The Adventures of Lee The SME Owner

Lee sat in his office, staring out at the workshop yard below. The machinery hummed, and the steady rhythm of his team’s work filled the air, but his thoughts were elsewhere—wrapped around the question that had been nagging at him for months: What next?

The business was solid. It was profitable, stable, and had a good reputation. But Lee was tired, and he could feel the weight of every year he’d spent here. He loved the work—he always had—but the long days and endless responsibilities were wearing him down. Julie’s quiet suggestion had planted a seed in his mind: Was it time to step back? To find a way out? The thought was equal parts terrifying and intriguing.

He rubbed his temples and leaned back in his chair. There were a few options—none of them simple. Each one came with its own challenges, and none felt like a perfect fit. But he had to start thinking seriously about it. He couldn’t keep going at this pace forever.

His first thought, naturally, went to Glenn. He’d once imagined that his son would take over the business, continuing the legacy his own father had started. It seemed like the logical thing, the right thing to do—pass it down to the next generation. But Glenn… Glenn wasn’t ready. And that was putting it lightly.

Could Glenn get up to speed? That was the question Lee kept asking himself, but the answer never seemed clear. Sure, Glenn had the potential—he was smart enough, he understood the basics of the business, and he had a way of connecting with people when he wanted to. But that was the problem: Glenn rarely wanted to. He drifted from job to job, his personal life in shambles, and every time Lee had tried to bring him in, they’d ended up clashing.

Lee sighed. If only he could get his act together. Maybe, with the right guidance, Glenn could grow into the role. But how much time would that take? Could the business afford to wait? Could he afford to wait, emotionally or financially? And there was always the risk that Glenn might never step up, no matter how hard Lee pushed. The thought of handing the business over to Glenn in its current state felt like setting it up for failure.

Then there was the other extreme option: selling up and being done with it. Lee had run the numbers before—if he sold now, the business would fetch a decent price. He could walk away, debt-free, with enough to enjoy life without the constant stress. He could spend more time with Julie, with the grandkids. He could even travel—something he’d barely done since taking over the firm. The idea was tempting. Really tempting.

But there was a heaviness to it. Selling meant letting go of everything he’d built, the business he’d poured his heart into for the past three decades. It wasn’t just a company—it was part of his identity. And who would take over? Would they treat the team with the same respect he did? Would they care about the clients and the reputation of the business, or would they just strip it down for profit? The thought made his stomach churn.

He leaned forward, resting his head in his hands. There had to be a middle ground, right? Something between walking away completely and staying stuck in the daily grind.

What about taking on a financial partner? Someone younger, with fresh ideas, more energy. Someone who could take on some of the load and bring in new opportunities. He’d still have a hand in the business, but he wouldn’t be shouldering all the responsibility. It sounded reasonable, but Lee had his reservations.

Bringing in a partner meant giving up some control. He wasn’t sure how he felt about that. He’d been the sole decision-maker for so long, trusting someone else to have a say in how the company was run didn’t sit well with him. And what if they didn’t get along? What if they had different visions for the future of the business? The last thing he needed was to bring in someone who would take the company in a direction he didn’t agree with.

Then, of course, there was the team. His team. He’d handpicked and trained each of them. They knew the business inside and out, and for the most part, they were loyal, hardworking people. Troy, in particular, had stepped up in recent years—he had a good head on his shoulders, and Lee trusted him. But was the team ready—or even willing—to take on more responsibility? And if they were, would it be fair to push it on them?

He thought about the younger staff, how capable they were, how they handled day-to-day challenges without needing his constant oversight. There was potential there, for sure. But running a business wasn’t just about handling the work—it was about strategy, vision, and the endless pressures that came with being at the top. Could they handle all that without him?

He drummed his fingers on the desk. One option, of course, was to step back gradually—hand over more responsibility to the team and see how they managed without him breathing down their necks. He could take on a more advisory role, pop in a few days a week, and spend the rest of his time with family or pursuing other interests. It was tempting, but again, there were risks. If things went wrong, he’d be pulled back in. And would they even want the extra load? Some might be happy to step up, but others… maybe not.

Lee rubbed his eyes, feeling the weight of all the decisions he had to make. It wasn’t just about him—it was about the business, his team, his family, and the legacy his father had left behind. Every option felt loaded with complications, with unknowns. And yet, he couldn’t keep ignoring it. Something had to change, one way or another.

Could Glenn be the answer? If not, could the business survive without me if I sold it? If he didn’t sell, could a partner take enough of the load to keep it running without my constant oversight? And if neither of those worked, could the team carry the weight?

The questions buzzed in his head, no clear answers in sight. But one thing was certain—he couldn’t keep going as he had been. He needed a change. And soon.

For now, though, he pushed the thoughts aside. He had a business to run, at least for today. But in the back of his mind, the questions lingered, waiting for answers that wouldn’t come easily.

As he stood up and grabbed his jacket, preparing to head out onto the shop floor, Lee knew he had a lot to think about. But for the first time, he was ready to start exploring those options—one step at a time.

If you, or someone you know finds this story eerily familiar, how about we have a chat about what to do next? Conversation is free, right? [email protected] +64 275 665 682