Generation Why

In the process of noticing this little seed of an idea, watering it, figuring out what it might need to come to life, and how it might not be a flower to admire but instead a vegetable that feeds a lot of other people and therefore cannot belong to me, or us… in the middle of that whole process, I realized how truly perfect it is that we are Generation Y.

Y is close to the end of the alphabet. It’s near some kind of conclusion, but fortunately, also close to a new beginning, too. I am not above a cheesy metaphor. We, too, have been living in a space of endings and beginnings for our whole lives, and to some extent, that’s just being human. But in our case, fellow Millennials, it’s happened in such a big way that it would be weird not to take notice of how it’s shaped us.

We witnessed the end of one millennium and the beginning of another, hence the name. I remember how momentous that felt. There was a lot of concern about what would happen to all the computers if the Y2K catastrophe manifested as imagined, but alas, they just flipped to 00 and all was fine. Always one to embrace a momentous occasion, I resolved that I would do the first cartwheel of the new millennium in my living room, which was a weird choice since I was neither good at cartwheels, nor in a living room with a ton of space, and of course the year 2000 had already arrived in other time zones. But I did it anyway, and to my 12-year-old self, it was the right way to enter the new era.

We are, of course, close to the end of the alphabet that defines each generation and I believe we’ve done a great job of passing the baton to Gen Z. Their gratitude is evidenced in their theft of our fashion, wired headphones, and aversion to answering the phone. We are the makers of Gen Alpha, and while we have some valid concerns about their uptake of Italian brain rot, we have rooted our parenting strategies in actual human psychology and for this we say, you’re welcome. They are unafraid of therapy and they appear to treat social consciousness as a fact and not a choice.

In more subtle ways, we are at the end and the beginning of so many eras in human history, which seem to come at us like pages flipping ever more rapidly - faster than we can read them, sometimes. We were becoming aware of ourselves and the world just as 9/11 occurred, and we had the jarring realization that we (as Americans) did not live in a bubble. We watched our country (and our generation) go to war, and not in the clear-cut, romanticized way of the greatest generation (and by the way, what a title!) but in the complicated, morally relativist way that would become the new norm for the foreseeable future.

I was 16 years old when I had my first opportunity to board a plane and leave my hometown for a young leaders week in Washington. We visited Congress, where some old man (I seriously have no clue who it was but surely a Congressman?) gave us an impassioned speech about how, as Americans, we have freedom of religion, not freedom from religion. That stuck for obvious reasons. We walked the halls of the U.S. Senate, searching for big names and stumbling across a little known freshman Senator by the name of Barack Obama. We participated in an exercise where we were invited to write our opinions, as the youth of America, on the Patriot Act. And man, did we have questions.

For the sake of brevity I have to fast forward through the many other ruptures we’ve experienced as Millennials - endings and beginnings. Decades of war, complicating our understanding of what is just and sustainable and durable and what makes peace; a global financial crisis that hit, conveniently, just as many of us were graduating college with expensive degrees and uncertain paths ahead (Gen Z, you did not invent the post-grad panic); the struggle to buy homes or build wealth as the cost of life outpaced our earnings and the American dream felt more like a theory; a global pandemic just as we were deepest in the trenches of raising the next generation, with our focus now narrowed to surviving, not thriving; growing political divisions and toxic media practices and conflict across the globe; AI and the dual promise of efficiency and irrelevance.

And I did not even mention social media! My god, we were the lab rats and we owned it. We became bedazzled, bejeweled, connected, inspired, powerful in the ability of our young brains to rapidly adopt and assimilate new digital tools. We leaned into both the social and the media, and frankly, we let the second corrupt the first. We’re sorry. We see that Gen Z is lonely and we worry about Gen Alpha. We are forming coalitions, as we speak, to normalize asking the questions about all the trade offs facing these digital natives. We’re sending our kids outside and we’re trying to remember how to embrace fun, freedom, risk.

With all of this happening in our relatively short time on earth, how we could not be asking, Why? Why do we do what we do? Why do we value what we think we value? Why shouldn’t we make some changes?

And this is where I see magic. If there is anything I believe wholeheartedly, it is this: The power is always in the question. Worry less about the answers and more about asking the right questions - the inconvenient ones, most often - and you will find your way to better days.

So, fellow Millennials, this is the space we’ve created here for you. We’ve all seen some things, and we have questions.

My sincere hope is that this is the place where we can ask them, together.

<3 Cait