Toss Away the “Could Haves” and “Should Haves” Day (July 19th, 2025)

Quick facts
When is it?	July 20th, 2024 July 19th, 2025 July 18th, 2026 July 17th, 2027 July 15th, 2028
Tagged as:	Life & Living People & Relationships
What's the hashtag?	#TossAwaythe“CouldHaves”and“ShouldHaves”Day
We first published this page on:	Apr 17th, 2025
We last updated this page:	Apr 17th, 2025

Contents

Have you ever caught yourself replaying old decisions, thinking, “I should have done this” or “I could have done that”? Toss Away the “Could Haves” and “Should Haves” Day invites us to let go of these lingering regrets.

It’s a chance to stop dwelling on missed opportunities and focus on the present. By releasing these thoughts, we free ourselves to embrace life as it is now.

This day encourages a shift from self-blame to self-compassion, reminding us that the past can’t be changed, but our current actions can shape a better future.

Letting go of “could haves” and “should haves” isn’t about ignoring the past; it’s about not letting it control us. Regret can weigh us down, making it hard to move forward. By acknowledging and releasing these feelings, we make room for growth and happiness.

This day serves as a reminder that every moment is an opportunity to start anew. Embracing the present allows us to live more fully and authentically, free from the shadows of what might have been.

How to Celebrate Toss Away the “Could Haves” and “Should Haves” Day

Feeling weighed down by past regrets? Toss Away the “Could Haves” and “Should Haves” Day offers a chance to release those burdens. Here are some engaging ways to celebrate and embrace the present:

Write and Release

Grab a pen and jot down lingering regrets on paper. Once written, tear or crumple the paper and discard it. This simple act symbolizes letting go of past burdens and making space for new beginnings.

Create a Vision Board

Assemble images and words that represent your aspirations and goals. Arrange them on a board or digital canvas. Place it somewhere visible to inspire daily motivation and forward-thinking.

Compose a Letter to Yourself

Write a compassionate letter addressing your past decisions. Offer forgiveness and understanding, as you would to a friend. Read it aloud to internalize the message and then keep it as a reminder of self-kindness.

Share Your Journey

Discuss your experiences with friends or family. Sharing can provide support and strengthen connections. Alternatively, express your reflections through art, music, or journaling to process emotions creatively.

Set New Intentions

Identify areas in your life you’d like to improve or change. Set achievable goals and outline steps to reach them. Focus on actionable plans that align with your current values and desires.

History of Toss Away The “could Haves” And “should Haves” Day

Toss Away the “Could Haves” and “Should Haves” Day began with Martha J. Ross-Rodgers, a motivational speaker and author. She believed people often carry regret like heavy luggage.

To help others live more fully, she created a day that encourages letting go of guilt, second-guessing, and self-blame. Instead of replaying the past, the goal is to turn attention to what’s happening now. Her message is simple: move forward without dragging old mistakes behind you.

The day isn’t about ignoring what happened. It’s about recognizing that nothing changes by wishing things had gone differently.

That kind of thinking only slows progress. Letting go doesn’t mean forgetting; it means learning, growing, and choosing to focus on what can still be done. This message has reached people across the country, and each year more choose to join in.

People from all walks of life have embraced this idea. It speaks to anyone who has ever stayed stuck on “what if.”

Martha picked a Saturday in July for this event, giving everyone a reason to pause mid-year and reflect. She hoped to help others find peace, purpose, and strength in moving ahead—not by changing the past, but by living better today.