To Start Again

It’s a new year. Though it’s somewhat artificial, I feel the optimism of a fresh start and the possibilities for change. It’s time to simplify and reduce the cruft and clutter that’s accumulated over the past year. It’s time to imagine what can be accomplished and reshape my routine. It’s time to say no.

Last year was characterized by massive change – a new city, a new job, a new baby. All of these were very positive but also incredibly disruptive. Now the dust has settled. Now there is space to pick up what was put down. Now is the time to renew failed efforts.

Regular, intentional writing is the first effort to be revived. I intended to write once a week for two years. I wrote consistently for three quarters of one year instead. I failed, yet I also experienced success. Here’s to starting again.


Since last June, I have followed an arbitrary, self-imposed schedule to write four articles each month. I’ve kept to this schedule and haven’t broken from it – until last week.

I didn’t even realize I had broken my schedule until it was a day too late. The day following the deadline, it dawned on me for no apparent reason. Being preoccupied with a move to a new city, I completely forgot to write. The streak was over.

Coincidentally, that same week, I read an article on the topic of failure. Specifically, it talked about the benefits of letting kids fail. The opening paragraph summarizes its recommended view of failure:

[…] first, to give ourselves the permission to take on challenges where we might very well fail; second, to pick ourselves up as quickly as possible and move on when things don’t work out. This is, I argue, vital on a personal level, as well as vital for the economy, because that’s where innovation and growth come from.

What would the world look like if we never tried anything unless we knew we would succeed? In short, we would not reach our full potential because we’d never push against its boundaries. This is what the author observes happening to kids in our current culture. One B in high school might doom their chances at the perfect college which will in turn doom their chances to a perfect career and any hope of a good life. Or so the thinking goes.

We need permission to be imperfect. As designers, we need it doubly so. There is no great design that is not preceded by failure. It’s a lesson I wish I had learned sooner.

Before learning to embrace failure as part of the design process, the natural inclination is to hide our work. Don’t let anyone else see it until it’s finished and perfect.

We feel this way because, like it or not, designers are judged by their work. It’s not the resume that counts, it’s the work. This is how it should be. However, the worth of our work is too easily confused with the worth of our selves. When these two things are confused, critiques on our work feel too close and too personal for comfort. We seek to hide our imperfection.

Ironically, however, imperfection is where the best design comes from. You have to try, fail, and try again. Each time you try, you get closer to a more elegant solution. The term is iteration in design jargon. The sooner you can get something out on paper, the sooner you can begin refining the idea or realizing you need to start with a different idea altogether.

It’s the same with writing. First drafts are almost always terrible. But the first draft gets the ideas out. It’s a whole lot easier to edit a poorly written text with the seeds of good ideas than it is to edit a blank piece of paper. Getting out those first, scattered thoughts provides a crude outline of what one is actually writing about and trying to say. That’s not always apparent at the start.

It’s the same for design: the solution only becomes clear through a process of creation and failure. The only way to arrive at a great product is to travel down the path of imperfection.

Have I followed my schedule of four articles a month perfectly? No. Have all the articles I have written been perfect, even good? No again. But am I closer to reaching my potential as a writer? Yes. If I waited to write until I could do it perfectly, I never would. I’m getting better because I’m writing. Not the other way around.

Design With Care

Earlier this week, I purchased a new cable modem. Normally, I would have ordered online. However, not having the time to wait for a shipment, I was forced to find a nearby brick and mortar store. The two choices were Staples and Best Buy. I chose Best Buy, as my wife had received an online coupon for the store. I went to Best Buy, picked up the modem, and handed the cashier the modem and my coupon. There was just one problem: he wouldn’t accept it.

You see, after printing it onto a sheet of paper, my wife had cut out the coupon on the dotted lines. And thus, the cashier would not accept it. He wanted the whole sheet of paper, not just the coupon portion. The reason? The rest of the page contained a bar code he needed to scan in order to accept it. This was frustrating.

Never mind that discount amount in question was small. Never mind the corporate policies that prevent retail employees from being empowered to actually help their customers. Never mind the manager at the store who also refused to accept the coupon. Do, however, mind the designer who created the coupon.

Coupons, if you weren’t aware, are traditionally printed on paper. They can be contained with an advertisement or printed together with other coupons in a booklet or flyer. Printed coupons use the convention of a dotted border to indicate what part of the paper should be cut out with scissors so that it isn’t necessary to take the whole booklet or flyer to a store in order to use it.

My wife’s behavior to cut out the coupon on the dotted line was entirely logical and sound. She didn’t want to carry a whole sheet of paper around with her, so she cut out just the portion that she would need as indicated by the dotted lines. After all, that’s how coupons work.

The designer who created the coupon did not understand (or take the time to think about) the function of the dotted lines. Presumably, the designer used dotted lines simply to make the coupon look more coupon-y. But the designer did not consider the function of those lines. If a barcode is indeed needed to process the coupon, it should have been placed within the dotted lines.

This is design. Seemingly small design decisions impact people’s lives. In this case, a decision about dotted lines lead to consumer frustration, an erosion of brand loyalty (not that I had much in the first place), and blame being cast on the wrong person. My wife should not feel blame for having cut out a coupon correctly. The designer should feel the blame for being careless.

Though this example is small and insignificant, the underlying lesson extends to more important contexts. Every detail of a design has the power to affect and influence other people tremendously. It is a large responsibility, and one not to be taken lightly.

Please, design with care.

Simple Means

This morning, I read the following:

Still another step toward simplicity is to refuse to live beyond our means emotionally. In a culture where whirl is king, we must understand our emotional limits. […] Let us repudiate the modern image of the person “on the go,” whose workload is double what any single person can possibly accomplish. Let us reject the delusions of grandeur that say we are the only ones who can save the world. We must learn our emotional limits and respect them. Our children and spouses will love us for it.

Now, as I write in hopes to meet a self-imposed deadline, I simply stop. In a world full of hurry and busy and multi-tasking, I choose to stop, fold up my laptop, and rest. So, instead of the time you would have taken to read a longer article, consider whether you’re living beyond your means emotionally.

I’ll leave you with these words from Richard Foster, who authored the above and below quotes in his book Freedom of Simplicity:

Purposefully, we can cultivate the life of reflection. […] Thinking is the hardest work we do, and among the most important.

It’s not easy to do, but I dare say it’s worth it.

Discovering the Unexpected

Downtown Palo Alto, California is home to a delightful series of street paintings that I recently discovered. Pictured above is the first one I noticed – a man carrying a garbage can with an alien inside. It’s located on an unassuming wall near a street corner. After observing similar paintings around town, I asked a few people about the story behind them. As it happened, the people I asked didn’t know anything more than I did.

The next step in finding more information was obvious: I should Google the paintings. But I held off. I even stopped asking people about them. Why? I realized that part of the fun of the paintings was the surprise and delight that coincides with unexpected discovery. The paintings provide a beautiful and whimsical addition to the ordinary. Not knowing where they came from or where I might see another added to the sense of fun.

As it turns out, the artist who painted the murals, Greg Brown, felt the same way:

I call it the Palo Alto Pedestrian Series because it’s actually geared toward people being on foot, walking around, and discovering these things. People would ask me – they’d say, “I’m coming into town and want to take some friends around. Can you tell me where all these things are, and we’ll drive them around? And I said, “No, don’t do that. That’s not the way to see them. Just go downtown and see how many you stumble upon.” 1

It is interesting to know the way I chose to view the paintings aligned with the artist’s original intentions. And it brings home a good point. Good art can be for no other reason than to have fun and put a smile on someone’s face – especially when it’s unexpected.


Feelings, thoughts, and desires that slowly build over a long period of time and culminate in radical change are difficult to describe.

However, legitimate desires are marked over time. They persist rather than fade. Tastes leave you hungry for more. Foreseen difficulty fails to intimate. Gradually and steadily, they grow until they cannot be ignored.

Waiting for fulfillment is difficult. Deep desires don’t come to pass overnight. Day after day, no movement is observed. Days turn into months turn into a year. Suddenly a shift occurs. Standing in the middle of fruition, the past doesn’t seem so long.

For me, personally, the shift has occurred, foreshadowed by a realization. I am moving to New York City to work as a Product Designer for Palantir.


Exactly one year ago, I sojourned in a monastery in Kentucky for a weekend of silence, prayer, and meditation. Why? I had many questions about work and wanted answers. Was I in the right line of work (digital design)? Was it really what I wanted to be doing? Should I pursue something else? I tried not to get my hopes up that I would return with answers.

While there, I read Tim Keller’s Every Good Endeavor. In it, he distills the Biblical view of work. Two key points stood out and helped guide my thoughts:

1. View yourself as a garden to be cultivated.

Of the talents and gifts that you’ve been given, which have the most potential to be developed? For example, I can play the piano well, but is my gifting such that I could develop enough to play professionally? In my case, probably not. My most potential-laden gift is probably design. I should do my best to cultivate and develop it.

2. View work as a way to help other people.

Work is the primary way in which we serve others. What are the implications? Keller makes it practical: If you have a choice between a job that helps more people but pays less money and a job that pays more money but helps less people, you should seriously consider taking the job that helps more people.

Meditating on these two ideas brought me to a realization: Design is my foremost gifting, and I should pursue design work that truly helps other people.

Suddenly, I had clarity. Design in the digital space not only afforded me the opportunity to develop my skills the most, but to impact the most people. I could now take steps in the right direction. All that was left was to put one foot in front of the other.