There’s a moment in every successful professional’s journey when they look up from the path they’ve mastered and realize the uncomfortable truth: the very habits, mindsets, and playbooks that got them here won’t take them where they want to go next. Times change, and so should our habits, mindsets and playbooks.
That moment isn’t a sign of failure, but rather a sign of growth. It’s the inflection point between competence and evolution, between leading by what you know and leading by what you’re willing to learn.
1. Success Creates Blind Spots
When things are going well, we tend to double down on what’s worked. The sales leader keeps pitching the same way. The entrepreneur keeps managing every detail. The executive relies on old instincts. But as markets, teams, and expectations evolve, yesterday’s strengths can become tomorrow’s constraints.
A playbook that once produced efficiency can now produce stagnation. The leader who once thrived on control now needs to empower others. The founder who once excelled in execution now must think in systems and scale, often leading to bringing on capital and technology partners, and relinquishing control.
2. Redefine Your Next Destination
Before you can figure out what will get you there, you have to get clear on where “there” is.
- What’s the next level of impact you want to have?
- What kind of leader do you need to become to reach it?
- What will success look and feel like when you arrive?
Clarity here is crucial. Too many professionals chase “more, " more revenue, more responsibility, more recognition, without defining the deeper “why” behind it. Growth without purpose quickly becomes exhaustion disguised as ambition.
3. Upgrade The Way You Operate
You don’t need to throw away your entire skill set, you just need to evolve how you use it.
Ask yourself:
- What beliefs or habits have outlived their usefulness?
- Where am I playing defense when I should be innovating?
- What new skills or perspectives must I intentionally acquire?
This is where coaching, peer networks, and cross-industry exposure become invaluable. Fresh input fuels transformation. As Marshall Goldsmith famously wrote, “What got you here won’t get you there.” That phrase is not an indictment of the past, it’s an invitation to retool for the future.
4. Reframe Discomfort as Data
When you start stretching into new terrain, you’ll feel it, uncertainty, awkwardness, even frustration. Instead of resisting it, embrace it. Discomfort is simply feedback that you’re entering territory where learning can thrive.
If you’re feeling uneasy, it probably means you’re growing.
5. Lead With Curiosity, Not Certainty
Leaders who thrive in transition periods share one trait above all: curiosity. They ask better questions than they give answers. They test assumptions, seek perspective, and listen deeply.
Curiosity keeps you agile, and agility is the new currency of leadership.
The Bottom Line
The strategies that brought you success were perfect for a version of you that often no longer exists. The next chapter of your career, business, or leadership journey may require reinvention, not because what you’ve done is wrong, but because evolution is the cost of success.
So when you find yourself asking, “What got me here won’t get me where I want to go next. Now what?," start by acknowledging the courage it takes to ask that question. Then take the next step forward with humility, curiosity, and a willingness to grow. Because the answer isn’t in what you already know. It’s in who you’re becoming/adapting to be.
About the Florida CFO Group
As a fractional CFOs, The Florida CFO Group works with small and mid-sized businesses to design capital strategies, navigate lender relationships, and ensure financial stability. Whether you’re considering your first loan or refinancing existing debt, we help you make confident, data-driven decisions.
About the Author
Wayne Kalishis an experienced advisor to small and mid-sized, owner-managed businesses, specializing in organizational growth, M&A strategy, and financial consulting. He works closely with companies that have reached a growth plateau, quickly assessing operational structure, leadership alignment, and financial positioning to identify what’s needed to reignite sustainable momentum.
With a clear, strategic approach, Wayne helps business owners strengthen performance and prepare for their next chapter, often guiding them through successful sales to private equity firms or strategic buyers.
Contact Us
If you have any questions or would like to discuss your organization’s finance and strategic management needs, please call the Florida CFO Group at 1-877-352-2367 or send us a message. We are here to help you navigate your financial challenges and achieve success!