The Unemployable Man - EPISODE 1 (Ok Boomer)

"OK, Boomer" has become one of the easiest ways to dismiss an entire generation. 

In this opening essay of The Unemployable Man, Ray Whitaker argues that our identity isn't defined by the year we were born, but by the life we've actually lived. What begins as a look at generational labels becomes something much more personal—a reflection on decades spent keeping the peace, swallowing honest thoughts, and discovering the hidden cost of never finding your own voice.

With humor, candor, and a few unexpected detours, Ray explores aging, anxiety, therapy, friendship, family, and the quiet liberation that can come from finally speaking your truth.

Because sometimes the greatest freedom isn't being young again—it's finally becoming yourself.

The Unemployable Man is a spoken-word series by Ray Whitaker featuring original essays about work, identity, memory, mental health, creativity, culture, and the ongoing business of becoming—and laughing at—yourself.

If you enjoyed this episode, please follow the show and leave a rating or review. It helps other listeners discover The Unemployable Man.

If these stories resonate with you, I'd be grateful if you'd share them with someone who might need to hear 'em.

Transcript

SPEAKER_00 0:00

The phrase okay boomer has become the generational shot heard round the world. It's deployed mainly by Gen Z kids, those born between 1995 through 2010, and it's all over social media. Okay.

SPEAKER_01 0:39

Technically, that applies. Having been born in 1963. And as much as that seems to be the ageist epithet du jour, I can put it that way, and I just did, that phrase really does not bother me all that much. Mostly because I don't identify myself by or with the generation I came up with. Because it's weak. It's too general for my taste. It's too much of a group mentality. Because, let's say you're out in public and you're essentially holding court and you're going on and on about how your generation was the best generation. I mean, you're really driving the point home that all the folks in your age group, and you say all, you are unsupervised, latchkey kids who are always in harm's way, stranger danger, all that shit, always outdoors, climbing trees, getting hit by cars and shaking it off. Just an awesome group. One to be appreciated endlessly. You and your peers were just it. All succeeding generations better goddamn remember it. Meanwhile, not twenty feet away, there's a group of folks right around your age, behaving like complete shitheads. Drunk, inappropriate, harassing assholes. Considering what you were just talking about, do you really want to align yourself with them? Just because you're of the same generation? Do you feel a bond with those friggin' idiots? You see what I'm saying? Conversely, just because there are some folks of note in our age group or any age group, you know, who have risen to the top of the food chain, as it were, and they reflect how we feel about certain societal norms, the operative word there being certain, like folks like Bill Burr and Tom Segura, they couldn't possibly represent all that we think and feel. I mean, how could they? It's like that old saying don't judge an entire group by the actions of one or two. And though that's mostly used in a negative context, it could also work in reverse. And to stay in the comedian vein, and because I want to mention George Carlin, just because he was a thought leader, it doesn't mean that everyone in his age group were as forward-thinking as he was. I mean, far goddamn from it. And there's another reason not to feel all jazzed about aligning ourselves with the um lower hanging fruit of our age group. The lauding of our day over the ones in their formative years. And for some reason I'm doing finger quotes and nobody's around to see it. Anyway, nobody wants to hear that bullshit. We didn't. Like if some older prick around my age now, early 60s, came up to my friends back in the day and started saying, you know what, you kids, you don't know the value of hard work. You don't even know what hard work is compared to the 40s and the 50s. Just out of sheer spite, we do a shitty job. Actually, that's not true. We just patronized the shit out of this old bastard until he walked away from our general vicinity. So aligning with any group for some sort of identity is not the answer. And it's certainly not character building. So there's the whole generational alignment bit. Obviously, I say no to it. But as for getting older, it definitely does have its benefits. Because having the gift of lived experiences and by association perspective, we are gifted the right to engage a few get off my lawn moments. Cause, let's face it, if you and I are roughly around the same age, early 60s, we are officially on the other side of the mountain, as it were. We appreciated the time we came up in, and we honestly could give two shits about being perceived as older. And though it sounds like I may be contradicting myself because I'm saying we, I'm proceeding under the assumption that you also do not embrace a group mentality. And uh I was thinking the other day, I got maybe thirty years left of being vertical. And then it's off the harp class. And that being the case, I want you to think about the first forty or fifty years of your life, and how they were mostly spent trying to um you know, not colour outside the lines. Always trying to say the right thing, trying not to offend. That, without exaggeration, was active duty status and it was goddamn exhausting. You know, keeping our employers in a good mood, making sure whoever we're with feels secure and appreciated, maintaining familial harmony, though depending on the house you grew up in, that may have been damn near impossible. I can speak to that. And maintaining a kind of homeostasis with your friendships. And uh by the way, friendships to touch you one. For me, anyway. Because depending on who you call a friend, you were either attached at the hip and everything was copacetic, no problems. Or there was some unspoken one-sided competition that left you feeling diminished. And not to dive down this hole too far because I really could. Remember the end of the movie It's a Wonderful Life when George Bailey read what Clarence the Angel wrote in The Adventures of Tom Sawyer. It said Remember, George, no man is a failure who has friends. That was probably one of the shittiest messages of any movie ever. Amazing movie. Classic movie. Questionable ending. The reason being that it completely detracts from the importance of first being your own best friend. It suggests that you're nothing without friends. See? Shitty message. And in a future episode of the Unemployable Man, I will delve into that a whole lot more. The over reliance or elevation of friends in your life. Anyway, the point is, getting back to the whole active duty thing. You're pretty much walking on eggshells for decades, keeping everyone in your life in a good mood. I mean, if you're a sociopath, then this doesn't apply. You just fire away, say shit without caring, and people can just flame out, and you don't give a crap. But that's not you. At least I'm assuming it's not you. Even swallowing appropriate sarcasm. Because in my world there's no such thing as inappropriate sarcasm. Or suppressing those natural instincts and stuffing way down deep those sharp but honest things you always wanted to say. You did all those things because you just wanted to keep the peace and have a peaceful life, you know? But you do that long enough, and you are eventually presented with a bill for all that suppression. Every interaction, every agitated moment, every moment of forced diplomacy, every time you keep your mouth shut because you don't do well with confrontation, that's me. All that shit doesn't just vanish into the ether. It has to go somewhere. And that somewhere is your nervous system. All that cumulative quashing you did just to maintain harmony. It re-emerges in not so friendly ways. Ways like anxiety, heart palpitations, headaches, depression, a sense of dread that seems to come from out of nowhere. Feeling, as Niedermeyer said in Animal House, worthless and weak, you know, sleep patterns roll over the place, even something topical, like eczema, can manifest by this kind of long-held stress. And the weird part is that while all this is happening, you're not really making the connection between the two, between those years of holding everything in and what's happening to your body right now. So understandably, you head off to the doctor. You tell him or her your symptoms, you go through any number of tests, and the results come back, accompanied by a note from your primary care physician or a nurse practitioner that says, All results are normal. And you're like, Are you shitting me? And then you shoot back an email, you call, and you say, Well, that's fine, I guess, but I still feel the exact same way. So, what to do? So now you're feeling worse. Because there's nothing physiological that you can point to as the reason for you feeling crappy. And if that doctor or nurse practitioner is worth their salt, they'll tell you that all those tests, they were just to eliminate anything physically wrong before they offered up anything psychological or emotional, you know, as to why you may be feeling the way you're feeling. They may ask you if you've been experiencing any kind of stress or suffer from anxiety or depression. And that really is more of a routine follow-up question because you may have already indicated as much in your intake form as a new patient, to just check in to see if your mental health is declining for any number of reasons between then and now. And then you have this sort of weird oh yeah moment. A long delayed acknowledgement, acceptance, really, of all the things that made or is making, you feel the way you're feeling. Your father, for example, was just a four-star asshole. Your mom, she used you as her personal therapist, telling you things that no mother should ever tell her adult child, let alone the horse shit she confided in you when you're eight. And your brother? Well, he was just a dumb, drunk, and creepy bastard who had horrible hygiene. And then there's you. With the overall vibe in your house growing up being not harmonious, you escaped into your own little world. A world that your so-called friends could not understand at the time. And they made you the butt of all the jokes and torment. Not that I'm, you know, speaking from personal experience, you understand. And in this not so beautiful moment of clarity, you put together all that early childhood shit that fed into adolescence and then adulthood and discouraged you from speaking your truth or speaking up in any way, even in your marriage. You didn't feel, and to a degree, still don't feel, like you have the right to say exactly what is on your mind in the moment it needed to be said. You feel like you have no voice. So having acknowledged all that, what do you do? Well, being a little old school and just a little more than prideful. The um the thought of seeking out a psychotherapist, it seems weak. Yeah. And you think to yourself, you know what, my folks didn't do that, and their folks didn't do that. And then it dawns on you. Yeah, no shit. And they totally should have. The fact that they didn't deal with their problems and how they rained their misery all over you was not only ignorant and selfish, you immediately think about how you really don't want to repeat their pattern of being a total downer to yourself and the family that you have created. Because the last thing you want to hear from the one you love most in the world is this. From everything you've told me about your father, you're pretty much walking the same path, or something along those lines. Okay, may have taken over a half a century for you to come to this conclusion, but you have to remember some folks never do. Either because the shame is too much, or it's looked upon as weak, or you're just lazy pieces of shit, and that is a very real answer to. So by taking steps to find a therapist, one who doesn't have more problems than you do, uh, one you can trust and not feel judged by, you're showing yourself the kind of consideration no one ever showed you. And that's how it should have been from the very start. And really, it's all about having that feeling right there in your solar plexus of complete freedom. The freedom to think, feel, and say whatever the fuck you want. But with kindness and diplomacy. Can you imagine what it must feel like not to have that tense feeling right there in your gut? Not to have fear or intimidation, especially in the areas of your life that mean the most to you. It's the best thing you can do for yourself. And if I'm going to be completely forthright with you, this feature, the unemployable man, is essentially an extension of all the moments in my own life when I've essentially verbally garotted myself. And to a degree, the result of the work I've done with my own therapist. Because throughout my life, whether in letter or essay, my best mode of communication where the honesty is on full display is when I write and then record these features. And I used to think that that wasn't the way to do it, because I kept comparing myself to other folks who knew exactly what to say in the moment they wanted to say it, regardless of how harsh. I might not always appreciate the visceral tone, but the ability to let it fly like that, that's something that I just don't ever feel I could ever do. And because of that, I felt weak. But then I heard this one quote, and you've probably heard it too. Comparison is the thief of joy. And yeah, I know, there's a thousand quotes out there that are meant to inspire and all that shit. But when I heard that one, I felt this major release because it's so true. Because what's deep inside, fears, hopes, regrets, dreams, and non-cree confessions, will be on full display with the unemployable man. Because I know there are millions of folks out there, just like me, who also feel self-stifled and wish they had the balls just to let their true selves burst forth. Not in a thoughtless way, not in a mean-spirited way, but in a situation appropriate, 100% comfortable and honest way. In a way you can feel confident and proud of. Thanks for listening. I'm Ray Whitaker.