Changing Careers When You’re Middle-Aged is Hard Because You Feel Like an Idiot

It’s like playing Russian Roulette with a Nerf gun filled with mothballs, Bengay, and the voice of your mother asking if you’ve thought about going back to teaching. 🔪

The thing about changing careers when you are the same age as someone who’s Googled “what is perimenopause” at 2am is that you go from having twenty years of experience—respectable! authority! title! boss!—to having zero experience (and zero clout)—all while your hormones are throwing furniture out the window like they’re quitting their job, too.

It’s a little like losing your virginity all over again.

Oh god, remember that?

Now that’s something to fear. If gas station soda bottles came with a warning label that said,

“⚠️ Caution: May cause lifelong blistering, 18 years of unpaid Uber driving, and $300,000 in expenses, not including emotional damage…”

…I’d sooner lick the floor of a Waffle House than put one of those to my lips.

ANYWAYYYYY.

Common wisdom always tells us that mid-life career changes are hard because we’re scared of change, but like... are we? Really?

If someone showed up tomorrow with a brand-new house, a brand-new car, and a brand-new passport, I wouldn’t be scared—I’d be halfway packed. I’d be peeling out of my driveway in a robe and Crocs, waving goodbye to my old LinkedIn bio like:
“So long, Janet from HR—I’m a goat farmer in Tuscany now.”

Scared of change? No, babes. I'm scared of staying exactly the same while my soul slowly shrivels like a baby carrot in the back of the fridge.

Changing careers when you’re middle-aged is hard, not because you’re scared, but because you feel like an idiot.

🤔 How many times have you tried to just MAKE A DECISION about your future life’s direction, but can’t?

🔫 How many times have you tried to just PULL THE TRIGGER on something new, but can’t?

💫 How many times have you swirled idea after idea after idea after idea around in your head, hoping to land on THE ONE, but…can’t?

It’s like playing Russian Roulette with a Nerf gun filled with mothballs, Bengay, and the voice of your mother asking if you’ve thought about going back to teaching.

You want to reinvent yourself. You want to try something new. But every idea feels either too exhausting, too big, too unknown, too hard, too much, too late, or too “influencer-y,” and suddenly you’re spiraling into an Etsy shop that sells artisanal moss.

Changing careers in mid-life isn’t about fear. It’s about decision fatigue, existential whiplash, and the paralyzing realization that you’ll have to explain your new job to someone who still thinks “freelancer” means unemployed.

In other words, ya feel like an idiot. 🤷‍♀️

You can’t figure your own self out.

And god, what a confidence downer, am I right???

Speaking of confidence downers, you’re also acutely aware of how uncool you have become, throughout the years, and therefore trying to ‘make your mark’ in a new industry when you can hardly make it to the toilet is, well, rather daunting.

(The other day while teaching a class online I literally thought I was going to have an accident in my pants. I can just hear it now: “Millennials turn to diapers in desperate attempt to stay online.”)

Those fresh-eyed rosy glasses we all once wore are now tinged with schmutz, and franky, it’s probably mold. Because mold is everywhere when you turn 40. Suddenly, you worry about mold like you used to worry about zits. Is there mold growing in the basement? Is there mold growing in the washer? Is there mold growing on my plants? Is there mold growing on my big—now sorta hairy?!—toe?

(Also, there IS mold growing on my new neon flash plants. I am about to go rambo. Send the authorities if you never hear from me again.)

A Gutsy Escape Plan for Your Mid-Life Career Crisis 🥷 🤺 ⚔️

So, what are we to do when we’re staring down the barrel of life and it’s yelling back to us, “Go get some new jeans, granny!”

I have some ideas.