I walked past three “For Lease” signs on my morning route last week. All three were businesses I’d watched open with such promise—the bakery with lines around the block on opening day, the boutique fitness studio that couldn’t keep up with demand, the specialty coffee shop where the owner knew everyone’s name.
Each lasted about three years.
The pattern is so predictable it’s almost cruel. Year one: excitement and endless energy. Year two: the grind sets in but determination pushes them through. Year three: something breaks. Not the business model, not the cash flow—something inside the owner themselves.
During my negotiating days, I watched this same pattern play out with business owners. The ones who survived past year three weren’t necessarily the ones with better business plans or deeper pockets. They were the ones who’d had a particular conversation—usually forced upon them by circumstances—that most owners actively avoid.
The conversation that changes everything
Here’s what that conversation sounds like: “I can’t do everything myself anymore, and that’s not a failure—it’s growth.”
Sounds simple, doesn’t it? But for most small business owners, those words feel like admitting defeat. They started their business to be independent, to prove they could build something from nothing. Asking for help, delegating real responsibility, admitting they need others—it feels like betraying the very reason they started.
I remember sitting across from a restaurant owner who’d built a local empire of three locations. Smart guy, worked eighteen-hour days, knew every detail of his operation. When I suggested he needed to promote his assistant manager to handle daily operations, his face went pale. “But I AM the business,” he said. That was two years ago. Last month, I saw the “Thank you for 12 great years” sign in his window.
The research backs this up. A study published in Burnout Research found that job stressors can lead to burnout in small and medium-sized enterprise owner-managers, with occupational loneliness serving as a mediating factor. Think about that—it’s not just the stress, it’s the isolation that comes from believing you have to carry it all alone.
Why delegation feels like losing control
Most small business owners equate delegation with two things: expense and risk. They think, “Why pay someone to do what I can do for free?” Or worse, “They won’t do it as well as I would.”
But here’s what they’re really saying: “My identity is so wrapped up in being needed that I can’t imagine the business succeeding without my constant involvement.”
I spent years in rooms where executives insisted they were making rational business decisions while their real motivations were about maintaining status and control. Small business owners do the same thing, just with higher personal stakes. They’re not just managing a business; they’re managing their sense of self.
The owner of that bakery I mentioned? I knew her peripherally through community events. She’d arrive at 4 AM to prep, stay until closing to ensure quality, handle all the ordering, manage social media between customers. When someone suggested hiring a morning prep cook, she’d say she couldn’t afford it. But she could afford to lose Sundays with her family? She could afford the herniated disc from constant standing? She could afford the growing resentment that leaked into every interaction?
The real cost of doing it all
Eric Skicki, owner of My Square One Condo, put it perfectly: “Entrepreneurs are working literally 24 hours a day if not physically at least mentally, for several years, with little to no breaks.”
That mental load is what kills businesses. Not the physical exhaustion—though that’s real—but the mental weight of carrying every decision, every problem, every possibility in your head constantly. Your brain never gets to rest, recover, or gain perspective.
I learned this lesson the hard way in my career. For years, I prided myself on being the person who could handle any negotiation, who never needed backup, who had all the answers. It took a mild heart event at 58 to make me realize that my refusal to truly delegate wasn’t strength—it was fear dressed up as competence.
Small business owners live in this space constantly. They confuse being irreplaceable with being valuable. They think if the business can run without them, it means they’ve somehow failed or become unnecessary. The opposite is true. A business that requires your constant presence isn’t a business—it’s a job with terrible hours and an unreasonable boss.
How to start the conversation you’ve been avoiding
So how do you begin this conversation with yourself? Start by answering this question honestly: What would happen to your business if you got sick for two weeks? Not a day or two—two full weeks.
If your answer involves the business failing or significant damage, you don’t have a business—you have a dependency. And dependencies always end badly.
The next step is harder: identify the three things you do that genuinely require your unique skills versus the twenty things you do because you always have. Most owners discover they’re spending 80% of their time on tasks someone else could handle competently, leaving no energy for the strategic thinking and relationship building that actually grows businesses.
Here’s the thing about delegation—it’s not about finding someone who does things exactly like you. It’s about finding someone who does things well enough while freeing you to do what only you can do. The bakery owner who finally hired that prep cook? She discovered that while the croissants were shaped slightly differently, having energy to experiment with new recipes and actually talk to customers transformed her business.
The identity shift nobody talks about
The hardest part isn’t the practical aspect of delegation. It’s the identity shift required. You have to evolve from being the person who does everything to being the person who ensures everything gets done. That’s a fundamental change in how you see yourself.
In my negotiation days, the most successful executives were the ones who understood their real job wasn’t to have all the answers but to create conditions where the right answers emerged. They built systems, developed people, and—this is crucial—they stepped back enough to see the bigger picture.
Small business owners resist this because it feels like abandoning their baby. But refusing to let your business grow beyond your personal capacity is the real abandonment. You’re abandoning its potential, your own growth, and often your personal relationships and health in the process.
Closing thoughts
The conversation most small business owners refuse to have isn’t really about delegation or systems or hiring. It’s about identity, control, and the fear of discovering that maybe, just maybe, some parts of the business can thrive without their constant touch.
Year three is when this conversation becomes unavoidable. The adrenaline of startup has worn off, the accumulated exhaustion is real, and the gap between what the business needs and what one person can provide becomes undeniable. Those who have the conversation—however reluctantly—tend to make it to year five, year ten, and beyond. Those who don’t become another “For Lease” sign.
The ironic truth I learned after decades of watching power dynamics play out: the people who hold on tightest to control are usually the ones who lose it fastest. The ones who learn to let go, who trust others, who build something bigger than their own capacity—they’re the ones who end up with businesses worth having and lives worth living.
Your business shouldn’t need you every minute. If it does, you haven’t built a business. You’ve built a prison where you’re both the guard and the inmate. And that conversation you’re avoiding? It’s not about admitting weakness. It’s about finally claiming the freedom you started this business to find.
