Ugh! Where Do I Even Start?

Ugh! Where Do I Even Start?

Problems come in all shapes and sizes, and small business owners are no exception when it comes to having them. Some problems are easy to fix: you've seen them before, you know what works, and you're off to the races. But those aren't the ones we're talking about today.

Today’s post is about those problems...the ones you keep kicking down the road. The ones that make you say, “Ugh! Where do I even start?”

When You’re Stuck in the “Ugh” Zone

There’s a framework I’ve leaned on throughout my experience in project management and Agile workspaces called the Cynefin Framework. It’s a sense-making tool designed to help you categorize and respond to different types of situations. Here’s a quick breakdown of the five domains:

1. Obvious (Simple)

• Cause and effect are clear.

• Best practices can be applied.

• Easy decisions...because you’ve seen this before.

2. Complicated

• There are multiple right answers.

• Requires expertise and analysis.

• It might take longer, but the path is findable.

3. Chaotic

• No time to analyze. Action is immediate.

• Think emergency response: EMTs, firefighters, military.

• You’re acting fast with what you know works in high-pressure moments.

4. Disorder

• Total confusion.

• You don’t yet know what kind of problem you’re dealing with.

• The first step is figuring that out.

5. Complex (Our Star Today)

• You haven’t dealt with this before.

• The path forward isn’t linear.

• You move ahead step by step, staying flexible and responsive along the way.

This is the “Ugh!” zone. The one that makes you pause, procrastinate, or freeze entirely.

Why It’s Worth Naming the Problem

Is it silly to spend time figuring out what kind of problem you have before you try to fix it?

Maybe it feels that way. But rushing in with the wrong strategy is often what leads to solving the same problem over and over again. And that’s just exhausting, for you and your team.

Let’s look at some common (but ineffective) coping strategies:

🚫 Quick-Fix Culture: Why It Doesn’t Work

• Butter Knife Brainstorm – Using the wrong tool just because it’s handy.

• The Duct Tape Diagnosis – Jumping to conclusions without understanding the real issue.

• Paint Over the Rust – Surface-level fixes that ignore deeper issues.

• Bubblegum Engineering – Temporary solutions that lack staying power.

These all share a common theme: action without intention. They feel good in the short term, but often lead you right back to the same spot, sometimes with more damage.

Worse still? If your team’s involved, these poor fixes can break trust, erode confidence, and lead to resentment or apathy. That’s a steep cost for a shortcut.

⚠️ The Other Extreme: Overthinking It

Then there’s the opposite end of the spectrum, over-engineering a solution in pursuit of perfection.

• Sledgehammer Logic – Smashing a nuanced issue with an aggressive fix.

• Parachute for a Speed Bump – Going overboard on minor issues.

• Lost in the Maze – Turning a straight path into a labyrinth.

• GPS in a Straight Line – Using fancy tools when common sense would’ve worked.

Both extremes, rushing in or over-preparing, are symptoms of the same problem: not fully understanding what you’re dealing with.

The Path Forward: Progress Over Panic

I write about this because I’ve been there. I’ve stared down the kind of tangled, frustrating problems that feel too big to tackle. And I’ve helped teams work through those “Ugh” moments using sense-making tools like Cynefin to get unstuck and start moving forward; intentionally, sustainably, and confidently.

So… Where Do You Start?

You start by recognizing the type of problem you’re dealing with so you can bring the right tools to the table.

If you’re tired of kicking the same can down the road, let’s talk. I help business owners and teams make sense of complex problems, build smart solutions, and actually move forward.

👉 Ready to stop spinning your wheels? Let’s connect! Because your business deserves better than band aids.