WHEN SUCCESS CREATES A NEW DILEMMA, PART I
The dilemmas successful owners face are not signs of failure. They are natural byproducts of building a well-run business. The very systems, structures, and teams that once required constant oversight now free the owner from daily demands. The challenge for the owner now becomes redefining their value and purpose. By stepping into the role of mentor and focusing on leadership development while ensuring the business stays on course, owners can continue to contribute meaningfully without undermining what they worked so hard to create.
At this stage, owners must begin asking different questions, both about themselves and their business.
How well are they developing their team?
Small businesses grow at the pace their people grow. Are employees developing to the point where they challenge leadership, push it forward, and hold it accountable? If not, perhaps they’re in the wrong seat, or leadership hasn’t invested enough in their growth.
How are they developing themselves?
Are owners still stretched and challenged by their work, or have they slipped into familiar tasks that no longer push their thinking? Comfort may feel good, but it limits both personal growth and the company’s.
How are they managing their need for control?
Founders often have controlling personalities. While this is a strength early on, it becomes a barrier as the company grows. Like Zen archers who believe the bow, arrow, and archer act as one, business leaders must let go of the illusion of control. When they release the need to manage every outcome, they can focus on alignment, process, and culture. The results will follow.
Would they pay an executive salary for the work they’re doing?
If the answer is no, it may be time to let go of those tasks. Owners in this season often find themselves in a kind of quiet transition, still at the helm but steering differently. The problems they once solved directly now require a new kind of influence: not intervention, but intention. It’s less about fixing and more about fostering.
Redefining Value and Purpose
In the early years, a small business owner’s value often came from doing the work and keeping the business alive day to day. As the company grows, the role shifts from doing, to managing, to leading, to mentoring. This progression not only sustains the business but also models the same growth path for future leaders. It also sends a message to the team: growth doesn’t stop when the business stabilizes. In fact, that’s often when the deeper work begins.
Success at this level doesn’t mean stepping aside. It means stepping up to a different kind of leadership, one rooted in developing others, redefining value, and shaping the company’s future. In the end, leadership is less about holding on and more about lifting up. That’s the challenge—and the opportunity—of success.
