Conversations that start with “back in my day…” or “you all had it easy…” often devolve into a “competition of pain” between generations. This struggle over who had it worse – whether facing job insecurity, historic student debt, or climate anxiety – is a competition where nobody wins.
Each generation’s challenges are unique and valid. Boomers and Gen Xers navigated recessions with little focus on workplace mental health, while Millennials entered the workforce with unprecedented student debt, and Gen Z faces global instability and digital burnout. Comparing these struggles isn’t productive because shared struggle doesn’t mean equal struggle.
The key is to shift the conversation from “who had it worse?” to “how are we experiencing this moment differently?” By leading with empathy and curiosity about what others are carrying, teams can move beyond unproductive conflict and appreciate the diverse perspectives each generation brings to the table.
I’ve heard so many statements, like back in my day we worked for, uh, for example, half the pay that, that you work for now, or, you know, on the, on the flip side of that conversation, the, you all had it easy how, you know, housing was more affordable. I know housing’s a huge conversation with, among uh Gen Zs and millennials right now. And I don’t think that being a part of a discussion and this competition of pain, so when we consider the ‘who had it worst’ conversation, it really is when you break it down, it’s a competition of pain between different generations and I don’t think anybody wins in that case.
I think that instead we really should start to focus on validating that each generation is going to be different no matter what. Right? When we talk about cultural competency, etc., respect in the workplace, and it’s not necessarily a terrible thing.
So if we reframe the way that we think about things, for example, if we’re talking about boomers and Gen Xers, and, you know, they were faced with some serious job insecurity back in the day during the recessions. And, often they weren’t necessarily thinking about mental health and wellness and access to that mm-hmm in the workplace. Whereas millennials, we have entered the workforce at a time where we were entering the workforce and we, I believe that it’s been proven that millennials have the most amount of student debt. Uh, yeah. So I see you shaking your head Dom. Yeah. So, and, uh, and then Gen Zs, when we think about that generation, we’re thinking about the fact that they’re, they’re growing in an era where they’re concerned about climate change, climate anxiety, global instability, and just overall digital burnout.
So when we’re talking about this competition of pain, it’s important to understand that people can talk about their disadvantages, right? In various ways, but it doesn’t mean that anyone is better, any one disadvantage is better than the other, right? And when I hear these kinds of tensions, I always personally try to shift the conversations from who had it worse to, how are we experiencing this moment differently, right? And what can we actually learn from each other within this organization? And I think that it’s important to ensure that we’re moving away from this competition of pain because it’s not productive, it’s not transformative. And once we start to understand that everyone has a viewpoint and everyone is going to feel certain ways, we can actually collaborate together, right? And that’s what intergenerational collaboration is about.
Leading with empathy, leading with connection is important. I recall that a mentor of mine had once said that, the idea of shared struggle, it doesn’t mean equal struggle. Mm, right? It means that if we have this idea of empathy for what the other person is carrying, we’re able to grow and transform as a community, and I think that it’s important to think about intergenerational collaboration in a way where we’re being curious about it and we’re trying to understand more about it and, and appreciate that diversity of perspectives.
Natasha Sharma is a certified Life and Business Coach, wellness specialist, and visionary DEI leader with over a decade of experience advancing social justice and wellness. As Founder & CEO of Power In Progress, a global consultancy, she helps individuals and organizations unlock their potential through inclusive, purpose-driven strategies. Natasha holds a Master’s in Public Administration from the University of Liverpool and is known for turning complex challenges into opportunities for growth. Her work—rooted in authenticity, empowerment, and systems thinking—drives lasting change at the intersection of equity, leadership, and transformation.
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