I Regret the Regrets

Lauren Osborn
4 min readSep 9, 2022

“It’s only heavy if you hold it.”

Regrets and resentments. What started as pesky pebbles in my shoe grew into boulders atop me, my mind and heart never able to escape their crushing weight. The etymology of regret is “to wail for the dead”, and that of resentment is “to feel again and again.” Their roots make their futility even more striking, but there was no escape from the endless loop of how my thoughts flowed within their swift, rapacious current of suffering.

For years upon years, I punished myself not for what I said, but for what I didn’t and wished I had:

“Lauren, are you ok?” “Yes, I’m fine”, an autopilot response ages 6–31. (“Things are so hard.”)

“Did someone hit you? “No, I fell”, as I lied to protect my caretakers. (“I am not safe at home. Please help me.”)

“Lauren, are you eating enough?” “Yes, I must be going through a growth spurt.” (“I starve myself. It’s the only feeling of control I have in the chaos and trauma at home. Please keep asking me. I need someone to see I need help.”)

“Do you know what sobriety is?” “Yes, kinda,” as I changed the subject and ended things with him (whom I loved deeply) a few days later. (“I’m an addict and I need help.”)

“Did you cut yourself?” “No, I fell in a rosebush.” (“Yes, I harm myself. Things are unbearable inside. I need help.”)

“Lauren, are you ok?” “Yes, I’m fine.” (“I can’t do this anymore. I can’t see a way out besides ending it all. Please help me. Now.”)

Then it happened. I was teetering on the edge of the subway platform as the 4 train barreled into the 86th St station. Something inside of me that felt like magnetic force turned my body away and led me upstairs. A single text: “I need help.”

Years of addiction and trauma recovery buoyed by daily meditation helped me to heal, helped me to actually love myself, helped me to live mostly in the present moment with equanimity. But my mind would sometimes tiptoe back to the things I think I should have done, should have said. It would send me into a painful spiral of shame, guilt, remorse, and anger at myself. I was very aware that wishing I could do the past differently was futile, that wishing I could go back in time was causing suffering in the present moment. Once again, I needed help. This time I sought it out before the juggernaut of my mind sent me on the path of utter despair and destruction.

Buddhism talks about the pain of the second arrow (my reaction to an event), which is worse than that of the first (the event itself.) I was torturing myself with my regrets- which manifested into present day emotional reactions based upon things I did or did not do in the past (the subconscious will always present itself in conscious actions.)

I started watching my thoughts during meditation, which eventually granted me awareness of when it would go back to dig up regrets. An epiphany: I was punishing myself now for living as best I could with the tools I had at that time.

I began practicing radical forgiveness and compassion towards myself in the now. I kept seeking help through books, poetry, spiritual teachers.

And then, I found the writings that have been my ultimate source of freedom from shame and regret: W. S. Merwin’s poetry about mistakes (Wild Oats and To the Mistakes, specifically). They cracked me open to the wholeness and completeness of this moment, of my life, of my story. I suddenly realized deep in my being that I needed every choice, every mistake, every moment of my life to get me to this present moment which I now love deeply . When I make “mistakes” today, I lean into the thought that they are simply redirecting the great, mysterious river of my life to flow where it ought. This perspective avails me to radical forgiveness- and ultimately, freedom from the painful bondage to the past. All I want is a heart tethered soundly in this present moment by grace and love for all, including- perhaps especially- myself.

For this I know to be true: I can only love others to the extent I love myself, and that includes every misstep, every mistake, every instance of self-sabotage and self-harm. They are mine and mine alone. May I practice continuous mercy and gratitude for it all.

When I am free from the bondage of the past, I get to live moment to moment in wonder and awe.

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Lauren Osborn

Seeker of all things wild + free. Actor. Storytelling about impermanence, Nature, addiction + recovery, the space between life + death, the magic of presence.