think. I’m not quite willing to do that at this stage. Perhaps, like my switch from Bear to Apple Notes, whatever Cultured Code ships next may have solidify things. 

Via Andreas Reif

There are no ads, no engagement-thirsty UI patterns, no invasive interference. Just pure, uncut, personally-chosen content delivered in a calm, orderly environment. It’s the Marie Kondo method of information consumption – only content that sparks joy, delivered in a way that itself sparks joy.

I’ve wrestled with how to share and consume media, separate from the social media tech giants. I love Joan’s take on all this. Maybe it’s time to give Reeder another spin. 

Via Westenberg

Something changed in me today with my password habits. After over a decade of using 1Password as my default for account login management, I finally had a break in my habits. I went to create a new account for a piece of software, saw Apple’s suggestion for a new password, and chose to use it. This creates a split in where passwords reside. 

For so many years I’ve ensured that 1P is the source of truth; passwords are generated there, and my web browser can sometimes remember them and pick up on them, but at the end of the day I trust 1P. 

Now, with the new Apple Password app in MacOS beta, I’m second guessing my previous defaults, and wondering if the system password manager will be enough for me. 

There will forever be a struggle between the simplicity of a thing and how useful it is. I deal with this in software every day. I want something to be easy and I want it to do all the things I could dream of. Those two are, of course, complete opposites and generally impossible. Great design, and great software in the case of my own career, tries to strike a balance somewhere in the middle of these two. 

That’s why so many designers (in my own experience) are a fan of Apple. It’s not that they get this right all the time, but they often try and sometimes do figure it out. 

Productivity methods, no matter which you turn to, revolve around intentionality. It’s applying a system, a tool, or a practice to a thing that could be made better. More efficient. But if applied without intention, none of that will help a bit.

I’ve found that my ability to get something done is tied to more than just brute forcing something through. In fact, these days I find that nerely impossible. I can’t just make myself do better. It’s important to think more, to go on walks, run in the woods, drink water, sleep, and above all make sure I’m keeping my mind and body healthy.

When all those elements are in place I can then focus on a problem and figure out the best way to do it. 

Via tbr.

As a followup on the previous post, I’m feeling so disconnected from WordPress these days in terms of my ability to tinker.

Back in the day I worked very closely with my templates and files; editing things directly via Transmit in SFTP. Now with the new WordPress page editor I struggle to find where to change what. It’s all a mess. 

As a designer I want to modify a lot of things in CSS, while understanding the template system enough to tweak a tiny bit of the code. I’m intrigued by Kirby because it feels like a return to what I loved.

For the past year or so I’ve been on a journey to look at other options for publishing my writing. I’ve poked around with Ghost, Medium, and others. 

I am currently working on checking and adapting the Kirby CMS system to my needs. It is very possible that I will migrate in the near future, I just need to make sure it is something I want. I’ll write about my conclusions as to why I chose Kirby once I’ve done the migration. If I do.

My friend, Michal, is exploring Kirby. I may have to give it a try!

Right now my process involves writing in MarsEdit, and publishing to WordPress. I’ve been a WordPress user for a longtime now, going back to ~2006. I don’t know if it’s time for a change, but I want to make sure I’m exploring the best tools for how I work. 

Beyond the writing, I want to integrate things into an email newsletter. We’ll see how this journey goes. 

I’m excited about the passwords app from Apple.

As a 1Password user for years, I’ve love great password management and, controversies aside, feel like 1P has nailed it. 

I keep hundreds of logins locked away in my 1Password vault, protected by TouchID and a long safe password, known to my wife and I. I’ve been tempted to transition to something else, and may try Apple Passwords. Over the last week, while running iOS 18 Betas, I’ve slowly started to allow Apple to remember each password I use. After some time I’ll test a switch over. 

My password system is a bit odd, though. I like having some friction between logging into accounts. For instance, I have a problem with checking email too often. So I’ll logout daily, forcing myself to log back in. Going into 1P and manually pasting passwords in (I disable autofill) is fine, as it takes me a good 30 seconds to do so. Making things more automatic with Apple might defeat one of my personal goals of having a bit of a disconnect between myself and apps I’m trying to check less often.