The Bridge Generation

UNDERSTANDING UNDERSTANDING ISSUE 7

Not all of our destinies are firmly planted upon the ground. Some lifetimes stretch outward, across the chasm between those who came before us and those who will follow, serving, in essence, as a bridge from one generation to another. 

Over the last two decades my work has been to support individuals and teams as they evolve and become better versions of themselves. Along the way I’ve seen all types of personalities and biases get in the way of progress. Wicked vendettas, political agendas, untethered narcissism—all these and more have browbeaten too many good people and stripped them of their ability to affect change in our organizations and public offices. 

But something lately led me to think that there is a deeper, more interrelated opportunity for change afoot. And at the center of this opportunity stands a small but faithful generation poised to help transition power from the old guard to the new.

Let me elaborate.

Inside many of our world’s largest organizations sit individuals in positions of authority whose roles are beginning to sunset. The average age of a Fortune 500 CEO is 57. This means that, by and large, Baby Boomer and early part of Generation-X’s leadership teams are nearing the end of their tenure (with exceptions made for our too slow to retire political leadership, where the average age of a US Senator is 64). Over the next decade a huge transition of power will take place where current leaders will step down and new (likely younger) individuals will take the helm. 

It will come as no surprise that the next big wave of talent to wash upon our organizational shores will be made up of millennials. Millennials are a different type of thinker and participant inside organizations and very often, their way of engaging with established principles and culture is in conflict with the status quo. They’ve come to expect more and demand it from their workplaces and their government. 

But between this old guard and the new sits an oft-forgotten generation — Gen-Y.

There’s murky information about what denotes Gen-X from Gen-Y from millennials. Many historians try to group some of these together, but it isn’t rational, it just makes it easier to make their bar charts and graphs. Each of these generations grew up in a time and place that was different from their predecessor, have different ideals and, frankly, different mentalities on how they see themselves fitting into this strange world.

Now, one can certainly dismiss these broad-brushed demographic statements and instead point to more nuanced psychographics that claim it’s more about the mindset of a person and not their actual age that matters. This is absolutely true on an individualized basis. However on a societal level, when talking about corporate or governmental leadership, like it or not, but for a few enlightened outliers, most organizations are still stuck in a fairly ageist pattern of leadership appointments. As leaders grow old, the next and most senior (often closest in age) leaders are promoted into seats of power. We see it happen every day. 

The under-appreciated but soon to be reckoned with aspect of this modern scenario is that the organizations of today will all need major re-tooling to augment themselves into millennial-led businesses. The old guard is not entirely ready to hand over the keys to what, in their eyes, seems to be an entitled and naive generation that doesn’t understand how the world really works. Numerous studies like this one from Science have explored the “kids these days” sort of mentality that millennials are facing but the disdain is absolutely bi-directional.  

All of that said, the differences between these generations can’t be summed up by a handful of research studies. The crux of this is much more nuanced.

Millennials know how the world works; they just aren’t happy with it. And with an estimated $24 trillion in wealth transfer headed their way, they don’t want to play by the old rules anymore. But shifting that dynamic inside a large organization is not easily done. Instead, there needs to be an intermediary step that supports a graceful transition of power. One that history will likely forget, but without which a necessary sea change will struggle to come to pass.

This is the demographically small but critically important Generation-Y—those born from 1977–1981.

Is this a scientifically defined range for this generation? Sort of. More accurately though, it's an academically debated one.

Up until the Baby Boomers, modern society lived with a clean cut off between each generation. Those born from 1920 until 1946 were affectionately dubbed as the “Greatest Generation”. They fought in World War II. They kept the country running and the economy growing. They built industries and championed a new way of life in a rapidly changing America.

They were followed by the Baby Boomers—the oft-maligned offspring of the Greatest Generation who returned from WWII and started baby-making like there was no tomorrow. We made a lot of babies in America from 1946–1965. Approximately 76 million babies according to the Census Bureau. The Boomers rode through an insane amount of tumult in America — the Civil Rights movement, the Summer of Love, the Vietnam War, the economic downturn of the late seventies, the high-wire, cocaine-fueled Wall St. era of the 80s, the AIDS crisis, and much, much more. I get it. Boomers have seen some shit. And I’m sure it wasn’t easy. And while they definitely left later generations holding the bag for their misgivings, they are, like it or not, largely the folks at the helm of many of our modern day organizations.

But this is where the research starts to play it fast and loose with the generations that are to follow. Gen-X is defined by Harvard University and several other credible hifluten sources as those born between 1965 and 1984. OK, I guess, but not really when you consider that the same people at Harvard say that Gen-Y extends from 1977 to 2004. They effectively lump Gen-Y and millennials as the same group, which completely ignores the massive zeitgeist and innovation shift that happened with the advent and acceleration of technology between 1977 and the early 2000s. The competing view from Strauss and Howe, authors of the book Generations and the mega-nerdy, largely unrefuted experts on this topic, say that millennials are born between 1982 and 2004. Better, but they lump Gen-Y into millennials too, just on a tighter timeline. The overlapping years from the two studies chart a weird gray area from 1977 to 1981.

Four years. Four weird years.

Why doesn’t anyone know what to do with these people? (Note: I’m one of these people.) And why is it that two different and highly respected population and generational theory expert groups have struggled with this transitory generation between Gen-X and millennials? My guess is that it’s complex and up until this point in our history, we haven’t needed a “transitory” generation. One that helps an older generation make sense of the large generation that will inherit their roles as leaders in this world. Perhaps it’s because of Moore’s Law. Technology is advancing quickly and the millennial generation who were “born digital” are just too darn good at adopting whatever comes next while older generations were (by and large) challenged with the pace and diversity of information being thrown at them. My weird little Gen-Y group though, we weren’t “born digital”, but we were the first generation to learn how to adopt and integrate technology quickly into our lives. Our little 4–8 year old minds learned new technologies, somaticized countless interfaces, and nimbly navigated new experiences while our older siblings scoffed as they skated off to smoke cigarettes behind the mall.

Let me pause for a quick second to say that, yes, I realize much of this is perhaps too harshly generalizing. Sure, there are some Gen-Xers and Boomers who are the OG early adopters. In fact, much of the technology millennials were born interacting with was built by these folks. But those Boomer and Gen-X innovators represent a small portion of that 126 million combined populace.

So what’s next?

I believe we are entering a short window of time where a hard-to-understand, hard-to-quantify and hard-to-pin-down generation of Gen-Yers are going to take the helm of the organizations that need retooling the most. We are the translators that speak two very different languages but can straddle the middle and help serve as a bridge that sets up a new, massive generation of revolution-ready millennials.

Gen-Y’s leadership will be short-lived sheerly based on the numbers. There are about 64 million millennials compared to the roughly 10 million Gen-Yers out there. But this is the hand we’ve been dealt. 

And while it might conjure some existential dread to imagine your generation as one that will likely be lost between the waves of larger generations that came before and after it, not all generations need accolades and not all responsibilities need to be uniformly understood. Sometimes they are simply the byproduct of being born at a certain time and in just the right place.

Take good care,

MV

HAPPENINGS

Events, talks, workshops, retreats…

Things I’m doing and things others are doing that you might find interesting.

FROM SMALL TALK TO BIG TALK
Tonight! Tuesday, July 12th at 6pm in NY

There are still a few seats left for tonight’s talk and workshop at Neuehouse. I’ll be sharing some work from Applied Empathy, leading an exercise where you can get comfortable with the discomfort of being vulnerable with a stranger (or someone you already know), and also hanging out for some cocktails afterward. Come say hey. RSVP here.

UNDERSTANDING US INFORMATIONAL GATHERING
Thursday July 21st at 7pmET (virtual)

Last week one of my Understanding US co-founders (Sister Simone Campbell) was awarded the Presidential Medal of Freedom! Next week, join us and our colleagues for a 90-minute informational session to learn more about the work we’re doing to bring multiple generations and mindsets together to help America rediscover itself. Sign up for our newsletter to receive an invite.

RESET RETREAT
Sept 25th - Oct 1st in Telluride, CO

I’m excited to begin my first of several week-long retreats at the impeccably designed Reset Telluride. Join me for a week of hikes, clean food, fresh air, and mindfulness. I’ll be leading a series of workshops and programming designed to help you connect with yourself, and others more meaningfully. Reservations are now open.

OFFICE HOURS
Wednesday, July 20th from 1-2pmET

My Zoom door is open. No appointment or agenda necessary. Come and chat about whatever you’d like.

OPPORTUNITIES

Talent, jobs, investments, collabs, and more…

If you or someone you know is interested in making a move or if you’d like to share a need in this section on a future letter, drop me a line. It takes a village.

The fine folks at Dollar Donation Club have built a giving subscription that lets anyone contribute to some of the world’s most effective social impact projects for as little as $1/month. They’re embarking on their next investment round and are looking for mission-aligned impact investors. For access to the deck and data room, shoot me an email. 

Rally is raising a seed round. Rally enables groups to run “relational organizing” programs that are 10x more effective than traditional campaign tactics. Relational organizing can increase turnout between 1.2 and 5%, which is the projected margin of victory in 16 critical states where Democratic swing voting will be critical in the upcoming election. Check out their informational deck here and get in touch if you want to get involved.

EPHEMERA

Deep space, loopholes, goosefish, books I’ll never read…

Things I’ve picked up while meandering around the internet.

Today, July 12th NASA is releasing the first images from NASA’s James Webb Space Telescope—the deepest and sharpest infrared images of the distant universe to date! 

A woman in Texas who got a $200-plus ticket for driving alone in the HOV lane is battling the fine using a novel argument that her unborn child counts as a second passenger, based on new Texas abortion laws and the ruling from those asshats in the Supreme Court. 

Check out this wild goosefish (start at the 7:00 mark) for a dose of evolution at its finest. 

I have a tsundoku affliction.

Subscribe to read more Understanding Understanding.