The Messy Middle Is Where Learning Happens

I’ve been watching two people in my life interact with technology lately: my sixty-something-year-old husband and my three-year-old granddaughter.

My granddaughter isn’t using technology independently. But technology is simply part of the environment around her.

She watches us FaceTime. She wants to hold the phone yet sometimes walks away. She loves to see the photos we’ve taken and knows how to scroll through them.

And, perhaps most importantly, she watches as the adults around her make all of this happen. She observes. She asks. She tries. She watches again.

My husband takes a somewhat different approach.

When something on his iPhone doesn’t work the way he expects, there’s a good chance the phone is the problem.

Something moved. Something changed. Something that worked yesterday no longer works today. And when he gets stuck, why spend ten minutes figuring it out when someone nearby already knows the answer?

From an efficiency standpoint, he may be right. But from a learning standpoint, maybe not.

That space between not knowing and figuring it out is what I think of as the messy middle of learning.

It’s the part where we observe, try, get stuck, adjust, and try again. My granddaughter seems perfectly comfortable there. As adults, we want a quicker way out.

When Efficiency Gets in the Way

As adults, and particularly as experienced professionals, we become very good at being efficient.

We know how to get things done. We know where to find answers. We know who to ask. We develop shortcuts based on years of experience. Those are strengths.

But efficiency and learning aren’t always good partners.

Learning something new often requires us to temporarily give up some of that efficiency. We have to tolerate not knowing, make an imperfect first attempt, search for an answer, try something that doesn’t work, and figure out why.

We need to enter the messy middle. And that can be uncomfortable and inefficient, at least in the short term.

We may interpret uncertainty as inability, frustration as poor fit, or slow progress as no progress at all. We may abandon something because we aren’t immediately good at it, or find the fastest route to an answer before we’ve had an opportunity to make sense of the problem ourselves.

When we move too quickly toward the answer, we may learn what to do without understanding why it works or seeing how it connects to something else. We solve today’s problem without necessarily becoming better prepared for tomorrow’s.

Three Before Me

A client once shared a practice she encouraged with her team: “Three before me.” Before coming to her for an answer, she encourages them to try three things first. I loved the simplicity of it.

It wasn’t about withholding help or expecting people to struggle unnecessarily. It was about creating enough space for someone to think before another person solved the problem for them.

Try something. Look for another resource. Observe what someone else has done. Use what you already know. Adjust based on what happened. Then ask for help.

Then, the conversation changes.

Instead of: “What should I do?” it becomes: “Here’s what I tried. Here’s what happened. Here’s where I’m stuck.”

That is a very different learning conversation.

How Do You Navigate the Messy Middle?

In the Design Your THRIVE Growth & Learning Pathway, I use five learning patterns to help people think about how they approach growth and development. They become particularly useful when learning gets messy.

Curiosity & Openness: Can I remain curious when I don’t know the answer? Instead of immediately deciding something won’t work, can I ask another question or consider another possibility?

Experimentation & Risk: Am I willing to try before I know exactly what will happen? Learning requires enough room to test ideas, make mistakes, and discover.

Effort & Follow Through: Can I stay with something after the initial enthusiasm disappears or when learning gets hard? Some things only become easier through repetition and practice.

Reflection & Adjustment: Am I paying attention to what my attempts are teaching me? Persistence doesn’t mean repeating the same approach indefinitely. Sometimes the next learning move is to adjust.

Learn With Others: Do I know when another perspective could help me move forward? Learning with others doesn’t mean handing over the problem. Feedback, observation, questions, coaching, and expertise can all help us see what we couldn’t see alone.

Together, these patterns help us do something more useful than simply telling ourselves to “keep trying.” They help us decide what kind of next move we need.

Try Again, Try Differently, or Bring Someone In?

Sometimes we simply need another attempt. Sometimes the approach, not our capability, is the problem. And sometimes we’ve reached the point where another person’s perspective will move our learning further than continuing alone, helping us move through the messy middle.

The messy middle is part of learning and learning agility helps us navigate these setbacks. Learning agility isn’t about knowing everything or figuring everything out independently. It’s being able to keep learning when you don’t already know what to do.

Which brings me back to my granddaughter.

She doesn’t know she’s practicing learning agility when she watches someone flip the screen during FaceTime.

She’s simply interested in what is happening. She watches. She wonders. She tries. She notices what happens. She watches someone else. And she’ll try again.

She’s not worried about being efficient. She’s trying to figure out how her world works.

Perhaps there is something worth reclaiming in that.

The next time you find yourself struggling with something new, resist the urge to escape the messy middle too quickly.

Stay curious a little longer. Try something. Notice what happens. Adjust. Bring someone else in when their perspective will help you learn, not simply to give you the answer.

And before deciding you’re stuck, ask yourself:

Do I need to try again, try differently, or bring someone in?

You may not be stuck at all. You may simply be learning.