Episode 203 | The Grief Series
Nobody talks about what it feels like to watch a business you built from nothing start to shrink.
Not the dramatic crash. Not the overnight failure. The slow, grinding, humiliating version where you’re still showing up, still posting, still launching, still doing everything you’ve always done, && the numbers just keep quietly going the wrong direction while everyone around you seems to be fine.
That’s not a strategy problem. That’s a grief.
She Five-X’d Her Income. Then Lost Everything That Made That Possible.
Megan Yelaney has been in the online coaching space since 2011. She built her business coaching business to heights that most people only dream about, five-x-ing her income in a single year, hitting consistent six-figure cash months, adding $20,000 a month into her retirement account after expenses. During the golden era of 2018 to 2022, her business was printing money.
And then, within fifteen months, her father-in-law died of prostate cancer. Then her dad, who was her best friend && her greatest supporter && the most entrepreneurial person she knew, died too. In between, she had a miscarriage. When her dad passed, she was nine weeks pregnant. She didn’t always know if what she was feeling was grief or the first trimester. She almost wants to write a book just about that experience.
She had twin boys. She took maternity leave. She came back to a business that didn’t work anymore && launched a program that tanked. She told me she hated every second of that launch. So she disappeared back into the newborn bubble, told her husband it was time for him to restart his business because she didn’t know if she wanted one anymore, && tried to figure out what came next.
This episode is what came next.
The Slow Decline Nobody Talks About
Here’s what I want to sit with, because I think it’s the thing most entrepreneurs are experiencing && almost none are naming.
It wasn’t a crash. It was a slow slide. Megan first felt the dip in 2022. Not a catastrophic drop, just a shift in the numbers that made her go: huh. The next year it continued. She told herself it was the grief, the pregnancy, the circumstances. && it was, but it was also the market. Something had shifted in the industry, && the thing that had worked for years just wasn’t working the same way anymore.
By 2024, with twin boys at home && a business she’d essentially paused, she was draining her savings. She told her husband she felt like a failure. She said: I cannot believe I am saying this to you right now, when two years ago I was adding $20,000 a month to my SEP IRA.
I know that feeling. I’ve lived a version of it. && I think a lot of women listening to this have too, or they’re in it right now && calling it something else.
What Megan described as the hardest part wasn’t the lower revenue. It was the disconnect between what people assumed she was making && what she was actually experiencing. She never lied about her numbers. But she did start saying “I’ve made this much in my business” rather than “I’m making this much,” because the past felt like the only safe ground she had.
That gap between the story you’re telling && the reality you’re living is its own particular kind of grief. And it wrecks your nervous system in ways you don’t even notice until you’re deep in it.
The Identity That Was Built on Circumstances You Can’t Recreate
This is the piece I want every ambitious woman to really hear.
Both Megan && I built our biggest years during a specific era in the online coaching industry, a golden window from roughly 2018 to 2022 where people were buying differently, the market was newer, && demand was extraordinary. We both grew dramatically year over year. And because of that growth, we both built a mental picture of what the trajectory was supposed to look like.
If I’ve been doubling my revenue for four years, obviously I’m going to keep doubling it. The math just says that’s what happens.
Except that trajectory wasn’t built purely by us. It was built by us && by circumstances, a market moment, a consumer behavior that doesn’t exist the same way anymore. And when the circumstances changed, we kept comparing ourselves to the version of us that had existed inside those circumstances, wondering why we couldn’t get back there, convinced something was wrong with us.
Megan said it better than I ever have: I wish I had never made that much money. Because it painted a picture of normal that was never actually normal. And everything since has been measured against a benchmark that was never real.
That’s not failure. That’s the grief of outgrowing a version of yourself that you didn’t choose to leave.
Pretending Everything Is Fine While Your Nervous System Is Burning
One of the most honest things Megan said in this conversation was about the years when she was still publicly projecting success while privately in freefall.
She didn’t lie. She was clear about that. But she lived in this constant low-grade state of pressure, of performing certainty she didn’t have, of staying close to the story of who she used to be so she didn’t have to face who she was becoming. Her nervous system was out of whack for years. She was always trying to find the new angle, the new tweak, the thing that would get her back there.
And meanwhile, she told me, she looked around && realized: everyone else was struggling too. They just weren’t saying it either.
We are all in the same boat. We have been for years. And the reason it felt so isolating is because nobody was talking about it, so everyone assumed they were the only one.
The moment Megan started being honest about what was actually happening, the message she got back from her community was: oh my God, me too. I thought it was just me. I had no idea this was happening to anyone else.
That’s what shame in secret does. It convinces you that your experience is singular && shameful, when the truth is most people in your industry are feeling exactly the same thing.
What She Had to Let Die
Megan talked about her marriage during those peak years, && it landed hard.
She was fully in her masculine. Hustle, produce, achieve, repeat. Her husband is an entrepreneur who was completely in her corner, never threatened by her success. But there was no polarity. They were both coming at everything the same way, && her mind was always on the business, even when she wasn’t technically working.
Their separation in early 2020 was the first wake-up call. When they came back together, one of the biggest agreements was that she couldn’t just work less. She had to be actually present. && that meant letting go of some income, which meant letting go of some identity, which meant asking the question: who am I if I can’t say I make this number?
She didn’t have a clean answer. But she started loosening the grip.
What she told me she had to let die was the version of herself where everything was about money && success, where she couldn’t be without her phone, where her values were completely organized around the metrics. The person she’s being now, outside the business && inside it, she said, is so much more the person she actually wants to be.
You can make great money and be the person you want to be. She believes that. I believe it too. But it requires being honest that the version of you who made the most money in the easiest era might not be the version you want to resurrect.
Unsexily Consistent Is the Only Thing That Works
Here’s where I want to land because I think it’s the most important thing said in this entire episode.
Megan has started a public rebuild series documenting her journey back to $100K cash months. She shared her income publicly, which meant showing numbers that were a fraction of what people assumed she was making. She almost didn’t do it. She was scared people would expect her to get there fast, would measure her recovery against some impossible standard.
And then she did it anyway. Because she said: I’m not going to pretend I don’t want this. I do want it. But I’m going to want it in under 30 hours a week, && it’s probably going to take a few years, && that is normal. That is what building something is actually supposed to look like.
She called herself unsexily consistent. && she said that’s why she’s still here after all of it.
Not a magic bullet. Not a viral moment. Not a golden era that came back. Just: showing up, figuring it out, not being attached to the outcome of every single piece of content or every single launch, && trusting that the doing is the thing.
That’s it. That’s the whole answer. && nobody is selling that because it doesn’t make for a very exciting ad.
“The grief of a declining business isn’t just about money. It’s about watching an identity you built stop fitting. && the only way out is to stop comparing yourself to a version of you that was built on circumstances you can’t recreate.”
If you are in it right now, if the numbers are lower than you expected && you’re performing certainty you don’t feel && your nervous system is running on fumes, this episode is for you. You are not alone. You are not behind. You are in a real thing that real people are experiencing && not talking about.
Find Megan on Instagram at @meganyelaney && on her podcast Business Not as Usual. Go listen to the episode I did on her show too. We got into it.
This is The Grief Series. Listen now!
xx, Ash 🖤
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