Letting Go of the 'What Ifs' and 'Should Haves'

Introduction

Grief and loss often come with lingering questions: What if I had done something differently? I should have said more, done more, been more.

These thoughts are natural but can become a mental trap, keeping us stuck in guilt and regret.

For me personally, the what-ifs and should-haves weighed heavily on my mind for all the losses in my life.

For my Dad – he was living in an old-age facility when he had a fall a few days before his stroke and subsequent brain bleed. I had followed up with the nurses that day, requesting a doctor’s visit, but later, my dad told me no such visit occurred. I later discovered that the fall was never recorded, and no doctor had been called. Two days after the doctor was finally requested, he was gone. The should-haves and what-ifs were overwhelming. What if I had a home with one level so he could have lived with me instead of in a facility? What if I had called every day until a doctor examined him? I should have spent more time with him, but COVID stole that opportunity. I spiraled into self-blame, believing that if I had been a better daughter, he would still be here.

With Dakota, my son, the weight of regret was even greater. What if I had gone home with him that night instead of staying with my dad at the hospital? What if I had been there when he passed—could I have gotten him to the hospital in time? I should have been a better mother. I should have kept him away from trouble. I should have been there to fix it, just like I always had. My deepest, darkest thought was that maybe I was the reason he was gone. The blame I placed on myself was suffocating.

The Psychology Behind Regret and Grief

Why Do We Hold Onto Regret?

• The brain seeks closure and understanding, leading us to replay past events in an attempt to "fix" the unchangeable.

• Studies show that counterfactual thinking (thinking about alternative outcomes) is common in grief but can prolong emotional pain (Roese, N. J., 1997).

The Impact of Regret on Mental Health

• Neuroscientific research shows that excessive regret activates the same brain regions associated with stress and anxiety, such as the prefrontal cortex and amygdala (McLaughlin, K. A., et al., 2015).

• Unresolved guilt can lead to depression, self-blame, and even physical health issues, including increased cortisol levels and disrupted sleep patterns (Kubzansky, L. D., & Kawachi, I., 2000).

  
  

My Personal Journey with Letting Go

Regret consumed me as soon as I lost Dakota. I could have fixed this! I convinced myself. I could have moved him, performed CPR, told EMS they had to take him to the hospital.

The overwhelming sadness and self-loathing that followed were debilitating. I wanted to die with him. I wished I could trade places. For months, I did nothing—I barely moved from the couch, my bed, or his room, where I would collapse, screaming and crying into his pillow.

The Turning Point

After 16 months, the medical examiner contacted me with news that changed everything. Dakota had a hairline cut in his adrenal glands, which had been slowly leaking toxins into his body. It was a rare complication of diabetes, one that would not have been detected in time. There was nothing that could have been done.

That revelation forced me to confront the truth—I wasn’t responsible for his death. But accepting that truth was its own struggle. Even now, I sometimes wonder if I could have saved him from his diabetes, from himself.

How to Release the ‘What Ifs’ and ‘Should Haves’

1. Acknowledge and Accept the Feelings

Suppressing regret only makes it stronger. Research suggests that actively engaging with grief through journaling, therapy, or speaking with trusted people can help process these emotions (Pennebaker, J. W., & Beall, S. K., 1986).

My experience: Admitting to myself that I felt responsible for my losses was the first step toward releasing the weight of my regrets.

2. Reframe the Narrative

Instead of saying, I should have…, shift to, I did the best I could with what I knew at the time. Cognitive reframing reduces negative thinking and promotes self-compassion (Neff, K. D., 2011).

My experience: Over time, I started to remind myself that I had acted out of love, not negligence. I was human, not all-knowing. This shift was crucial in my healing.

3. Practice Self-Forgiveness

Studies show that self-compassion enhances mental resilience and aids in grief recovery (Germer, C. K., & Neff, K. D., 2013).

Practical exercises:

• Writing a forgiveness letter to yourself

• Practicing mindfulness and grounding techniques

• Seeking guided meditation for self-compassion

My experience: The moment I allowed myself to believe that I was still worthy of love—even after loss—was the moment I started moving forward.

4. Find Meaning in the Loss

Viktor Frankl’s Man’s Search for Meaning discusses how finding purpose in suffering helps us heal (Frankl, V. E., 1959).

Ways to honor your loved ones:

• Creating a legacy in their name

• Performing acts of kindness

• Pursuing personal growth in their honor

  
  

My experience: Choosing to share my story has been one way I keep Dakota’s memory alive. Helping others navigate grief allows me to honor both him and my dad by turning pain into purpose. I practice mindfulness and grounding whenever I need to recenter myself. Every December, on Dakota’s birthday, I choose a charity he would have wanted to support and rally others to donate in his honor. This tradition brings me comfort, knowing his impact continues.

There are other ways I want to honor him, but I’m not quite ready yet—and that’s okay. Healing isn’t about rushing; it’s about taking each step as I’m able. I remind myself that every step forward, no matter how small, is still a Bold Step Forward toward healing.

I also want to be honest with you—I am nowhere near perfect at this. I am still on my own healing journey, still learning, and still figuring things out as I go. That’s part of why I use AI to help shape these blog posts. Some of the research and insights shared here are things I’m learning alongside you. Healing isn’t something we wake up one day having mastered—it’s a process, and sometimes, we have to seek knowledge and guidance along the way. So, as I write this, know that we are walking this path together, learning, growing, and taking Bold Steps Forward—one at a time.

Letting go doesn’t mean forgetting—it means making peace with what we cannot change.

Healing is a journey, and it’s okay to take time. If you’re struggling with the ‘what-ifs’ and ‘should-haves,’ remind yourself of this: Regret looks backward, but healing moves forward

#boldstepsforward #healingjourney #missmyson #griefjourney #movingforward #lettinggoofregrets #lossoflovedone