Episode 197 | The Grief Series
Nobody talks about the grief of walking away from something you chose.
The grief of a death, a breakup, a loss you didn’t ask for, that we understand. We have language for it. We have casseroles and condolence cards and time off work. But the grief that comes from a choice you made, from leaving a career you built, a marriage you said yes to, an identity you spent years earning? That one you’re mostly expected to process alone, quietly, and quickly.
This episode is for anyone who has ever blown up their own life on purpose and then had to figure out how to grieve what they left behind.
The Career You Loved That Stopped Fitting
My guest, Delia Monk, is someone I met through a networking community and immediately knew I had to bring onto this series. She’s British, based in Barcelona, sharp as hell, and she has reinvented herself more times than most people would be comfortable admitting out loud.
She started as a journalist. Not just any journalist, a political correspondent who interviewed prime ministers and traveled to the European Parliament. It was the dream she’d pinned her whole identity on since she was a kid watching her dad read the newspaper over breakfast. She got it. She lived it. And then one day she had to admit she didn’t want it forever.
That admission, she told me, was where the grief started.
Because it wasn’t just a job. It was who she was. After she walked away to travel the world and eventually build a travel company, she still introduced herself as a journalist for years. “I’m a journalist, I’m just taking a year out.” Even when she wasn’t. Even when she hadn’t been for a long time.
That’s the thing about identity grief. You don’t just grieve the role. You grieve the version of yourself who wore it so confidently.
She spent the next decade building a travel business, then pivoted into copywriting and messaging, building a six-figure business over five consecutive years, working with big names, earning real credibility, becoming someone whose name was getting passed around in high circles. And then AI arrived, and she felt the ground shift overnight.
When the Thing You Built Gets Devalued
I want to talk about this because I’m hearing it from so many people right now, and I don’t think we’re being honest enough about what it actually feels like.
Delia described sitting down to write copy, something she had loved and been exceptional at, and feeling like she was being compared to a $20 monthly subscription. The trade she had spent years mastering felt suddenly replaceable. And the more she tried to keep up with it, to use AI, to stay ahead of the curve, the worse it got. It started affecting her critical thinking. Her self-esteem. It robbed the joy from writing entirely.
She came to our mentorship call having just completed a $12,000 rebrand. She had pitched 40 potential clients that week. She was doing all the things. And she was miserable.
That’s the part nobody talks about in the “pivot” content online. The version where you’re not being lazy, you’re not giving up, you’re working incredibly hard, and the work just feels like dragging yourself through wet concrete every single day. The resistance is that high. The anguish of sitting back down at your desk again that real.
There’s a difference between fear that says “this is hard but I believe in it” and fear that says “I cannot get out of scarcity no matter what I do.” Delia was in the second kind. And no rebrand was going to fix that.
Cutting the Rope
On our call, she mentioned almost as a footnote that she had this idea, helping women post-divorce navigate major life transitions, but she was sure it wouldn’t make her any money so we’d focus on the messaging instead.
We did not focus on the messaging instead.
Within ten minutes it was clear: if she didn’t follow what she was actually being called toward, she was just going to stay stuck. Not stuck in the dramatic, obvious way. Stuck in the quiet, grinding way where you keep doing the thing and adjusting the thing and rebranding the thing, but the joy never comes back because the thing was never the problem.
She needed to cut the rope. So we cut it.
The next day, she changed her Instagram bio. She posted about what was happening, raw and unpolished, no sales page, no offer, no funnel, nothing dialed in. Just: I just threw my business in the bin, and now I’m going to help other people do the same.
Six people landed in her DMs. Three became clients. A collaboration she’d been circling for months finally launched. And all of it happened without a single piece of traditional marketing.
That’s what becomes possible when you stop spending your energy holding something together that doesn’t want to be held anymore.
The Grief That Came With It Anyway
Here’s what I want to make sure doesn’t get lost in that story: letting go was still a grief.
Even when the decision was right. Even when she was excited. Even when the evidence showed up fast. She was still letting go of something she had built and loved and sacrificed for. She was letting go of the income that had felt like proof of her worth. She was letting go of a reputation it had taken years to earn. And her mother hung up on her when she found out.
That’s real. And it doesn’t stop being real just because the next chapter is better.
One of the things we worked through on that call, that I work through with every client facing a leap like this, is making sure the decision isn’t coming from a place of “this has to work or I’m finished.” Because that’s not the energy you want to carry into a new beginning. So we made a list. Not a vision board, not an affirmation, a real, practical, scrappy list of every single way she could make money if she needed to. From transition coaching, all the way down to rentafriend.com (which she did include, and yes, number 45).
You have to know you’re not trapped. You have to remind yourself that you are resourceful, that you have landed before, that there are a hundred ways to make this work. That’s not toxic positivity, that’s armor. And it makes the leap survivable.
The Other Grief: Divorce and the Life You Thought You’d Have
We also talked about divorce, and I want to spend real time here because it’s a grief I can’t personally speak to, and I know there are women listening who are right in the middle of it.
Delia was ready for her divorce. She was clear. She wasn’t grieving the marriage the way you grieve a heartbreak. What she was grieving was the life she had always assumed she would have. The childhood she grew up in, two parents, woods to play in, the quintessential family picture, and the assumption that she would give that same thing to her daughter.
That’s a particular kind of grief. The grief of a future that evaporates. Not because someone died. Because the plan changed.
She also talked about the shame. The feeling of failure that shows up even when you know the decision was right. The ambitious woman’s version of loss, where your high standards turn on you and convince you that a marriage ending is a personal failing, an insufficient effort, a box you didn’t check correctly.
And then there’s the grief that doesn’t have a resolution, the one she named that hit me hardest: giving up half of her daughter’s childhood.
She described picking her daughter up after five days apart, being first in line at school pickup, swooping her up, putting her face in her hair, desperately trying to make up for lost time. And she said something I want to sit with: all the other parents skulk into the playground because pickup is a Tuesday errand. For her it’s a reunion.
That grief doesn’t go away. It just becomes part of how you love.
What Gets Born on the Other Side
I said it in this episode and I’ll say it here: grief is the price of going all in. You can’t grieve what you didn’t love. The harder the loss, the more real the thing was.
That’s true of a career you cared about. A marriage you meant. A version of yourself you actually inhabited fully. The grief is proof that it mattered.
And here is what Delia said about reinvention that I think is the whole point: when you’re stuck in the thing that used to fit, you’re closed. You see one lane. You have one definition of how success is supposed to arrive. When you let it go, something opens. You start seeing opportunity everywhere. You become scrappy in the best way. You do improv classes in Barcelona. You launch a podcast. You say yes to collaborations that light you up.
You start living 90% of the time instead of 10%.
That’s what’s available on the other side of grief. Not because grief fixes anything. But because the willingness to move through it instead of around it is exactly what creates the space for something new to grow.
“Grief comes on the other side of going all in on something. You can’t grieve what you didn’t fully love.”
If any part of Delia’s story is yours right now, whether you’re mid-pivot, post-divorce, staring at a business that no longer fits, or just quietly wondering if you’ve outgrown the version of yourself you’ve been performing, this episode is for you.
Find Delia on Instagram at @delia.monk and at deliamonk.com.
This is The Grief Series. Listen now!
xx, Ash
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