Journal of Becoming: Entry #2—Starting Over in Your 40s Isn’t Like Your 20s & 30s

Midlife resets are less “Eat, Pray, Love” and more “Stretch, Ice, Repeat”

Let’s play ball ⚾️

I grew up on Americana, high apple pie in the sky hopes, and the belief instilled in me that I could do and be anything I wanted. I did everything society said you were supposed to do to be successful: graduated from college, got a corporate job, got married, and moved to the suburbs. The American Dream.

Cue record scratch.

Fast forward 16 years, and I’m burnt out from a career I was once passionate about, burning through my savings like a firenado, and setting fire to my decade-long expat life.

Stick a fork in me, I’m charred.

Now, I don’t want to be dismissive of anyone’s experience, but when I come across articles titled “Starting Over in My 20s” or “How to Start Over in Your 30s,” I chuckle and shake my head and think to myself, oh honey, you’re just getting started.

I realize there are people older than I am who may be reading this thinking the same of me—oh honey, you’re still young! It’s not too late! Be positive!

You be positive, I’ll be realistic.

Sorry, Virginia, I don’t mean to burst your bubble, but: there is no Santa Claus, being positive will only get you so far, and sometimes it is too late.

Or at least harder.

I’ve had the pleasure (or displeasure as the case may be) of starting over in my 20s and 30s, and I can tell you, it’s a whole other ballgame when you do it in your 40s—one with more rules, less padding, and a higher risk of injury.

While starting over in your 20s and 30s can feel like an exciting adventure—think premium box seats—reinvention in mid-life can feel more like a curveball to the face.

Let’s take a look at just a few areas where pressing the reset button in your 40s and beyond can be a swing and a miss.

Swing, batter batter!

Kids

Tick-tock, ladies! That biological clock is a tickin’ and society is tapping its foot. If you’ve got the resources and want to go through all the freezing, injecting, and hormone pumping that so many women in mid-life have to endure in order to do what their younger counterparts can often pull off without a calendar, spreadsheet, and a small fortune in medical bills—by all means. But while the term “geriatric pregnancy” may be getting euphemized to “advanced maternal age,” the fact is a spade is still a spade and any pregnancy after age 35 is generally riskier.

In my late 30s, whenever the topic of kids came up, the looks I got from friends and nosy strangers went from expectant to pitying. At 36, my clock blasted so loudly I didn’t know what hit me. I fell out of bed and hurled the damn thing at the wall for trying to confuse me.

I always knew I didn’t want kids, but those of you who do can only press the snooze for so long.

Career

The cards are stacked against midlife jobseekers—especially if you’re trying to break into a new field or gain new work experience. Most internships are only for recent grads, working holiday visas are for the 30-and-under crowd, going back to school would land you in a pile of debt, and volunteering may be great when you’re still living with the rents, but now you’ve got bills to pay.

It’s cool to be a teenage barista saving money for college, but a 40 something slingin’ lattes—because they’re caught in a catch-22 of being overqualified for entry-level positions while at the same time lacking experience for higher-level roles—has to deal with society’s side eye and snarky articles like this one: 5 Reasons Your Kid Will End Up Being a 40-Year-Old Barista.

If you haven’t already established a career in your desired field over the last 20 years—including all the connections that go along with that—it is going to be exponentially harder for you to get your foot in the door, regardless of transferrable skills.

Not to mention that ageism, while illegal, still happens.

And we’re not just battling career burnout and recent grads willing to work for less, now we also have to contend with AI job displacement.

The current job market is rough. I have heard horror stories (my own included) of well-qualified, experienced golden millennials applying to hundreds of jobs over a period of years and hearing nothing but crickets.

Full outbox, empty inbox.

Dating

If you thought the job market was tough for a 40 something, try dipping your toe back into the dating pool in mid-life. It’s full of murky piss water with baggage-laden men and women and their sticky, screaming children with their own little backpacks.

What dating in midlife could potentially look like

If you’re in your 40s or older, you remember a time before dating apps, when having a profile on Match.com was considered taboo. Now, people flaunt their pages-long match list and brag about how they had a different date for breakfast, lunch, and dinner.

I get decision overwhelm at a restaurant with a menu of only five items!

Travel

It’s much more socially acceptable for a 20 something to go off galivanting around the world until they figure out what they want to do with their life, but a 40-year-old will be told by well-meaning friends and family to get their butt back home, get serious, and stop playing around. Society expects you to have your shit together by 40 and be (dun dun duuun) “settled.” Wanna travel? Save up PTO at your 9-5 and take your ten days off. Use one of those days to recover from your trip and another to catch up on work emails.

Recovery time is another factor. When I traveled in my 20s, I stayed in hostels with bunk beds and shared bathrooms and could sit in economy with my knees up to my chin, no problem.

Now? I need at least three days to recover from jet lag, preferably in an ensuite hotel room with a Tempur-Pedic mattress to soothe my aching back.

Diet and Exercise

One minute everything’s cool, everything’s fine—you’re stuffing your face with cheese, having a little sweet treat every night before bed, maybe doing a leg lift or halfhearted crunch here and there—but nothing to overexert yourself—and you’re prancing around in your bikini and slim-fitting tube dresses like you’re Forever 21 personified. You might get away with this well into your 30s and then…

BAM!

On your 40th birthday you wake up with a tire of fat that could rival Michelin around what was once your abs, and you won’t be able to even look at a piece of bread without growing a pair of fleshy wings on your back. Now, I want to acknowledge all of you out there who have always eaten healthily and were diligent about exercise. You may have done everything right and therefore never had to do a complete overhaul and reset of your health habits.

But guess what, doll? Michelin’s comin’ for you too.

Hormones are a bitch.

Say hello to your new midlife bod

Is it really all doom and gloom?

Look, I know this may come off as cynical, and this space is supposed to be all about resilience and empowerment—but my Substack is titled “Morgan in Wanderland”, not “Morgan in La La Land”, so I’m not gonna sugar coat anything.

I was recently discussing menopause with a friend who is in her mid-50s, and after listening to her stories in wide-eyed terror, I asked her, “So…is there really nothing to look forward to in midlife?” She paused for such an inordinate length of time that I thought petit mal seizures were another thing I’d have to add to the already-long list of menopause symptoms.

In all seriousness, no, I don’t think it’s all downhill from here. But starting over in your 40s is as much about reinvention as it is about reconciliation. Coming to terms with your past choices, your current limitations—and yes, whatever future possibilities remain—is all part of the game.