Toss Away the ‘Could Haves’ and ‘Should Haves’: A Day for Letting Go and Leading Forward

In the fast-paced world of hospitality — where every moment is about reacting, delivering, and moving forward — it’s easy to dwell on missed opportunities, past mistakes, or what could have been.

But today, on Toss Away the “Could Haves” and “Should Haves” Day, we’re invited to pause, reflect, and most importantly, release.

What Is This Day All About?

Celebrated on the third Saturday of July, this day was created to encourage people to:

Let go of regrets
Stop dwelling on missed chances
Forgive themselves
Start fresh — personally and professionally

It’s not about ignoring the past — it’s about learning from it and moving forward lighter.

Why It Resonates Deeply in Hospitality?

In hotels, restaurants, and resorts, we operate in high-pressure environments where:

A single bad review can spiral into anxiety
A poorly handled guest situation might haunt a team member
Business decisions not taken (“we should have launched that brunch!”) linger long after

But in this industry, we can’t afford to carry the weight of yesterday.
Every new guest is a chance to begin again.

What to Toss Today (And Every Day)?

Mental Clutter:

“I could have taken that better job…”
“We should have upgraded the kitchen last year…”
“I should have spoken up in the meeting…”

Emotional Baggage:

Guilt over past leadership decisions
Regret over promotions not pursued
Fear of repeating mistakes

Hospitality-Specific Examples:

That seasonal offer that flopped? Let it go.
That guest complaint you replay every night? Toss it.
That staff member you couldn’t retain? Learn and lead forward.

What to Keep Instead?

✅ The lesson
✅ The experience
✅ The clarity
✅ The drive to do better — not out of regret, but from renewed purpose

A Ritual Worth Starting

Many people celebrate this day by writing down their “could haves” and “should haves” on paper, then tearing or tossing them.

Imagine starting your day with your hotel team doing the same. It builds:

Emotional clarity
Team morale
Forward-focused energy

You can even make it a monthly ritual in your operations or leadership huddles.

Final Thoughts

In hospitality, just like in life, we’re not defined by the paths we didn’t take — but by how we walk the one we’re on now.

Let’s serve, lead, and live with presence, not regret.
Because the best of hospitality isn’t in the should haves — it’s in the right nows.

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