May Magnifies the Grief of the Life You Expected

Today, I want to give voice to something that’s rarely talked about.

There’s a hidden ache that surfaces during high-celebration months — and May is one of them.

Graduations, Mother’s Day, award ceremonies, weddings, and seasonal gatherings can be incredibly painful when life doesn’t look the way you imagined it would.

Maybe your story carries the quiet weight of loss, strained relationships, financial hardship, health challenges, or unspoken trauma, the kind of pain that whispers, ‘It wasn’t supposed to be like this’. 

And now May has arrived — a month that highlights milestones — and with it, a fresh wave of grief. These events can pull you deep into what should have been.

I’ll never forget the gut-wrenching pain of watching smiling teens in prom attire gathering for photos with their parents in our neighborhood in 2022. That seemingly ordinary moment landed heavier than expected, making the gap in my reality feel vast, and the heartbreak nearly impossible to hold.

When I finally made it through that two-year family crisis, I promised myself something:

  • That I wouldn’t forget the sting of seeing “milestone” reminders that only deepened my grief.
  • That during these celebration-heavy months, I would offer a soft place to land for anyone quietly hurting on the outskirts.

Because the pain of “this isn’t how it’s supposed to be” often has nowhere to go. It’s not something we can easily explain or even say out loud. 

And the loneliness of it can be the most isolating part.

So, over the past few days, I’ve done my best to give that pain some words. What follows is a poem I wrote from that tender place — for anyone carrying quiet sorrow in a season of celebration. It’s for the ones smiling through tears, staying home from the gathering, or simply trying to make it through the month.

A May Blessing for Hidden Hurt
by Rachel Macy Stafford

May you proceed knowing that your story is sacred—
even the parts that broke your heart,
even the moments that didn’t go as planned.

May you give yourself permission to feel,
to grieve without rushing,
to rest without guilt,
and to honor the ache asking to be seen.

And when sadness rises again, as it will,
may you meet it with softness—not shame.
With breath, not blame.
With the quiet courage to say: “Maybe it just is.”

In your brave release of “what should be”,
may comfort reach what hurts
and assure you that you are not alone.

My hand in yours,
Rachel


AN INVITATION…

One of the most profound lessons I learned while supporting my family during a challenging season was this: I am a worthy recipient of my own caregiving.

As givers, we often show up for others, pouring our energy into helping them heal and grow. But we sometimes forget that we too need space to rest, replenish, and reset. Good caregivers need good care, and it’s never too late to claim that for ourselves.

That’s why I’m excited to invite you to an opportunity for deep nourishment and healing: a retreat designed for those who give so much to others but often forget to care for themselves.

This fall, I’m offering a brand-new ONLY LOVE TODAY weekend retreat for givers, helpers, and hearts in need of a reset, hosted at the Art of Living Retreat Center in Boone, NC, from November 7-9.

Imagine:

  • Setting aside the weight of your daily responsibilities and reconnecting with the parts of yourself that need your care.
  • Breaking free from the cycles of stress and exhaustion that keep you stuck.
  • Creating a personalized plan to offer yourself the same love, care, and compassion you so generously give to others.
  • Immersing yourself in the serenity of the Blue Ridge Mountains, with nourishing meals and the support of like-hearted individuals on a similar path.

This late Autumn respite is a chance to pause, reset, and nourish your soul before the busy holiday season begins. Space is limited, so if you’re ready to prioritize your own well-being, please sign up today. 

And if traveling is out of the question, you can still experience a similar sense of community and restorative teachings through my metaphorical home, Rachel’s Treehouse. It’s a place for my words and a shared connection with each other, where we can dive deep into healing, self-love, and compassion from wherever you are. Some of the most-read essays so far in 2025 have been:

Climb my treehouse ladder. I will welcome you with open arms.

Hands Free Mama

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