Letting Go of the “Should Haves”

My therapist recently warned me about my “should haves.” You know the ones: I should have done this. I should have said that. If only I had been there, maybe things would’ve turned out differently. It’s so easy to get lost in that mental maze, replaying every decision, mistake, or missed opportunity like a broken record. The list of regrets can stretch endlessly if we let it.

But here’s the truth my therapist reminded me of: there’s nothing we can do about yesterday. No amount of revisiting, reliving, or rethinking can rewrite the past. The temptation to sit with guilt, remorse, and regret over things we wish we could change is strong, but ultimately it serves no purpose other than to weigh us down.

What we can do, however, is shift our focus. While we can’t change the past, we can influence the future—but only to a slight extent. Life is unpredictable. Some things are simply out of our control, no matter how much we plan, hope, or act. That doesn’t mean we should give up and let life trample us. Quite the opposite. It means recognizing where our power lies and learning to walk forward with resilience.

Cleaning Up the Spilled Milk

The phrase “don’t cry over spilled milk” comes to mind, but let’s be honest: spilled milk can be messy. It stains, it sticks, and sometimes it even smells. Cleaning up the mess of our past mistakes—those should haves—takes effort. It requires us to sit with the discomfort of our feelings, to acknowledge the pain, and to remind ourselves that those moments don’t define us.

We talk a lot about forgiveness—forgive and forget, we say. But forgetting isn’t always possible, is it? Some moments are burned into our memories, and that’s okay. The goal isn’t to erase the past but to learn how to live with it, to carry it lightly instead of letting it weigh us down.

Forgiving yourself is often harder than forgiving anyone else. It’s an ongoing process, not a one-time event. It’s about accepting that you did the best you could with what you knew at the time, and even if you didn’t, you still deserve compassion.

The Importance of Self-Respect

One of the most important lessons I’m learning is this: self-advocacy and self-respect go hand in hand. Self-advocacy is about standing up for your needs, setting boundaries, and ensuring your voice is heard. But self-respect? That’s about how you treat yourself when no one else is looking.

Do you speak to yourself with kindness, or do you let your inner critic run rampant? Do you allow yourself the space to heal, or do you punish yourself for not being perfect?

Self-respect means acknowledging your humanity. It means honoring your effort, even when you fall short. It means understanding that you are worthy of love and forgiveness—especially your own.

Moving Forward

The “should haves” will always try to creep in. They’ll whisper to you in quiet moments, trying to pull you back into the past. When they do, remind yourself of this: you can’t change yesterday, but you can choose how you respond today.

Life will always have its share of messes. Some we’ll clean up, some we’ll step over, and some we’ll carry with us as lessons. The key is to keep moving forward, not with the weight of regret on your shoulders, but with the strength of knowing you’ve grown.

Advocate for yourself. Respect yourself. And most importantly, forgive yourself. You’re doing the best you can—and that’s more than enough.

What are the “should haves” you’re ready to let go of? Share your thoughts in the comments—I’d love to hear how you’re moving forward. See you out there.