CHAPTER 5

Psychology/Mindset

There is no simple way to color every member of a generation with broad strokes, especially around psychology and mindset. To get the closest we can to identifying patterns thereof, we can look at defining historical events, socioeconomic conditions, prevalent technology, pop culture, plus any mass movements and their collective and individual impact on expectations and outcomes.

For historical events, the vast majority of millennials lived consciously through 9/11, the wars in Iraq and Afghanistan, the Great Recession, George W.’s, Obama’s and Trump’s first elections, al-Qaeda’s terrorist outrages, the Columbine shooting, Hurricane Katrina, the launch of Facebook, Snowden’s revelations, among other more localized events like natural disasters (earthquakes, floods, tornadoes, hurricanes).

Older millennials will also remember the end of the Cold War in 1991, the Lewinsky scandal, the first World Trade Center bombing, the O.J. Simpson Trial, Oklahoma City bombing, among others.

In socioeconomic terms, we went from a time of increasing prosperity mostly across the board (much of the Clinton years) when most of us were between fetal and high schoolers to a tech bust, then 5 to 6 years of recovery and job growth until the Great Recession, with increases in education costs far outpacing inflation and wage growth, ever-rising student debt, rising real estate costs, and an otherwise overheating economy with a widening wealth and wage gap. On the vice prevention side, many of us went through Drug Abuse Resistance Education (DARE) and some also through abstinence-only Sex Ed., down South.

Those older millennials (xennials, they’ve been called) who were lucky enough to start their careers before the Great Recession got in at least a few years of meaningful wage growth and career progression as a push forward, whereas those who were in school or otherwise just starting their careers experienced a massive setback in the form of unemployment, stunted wage growth, not to mention massive workforce reductions and business model shifts as in law and finance, resulting in increased outsourcing, automation, and elimination of many types of jobs forever.

On the technology front, within a few years, we went from rarely ever seeing cell phones to their ubiquity, as well as the spread and mass adoption of laptops, ICQ and AOL Instant Messenger, then social media including Friendster, MySpace, and most importantly, Facebook, Twitter, and LinkedIn. The rise of the smartphone has brought an always-on mentality both from employers, family, and ourselves, making loneliness easier and more prevalent, as well as accelerating a lack of social cohesion, given an easy fallback to limitless content consumption.

More than just tethering us 24/7 to our work, news feeds, and cat videos, one of the most amazing effects of technology in the last 10 years has been the explosion of crowdsourcing, crowdfunding, and other crowd-driven decision making.

Rather than trust Yelp or another platform with strangers’ biased—or outright made-up—reviews, many millennials reflexively crowdsource their personal social networks for all sorts of decisions, like which pediatrician to visit in Chicago, where to get a plumber in Reno the best cupcake in Barcelona, which destinations to visit in a certain country, and what cryptocurrency or cannabis business to invest in.

The Securities and Exchange Commission (SEC)’s regulatory loosening that’s enabled and empowered crowdfunding for the masses has led to an explosion of platforms and start-ups preselling everything from revolutionary juicers to newfangled watches and software on Kickstarter, IndieGogo, and what seems like hundreds of clones.

On other tech fronts, YouTube has made video the most consistently engaging content by time spent per session, while Netflix not only made retail video stores obsolete, but also invested massively into developing original shows and film, creating a gold rush by Amazon, Hulu, HBO, and finally Disney and others to democratize content creation and consumption away from control by the large film studios and TV network, also helping to unbundle cable and cut the cord, once and for all. Facebook’s Live and its spirit on LinkedIn and elsewhere have made broadcasting live video—and content creation, in general—easy as pie.

The low and decreasing cost of producing high-quality video, audio, print, and digital content has led to an explosion of content creation across all media, both leading to an endless flood of content created, posted, and shared every single day and making the value of each piece of content essentially zero. As mentioned earlier, a whopping 97 percent of all purchasers of online courses never actually finish them.

But just as importantly, the profusion of content has created loyal tribes of listeners, readers, customers, and in turn, employees out of groups of highly engaged and loyal fans for podcasts, shows, articles, books, and brands, overall.

Facebook has made comparing oneself to friends and others in the network a staple of everyday living during all hours, leading to further isolation, anxiety, and depression, despite a demonstrable bias by users to curate their posts toward unrealistically happy images of themselves on vacation, eating, hanging out with friends and the like.

Instagram has further accelerated this unrealistic image making and made it the standard way to broadcast status. As a result, adults and children alike engage in comparing themselves to others in every form of social media as a daily, often hourly exercise.

Twitter has made broadcasting short messages to a mass audience easy as a click, helping start revolutions in the Arab world, flash mobs, and tweet storms. This has given many armchair commentators a false sense of aggrandizement, not least our president. Yet more importantly, the speed, ease of use, ubiquity, and easy manipulation of social media has, unsurprisingly, led to the profusion of not just images and narratives of fake it ‘til you make it, but the creation and spread of fake news with the help of rogue state and nonstate actors like Russia, China, North Korea, and other dictatorships (see https://www.clingendael.org/sites/default/files/2018-05/Report_Hybrid_Conflict.pdf).

The downfall of science and medicine as the last frontiers of truth has resulted from the increasing politicization of science, shrinking research budget allocations, and a rocketing rate of research article retractions in top magazines. No wonder most people resort to Dr. Google before making their appointment.

More disturbingly, the rise of deep fakes is making it downright impossible to tell the truth from truthiness. And as icing on the cake, the president’s personal lawyer (Rudy Giuliani) says on national television that “truth is not truth.”

On the more buttoned-up, professional side, LinkedIn has standardized the way we display ourselves professionally to the outside world, often becoming the first entry in a Google search for our names. This has, nevertheless, failed to prevent the conflation of personal and professional brand and the adjustment of both to more cleanly fit with the other, in mind and in deed, at work.

Skype, WhatsApp, Viber, and most of all, FaceTime have made free, instantaneous communication possible with anyone, anywhere in the world, giving both comfort and joy to family far away and accessibility to far-flung people, but also accelerating the always-on and always-available sensibilities.

Snapchat has made it easy for anyone to share anything vapid, racy, or stupid with friends with minimal risk to outside exposure—and Google indexing. That is, with the exception of Snapchat’s own data collection.

This progression of social media tech has taken us from guarding our privacy to having none, then to feeling social pressure to share (and curate) our public online image all the time, from being mostly IRL (in real life) to mostly online, from having illusions of privacy from government monitoring and data collection to expecting all communications at all times to be within the government’s and tech’s purview.; All promises to the contrary are no longer being taken seriously.

One important benefit created by social media aside from speed and ease of communication is that it’s taken away the need for much time or overhead costs to start a business by allowing leverage of our social networks quickly to sell anything, needing only a smartphone and a PayPal link to bring in revenue.

The dark side of social media and related tech has been the anonymity that unchains trolls to threaten anyone, anywhere with exposing their address, private photos, ill-advised comments, or other damaging material. Much of this is done by trolls and cyberbullies with few, if any, repercussions (some states have enacted—or are in the process of enacting—laws to counteract this) (see https://www.businessinsider.com/why-now-is-the-best-time-to-start-a-company-2014-10; https://www.forbes.com/sites/johnrampton/2015/04/09/10-tips-to-dealing-with-trolls).

The other negative effects of social media include addiction, isolation, lack of social development for kids and adults, unrealistic images of success from entrepreneurs and peers, as well as the complete loss of privacy and inability to bury or timely delete ill-advised tweets and FB posts that harm reputation, often very quickly and irreparably (see http://www.bbc.com/future/story/20180104-is-social-media-bad-for-you-the-evidence-and-the-unknowns; https://www.forbes.com/sites/alicegwalton/2017/06/30/a-run-down-of-social-medias-effects-on-our-mental-health).

Loss of privacy through authorized and unauthorized user data access has exacerbated and normalized the effects and extent of hacking, customized ads trailing you everywhere, fake news targeting by state and nonstate actors to influence elections and commit fraud and theft, the creation of an echo chamber in our online (and, in turn, real) life, further splitting us along the tribal lines according to signals of status and virtue.

One other tech trend that has seeped into our daily routine is the on-demand delivery of food (Instacart, AmazonFresh, UberEats, and others), media (Amazon, Netflix, Hulu, HBO, many others), consumer goods (Amazon, Alibaba), money (PayPal, Venmo, many others), transportation (Uber/Lyft and clones, Car2Go, Maven, Citi Bike, Bird, Lime, etc.), and a massive variety of services and information (TaskRabbit, Pager, Fiverr and Upwork, Trulia/Zillow, tutoring, coaching, tailoring, interior design, etc.), plus seemingly everything else.

Technology around instant communication, sharing, and collaboration (Slack, Trello, Skype, Zoom, and many others) has made work more flexible and often just as easily done remotely. The way we learn, even if it still usually starts with Google and Wikipedia, is often undertaken without thought of accreditation or grades, through MOOCs and all sorts of gamified micro-learning and celebration of small wins. On-demand and sharing economy business models have helped millions create side hustles and profitable businesses from work outsourced anywhere around the world with the talent and wage arbitrage to benefit all involved.

Overall, even as tech innovation has leveled off in the last few years due to consolidation and an oligopoly by FAANG in the tech industry, the speed of change in our lives thanks to evolving technology has continued increasing. The next wave is already here, with the internet of things (IoT), artificial intelligence (AI), machine learning, and blockchain being integrated into every corner of our personal and business lives. The jury is still out as to the extent of job automation and loss to expect in the coming years, as well as the extent of the benefit to our Gross Domestic Product (GDP), to say nothing of the massive potential for everything from more accurate diagnoses of disease to better business decisions, and so on.

The speed of change, while exhilarating, is the source of great uncertainty and anxiety for millennials and all other adults equally, in the absence of protections from uber-intelligent robots set to take over our lives, a universal living wage to buttress against massive job automation, and other safeguards for those not owning or otherwise in control of the technologies integral to our personal and professional lives.

Standing on one foot, this progression has taken millennials from the middle or end of childhood innocence to the constant specter, then expectation of terrorism, sex scandals, online shaming, school shootings, small and shrinking attention span, lack of civility in public discourse, massive debt, job losses and diminished earning potential, climate-related natural disasters, plus major life events (starting a family, getting better jobs, buying a home, starting a business) later than expected in life (if ever) and at a more modest level than we were brought up to expect. Cry me a river or not, these formative experiences have clearly left their mark.

In short, the most coddled generation brought up on promises of gold at the end of rainbows suddenly had its bubble burst through a series of awful, large-scale events out of its control, and has had to react with as much pragmatic optimism as possible to better its lot. That is to say, even while looking cynically at the work, promises, privilege, and guidance of older generations, who helped construct or bring about those very socioeconomic and world-historical circumstances like war, rising inequality, stagnant wages, unemployment, and climate change.

Imagine going from a sheltered suburban childhood with little care in the world except looking cool in school and getting good grades while playing sports for fun to leaving college 4 years later with $25K in debt to start a job in a field you’ve been groomed for your entire life, only to lose your job in the recession, then do grad school and rack up another $200K in loans, graduate into a field with few jobs, then have to wing it in life by getting temp jobs, surviving between projects, starting a family, living in far-from-affordable housing, always living paycheck to paycheck while giving away essentially all of it for housing, food, expenses, and loan repayment. Imagine making bad decisions because of missing financial savvy on top of anxiety and depression from not yet knowing your purpose and meaning in life due to circumstances.

This is what makes it hard for so many millennials—and Americans of all generations, in general—to support a family, save up to buy a home, never mind for their children’s education, savings, travel, and so on.

On a lighter note, millennials have made do as best they can, even quite well on some accounts. On the food front, for instance, the organic/artisanal, local/slow, world fusion food movement has taken off among millennials, driven by Whole Foods, Trader Joe’s, and local competitors, as well as farmers’ markets and food trucks as a lower-risk alternative to restaurants.

At the same time, craft coffee, craft beer, and even previously “exotic” condiments have become increasingly popular with the rise of urban hipster culture. The latter stands for little of anything concrete except contrarianism to established orthodoxies, small comforts in life, casual dress and speech, flexibility in work and family arrangements, being nonjudgmental except of those prejudged as personae non grata, especially anyone accused of clinging to guns, religion, and other red state elements of worldview.

As for pop culture, millennials have witnessed a transition from the grunge of the early 1990s to rap & R&B on MTV and VH1; the scourge of reality TV; an explosion of unbundled and easily shared content of all sorts; an Internet broken periodically by Kim Kardashian’s behind, Trump’s tweets, and arguments about dress colors—plus a fractured media landscape, culture wars played out along well-established lines, and a love–hate relationship with the glamour and screwups of tech moguls.

In the workplace, millennials are more open (some would say, more shameless) than previous generations in asking of their potential employers a redeeming social mission (not just prestige) that reflects well on their own personal/professional brand (the two have no practical distinction, any longer), a diverse and inclusive workforce, an environment where they receive regular feedback from their manager, an HR framework that not only pays them fairly and takes care of their health and finances, but also utilizes more of their talents and surrounds them with people they respect and who respect them.

And perhaps more than anything else, millennials are looking for managers who display constructive empathy (if not always radical transparency), listen with an ear to understand—not micromanage—and focus on helping the employee as a human and professional develop and become the best version of him- or herself. The boss and company that care keep top talent around longer, in part because they’re so rare in a corporate world obsessed with the bottom line, innovation—anything other than creating a culture of care at work.

They also greatly value a culture that celebrates small wins, gives them flexible (in particular, remote) work arrangements and some freedom to pursue side projects, as well as gives them both open and anonymous means to communicate with management the things they like and dislike, so they can be quickly fixed and/or improved. Millennials are keen on working smart, not just hard, which means having a dedicated budget for the latest tech and productivity tools, as well as a concerted learning and development (L&D) framework that helps them build their own brand through contributed thought leadership, speaking, and teaching other team members and industry colleagues.

A no asshole rule is very popular in VC-backed tech start-ups, including The Muse, where the policy has repeatedly passed muster in my interactions with employees. In short, working with people you get along with, learn from, and respect mutually is no longer a luxury, but a requirement, given millennials’ workaholism and impatience with moving up quickly to bigger and better things.

In all, there is generally growing awareness in companies of multiple career options for employees and highly varied trajectories and greater ownership of employees’ journeys and life stories. This may be due to the growth of a therapy culture and/or the emergence of tens of thousands of coaches and consultants easily available on demand for every kind of career, life, and business in the last decade.

Socially, millennials have experienced a time of greater urbanization (more young people moving to or working in urban areas) and gentrification (the conversion of urban downtowns and ho-hum suburbs into tony hipster havens), as well as diversity (more immigrants from all parts of the world as a percent of the U.S. population, a rising proportion of minorities and women in the workplace, politics, and other areas of life), inclusiveness (gay marriage and nonbinary gender identity recognition), and the attendant legal protections therefor.

Save for high-growth tech start-ups run by bros now in deep water for lack of diversity and inclusion (D&I; see Uber and a long line of others), millennials for the most part expect and value the presence of and collaboration with people of different backgrounds and worldviews. Perhaps due to the lingering effects of the Great Recession, millennials are both less mobile and more rooted than previous generations.

Religiously, millennials tend to be less religiously observant, even if they seek spirituality in all sorts of nonreligious pursuits to make up for the void of existential structure and explanation. The institution of marriage has undergone an evolution with millennials. The stigma of living together without being married, even with kids, is long gone. Many millennials choose not to marry or at least to marry later, when they are better situated financially and professionally. As such, it’s interesting to note that millennials are the driving force behind an 18 percent drop in the divorce rate between 2008 and 2016. Even so, marriage is less common and largely an event earned, rather than arranged with much less regard for the couple’s life circumstances, as in the past.

On the subject of managing expectations, a bevy of social apps ranging from Tinder and Bumble to Shapr and a thousand others have spurred an expectation of on-demand transactional encounters by choice, making unfocused networking unnecessary and lower in quality, as well as spurring curated IRL events (dinners, business speed dating, etc.) prearranged for fit and quality and focused on a clear theme.

On the social front, especially for urban millennials, there has never been a more exciting time in history to assume whatever identity they wish, in any forum they wish; to create content; as part of a tribe online and/or IRL, anywhere around the world, around any cause, product, brand, service— or for no reason at all—for free or next to nothing.

On the flip side. There has also never been a more anxiety-ridden time, given the easily searchable digital record one leaves online, ridden with youthful indiscretions and other inconvenient truths of growing up before knowing all the rigid and subtle rules of corporate America. There is now, more than ever, a myriad ways in which self-selection, unconscious bias, and purposeful discrimination still very much affect everything, including hiring, credit, housing, academic admission, as well as all sorts of basic, social, and financial decisions.

We may not be quite at the level of China’s dystopic social credit system, but AI, machine learning, and the increasing migration of every area of life to the blockchain will go only further to eliminate the potential for human error and fraud, even while potentially institutionalizing some form of bias into every decision critical to accessing opportunity.

Rather than solely being a cause for conscious or unconscious bias or discrimination by employers or prospective mates, affiliation with any particular group or identity (within legal and mainstream ethical boundaries) can instead mean a wealth of opportunity in business, career, or personal life. But for the vast majority of those millennials who must compete for a job, housing, credit, funding, and other milestones critical for adult existence, family, and professional life, the corpus of data available about them is a source of constant anxiety and uncertainty.

Any social media post not sufficiently anodyne, any formal or informal litmus test failed through a racy photo or offhand retweet, article written for the wrong audience or cause supported—or even just a photo that’s cause for damnation by association—can instantly derail a career, make one lose a job, lead to a boycotted and dead business, denied membership to professional associations, not to mention social ostracism.

Sensitivity—and obedience—to an informal and ever-shifting code of conduct and presentation of self in public and professional fora is a delicate and increasingly difficult dance for millennials to manage, since they no longer have the folly of youth to excuse behavior adjudged unacceptable nor have the tangible power in politics or corporations to change policy, enact law, or otherwise shape public discourse meaningfully.

Being under a constant microscope from all sides—when one has no f*ck-you money or political power and when one is dependent on the very people in power who demonize your entire generation for a living—has a tremendous chilling effect on social and political activism that’s not as easy as protesting Trump’s policies or climate change, conservative dogma, or any of the other “easy” pet liberal causes and issues.

Hence, it isn’t difficult to understand why millions of students and young adults aren’t protesting in Washington against draconian student debt policies, lack of affordable housing, police brutality, or much any other issue of unique generational import.

Millennials are, on the one hand, the most educated and coddled generation raised on the promise of an outsized influence in an ever-growing globalist economy and superior world order based on classical liberal values; on the other hand, they are a generation screwed by the economy, older generations’ selfish and wrongheaded decision making and institutions we don’t trust, runaway technological change and economic shifts favoring aging kleptocrats and the ultra-wealthy, as well as a surveillance state in bed with a tech oligopoly.

The simple truth remains that we as a generation have much more to win from continued cooperation in a globalist democracy based on classical liberal values and the skewed market economy run by aging kleptocrats and older elites. That is, as long as they maintain the promise of giving us the opportunity of moving up slowly, but surely, in our personal and professional lives, than from any alternative of our creation or others’ imposition. In short, the overwhelming majority of us feel we’re better off trying to change the political and economic system slowly from the inside, rather than calling and protesting for wholesale change.

If and when this calculus changes, then it will be a different conversation, but for now, our current world order is all we know as Americans (except those of us hyphenated Americans brought up under totalitarian regimes like Soviet Russia, communist China, and others).

And more than anything, millennials know that any semblance of a safety net in the form of social security and other entitlements like unemployment benefits and Medicare is small, insufficient, and shrinking by design thanks to conservatives in power (themselves quite wealthy, on average), leaving us with little to no room for error in getting it right with our careers, finances, and lives, in general.

We’ve often got nobody but ourselves to rely on, because our parents and extended family are also just barely making it in life, due to stagnant wages, longer life, and the lingering effects of investment loss in the Great Recession. The proof for this is the low and shrinking rate of social mobility.

This is the main—and simplest—reason for why millennials tend to be risk averse, less entrepreneurial and mobile, for why we are fond of the sharing economy and other ways to save money and pool resources for better mutual outcome.

We haven’t necessarily given up on the American Dream of a family with 2.1 kids, a steady job, a three-bedroom house in the suburbs with a two-car garage. We’re just much more sober eyed about what it will take to actually reach those goals. But even if it’s taken longer than expected, many of us are well on the way.

On a separate—and mixed—note for democracy, the surge of diverse and inclusive voices and fora and policies has led to checked privilege, white guilt, and the rightful outing of sexual harassers and predators in positions of power, while empowering (at least in theory) for diverse and inclusive voices. Concrete change in boardrooms and halls of political power has been slower than the rhetoric would suggest, but is picking up steam. This development has been a big blow for the traditional power base of conservative white males, which, judging by the presidential representative thereof, is embattled.

Notably, the culture wars on steroids between conservatives and liberals in the United States have effectively silenced centrists of all stripes and laid all sorts of hidden mines in our democratic discourse around racism, genderism, acceptable and unacceptable opinions in the field of discourse, effectively reducing it to either anodyne or dog-whistle talking points and tropes broadcast on Twitter for the benefit of the supportive base by both sides, creating an insulated echo chamber that’s potentially one market crash or police-caused death away from social unrest and outright violence.

The two sides have simply never been more trigger-happy and ready to destroy the other, no longer even feigning anything like a common interest in the health of our democracy or republic, rather obsessed with getting even and naked self-interest. The fringes from both sides have gone mainstream and the incumbent adults in the room (boomers and Gen Xers beholden to principle or at least corporate lobbying interests) are getting voted out of office, tarred and feathered in the media. Time will tell if it’s a revolution or jumping the shark.

And so, millennials and others have on paper never been freer to express their opinions on gender, race, identity, or any other field of inquiry, but only insofar as their opinions must hew closely to narrow prevailing orthodoxies in the halls of power, the academe, and corporate boardrooms. One wrong word, opinion, statement, photo can lead instantly to demonization, death threats, loss of career, and downstream effects for oneself and one’s family. Choosing one’s words carefully is a hallmark of modern American existence in an era of political correctness gone amok.

We have never been closer together through technology, yet we’ve never been further apart from each other due to lack of common purpose, fractionated into social, political, culinary, sartorial, generational, ethical, and ethnic micro-groups, connected by little more than institutions we distrust, laws and regulations that favor the wealthy and privileged.

We live in times that have never been better by standards of life, health, and average income, yet we’re so anxious and depressed that we seek escape any way we can.

Our entire conscious lives, we’ve been sold a bill of goods about an American Dream that hasn’t quite materialized for too many of us, or at least nowhere near as quickly. We’re no longer drinking the Kool-Aid, but we’re also not ready to puncture the bubble and demand change through sustained activism, either. Too self-absorbed, self-interested, and unsure of where the world is going, most of us are in a holding pattern, waiting for Godot or otherwise affecting change on a smaller, local level, for now.

We maintain the illusion of eternal progress by sticking to outdated, misleading measures of health (life expectancy) and wealth (GDP per capita, real estate prices), hoping and praying that the structural problems in our society and economy don’t come to a head—or at least don’t blow up in our faces—too soon or too abruptly.

While this chapter is nominally about millennials in America, the majority of elements of mindset and psychology described herein are equally applicable for large proportions of Gen Xers, boomers, and Gen Zers, since we are all largely in the same boat with similar pursuits, wants and needs, technology we use, and political, societal, and economic constraints on our opportunity, success, and livelihoods. The only difference is that some of us are later or earlier in the journey, with different elements of background we’re born with, levels of education, cyclical economic and social circumstances, opportunities, and the ability to convert opportunities into success.

America has always been based on exceptionalism and building a better system for future generations, as much as it was built on reinvention of self. While the sense of exceptionalism has come and largely gone in our time, the reinvention part is as relevant as ever in an era of massive technological and economic change.

Only time will tell whether those institutions we distrust and the self-interested gerontocrats who run them and bash us at will save the American experiment again when the next recession, bubble, spasm of social unrest, and partisan culture wars erupt when the fig leaf of nominal common interest in preserving our republic is ripped off.

It also remains to be seen just when—not if—millennials fully assert themselves as a political and economic force at that time, demanding meaningful change as a group like the boomers did in the late 1960s and early 1970s, no longer remaining silent bystanders who flock to economic, social, and political safety.

We may be a bit late in the game compared with our boomer parents at our age, but as every generation has in the past, we will continue to have our defining moments. With America still humming along and with plenty of growth left and fuel being plentiful, there is yet cause for optimism, even with hyper-partisan politics and totalitarian regimes striking at our credibility and infrastructure from afar.

***

Summary

Psychology/Mindset—how we think, what is unique (digital natives, lack of patience), what is same as for other generations before us going through this stage of their lives; discussion of our anxiety and decreasing religiosity, lack of rootedness and yet lesser mobility than past generations

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