If you’ve been following along this month, you’ve heard me talk a lot about planning.

And I get it…

At some point it can start to sound like the teacher from Charlie Brown:

“Wah wah wah wah wah wah… planning, planning, planning…”

But stick with me, because this one matters.

Because today I want to show you what planning actually does in real life.

The “Big Rocks” Reality:

You’ve probably heard the analogy:

You fill a jar with:

• Big rocks first (the most important things),
• Then smaller rocks
• Then pebbles
• Then sand.

If you don’t start with the big rocks…

Nothing else fits.

That’s exactly how I approach my calendar.

And this past week gave me some perfect real-life examples of why it works.

Planning creates space for the unexpected 

Let’s start with the “sand.”

The unexpected things.

Like:

• A flat tire

• A car issue that needs fixing

• Extra errands that suddenly show up

These things happen.

They always will.

But when your calendar isn’t already overloaded…

You can handle them without everything falling apart.

Planning Creates Space for the FUN Stuff Too

Now here's the part most people don’t expect.

It doesn’t just make room for problems… it makes room for joy.

This week, I booked flights for my October trip to Italy.

That’s one of my “big rocks.”

Now that it’s in place, I’ve created space for:

• Wandering through Milan
• Exploring other cities
• Letting the trip unfold naturally.

If I had waited until the last minute?

All my time and energy would’ve gone into just getting there.

 And I would’ve missed the opportunity to enjoy everything around it.

The Magic of Knowing Your Calendar

Here’s another example.

I heard on the radio that a group of 80s bands I love is coming to Boston this summer.

And because I already knew my schedule…

I didn’t hesitate.

I booked the tickets.

Now I have something fun to look forward to months in advance.

That’s what planning does.

It gives you the confidence to say yes to life.

Let’s Be Honest… There’s Always Drudgery

Even when you love what you do…

There are still things you don’t love.

For me?

• Updating financial records

• Cleaning my office

• Administrative tasks

That’s part of life. Part of business.

But here’s how I manage it:

👉 I balance it with things I’m excited about

Because when you have something to look forward to…

The hard stuff feels lighter.

Planning Isn’t About Control

It's not about packing your calendar so tightly there’s no room to breathe.

It's the opposite.

Planning:

• Creates structure

• Protects your priorities

• Leaves room for spontaneity

It's what allows you to handle the unexpected and say yes to the exciting things.

The Real Benefit

When you plan intentionally:

✔️ You reduce stress
✔️ You create flexibility
✔️ You make room for joy
✔️ You stop living reactively

And you start living on purpose.

So if planning has felt restrictive to you before…

I invite you to look at it differently.

Because done right—

It’s the thing that gives you the most freedom.

As always, what I hope for you is that you live a life you love without giving up the things that bring you joy.