Crossroads, Chaos, and the “Shoulds” That Almost Broke Me

How I Survived the Grind of My 30s & 40s and the 7 Rules I’d Hand Myself Today

Nov 23, 2025

I started working when I was 14. Lied my way into that first job, not out of desperation, but because I wanted it. From then on, it was jobs, then career, then identity. I worked hard, I built something I’m proud of, and looking back now, some of my choices feel brilliant… others feel like survival band-aids.

The years spent at deep crossroads - especially in my 30s and 40s - were brutal!

One in particular stands out: I was pregnant with my third son, just shy of 40, which stamped me with that charming “geriatric pregnancy” label doctors loved to slap in giant red letters on your file back then. No digital charting - just a fat, ugly folder screaming at me every appointment: OLD.

I was working for a startup. My boss quit. Despite the CEO’s pep talks and the offers of “we’ll figure this out together, here’s a bigger title, here’s more money, and fuck, we’ll build you a daycare room for your kids in our office,” I knew I couldn’t hold it all. So I jumped and took a job at a bigger company with fewer responsibilities, a lower title, and less pay.

Why? I wanted to chill the fuck out. To get through my “old-lady” pregnancy, to actually take a low-pressure maternity leave, to breathe a little with three kids at home. And yeah, I knew I’d be restless in 18 months. I was. But guess what? That job did exactly what I needed it to do.

It was my parking lot. A place to idle, to pause, to just survive. And I don’t regret it for one damn second.

Because here’s the truth: Those. Years. Were. Hell.

Cortisol was my fuel. Sleep was broken, stolen in slivers that never added up. The demands at home and work were crushing. Honestly, I thought that was just how life was supposed to feel: chaotic, relentless, exhausting.

And I know I wasn’t alone. My friends and sisters now in their 30s and 40s are deep in it — running on adrenaline, juggling kids (for those who have them), work, aging parents, and sick days that never come at the right time.

And when the pandemic hit, it only poured gasoline on the fire. Entire cohorts of women lost years of their lives to just “keeping up.”

Then the economy shifted. Layoffs. Recession warnings. Work from home… until the back-to-office mandates rolled in. And now? Companies acting like we should be grateful to have jobs — as if gratitude pays the mortgage.

Another crossroads. Another question: What path do I want?

At some point, many of us feel like we have to choose: If you’re in IT, do you climb toward CIO? If you’re in marketing like me, do you sprint for CMO? If you’re in law, do you grind for partner? If you’re a teacher, do you chase principal? And even if you can… do you actually want that?

Because every choice comes with tradeoffs: a bigger title might mean missing the moments that matter - your kids’ soccer games, your friends’ milestones, your own downtime… hell, your own life. Money and power are tempting, but damn, so is peace of mind.

7 Things I Wish I’d Heard About Work & Career

Now that I’m on the other side of those years, here’s what I’d tell my 30- and 40-something self, and what I’ll tell any woman currently in the trenches, running on fumes, staring down those crossroads:

Drop the damn stick.
Stop beating yourself with “shoulds.” You don’t have to chase every title or prove every ounce of worth in every room all the time.
Get clear on your why.
Climbing the ladder is only worth it if you actually want the view at the top. Ask yourself if it’s ambition or autopilot.
Survival choices are valid choices.
Taking the “parking lot job,” stepping down, or slowing the pace isn’t failure. It’s strategy.
Your path isn’t permanent.
One job, one boss, one season doesn’t lock your future. Careers bend, stall, and restart, and you’ll have more shots than you think.
Money is power, not shame.
Ask for it. Negotiate it. Bank it. Don’t apologize for wanting it. Every dollar is freedom for your future self.
Delegate like a boss.
At work and at home, it’s not just the tasks. It’s also the mental load. The nonstop, invisible labor of remembering, managing, anticipating, fixing. You’re not weaker for sharing it; you’re stronger for refusing to drown in it.
Power isn’t always a promotion.
Sometimes power is choosing peace. Sometimes it’s saying no. Sometimes it’s walking away from the “dream job” that’s actually a nightmare.

How to Get Clearer Now - A Midlife Reality Crash Course

Women in their 30s and 40s don’t need another TED Talk or a 400-page “lean in” manual. You need clarity you can grab in the middle of a school drop-off, a Zoom call, or the five minutes before your next meeting. Here’s how I’d frame it:

The “Why Test.”
Before you say yes to another job, project, or promotion, ask: Why do I want this? If your first answer is “because I should,” that’s not a why, that’s a warning.
The “Energy Audit.”
Look at your week. What tasks drain you? What actually fuels you? If 90% of your work is drain and only 10% fuels, you’ve got clarity: something needs to shift.
The “Money Mirror.”
Ask yourself: Am I being paid what I’m worth or just what they can get away with? If the answer stings, don’t shove it down. Let it light something up. That frustration is fuel so use it to plan your pivot, start your next thing, or quietly build the exit strategy you’ll thank yourself for later. Because it’s always smarter to start creating options while you’re still in the current chapter.

The “Would I Choose This Again?” Check.
Imagine today’s job/opportunity landed on your lap for the first time. Would you still take it, knowing what you know now? If the answer is no, you’ve got work to do.

Final Word

Your career isn’t a one-lane highway. It’s a freeway with exits, detours, and places to pull over and breathe. You don’t owe anyone a straight climb to the top if that’s not what you want. You owe yourself a life, not just a job.

PS: If you want more midlife real talk, you’re in the right place. This is the conversation I wish someone had with me in my 30s and 40s. If you’re fueled by cortisol, stuck at a career crossroads, or just tired of carrying the damn stick, you don’t have to do it alone.

Subscribe to the Real Girls Guide to Over 55 crew, where we trade stories, share the hacks (and the mess), and call BS on all the “shoulds.” It’s free, it’s fun, and it’s OUR space to get real.