Episode 195 | The Grief Series
Nobody tells you that getting older comes with its own kind of grief.
Not the kind that comes after a funeral. The kind that sneaks up on you in a dressing room mirror, or the morning you realize the compliments have shifted, or the day you look at an old photo and feel something you can’t quite name. The kind that lives in the gap between who you were and who you’re becoming.
This is the first episode of The Grief Series, a collection of real, raw conversations about the grief that’s woven throughout our everyday lives, not just the big losses, but the slow, quiet ones. The grief of motherhood. Of identity. Of ambition. Of aging. Because every new version of yourself you step into requires you to let another version go.
And today, we’re talking about what it actually feels like to let go of a version of yourself you really loved.
When Your Body Starts Changing and Nobody Prepared You
My guest today is my friend Bryn Daylor, someone I’ve known not just as a client and colleague but as a real, full human being I’ve had the honor of doing life alongside. We were co-working in Golden, Colorado when this conversation first cracked open, and I knew immediately it needed to be recorded.
Bryn is 36, almost 37, and she started noticing it a few years back. A streak of white hair that appeared almost overnight. A face that a facialist (in the middle of a pre-elopement facial, no less) looked at and said, “I can tell you’ve been through a lot.” Smile lines that someone on the internet complimented by saying, “I love how you smile with your whole face,” which sounds sweet until you realize what it actually means in 2025.
She’s been watching the gap widen between women her age who’ve started doing the procedures and the ones who haven’t. And she’s sitting in that in-between place a lot of us know well but rarely talk about out loud.
Here’s what she said that I haven’t stopped thinking about:
“There was a time in my life where beauty was the thing I was most recognized for. And I’ve noticed that it’s not usually the first thing people meet me in anymore.”
She talked about watching her mother and grandmother struggle with the feeling of becoming invisible, and how easy it was to judge them for that when she was younger. And how, for the first time, she’s starting to understand it.
That’s not vanity. That’s a real identity shift. And we don’t talk about it enough.
The Shame Spiral We’re Not Naming
Here’s the thing about aging in a culture that’s terrified of it: we’ve created exactly two socially acceptable responses.
Option one: reject everything. Embrace your gray, love every wrinkle, post your “natural face” content, and don’t you dare admit it’s hard.
Option two: fix everything. Get the Botox, the fillers, the facials, the procedures. And definitely don’t talk about that either, because now you’ve committed to the other side.
Both of those options are full of shame. Because both of them require you to pretend.
What we don’t give ourselves permission to do is sit in the honest middle of it. To say: some of this is hard. I miss a version of myself. I’m not sure what I want to do about it. I reserve the right to change my mind.
That’s the conversation Bryn and I are having here. Not the polished version. The one where she gets real about a procedure she massively regrets, not just financially but because it taught her something about her own body’s relationship to intervention. The one where I talk about getting bangs for two reasons: a receding hairline and not being ready for Botox. The one where neither of us knows what we’ll decide in five years, and we’re okay saying that.
What sits under all of this, what I always come back to, is shame. Beneath any struggle we have is a load of shame that, if we don’t unpack it, will continue to run us. In our business. In our relationships. In our bodies. In every area.
We’re not here to perfect the aging process. We’re here to name what’s hard about it.
The Deeper Grief: Identity, Ambition, and What We Lose
We went deeper in this episode than just bodies and beauty. Because aging isn’t only about what happens to your face. It’s about who you are becoming and who you are leaving behind.
Bryn talked about something she’s grieving that has nothing to do with wrinkles: not having had children yet. She’s almost 37, newly married, and doesn’t know what her fertility story looks like. She told me about a falconer in Big Sur who, in the middle of showing her birds of prey, got emotional and said the one thing he’d do differently is have children sooner. She said it punched her right in the gut.
“I start doing the math,” she said. “If I have my first baby at 40, that means when she’s in high school I’m close to 60. When she’s in college I’m 70.”
That’s grief, too. The grief of a timeline you didn’t choose.
And then there’s the grief of ambition shifting. Both of us have felt it. That reckless abandon, the part of you that used to just leap, that didn’t think about all the consequences because you hadn’t accumulated enough to lose yet. When Bryn left her marriage at 30, people called her brave. She told me she didn’t really think about it. She knew she wanted to leave, and she left.
She doesn’t have that anymore. Not in the same way. The leap now takes six months instead of two days. She has to think about her husband, her employees, the downstream effects.
Sometimes that makes her angry.
I get it. I really do. That scrappy, unstoppable version of me is still in there. But some of the wildness has been replaced by wisdom, and wisdom can feel like loss before it feels like a gift.
What We’re Learning to Hold
The women who age with the most grace aren’t the ones who love every part of it. They’re the ones who are honest about what’s hard, and still choose to keep going.
Bryn shared something in this episode about her daughter that stopped me in my tracks. She has vitiligo, an autoimmune condition that causes loss of pigmentation in the skin, and over the past year the spots have moved to her face and are growing. She told me for a long time she performed acceptance around it, posting about it, talking about loving it, while privately hating it more than anything she’s ever had to face.
And then she realized something: by pretending she was fine with it, she was actually teaching her daughter that you’re not allowed to have real feelings about the hard things. That you’re not allowed to feel sad.
So she started being honest. And her daughter’s response? “I love your spots, Mom. I can’t wait until I get my own spots like you.”
That’s what honesty does. It creates space for everyone around you to be human too.
At some point in this conversation, Bryn said something that I think is the whole lesson: “The wisest people in the world have just trained their mind about what to focus on.”
Are you looking at how far you have to go? Or how far you’ve come?
Are you comparing yourself to filtered, AI-generated, procedurally enhanced images and then wondering why you feel bad? Or are you actually looking at yourself?
Because you’re still here. You’re still building. You’re, statistically speaking, probably somewhere around 10:30 in the morning of your life. You have hours left.
For the Women Who Are in This Season
This episode is for you if you’re in your 30s, 40s, 50s, or beyond, and you’ve felt any version of this. The quiet grief of a body that’s changing. The strange mourning of beauty you used to take for granted. The identity shift that comes when the way people see you starts to change.
You’re allowed to feel it. You’re allowed to say it’s hard. You’re allowed to not have a neat bow on it.
That’s what Shamelessly Ambitious has always been about. Not the performance of having it together. The honest accounting of what it actually costs to grow.
“There was a time in my life where beauty was the thing I was most recognized for. And I’ve noticed that it’s not usually the first thing people meet me in anymore.”
Listen to the full episode to hear Bryn’s story about her daughter and vitiligo, the multi-generational family conversation that unfolded after her mom’s facelift, and how both of us are sitting with the question of what we’re actually willing to do (and not do) about the ways our bodies are changing.
This is The Grief Series. And this is just the beginning. Listen now!
xx, Ash
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