Joshua Wold

I use a MacBook Pro and iPad every single day for work. Both devices have become critical to what I do as a designer and creative person. Several years ago I tried to make the iPad my primary device for everything design related. It didn’t work. It forced me to make too many tradeoffs and find workarounds for simple tasks. 

Things have settled though, and I now have a workflow that feels about as perfect as I could imagine. I work on a laptop for communication, high-fidelity design work, and just about everything else. 

But when it comes time to think, where I need to process the user experience of an app, think through a tough visual challenge, for connect chaotic pieces together, I always turn to the iPad. 

Over the years I’ve written about the various iPad apps for sketching: Miro, Paper, Linea Sketch, Adobe’s products, Procreate, etc. Each have their uses, and I’ve tried all of them and a dozen other options. With each app I’m looking for the closest thing to a piece of paper and pencil. Now, in the last year, Freeform has become my favorite app by far. Despite some [challenges] I’ve had with it, I can’t imagine using anything else now.

Thinking, for me, doesn’t happen in an app like Figma. Instead, I have to use my hand and a stylus to process through something. An iPad with Freeform is a perfect expression of that. After I’ve figured out the actual layout of something, I can then open an app like Figma and fuss with interface elements.

To go along with that I’ve also wrestled with iPad sizes. I currently own an iPad Pro 12.9″ and an iPad mini. While I bought the mini for travel, and setup the larger iPad on an Elevation Lab stand for my desk, I turned more and more to the mini. Now I’m 100% on the mini. There’s just something special about holding a tiny tablet in one hand and sketching with the other. It’s as close to a notepad as I could imagine, and it’s perfect. 

If you haven’t experimented with this, I highly recommend it. Any iPad will do, but training myself to think first by hand has helped me become a better designer. 

Over the years my digital workspace has transformed through the viewport of various screen sizes. I started my career with a 13″ CRT monitor as a teenager. At 15 I bought my own 15″ laptop. At 19 I purchased two 22″ Acer laptops and put them on a desk. I had it made.

Later I bought an LG Ultrafine 5k (27-inch) and when that died dropped back down to a 14″ MacBook Pro. That’s where I’m sitting now. Everything I design and craft is through that screen, alongside my iPad mini for low-fidelity sketching.

With Apple’s Vision Pro announcement I was interested in one thing: could I realistically use this in place of a single or dual-monitor screen situation.

The answer, based on the keynote today, is maybe.

Having large screen real estate in a virtual space could be a big deal. Being able to open apps, draw, sketch, design and have large reference screens beside me, all those things could be game changing.

The challenge is how it all works together.

Here’s an inventory of the apps I use right now:

• Figma
• Freeform
• Bear notes
• Safari
• Things 3
• iCloud Drive
• Zoom
• Notion
• Audacity
• Chrome (for podcast recording)
• Illustrator

These apps make up 95% of my usage on a Mac. So if I can use the Vision Pro as a secondary monitor situation for the Mac, and connect my keyboard and Apple Mouse, then it feels like a no brainer to buy.

I’m curious about focusing. Will things feel shaky when I’m trying to adjust pixels or sketch?

I have so many questions, but I’m excited. Will this replace larger monitors?

Going to spend far too many hours over the next year analyzing that question and figuring out if this is for me.

Why I use two iPads, and why I’d pick the mini if I could only have one.

Freeform was the most exciting to come out of WWDC. I saw its potential immediately, and couldn’t wait to get my hands on it.

I’m a software product designer, and sketch out all of my work on the iPad as a starting point before moving into Figma.

Here’s an example:

I work with several founders at a time, sketching their apps and helping to improve their products. It’s critical that I have an app that I can rely on to create hundreds of sketches.

My app of choice used to be Miro, and before that Linea Sketch, and before that Paper 53. I’ve tried every app that’s available for the iPad, and written about them in the past.

A few months ago I started trying out Freeform as a potential replacement for Miro. I just checked and I now have dozens of projects in Freeform. It wasn’t until a few weeks ago I realized I had transitioned 100% over to this new app. So, I canceled my Miro subscription.

I’ve been listening to other tech and Apple enthusiasts talk about Freeform, but haven’t heard anyone make the case that meets my needs.

Here’s a few more examples:

---

This app was made for folks just like me. I need a large canvas, need to hand draw my work, and it has to work on my iPad.

The app is good. It’s an amazing v1.0 of an Apple product, and it’s immediately beaten out every other app available – for my use case at least.

I’ve been keeping an eye on things I don’t like and do like, and have been meaning to write a piece on how cool this app is.

I’m taking the time to write this because of how much I already love the app. It’s passed the requirements for using it, and I can trust it in production with real client work. It’s fantastic and has become my most important design tool (along with Figma).

First, let’s start with the good.

The good

• Palm rejection works – This has been my biggest challenge with Miro over the years. If they changed one thing about their iPad app, I’d love to have a little toggle to only allow inputs with the Apple pencil. Palm rejection is horrendous and makes the app unusable at times. On Freeform it’s much better, worlds better in fact. Sometimes I run into issues of jittering with my Apple pencil, but after coming from an app that made me sometimes want to chuck my iPad across the room, it’s like a breath of fresh air.
• The canvas – Freeform has a large canvas, and allows for a lot of work. That’s a must.
• The tools – The tools for drawing are good. They work as expected, and I’m able to get my work done.

The bad

• Lag – Many of my UI pages start to get big. I’m sketching out entire app flows after all. Once I have the equivalent of 2-3 pages of an app, Freeform starts to lag a bit. The biggest area where this is a problem is in duplicating elements. If I draw a page of an app, and want to duplicate it, Freeform immediately freezes up and struggles with the request. Miro has some issues in this as well, but just limits my duplication to a certain amount of elements at once on the iPad. It might make sense for Freeform to do something similar.
• Naming files – This is a small issue, but it’s very annoying. Because of the duplication lag, I often duplicate entire files as a workaround, to save my previous work. However, when duplicating the files I want to rename them. But while naming I don’t know if the name I’m giving the file is a duplicate of another. So I enter the file name, and Freeform says it’s a duplicate – then asks me to start over. I wish the app didn’t do that, just throw the error, keep my text in the input field, and let me modify it myself.
• Duplication – Freeform struggles with moving large groups of elements. I can design an app, duplicate it and move it around, and many of the elements will shift on screen and get out of place. It’s unusable in some cases.
• Contextual menu popups – When I’m duplicating and moving elements I often run into issues with the contextual menu appearing when I don’t want to. I haven’t sat on this one long enough to figure out exactly what’s wrong, but it often shows up when I don’t want it.
• Weird zooming – Zooming in and out is choppy in the app. It’s nothing like the fluid pinch to Zoom I love from Miro and Figma. It’s almost like the app has to pause in between zoom sizes.
• Bonus: Zoom on the Mac – This is very weird. It’s so different from how most modern apps (like Figma and Miro) work, I have to click a button to zoom in or out. Feels like I’m back in 2005 with software.
• Selecting – A big part of UX design is sketching things, dragging them around, and playing with them (I really should write more about my process at some point). When I select a group of lines, and then want to move them around, I have to select the an area that is actually filled in. If I accidentally tap on the canvas of the selected area I have to start all over again. It’s incredibly frustrating, especially when I’m drawing with thin lines.
• Cross platform – I cannot trust Freeform cross platform. When I draw on an iPad, then pick up a second iPad or my Mac, and try to view the files, often 20-50% of the liens I’ve drawn are moved around. This has caused a bit of freaking out on my part as I’ve worried I lost data. Thankfully whenever I go back to the original device it looks ok, but I don’t have any confidence in cross device compatibility. This is a big deal for me as I like to switch between my iPad Pro 12.9 on the desktop and my iPad Mini on a reclining chair or on the go. I can’t do this though, I have to only use the iPad that corresponds to the Freeform file I created. It’s annoying.

Ok, so that’s the good and the bad. Now I’d like to get onto my wishlist for the next version of this app.

Wishlist

• Projects – Or some kind of organization. this is done well on Figma and Miro, and I’d like something similar on Freeform.
• Changing default brush colors – Unless I’m missing something, there’s no way to change these colors, so I have to modify them each time I open the app.
• Shortcuts to undo – I’m used to tapping two fingers to undo. Every other drawing app (except Notes of course) does this, I’d love quickly undo without breaking my flow and having to find the button.
• Setting defaults for brushes – I’d like to set the default sizes and colors for the tools.
• Constrain resizing – When I go to resize elements I’d like to force constraints. I’d actually even prefer that if it was the only option.
• Horizontal and vertical flip – Quite useful when I sketch something out and realize it’s facing the wrong way.
• Ruler – I don’t need a ruler exactly, but I’d like some kind of way to draw a straight line (Linea handles this pretty well)
• Grouping – Being able to group and ungroup objects would be really helpful in moving things around. I see an option to Separate, but haven’t been able to figure out what that does.
• Exporting – I wish there were more export features. Adding PNG along with PDF would be fine.
• Move to front and back – I don’t need layers per say, but like Miro I’d love if I could move objects to the front or back of the canvas.
• UI assets – I love how Linea Sketch has a few background assets, such as a template for an iPhone. It helps save a lot of time.

I’m hoping this tool continues to improve, I’m loving it already and feel like it’s made my job easier as a designer.

One final example:

I’ve been intrigued by watches my whole life. While I wouldn’t consider myself anywhere close to an actual enthusiast – I know just enough to realize I know almost nothing about the industry – I’m quite interested in watches in relation to their impact on technology as a wearable. I’ve often been curious how they could change my life.

As a kid I was gifted cheap watches for birthdays, and also bought a few at Walmart over the years. However, they always seemed to break within a week or two, requiring me to return to the kitchen stove to check on the time throughout the day.

At 16 I was gifted a nicer watch. I don’t remember the exact brand, but I think it was a Casio, and it wasn’t cheap. It had a few fancy features, and even had a small section to painfully add notes.

The story with all of them was always the same. I’d try one on for a while, play with all of the settings, and appreciate the awesomeness that a watch brought into my life. Watches were a bit of a superpower, enabling me to connect to something more than just my direct environment.

But I could never quite make a watch work longterm. First, I hadn’t found one that felt comfortable to wear. The bands pulled at the hairs on my wrist, they never fit well, and over time most of them wore out.

Finally at 19 I gave away my last watch, and for the most part never looked back. There were been a few times in my 20s and 30s that I tried again, but I was never happy.

I didn’t like the general design of most watches I found.

Analog watches are, to this day, hard for me to read.

Most bands suck. The fit is usually off.

Typing with a watch feels weird since it raises my left wrist off the keyboard; this is probably a bad ergonomic habit on my part, but still I’ll count it.

I often bumped my watch hand against stuff, since I wasn’t used to having it as part of my body.

With those frustrations came another element. I got an iPod Touch in 2010 and it instantly made a watch irrelevant in many ways.

Then the iPhone came along. While I was a late adopter – getting my first model in 2013 – it changed everything for me. A watch just didn’t make sense, and I didn’t like the ones I’d tried.

I bought a jawbone step counter, I tried 3-4 different Fitbit devices. But they never lasted.

Finally, in 2022, I bought my first Apple Watch. I picked the Series 8 in 45 mm, and chose the velcro sport band. I’ve been sitting on this watch for a few months now, trying it and seeing how it fits into my life. In short – and time will tell if I still feel this way in the future – it seems to address all the problems I’ve had with a watch.

The band

Even though it’s velcro, the band is fantastic. It doesn’t pull at the hairs on my wrist, I can adjust it to just the perfect size, and it has a low enough profile to not throw off my wrist while typing.

Time

I mentioned not liking analog watches. I found a digital time that works for me, and I can finally check the time without pulling my phone out.

Disconnecting

I had a worry that a watch would make me more connected to the internet; something I’m actively pushing against these days. Instead the opposite has been true, so far at least. I keep my watch and phone set to do not disturb most of the day, so my watch isn’t constantly buzzing or pinging. Instead I keep the small red dot indicator on, so that I can check if any new notifications have come through. That’s enough for me, and actually means I check my phone less now.

Complications

I’m just starting to learn about the world of watch complications, and so far I’m all in. I’ve chosen the Modular watch face, and picked the following complications:

• Activity – I like seeing how I’m doing on my steps for the day.
• Time and date
• Calendar – I like seeing what events I have coming up at a glance, again reducing my need for checking my phone so often
• Things 3 – Having my todo list close by at all times is a must, as I’m often adding things to it throughout the day, being able to do this from my wrist now is fantastic; even if the keyboard typing is slow.
• Timer – I work in 25 minute pomodoros, and having that on my wrist helps separate the timer from the computer or phone. I love it.
• Weather

That’s a lot, and it’s just perfect for me. Many of the use cases for checking my phone are now gone, and I can see so much of that data right on my wrist at a glance.

None of these are infinity wells (not my original term), where I get sucked into messages, catch up on email, or browse the web. Instead these are all complications that help me move throughout my day and ensure that nothing is lost. I love it.

A note on LTE

I bought the LTE model, hoping to use the watch on my daily runs. So far I haven’t been able to set it up, since I ran into some kind of an infinite connection loop with my phone carrier. Because of that I can’t speak to how well it works away from the phone.

So far I’ve found the watch a useful addition to my life. I like seeing how well I’m doing on my runs, I like checking text messages without opening up my phone, and the audio controls that pop up while listening to books or podcasts are useful.

The area that’s been a disappointment is in using the watch as a primary device. I knew I couldn’t do that going in, but I thought I could do more with the watch. My dream situation is to go into town, or on a run, with just the watch and AirPods, and nothing else. Instead I find I keep needing to bring my phone.

My attempts at loading music, books, or podcasts directly to the watch all failed. I tried Overcast, I tried Apple Books, I tried Audible, I tried Apple Music. In theory all of them should be able to load up audio to sync directly to my AirPods, but nothing just worked. Instead I fiddled with the apps a number of times, rechecked to see if they’d downloaded something, then finally quit and played audio directly from my phone. In this area the watch has been a disappointment, and I hope it’s something that can be solved in the future.

In terms of the size of the watch, I really like the 45mm. It’s big enough to read a lot of text, and it doesn’t feel large on my wrist. I was tempted to get the Apple Watch Ultra, but couldn’t justify the additional cost.

I’ll see how things feel a year from now, but so far I consider this a positive thing to add to my list of daily electronics.

Adobe announced an intent to acquire Figma for ~$20 billion today. I’ve had mixed feelings thinking about it throughout the day, while also trying to get work done with my projects.

On the one hand I’ve grown to value the tool and all that it allows me to do as a designer. My career started back with much older software. Macromedia Flash 4 was the first application I used to build websites, illustrations, and print graphics. Yup, you heard that right. To this day it still stands as my favorite tool for manipulating bezier curves. But, thanks to my high school ROP teacher, Ms. Jane, I moved on and converted to Illustrator, Photoshop, and InDesign respectively. I also picked up Dreamweaver, and eventually Fireworks.

Sketch came into the picture years later, but my brain couldn’t quite process how to fit it into my workflow. InVision came and went, along with Marvel POP, Balsamiq, and everything else I could get my hands on. So many fantastic tools, so many amazing teams. Adobe XD also floated through for a period of time.

Flash forward to 2022. Figma is one of the core application in my work for building out interfaces and designs.

It is, however, just a tool. The most important thing I’ve learned over the years, as tools have come and gone, is a way of thinking. I still haven’t figured out, in fact I feel like I know less now than years in the past.

Now, when I’m working with a team to build an application or workflow, I approach the project with an absence of tools in mind. That means holding off on Figma for as long as possible, even holding off on wireframes or mockups. Instead, I ask a ton of questions to try and understand what the software accomplishes already, where things need to go with the business, and what users need. This stuff is the heart of building great software, and it’s where I can see pushing myself and continuing to learn for decades to come.

Only after the work of understanding and shaping the software, after sketching out flows and drawings, after going back and forth and writing up How Might We statements, Jobs to Be Done, Acceptance Criteria, etc., after all the other things have been thought through, only then will I crack open Figma.

By the time I have a screen up in this fantastic app I already have an idea of the UX, a high level understanding of the components for UI, along with a million questions that still need to be answered.

Where Figma helps come in is in converging toward shipping something, and getting things out into the world. Even then it’s sometimes not necessary. Some fantastic engineers I’ve worked with will just take sketches and move them directly into code.

Now, I’ve spent some time talking about what I do without Figma. Does that mean the tool isn’t valuable? On the contrary, it’s enabled a way of thinking and working that was near impossible five years ago. I can collaborate live or async with product teams around the world. Like Google Docs, but for designers, it’s helped push the speed at which we can get things shipped. I love it, and I hope this tool is around for years to come.

My point, and the one I try to share whenever possible, is that good UX, good product design, comes with the thinking and asking, not so much with the tool.

Congrats to the Figma team! And, I’m excited to see what other tools appear in the space.

The last two weeks have been intense since I started looking for new work. I’m used to pushing myself and working hard to get things done. But there’s a certain level of pressure when I am looking for new work to cover the bills for my family, while also wanting to make sure my own personality and experience are a match for the companies I’m talking with.

I’ve applied to some awesome places, and started having interviews with teams of all sizes. I’m a bit tired, but I’m also invigorated. I’ve been able to talk to some fantastic teams, learn about interesting products that are getting built, and hear from passionate folks who want to make an impact in the world.

This is a scary time to be looking for a job as a designer. Layoffs have been announced around the industry, and given that we’ve just entered the technical definition of a recession, there’s now an extra layer of complexity to the whole thing.

I’m getting a little older. This year will my 35th cycle around the sun. When I started my career I was 19 years old, and the world looked bright and rosy. I had a few years of graphic design freelance under my belt by then, and jumped in with my brother to start a web design agency. We teamed up with a few other awesome folks, including my future brother-in-law, and built a little company to make websites and dream up our own SaaS product. This was 2007, bleeding into 2008.

Then a global recession hit.

Times were scary back then, and we worked hard for the next five years to find profitability, to help our clients and customers, and to push ourselves to learn. I’m thankful for those times, and incredibly grateful for the amazing folks that I got to work alongside. It was like two double majoring in design and business. I’d never trade that time and it helped shape who I am today.

So now, in 2022, facing a recession, looking for a job, and with the responsibility of caring for a family, I’m feeling excited and a little nervous. Excited because there’s so much opportunity, so much I can still learn, and some amazing teams that are looking for help. There’s also some things I’m building for myself, and while those my take a few years, they inspire me and allow me to tinker. I’m nervous though, because reality doesn’t always allow things to line up perfectly. Entropy gets in the way, things get messy.

And so I will take a day tomorrow to pause, spend time with my family, and recharge. One thing I learned this week, thanks to a forced 24-hour break with a high grade fever, is that there’s a limit to how much I can get done in a given period of time. I’m excited for the future, and despite my penchant for considering myself a realist, am optimistic about what’s next.

I don’t know the future, but I’m here for it.

TL;DR – I’m looking for a new product design opportunity. 😀

2022 has been a dream year for me in learning and growing in my career. For the past few years I’ve had the opportunity to work with a number of amazing teams on products within enterprise and the small business space. It’s given me the chance to learn and grow, and to continue to push my curiosity as a designer. 

Since December I’ve been supporting the team at Greg as a Senior Product Designer, focused on the mobile experience of the app. I’ve been able to learn about the ins and outs of mobile design in the consumer space, and loved picking up on all the small nuances that make up an amazing iPhone app. The juggling that’s necessary between product, design, engineering, and working runway was such an eye opening experience. 

Monday was my last day at Greg, and now I’m looking for a new opportunity. As sometimes happens, teams need to shift to adjust for the changes in the marketplace, in particular finding product market fit amongst headwinds in the consumer mobile space. 

I have full confidence that the Greg team will solve this, and will be watching from the sidelines, cheering them on. What Alex Ross and team are building is phenomenal, and I’m thankful for getting to work together this year. They’re trying to solve an amazing problem, helping people grow and build plants within a community. We need more apps like this, focused on improving the quality of life of everyone who joins. 

Right now I’m looking for new opportunities. If you’re hiring for a product design role, my background is primarily in enterprise software development, with a recent, and amazing, journey in mobile design. I’d love to chat, and am working on some ideas of my own in the background. Thank you!

For the past year I’ve been listening to some awesome podcasts and hearing updates from developers as they describe their transition, or in Marco Arment’s case, dipping their into SwiftUI.

I started my career as a web designer and frontend developer. Learning CSS and HTML was a challenge for me at the time, but I figured it out and stuck around long enough to understand the principles of responsive design, media queries, and all the little tinkering that comes with understanding how stuff fits onto the browser. From there I turned my attention to WordPress, customizing sites at a holistic level and helping businesses build enterprise level plugins for the WordPress space. Things got more abstract and I focused on the user experience overall, less on the code.

Focusing on design is important, but there’s tremendous value in understanding the structure of how a thing gets built. I allowed things to get too abstract without realizing the nuances of what my fellow engineers were building. For the last eight months I’ve worked alongside an awesome mobile app team, building out the experience in Greg. As things are starting to shift toward SwiftUI (or at least that’s the statement Apple made, we’ll see what happens in reality) it felt like the right time to give things a try.

So I bought a Udemy course and dove in. I’m shocked. There’s something about how SwiftUI operates that just clicks in my brain. I understand it. This doesn’t mean it will be easy, or even that I’ll really figure it out. But something about the mental model between Swift and SwiftUI appeals to me; perhaps this goes back to my HTML/CSS roots. We’ll see. For the first time in a long time I’m excited about code again, and bringing my designs to reality.

Choosing my device

I’ve been saving up for a new MacBook since February. Based on the rumors I suspected we’d see a new design for the MacBook Air in the Spring or Summer. So I saved, sold some stuff on Facebook Marketplace, and planned my purchase. Then Apple announced the Air, and it was everything I could have hoped for, minus the lack of an HDR display. I went back and forth on specs, and finally sprung for the 512GB model with 16GB of ram, midnight blue.

I listened to about a dozen hours of podcasts and scoured review sites trying to make sure I was making the right decision. 24GB of ram sounds amazing, but at that point I’m starting to get into MacBook Pro pricing territory.

I woke up at 4:45am on presale day and secured my order by 5:01am. Then I waited. I checked the status of my order a few times a day. No, that’s not true. I checked it many times a day. The wonderful package arrived this Monday morning. I was so excited.

Now, let’s back up for a moment. I bought a MacBook Pro last year, and have absolutely loved it. I went for the M1 Max 14” model and maxed out its specs, other than hard drive. It’s a dream machine and handles everything I throw at it. I don’t even know if I’ve been able to turn on the fans yet. It’s a beautiful device, small enough to take anywhere, and has an amazing screen.

Why I want two computers

The main challenge I had was not any limit to the MacBook Pro — other than its limited battery — but rather an issue with contexts.

For the past three years I’ve pushed to always do something on the side, regardless of what job I have. That’s important. As a product designer I spent a lot of my day expending creative energy to help build fun products. I love it, and I don’t want that to change. However, there comes a time where it’s important to make sure I’m investing some time into things on the side. It might be a hobby project, writing a novel, learning SwiftUI; it doesn’t matter. The point is I need to always do something for myself every day. Practically speaking that means taking 15-60 minutes and putzing away on something.

The challenge I’ve had is a lot of the things I’m interested in require a computer screen. If I try to do something creative, for myself, on the same work computer I’ve used for my day job — well, that’s doable. I’ve done it, I’ve spent most of my career with a single computer. But it’s not fun. It’s not delightful. There’s something about picking up a separate machine, with a just different enough screen, different colored keyboard, slightly modified browser and desktop space. Those things help trick my brain into a new context. It tells me that it’s time to do something fun for myself.

That was the idea behind getting a second computer. This week has been a rather tumultuous one, a fact I may write about later. For the first few days after the MacBook Air’s arrival I didn’t really feel any extra energy to try and enjoy the device. However, by the middle of the week I was pulling it open at the end of the day and spending some time putzing around on it.

This has brought me an unexpected amount of joy. Last night I dove into a SwiftUI course and lost track of time. Over two hours later I came up for air with a tiny app on my iPhone. This is therapeutic. Now, I don’t know if I’ll keep doing the two computer thing forever. Due to some changing circumstances I may have to sell one of them. But if I can I’ll hold onto both and use one to push my work and the other to push my hobbies.

I read about this a year or two ago from an author I admire. He stated that he has two different computers, one for writing and the other for the work of running his business. I love that.

For years I failed at becoming a regular journaler. My longest stint was a couple months with Day One, years ago. It was fun, and I liked reviewing the pretty graphs over time. But it didn’t stick, it didn’t have any real value for me.

Since December I’ve been journaling almost nonstop. Before that I was writing fiction, and loving it. Over the past eight months, because of a few factors and partially related to my creative energy, I’ve just been journaling.

The effect has been a good one. I can’t say yet that it’s had a profound effect on who I am, but it forces me to take a few minutes out my day and write. In that time I force myself to write a thousand words.

Because I type fast, that often doesn’t take long, especially since I do zero editing. I just type whatever comes to mind.

A funny thing happens when you write for a thousand words. In order to keep going I have to dig deep and start to think while typing. It’s a function that feels meditative. It’s like going on a walk without any devices and just having time to think. Only, it’s more active than that. I’m putting my fingers to the page and pushing out ideas. Most of it is complete rubbish, not worthy of reprint. But occasionally, and more often than I’d have thought, I am able to generate clarity in my typing. Ideas crystalize as I type and help me decide what I should do next.

Writing has changed how I think, it’s altered my brain in profound ways. The journaling has helped. A daily habit such as this has become a way of life for me, three years later. I love it, and I would have a hard time without this form of processing at the start or end of my day.

Now, as I’ve shared before, I want to do more than just journaling, I love to create and share ideas; and that will take more than just a few minutes of smashing out letters on a keyboard. It’s a start though, and

I’m thankful for that. I’ve kept up the habit and found that it’s much easier these days to push out my thoughts without self-editing along the way.

If you’re curious to try this I recommend a number of words that’s a little higher than you’re immediately comfortable with. A hundred words a day is too little for me, and would allow me to cheat, so to speak. The longer word count, lets me take a bit more time, and encourages digging deeper into my brain.

Sometimes I start with a retelling of what happened in my day, focusing on the emotions, the struggles, the big wins, and essentially going through a retro of the previous hours. Closing my eyes helps, and often I don’t bother with all the details, just enough to force my brain to concentrate for a moment. As Field Notes likes to say on each book, “I’m not writing it down to remember later, I’m writing it down to remember now.”

Yesterday I got a bug in me and sat down to write. I began the day like most other, with a journaling session. That normally takes me about 7-8 minutes to write a 1,000 words.

Most of these sessions are just a brain dump of the day’s activities, where I like to process how things went. It’s useful and I enjoy doing it.

Later I had another time slot where I could do so some more writing. In that time, I busted out another 2,000 words, half of which was fiction. It felt so good to be back, to work toward creative writing again. I resumed a novella from last year and added an intro chapter to it. 

Today I was excited to continue and thought about what I’d written, looking forward to seeing if I could start a streak again. 

I sat down to write this evening and pulled up Ulysses. Now, in the past I’ve had some issues with syncing between Mac and iPad; namely that it is effectively a no go. Something happens between the two where it seems to just keep re-syncing forever. That’s a waste of time, so I leaned into just writing on the Mac. 

When I pulled up Ulysses again to write, I had a moment of shock. The 1,000 words from the previous day disappeared. After nearly a half hour of searching, and going through all my options, the words are just gone. That has shaken my confidence in the app. I’m now considering other options, IA Writer and Scrivener are top of the list. To have finally to back into creative writing, and run into a snafu on the first day, is a bit of a bummer.

I didn’t let that stop me, though. I channeled that frustration into a short story of a writer being frustrated that his fiction writing got lost. Yes, meta, I know. 

We’ll see how tomorrow goes, if I’m able to keep the streak going. Hopefully, I can recover those thousand words, but if not, I’ll try to just learn from it. 

Update: I put the note in the trash in Ulysses. All is well!

Over the past few years I’ve enjoyed jumping around between enjoyable works of fiction. I like finding a great book, then spending time reading other books from the same author. For a few years it was Stephen King. So far I’ve read about ten of his books. He’s such a talented author, and I hope someday to be able to understand his ability to make characters interact with the proper tension and meaning. Other amazing authors have included J.K. Rowling, Suzanne Collins, Jeff VanderMeer, Max Brooks, Andy Weir, and a half dozen more.

I love falling into the world of these authors.

So it was with some interest that I picked up Brandon Sanderson a few months ago. I’d heard him mentioned for the past couple of years, highly recommended as one of the best fantasy authors writing today. At one point my barber sang his praises. On the recommendation of two friends I started out with his Mistborn series, all on Audible.

I was hooked immediately.

Within a short period of time I poured through the first three of those books. The world he created drew me in and filled my imagination. I often paused the books to contemplate the secrets I’d just learned, or to appreciate the literary genius of making a certain scene come together.

From Mistborne I started on The Stormlight Archive. This one took a bit longer to get into, but I enjoyed it even more than the Mistborne series.

Something I love about Sanderson, a bit in contrast to King, is his ability to handle mature topics without delving deeply into salacious details. The way characters interact with each other feels like more like Lord of the Rings fantasy, and less like Game of Thrones.

I’m excited by this, and wondering about the implications for my own writing, to tackle important themes while keeping the books available for a wider audience.

It’s so fun to find great books and to be inspired by other authors.

I really enjoy watching Apple events. It’s been a joy of mine to tune in and catch up on what’s new. I don’t have all the Apple hardware, but I have integrated quite a few different devices into my daily life over the years. A change in software across their various platforms can have a decent sized impact on my day to day productivity. I haven’t had a chance to watch the entire keynote yet, but I’ve skimmed through a few sections and caught up on a number of highlights.

Following are a few of my hot takes. The angle I’m taking for each of these is a mix of my personal time using Apple devices, as well as my time as a product designer working with a team on a mobile app.

Freeform

This is one of the most exciting announcements for me. While it won’t be out for months, and I haven’t had a chance to actually play with it, the general idea is fantastic. Live sketching and white boarding with others. Amazing.

I’ve used just about every iteration of iPad apps for sketching and collaboration. Each have their pros and cons, and I’ve written about them on a few occasions.

Having great collaboration for realtime users to sync across a network is key to my work. Figma has changed how I work as a designer, being able to work directly with other team members in a live environment. Its limited though, to hi-fidelity designs; when we’re further along in the design process. I’ve struggled to find an exact match for the more lo-fidelity aspect of my job, when I want to think through rough ideas.

The real-life counterpart is a whiteboard with markers (not chalk, I cannot stand the feel of chalk). A physical whiteboard is perfect in a room with others, but over the internet it just doesn’t work.

So I’m quite keen to test this out and see how it works with several of my team members. Currently we use a mix of Miro, Linea Sketch, and a few other things, but all are imperfect for live collaboration.

Continuity Camera

Amazing. I want to use this. Webcams on Apple desktop devices aren’t great. They’re passable, but not anything like the quality of camera on a recent iPhone. I’ve been thinking about some of the third party software to hook my iPhone, or even buying a digital camera or webcam, but all of that feels too complicated (and potentially expensive). Being able to use my iPhone in meetings for a great camera experience sounds perfect.

Stage Manager

This looks pretty sweet. I will have to try this first to see how it feels. Having this new window application tool across Mac and iPad OS could help to bridge the gap between the two operating systems.

Dictation

I haven’t looked into this enough yet, but having dictation on device with improvements could help pull me back into my workflows. I’ve tried to dictate for writing, but working live doesn’t work because of the timer limitations set by Google and Apple. At the moment I record via voice memos, then pull into Otter.ai. I’ve even been thinking about re-using my physical Sony recorder. If on-device dictation has improved, and is without limits, it could be perfect for my writing use cases.

Making it personal

There’s so much more I want to talk about, but I’ll keep this short for the moment. I am struggling with a decision on how I’ll move forward. The new MacBook Air M2 is perfect; it’s exactly what I’ve been hoping for, and it’s within the budget I’ve saved for this year.

I’ve been planning to buy a second laptop for a while now, in hopes of separating my creative writing from my work life. After spending all day as a designer, I often want to close my laptop and not use it again until morning. However, I also really enjoy creative writing. If I had a second device, preferably one that looked and felt different, and only used that device for personal things; well that might help with my motivation for pushing my writing forward.

I thought the iPad could be that second device for me. But it just doesn’t handle multi windows the way I want, and the writing software I use isn’t as good as the Mac equivalents. Now, with the iPad getting some much needed window management, as well as true external monitor support; it’s looking more tempting.

However, the M2 is exactly what I wanted. I’m likely going to keep forward on my plan for the new laptop, but it’s exciting that the iPad has become interesting again.

Recently I’ve hit a weird spell where I’ve struggled to write fiction. There are a few factors for this, and I’m working through them in my mind. I might share more on that later.

During this time I’ve continued to journal daily, and continued to pour myself into books. Since my early twenties, I’ve noticed a pattern with my reading habits. If I stick too long in fiction, non-fiction, history, self-help, etc, I burn out. So, as a force of habit, and also following my own instincts, I shake things up a few times a year.

For several months, I poured myself into the Mistborne and Way of Kings series from Brandon Sanderson. These have been an amazing read, and kept the flame alive for my desire to build stories and fictional worlds. 

The important thing for me, though, when it comes to reading, is to not make it feel like a homework assignment. If a book starts to drag, I’ll pause it. If the topic meanders in the wrong direction, I’ll just stop. I don’t want this thing that I do to become a drudgery. It has value and helps me grow to become a better person. But that shouldn’t happen at the expense of the pure joy of reading. 

I’m trying to ensure that not every aspect of my life feels like it’s leading to something. Some things we do should be for the thing itself, and not for the hope that it will help us capitalize on it at a later time. 

So, after a multi-month fiction stint, I pivoted to a handful of books (and podcasts) on other topics. I’ll probably come back around to the fiction in a few weeks, especially since I’m excited to see where the next Brandon Sanderson book takes me. 

Note: Almost all of my reading is through audio. I still the wrong verb intentionally, as it rolls of the tongue better.

I’ve taken to private journaling in the last six months. It’s a rewarding experience. This is the most consistency I’ve applied to capturing my thoughts and documenting them on paper. I love it. I’ve learned some things about myself, and used this practice to process. When I reach the end of the day, I spend a few minutes typing out my notes, and that often helps give voice to my emotions. This is a worthwhile effort, and at some level I want to keep it up going forward. 

However, I’ve also used this as a crutch to avoid pushing my work out into the world. On a recent podcast interview with Joanna Penn, Derek Sivers shared his desire to create in public. He jokingly mentioned the reason: ego. While it sounds shallow on the surface, it’s worth some additional thought. Austin Kleon and Seth Godin share about shipping things to the world and not holding them to ourselves. 

Because I’ve gone private and pushed my notes internal, I’m holding all these thoughts inside and not providing an outlet to share them, to learn from the feedback I receive, and hopefully to help someone else dealing with the same issues. 

I don’t know what this means for me long term, but it’s enough to give me pause. I want to write to capture thoughts, to process my own way of thinking, and to use words to understand who I am. That can happen in private, and should. However, there’s an inherent value in packaging things up in a format meant for consumption. It forces me to coalesce all these divergent threads and put them together in a way that makes some kind of sense. 

A recent book has gotten my brain back into the train of processing the importance of the things I try to tackle. So much of my default is to think about the past or future, and not focus on what I have in front of me. I love books that help bring that point back around and help me appreciate what I have. 

Nearly three years ago, I committed to a daily habit of writing a thousand words a day, six days per week. I’ve kept to that since, even when writing in private. The practice has become a part of me. I don’t question whether I can write, because I do. There’s probably less value in hammering away at the words within seven minutes, versus taking some time to process and think through a coherent flow. Still, I’ve found so much value in writing and in the identity that comes with knowing I can transfer thoughts onto the page. It’s helped to break through some fears I’ve held and sharpened my ability to confront problems with words. 

I’ll keep at it, and see what breaks through; public and private.

The iPad is a lot of things, but for me the number one purpose is using the Apple Pencil. Over the years I’ve tried the larger iPads, mainly the 12.9” Pro, and put them to the test as full computing devices. But, and again I’ll state that its specific to my needs, it fails at being my primary device.

And so I enter the awkward state of needing both a laptop and wanting an iPad; a large one at that. This beautiful piece of aluminum and glass is useful for a lot of things, in theory. But in practice it functions best as a pen inputing type of device.

Software for the iPad is not great; at least in comparison to the things I like to do on a Mac. Whether I’m using JIRA, Github, the entire Google suite, Slack, or web browsing, all of those experiences are subpar compared to working on a Mac. Sometimes I’ve tried to ignore that fact and go iPad first. The turning point for me was thirty minutes of wasted time trying to get a specific type of document to my banker via their custom portal. True, that’s a unique circumstance, but it highlighted my constant challenges with not having the right tool for the most common jobs I run into.

Writing on the iPad has been another job I’ve attempted. As a writer I like the idea of a separate machine; something different from my work device, so that I can have a mental shift in context. For several months I used the iPad, but got stymied time and again. At first it was the lack of ergonomic options. I like to write with elbows at a ninety degree angle, and wrists straight on. In addition I prefer the screen at eye level, and without bending my neck down or up too much. To date these things are near impossible to accomplish on an iPad. The Magic Keyboard isn’t enough, although it has some great benefits, and the whole iPad stand ecosystem is severely lacking when it comes to any contraptions that can get the screen close to eye level. It’s ridiculous, and I’ve often pondered how I could make a stand myself. There’s plenty of great laptop stands, such as the Roost, but nothing like that for the iPad. I digress.

Next up, and the nail in the coffin for me with writing, is the bad software. I like to use Ulysses for writing that extends beyond a few thousand words, it helps organize my thoughts and keep things running forward. Ulysses on the iPad is okay, and looks great from a design perspective; however the syncing is severely flawed. Each time I load the device, even if Ulysses on the iPad was the last time I wrote in the app, it feels the need to re-sync my entire database of content. In practice that requires sitting around for a few minutes waiting for everything to load, then checking for conflicts. That doesn’t work when I only have about 15-30 minutes per day for writing.

None of these problems exist on the Mac, all of them have been solved long ago.

The iPad is amazing, but for writing or working my day job, it fails.

Now we come to the reason I like the iPad, and why I keep the largest size around at my desk, and in my laptop. When it comes to drawing the iPad is king. And a bigger screen is better. A friend has got my interested in trying the iPad mini again, but for now I’ll stick to the largest size.

I love the Apple Pencil as an input device, and bad palm rejection not withstanding, the act of putting lines to a digital page is a delightful experience.

And so we come to the point of this post; Linea Sketch’s latest update.

Linea is an amazing app for the iPad. It’s almost perfect. Over the years I’ve shuffled between a number of drawing apps, depending on whether I’m illustrating, sketching, drawing, white boarding, or painting something digitally. Each has their strengths, and many have weaknesses. Despite some of the setbacks with Linea, which I’ve highlighted elsewhere, I keep coming back to it for work. When I need to ideate through a software idea, or new feature, I’ll jump to analog paper and pen, or pull up Linea.

Apple Notes, Procreate, Moleskine Flow, Miro, and a dozen others (I need to check out a recent recommendation from a friend for Vectornator, so the jury is still out there), all have their place; but Linea keeps hovering between my favorite and second favorite.

A recent update solved one of my biggest requests. Before I get to that though, let’s go through my wishlist.

Better syncing – iCloud on Linea Sketch is a nightmare. Similar to Ulysses I often have to wait several minutes to get my previous drawings loaded up and synced to the device, even when that iPad was the only place I opened up before. It’s ridiculous. Last month I disabled iCloud entirely on Linea, a huge risk in itself, and the app became usable again. It’s fine – so long as I remember to manually copy my designs to the Mac.

Larger artboards – The artboards in Linea are too small. At the moment its limited to the size of my screen, which forces me to open up new artboards or shrink things down to fit. I’m not asking for unlimited canvas sizes, but wish there was a method to go bigger, even 4x the current size would be a huge help.

Better palm rejection – Lately I’ve been getting a lot of errant scribbles from my palm, it’s not a deal breaker, but it’s annoying to have to erase them. This is a hard bug to track though, so I don’t know how it would be fixed.

Better resolution zoomed in – Because of the small artboard I often zoom into the designs, which shows off the horrible pixelation of my pen strokes. This could be solved by larger artboards, or just doubling the resolution of the current screen.

With those concerns out of the way, I’m really excited about a new feature announced in the 4.0.1 update: Watercolor brushes!

This is a specific request I had in the past, and it may win me back over from Moleskine flow. Though a lot of my design work is simple and sketch like, watercolor brushes help to quickly make things come alive. I haven’t tested this fully yet, so look forward to a new post soon with my thoughts.

Note: I’m not sponsored to say any of this. I have no affiliation with Linea other than thinking they’re awesome.

It’s okay if you don’t know everything. For many years I’ve understood this in my head, but it’s only recently that I’ve started to internalize it at a deeper level. Not knowing doesn’t mean that you’re intentionally ignorant, nor does it offer an excuse to play dumb all the time. Instead it means that you’re willing to speak up and say the parts you understand, but pause right at the cliff; right at the point where you want to speculate and look smart to the room. Instead, take a breath, call out the uncharted territory that you’re about to enter, then step forward.

This happened recently in a critical meeting with several team members. I presented on a topic, one which I’d prepared for and understood well. However, during the meeting questions came up outside the happy path I’d planned. At first I was tempted to push forward and speculate, to cover up and pretend. However, I had a reminder floating around in the back of my head, telling me everything was going to be fine. I took a deep breath, called out to the team that I wasn’t sure about the questions, since they were an area I hadn’t thought about or explored. However, as a fast followup, I then shared some ideas that came to mind in the moment.

That both allowed me the room to be candid, to be vulnerable, and also opened up the space to move into unknowns, to speculate. That balance is critical, and building trust with your team can lead to transparency and openness.

At times I’ve been criticized for not knowing, for admitting I didn’t understand something. However, those times are very rare and I could likely recall them on a single hand. It’s possible that I was self-ingratiating, and my attitude in the situation showed through. Or it’s possible that the person I admitted vulnerability with didn’t know how to handle that, and based on their own insecurities used it as a weapon against me. Those examples though aren’t worth the walls that I’d be tempted to throw up just to protect myself from a few uncomfortable situations.

My recent call helped to further cement in my brain the value of not knowing; when combined with doing your absolute best, bringing everything you have to the table, you may be able to open doors to new opportunities.

I don’t like having a book or movie spoiled. If there’s an outside chance that I’m going to watch or read something I don’t want to know ahead of time any major plots or twists. In fact, telling me that a great show has an unexpected twist – even without revealing details – is itself a spoiler. It’s quite endearing when someone is trying to share details about something and realizing they can’t share the reason why.
Because of my sensitivity on this front, I’ve started to convey why I liked a thing without explaining what happened. It’s a bit tricky, but it gives me the chance to share about interesting stories without giving away the plot.
This is a great challenge in a way. If I want my friend to watch a show that I loved, but I don’t want to spoil it for them, I need to figure out a method for explaining why it’s worth their time based on what I know about them.
The biggest tip I can suggest, if you want to do this yourself, is to focus on how you felt about a story, rather than explaining what happened.
For me this often comes down to whether I thought the ending of the movie was satisfying, or if the mood of the book matched my interest level.
Sometimes I get lucky, and I forget the spoiler by the time I read the book. That happened with the red wedding; I knew something was going to come up in the books, but didn’t know who it would happen to. The shock was still just as strong as if I knew nothing.

Several years ago I stumbled across Magic Grips, a fascinating silicon accessory to the Apple Magic Mouse. For those who prefer more ergonomic mice, or are used to a trackpad on a computer, the Magic Mouse probably looks like a weird contraption that is more form than function. After many years of use I can attest to the absolute value of touch functionality on a mouse. I love it. I can’t go back to manual click buttons, and I just don’t like the trackpad for my precision design work. However, I like to find ways to protect my hands over the long haul, so I’ve sought a compromise.
The Magic Grips are amazing. They help to make my mouse feel more hefty in my hands, more sturdy in a way. Each time I’ve installed the grips – we’ll get to that in a minute – I’ve preferred the larger size and found that usage of the mouse just feels better. My hands can hold onto the silicon bits and movement is more comfortable in my hand. That, combined with an awesome mousepad from UgMonk, makes moving across the screen a near delight. Pro tip on that point: I like to increase the speed of my mouse to whatever max the system allows.
The problem though, is the adhesive. About two days a week I travel into a Coworking space. That helps me switch things up a bit, and not always work out of my home office. I put the mouse into my backpack each time, inside a specific compartment. I’m pretty sure that the stress of movement is a problem for the grips. After about a year of doing this the adhesive starts to come off. I’ve tried to figure out a good way to fix this, and asked the company if I could just buy replacement adhesive strips. So far I haven’t had any luck on that front. However, to their credit Elevation Labs has been awesome on customer service (their absolute lack of any help with my adhesive problems on the DraftTable V1 notwithstanding – but that’s another article), sending me full product replacements several times. That gets tiring though, and makes this product less than perfect for my use.
Going forward I’m going to need to live without the grips, buy a second mouse just for travel (sans grips), or find an adhesive that I can more readily re-apply whenever the grips start to fall off. The last option, and I have spent a small amount of time looking, is to find a case designed for the Magic Mouse + Grips. No luck on that front yet.