The messy middle: Why most business owners get stuck (and why we love helping with it)

This weekend, while writing another blog, I found myself describing something as "the messy middle". It wasn't a phrase I'd sat down and deliberately created. In fact, I don't think I'd even used it before. But the more I thought about it afterwards, the more I realised it's probably the thing Matt and I spend most of our time helping people with.

The messy middle is where most business owners live. It's the space between having an idea and having a plan. The space between knowing something needs to change and knowing what to do about it. The space between where you are now and where you'd like to be.

It's also the place where things can feel overwhelming. Not because you're failing. Not because you're doing anything wrong. But because running a business is complicated.

Most people don't arrive at our meet-ups, strategy sessions or bootcamps with one neat, clearly defined problem. Nobody turns up and says, "I've carefully analysed my business and identified exactly three things that need fixing."

Instead, they arrive saying things like:

"I've got loads of ideas but don't know where to start."

"I feel like I should be doing more marketing."

"I know something isn't working but I can't work out what."

"I'm really busy but I'm not sure I'm focusing on the right things."

Or, "I don't really know what I need. I just know something needs to change."

That's the messy middle.

It's the point where you've outgrown where you are now, but you haven't quite worked out what comes next. If I’m honest, I think it's where most small business owners spend far more time than they'd like to admit.

Why the messy middle feels so difficult

The reason the messy middle feels so uncomfortable is because it doesn't come with obvious answers. When a website breaks, you know you need to fix the website. When a supplier lets you down, you know you need a new supplier. When your van breaks down, you know you need to repair the van. Business growth doesn't work like that.

The challenges are often less obvious. You might have ten different opportunities in front of you but only have the capacity to pursue one. You might be doing lots of marketing but have no idea which bits are actually working. You might know your business has huge potential but feel completely overwhelmed by the number of directions you could take it.

The messy middle is often a clarity problem rather than a capability problem.

Most business owners already have the skills, knowledge and experience they need. What they don't always have is the space to step back and look at everything objectively. That's usually where we come in.

Why we love the messy middle

I appreciate this might make us sound slightly strange, but we genuinely love this stage of business. Partly because it's where the most exciting opportunities often sit, but mostly because it's where you see the biggest transformations happen.

There is something incredibly satisfying about watching somebody arrive feeling overwhelmed, frustrated or stuck and then gradually seeing everything start to make sense.

Sometimes the solution is surprisingly simple. Sometimes the answer is stopping something rather than starting something. Sometimes it's realising you've been solving the wrong problem entirely. And sometimes it's simply having somebody ask a question you hadn't thought to ask yourself.

The reason Matt and I work so well together is that we approach the messy middle from different directions. I'll often spot opportunities. Matt will often spot patterns. I'll start joining dots. Matt will start asking questions. Somewhere in the middle of those conversations, things usually become much clearer.

How our meet-ups help

Our monthly meet-ups are often where people first start untangling the messy middle.

People usually come because they want to learn something from the workshop. They see a topic they like the look of, book a free place and arrive expecting to learn something new. What surprises them is how valuable the conversations can be.

Sometimes all it takes is hearing how another business owner solved a similar problem. Sometimes it's having a conversation over coffee with somebody who asks a question you've never considered before. Sometimes it's simply realising you're not the only person feeling stuck.

The workshops give people something useful to think about. The conversations afterwards often help them work out what it means for their business. That's why we love running them.

How the bootcamp helps

Our One-Day Marketing Bootcamp is probably the most structured way we help people through the messy middle. Most people arrive thinking they need help with marketing. By lunchtime they've usually realised they actually need clarity. Marketing just happened to be where the symptoms were showing up. Sometimes the issue is audience. Sometimes it's messaging. Sometimes it's priorities. Sometimes they've been trying to solve entirely the wrong problem.

The day gives people permission to step away from the day-to-day running of their business and look at the bigger picture. We work through audiences, marketing funnels, opportunities, priorities and all the things that often get pushed to the bottom of the to-do list when you're busy keeping the business running.

By the end of the day, people leave with a plan. Not because we've told them what to do. Because they've finally had the space to work out what matters.

How half-day strategy sessions help

If the meet-ups help people start thinking differently and the bootcamp helps them create a plan, our half-day strategy sessions are where we really roll our sleeves up and get stuck into the messy middle.

Nobody arrives with a tidy challenge. They arrive with all the things swirling around their head. The opportunities. The frustrations. The ideas. The questions. The things they've been putting off. The things they're worried about. The things they're excited about. And together we start untangling them.

Sometimes we discover the problem isn't actually the problem. Sometimes we uncover opportunities they hadn't spotted. Sometimes we create a plan. Sometimes we create breathing space.

The outcome is different every time because every business is different. The goal is always the same though. Clarity.

Perhaps we're all in the messy middle

The funny thing is that I don't think the messy middle ever completely goes away. Every time your business grows, changes direction or enters a new stage, you find yourself back there again. The questions change. The opportunities change. The challenges change. But the feeling is often remarkably similar.

Which is probably why Matt and I spend so much time helping people through it. Not because we have all the answers. But because we've spent years helping people ask better questions.

Most of the time, people don't actually need somebody to tell them what to do. They need space to think, a bit of perspective and somebody to help them work out what matters most.

Whether that happens at a meet-up, during a half-day strategy session or halfway through a bootcamp doesn't really matter.

The important bit is that things start making sense again. And from what I've seen over the years, that's usually when the interesting stuff happens.