The adages abound:

• Life begins at the end of your comfort zone.

• You only live once.

• If you’re comfortable, you’re not alive.

As an entrepreneur, I get taking risks. Clearly, making the safe bet didn’t satisfy someone who started a company or two. No one would call starting and running businesses “comfortable.” (In fact, a friend who just secured funding for her start-up told me last week that she felt “scared to death.” I responded that if she didn’t feel freaked out, I’d question her intelligence.)

Yet I’d counter that constant risk doesn’t make for a good life, either.

To a certain extent, feeling continual pressure and discomfort turn unhealthful—and I’d venture that we can’t count people in constant states of stress as fully “alive,” either. When consumed by concern, we tumble down Maslow’s hierarchy of needs. People can’t feel self-actualized—at their personal apex of creativity, problem solving, and acceptance—without self-esteem, love and security, and fulfilled basic needs. When stressed, people may not feel good about themselves. They may not sense that people are “on their sides.” They may not feel safe.

So how do we weigh the need to push ourselves through our comfort zones into new experiences and thoughts—while ensuring we don’t tip into overwhelming and undue pressure and discomfort? For the natural strivers among us—and I count myself in that category—how should we assess situations and determine how far to go?

Ideas?