Entrepreneurship - Hospitality - Ideas

Be the Boss Who Still Shows Up at 3AM

It was 3AM in December when my phone rang. A smoke alarm had gone off in one of my units. No smoke, no fire—but the guests were scared. Outside, Boston was buried in snow. Still, I threw on a jacket and went.

Not to silence an alarm. To show up. To reassure. To calm an scared customer. To show that we are on top of everything.

And also—to make sure everything really was okay. Because when you’re the one running the business, you’re not just calming guests. You’re also protecting the thing you’ve built.

Sometimes, it’s about empathy.
Sometimes, it’s about liability.
Often, it’s both.

When Going the Extra Mile Is the Job

In my last post, I wrote about why we should obsess over feedback—not stars. That wasn’t about chasing approval. It was about listening carefully and responding intentionally.

This is the next layer: turning that insight into action. Because as the operator, you’re constantly deciding when to go the extra mile—and when to hold the line.

The goal isn’t to say yes to everything. It’s to serve in ways that truly matter—both for your guests and for the sustainability of your business.

Smart service isn’t reactive. It’s intentional.

Not Every Fire Needs to Be Put Out

Being a business operator means navigating dozens of small decisions every day. Some issues need your full attention. Others will resolve on their own.

The key isn’t how loud the complaint is—it’s what’s at stake.

Do I deliver a portable AC unit when it’s 55°F outside?
Do I apologize for the sound of footsteps in a hundred-year-old home?

Some requests are about comfort. Some are about expectations. But some, like that 3AM smoke alarm, are about safety, trust—and protecting both the guest and your liability.

The 3AM Rule (and When I Break It)

I rarely show up in the middle of the night. But that night, I did.

Not because it was convenient, but because it was the right call.

I needed to make sure the space was safe. I needed to visibly demonstrate that we cared. And, just as importantly, I needed to be sure I wasn’t exposing the business to unnecessary risk.

That one visit addressed guest anxiety, confirmed the alarm was a false one, ensured all systems were working, and gave me peace of mind. It likely prevented a refund—and earned several extra nights of booking.

But I don’t jump at every message.

When someone complains about the sound of cooking in a shared kitchen during dinner hours, I listen—but I don’t apologize. That’s part of the experience. And the price reflects it.

You don’t get a BMW experience on a Toyota budget. Still reliable. Still great value. Just not the same.

So I created a simple mental model to guide my choices:

Urgency × Impact × Loyalty Potential = Worth It

If the score is high across the board, I act.
If not, I pause.
That’s not neglect. That’s operating with intention.

Thoughtful Service Is Good Business

This isn’t a contradiction of what I wrote in Obsess Over Feedback, Not Stars. It’s a continuation.

Feedback is signal. Action is strategy.

You listen to everything. But you only act when the outcome justifies the effort—whether that means stronger guest loyalty, better reviews, reduced liability, or long-term trust.

Every decision passes through two filters:

  1. Will this help my revenue—through conversion, retention, reviews, or pricing power?

  2. Will this hurt my bottom line—through cost, liability, or time that doesn’t return value?

You don’t serve less.
You serve smarter.

And sometimes, smarter means showing up. Not just to fix the problem, but to take care of the people—and to protect the business.

A guest recently left this note:

“Thank you so much!! Everything was amazing. Thank you for going above and beyond. That was extremely appreciated.”

That’s the result of thoughtful choices—of showing up when it matters, and holding back when it doesn’t.

That’s how trust is built.
That’s how businesses grow.
That’s how you keep going—year after year, call after call.

Even at 3AM.

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