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.

Localization

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.

 

Save/Publish in WordPress

You can check out the original Trac issue.

This was such an eye opening feature for me. Several of my team members were discussing the the need to save drafts in the Customizer. I got pulled in and was able to lend UI/UX support to the project.

Over the course of about six months we worked on the issue. I learned a lot about the needs of an open source project, and the importance of understanding the priorities you’re working with. It’s a lot different than simply having a single stakeholder that you’re trying to design for. 

Following are some of my sketches (just a few, there’s more!) showing the process we went through to try and create an elegant solution. 

The project started for me when my teammate reached out with a sketch, proposing some initial ideas for where we could take the flow for saving and publishing. We hopped on a call together and talked through this flow. From there I created a sketch to followup and simplify my understanding of the interface.

This served as the launching point for several further iterations and discussions. The benefit of creating a simple sketch like this, as opposed to a finish prototype, is we could think through problems and have discussions before introducing a ton of extra time into finessing the interface.

From there I kept playing with ideas, based on feedback from the team, with attempts to simplify things and make sure that the flow made sense for a user trying to manage the status of a post.

The process got messy, as the above diagram shows. We played with a lot of ideas, and ended up scrapping most of them.

I began to create some flow diagrams to show how each part of the interface would connect with other parts. 

Finally I shared an Adobe XD prototype (diagram above) with the whole interface worked out. We thought we were in a good place with this.

Until we received some feedback on needing to simplify things again. So, I went back to the drawing board. It’s critical to recognize in any project the need for returning to lower fidelity when confusion arises, or rapid changes are needed. 

After this point I needed to return to client projects, so several of the Core team were able to improve the work here and push the project across the finish line. You can see the final work in the Customizer today within WordPress. 

WordPress Contributions

I spoke about this at WordCamp Seattle 2018, but I wanted to dive into a short post to talk about some of the contributions I’ve been able to make.

Since 2016 I’ve been involved in one way or another, helping out in a number of issues related to the WordPress admin experience.

Here’s the thing, you don’t need to be a developer to make a huge impact on this project. As a designer I’ve been able to help out on a number of issues and make a small impact on the project by being willing to jump in where needed. A few ways I’ve been able to help:

  • Save and publish in WordPress – Working with the Core team on proposing a way to save your work in the Customizer. 
  • Gutenberg – Starting in 2017 I was able to jump into some issues in Gutenberg and start giving UX feedback and support. I wrote about my initial experience
  • Lead support – I’m currently a Design Team Rep and recently Co-led the WordPress 4.9.8 release
  • Speaking – I’ve been privileged to speak at a number of WordCamps

There are so many ways to help out. These are just a few. The sky is the limit. 

WordCamp Seattle talk, with slides

On November 11, 2018 I was able to speak at WordCamp Seattle  on my experience contributing to WordPress Core as a non-developer. In 2017 I wrote about my initial experience, and now now I’ll be planning to expand on what’s happened since. 

Let me tell you, it’s been an amazing ride! For years I’d had interest in helping out in the open source community and supporting the making of WordPress, but I wasn’t sure how to get started. That initial article highlighted the start of my journey.

Since then I’ve been able to help out across a few projects and make a different where I can providing design feedback and at times jumping in to do design work. 

I shared my experience to encourage others to get involved. There are folks from all kinds of backgrounds with wonderful expertise that they could offer to open source projects. A lot of times it takes a little encouragement to figure out how to get started. 

You can download the link to the slides as well!

Quality time over clock time

Jonas Downey, from Basecamp, shared an article this morning about his experience in creative work. I agree 100%. You can read his full article, which I highly recommend. 

“Start thinking about productivity in terms of quality time instead of clock time. You might end up making the same progress with only 20 energetic hours that you would have made in 60 tired hours.”

In creative work I’ve found that 2-4 good hours is far more valuable than 8-12, if it’s the right time of day, and if you can set aside uninterrupted time for deep work. 

When you’re tired, distracted, or in the weeds on something, it’s usually better to stop working. Just admit (temporary) defeat and give yourself a chance to regroup. Do something else that’s less taxing, or call it quits and start again later.”

Agree 100%. Pushing through and slogging is much different than breaking through when you’re in the flow.