Insights — November 30, 2018

The Great Millennial Paradox

All of the things that make Millennials great are also getting in their way.

by Emily Smith Cardineau


Paradox, loosely defined as the phenomena in which two seemingly opposed truths can be held to be true at the same time, is, as F. Scott Fitzgerald once observed, a difficult position to sustain. “The test of a first-rate intelligence,” he wrote, “is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” In short, living in paradox is not for the faint of heart. Yet it is something the Millennial generation, more so perhaps than any generation that has come before it, is expected to do, on a continual, daily, and even minute by minute basis.

The great paradox of the Millennial generation is that so much of what has made their generation great–their immense capacity for productivity, their ability to adapt almost instantly to the evolving world around them, their incredible digital savvy, and their hyper-educatedness–are now emerging also as impediments to their happiness, their sense of wellness, their resilience, and their confidence in the future. The difficulty of this position can lead not only to extremism, radicalism and the kinds of bi-partisanship that have come to define our age but also to a kind apathy that seems to be slowly creeping into the mindsets of Millennials.

At Cake & Arrow, we’ve spent the last several months trying to learn more about what will soon be the world’s largest living generation. We wanted to dig past the common stereotypes of Millennials–how they want to do everything online, how they love taking selfies, how they don’t want to buy homes–to understand more about their values, their mindsets, their motivations and how their experience of the world is evolving as they age into adulthood. What may have been true about Millennials five years ago may no longer hold up.

We recently conducted research workshops with three groups of Millennials across the United States, in Orange County, Austin, Texas, and New York. What emerged from this research were some of the key paradoxes Millennials are struggling to grapple with:

1. Digital technology both alleviates stress and creates it

At the core of Millennial anxiety is a digitally enabled hyper-connectedness that has come to define their generation. Beginning in adolescence and intensifying throughout their adulthood, the internet, smartphones, and social media have made Millennials the most connected generation in history, for better or worse. It has never been easier to purchase a plane ticket, watch a movie, attend a work meeting, shop for a new speaker, or communicate with a family member. And while digital technology has certainly made life easier in countless ways, it has not, as John Maynard Keynes once famously predicted, resulted in shorter work weeks and more time to ourselves. In fact, the Millennials we spoke with reported high levels of digital fatigue and discussed at length the way that digital technology has lead to a feeling that they must always be on and available 24/7, in their professional and personal lives. They feel overwhelmed, anxious, and on the verge of burnout and spoke about the need for digital detoxes, about establishing personal and professional boundaries quelled by digital technology, and the general feeling that while digital has made many things in life easier the conveniences are often outweighed by the stress and anxiety of always having to be “on.”

Let Millennials set the terms of engagement

While digital is not going anywhere, and a good digital experience will continue to be table stakes for any brand, companies need to think about ways they can help Millennials wrest more control over their digital lives, and create boundaries for themselves. Apple’s new “screen time” feature rolled out on the latest IOS is a perfect example of how technology itself can help Millennials regulate their technology use. iPhone users can now tell their phones how much screen time they want to limit themselves to and they want to opt out of alerts altogether.

As companies continue to refine their digital products and experiences and build new ones, they should consider how digital can be augmented by non-digital experiences, and how they can build features into their technology that help Millennials regulate and monitor their usage and provide them with more agency over how and to what extent they want to engage with technology. Brands tend to strategize around how they can claim any sort of real estate in a consumer’s mind so they can then inundate them with messaging; but rather than manipulating users by forcing them to react, brands need to allow consumers to set the terms of engagement. Apps and products that are not sensitive to these needs will be the first to be deleted when burnout sets in.

2. The world is speeding up and it’s slowing people down

As a generation that remembers a time before the internet–before smartphones, email, and social media–but who has now so fully integrated these things into their daily lives that it is difficult to imagine life without them, Millennials are more privy than anyone to the speed and extent to which the world can change. This may be why, when we asked Millennials about the future, most of them had a difficult time imagining anything beyond five years from now. One workshop participant even told us that when he thinks far enough into his future, much of what he imagines for himself hasn’t even been invented yet.

Yet even as Millennials become ever more adept at adapting to the rapidly changing world, they also tend to move more slowly through certain life milestones. One Millennial we spoke with told us that the biggest difference between his generation and his parents’ generation was the pace of their lives. For his parents, he explained, life moved at a more predictable pace, making things like marriage, family, establishing a career, and buying property easier to plan for and to work toward. With so much change happening so fast, for him, all of the energy that might go into planning for the future is instead spent trying to keep apace, professionally, technologically etc. with his everyday life. This makes planning for the future, especially a future which looks increasingly opaque and unpredictable, challenging.

Help Millennials feel like they are actively creating their futures rather than passively accepting them

One thing that gets lost in the hustle to keep apace with everyday life for Millennials is the ability to self-reflect and truly take stock of how they are spending their time, their money, and their energy and how this might be impacting their future. Millennials often feel like life is happening to them.

The Millennials we spoke with want more transparency into their own lives. They want to better understand how they are spending their time and their money, how the decisions they are making today will impact their future.Not only are they looking for opportunities to slow down, self-reflect, and take stock, but they want to use the knowledge they gain from doing so to wrest control over their own lives. This is why tools like Credit Karma are so immensely popular with Millennials. Credit Karma made something that was notoriously opaque – credit scores – free and transparent, and in doing so is helping Millennials better understand how the financial decisions they make today affect their future. Not only does this kind of transparency enable self-reflection, but it provides Millennials with a sense of agency and control over their future. With Credit Karma, a credit score is no longer something that is given to you, but something you create.

Brands should invest in tools and experiences that create more transparency for Millennials and help them better understand how their behaviors, decisions, and choices are impacting their futures. Drawing attention to patterns, to trends, to interdependencies, to the relationships between decisions and outcomes can help Millennials see the every day in the context of the big picture, and empower them with a sense of agency over their futures.

3. Too many opportunities make Millennials feels like they are never doing enough

Millennials in America not only grew up in an age of hyper-consumerism, but they were also raised to be uniquely idealistic. They were told that if they worked hard and went to college they could have it all – the career, the house, the family, the vacations etc. Combine this upbringing with social media and the way it enables Millennials to “shop” other people’s lives, not just for things, but for experiences, and it’s a recipe for serious FOMO. The problem with FOMO is that it not only does it create anxiety on top of everything else Millennials have to deal with it, but it can also keep them from accomplishing goals and life milestones by leading them into debt. Research published by Credit Karma earlier this year found that 40% of Millennials overspend to keep up with their friends. And not only are they overspending, when they do, they often regret it. According to the research, “two-thirds of Millennials regret spending more on social situations than they had planned, and one-third doubt they’ll be able to sustain this lifestyle for another year without going into debt.”

Seeing everything else everyone is doing on the internet makes Millennials feel like they are never doing enough–not accomplishing enough, not traveling enough, not making enough money. Millennials are one of the most productive generations in history, yet many suffer from guilt over their inability to fully take advantage of everything the world has to offer them.

Help Millennials align their goals with their values

While many of the Millennials we spoke to had a vague idea of how they wanted their lives to pan out, many were lacking a concrete plan of how they were going to accomplish their life goals. The seemingly limitless number of experiences, purchases, career paths, and romantic partners the internet surfaces for Millennials is one of the perks of living in this day and age, but also what makes it difficult for Millennials to be decisive and make the kind of choices that will help live the kinds of lives they desire to live.

One of the activities we had the Millennials do in our series of workshops was to spend time brainstorming all of the experiences they wanted to have, the things they wanted to buy, the milestones they wanted to accomplish in the next year, five years, and someday, and then align these things with their values. What many of the participants found was that once they looked at these lists in the context of their actual values– family, friendships, religion, or community–many of the things on their wishlist fell away.

Millennials need products, experiences, and solutions that can help them do this work on a daily basis–think about how their purchases, choices, ways that they spend money and time are laddering up to their values, and the goals they want to accomplish in life. There are opportunities for this everywhere–in budgeting and productivity apps, in scheduling and calendaring tools, in travel planning, in banking and insurance products, and even in retail, where subscription services are helping Millennials navigate and avoid the kind of anxiety that even shopping even for basic goods can create in a world with so many options.

4. Digital connectedness results in loneliness

It’s no coincidence that Millennials have urbanized alongside the rise of digital and social media. Moving to a city, away from family, friends, and community is easier when you can stay connected. Skype, Facetime, and all manner of social media that allow us to connect digitally across locations and time zones help create a feeling of connectedness, even as we might lack a community. Cities and social media can be equally anatomizing. In cities, we are surrounded by people, but often lack a feeling of connectedness with the people around us. With social media, we may feel connected with people, but lack the kinds of tangible supports you might get when you have physical proximity to your community.

The participants in our Millennial workshops expressed conflicting feelings about social media. Many of these Millennials, particularly those living in big cities far away from family members discussed feeling lonely, and while they were grateful to have tools like Facetime and Skype to stay connected with their families, they felt that social media gave them a false sense of connectedness, encouraging superficial relationships rather than true intimacy and connection. One woman in our New York workshop discussed how she had recently quit Facebook and was actively trying to whittle down her friend group and spend more time on the relationships that really mattered–visiting friends in person, calling people regularly on the phone, rather than wasting time liking hundreds of people’s photos she never even sees or speaks with.

One group of Millennials, also in our New York workshop, talked about how living in a big city, can make them feel like they don’t have a good support network that they can activate when they need help. They wanted a more connected group of family and friends who they could call upon for favors–picking up their kids after school when they have to work late, giving them to the doctor when they are sick, checking in on their cat when they are away. They reported feeling like living in a city, far away from “home,” meant they had to do life on their own. For many, this was the reason they don’t feel like they can have kids or even pets. They don’t have enough support in their community to make these commitments worthwhile, or even feasible.

Help Millennials create more authentic connections and build support networks

While social media has allowed Millennials to create connections, these connections are too superficial, and often too transactional, consisting simply of likes and comments, rather than actual experiences with people. Live streaming and Facebook groups are a step in the right direction, but brands need to be considering how digital experiences can create true interdependencies between people, and foster relationships in the non-digital realm.

A platform like Nextdoor, launched in 2011, which connects people living in the same neighborhood, are a great example of how digital experiences can facilitate in-person community building. Similarly, platforms like Meetup, which allow people with similar interests in the same geographic locations to create in-person events, can help people build meaningful relationships that are non-transactional. Companies need to consider how they can facilitate opportunities for people to not only connect meaningful with their communities, but to give back to these communities in non-transactional ways, sacrificing their time, money, and resources to support people in their communities in the ways they desire to be supported.

5. Education is freedom and a cage

As we have discussed elsewhere, education is now table stakes for most Millennials. It’s the key to having a successful career and any kind of financial stability. Millennials with a college degree fair significantly better financially than Millennials without. But for most Millennials, earning a college degree has also meant taking on extraordinary amounts of debt. And as the cost of college has risen by hundreds of percentages over the last several decades, wages have remained nearly stagnant, making a college degree a catch 22: something most Millennials can’t really afford, but also something they can’t afford not to do.

Furthermore, many of the college educated Millennials we spoke, especially the younger Millennials, felt that their college educations weren’t enough. Many had plans to continue their educations, whether that meant going to graduate school, taking post-baccalaureate courses, or pursuing online education.

For those Millennials that are in debt from their educations, while they may be better off career-wise and even financially than their less educated peers, paying off student loans can take decades, and can mean delaying marriage, family, and home ownership.

Help Millennials better manage their student loan debt and access affordable continuing education

When we conducted our initial Millennial research, we asked the Millennials we surveyed about one digital product that they feel has truly impacted their quality of life. While Credit Karma was the most popular response, another response we heard over and over again was SoFi, the personal loan financing company known for offering lower rates for student loan financing. These Millennials who use SoFi reported feeling like SoFi helped them finally get a handle on their debt and feel like they were making progress toward paying it off. While refinancing loans is not a business for everyone, determining ways that existing products can work toward helping Millennials better manage and understand student loan debt is a challenge many companies can take on. Financial savings and investment apps like Acorns and Digit are well positioned to help Millennials figure out how savings can be applied to debt, and can even create partnerships with lenders to help Millennials access better rates on debt.

While innovation in education has created an array of alternative education offerings for Millennials via platforms like Course Hourse and Master Course, we know from recent Deloitte research that Millennials are looking for their employers to invest in their continuing education. For some companies, this may mean figuring out ways to provide continuing education as a group benefit to employees and for platform innovators, this may mean determining how to make affordable continuing education a part of a service offering.


Generally speaking, Millennials get a bad rap. They are too often reduced to entitled, lazy, technology addicts who are afraid to grow up, when in fact, as a generation they have proven themselves to be resourceful, adaptable, creative, and productive members of society who are as attuned, if not more so than at least as much as other generations, to the joys, but also the limits and even the dangers of technology.

If there is one thing we have learned from our research, Millennials are acutely aware of the paradox that defines their generation: the ways in which digital technology at once liberates them and limits them from living their lives to the fullest.

For companies looking to design and innovate for the future, the key will be finding ways to break through the noise, and rather than simply piling onto the heap of experiences, products, and endless choices, helping Millennials sift through, take stock of and put to good use all that the digital universe has placed at their fingertips.