When things are going well, it's natural to feel comfortable. The better things go... the more comfortable you get. This isn't just true for humans it applies to companies as well. But in both cases, being uncomfortable is a strategic advantage.
I often got confused looks from co-workers when they asked me how a project was going: "things are going really well, I don't like it." Why would you not like when things are going well? My mindset has always been if things are good, there's more opportunity for them to get worse. But if things are bad there's a lot of room for them to get better.
In reflecting on this, there's an underlying belief that being uncomfortable is a better state to be in than being comfortable. Discomfort means you're not satisfied with the current situation. You know it can be better and you're motivated to make it so.
"It’s wild, but comfort can be a poison— John Nack
In the context of product design, this ends adds up to a mindset that design is never done and there's always things to improve. So you spend time understanding what is broken at a deeper level and keep iterating to improve it. Usually this type of process leads you back to core, critical flows. Fixing what really matters.
When you're comfortable, you instead assume the core product is doing fine and begin to fill time by thinking up what else to do, adding new features, or veering away from what actually matters. Discomfort with the status quo drives urgency and relevance.
"To grow new markets means making yourself uncomfortable. It means you can’t keep doing more of what got you here." -What Steve Jobs taught me about growth
Discomfort is also a prerequisite of doing something new. When you're solving a problem in a different way, it won't be immediately understood by others and you'll get a lot more head shakes than nods of agreement. To get through that, you need to be ok with being uncomfortable. The bigger the change, the longer you'll be uncomfortable.
But how do you motivate yourself and your teams to be uncomfortable? I often find myself quoting the words of the late, great Bill Scott. When explaining how he decided what to do next, he always looked for "butterflies in the stomach and a race in the heart". He wanted to be both uncomfortable (butterflies) and excited (race). Because comfort, while nice, isn't really that exciting.