Part II
Small business owners are often viewed as being tactically oriented: problem solvers, analytical, bottom-line driven, and inclined toward a command-and-control style. While these traits are certainly part of the picture, I believe it’s an incomplete one.
For me, one of the most gratifying parts of the breakout sessions was seeing another side of business owners that I’ve written about in the past. These are people who are curious, thoughtful, caring, and deeply introspective.
The next question I posed drew on a pattern I’ve seen both in myself as a business owner and in many of the clients I’ve worked with as they and their businesses have matured: How has your definition of success changed as you’ve gotten older?
For many owners, the early years were all about survival: doing good work, landing customers, generating cash, hiring employees, and somehow making payroll—on the weeks there even was one. The focus was simple and direct: keep the doors open and the truck moving.
But as participants talked through their experiences, a common theme emerged. Their definition of success had shifted over time. What began as a “truck and money” mindset had evolved into something deeper: leading people and building belief within their teams.
What once felt like a race for accumulation had matured into a pursuit of purpose, where success meant creating a workplace where everyone could grow.
For many, success now looks less like personal achievement and more like empowering others, building stability, and shaping a culture where people genuinely enjoy coming to work. Smooth operations, fewer headaches, and a little more time for life have become not just nice-to-haves, but meaningful measures of progress.
In short, our definition of success evolves, just like we do.
The third question I asked was: What tasks or decisions were the hardest for you to let go of, and why?
When the conversation turned to letting go of responsibilities, the room got noticeably quieter. Most owners admitted that handing off tasks wasn’t just about process, it was about ego. Some feared that quality would slip if they weren’t the ones doing the work. Others worried, sometimes quietly, that giving up key decisions might make them feel unnecessary or even irrelevant. And for many, it was simply more comfortable to keep doing what they’d always done than to step into a new role they weren’t quite sure they were ready for.
Another challenge came from the people side of the equation. Delegation is easy in theory, but it only works if someone capable is ready to take the reins. Several owners acknowledged that their companies had talent gaps or lacked obvious next-generation leaders. In those cases, delegation became a tug-of-war, swinging from tight control, to frustrated dumping, and sometimes even to outright abdication.
What many came to realize is that growth requires self-examination. To attract stronger people, leaders must be willing to make space for them. And to delegate effectively, they have to accept that different doesn’t mean worse. It just means different. That doesn’t mean lowering standards. It means allowing others to meet them in their own way.
Letting go will always feel vulnerable. But when owners entrust capable people with meaningful decisions, something important happens. The culture gets stronger, leadership rises to a higher level, and the team gains confidence.
In the end, the willingness to release control often becomes one of the clearest signs of a leader’s growth.
Hear more on this topic in Chuck’s latest interview on Straight Talk! with Jeff Cross
