Who We'll Be in 2029

The jobs we didn’t expect, the systems we’re rethinking, and the future we’re building together

Four years from now, in the spring of 2029, a new wave of students will toss their caps into the air, graduating into a world dramatically reshaped since the start of the decade. But they won’t be the only ones crossing thresholds. Every generation—whether retiring, rebuilding, rising, or still reaching—will face its own kind of transition.

The years between now and then are also a kind of collective graduation: a rite of passage through social upheaval, technological acceleration, and a profound turning of the generational wheel. Amy Webb at SXSW in 2024 called this Generation T: “Collectively, we are all going through something important right now, which makes us Generation T. We are the transition generation. Everyone alive today, every one of you, is part of a major transition, which means that our society will be very different when that transition is complete.”

This acknowledges we can’t predict 2029 with precision—there are too many variables in play. But by zooming out and taking stock of the broader patterns, we can start to glimpse the outlines of what’s unfolding. This is less about forecasting and more about mapping the terrain: who’s stepping into power, who’s letting go, who’s reinventing, and how each of us might show up differently in a world remaking itself in real time.

For the Silent Generation, now in their 80s and 90s, this is a moment of reflection and reckoning. These are the people who came of age in the shadow of World War II and helped build the foundations of modern America—from its suburbs to its bureaucracies. But many of the institutions they shaped are now under siege or being dismantled altogether. Watching this unravel can be disorienting, even painful. At the same time, this generation models grace in transition: scaling down, passing on stories, and reminding us—if we choose to listen—of a slower, more civic-minded way of being.

For Boomers, the next four years are about legacy. Many will be in their 70s and 80s, leaning on the systems they built—Social Security, Medicare, the postwar institutions of work and governance—and hoping those structures remain stable. Some will step back from public life, while others will linger as elder statespeople or cultural icons. But the baton is passing, whether by choice or by necessity. For many Boomers, 2029 will be less about control and more about influence: offering wisdom, not direction.

Generation X may finally get its moment. Long sandwiched between two louder cohorts, Gen X enters this period as the seasoned establishment—running companies, managing crises, bridging divides. They are pragmatists by design, raised in the backdraft of the Cold War and the front lines of deregulation. In a world that’s no longer about lifelong careers but instead about constant adaptation, Gen X might thrive: they understand both analog reliability and digital fluidity. And yet, with midlife transitions looming, many Gen Xers are asking deeper questions about meaning, impact, and whether the climb was worth it.

Millennials will be at the heart of the action. This cohort is now in its 30s and 40s—prime years for leadership, parenting, and reinvention. They’ve grown up through economic shocks (9/11, the Great Recession, COVID), and they’re no strangers to navigating instability. But between now and 2029, Millennials will start to shape institutions rather than just survive them. In government, in business, in media and community life, their values—collaboration, inclusion, digital literacy—will start to set the tone. They are also at the forefront of rethinking work itself: pushing back on hustle culture, demanding flexibility, and seeking purpose over prestige.

Generation Z, meanwhile, is stepping into adulthood. This group, aged roughly 17 to 32 in 2029, has grown up amidst constant crisis—school shootings, climate anxiety, political polarization, pandemic lockdowns. They are both highly pragmatic and deeply idealistic. They don’t trust traditional institutions, but they believe in mutual aid. They use AI fluently, but they crave real-world connection. Their challenge—and opportunity—is to turn disillusionment into design: building new systems where old ones have failed. As the largest generation of digital natives, their vision of leadership may look radically different from what came before.

And then there’s Gen Alpha—the AI kids. By 2029, they’ll be ages 5 to 16, coming of age in classrooms powered by AI tutors and custom learning paths. They’ll grow up seeing careers not as ladders but as lattices: multi-directional, modular, fluid. They’ll question the value of a four-year degree not out of rebellion, but because alternative pathways—micro-credentials, apprenticeships, creator careers—will seem obvious. The world they inherit is being built now, and the values we embed in today’s institutions will shape how they trust, learn, and lead tomorrow.

Across every generation, the idea of a "career" is evolving. In 2021, we were still talking about return-to-office debates. By 2025, those debates will feel quaint. Work is becoming more skill-based, project-oriented, and AI-augmented. The traditional ladder is being replaced by something more like a jungle gym—messy, nonlinear, often self-directed. This shift is creating both opportunity and precarity: while some can thrive in a fluid economy, others may fall through the cracks if safety nets aren’t rebuilt.

Higher education is facing its own reckoning. Once a near-universal stepping stone, college is now being re-evaluated for cost, relevance, and return on investment. Millennials carry the burden of record-breaking student debt; Gen Z is increasingly skeptical of traditional degrees. By 2029, we may see a hybrid model dominate: shorter programs, more online offerings, and greater emphasis on what you can do, not just where you went. Lifelong learning will be less of a slogan and more of a survival skill.

All of this unfolds against the backdrop of a major U.S. presidential election in 2028—a generational turning point. For the first time, Millennials and Gen Z will make up the largest voting bloc. That shift in electoral weight could signal a change not just in who gets elected, but in what kind of future gets imagined. Will younger voters turn out? Will they trust the system enough to shape it from within—or will they channel their energies into alternative structures and grassroots movements?

And yet, generational change is never just chronological—it’s cultural, emotional, political. The 2020s are not just a decade of handoffs; they are a decade of transformation. Some generations are letting go. Others are stepping up. But we’re all navigating the same currents of uncertainty, whether we're questioning our careers, rethinking what it means to learn, or simply trying to stay connected in a world moving faster than any of us anticipated.

When I began researching this piece, I asked ChatGPT for help mapping these shifts. I ended up with 24 pages of notes—economic trends, astrological forecasts, demographic insights. But what stuck with me wasn’t the data. It was the feeling underneath it: that we are all, in our own way, graduating into something new.

The question isn’t whether change is coming. It’s how we meet it—together, across generations, with humility, creativity, and care. The future is not just arriving. We are building it. And who we’ll be in 2029 depends, in no small part, on what we choose to learn—and unlearn—between now and then.