U.S. Navy photo by Mass Communication Specialist 2nd Class Kristopher S. Wilson/Released
One of the biggest challenges small business owners face is isolation. Being small by nature, there are few people around to bounce new ideas off. And let’s be honest—no employee wants to tell their boss they need to improve. For fear of reprisal, most staff keep quiet. Yet without outside feedback, it’s nearly impossible to grow. That’s where a mentor comes in.
In many conversations I’ve had with clients, I hear the same refrain: “I don’t want a partner because I want to call all the shots.” On the surface, it sounds like independence. But underneath, it often signals a deeper issue: a resistance to feedback. What I really hear is, “I don’t want anyone challenging me or telling me I might be wrong.” That’s a dangerous mindset for any entrepreneur.
Think about the world of professional sports. Legends like Wayne Gretzky, Joe Montana, Michael Jordan, Michael Phelps, Muhammad Ali, Babe Ruth, and Pelé were the best of the best, masters of their craft. Yet every single one of them relied on guidance beyond themselves. Yes, they had coaches on the field, but they also leaned on advisors, trainers, and trusted insiders who helped them see blind spots and refine their game. Even the most talented performers know they can’t see everything from their own perspective.
Business is no different. Entrepreneurs who try to go it alone often fall into the trap of believing perseverance alone will solve every problem. They double down on bad habits, assuming that doing more of the same will eventually get them across the finish line. However, if the habits are bad, more effort won’t fix them. What they really need is a trusted mentor, someone outside the business who can offer perspective, challenge assumptions, and share lessons learned from their own lived experience.
That’s why organizations like SCORE were so valuable for decades, offering free mentoring to business owners. The Small Business Development Center (SBDC) continues to provide excellent functional expertise as well. But many business owners resist reaching out, worried that inviting feedback will bruise their egos. Ironically, that avoidance often holds them back from the very success they’re chasing.
Of course, mentoring doesn’t always come from a formal engagement with a professional mentor. Sometimes it’s a business partner willing to offer candid observations. Sometimes, it’s a volunteer advisory board composed of peers, vendors, and customers. In my own businesses, I often created advisory boards for precisely this reason—to gain outside perspective and hear the truths I couldn’t always see from inside the trenches.
History offers another useful metaphor. In a monarchy, kings wielded absolute power, much like today’s business owners. The smartest kings surrounded themselves with jesters. On the surface, the jester’s role was to entertain. But in truth, by poking fun at the king, the jester held up a mirror—helping the king see things from a different angle. That outside voice kept hubris in check and made the king a more effective ruler.
As business owners, we all need our own “jester”—that trusted mentor or advisory group who can speak truth without fear. It’s not always comfortable to hear, but it’s essential if you want your business to reach its full potential.
Do you have a mentor or a jester to help you see where you need to improve?
