Consider what life would be if we only did what we know, what we were already good at or what we currently liked. We would never grow.

It’s no wonder babies cry when they are pushed from the safe and nurturing confines of their mothers’ womb and into the brightly lit, cold confines of the world itself. And yet, despite all of our experience at adapting and stretching ourselves in one way or another, it still makes us uneasy. Learning happens outside of the familiar and comfortable. This isn’t news for experienced entrepreneurs, who have learned the hard way that trying, failing, changing directions and trying again is often the only way to succeed.

But is there such a thing as venturing too far from the known? At what point is learning replaced with simply inducing fear or anxiety just to say you did?

Imagine a person who is afraid of heights generally, but still willing to ride roller coasters. The key is to have a full understanding and trust of the safety measures in place and a learned expectation of their own physiological response. In other words, they know their limits and prepare for the times when they are willing to push those limits.

Researchers have long known that the brain is primed for learning when the outcome is uncertain, marked by increased activity in the frontal lobe. In a 2018 study, researchers found that participants were willing to take risks if even a small chance of reward was present—20 percent of the time, in this case.

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To set aside the analogy of the person afraid of heights, taking a risk isn’t always about facing your greatest fear. Maybe your version is trying a new restaurant or striking up a conversation with a stranger. Start small. The payoff isn’t as big, but neither is the risk.

Best-selling author Brené Brown begins each day with the mantra, “Today, I’m going to choose courage over comfort.” Choosing courage, in all its forms, challenges our preconceived notions and expands our comfort circle. As your comfort circle increases, so does your willingness to tackle bigger risks.

Finding the sweet spot of comfort and discomfort requires preparation, honesty and of course some risk. Start by asking yourself the following questions, then check out the advice from three entrepreneurs who share their experiences with staying uncomfortable.

  • Have you done the work to ensure you’re prepared for this type of risk?
  • Is it worth it? Taking a risk for the simple pleasure of overcoming a fear or insecurity is great, but is your time better spent on something more personally or professionally gratifying?
  • Is this the best time to leave your comfort zone? If you’re in a tough financial spot, for example, now may not be the best time to launch a new business.
  • Are there less-risky options that would provide you some building blocks on which to expand your comfort circle?
  • How will you respond to failure? Venturing too far from your comfort circle can drain your motivation to try again.
  • Is there a trusted friend or colleague who can support you through this risk?
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