Borrow what we learned.
The mistakes, checklists, and decisions we wish someone had handed us sooner.
Open the free kit ↗For people who thought they'd have it figured out by now.
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The mistakes, checklists, and decisions we wish someone had handed us sooner.
Open the free kit ↗Dear Shitshow is where we tackle the complicated decisions nobody puts in their LinkedIn announcement.
Ask Dear Shitshow ↗What happened? What helped? What did you spend too much on? Your experience might save somebody a very expensive Tuesday.
Here’s the deal: you can take the tools without joining anything. You can also share a lesson or send a question. For now, this is an editorial club—not a forum or a member-matching service. No story goes public without review and explicit permission.
Because “you've got this!” is not a business plan. Five starter tools for the moment when everything feels wonderfully, terrifyingly up for grabs.
Free. No email hostage situation. No surprise mastermind invitation.
Open a kit, check off what you've done, and print your own survival sheet. These are practical prompts informed by what we're learning, not a guarantee that everything works out.
Maybe you should leave. Maybe not yet. Before making a big move, ask yourself some very unromantic questions.
If your change wasn't voluntary, skip the guilt trip. Start with practical stabilization and the first choice you can control.
These are starter rules of thumb, not a claim about purchases Mel and Francesca personally made. We’ll add specific receipts when we can verify them.
Not what your last employer paid you. Not what a stranger on LinkedIn claims to charge. Start with four real inputs:
A price is a hypothesis until someone agrees to pay it. Get professional tax and legal guidance where appropriate.
You bring the situation. We bring two opinions, decades of experience, and potentially conflicting advice.
FIVE QUESTIONS / THE CLUB’S TAKE
Career plot twists, identity crises, money, friendship, and the occasional spectacular what-now. Here are five questions we keep coming back to—and what we think about them. Got a real one? Send it our way.
Woof. We get this one.
One of us was there. One day, she walked into her husband’s office and said, “I want to quit. Take three months off. Figure out what the hell I’m doing next.” His response? “Do it.”
We recognize not everyone has that luxury. Money is real. Whoever claimed it can’t buy happiness clearly never lived paycheck to paycheck.
But you know what else is real? Energy.
If you wake up hating your job every day, eventually that starts bleeding into the rest of your life.
So no, you’re not ridiculous. You’re paying attention.
Our advice? Ask yourself a different question. Not just What do I want to do next? but What do I want my life to feel like?
For one of us, it was a calm nervous system. She wanted to stop feeling like she was humming all the time.
And listen to your body. Hers was trying to tell her something long before she listened. Hence, the bite guard.
You don’t have to quit tomorrow. But don’t ignore what you’re feeling just because the paycheck is good.
Because selling your own work is really freaking personal.
Inside a company, you had a title, a team, established relationships, and a big-ass organization behind you. Now? It’s just you. No corporate credibility blanket. No boss vouching for you. Just you, asking someone to pay for what you know.
That’s vulnerable as hell. Also, weirdly liberating.
After countless hours and some truly spectacular elevator-pitch fumbling, here’s what we’ve learned: Stop trying to sell yourself. Start talking about the problem you solve.
Get crystal clear about who you’re helping and what’s keeping them up at night. Then get curious. Ask questions. Listen.
Suddenly, it’s less about proving how impressive you are and more about whether you can actually help.
There are selling techniques you can learn. Absolutely.
But the ego part? The rejection? The feeling that someone saying no to your proposal is somehow saying no to you?
Woof. That’s the real work.
And for the record, we’re still working on it.
First, getting laid off can really screw with your head.
Even if you hated the job, losing it when it wasn’t your decision can bring up a whole mess of feelings. Anger, grief, relief, panic. Sometimes all before breakfast.
And when you’ve spent decades building a career, losing the job can feel a little like losing yourself.
So before you start plotting your glorious reinvention, give yourself some room to process what happened. As much as your finances allow.
Then we’re going to ask you a deeply annoying question.
What do you actually want?
Not what your résumé says you should do. Not what someone with your experience is supposed to want.
What kind of life? What kind of income? What kind of work?
Because the answer might exist in your old career. Or it might be something entirely different.
And with AI changing so much about work, there’s plenty of uncertainty. But there’s also a whole lot of new territory opening up.
And if the answer is “I have absolutely no freaking idea,” congratulations. That’s a perfectly legitimate place to start.
First of all, awesome. We’re excited for you.
But here’s something we’ve learned: starting a business with a friend is a lot like getting married.
We actually call each other work wives. We share finances, an LLC, a brand, and a legally binding relationship. Romance!
So before you jump in, have the conversations. Where is this business going? Who does what? How much are you each investing? What’s ours versus yours? And what happens if one of you wants out?
Get it in writing.
But here’s the bigger thing: You will not always agree.
Someone will get their feelings hurt. Someone will carry more of the load. Life will happen. And occasionally, you’ll wonder what the hell your partner is thinking.
The trick isn’t avoiding those moments. It’s being able to talk about them before resentment moves in and starts paying rent.
For us, candid feedback, different strengths, and a lot of mutual respect make it work.
Choose someone you can disagree with and still want to call tomorrow.
Then go get a job!
Seriously. Somewhere in our 20s, we learned to never say never. And thank God, because we’ve changed our minds about approximately a million things since then.
Starting a business was right for a season of your life. Amazing. Maybe now you miss a steady paycheck, colleagues, or having someone else deal with the damn invoices.
Great. Go find that.
Who decided entrepreneurship was a one-way street anyway?
Maybe you’ll love being back in a company. Maybe in two years you’ll get another idea and want to start something completely different.
Also great.
Life isn’t linear, and you’re not contractually obligated to stick with a decision just because you announced it on LinkedIn.
Don’t let the coulda-woulda-shouldas, or what other people might think, keep you somewhere you no longer want to be.
You want to go back? Fucking go! We love a good plot twist.
Wondering whether to quit? Pricing an idea? Thinking about going back to corporate? Tell us what you're wrestling with.
Different beginnings. Plenty of shared lessons. The awkward in-between, questionable decisions, and things worth passing on.
Pick the one that sounds familiar. Explore some recognizable situations and the lessons worth passing along. No personal disclosure required.
Or skip the labels and browse everything below. Nobody's grading you.
A few stories to get us started. These first six are fictional; the mess is very real. Have a story of your own? We’d love to hear it.
“I used to manage 140 people and a multimillion-dollar budget. Yesterday I spent 47 minutes trying to connect a printer to Wi-Fi.”
WHAT HELPEDRealizing that not being needed by 140 people every day doesn’t mean you’re no longer valuable. Still working on believing it.
I used to manage 140 people and a multimillion-dollar budget. Yesterday I spent 47 minutes trying to connect a printer to Wi-Fi.
I nearly cried. Not because of the printer. Well, a little because of the printer.
When I quit, everyone kept saying how brave I was. Which was lovely, except I didn't feel brave. I felt like someone who'd walked out of a building and left half her personality inside.
I miss my assistant. I miss knowing exactly what I'm supposed to do when I wake up. I even miss some of the meetings I spent years complaining about.
I don't miss the Sunday-night stomachaches, though.
Anyway, the printer works now. My business doesn't make any money yet. And I'm trying to stop measuring the value of my day by how many people needed something from me.
It's going... unevenly.
“23 years. That’s how long I worked there.”
WHAT HELPEDGiving myself permission to stop applying for jobs I don’t actually want. Also, asking people to stop telling me to enjoy my time off.
23 years.
That's how long I worked there.
They told me on a Tuesday morning. By lunch, my access was gone. My team sent some really nice messages. A few people didn't say anything. That bothered me more than it should have.
The first week, I kept opening my laptop at 7:30 out of habit.
The second week, I started applying for jobs. Anything vaguely close to what I'd been doing. I didn't even want half of them. I just needed to feel like I was doing something.
My wife keeps telling me to enjoy the time off.
I know she means well.
But I don't know how to explain that it doesn't feel like time off when you're not the one who chose it.
People keep asking what I'm going to do next. I wish they'd stop.
I don't know yet.
“Nothing is technically wrong with my job.”
WHAT HELPEDGetting curious before making dramatic decisions. Talking to people with completely different jobs instead of immediately updating my résumé.
Nothing is technically wrong with my job.
Good company. Nice people. Decent money. Reasonable boss. I realize this makes me sound like an asshole for complaining.
But I was sitting in a meeting last month, listening to everyone debate something we'd debated approximately 900 times before, and I thought: I cannot do another 15 years of this.
Not because I couldn't. Because I could do it in my sleep.
That's almost the problem.
I have no dramatic exit story. No toxic boss. No big entrepreneurial dream. I just keep finding myself reading about completely different careers at 11 p.m.
Last week I looked up how much dental hygienists make.
I have absolutely no interest in teeth.
So that's where we're at.
“Monday, 8:07 a.m. I have quit my job. I am a free woman.”
WHAT HELPEDDiscovering that not every free hour needs to be filled with something productive. The walks are helping. Annoyingly, my husband was right.
Monday, 8:07 a.m.
I have quit my job. I am a free woman.
8:42 a.m. Made coffee. Sat outside. This is incredible.
9:15 a.m. Checked LinkedIn.
9:47 a.m. Checked LinkedIn again.
10:30 a.m. Started making a list of things I should accomplish during my time off.
11:00 a.m. Realized I have somehow turned unemployment into a performance improvement plan.
By Wednesday I'd reorganized the garage, signed up for a course I don't want to take, and asked my husband if he thought I was wasting my potential.
He asked if I'd considered going for a walk.
Rude.
I spent years dreaming about having absolutely nothing on my calendar.
Turns out I might need to learn how to have absolutely nothing on my calendar.
“Can we discuss how many people told me my business idea was AMAZING?”
WHAT HELPEDAsking potential customers what they’d actually pay for instead of whether they like my idea. Fewer compliments. Much better information.
Can we discuss the number of people who have told me my business idea is AMAZING?
Because it is a lot of people.
Do you know how many have purchased the thing?
Three.
One is my sister.
I spent four months on the name, the website, the logo, and what I can only describe as an unhealthy relationship with Canva.
I had a launch party. There were cupcakes.
People said things like, "This is so needed!" and "You're going to crush it!"
Turns out compliments and customers are two different things.
I'm not giving up. But I have stopped asking people whether they like the idea. Everyone likes the idea. It's free to like an idea.
Now I'm asking what they'd actually pay for and why.
The answers have been significantly less enthusiastic.
Unfortunately, also significantly more useful.
“I’m almost embarrassed to admit this, but I kind of want a boss again.”
WHAT HELPEDTalking honestly to people who returned to corporate jobs after running businesses. Turns out there’s no entrepreneurship police coming to arrest me.
I'm almost embarrassed to admit this, but I kind of want a boss again.
There. Said it.
I left corporate because I wanted autonomy. No politics. No pointless meetings. Nobody telling me how to do my job.
And I got all of that.
I also got bookkeeping, sales calls, chasing invoices, doing my own tech support, and spending an unsettling amount of time alone in my house.
Last week a friend complained about her company paying for a team retreat, and I almost said, "Oh my God, that sounds amazing."
Who am I?
I still like the business I've built. I'm proud of it, actually.
But I miss having people around. I miss being part of something bigger. And yes, I miss knowing how much money is coming in next month.
Haven't decided what I'm doing yet.
Mostly trying to get comfortable with the idea that I might want something different from what I wanted two years ago.
No matching stories. A rare moment of clarity. Try another filter.
Your story stays yours. Nothing gets published without review and permission.
Then we became beginners again. How exciting. How rude.
We're Mel and Francesca. We spent years in corporate jobs, left to build Your Work Friends, and found out that being great at your old job doesn't come with instructions for starting something new.
We made this club because it turns out there's a whole lot of us in the messy middle. We're putting the things we learned the hard way in one place, alongside the lessons other people want to pass on. You don't have to be an entrepreneur. You don't need an inspiring ending. You can just be here.
Meet Your Work Friends ↗No tip jar. No paid membership. No merch (yet—we love good swag). If this place helps, the best thing you can do is send it to somebody who could use it. That's how the club gets bigger.
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