Why Am I More Overwhelmed Now Than When I Started My Company?
You built this company from nothing. You had the vision, took the risks, and pushed through every obstacle to get where you are today. Your team has grown from just you to 30, 50, maybe even 100+ people. Revenue is up, the market is responding, and by every external measure, you’re succeeding.
So why do you feel more overwhelmed, exhausted, and trapped than you did when you were working 80-hour weeks in your garage?
If you’re asking this question, you’re not alone—and you’re not failing. You’ve simply hit what I call the Leadership Complexity Wall.
The Hidden Cost of Growth
When you started your company, the challenges were clear and immediate. You needed customers, revenue, and a product that worked. The problems were right in front of you, and you could solve them directly. There was a beautiful simplicity to the chaos.
But as your company grew, something fundamental shifted. The challenges multiplied exponentially, but your capacity to handle them directly didn’t. Now you’re dealing with:
- People problems that don’t have clear solutions
- Systems that break under the weight of growth
- Decisions that affect dozens of people and thousands of customers
- Strategic questions with no obvious right answers
- Cultural issues you never saw coming
- Financial complexity that makes your head spin
You went from being a problem-solver to being a problem-receiver. Instead of having 5 clear problems to tackle, you now have 50 ambiguous challenges landing on your desk every day.
The Skills That Got You Here Won’t Get You There
Here’s the hard truth: you’re overwhelmed because you’re still trying to lead your 45-person company the same way you led your 5-person startup.
In the early days, your superpowers were:
- Direct action – you could fix things yourself
- Speed – you could make decisions instantly
- Control – you knew everything happening in the business
- Hustle – you could outwork any problem
These skills built your company. But now they’re killing you.
The leadership skills that create a company are different from the skills that scale a company. And the transition between these two phases—what I call moving from Quadrant 2 to Quadrant 3 leadership—is where most founders get stuck.
Why “Just Work Harder” Doesn’t Work Anymore
You’ve probably tried the obvious solutions:
- Working longer hours
- Hiring more people
- Implementing new systems
- Reading more leadership books
- Attending conferences and workshops
But here’s what happens: you work harder, but the overwhelm stays the same or gets worse. You hire more people, but now you have more people coming to you with problems. You implement systems, but they don’t seem to fit your culture or your style.
The reason these solutions don’t work is that they’re addressing symptoms, not the root cause.
The root cause is that you’re still operating as the Chief Everything Officer instead of the Chief Executive Officer.
The CEO Identity Shift
The transition from founder to true CEO requires a fundamental shift in how you see your role:
From: Being the person with all the answers
To: Being the person who develops people who have answers
From: Solving every problem yourself
To: Creating systems and culture where problems get solved without you
From: Being the hardest worker in the room
To: Being the person who creates conditions for others to do their best work
From: Controlling every outcome
To: Influencing outcomes through leadership and vision
From: Being indispensable
To: Making yourself strategically dispensable
This isn’t about working less—it’s about working on different things. Things that only you, as the CEO, can do.
What This Looks Like in Practice
When you make this shift successfully, several things happen:
Your team starts bringing you solutions, not just problems. Instead of “We have an issue with the Johnson account,” you hear “We had an issue with the Johnson account, here’s how we handled it, and here’s what we’re changing to prevent it next time.”
You have space to think strategically. You’re not constantly in reactive mode. You actually have time to work on the vision, the big partnerships, the future direction of the company.
You sleep better. The weight of every single operational decision isn’t on your shoulders anymore.
You remember why you started the company. You get back in touch with the vision and passion that drove you to build this thing in the first place.
The Path Forward
If you’re reading this and thinking “This sounds impossible” or “My team isn’t ready for this,” I hear you. This transition doesn’t happen overnight, and it doesn’t happen without intentional development of both your leadership skills and your team’s capabilities.
The leaders who make this transition successfully typically:
- Assess their current Leadership Style and learn how to adapt it for their team’s needs
- Get clear on their Leadership Journey stage and what specific skills they need to develop next
- Build coaching skills so they can develop their team instead of doing everything themselves
- Create systems and culture that support independent decision-making
- Get support from other leaders who’ve made this transition successfully
The overwhelm you’re feeling isn’t a character flaw—it’s a sign that you’re ready for the next level of leadership. The question is: are you ready to make the shift?
Are you a founder or CEO feeling stuck between doing everything yourself and trusting your team to step up? Take our Leadership Style Assessment to identify your current leadership approach and discover your next steps toward scaling yourself, not just your business.
