Anthony Casalena

In the early years of Squarespace, I approached everything like an engineering and design problem because that was my background and that’s what I was good at. It’s easy to fall back on the skill set that you’ve developed instead of learning how to do new things. It’s hard to say “I’m not good at hiring, and I don’t have a network. I need to get better and not treat everything the same way.” The lesson is that what made you successful in the past isn’t necessarily going to make you successful in the future. The same thing applies to Squarespace. Look at our industry and how technology and websites have evolved—just because we’ve been good at something in the past, it doesn’t mean that’s where our future lies.

OUTTAKES

TECH LINGO

“Context switching” is a computer science term, but it applies to productivity too. When you switch activities—like going from a call to designing something—it takes you out of your thought stream. I try to avoid the switch as much as possible.

MINDFUL READ

Thinking, Fast and Slow by Daniel Kahneman is illuminating. It looks at how the mind works and its various biases.

WEB EVOLUTION

You don’t see the level of design clutter that you used to, because a million sidebars or navigations won’t work on mobile. The iPhone forced designers to simplify, and that’s been a good thing.