GNT #127: On holiday!

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I was out on holiday for the month of July!

That’s bizarre to say… it feels very European of me.

But Ed, the kids, Luna pup, and I took off on an epic motorhome adventure sabbatical through the Pacific Northwest for the entire month.

This has been a dream trip for years, just hit the road as a family in the summer. One of those “someday” things we talked about while juggling life, work, school, and business.

Roadtripping is so different than flying, and I really like the slow travel vibe.

But the truth is: the trip didn’t happen by accident.

Like most things that feel impossible at first, they become possible when you take one important step:

You put it on the calendar.

If you're someone who keeps saying "someday" to the important things, today's newsletter is for you.

We’ll talk about:

• Why someday keeps slipping
• The simple planning move that makes hard things happen
• 4 prompts to protect space for what matters most

You’ll walk away with a simple way to finally make space for the stuff that matters.

Let’s dig in. 

Why “someday” rarely happens on its own

Most of us assume we’ll get to the meaningful stuff once work slows down.

But work rarely slows down on its own. 

It simply fills the available space on the calendar. New opportunities show up. The urgent always beats the important, unless you reverse it intentionally.

The calendar fills itself unless you fill it first.

That’s what made the difference for us this year.

The calendar move that made it happen

On December 30th, 2024, Ed and I stood in front of the empty Big Ass Calendar (thank you Jesse Itzler.)

I'd been following Jesse for a while and was intrigued by his annual planning method. (Hint: it includes clearing out clutter, handwritten letters, and clear steps to reflection)

While staring at that blank calendar, Ed asked the question that prompted this whole adventure.

"What if we just took off in July?"

That's the power of this calendar move. It forces you to design the year you actually want before everything else takes over.

So before any work. Before any events. Before any build projects.

We blocked it off:

1 month.
July 2025.
Protected.

And then everything else scheduled around it. It wasn’t easy. It took a lot of finagling. But if you don’t (1) give yourself the time to think about what you truly want and (2) actually prioritize it, you'll end up living in reaction mode to everything else that comes into your orbit.

This trip didn’t happen because we had the time.

We had the time because we scheduled it first.
 

4 moves to turn “someday” into scheduled

Most people wait for open space. Here’s how to create it:

1️⃣ Name your dream

Be brutally specific. Not, “I want more balance."

Think:

• I want to play House of the Rising Sun on piano

• Visit my extended family in Norway

• Swim 800m in 14 minutes
• Build a sauna retreat in my backyard

• Launch my new penguin board game idea

Vague goals never get scheduled.

2️⃣ Assign a placeholder deadline

 Before you have all the details ironed out...

• Pick a month, quarter, or season.

• Put it on the calendar now, even if it's still a sketch.

Deadlines force decisions. 

I once had a friend who signed up for a variety show just so she could learn how to play the guitar. Or my friend who signed up for a half-marathon as a forcing function to start running again.

3️⃣ Reverse-engineer your runway

Once it’s on paper, work backwards:

• What projects need to wrap first?
• What capacity do you need to free up?
• What new skills do you need to acquire?
• What client or team conversations need to happen early?
• Who is going to keep you accountable?

The earlier you plan, the fewer tradeoffs you’ll face later.

4️⃣ Make a micro-commitment today

Momentum can start small:

• Book one piece (the Airbnb, the swim membership, the class).\
• Block time on your calendar
• Email your team with the heads-up

Action beats intention every time.
 

Takeaway

"Someday" doesn't show up on its own.

If you want space for what matters, you have to claim it early.

✅ Schedule it before everything else fills the space.
✅ Reverse-engineer the plan to protect it.
✅ Start with one small commitment today.

The sooner you put it on the calendar, the sooner it becomes real. I'm glad our month-long Pacific Northwest sabbatical finally became a reality.

👉 What’s one "someday" you can move onto the calendar right now?

I’m always rooting for you. See you next week.

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If you liked this article, you might also like:

GNT #082: Early action or early planning?
GNT #103: I Like Big Plans and I Cannot Lie
GNT #094: Don’t Find Your Dream Job, Craft Your Dream Day

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