Last week, I was catching up with a group of entrepreneurs when one of them asked, “When was the last time each of us felt uncomfortable in our business?” This made me pause and reflect. “Uncomfortable,” in this context, meant doing something outside of our normal approach or comfort zone. Human nature tends to push us forward for a bit, then settle into a routine or style that works. We often hustle with minor adjustments, but rarely do we push ourselves in ways that truly make us uncomfortable.

As the group went around and shared their recent experiences, most examples fell into two categories.

The first was getting uncomfortable with team members. This included addressing personnel issues and making the hard call. For most entrepreneurs, having to fire someone or tell them they’re no longer the right fit is one of the most difficult and painful things to do. Entrepreneurs are typically optimistic, glass-half-full types who love dreaming and chasing a vision, not telling someone the company has outgrown them.

The second category was about risk-taking. While people often assume entrepreneurs are inherent risk seekers, I find many successful ones to be more risk averse in the sense that they value control and like betting on themselves. They often prefer doing their own thing, even if it has a lower chance of success, rather than choosing a safer, more conventional path. The theme of “uncomfortable risk” emerged repeatedly, referring to the shift from calculated, manageable risks to risks that actually create discomfort. Hiring a new team member may involve some personnel risk but little business risk if the company can afford it. Making a bigger bet that could jeopardize the whole business, yet might be necessary to reach the next level, is the kind of uncomfortable risk that keeps entrepreneurs up at night.

For entrepreneurs, my recommendation is to regularly ask yourself where you are on the comfort scale and when you last got truly uncomfortable in a healthy way. It is easy to coast once things are working and push only a little, but it is worth questioning whether you are pushing hard enough and whether there is an opportunity to get uncomfortable in a smart, productive way.