Could Haves and Should Haves

July 15 marks National Toss Away the Could Haves and Should Haves Day, and that is a day we can all use in our lives, isn’t it? This day was created by Martha J. Ross-Rodgers, an author and motivational speaker.

If you’re into following these special days to the letter, you should write down all your “could haves” and “should haves” and then crumple up and toss that paper into file 13.


We all have mixed feelings about how we handle regrets. The old adages are that we must learn from our mistakes and know our history so we’re not cursed to repeat it, and there is tremendous value in these ideas. But there is a big difference between knowing how we messed up, or failed to act, and beating ourselves up with that knowledge every day for the rest of our lives.

Holding onto regret doesn’t allow a person to engage fully in the here and now; it only keeps us tethered to a past that cannot be fixed or changed. We can only mindfully act differently in this moment. Keeping ourselves tied to the past, as if it is a ball and chain, only hinders our movement forward; we might run or fly, but we’re too weighed down to do that. We need to have more empathy for ourselves than this.

An exercise you might consider to help forgive yourself is to pretend that a friend has shared with you whatever regret you have. How would you respond to your friend? What words would you say to them? Write those down, but address the letter to yourself. Write the letter. Read the letter. And then tuck it away to read it again. We are often so much more gentle and compassionate with others than we ever are with ourselves. 

If you haven’t already, talk to someone about your regret, whether that person is a therapist, pastor, or friend. If you haven’t taken the time to work through why you’re hanging onto your “could haves” and “should haves,” do so now. All those experiences are lessons to build on, necessary steps to reach your goal. They are not the failures you might think they are. Adapting this new mindset will change your life.

About Deedee Cummings

As a therapist, attorney, author, and CEO of Make A Way Media, Deedee Cummings has a passion for making the world a better place. All 16 of Cummings’ diverse picture, poetry, and workbooks for kids reflect her professional knowledge and love of life. Colorful and vibrant, her children’s books are not only fun for kids and adults to read, they also work to teach coping skills, reinforce the universal message of love, encourage mindfulness, and facilitate inclusion for all. Cummings has spent more than two decades working within the family therapy and support field and much of her writing shares her experiences of working with kids in therapeutic foster care. As a result, her catalogs of published books for kids are filled with positive, hopeful messages. Using therapeutic techniques in her stories to teach coping skills, Cummings also strives to lessen the stigma that some people feel when it comes to receiving mental health assistance.
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