The Owner's Trap: Are You Where You Want to Be as a Business Owner?

Your 2025 numbers are in. 

Revenue. Profit. Cash flow. Maybe they look strong. Maybe they’re steady. Maybe they’re not where you hoped.

But before you dive into another year of pushing harder, chasing growth, or fixing what feels off, pause and ask a different question:

Are you where you want to be as a business owner?

Not just financially.

But in your time.

In your energy.

In your clarity about the future.

In the life you’re building today.

Because this is where many business owners find themselves quietly stuck, in what we call “The Owner’s Trap.”

What The Owner's Trap Looks Like 

From the outside, things may look fine. The company is running. Customers are being served. Payroll is met.  The business may even be growing.

But internally, it feels different.

You feel like the glue. If you stop, everything falls apart.

You struggle to find the right people to truly take things off your plate.

You’re exhausted from working in the business every day.

You’re working hard, but the money still feels tight.

You’re not sure what your business is worth, or if you could walk away.

You want out someday, but you have no clear plan, and that uncertainty is unsettling.

This isn’t a revenue problem. It’s an ownership design problem. And it’s incredibly common.

👉 Sure Controls Case Study: Terry Brei went from being consumed IN the business to working ON the business and achieved $4M+ increase in Business Value in 3 years.

What Business Owners Actually Want 

When we talk candidly with business owners, what they want is rarely just “more revenue.”

Business owners want:

• RELIEF - from carrying it all alone.

• FREEDOM BY CHOICE - to work because they want to, not because they have to.

• INDEPENDENCE - a business that thrives without them.

• CONTROL - to exit on their own terms.

• FAIR REWARD - to get paid what the company is truly worth.

• PURPOSE - to move toward something exciting, not just away from stress.

That’s not about numbers. It’s about the life they’re living now, and what they want for themselves in the future. 

And yet many owners postpone any conversation around exit or succession. They tell themselves, “I’ll deal with that when I’m ready to sell.”

What they don’t realize is that many of their goals can be achieved long before a sale is on the table.

Why the Typical "Escape Plan" Doesn't Work 

The traditional path out of The Owner’s Trap is fragmented and surface-level:

Financial planners focus on investments.

CPAs focus on taxes. 

Brokers focus on selling. 

Attorneys focus on structure.

All important. But rarely integrated. And planning often starts too late, when options are limited and time is no longer on your side.

Even more important, most owners don’t actually want to sell today.

What owners want is to reduce pressure now. Improve cash flow now. Gradually step back from the day to day. Build a company that can thrive without them.

This isn’t just exit planning. It’s ownership transformation.

Smarter Questions for 2026 

Instead of asking:

• How do we grow 10%?

• How do we improve margins?

• How do we hit our revenue target?

Ask yourself:

• If nothing changes, would I be happy owning this business three years from now?

• Would I still be the bottleneck? Still the chief firefighter? Still the primary decision-maker on everything? Still unsure what the business is worth?

• Or would I be leading strategically, empowered by data, supported by a capable leadership team, confident that I’ll have options when I'm ready to exit?

Building real business value as part of your exit strategy does more than increase a theoretical sale price.

It gives you better cash flow. Better leadership leverage. It creates clearer financial visibility. It builds strategic optionality to sell, scale, or stay.

From Operator to Owner: Designing a Transferable Business 

We’ve seen business owners transform when they intentionally redesign their role.

They hire and develop the right leaders. Install consistent financial reporting and budgeting so decisions are driven by data. Document and systematize operations. Empower others to own results. Create rhythms of accountability.

The result?

• Revenue grows.

• Profitability expands.

• Value increases.

• The owner can step away for weeks at a time while the business continues to perform.

But the real shift is personal. Their life changes.

They move from survival to intention. From constant reaction to focused leadership. From dependence to independence.

And when the time comes for a transition, whether through sale, internal transfer, or family succession, they are prepared.

The Real Risk to Your Personal and Business Exit Strategy

You may have heard the sobering statistic that only 20–30% of businesses that go to market actually sell.

But the bigger risk isn’t failing to sell.

It’s spending years spinning your wheels while nothing fundamentally changes.

It’s losing control of when and how you exit.

It’s settling for less value, fewer buyers, higher taxes. 

Or, staying trapped in a business that depends on you forever.

So... Are You Where You Want to Be?

As you look at your 2025 numbers, do more than evaluate revenue and profit.

Evaluate alignment.

• Does your business support the life you want today?

• Are you building something transferable?

• If you had to step away for 30 days, what would happen?

• Do you know your current value and what’s driving it?

• Are you intentionally creating options, or hoping they’ll appear later?

You don’t have to sell tomorrow. But you do need a plan. 

Because the goal isn’t just to grow revenue. It’s to build real value, create real options, and ultimately exit, or continue, on your terms.

That’s the difference between running a business… and truly owning one.

Let's Start the Conversation

Value Creation and Business Exit Strategy: Common Questions  

When should a business owner start building an exit strategy?  

Ideally, 3 to 5 years before a planned transition. If you are considering selling to a third party, transitioning to family, or structuring a management buyout, the most successful outcomes happen when value is intentionally built several years in advance. That time allows you to strengthen EBITDA, improve cash flow consistency, reduce owner dependency, install leadership depth, and clean up financial reporting.

For family transitions in particular, the timeline is often longer. Successors may need 5 or more years of leadership development, gradual responsibility transfer, and structured ownership transition planning to ensure both operational readiness and family alignment.

Why is building business value an important part of exit planning?  

Building business value focuses on strengthening the drivers that determine what your company is worth. These drivers include consistent EBITDA growth, strong gross margins, recurring or predictable revenue, documented systems, leadership depth, and reduced reliance on the owner. Together, these elements increase both valuation multiples and buyer confidence.

Gaps in leadership, inconsistent profitability, or unclear financials can quickly reduce deal terms or eliminate buyers altogether. When owners focus first on value creation, exit becomes one of several viable options, not a last-minute scramble. They gain leverage, flexibility in timing, and greater control over how and when they transition.

Can I build an exit strategy even if I don’t want to sell anytime soon?

Yes. In fact, that is often the best time to do it. Designing an exit strategy early allows you to reduce risk, improve profitability, strengthen leadership, and increase the overall value of the company. Even if you never sell, you benefit from improved cash flow, greater operational independence, and more personal flexibility. Exit strategy done well is really about creating options.

Why do so few businesses successfully sell?

Only a minority of businesses that go to market ultimately close a transaction. Common reasons include overreliance on the owner, inconsistent profitability, lack of clean financial reporting, limited leadership depth, and unrealistic expectations around value.

Buyers look for transferable cash flow, documented systems, and a leadership team that can operate without the founder. When those elements are weak, deals fall apart or valuations suffer.

How long does it take to build a transferable business?

There is no universal timeline, but meaningful change typically happens over several years. Strengthening leadership, installing financial discipline, improving margins, and reducing owner dependency are strategic initiatives that compound over time. The earlier an owner begins, the more control they retain over timing, valuation, and structure.

Book a conversation with our team to take the first step on your Value Journey. 

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Jayne McQuillan, CPA, MBA, Certified Exit Planning Advisor (CEPA) is the owner of Journey Consulting, LLC and author of The Value Journey: How to Drive Profits, Build Wealth, and Exit Your Business on Your Own Terms. 

Our firm is focused on providing business owners and their businesses with strategic planning, exit planning, financial expertise, and organizational improvement. We use a holistic approach within all of our services by aligning leadership with business strategy and outcomes.