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Monday Musings | Plant the Asparagus

May 04, 2026 6:30 AM | Rebecca Gallagher (Administrator)


Good morning!

I have a personal philosophy that’s been really top of mind lately… probably because it’s spring and I’m FINALLY doing something I’ve been putting off for years.

My advice?

“Plant the asparagus.” 

Stay with me…

Life (and STR ownership) is full of choices about where you spend your energy:

  • The must-do tasks with clear deadlines
  • The quick wins that give you an immediate result
  • And then… the big ideas—the ones you know will make a real difference, but no one’s noticing that you haven’t done them yet

Those are the ones that quietly get pushed to “next season.”
And then the next.
And then… well… years go by.

That’s asparagus for me.

I’ve always wanted to grow it. But it takes effort to plant it right… and then 3–4 years before you can harvest anything. When I owned the inn, I told myself, “Will I even be here in 4 years?”

Turns out… I was there for 15.

I should have planted the asparagus.

So let me ask you…

What’s the “asparagus” in your STR business?

  • The direct booking strategy you keep meaning to build
  • The landscaping upgrade that would transform your curb appeal
  • The systems that would save you hours every week
  • The brand refresh you know you’ve outgrown
  • The partnerships you’ve been meaning to develop

The things that won’t pay off tomorrow… but could completely change your business a year (or three) from now.

Here are five ways to finally get started—and actually follow through:

1. Name it.
Be specific. “Improve my business” isn’t it. “Launch a direct booking website by September” is.

2. Break it down.
Big ideas stall when they feel overwhelming. What’s step one? Just one.

3. Put it on the calendar.
If it’s not scheduled, it’s optional. And optional doesn’t get done.

4. Make it visible.
Tell someone. Share it with your team. Post it on your wall. Accountability changes everything.

5. Start messy.
It won’t be perfect—and that’s fine. Progress beats perfection every time.

Here’s the thing…

The best time to plant the asparagus was a few years ago.
The second-best time?

Right now.

So go ahead… plant it

—Rebecca

P.S. If you’re not sure what your asparagus should be—or you want a group of people who will actually hold you accountable—that’s exactly what we’re building inside the Poconos VRO. Come grow with us.


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