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57 posts tagged with “process”

101 design rules

101 design rules

Musings, ramblings, and principles that I’ve shared with my team and randomly on Twitter. Reminding yourself of the principles that ground you is simply a good practice. Here are mine.

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Still from _The Brutalist_. An architect, holding a blueprint, is at the center of a group of people.

A Complete Obsession

My wife and I are big movie lovers. Every year, between January and March, we race to see all the Oscar-nominated films. We watched A Complete Unknown last night and The Brutalist a couple of weeks ago. The latter far outshines the former as a movie, but both share a common theme: the creative obsession.

Timothée Chalamet, as Bob Dylan, is up at all hours writing songs. Sometimes he rushes into his apartment, stumbling over furniture, holding onto an idea in his head, hoping it won’t flitter away, and frantically writes it down. Adrien Brody, playing a visionary architect named László Tóth, paces compulsively around the construction site of his latest project, ensuring everything is built to perfection. He even admonishes and tries to fire a young worker who’s just goofing off.

There is an all-consuming something that takes over your thoughts and actions when you’re in the groove willing something to life, whether it’s a song, building, design, or program. I’ve been feeling this way lately with a side project I’ve been working on off-hours—a web application that’s been consuming my thoughts for about a week. A lot of this obsession is a tenacity around solving a problem. For me, it has been fixing bugs in code—using Cursor AI. But in the past, it has been figuring out how to combine two disparate ideas into a succinct logo, or working out a user flow. These ideas come at all hours. Often for me it’s in the shower but sometimes right before going to sleep. Sometimes my brain works on a solution while I sleep, and I wake up with a revelation about a problem that seemed insurmountable the night before. It’s exhausting and exhilarating at the same time.

Still from "A Complete Unknown". Timothée Chalamet, as Bob Dylan, in the studio with his guitar.

If there’s one criticism I have about how Hollywood depicts creativity, it’s that the messiness doesn’t quite come through. Creative problem-solving is never a straight line. It is always a yarn ball path of twists, turns, small setbacks, and large breakthroughs. It includes exposing your nascent ideas to other people and hearing they’re shitty or brilliant, and going back to the drawing board or forging ahead. It also includes collaboration. Invention—especially in the professional setting—is no longer a solo act of a lone genius; it’s a group of people working on the same problem and each bringing their unique experiences, skills, and perspective.

I felt this visceral pull just weeks ago in Toronto. Standing at a whiteboard with my team of designers, each of us caught up in that same creative obsession—but now amplified by our collective energy. Together, we cracked a problem and planned an ambitious feature, and that’s the real story of creation. Not the solitary genius burning the midnight oil, but a group of passionate people bringing their best to the table, feeding off each other’s energy, and building something none of us could have made alone.

A winter panoramic view from what appears to be a train window, showing a snowy landscape with bare deciduous trees and evergreens against a gray sky. The image has a moody, blue-gray tone.

The Great Office Reset

Cold Arrival

It’s 11 degrees Fahrenheit as I step off the plane at Toronto Pearson International. I’ve been up for nearly 24 hours and am about to trek through the gates toward Canadian immigration. Getting here from 73-degree San Diego was a significant challenge. What would be a quick five-hour direct flight turned into a five-hour delay, then cancelation, and then a rebook onto a red-eye through SFO. And I can’t sleep on planes. On top of that, I’ve been recovering from the flu, so my head was still very congested, and the descents from two flights were excruciating.

After going for a short secondary screening for who knows what reason—the second Canada Border Services Agency officer didn’t know either—I make my way to the UP Express train and head towards downtown Toronto. Before reaching Union Station, the train stops at the Weston and Bloor stations, picking up scarfed, ear-muffed, and shivering commuters. I disembark at Union Station, find my way to the PATH, and headed towards the CN Tower. I’m staying at the Marriott attached to the Blue Jays stadium.

Outside the station, the bitter cold slaps me across the face. Even though I am bundled with a hat, gloves, and big jacket, I still am unprepared for what feels like nine-degree weather. I roll my suitcase across the light green-salted concrete, evidence of snowfall just days earlier, with my exhaled breath puffing before me like the smoke from a coal-fired train engine.

I finally make it to the hotel, pass the zigzag vestibule—because vestibules are a thing in the Northeast, unlike Southern California—and my wife is there waiting to greet me with a cup of black coffee. (She had arrived the day before to meet up with a colleague.) I enter my room, take a hot shower, change, and I’m back out again into the freezing cold, walking the block-and-a-half to my company’s downtown Toronto office—though now with some caffeine in my system. It’s go time.


The Three-Day Sprint

Like many companies, my company recently debuted a return to office or RTO policy. Employees who live close by need to come in three days per week, while others who live farther away need to go to the office once a month. This story is not about RTO mandates, at least not directly. I’m not going to debate the merits of the policy, though I will explore some nuances around it. Instead, I want to focus on the benefits of in-person collaboration.

The reason I made the cross-country trip to spend time with my team of product designers despite my illness and the travel snafus, is because we had to ship a big feature by a certain deadline, and this was the only way to get everyone aligned and pointed in the same direction quickly.

Two weeks prior, during the waning days of 2024, we realized that a particular feature was behind schedule and that we needed to ship within Q1. One of our product managers broke down the scope of work into discrete pieces of functionality, and I could see that it was way too much for just one of our designers to handle. So, I huddled with my team’s design manager and devised a plan. We divided the work among three designers. For me to guarantee to my stakeholders—the company’s leadership team and an important customer—I needed to feel good about where the feature was headed from a design perspective. Hence, this three-day design sprint (or swarm) in Toronto was planned.

I wanted to spend two to three hours with the team for three consecutive days. We needed to understand the problem together and keep track of the overall vision so that each designer’s discrete flow connected seamlessly to the overall feature. (Sorry to dance around what this feature is, but because it’s not yet public, I can’t be any more specific.)

The plan was:

  • Day 1 (morning): The lead designer reviews the entire flow. He sets the table and helps the other designers understand the persona, this part of the product, and its overall purpose. The other designers also walk through their understanding of the flows and functionality they’re responsible for.
  • Day 2 (afternoon): Every designer presents low-fidelity sketches or wireframes of their key screens.
  • Day 3 (afternoon): Open studio if needed.

But after Day 1, the plan went out the window. Going through all the flows in the initial session was overly ambitious. We needed half of the second day’s session to finish all the flows. However, we all left the room with a good understanding of the direction of the design solutions.

And I was OK with that. You see, my team is relatively green, and my job is to steer the ship in the right direction. I’m much less concerned about the UI than the overall experience.

A whiteboard sketch showing a UI wireframe with several horizontal lines representing text or content areas, connected by an arrow to a larger wireframe below. The text content is blurred out.

Super low-fi whiteboard sketch of a screen. This is enough to go by.

On Day 3, the lead designer, the design manager, and I broke down one of the new features on the whiteboard, sketching what each major screen would look like—which form fields we’d need to display, how the tables would work, and the task flows. At some point, the designer doing most of the sketching—it was his feature, after all—said, “Y’know, it’d be easier if we just jumped into FigJam or Figma for the rest.” I said no. Let’s keep it on the whiteboard. Because honestly, I knew that we would fuss too much when using a digital tool. On the whiteboard, it allowed us to work out abstract concepts in a very low-fidelity and, therefore, facile way. This was better. Said designer learned a good lesson.

Just after two hours, we cracked the feature. We had sketched out all the primary screens and flows on the whiteboard. I was satisfied the designer knew how to execute. Because we did that together, there would be less stakeholder management he’d have to do with me. Now, I can be an advocate for this direction and help align with other stakeholders. (Which I did this past week, in fact.)

The Power of Presence

Keep the Work Sessions Short

I purposely did not make these sessions all day long. I kept them to just a couple hours each to leave room for designers to have headphone time and design. I also set the first meeting for the morning to get everyone on the same page. The other meetings were booked for the afternoon, so the team had time to work on solutions and share those.

Presence Is Underrated

When the world was in lockdown, think about all the group chats and Zoom happy hours you had with your friends. Technology allowed us to stay connected but was no replacement for in-person time. Now think about how happy you felt when you could see them IRL, even if socially distanced. The power of that presence applies to work, too. There’s an ease to the conversation that is distinctly better than the start-stop of Zoom, where people raise hands or interrupt each other because of the latency of the connection.

No Replacement for Having Lunch Together

I’ve attended virtual lunches and happy hours before on Zoom. They are universally awkward. But having lunch in person with someone is great. Conversation flows more naturally, and you’re building genuine rapport, not faking it.

FigJam Is No Match for a Whiteboard and Working Expo Marker

Sketching super lo-fi screens is quick on a whiteboard. In FigJam, minutes are wasted as you’re battling with rectangles, the grid snap, and text size and color decisions. Additionally, standing at the whiteboard and explaining as you draw is immensely powerful. It helps the sketcher work out their thoughts, and the viewer understands the thinking. The physicality of it all is akin to performance art.

The RTO Question

As I said, I don’t want to wade into the RTO debate directly. There have already been a lot of great think pieces on it. But I can add to the conversation as a designer and leader of a team of designers.

As I’ve illustrated in this essay, being together in person is wonderful and powerful. By our very nature, humans are social creatures, and we need to be with our compatriots. Collaboration is not only easier and more effective, but it also allows us to make genuine connections with our coworkers.

At the same time, designers need focus time to do our work. Much of our job is talking with users for research and validation, with fellow designers to receive critical feedback, and with PMs, engineers, and all others to collaborate. But when it comes to pushing pixels, we need uninterrupted headphone time. And that’s hard to come by in an open office plan, of which I’m sure 95% of all offices are these days.

In this article by David Brooks from 2022 in The New York Times, he lists study after study that adds to the growing evidence that open-plan offices are just plain bad.

We talk less with each other.

A much-cited study by Ethan Bernstein and Stephen Turban found that when companies made the move to more open plan offices, workers had about 70 percent fewer face-to-face interactions, while email and instant messaging use rose.

We’re more stressed.

In 2011 psychologist Matthew Davis and others reviewed over 100 studies about office environments. A few years later Maria Konnikova reported on what he found in The New Yorker — that the open space plans “were damaging to the workers’ attention spans, productivity, creative thinking and satisfaction. Compared with standard offices, employees experienced more uncontrolled interactions, higher levels of stress, and lower levels of concentration and motivation.”

And we are less productive.

A 2020 study by Helena Jahncke and David Hallman found that employees in quieter one-person cell offices performed 14 percent better than employees in open plan offices on a cognitive task.

I’m also pretty sure the earlier studies cited in the Brooks article analyzed offices with cubicles, not rows and rows of six-foot tables with two designers each.

The Lure of Closed-Door Offices

Blueprint floor plan of an office space showing multiple rooms and areas including private offices, conference rooms, reception area, restrooms, and common spaces. The layout features a central hallway with offices and meeting spaces branching off, elevator banks and stairs on the right side, and various workstations throughout. The plan uses blue lines on white background and includes furniture placement within each room.

Fantasy floor plan of Sterling Cooper by Brandi Roberts.

Many years ago, when I was at Rosetta, I shared a tiny, closed-door office with our head strategy guy, Tod Rathbone. Though cramped, it was a quiet space where Tod wrote briefs, and I worked on pitch decks and resourcing spreadsheets.

In the past, creatives often had private offices despite the popularity of open-layout bullpens. For instance, in the old Hal Riney building in Fisherman’s Wharf, every floor had single-person offices along the perimeter, some with stunning waterfront views. Even our bullpen teams had semi-private cubicles and plenty of breakout spaces to brainstorm. Advertising agencies understood how to design creative workspaces.

Steve Jobs also understood how to design spaces that fostered collaboration. He worked closely with the architectural firm Bohlin Cywinski Jackson to design the headquarters of Pixar Animation Studios in Emeryville. In Walter Isaacson’s biography, Jobs said…

If a building doesn’t encourage [chance encounters and unplanned collaborations], you’ll lose a lot of innovation and the magic that’s sparked by serendipity. So we designed the building to make people get out of their offices and mingle in the central atrium with people they might not otherwise see.

Modern open space with exposed wooden ceiling beams and steel structure. Features floor-to-ceiling windows, polished concrete floors, and a central seating area with black couches arranged on a red carpet. Café-style seating visible along the walls with art displays.

The atrium at Pixar headquarters.

Reimagining the Office

Collection of bookshelves showing design and tech-related books, including titles on graphic design, branding, and typography. Features decorative items including an old Macintosh computer, action figures of pop culture characters, and black sketchbooks labeled with dates. Books include works by Tufte and texts about advertising and logo design.

**

I work at home and I’m lucky enough to have a lovely home office. It’s filled with design books, vinyl records, and Batman and Star Wars collectibles. All things that inspire me and make me happy.

My desk setup is pretty great as well. I have a clacky mechanical keyboard, an Apple Studio Display, a Wacom tablet, and a sweet audio setup.

When I go into my company’s offices in Los Angeles and Toronto, I just have my laptop. Our hoteling monitors aren’t great—just 1080p. There’s just no reason to plug in my MacBook Pro.

I’ve been at other companies where the hoteling situation is similar, so I don’t think this is unique to where I work now.

Pre-pandemic, the situation was reversed. Not many of us had perfect home office setups, if at all. We had to go into the office because that’s where we had all our nice equipment and the reference materials necessary to do our jobs. The pandemic flipped that dynamic.

Back to the RTO mandates, I think there could be compromises. Leadership likes to see their expensive real estate filled with workers. The life of a high-up leader is talking to people—employees, customers, partners, etc. But those on the ground performing work that demands focus, like software engineering and designing, need uninterrupted, long, contiguous chunks of time. We must get into the flow state and stay there to design and build stuff. That’s nearly impossible in the office, especially in an open-plan office layout.

So here are some ideas for companies to consider:

  • Make the office better than your employees’ home setups. Of course, not everyone has a dedicated home office like I do, but by now, they probably have a good setup in place. Reverse that. Give employees spaces that’s theirs so they can have the equipment they want and personalize it to their liking.
  • Add more closed-door offices. Don’t just reserve them for executives; have enough single-person offices with doors for roles that really need focus. It’s a lot of investment in real estate and furniture, but workers will look forward to spaces they can make their own and where they can work uninterrupted.
  • Add more cubicles. The wide open plan with no or low dividers gives workers zero privacy. If more offices are out of the question, semi-private cubicles are the next best thing.
  • Limit in-person days to two or three. As I’ve said earlier in the essay, I love being in person for collaboration. But then, we need time for heads-down-focused work at some point. Companies should consider having people in the office for only two or three days. But don’t expect designers and engineers to push many pixels or write much code.
  • Cut down on meetings. Scheduled meetings are the bane of any designer’s existence because they cut into our focus time. I tend to want to have my meetings earlier in the day so I can save the rest of the day for actual work. Meetings should be relegated to the mornings or just the afternoons, and this applies to in-office days as well.

After being in freezing Toronto for four days, I arrive back home to sunny San Diego. It’s a perfect 68 degrees. I get out of the Uber with my suitcase and lug it into the house. I settle into my Steelcase chair and then log onto Zoom for a meeting with the feature stakeholders, feeling confident that my team of designers will get it done.

Creative Selection book with Roger Wong's Apple badge

The Apple Design Process

I recently came across Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs by former software engineer Ken Kocienda. It was in one of my social media feeds, and since I’m interested in Apple, the creative process, and having been at Apple at that time, I was curious.

I began reading the book Saturday evening and finished it Tuesday morning. It was an easy read, as I was already familiar with many of the players mentioned and nearly all the technologies and concepts. But, I’d done something I hadn’t done in a long time—I devoured the book.

Ultimately this book gave more color and structure to what I’d already known, based on my time at Apple and my own interactions with him. Steve Jobs was the ultimate creative director who could inspire, choose, and direct work. 

Kocienda describes a nondescript conference room called Diplomacy in Infinite Loop 1 (IL1), the first building at Apple’s then main campus. This was the setting for an hours-long meeting where Steve held court with his lieutenants. Their team members would wait nervously outside the room and get called in one by one to show their in-progress work. In Kocienda’s case, he describes a scene where he showed Steve the iPad software keyboard for the first time. He presented one solution that allowed the user to choose from two layouts: more keys but smaller keys or fewer keys but bigger. Steve asked which Kocienda liked better, and he said the bigger keys, and that was decided.

Before reading this book, I had known about these standing meetings. Not the one about software, but I knew about the MarCom meeting. Every Wednesday afternoon, Steve would hold a similar meeting—Phil Schiller would be there too, of course—to review in-progress work from the Marketing & Communications teams. This included stuff from the ad agency and work from the Graphic Design Group, where I was.

My department was in a plain single-story building on Valley Green Drive, a few blocks from the main campus and close to the Apple employee fitness center. The layout inside consisted of one large room where nearly everyone sat. Our workstations were set up on bench-style desks. Picture a six-foot table, with a workstation on the left facing north and another on the right facing south. There were three of these six-foot tables per row and maybe a dozen rows. Tall 48” x 96” Gatorfoam boards lined the perimeter of the open area. On these boards, we pinned printouts of all our work in progress. Packaging concepts, video storyboards, Keynote themes, and messaging headlines were all tacked up. 

There was a handful of offices at one end and two large offices in the back. One was called the Lava Lounge and housed a group of highly-skilled Photoshop and 3D artists. They retouched photos and recreated screenshots and icons at incredibly-high resolutions for use on massive billboards in their dim room, lit only by lava lamps. The other office was for people who were working on super secret projects. Of course, that was badge access only. 

My boss, Hiroki Asai, the executive creative director at the time, sat out in the open area with the rest of us. Every day around 4pm, he would walk around the perimeter of the room and review all the work. He’d offer his critique, which often ended up being, “I think this needs to be more…considered.” (He was always right!) A gaggle of designers, copywriters, and project managers would follow him around and offer their own opinions of the work as well. In other words, as someone who worked in the room, I had to pin up my work by 4pm every day and show some progress to get some feedback. Feedback from Hiroki was essential to moving work forward.

So every Wednesday afternoon, with a bundle of work tucked under his arms, he would exit the side door of the building and race over to IL1 to meet with Steve. I never went with him to those meetings. He usually brought project managers or creative directors. Some of the time, Hiroki would come back dejected after being yelled at by Steve, and some of the time, he’d come back triumphant, having got the seal of approval from him.

I like to tell one story about how our design team created five hundred quarter-scale mockups to get to an approval for the PowerMac G5 box. In the end, the final design was a black box with photos of the computer tower on each side of the box corresponding to the same side of the product. Steve didn’t want to be presented with only one option. He needed many. And then they were refined.

The same happened with the Monsters, Inc. logo when I was at USWeb/CKS. We presented Steve with a thick two-inch binder full of logo ideas. There must have been over a hundred in there.

Steve always expected us to do our due diligence, explore all options, and show our work. Show him that we did the explorations. He was the ultimate creative director.

That’s how Steve Jobs also approached software and hardware design, which is nicely recounted in Kocienda’s book. 

In the book, Kocienda enumerates seven essential elements in Apple’s (product) design process: inspiration, collaboration, craft, diligence, decisiveness, taste, and empathy. I would expand upon that and say the act of exploration is also essential, as it leads to inspiration. In Steve’s youth, he experimented with LSD, became a vegetarian, took classes on calligraphy, and sought spiritual teachers in India. He was exploring to find his path. As with his own life, he used the act of exploration to design everything at Apple, to find the right solutions.

As designers, copywriters, and engineers, we explored all possibilities even when we knew where we would end up, just to see what was out there. Take the five hundred PowerMac G5 boxes to get to a simple black box with photos. Or my 14 rounds of MacBuddy. The concept of exploring and then refining is the definition of “creative selection,” Kocienda’s play on Darwin’s natural selection. But his essential element of diligence best illustrates the obsessive refinement things went through at Apple. Quality isn’t magic. It’s through a lot of perspiration.

Plastic storage bin filled with obsolete media formats including Zip disks, floppy disks, CDs, MiniDiscs, and labeled data backups.

My Backup Plan

Did you know that March 31 was World Backup Day? Yeah I didn’t either. But for shits and giggles, I decided to finish writing this post which I had started late last year. Hope you enjoy…

Anyone who works with any type of data files should have a comprehensive backup plan. Which pretty much means everyone who uses a computer. As a designer who’s been working professionally for over 20 years, having a good solution that works is incredibly important. Over the years I cobbled together something that works for me, but I wanted to codify it and share it, in case it might work for you.

The Crash

I’m a data packrat. Since my early days with my 512K Mac, I’ve tried to save everything that I’ve produced. Therefore there’s a big plastic bin filled with 400KB and 800KB floppies, DAT backup tapes, SyQuest cartridgesZip disksJaz disks, CD-Rs, and SCSI hard drives, containing many years of work. Eventually, I’d like to extract all those files onto a modern medium, like say, the cloud, but that’ll have to wait until I have much more time on my hands.

Anyway, as a designer, I accumulate a lot of work files. At some point in the mid-aughts, I had a massive hard disk failure on my main work drive, which contained portfolio pieces from three or four jobs. Five-to-seven years of archived work disappeared with a screech. I sent the poor silver LaCie Big Disk (all 2GB worth!) to a data recovery company and crossed my fingers. A couple of weeks and $2,000 later, all they were able to recover was about 60% of the data, in loose, unorganized files, some even with generic names like “Photoshop Document 01.psd.” Because a lot of my work from that time were Adobe Illustrator or QuarkXPress files with placed assets, it was all pretty much useless. Sigh.

Since then I vowed to always back up my work onto a redundant medium. Enter RAID.

Redundancy

RAID stands for Redundant Array of Independent Disks. It’s a technology that acknowledges that failure is inevitable and therefore builds in redundancy. There are a number of RAID levels which you can read about here. The gist is, for almost any RAID level except 0, if one of the hard disks fail, the data will still be protected. The first device I purchased was a 1TB Buffalo Terastation Networked Attached Storage (NAS) to which I manually copied all my music, photos, and whatever archived work I had left.

It worked fine for a couple of years until my storage needs started to grow exponentially (I just had a child and therefore wanted to take digital pictures of everything she did!). But I realized that upgrading the storage on the Terastation wasn’t exactly easy. While theoretically it was RAID 5 and pulling out a hard disk and replacing it with a bigger one should have been fine (then repeat for each of the four disks), I just wasn’t confident. The tools they had at the time made it look like a chore. So the next move was to a Drobo.

Drobo’s proprietary RAID system seems like a dream because I could expand it whenever I wanted to! It also involved me getting a Mac mini and connecting the Drobo to it, since they didn’t have a NAS option at the time. Also around this time I discovered CrashPlan. So now I could use CrashPlan to continuously back up to the cloud and to my Mac mini plus Drobo server. Additionally, I had CrashPlan running on the Mac mini and it backed up the entire Drobo to CrashPlan’s datacenter as well.

The Mac mini plus Drobo combo served me well enough for a few years. But I did have a couple of complaints. First of all, the Drobo model wasn’t exactly quiet. With the Mac mini in the living room and part of the entertainment system, the device was just a bit loud. Secondly, the Mac mini was mostly idle as I didn’t really use it much to view media on my TV. Yes, I could have solved the first issue by moving the Mac mini out of the living room since it wasn’t really necessary for it to be there. But I didn’t.

Because I’ve had to move around a bit in the last few years, the mini and Drobo went into storage. Recently I finally settled down and started to think about setting up the Mac mini + Drobo server again. But I also knew that it had been in storage for over four years. My hunch was that it would be dicey, so I decided to upgrade to a new NAS.

Synology NAS device

In the years since buying the Drobo, NAS technology really accelerated. Modern NAS servers seem to have come down to two brands: Synology and QNAP. After much research, I purchased the Synology DS916+, a four-bay NAS, and I outfitted it with four 3TB drives, formatted the unit as RAID 10, for a total of 5.5TB of storage. Synology’s DSM operating system software is pretty cool in that you can install numerous apps and use it as a mini server. Although it’s really not recommended that you use a NAS server for anything robust, as their processors are usually underpowered. I chose to format the volume as RAID 10 for both redundancy and speed. Although in hindsight, I would probably use Synology’s SHR format next time to eke out a little more space.

Once set up, I dug the Drobo out of storage and plugged it in. It didn’t sound too great at all—after all those platters hadn’t spun in over four years. But it stayed alive long enough for me to retrieve all the data and copy it onto the Synology. Years of work, photos, and music data was safe again.

Comprehensive Backup Plan

Enough backstory, here’s the plan. The best backup plan is the kind that you don’t think about because it’s automatic and constant. To have to manually think to back up your files is an immediate fail. Because you won’t remember.

For me, the goals of my backup plan are:

  • Access to 100% of my data from anywhere
  • At least two redundant copies of 100% of my data
  • Automatic and always running
  • Security

To reach those goals, the solution really calls for a two-pronged approach: local and cloud. Local is handled by the Synology NAS plus CrashPlan. And cloud is handled by a combination of CrashPlan and Dropbox.

Diagram showing a backup plan

Local

For Macs, Apple has a built-in backup solution called Time Machine. You can switch it on and point it to an external hard drive, or to a network-mounted drive, like a NAS. But it’s for local backups only. And since I was already using CrashPlan to back up to the cloud, I can also use CrashPlan to back up to my Synology NAS. It’s automatic and always running in the background. If I need to restore anything—like I accidentally deleted a file—I can do so via the copy on my NAS, which would be a lot faster than from the cloud if it were a huge file.

Diagram of local backup plan

With CrashPlan backing up to my NAS, I always have two local copies of every file.

Cloud

A key part of my workflow is Dropbox. All my project files are placed into Dropbox for realtime cloud backup and sync. And while I’m always really good at saving versions and iterations, there’s also the peace of mind that I can revert via Dropbox if I needed to. And best of all, I can always access work on my iPhone while on the go, in case a client needed a file and I was nowhere near my computer. Which I’ve used at least a few dozen times. I can’t recommend enough to use Dropbox in your daily workflow.

Now Dropbox is great, but there are limitations. Their upgraded individual plan is only 1TB, so it’s not great for my archival purposes. My music and photos alone take up over 600GB.

I’ve mentioned CrashPlan a couple of times already in this piece, but let me dive a little deeper. I install CrashPlan onto every computer I own—my MacBook Pro, my PC, and my wife’s MacBook. I have it back up my user folder which contains all my data files, including everything that’s synced with Dropbox. CrashPlan will also keep versions of files. And all my backup data is encrypted so no nefarious entity can go digging through my data.

Diagram of cloud backup plan

Adding Dropbox and CrashPlan, I now have two copies of the same file in the cloud. This means for any given file, there are four copies: two local and two in the cloud.

Now the only piece of the solution that isn’t being backed up is the NAS. Back up the backup? Yes! Redundancy, redundancy, redundancy! I back up the Synology NAS to the cloud as well since it contains archives of project files, photos, and music. I do not back up the CrashPlan and Dropbox data that’s on the NAS. But for everything else, I use Synology’s built-in Cloud Sync app to sync with Amazon Cloud Drive. This awesome service from Amazon gives you unlimited storage for one flat yearly price. Well worth it.1

Security

With revelations from Edward Snowden about how the NSA and other spy agencies had developed tools to snoop on Americans, I—and the rest of the web—have been much more aware of security. That’s why for all of the cloud services I mentioned, I’ve enabled both encryption of my data as well as two-factor authentication where available.

I like my plan and it works well. But it is missing something. Namely all the pictures and videos I take with my iPhone are only getting backed up in one place—Apple’s iCloud. Yes, the media is also on my MacBook Pro which is backed up to the NAS, but it’s fleeting and gets deleted automatically when I’m running low on space and macOS decides to optimize my storage. I wish there were a direct way to sync all my photos to my Synology NAS as well. But in my research so far, it doesn’t seem possible. Will need to revisit this one in the future.

Conclusion

The origin of my backup fanaticism is tragic, but as certain as death and taxes are, so is data loss. Hard drives crash, laptops get stolen. It will happen. While my backup plan might seem overkill for your needs, feel free to tweak and modify as necessary. At the very least get a cloud backup solution like CrashPlan2 so that your data is protected at least once. Fit Dropbox3 into your workflow if you generate any amount of files. And then add a NAS when you can.

Having a comprehensive backup plan that’s automatic, that you actually use, will ensure that you can recover quickly and easily when one day you hear a big screech from your hard drive.

Notes:

1 There is a way to install CrashPlan on the Synology NAS as well. I tried this for a couple of months, but ultimately gave up on it. It’s not an officially-supported platform for CrashPlan and took up a huge amount of resources from the low-powered processor in the NAS. Using Cloud Sync to back up to Amazon Cloud Drive was the best solution I could figure. However, it is only a copy of the current state of the NAS, and not a true backup with versions.

2 There are other great cloud backup solutions besides CrashPlan. For features and pricing, CrashPlan continues to be the best fit for my needs. Check out this excellent roundup of backup services from The Wirecutter for other options.

3 Dropbox was the first to the market with a cloud sync solution that just worked. I’ve tried Google Drive, Box, OnDrive, and others, but Dropbox works best for me. Feel free to explore the other sync solutions.

Smartest Time to Buy Infographic

Smart Data Needs Smart Design

Infographics have exploded over the past few years. It’s a great way to visually and simply explain sometimes complex data to a general audience. My own personal brand of infographics is more on the data visualization side, and thankfully coincides with TrueCar, my employer. I believe that data should be presented in a beautiful and sophisticated way. It should be easy to grok and doesn’t have to be cutesy.

When the latest epic infographic™ project landed on my desk, I started where I always start—I looked at the data. What inspired me was seeing this color-scaled chart of the smartest day of the year to buy. Just by looking at the color I quickly understood the patterns: end of the month, December is the best month, and January 1 is the best day.

Color-coded spreadsheet showing percentage values by day of the month across all twelve months, labeled “Day of transaction” on the left and “Day of Month Average” on the right. Cells are heatmapped from red (lower values) to green (higher values), visualizing performance trends or rates by calendar date.

Best Day Excel

From there I looked for inspiration on cool calendar designs. The notion of color scaling was present in a few examples, and I also really appreciated the circular format in some. Years are cycles, plus a circle is an inherent shape in cars (tires, steering wheel, speedometer, knobs). My search led me to this lovely piece by Martin Oberhaeuser. With much respect to his design, I used it as a jumping-off point to transform the above table from Excel into something hopefully more elegant.

Radial infographic by TrueCar showing the average percentage off MSRP for each day of the year, based on 2010–2014 data. Each ring represents a month, with darker blue indicating better car discounts. January 1st is marked as the best day to buy a new car, with the highest average discount.

Using TrueCar’s color palette of a couple of blues, I made a color scale—lighter being better, and orange being the best—and inserted the actual percentage value within each cell.

For the chart to show the best month to buy, I combined a calendar and a column graph. And it validates the long-held belief that December is the best month of the year to buy a new car.

Bar chart comparing average percentage savings off MSRP by month. December is the best month to buy a car with 7.72% average savings, followed by September and October (both at 7.63%). January has the lowest average savings at 6.80%.

The most helpful data I thought we had was the one about the smartest month to buy a particular kind of car. While December remains the best overall month, if you’re looking to buy a subcompact, you should buy in June. Since I had a circular table already I decided to leave this one pretty straightforward.

Matrix showing average discount percentages by month for different vehicle categories. December is best for large cars, premium cars, and midsize utilities, while May is best for small utility vehicles and subcompact cars. The data reveals variation by vehicle type and seasonal sales strategies.

Last, but not least, is the best day of the week to buy a car. There’s really only seven data points here so presenting the data simply seemed the way to go.

Bar chart showing average savings off MSRP by day of the week. Wednesday offers the highest average discount at 7.40%, followed by Monday (7.36%) and Friday (7.33%). Saturday and Sunday have the lowest savings, with Saturday at 6.98%.

I actually designed the infographic as one long piece first, and then broke it into smaller graphics for social media sharing. As a whole piece I think it works really well. There’s a story that weaves it all together. I hope you enjoy it!

Comprehensive infographic from TrueCar analyzing the best time to buy a car by day, week, month, and vehicle segment. Includes a circular heatmap of daily savings, bar charts for best months and weekdays, and a matrix showing savings by vehicle type across months. December and Wednesday are highlighted as offering the highest discounts.

Exotic car marques timeline

Designing a Data-First Infographic

A radial timeline infographic showing the ownership history of exotic car brands like Ferrari, Bugatti, Porsche, Land Rover, and others. The diagram uses colored segments for each brand and maps mergers, acquisitions, and transitions from the early 1900s to the 2010s.

At TrueCar, data is our lifeblood and visualizing that data in a compelling way is important. Finding that compelling way takes time. We’ve produced a number of infographics recently. Some have been more involved than others, but all as a way to find our voice in telling a story through data.

Timeline chart showing the growth of TrueCar’s certified dealer network from April 2006 to September 2014, growing from launch to 9,000 dealers. Key milestones are marked at each 1,000-dealer increment.

Heatmap-style chart showing monthly incentive spending (in % and dollars) from January 2009 to October 2014. Circle size and color represent spending levels, with the highest occurring in March 2009 (11.24%).

Grid of pie charts visualizing 2014 forecasted U.S. auto sales by segment—cars, pickups, utility & vans, and premium—for major OEMs like Ford, GM, Toyota, and Volkswagen. Each chart shows revenue by vehicle type in billions.

The Assignment

This project was initiated because Fiat is going to spin off Ferrari as a separate company. They’ve owned the brand for over 40 years. So we wondered how long other exotic makes have been owned? The CorpComm team—my internal client—was thinking a simple chart showing the years of ownership. It could have probably been designed easily and in a few hours. But I saw potential in telling a richer story and producing a cooler artifact while still getting the point across. I didn’t quite know what form the final graphic would take. It warranted some research, inspiration, and exploration.

Stacked horizontal bar chart comparing performance or ratings across six luxury car brands (Porsche, Jaguar, Rolls Royce, Bentley, Lotus, Ferrari). Bars are color-coded by categories labeled “Current” through “-6,” though the chart is missing a title.

Research

While the team did provide me with some data, I decided to look into the histories of all these makes. Just to get a feel for the material. I ended up spending a full day in the bowels of Wikipedia and other exotic car enthusiast sites tracking down each time a brand changed hands or changed names. What I found was a sometimes—in the case of many of the British brands—fascinating spaghetti of bankruptcies, auctions, nationalizations, and spin-offs. This added much more depth to the pure numbers that I was given, and a timeline form started to wander into my head.

Inspiration

I recalled seeing an infographic about the history of automobile companies a few years ago. It’s called “The Genealogy of Automobile Companies” and was expertly designed by Larry Gormley. He presents the information about the explosion of auto startups in the early 20th century and how over time it all starts to consolidate. It’s a classic.

My dataset is different because it’s only about foreign exotic makes, but it tells a similar story of consolidation. Additionally the story is also about the changing of owners. I didn’t want to repeat the same form and really needed to show the information in a style consistent with TrueCar’s high-tech brand.

I’ve always admired the infographics from the New York Times. Their graphics team has done a tremendous job of using a variety of techniques to bring life to the data. They have no visual style per se, yet their signature is clarity.

I also flipped through the massive tome called Information Graphics by Sandra Rendgen. While ultimately I didn’t find the perfect form in the book for my data, it certainly opened my eyes to the possibilities.

Exploration

I began to explore different formats. I knew my dataset and knew that my goal was to show the winding paths that each of these car makes took to get where they are today. Like abandoned orphans bouncing from foster home to foster home, many of these brands’ lineages tell stories of rich men, fast cars, and terribly stupid financial decisions. What form could tell that story?

A sketch of a simplified vertical timeline showing the movement of car brands between parent companies from 1906 to 2014. The right side lists parent brands like Fiat, Aston Martin, and Volkswagen.

Left sketch shows a radial segment labeled “Rolls” with a branching ownership path ending at VW and BMW. Right sketch shows a horizontal flow where each row represents a corporate entity, with curved lines connecting ownership transitions.

A sketch showing two visual ideas: a 3D-style stepped timeline at the top and a curved path-based diagram underneath that maps brand transitions over time.

Three visual ideas: a circular loop diagram, a starburst layout with converging lines, and a labeled radial chart illustrating the flow of brand ownership over time through a central hub of holding companies.

Black line diagram on a white background showing brand ownership transitions from 1910 to 2010 for marques like Ferrari, Maserati, Bugatti, Lotus, and Jaguar. Lines connect across parent companies including Fiat, Proton, VW, BMW, Ford, and Tata Motors.

When I thought more about the data, it occurred to me that this was really about ancestry—about who begot whom. So I looked into examples of family trees and genealogy fans.

Side-by-side image of two radial genealogy charts. The left chart is a colorful, fan-shaped ancestral tree labeled “GENEALOGY,” showing paternal ancestors in blues and greens and maternal ancestors in reds and yellows. The right chart is a black-and-white diagram titled “Ancestors, Children and Grandchildren of Darius Mead,” showing family lineage in a semicircular format with names and birth dates.

Solution

The data and the resulting infographic didn’t turn out to be a very screen-friendly. Instead it is a data-intensive multi-layered intricate 24″ x 36″ printed poster meant to be looked at up close.

Zoomed-in radial timeline showing Land Rover and Jaguar brand ownership changes, including mergers, spin-offs, and government nationalization from the 1940s to 2000s. Uses colored bands to represent corporate affiliations.

Radial chart segment showing historical ownership and acquisitions of Lotus, Proton, and Aston Martin, from the 1970s to the 2010s. Key milestones include Ford, GM, Toyota, and Tata Motors.

Time is indicated by the radial lines, from 1906—when Rolls-Royce started—through 2014. Each slice of the semi-circle indicates a brand. The outside starting color is their brand color with a watermark of their original logo. Each change in color within each slice indicates change of ownership or name. As you can see with Maserati and Ferrari, Bentley and Rolls-Royce, and Land Rover and Jaguar, sometimes owners are shared. Ultimately—with the sole exception of Aston Martin—all marques lead to larger corporate parents like Volkswagen AG today who own a multitude of these makes under one entity.

A radial timeline infographic showing the ownership history of exotic car brands like Ferrari, Bugatti, Porsche, Land Rover, and others. The diagram uses colored segments for each brand and maps mergers, acquisitions, and transitions from the early 1900s to the 2010s.

In the end, I don’t think the final solution would have come about had I not gone through the process and spent time getting immersed in the data, looking for design inspiration, and exploring the possibilities. It’s the industry-tested universal design process. But spending a full day getting lost in the history of all these car makes helped me synthesize the data into something bigger. And then spending time to look at hundreds of other infographics helped me break out of any preconceived design notions. The first thought is often wrong and lazy. Finally in sketching, I was able to land on something compelling.

Having spent the last seven years of my career as a creative director, my job is usually more about ensuring my designers are set up to do their best work. Therefore it’s a rare opportunity to design something from start to finish and to obsess over the little details so completely.

I must also mention that having an open-minded client helped a lot too. The CorpComm team at TrueCar gave me a starting point and a long leash.

It was a fun ride and I’m proud of the result.

Download the high-res PNG (4096x2740 3.3MB)

Download the PDF

A Short Note about Craft

The final infographic was worked on over a number of weeks. After finishing the initial design—which was a focused weeklong marathon—I spent a lot of time tweaking the colors for screen and for print. I also had to completely flatten my Adobe Illustrator file to get rid of anti-aliasing artifacts. I originally built the file with a series of masks—one for each slice or marque. But the adjacency of the colors and paths wreaked havoc on the anti-aliasing algorithm and it just looked bad. I knew it would be fine printed, but it also needed to look good on-screen.

Side-by-side visualization comparing “Before” and “After” versions of a brand history graphic for Land Rover. Both versions show key ownership and corporate changes from 1948 to 2008, using colored sectors and curved text paths.

Scene from the TV show Mad Men featuring Peggy Olson seated at a desk with a quote beside her: “If you can’t tell the difference between which part’s the idea and which part’s the execution of the idea, you’re of no use to me.” – Peggy Olson.

Walking Over The Same Ground

Watching the premiere of Mad Men season six, I loved that Peggy Olson blasted her creative team for bringing her three variations on the same idea. These are words to remember.

Those are three different versions of the same idea.

If you can’t tell the difference between which part’s the idea and which part’s the execution of the idea, you’re of no use to me.

…Well I’m sorry to point it out, but you’re walking over the same ground. When you bring me something like this, it looks like cowardice.