Bree Stilwell

Kevin and I came together in the comments section of Rocco Pendola’s excellent piece, Why Don’t We Talk Much About What It Feels Like At Midlife? Along with other commenters, the topic hits for us GenXers, and with particular sensitivity exactly NOW. Rocco didn’t ultimately answer his own question, nor does it seem he intended to, but he really did drive the point home. Is anyone actually trying to figure this out? Why aren’t we really hashing the details on this massive transition, with each other and/or ourselves?

I’ve seen and read my fair share of griping and lamenting, and encouragement to embrace the emotions behind the griping and lamenting, as well as plenty of advice on how to hack, self-care and reconnect our way past this series of pivot points, but it all falls a little flat from the communal standpoint of the experience. We’re an entire generation of humans going through this thing together, and yet, the majority of us still feel adrift. Adrift in a very GenX, are-we-actually-slackers kind of way.

SO. I reached out to Kevin, pretty hot about it all, and he generously agreed to indulge the following conversation. We honestly could’ve kept going for months vs. the weeks we shared on it, and both hope you get as much from it as we did.

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BREE STILWELL Kevin, Hi!

I’m so excited to get this conversation going, particularly now being on the other side of our six year-old’s birthday month. Ooof. Brutal.

Your comment on Rocco’s piece certainly propped the door open for more conversation, from which I quickly snatched the bait. This issue is top of mind in my work as a personal development coach, as it’s very nearly omnipresent throughout my entire client roster. It’s deep, wide and turbulent, and in my fiftieth year, I’m in the throes of it myself.

So, from your particular perspective, what really fed your growing curiosity around Rocco’s question?

KEVIN ALEXANDER Thanks for having me!

The easy answer is that it’s at the top of my mind. I’ll be 49 soon; for better or worse, I’m in the back half of this lifetime. I tend to overthink even little things, so I’m definitely doing it with a topic as weighted as this. 

Zooming out a little bit, I noticed a lot of people my/our age mentioning that no one was talking about it, which left me wondering why. If everyone is talking about how no one is talking about it, it’s clearly something we’re collectively grappling with– we’re just not talking about it with each other.

Are we following our parents’ example of keeping up appearances? Or is it a GenX trait? We’re notoriously independent, and the idea of an 8-year-old raising themselves is more than just a meme. 

But I also think we thought we were gonna change the world. It was going to be us throwing the proverbial bricks through the windows of what marriage, family, and careers looked like.

We were going to reach great heights and reshape society along the way. And in a lot of ways, we have. But in a lot of ways, we haven’t. But it also depends on what barometer you’re using. It’s hard to reshape the future when you’re constantly comparing backward. Maybe we’re grieving that opportunity lost a little bit. 

To a person, we’re also at an age where our mortality is in our faces. 

• We’ve been through “wedding season,” “divorce season,” and now are starting “friend had a heart attack” season. 

• For those of us who started families, we’re either close to being empty nesters again– or already there–which means returning to oneself after an 18-year hiatus. More Kevin, less dad. What happens when you don’t recognize that person? 

• Elder care: Many of us are also responsible for caring for our parents–or at least managing some aspect of their lives. This is another very real sign that time is marching on.

So you’ve got all these things swirling around in your life, but maybe with a mind that still feels like it’s 22. It’s an incredible dissonance. 

In my case, I’ve made the joke that, in my mind, I’m 18; my license says I’m 48, and my knees/shoulders feel 78. All of these are true and all of them conflict with one another. 

Short story long, maybe it’s something we all want to talk about, but there are so many moving parts, we don’t know where to start? Maybe it’s too tough. We love wearing our generational identity on our (collective) sleeve, but maybe not all the (collective) clerical work that comes with it. 

STILWELL Kevin, you’re giving voice to what literally millions of us are feeling (out of 65M GenXers in total, by current estimates), and I’m counting myself among them.

We can all agree that every generation of humans have had their own unique challenges, and we’re certainly not the first nor last population seemingly unable or unwilling to discuss it. 

We’re not exactly repressive, though, are we? And in fact, much of what makes us (ironically, of course) the ‘slacker generation’ is having railed against this very thing we saw in our parents and grandparents, the ‘put up and shut up’ mentality that, along with the independence forced on us as latch key kids, fed into the level of self-sufficiency that has defined us.

Many of us saw the defeat in our parents’ eyes, those who tried so hard to change it all through real rebellion but ultimately had to bite the bullet they attempted to bury. Their communes became suburbs, their art, commercial, their quests, quieter.

And so it went with us, to your point about thinking we’d change the world and… here we are. So much is so much more bonkers than we imagined.

I’ve been both shocked and not at all at how many of my clients are in the same feels. In their late 40s-early 50s, they’ve come to this arrival of sorts, which by many standards can pretty easily be defined as a ‘mid-life crisis’. They rejected the traditional path, worked extra fucking hard to pave their own way to get to XYZ and then realized XYZ sucks in a lot of ways.

It feels a little like they/we ended up actually listening to our parents, about settling down and in, being practical about it all, and then ultimately feeling like we allowed our dreams to be co-opted by capitalism. 

We’ve got more entrepreneurs than any other generation prior. We’ve gone our own way, proudly and with what many are claiming as our collective ‘stealth power,’ but/and/also, our independence is working against us a little at this point, encouraging the corrosive effects of our individualism–lack of perspective, support, resource.

It’s like we embrace diversity and are all in for the common good, but we can’t fucking ask for help. Seems it all got real heavy, real fast. We’re the leaders, the caregivers, soon to be the cared-for, and we’re looking at each other like we just got caught in the adult section at Blockbuster. What’s that all about??

ALEXANDER I wonder how much of that is an insistence on going it alone or a little bit of shame that things aren’t working out how we’d hoped (and frankly, been promised). It’s easy to get both caught up in the day-to-day and become resigned to it all. 

I also wonder how much of a role technology has played. We’ve all read plenty about the death of the shared experience, and a lot of us are terminally online. We don’t sit around playing records together; we listen to music via AirPods. We don’t go to movies; we watch Netflix. 

Heck, even at Blockbuster, you at least had a shot at running into someone from the neighborhood!

So we have:

• Grown used to seeking info online

• Some wariness about talking to anyone (doubly so if you’re a guy)

• And even if you did want to talk, who you gonna ask? Your friend from HS, whose entire feed is filled with political posts? The neighbor whose name you might not even know? A coworker?

All of that for a generation forged in independence–no wonder we’re stuck!

EDIT: After writing this, I’ve been thinking about how we (collectively) talked a lot about “needs” and “wants” but defaulted to “shoulds.”

“I want to change the world.”

“ I want to travel.”

“ I don’t want to be boxed into the same choices my mom/dad had.”

“ I need (XXX).”

All well and good. And some of us did just that. But we also really bought into the idea that we should get a “good” job. We should want to upgrade cars every few years. We should want a nice house in the suburbs. We should want to meet a partner and get married. We should have 2.5 kids. We should stay close to our parents & take care of them later in life… 

…just like the generations before us did.

I’m sure we’ll veer off into the topic of careers at some point, but it’s been fascinating for me to watch the attitudes around career & work rapidly shift at my job since COVID. It would be easy to think our little station is an outlier, but I don’t think it is. I think it’s an early signal of a larger tectonic shift. 

STILWELL Ooooo, Kevin – say more!

You’re literally speaking my language.

First, picking up what you’re laying down about technology not doing us any favors in the common experience of all this. I agree completely with what you’re poking at here, which is the irony of being more ‘connected’ than ever before (via our endless and tireless online interaction) while lacking the trust forged via deeper attachments, completely crucial for having those tough and vulnerable conversations.

We wonder why we’re feeling stuck at our job and we google it. Google shows us a billion and one articles, newsletters, posts, threads, ads, you name it, about it being a solvable thing. We read a few (or way too fucking many) of them, feel validated and maybe even a little empowered, try this or that hack and then end up in the same exact spot.

I think you’re absolutely right, that we’re getting fooled into thinking we’re having this common experience, but it’s really a one-way conversation. We’re telling each other we’ve got this stuff going on (through our various platform personas), and we’re listening to each other through those same channels.

But it’s like having a conversation via semaphore. It’s all just signaling from the shore.

Next, the shoulds. 

As Substack hall-of-famer, David Roberts recently wrote: ‘Is the word “should” the most seemingly innocent and thus the most insidious word in the English language?’ If it were possible to primal scream in agreement, I would have.

Shoulds are inherently judgmental. They’re issued via opinion, on what’s obligatory and/or correct. Insidious indeed, and so often what we find ourselves defaulting to when the going gets rough and real. 

Going against the grain was harder than we thought, and comfort is, well… comforting.

Okay, there’s all that.

And also, what you’re seeing in career and work shifts at your ‘little station’… what’s happening that you think might be (speaking of signaling) predicting some bigger moves?

ALEXANDER Those billion and one articles ( too fucking many articles, really) are a vicious cocktail. They’re exacerbating our sense of FOMO, but also giving us a dizzying array of choices. So much so that we lock up. And that’s before we even consciously recognize our innate desires (the need for security, to take care of our families, etc.) and/or the effect that generations of advertising and social conditioning have had on us. 

There are memes that have a picture of a remote cabin and say something like, “You get $100k if you stay here for a month with no internet,” and almost every response is something like “where do I sign up?” Part of that touches on what you and I are talking about– the need to reset and escape the choices we’ve made. But some of it’s a surface reaction to just wanting to escape the nonstop digital noise in our lives. If that switch is turned off, we wouldn’t be reminded every 4 seconds that people are out there living their best lives while we’re pulling extra shifts to pay for our mother-in-law’s car to get fixed or new cleats for our kid, or whatever. 

As for wants vs. shoulds: Some of that is slowly fading, but it’s resilient. My mom wanted to do art. Today the easy answer might be to set up an Etsy, or teach, or whatever. In the 70s, that just wasn’t something people like her did. She wanted to travel, but the pull of her family kept her close to home. Left unchecked, it becomes an anchor. In fact, she never left the Portland metro area (to live) until her mid-70s, and even that wasn’t until both my grandmother and my stepdad had passed away. Her half-sister wanted to be a flight attendant & see the world. That same anchor meant years of “settling” for being a waitress and now a school bus driver. Neither of these are uncommon stories. Not sure if you saw it, but Rocco wrote a bit about that a while back. 

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I think we’ve been sitting on a volcano for awhile now, and COVID was the earthquake that started setting everything off. If nothing else, it was a wake-up call that life’s short. It also laid bare how (ultimately) meaningless many careers are. 

Yes, work has value, but sitting at home on Zoom calls all day is a great way to see how much or how little one’s work matters in the grand scheme of things… and how irrelevant being in an office is (depending on vocation, of course). 

Sitting at home forced many people to face what they’d been running from. When you’ve made all the sourdough and binged all the Tiger King, the only thing left is your thoughts, right? So now we have people slowly recalibrating everything.

What matters to me? How am I going to spend this one wild & precious life? Do I really want to drive 2 hours to sit in a cubicle and listen to Todd rattle off PowerPoint Decks? 

This could’ve been an email!

In my case, I work for an airline, and despite the CARES ACT protecting our pay, they found a loophole in the language that, at a minimum, violated the spirit of the legislation. The end run was a 25% pay cut in the form of an hour cut. For me, that meant a 4-day work week (rad!), but only 30 hours a week (not awesome). 

But a funny thing happened; I realized I didn’t need nearly as much money to get by as I thought. With the world slowed down, I had time to focus on things I enjoyed… and had an extra day a week to do them!

My job is seniority-based, and the goal had always been to get a 40-hour line, and then one with good days off. That’s just how it was. But people around me started having the same realization(s), and those 40-hour lines were going unbid longer and longer. 

People were intentionally choosing less hours and more of anything else. Lines that pre-COVID would’ve been snatched up right away were falling to the bottom. People were also using more of their paid time off, even if it was just in hour increments, and giving away their shifts. Those patterns are (more or less) the norm today.

People are actively choosing a quality of life over a quantity of hours.

STILWELL What’s additionally super interesting about all this is how we GenXers seem to be in a uniquely precarious, and maybe pivotal, position. 

You’re so right about the post-COVID ripples, and I’ve seen it big time with my clients. It was a massive shakeup in so many ways, and I’d argue, and with your perspective in mind, that those of us in the prime of our working lives, in the ‘middle age’ of our careers, have been distinctly rattled.

What we thought we wanted, what we spent so many years grinding away at (and in so many cases, should-ing ourselves into), was brought into disturbing relief when the context of it all completely changed. Almost like those 3D optical illusion pictures that started blowing our minds in high school (guess who just Googled and guess what they’re called… autostereograms. I sure as heck didn’t know); you’re looking at one thing, can’t imagine seeing anything else, give in to the peer pressure assuring you to keep crossing your eyes and you’ll see it, and there it is. SNAFU.

So, not to make it all about us, but WE are the point of this conversation… this generation appears to be both particularly hobbled and particularly queued up. We came into our individuation as misfit rebels of sorts, wanting to reject the status quo but in ways very different of course from how our hippie (or square) parents went about it. We’ve got the muster, and while it’s lain dormant for some time (disillusioned I think by a whole smattering of cultural challenges and disappointments, but that’s another conversation entirely), COVID really woke our sleepy asses up.

OMG. We’re here. We’re turning the corner and this is NOT what we expected to see.

We’ve kept our heads down, owning both our work ethics and our individuality somehow, while maybe even waiting for the boat to swing around.

But it’s time to string our rafts together, right?? Can we do this?

I’m working through it all myself in real time, as I type this, having left behind a comfortably successful (but soul-cannibalizing) career to have a kid in 2018 and at age 41. Doing so right at the midlife starting line felt pretty natural, and then, COVID added all the exclamation points. I had to really, like really truly, assess and then reassess both my past choices and current ones, as the world ground to a halt–it was a forced reckoning for humankind, and/also, supercharged for us already in the throes of a midlife audit. I changed everything about my life because of it, and am now here, writing with you and coaching others through similar terrain.

I posit again then, sir, that we GenXers might just have a crack at this whole change-the-world business yet. What do you think?

ALEXANDER We have a great shot at changing the world; we just need to convince ourselves (collectively) that there’s still time to do it–and that it’ll improve our lives. We can reframe our narrative. We don’t have to be content with lament and memes about drinking from garden hoses. We can job hop. We don’t have to live in a house with a white picket fence in the suburbs. We don’t have to drive minivans. Or wear cargo shorts ( I mean, I do, but still). 

We can take sabbaticals. We can paint. We can start a family in our 40s. We can retire in our 50s…or keep going if we want. 

We were really good at breaking through the constraints of societal norms as kids. We need to do that again. And the first step is to remind ourselves that we’re not alone. Easier said than done, of course, and ironically, we’ll need to use some of the very vehicles that were weaponized against us (politics, social media, advertising) to make it happen. It will be a whisper first –an FB post here, an NYT article there… First movers always have the steepest climb, but as things gain momentum, it will be easier for others to jump on board, and it’ll hit critical mass.

STILWELL If this isn’t a call to action, I need to spend more time on the concept.

From my perspective, both personally and as a coach, the breadcrumbs are everywhere right now. We ARE feeling it, talking about it, exploring the options, jumping lines and skipping steps. And you’re so completely right about the power of the reframe, Kevin–we can still do things differently, at any moment, at any age. We just have to choose to do so.

History is not destiny.

This feels like about the right time to ask a few questions of the other VIPs joining this conversation, you, the readers!

If you’re a fellow GenXer, how does this all jive with you?

As you’ve approached middle age, have you noticed yourself/your circle slipping more into the familiar patterns of those that came before us? 

Sure seems that more and more people are actively/vocally bucking these preordained patterns. Do you know anyone doing the bucking? What actions have they taken/not taken?

What actions are you taking?

Curious too…

Any ideas on how to come together to reject our complicity in all the stuff about modern life we actually hate… and in favor of doing more that we actually love??