Let’s face it—we’ve all done it.
Stared at the ceiling thinking “I should’ve spoken up in that meeting…”, “We could have gone on that trip in 2019…”, or “Why didn’t I buy stock in literally anything online in 2008?”
If you’ve ever been haunted by a “could have” or “should have” (or 200 of them), you’re not alone. That’s exactly why National Toss the “Could Haves” and “Should Haves” Day exists—landing every year on the third Saturday of July (this year, July 19th).
It’s a day to let go. Lighten the mental load. Free ourselves from the baggage of decisions past, missed opportunities, and the "what ifs" that serve no one—except maybe that voice in your head that sounds suspiciously like your second cousin Susan (not to insult anyone who’s name is Susan).
Let’s dig into what this day really means, why it might matter more than you think, and how you can celebrate it in ways that are fun, useful, and possibly even a little bit freeing.
What Is National Toss the "Could Haves" and "Should Haves" Day?
Created by motivational speaker Martha J. Ross-Rodgers, this day is about releasing regret. It’s not a gimmick—it’s a gentle nudge to help us move forward instead of staying stuck in a loop of hindsight.
Imagine Marie Kondo-ing your emotional closet. Every “I should’ve taken that job,” or “I could’ve spoken up sooner” gets kindly thanked for its lesson and tossed out to make room for clearer, calmer thinking.
This isn't about ignoring the past. It’s about learning from it without living in it.
Why It Matters More Than You Think
Regret is sneaky. It doesn’t always come in the form of dramatic failures—it often lurks in everyday choices: not starting a hobby, missing a chance to reconnect with someone, or skipping that Sunday nap (the true tragedy).
While some reflection is healthy, when we marinate too long in the "coulda-shoulda" stew, it holds us back:
Creativity shrinks because we're afraid to try again.
Decision-making stalls because we're overanalyzing every outcome.
Joy fades because we're too busy rehashing the past to enjoy the present.
Sound a little familiar? Then this day might be for you.
Common “Could Haves” and “Should Haves” (And Why You Can Toss Them)
Let’s call a few of these out in the open, shall we? Air them out. Then promptly toss them out.
🏠 “I should have bought that house in 2015.”
You and half the country. Real estate hindsight is basically a national sport. But here's the truth: You made the best decision you could with the information you had at the time. And besides, housing markets rise, fall, and rise again. There will always be opportunities—just not always in the same package.
💼 “I could have started my own business.”
Maybe. Or maybe the timing wasn’t right. Or the idea needed more time to simmer. The great thing about this dream is—it’s still alive. Maybe today is your first step forward.
❤️ “I should have said yes to that date/job/change.”
What ifs can be painful. But sometimes a “no” teaches you just as much as a “yes.” Trust that you said no for a reason—and that reason may still be valid.
🧁 “I could have said no to that third cupcake.”
No regrets. Cupcakes are cupcakes.
How to Celebrate: Your Toss-the-Should-Haves Game Plan
📝 1. Make a (Short) Regret List—Then Rip It Up
Grab a notebook or even the back of a grocery receipt. Write down a few things you’ve been hanging on to. Not the epic life-altering regrets—just the ones that randomly pop up while brushing your teeth.
Then? Crumple it. Burn it (safely). Shred it. Or ceremoniously toss it in the compost with the week-old spinach. Goodbye, mental clutter.
🧠 2. Flip the Script
Instead of thinking:
“I should have moved last year,” try: “What would make moving right now feel good?”
“I could have saved more,” try: “What’s one small thing I can start doing today?”
This isn’t toxic positivity—it’s giving yourself permission to move from stuck to strategic.
🌱 3. Try Something You’ve Been Avoiding
What’s one little “should” you’ve been carrying?
“I should learn to cook something that doesn’t involve a microwave.”
“I should actually go on that hike I keep talking about.”
“I should finally sort the junk drawer (or at least close it all the way).”
Pick one. Do it just a little bit. Celebrate the progress, not perfection.
💬 4. Reach Out, Don’t Ruminate
If one of your regrets involves another person—like not calling a friend back in 2021 (or 2011)—it’s not too late. Send a message. Make a call. No need for a dramatic reunion. A simple “Hey, you crossed my mind” works wonders.
🧘 5. Create a “Done Right” List
We spend so much time on what we didn’t do, we forget to notice what we did do.
Got out of bed when it was raining? Win.
Remembered your friend’s birthday without a Facebook reminder? Superhero.
Took a deep breath instead of sending that snarky email? Nobel Peace Prize, practically.
Write down 5 things you’re proud of, big or small. It’ll surprise you.
Real Talk: Regret Happens to Everyone
From 20-somethings wondering if they picked the right major, to retirees wondering if they should’ve traveled more, regret is universal. No one gets through life without a few “oops” and “if onlys.”
But we don’t have to build a house and live in them.
We grow. We learn. And we get better at understanding what matters to us now—which is all we really have control over.
And If You Must Keep One “Should Have”…
Let it be something like:
“I should have taken more time to enjoy where I am.”
“I should have appreciated how far I’ve come.”
“I should have realized that perfect doesn’t exist, but contentment might.”
Those are the kind of shoulds we can live with.
A Quick Note from Your Local Real Estate Enthusiast (We Promise This Isn’t a Pitch)
Sometimes our biggest “could haves” and “should haves” involve where we live. Homes come with big emotions and big decisions. If you’re ever wondering about what ifs—like “should I downsize?” or “could I find a better fit?”—just know it’s okay to ask questions without committing to anything. That’s how good decisions start: with curiosity, not pressure.
But today isn’t about that.
Today is about letting go, lightening up, and maybe—maybe—laughing a little at the fact that we once thought buying a bread maker in 2020 would make us a whole new person.
Final Thoughts: Your New Motto
Toss it and move on.
That’s it. That’s the blog.
Okay, not really—but it could have been. 😉
Whether you're tossing emotional clutter, a to-do list that’s haunting your fridge, or just giving yourself the freedom to breathe a little deeper, July 19th is a great day to practice the art of letting go.
Here’s to fewer regrets, more joy, and just the right number of cupcakes.
Happy National Toss the "Could Haves" and "Should Haves" Day!
If this made you smile—or if you have a hilarious regret you'd like to share (an orange shag carpet in 1983, perhaps?)—hit reply or drop a comment. We'd love to hear it.
