Getting fired sucks.
But you know what sucks even more? Trying to figure out health insurance while you're still processing the shock, dealing with the financial anxiety, and frantically updating your LinkedIn.
Our CEO Andy Hamilton was featured in the new book All the Cool Girls Get Fired: How to Let Go of Being Let Go and Come Back on Top by Laura Brown and Kristina O'Neill. These two former editors-in-chief got publicly fired from InStyle and WSJ Magazine. Instead of hiding it, they owned it, wrote about it, and created a survival guide for the rest of us.
"OK, This Is the Brain-Melting Part"
In the book's Health Care section, Andy doesn't sugarcoat the absurd reality. There are hundreds of health insurance options but no real help navigating them:
"There are no classes on shopping for health insurance. It's not something we do because we traditionally get it from our employer. So, when you lose your job, if you're like many people, this is the first time you've ever had to shop for health insurance on your own and it's at the most stressful, painful part of your career. You're worried about getting a new job. You're worried about putting food on the table. And, by the way, you have to sort through three hundred plans and find the ideal health insurance for you or pay a crazy premium."
This is what led to the creation of When.
Why This Book Matters
All the Cool Girls Get Fired isn't your typical career advice book. It's a raw, honest, and fiercely funny roadmap through one of the most destabilizing experiences in modern work life. It includes exclusive interviews from Oprah Winfrey, Katie Couric, Jamie Lee Curtis, and dozens of other accomplished women who've been there.
Laura Brown and Kristina O'Neill lived this. Brown was fired from InStyle in February 2022, O'Neill from WSJ Magazine in April 2023. Instead of spinning it or hiding it, they posted a selfie captioned "All the cool girls get fired" and the response was overwhelming. Women everywhere reached out sharing their own stories, revealing just how much shame and isolation people feel around job loss.
The book has already received rave reviews:
Publishers Weekly (starred review): "An inspiring roadmap for navigating career curveballs"
The New York Times: "Covers subjects that have only become more relevant as firings, layoffs and economic uncertainty have become topics of daily conversation"
Forbes: "Actively creating a community that can serve as a support system"
The celebrity endorsements tell you everything:
Oprah: "The setback is a setup"
Naomi Watts: "A revolutionary book: an indispensable tool for bouncing back"
Rose Byrne: "To all the fired ladies out there: Congratulations, you just got cooler"
Why We're in This Book
Look, Brown and O'Neill cover everything. The emotional rollercoaster, the financial panic, the awkward networking events where you pretend you're "exploring opportunities."
But they knew they had to tackle the health insurance monster. Why? Because it's the thing nobody talks about but everyone panics over. You can handle the ego hit of getting fired. You can deal with updating your resume. But that moment when you realize you have 60 days to figure out health coverage or pay $2,000 a month for COBRA? That's when the real panic sets in.
Andy's quote hit a nerve because it's the conversation we have every single day at When. Smart, capable people who've navigated complex careers suddenly feeling like idiots because they don't know what a deductible actually means. Parents doing 3 AM math trying to figure out if they can afford their kid's medications. People taking jobs they don't want just for the benefits.
It's broken. And When was built to solve this problem.
From "Brain-Melting" to "We Got You"
The authors nail their approach: acknowledge the hard stuff, provide real solutions, and build community around shared experience.
We're doing the same thing for the health insurance piece. When that 60-day COBRA deadline panic hits, we step in. While HR handles the exit paperwork, we handle the health insurance mess. We match people with marketplace plans that cost way less than COBRA. We provide actual humans who guide them through enrollment, answer the "what about my prescriptions?" questions, and make sure there's no coverage gap.
We're not trying to revolutionize healthcare. We're just fixing this one broken transition point. Because when you're already dealing with a job loss, becoming a health insurance expert shouldn't be part of the equation.
Simple as that.
Get the Book
If you've been fired, laid off, restructured, or "eliminated," you're in good company.
All the Cool Girls Get Fired is available now.
And when you get to that "brain-melting" health insurance part?
We got you.
