Befriending the “How” Monster

There is a monster that lives under the bed.

Its name is How.

It isn’t a scary monster with claws, fangs, or anything out of a horror story.

Instead, it’s a muttering, ever-changing creature that whispers worries about how things will work out, especially late at night.

How will you do it?

How will you get there?

How will you make it work?

If you’ve ever been a kid who really needed to use the bathroom in the middle of the night, you already get how the How Monster works.

You’re perched on the bed.

You know exactly what you want: to get from your bed to the bathroom.

Your goal is clear, and so is where you want to go.

But still, you don’t move.

Why?

Because under the bed lives the monster named How.

The Adult Version of the Bed

As adults, we don’t sit on literal beds, afraid to walk to the bathroom.

We find ourselves stuck, afraid to take steps toward our dreams.

We want to build a life we love—maybe write a book, get a new job, find a relationship, or start a business. But as soon as we think about the steps, the How Monster starts whispering.

How will you afford it?

How will you make it happen?

How will you not fail?

So we stay perched.

Thinking. Planning. Delaying.

We’re full of potential, but still not willing to move.

The Turning Point

Now imagine the child on the bed doing something radical.

Instead of being afraid of the monster, they talk to it.

“Hey How… can you help me instead?”

The monster blinks, tilting its head in surprise.

No one has ever asked that before.

It thought its job was to scare, to warn, to complicate.

But it turns out the How Monster is a shape-shifter.

When feared, it becomes a shadow.

When befriended, it becomes a tool.

One night, it turns into a skateboard.

Another night, a magic carpet.

Another night, a brave pair of boots with night-lights on the soles.

Same monster. Different relationship.

What If “How” Isn’t the Enemy?

Here’s the coaching truth hidden inside the story:

The problem is not that you don’t know how.

The problem is that you think you must know how before you begin.

But “how” is not a prerequisite.

It is a collaborator.

The How Monster does not reveal its helpful forms while you’re frozen on the bed.

It reveals them as you move. 

You step off the mattress.

It becomes a flashlight.

You take another step.

It becomes a map.

You keep going.

It becomes momentum.

The Reframe

Fear says:

“Figure out the how, then go.”

Possibility says:

“Go… and the how will shape-shift to meet you.”

This is why so many brilliant, creative, capable adults stay stuck.

They are negotiating with the monster instead of walking with it.

They are demanding certainty from a creature whose superpower is improvisation.

Turning “How” Into a Guide

What if, instead of asking,

“How will I do this perfectly?”

You asked,

“How might this monster help me take one step tonight?”

Not the whole journey.

Not the full blueprint.

Just the next glide across the hallway.

Because the child who waits for the monster to disappear will stay on the bed all night.

The child who befriends the monster makes it to the bathroom and back, and eventually starts to wonder where else this shape-shifter could take them.

Your Turn

Where in your life are you perched on the bed, waiting for the How Monster to calm down?

What if its whispering isn’t a stop sign… but a request to be included?

Tonight, instead of trying to silence “How,” try inviting it:

“Okay, How… if you were here to help, what could you turn into for me right now?”

Then take one step.

Let the monster transform after you move.

A Final Note

This is the heart of coaching.

You don’t hire a coach because they hand you a perfect “how.”

You partner with a coach so you don’t stay frozen in bed, negotiating with fear.

In coaching, we walk with the How Monster together.

We test the steps.

We let the plan evolve in motion.

We turn whispers of doubt into shape-shifting strategies that actually fit your life, your values, and your creative style.

If you’re ready to stop over-planning from the mattress and start moving with support, that’s the work we do.

Take one step.

Invite the monster to play with you.

If you want someone by your side as it changes, you know where to find me.  

www.imagineandfulfill.com.