The Kids Are Alright - The Ampersand October 2025

The Ampersand Unplugged brings you an audio version of our October 2025 edition of The Ampersand, read aloud by the author. In this edition, Adam reflects on what it means to navigate the start of a career—and what the rest of us can learn from watching the next generation figure it out.

On the surface, this edition is about early-career twenty-somethings showing up at his office looking for direction. But really, it's about all of us—how we think about careers, progress, and what it means to be "on track." He makes the case that your 20s and 30s aren't about mastery; they're about experimentation. And that what looks like drifting is often just development that doesn't photograph well on a resume. 

You can find the full written blog on our website here. 

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Transcript

SPEAKER_00 0:01

Okay. Welcome to the next edition of the Ampersand Unplugged Podcast. I continue to be in our recording studio solo while I anxiously await the return of my partner in crime, Ciara Tyler, the um the brain child behind uh this podcast. And uh this is like a season of reruns. You get you get me solo uh fireside readings of uh Ampersand newsletter posts. Um fun fact, at the time that I'm actually recording this, which is our uh October 2025 post, I am uh pulling my hair out writing the May 2026 post, which happens to be edition number 200, um, which is quite a milestone. Um, so you'll get to listen to that one soon enough. But for now, um, I just want to set a bit of context um because this one uh entitled The Kids Are All Right, um it didn't come out of nowhere. Uh the headline alone probably gives you a bit of a sense of where this is going, but not entirely. Because on the surface, uh, this one is about younger people, call it the next generation, call it uh early career professionals, um, people trying to figure things out in their 20s and 30s. But really, it's it's not just about them, it's about all of us. It's about how we think about careers, uh, progress, and what it means to be quote, on track, close quote, or maybe more accurately, off track. Uh, and I'll tell you where this one came from. Uh, over the past few years, and I think anyone who spends time hiring, leading, or even just observing the workplace would say the same, you start to notice a shift. Uh the old linear model of a career, you know, go to school, get the job, climb the ladder, rinse, repeat, it just doesn't quite hold the way it used to. And instead, what you see is something a little messier, a little less predictable, people zigging and zagging, trying things, leaving things, questioning things. You know, the old uh 25-year service pin or gold watch or whatever, that just doesn't that just doesn't exist. So depending on your vintage, that can either feel like chaos or progress. And what struck me and what really sits at the heart of this piece is that we're often judging that newer path using older standards. We look at someone who's 28 or 32 or even 35, and we ask, why aren't they further along? Why don't they have it figured out yet? Why all the movement? And the counterpoint, and you'll hear this in the piece, is maybe they're doing it exactly right. Maybe that period of exploration, recalibration, and yes, even a bit of uncertainty isn't a bug in the system, it is the system. In fact, uh, one of the lines that stuck with me as I was writing this one, and honestly, I think it captures the whole thing, is the idea that your 20s, and I'd argue your 30s too, aren't about mastery, they're about experimentation. And that's a bit of a reframing because if that's true, then a lot of what we might perceive as drifting is actually development. It just doesn't look neat on a resume. Now, the other layer to this, and I think this is where it becomes relevant for leaders, for hiring managers, for anyone building teams, is okay, what do we do with that? Do we resist it? Try to force people back into the old model, or do we recognize that the world has changed, expectations have changed, and maybe the best talent doesn't follow a straight line anymore. Because if you believe the latter, and I increasingly do, then it changes how you evaluate people, it changes what you value, it changes how you hire, you start looking less for the perfectly packaged linear career and more for curiosity, adaptability, and judgment. And maybe, just maybe, you start to relax a bit about your own path too. Because the truth is, very few of us, if we're being honest, drew it up exactly the way it played out. So that's the backdrop for this one. It's a bit reflective, a bit observational, maybe a little provocative in spots, but ultimately it's an attempt to make sense of something we're all seeing in real time. And as always, with these, it's less about having the answer and more about asking a better question. So, with that, here's the kids are all right. Dear friends and colleagues, lately I've been spending more time talking with other people's kids than my own. That's not because mine need less of me, though they do, but because many of my friends and clients are, like me, in their mid to late 50s, which means their kids are entering that post-university quarter life existential. Who am I and what am I doing with my life phase? And like the neighborhood bartender, who's heard it all before, your local recruiter is as good as anyone to talk to your kids when it comes to existential career angst, goes the logic. I recognize the look when it walks into my office, hopeful, curious, politely anxious. The my mom and dad said you might be able to help look, as though the LinkedIn open to opportunities green circle were orbiting above their head like a pulsating halo. To be clear, we are a retained executive search firm. That means organizations hire us to find talent, usually senior executives, closer to the end than the beginning of their careers. We are not a placement agency, we don't work for individuals looking for a job, we work for the companies doing the hiring. And yet, when one of these 20-somethings finds their way into my office, usually on the strength of a request from a cherished friend or client, I almost always say yes to the meeting. I am certain that in another life I lived in a house full of cats. I take these meetings not because it's part of our business model, not because it pays the bills, but because I remember what it felt like to be in their shoes. And because I find myself having these same conversations around my own kitchen table with my own kids. One of them, 24, has begun her post-university life, working a real job whilst paying real rent. Another, 21, navigating the dual path of pursuing a business degree while also running his own small business. The third, 18, is taking a gap year to travel the world and learn life's lessons in hostels and train stations rather than classrooms and textbooks. Watching them and others like them, I'm reminded that there's no single right way forward. Only the courage to take the next step. And if I can help others along the way, that's payment enough. If the midlife crisis is the domain of my generation, convertibles, crypto, and half calf cappuccinos, the quarter life crisis is its less annoying younger sibling. It tends to strike in the mid-20s to early 30s, that moment when the novelty of independence wears off and the real world sets in. It looks like this. You've graduated, maybe even worked a job or two. You thought you'd have it figured out by now. Instead, you're restless, second guessing, scrolling LinkedIn and Instagram comparing yourself to peers who all seem to be crushing it while you're quietly panicking that you've made a wrong turn. The symptoms, feeling stuck in a job you don't like but afraid to leave, romanticizing alternative lives, grad school, moving abroad, freelancing, envy mixed with dread when friends land promotions or post about their incredible new opportunity. And the triggers are almost universal. First, job disappointment, the fear of choosing the wrong path, the mismatch of being overeducated but underexperienced, and the crushing cultural narrative that by 30 you're supposed to quote arrive. Spoiler alert, I founded my firm, the OG Pikarski N Co. when I was 39. Everything up until then, which only made sense looking backwards and not in the moment, was a natural step to the next one. Some forward, some to the side, others still backwards. It's not a race, it isn't linear, and worrying what others think is wasted energy. So that's the quarterlife crisis. And lately it's been walking into my office with greater regularity. In just the past few weeks, I've sat across from the daughter of a home builder, an anthropology undergrad, whip smart, trying to turn her love of people and place into something purposeful. The son of a retired lawyer, earnest and articulate, just back from time abroad and wrestling with whether to double down on law or leave it altogether. The child of a geologist, determined to carve a career not out of rocks, but out of impact. The daughter of a retired investment banker, global marketing experience under her belt, looking for a way to return to Calgary after a long stint in Europe. And just the other day, a philosophy major wondering how to translate Plato into a paycheck. Jesus, I'm not a magician. Point is different stories, same crisis. To each, I offer the same disclaimer. My advice is worth exactly what you're paying for it, which is nothing. But I'll try to leave you with something useful. And here's what I usually say. My generation often chased the money first, hoped we were good at the job second, and for bonus points, crossed our fingers that we'd end up loving it. Okay, liking it. That's a tough way to build a career. So turn it around. First figure out what you love. Is it people, process, ideas, impact? Then research the industries that need those things. Then the companies that do those things. Have your quarter life crisis now. Do the heavy lifting early so you don't have to later. And don't fall into the trap of thinking there's only one respectable path. For decades, the default setting was finish high school, go to university, get a real job, collect your 25-year service pin, retire, die. But that conveyor belt isn't the only way forward, and for many, it's no longer the best. The trades, for example, are starved for talent and offer rewarding, well-paid entrepreneurial careers without the six-figure tuition bill and crippling student debt. Likewise, travel, apprenticeships, community service, or starting something small on your own can teach lessons that no lecture hall ever will. University can still be wonderful, of course, but it's not the only stamp of legitimacy. The real question isn't what's the right path, but rather what's the right path for me right now? And in the end, goes the speech, once you've found what you love, the rest is relatively simple. If you love it, you're more likely to get good at it. And if you're good at it, the market will reward you. Passion first, paycheck second. Not exactly Harvard Business Review, but it's all I got. Besides, I only went to Tufts. I think these conversations matter, not just for this next generation, but for me. They remind me how long a career really is. 40 plus years. The 20s, and I'd submit the 30s too, aren't about mastery. They're about exploration. They're about learning, experimenting, failing, and then recalibrating. I know this can sound a bit Pollyanna. There are bills to pay, I get it. But whereas my generation seemed to be in such a rush from high school to university to a job job, chasing the next promotion, the next title, the next paycheck, this younger cohort reminds me that curiosity and courage are just as important as career milestones. They're willing to pause, to pivot, to ask uncomfortable questions. And if you take the time to explore, stumble, and recalibrate along the way, you're far more likely to end up somewhere worth being, not just someone worth hiring. As Socrates put it, an unexamined life is not worth living. They also remind me how different this generation is from ours. They care about things we never considered at their age purpose, balance, impact. They're values first in a way that's both refreshing and at times challenging. And then there's the AI factor. For them, artificial intelligence isn't an abstract headline, it's the water they swim in. They're the first cohort to enter the workforce fully aware that many of the jobs they trained for may morph, shrink, or vanish before they even settle into them. At once, AI is their greatest tool and their greatest threat, fuel for both curiosity and anxiety. They don't panic about it the way older generations might. Instead, they ask how to surf the wave rather than try to stop it. Yes, sometimes they ghost a follow-up email or over index on boundaries, but their curiosity, courage, and pragmatism are undeniable. In our business, we talk a lot about the long game. Sure, there's a transactional and highly practical way to run a search firm, or any business for that matter. Measure inputs, tally outputs, sweat each month, each quarter, and move on. But the only game worth playing is the long one. Meeting with these up and comers, even though it's not in the mandate and not readily evident in the PL is part of that. It's a form of stewardship, of investing in people before they become placements, of doing what's right, not just what's billable. Less altruistically, they are tomorrow's feedstock because when we take the time to invest in people, we're really investing in the future, theirs and ours. Selfishly, these meetings are good for me too. They keep me connected to the next generation. Even with three kids of my own, it's striking how a message from a coach, teacher, or someone outside the family often lands more than the same words from mom or dad. It reminds me of the uncertainty and the possibility at the start of a career, and it keeps me humble. They also have to listen to me, or at least they do a really good job of pretending to. I'll try to keep saying yes when the kids of clients come knocking. Not because I have a job to hand them, but because I have a chair, a coffee, and half an hour. And maybe, just maybe a breadcrumb of perspective and the occasional stray nugget of wisdom. That said, what we really need are more searches, not a parade of green halo twenty somethings through our doors. So if you're tempted to send your son or daughter my way, perhaps just forward them this instead. Because despite the anxiety and the existential angst, despite the quarter life crisis and the specter of AI, I'm convinced of one thing that the kids are alright. In fact, they might just teach the rest of us how to navigate the future and remind us to keep learning along the way regards.