For my first project since joining 37signals I’ve been working on an update to the venerable Account (Upgrade/Billing) screen in Basecamp. We’ll post more about that update and the process to get there soon, but I wanted to share an experience I had as part of this design.

We had decided to include a few short handwritten phrases as graphic elements. Sometimes in the perfect world of web design, elements that have an organic, handmade look can soften the message and draw the eye. These phrases enhance the message but don’t convey any hard data that is intrinsic to the upgrade decision. That makes them a good place to have a little fun and lighten things up.

Handwritten phrase arrow variations

So, I wanted to make them look as if they’d been casually written directly on the page. They needed to look casual and authentic so no fonts. It can be tempting to use a script or handwriting font for an application like this, but they never fool the eye. I learned a long time ago that you can’t fake it — if you want something to look handmade, make it by hand.

But what I found is that this task was a lot tougher than it sounds. I must have written and re-written some of these phrases more than 50 times trying to get just the right flow, the perfect amount of flair, and a cohesiveness with the other phrases. But “perfect” was exactly the wrong approach here. Handwriting isn’t perfect and the irregularity is where the character and charm I was going for would come from. So I settled for “good enough”, which turned out to be ideal.

So instead of carefully drawing each letter and placing them together, I practiced a few times and just wrote each one out as quickly and naturally as if I was writing in my notebook.

My fingerprints — almost literally — are going to start showing up in 37signals products in the coming weeks. I’ll be sharing more of the process as we go.