Letting Go of the “What Ifs” and “Should Haves”

As I am entering a new chapter in my life — one that is exciting, uncertain, and deeply personal — I’ve noticed how often my mind wanders into a space filled with what ifs and should haves. 

What if I had made this change sooner? 

What if I’m not ready? 

I should have been more prepared. 

I should have known better. 

I should be further along by now. 

Sound familiar? 

These thoughts can feel like facts. They disguise themselves as helpful introspection or self-improvement, but too often, they’re just anxiety in a different outfit — tightening their grip and pulling us into a spiral of regret, self-doubt, and hesitation. 

The Anxiety of Hindsight 

Anxiety loves to live in the past and the future. It thrives in the “what ifs” of tomorrow and the “should haves” of yesterday. But the cost is steep: when we focus too much on what we didn’t do or what we fear might happen, we disconnect from what is happening — the present moment, the opportunities in front of us, and the person we are right now. 

This habit of self-questioning can be paralyzing. It convinces us that we’re behind or broken or not enough. And for many of us — especially women, caregivers, or those of us who have made sacrifices for family, stability, or others’ needs — it can feel like our worth is always tied to doing more, doing better, or doing it “right.” 

Rewriting the Narrative 

But here’s the truth I’m working to live by — and maybe it will resonate with you, too: 

I am not a collection of missed opportunities. I am a culmination of resilience, experience, growth, and courage. 

Every “what if” carries a lesson. Every “should have” is really just a point of perspective. And while reflection can be a powerful tool, it loses its value if it’s only used to tear ourselves down. 

Instead of asking “what if I fail?” I’m learning to ask, “what if this works?” 

Instead of saying “I should have done this earlier,” I remind myself, “I did it now — and that’s what matters.” 

Holding Confidence and Compassion 

Moving forward with confidence doesn’t mean shutting out fear or anxiety. It means allowing both to be present, but not in control. It means affirming your value — not based on a perfect record, but on who you are: capable, thoughtful, and human. 

So today, I’m choosing to pause when the “what ifs” creep in and ground myself in the truth of what is: 

• I am entering a new chapter because I’m ready for change. 

• I bring value, even when I feel uncertain. 

• I don’t need to have it all figured out to begin. 

An Invitation 

If you find yourself living in the land of “should haves,” you’re not alone. Take a moment to breathe, reflect, and remind yourself: your journey is unfolding exactly as it’s meant to. The past shaped you, but it doesn’t define your worth — and the future is still being written. 

Let’s give ourselves permission to show up imperfectly — with hope, with heart, and with confidence in who we are becoming.