Getting a grip on my digital life

I’m too closely intwined with my digital life. I have a problem. At times it holds my attention more than my real life, and some days it’s hard to tell the two apart.

Technology has been wonderful for me. As a teenager, with unknown prospects for where I could take my life and career, technology opened doors for me. It’s been a force for good in my life, and because of that I’ve started to believe any new iteration of technology must be good.

As a young teenager I worked an entire Summer in the scorching heat of Arizona to save up enough money for my first laptop, costing roughly $1,500. Around that time I started to realize that computers weren’t just for gaming or instant messaging, I could also be creative. At that time a battle between my ability to create versus consume began. This was in 2001.

It all started with graphic design. I realized I could take my love of drawing into a digital medium and create things online. And, people would pay me for it.

Years later I added fancier devices: an iPhone and iPad, and had a full arsenal of software and hardware available to pursue creativity. But along the way the battle for creativity versus consumption picked up.

The first problem I faced was gaming. From ages 9-13 I was deeply absorbed in any game I could get my hand on. Entire months disappeared into fantasy worlds. Cracks in this cycle began when I realized I could be creative and earn some money with it.

For a few years things went in a more positive direction, I mostly ignored the consumption side of computer use, and technology became a tool primarily for career growth.

Then, slowly consumption crept back in. Digg, Reddit, Facebook, Instagram, LinkedIn, Gmail, Slack, all of my favorite tech and news sites, and more. Then, when I got my hands on an iPod Touch (and later an iPhone in 2012), the floodgates really opened up. Any information or entertainment I wanted was available to me, right at my the touch of a finger.

I successfully fought against most of it some of the time, especially since had personal and career interests that were more important. However, in all the spare moments between things, or when I felt that I was fighting too hard against learning something, the temptation to take a break and pull at the infinity pool in my phone became too strong.

Other than a few rare respites, my quiet times disappeared. At 31 years old, I’m right at the edge of a generation that remembers life before and after connected technology. I remember times of boredom and play away for screens.

I’ve tried a dozen ways to curb my internet and consumption use. I’ve tried life hacks, minimalism, and sheer force of will. Some days I win, and other days it’s too much to ignore the siren calls beckoning me.

With all of that context I tried something last month. I picked up a new book from Cal Newport called Digital Minimalism. I’m a huge fan of his work. His blog and previous books have inspired me in career decisions, as well as how I’ve used social media.

In 2016, inspired by Deep Work, I quit social media for 30 days. When I came back I realized how little I actually needed any of it. I have since eliminated my usage of social media by about 80%. My trick there has been to unsubscribe and unfollow everyone on all my accounts. It’s made social media mostly boring. However, I still go on to try and find a dopamine hit throughout the day. A decade of habits is hard to break, but I’ve gotten close.

When I saw a new book by Cal Newport, I knew I needed to read it, but hesitated for a few months. I was worried it would hit me over the head with guilt about the way I was too absorbed by consumptive technology. But I was wrong. It was a genuine and heartfelt guide to inspire all of us to live a better way. It offered encouragement and directions for how I could fight back against the tide.

In the middle of reading the book I decided it was time to spent 30 days disconnecting from the sources of mindless input I’ve grown accustomed to using. When I did this in 2016 I eliminated social media, now I wanted to include almost everything else.

At the same time. I was reading Make Time, a book by Jake Knapp and John Zeratsky. It describes a specific category of activities as infinity pools.

Infinity Pools are apps and other sources of endlessly replenishing content. If you can pull to refresh, it’s an Infinity Pool. If it streams, it’s an Infinity Pool. This always-available, always-new entertainment is your reward for the exhaustion of constant busyness.

This concept resonated with me. I have a lot of infinity pools. Even if the content they offer isn’t great, it’s still comforting to gaze in and try to get a dopamine hit. So, anything with a pull to refresh lever can count.

So, I knew I needed to try something. I also didn’t want to eliminate actual hardware devices, not yet at least. I wanted to see if there was another way.

For the past 11 years or so, I’ve willingly accepted most forms of technology into my life. Whether it’s entertainment, productivity, or learning, I’ve had a habit of trying it all. Now, because of my own attempts at simplifying my life, I’ve been able to successfully moderate a number of these sources of content.

However, I’m a single imperfect person fighting against consumption designed by some of the brightest minds in the world. Trying to hack my way through using these streams of data is a losing battle.

I may try to curb my social media use, cut down on news intake, and limit my time playing games and streaming TV. But it’s not enough. I can resist a few hours or days at a time, but I eventually go back.

So, when I heard about a plan from Cal Newport, I was inspired to try it.

The basic plan is to eliminate all consumption for 30 days. If it’s not critical to maintain relationships or your career, cut it out. There can be exceptions for specific cases, but on the whole this means no social media, no digital gaming, no tv or movies, and no content sites.

So, I wrote my list of things I’d eliminate for 30 days.

I then created a wallpaper and set it as a background on my phone and laptop. To further enforce the habit I blocked all of the domains on my devices.

Here’s the list:

So, how did it go?

For the first two days I felt jittery. I kept pulling out my iPhone to check Instagram, look at Reddit, or read one of my favorite blogs. I even typed the urls to my favorite sites multiple times without realizing what I was doing. It was only when I’d see a blocked site notice that I’d remember my detox plan.

After the first few days I settled into a few new routines. Because most of the sites I would normally visit were off limits, I used a lot of downtime for reading books, listening to podcasts, etc.

At night time, I went to bed roughly an hour earlier than I normally would, since reading a book isn’t nearly as stimulating as watching a movie or browsing Instagram.

In summary it was absolutely a good thing.

I’m now given it some thought for how I can make lasting changes.

As I’m writing this, I logged back into most of the sites I’d blocked, since we’re right on the 30 day mark.

On all of my social media accounts I only found two messages that were folks reaching out. I dropped a quick response back to both, but neither was urgent. On my favorite tech blogs I read through the last month of articles, and realized I hadn’t missed anything important.

Overall this detox was tremendously valuable for me. I still wasted some time on refreshing email and visiting sites that were useless (for example, box office results for Avengers: Endgame), but on the whole this detox gave me control of my time again.

The biggest takeaway is that I don’t need most of the sites I blocked, and I need to find better ways to use my time on the whole. We’ll see how that goes.

My illustration process

Recently I did an illustration for Jonathan Wold for an article he wrote on his site. In this post I wanted to share a bit of the process, and hopefully inspire others with how messy it can be to get from the beginning to the end.

We’ve worked together quite a bit in the past (we’re brothers after all), and we both know how to trust each other to get from an initial idea to the end result. Often Jonathan comes up with the idea for an illustration he wants, and then we have an initial chat about it. From there I try a few things out, and then I’ll text them over for feedback.

At that point he gives thoughts on what he likes and doesn’t, and I’ll keep tweaking. The key factor though, is at any point I’m welcome to disagree with his assessment and push in a different direction. In fact I do that often, maybe half of the time. He trusts that the end results will work out, and prefers instead to give general guidance, but not to push too hard in any direction. Because of that I try not to get too attached to any one idea until I take it from sketches to full on illustration.

First, here’s the final image:

And here’s the most of the steps to accomplish that:

And here are some of the reference images I was using throughout the process. To show that all design is inspired by others.

And finally, thanks to Procreate I can share a video of the final step. Hope you enjoy!

My current setup, 2019 edition

For traveling

If I’m working at a coffee shop for the day (I like to do that 1-2 days/week, even though I work from home), or if I’m on a trip, I’ll likely bring some combination of the following.

  • Backpack – My current favorite is the Bullet Ruck 15L. It fits a 15″ laptop quite comfortably, and since I carry my laptop in a sleeve I’m not as worried about it getting scratched up or bumped around.
  • Laptop – 15″ 2018 MacBook Pro with a leather sleeve. I debated between the 13″ and 15″, but ultimately decided a more powerful computer and a larger screen would be a good thing, especially for more eyes. I’ve started getting tired of staring at small screens. So far (and it’s still quite new) I haven’t had any problems with the keyboard.
  • Stand – For the past few years I’ve been using the Roost Laptop Stand. And, while it looks a bit funny, I’ve found it incredibly useful and compact. It helps me use my laptop with a mouse, and elevates it to where I’m not staring down at the table while I’m typing.
  • Mouse – I use the Apple Magic Mouse 2 with side bumpers from elevation lab. It helps make the mouse feel a bit more wide in the hand, and might make it more ergonomic.
  • Keyboard – Currently using the Magic Keyboard, I like that it has an on/off toggle finally! I can disable it in my backpack so it doesn’t try typing away on my laptop.
  • Mousepad – I have a leather one I picked up a while back, and love it. I’ve started using this less and less, but sometimes I find the tables at coffee shops can feel sticky, and in those cases having a mousepad is a good thing.
  • Power – Right now I have a bit of a problem. My iPad and laptop use USB-C for power, my phone uses Lightning, and my headphones use Micro USB. The way I solve this is by bringing 2-3 cords at a time, as well as power bricks. I also carry a small phone charger with a lightning cable built in. I also carry this power strip along wherever I go. It functions as an extension cord and lets me plug everything into one outlet if necessary. My only negative is that the outlet area is a bit bigger than I’d like.
  • iPad – Wherever I go I typically bring my iPad Pro (2018 12.9″) with an Apple Pencil. I’ve been doing a lot more illustrations lately and love having it around.
  • Timer – This is a new edition to my set. I’ve started using a physical timer to help me focus for 24-45 minute periods of time without distractions. The only negative with the one I picked up is the screen scratches VERY easily.
  • Pencil and paper – My current favorite setup is a mechanical pencil with a Steno Field Notes. I really like having my notes lay flat, and steno pads do that the best.
  • Headphones – For Christmas my wife bought me some refurbished noise canceling headphones. They work perfectly. I love them. I lost my AirPods around the same time, so I’m waiting to pickup some new ones. As a backup I carry some Apple Earpods as well.
  • Jacket – Wherever I go I also bring my Patagonia Puffer Jacket. Never know if it will get cold, even in a coffee shop.

When I’m in town I like to visit my favorite coffee shop / coworking space a few days a week. Since I work for a distributed company, they offer a coworking allowance which covers what I might spend on coffee (decaf vanilla late with caramel and oat milk please), as well as the cost of using the adjoining coworking area.

It’s kind of a funny thing, but at home I’ve gotten in the habit of sitting in a likely unergonomic fashion. I don’t have my legs on the ground, instead I sit on one and adjust my legs throughout the day. When I’m at a coffee shop I keep my shoes on, and tend to sit in a way that’s better for my posture.

The only negative is most places outside of my house are loud, so taking calls can be a bit more challenging.

Working from home

At home there’s a few additional things that makeup my office. I have a standing/sitting desk (which I keep in the sitting position 95% of the time), and an IKEA Markus, chair, previously recommended on the Wirecutter. Planning to upgrade both of these this year, so I’ll post my findings when I do.

For a monitor I’m currently using the LG UltraFine 5K display. I like to have it facing directly in front of me, with the laptop off to the side on the Roost stand.

GORUCK Bullet 15L mini review

Or, another title could be, my quest for my perfect backpack. For quite a few years I’ve tried backpacks of all types. It’s a funny hobby for me to research different backpacks and see what makes the most sense for me.

I wrote previously about a trip I took with the Bullet 10L (shown at top right), and how well that worked. The downside of that, is on that trip (and several others) I often ended up with the backpack and a tote bag to carry the extra stuff I needed.

When I’ve taken the GR1 (shown at top left), it fits more stuff, but generally just feels more hefty and oversized for day trips and such.

When GORUCK announced a 15L last Fall, I was quite excited! It wasn’t till March that they finally came out in the black color, and that’s when I knew I’d need to give it a shot.

I recently upgraded to a 15″ MacBook Pro, and it doesn’t fit in the 10L anymore. I was quite pleased to find that it DOES fit in the 15L, and even slides into the inner pouch. That’s a big win.

So, where do I fall now on backpack choices?

Well, the 10L technically does fit what I need for short trips, but it’s a tight squeeze. I recently read that having an extra 20-25% spare space in your bag at the start of a trip is a safe bet. You’ll probably pick something up on your way, and you don’t want things to be too cramped.

So, if you want to be a one bag person, and you find something like the 21L GR1 too big (or heavy), then I’d recommend giving the 15L a try. It’s the same height as the 10L bullet, and the GR1, but its width is right in the middle.

In addition, it has a better handle on top than the older 10L (I think they’ve now fixed that in new versions).

I still love the 10L, but will be excited to see how the slightly bigger version does on my next trip.

What does “Not” crazy at work look like?

I’m just a few weeks into a new job, and I have a few observations I want to share. I’ve been inspired by a new book, It Doesn’t Have to be Crazy at Work. This book, combined with Deep Work, has encouraged me to explore ways to focus and get things done, without tons of unnecessary distractions. At Automattic I’ve noticed a few things that are positive indicators for my ability to focus on the things that really matter.

  • Async over live – I’m seeing a tendency expecting that responses and decisions will get made asynchronously. That gives everyone, regardless of timezone, time to spend a few hours (and maybe days) looking things over and responding when they have time to focus.
  • Longer time horizons for work – When you can measure your project goals over quarters and years, as opposed to days and weeks, you open up the opportunity for your team to think about the greater needs of your customers. You need balance of course, you usually can’t take 4 years to focus on shipping a product. When teams and individuals make decisions based on longer time ranges, they can often be more calm and thoughtful.

Those two factors help encourage time to think and focus. I love that, and I’m looking forward to seeing what the next few months bring as I get to dig into some projects here.

Moving to Automattic

Tomorrow I’ll be starting a new job at Automattic as a Product Designer. I’m both excited and reflective as I think about what’s ahead in 2019 and beyond.

For the past 3 1/2 years I’ve worked full-time at XWP. I started as a Team Lead, then brought the role of Product Owner (while learning it along the way) to the company in 2016. For the past two years I’ve led the company in bringing user experience design and product design to the projects we took on.

I’ve been able to work with some amazing teams in the enterprise WordPress space as a part of XWP. This has included working with Google on the AMP plugin for WordPress, as well as AMP Stories, working with Beachbody on Demand to help build a new CMS experience for their editorial team, and some amazing engagements with clients such as PMC, News Corp Australia, and more. I’m thankful for the whole team at XWP and the great times!

At the same time I’ve also been able to contribute to the WordPress project (thanks in part to XWP supporting my time), co-leading the 4.9.8 point release of WordPress, speaking at a number of WordCamps, supporting where I could on Gutenberg and other projects, and becoming a Team Rep for the design team.

During this time I’ve been at a completely distributed company. I live in Northern Idaho. My wife and I have two little children, and we’ve been able to live our lives in a way that maximizes time spent with friends and family. Since my daughter was born (she’s almost two years old) I’ve been able to spend so much time with her and watch her grow. That’s a gift and one I’m so thankful to have a job that’s allowed me to do.

Now, I’ve decided to take the next step and move more into Product Design in a way where I can focus on learning and working on projects at scale. The folks at Automattic have been amazing to work with so far (everyone who joins the team has to take a trial project), and I’ll have opportunity to learn alongside an amazing team of designers and developers.

Here’s to the future!

Why design matters in your team

Over the past few years I’ve been privileged to work with some amazing designers and engineers! When you can bring design and engineering together in a true partnership, great things can happen. If either of them are treated as second class citizens, you’ll fall into deep ditches that can sink teams and companies.

“Without a person at or near the helm who thoroughly understands the principles and elements of design, a company eventually runs out of reasons for design decisions. Without conviction doubt creeps in, instincts fail. When a company is filled with engineers it turns to engineering to solve problems, reduce each decision to a simple logic problem, remove all subjectivity and just look at the data. Data in your favor? Ok, launch it. Data shows negative effects? Back to the drawing board. And that data eventually becomes a crutch for every decision.” – Creative Selection

iPad Pro in 2019

Since January 2017 I’ve been an iPad Pro user. For a short period I even made it my primary computer.

It’s become one of the most important tools I have as a Product Designer. Each week I use it to create sketches during the research and conceptual stages of a project.

There are some situations where my MacBook Pro is better as a tool, and other times I prefer my iPhone or iPad.

I’ve tried the 9.7″, 10.5″, 11″, and 12.9″ iPads. Each time I return to the largest screen size. Anything smaller doesn’t work for me. Mainly I choose the bigger screen because I don’t have to zoom in and out of the paper when I’m sketching. Having a larger canvas helps me spend more time concepting and designing.

Following are the reasons I love my iPad.

As a sketching device

Before owning an iPad I sketched a lot with paper and pen. Now I have a digital piece of paper with copy+paste, as well as resize and layering.

This doesn’t mean paper and pen are obsolete. There are still times I need to step away from all electronics and scribble away on paper.

I’ve tried nearly all sketching and drawing apps for the iPad. Linea Sketch is the best for what I need. It has layering, resizing, copy and paste, snapping lines, grids, and simple drawing tools.

Once watercolor becomes a feature I’ll be in love.

As a reading device

This is one area where a smaller iPad is better. I don’t spend large amounts of time reading on this screen, think articles versus books. Anything less than about 15 minutes works well here. If I want to read an interesting article or Google Doc I’ll often open the link on my iPad instead of my MacBook Pro.

This actually helps break up my day! Getting to read on the iPad means I can lean back for a bit and pull away from my desk.

As a notation device

It almost feels like cheating when I use the iPad to redline a document or article. Since I work remotely we pass a lot of Google Docs back and forth between the team. When I’m reviewing something for a colleague I’ll save it as a PDF and open it in Notability. From there I’ll pull out my Apple Pencil and scribble across the document with red lines and notes.

Writing comments with a keyboard in Google docs is fast. But there are times when I want to think through something and write my thoughts by hand. This is where it it’s fun for me. I can again lean back (there’s a theme here) and absorb what’s on the page, giving feedback as I go.

As a consumption device

The iPad is my favorite way to watch videos. Watching on TV is too much hassle, watching on my phone is too small, and watching on my laptop is overkill.

When I’m watching a video for work (or for fun) I like to prop it up on the iPad and play it on my desk or lap.

As a gaming device

Long gone are the days of PC gaming. At least for now. As for console games, I own a SNES Classic.

In the evenings I love propping my iPad up on a pillow, sitting on my couch, and playing a game. Right now I’m enjoy PUBG Mobile. The experience on a 12.9″ screen is perfect.

A brief journey into blocks

WordPress 5.0 has finally launched. It’s been a long time coming, and provides a huge update and change to how the editor works in WordPress. I was privileged to be able to contribute to this release, spending several months in 2017 contributing to design ideas and concepts for early work on Gutenberg.

Earlier this week I decided to try and build a one page site using Gutenberg. I’d played around with blocks, created pages, played with sites, etc. However, I wanted to rely completely on a block interface to build out a complex page.

The journey wasn’t an easy one. I tried out a bunch of the block plugins available.

Will plan to followup when I’ve found a good solution.

The short of all this is I’m looking forward to helping in Phase 2 of Gutenberg, as we try to improve on what’s available and make block building more robust for the future.

Beachbody Editorial UX

In 2016 our team at XWP was able to work with the Beachbody on Demand folks to create a new editorial workflow for the content creation staff. You can read the case study to learn about the work that was done.

During this process I was covering the role of Product Owner for our team, as well as contributing UI/UX support to the editorial workflow. 

Since the content staff needed the ability to upload content regularly, and had a specific flow to how content would be added, we used the Customizer in WordPress to make previewing and saving drafts easier as part of this process. 

Following are a few interfaces to highlight the work I contributed to throughout the project. 

Editorial calendar

Along with the regular programming that gets created for new shows, the team also needed the ability to share training sessions on a per day basis, using a calendar within WordPress. I worked with our team to create concepts and interface ideas that would allow for creating the editorial flow.


We discussed ways to allow for quick translation and localization of the work that happened. In this case the team needed to be able to translate strings of text and have them show in French and English. Following is a clickable prototype showing a proposal for adding strings in multiple languages.