If you ask the average millennial about their retirement you’ll probably receive a familiar response: never going to happen. As they’ll tell you, salaries are stagnating, student debt is rising, pensions are declining, cost of living is going up. Traditional ways of building, and maintaining, wealth are becoming less and less attainable. 

All across the media, versions of this story are told. The U.S. National Institute on Retirement Security finds that 5% of people born between 1981 and 1991 are saving enough for retirement. The Huffington Post publishes an article entitled “Why millennials are facing the scariest financial future of any generation since the Great Depression.” The U.S. Bureau of Labor Statistics reports that, in 2020, only 28% of employees at companies with 500 or more personnel participate in a pension plan, down from 84% in 1981.

When this kind of consensus is formed, it’s usually time to ask some questions. Instead of dwelling on this monolithic narrative, we should ask: What might complicate this view? 

Retirement, in many ways, is the flip side of work: the place where perseverance meets security and achievement. Or, at least it was once. But retirement isn’t only about 401k’s and mortgage rates and inflation. It’s also about stuff like where we live, and how, and what we expect to do with our time. With these factors in mind, this article points to a few ways in which we might look beyond the dominant narrative.

Re-Shaping The Pace of Work

A recent report from the Stanford Center of Longevity is framed around two important bits of data: that the average five-year-old today is likely to live to 100 years old, and that this same five-year-old is likely to work for sixty years or more. Twenty years longer than their grandparents.

For those of us raised on the vision of a sixty-year-old retirement, the idea of extending our careers by twenty years might seem a bit dystopian. But that’s because our model of work—rigid, all-consuming, spiritually empty—is mismatched, in critical ways, to the natural rhythms of life. Work, as the report suggests, has a pacing problem. And we are now poised to enter a period of redesign.

The authors of the study, entitled “The New Map of Life” suggest a few ways in which that might happen, starting with the intensity of mid-life when the demands of raising children and aging parents coalesce.

To deal with this effect, the researchers suggest a sliding scale where workers are able to reduce or increase their hours during specific periods. For Gen-Z, who is expected to work eighteen jobs spanning six careers, this way of working might help reduce burnout and enable people to build more rich and varied personal lives. Rather than one, long retirement at the end of a career, it would mean enjoying what Tim Ferris has described as “mini-retirements.” 

Another approach involves rethinking the arc into retirement by gliding, or, slowing down the pace of work before it stops, and using “returnships”, or brief, internship-like periods when people could come out of retirement to mentor younger workers. As management theorist Chip Conley writes in his new book, Wisdom at Work, “everyone working past middle age today needs to become a modern elder.”


  • Could access to private markets help average people save more money for their retirement?  
  • Would you invest in the lives of your favourite artists and creators early in their careers?

Come for the Community, Stay for the Work

Most of our models of retirement are rooted in the social programs of the thirties, when policy analysts could safely assume things like a corporate workforce, and benefits like pensions and higher salaries. So when it comes to freelancing—which has seen a meteoric rise in recent years—retirement predictions are a bit of a mystery. Who will help with things like health insurance and savings plans as gig-workers age? But, recently, as the lines have blurred between work, entertainment, and friendship, freelancer networks are responding and creating support systems to manage these tensions. 

The concept of squad wealth, for example, refers to the way distributed groups of coworkers/ friends/ collaborators are working together to increase their collective well-being. For some, this dynamic is simply a matter of sharing work, as in freelancer collectives that frequently collaborate. But for others it goes one step further with groups tying together their financial lives in more concrete ways. CirclesUBI, for example, is a blockchain-based platform that pools resources from participants over time to create a members-driven universal basic income program. 

While much of this shift has to do with values (86% of millennials say they’d take a pay cut in order to do something that matters to them), some also argue that it’s tied to competitive dynamics. Advocates of Commons Based Peer Production, for example, a form of collaborative labor in which participation is mostly voluntary, argue that these firms actually outcompete traditional firms by reducing transaction costs.

As these groups continue to develop the tools, wherewithal, and technical knowledge to support themselves more effectively, it is possible that this form of work will become even more attractive, especially as people age. In this context, the formal boundaries of traditional working relationships might continue to dissolve and become more dynamic, flexible, and permeable. 


  • What can freelancer collectives do to support workers as they age? 
  • How might freelancer groups influence the larger work culture?
  • As more people become involved in projects like these, how will it shift the blurry line between employment and unemployment? 

Living Together

Traditional models of retirement are often based on two macro assumptions: that people will live in single-family homes and that, ever-increasingly, they will live in cities. But, as of recently, these are no longer stable assumptions. For the first time in nearly fifty years, young people are beginning to counter these trends—moving into collective living spaces both in and out of the city. 

This shift is being fueled by a mix of factors: declining marriage rates, the rising cost of living, the accessibility of remote work, and, for many, longer periods of mid-life transience. One result, as evolutionary psychologist Geoffrey Miller has described, is a “Cambrian explosion of different relationship patterns.” 

Living spaces are adapting to accommodate these realities. For example, The Collective London is the largest shared living space designed for millennials, offering members “a new way to live, work, and play.” Likewise, the Federation of Egalitarian Communities is a network of communal groups across North America focused on facilitating collective living. Another important trend is the rise of intergenerational care homes—facilities that aim to “end the age apartheid” by bringing people together from different generations. 

With the average Gen-Z expected to live in 15 residences throughout their lives, and the number of single people living in America outnumbering those who are married, new models like these will be needed. Will they become more important?


  • Could living in closer proximity help people reduce their cost of living, and support each other into old age? 
  • What other systems of care could evolve to ease the challenges of aging? 
  • Would you consider living in a communal living environment? 

Private Market Micro-Investments

The traditional rule of thumb for planning retirement is known as the 4% rule. Here’s how it works: Add up all your investments (in stocks, bonds, etc.) and, in your first year of retirement, withdraw 4%. After that, you just adjust the amount to account for inflation. Assuming a 6% return per year (the average return on the S&P 500), it should last you for 30 years.

But the problem with this equation is that, for most people, this is still a lot of money. For example, if your portfolio at retirement totals $1 million, you could only withdraw $40,000. This is why investment strategy is considered so important for retirement: the more you have saved, the more you’ll be able to withdraw. 

Luckily, certain shifts are making it easier for more people to access higher-quality investments: notably, in private markets. 

The first is the rise of investment syndicates, which are ways for retail investors (aka average people) to pool their funds to access private deals (often with minimums as low as $1k). And the other is the ability to invest in cultural projects via blockchain.

For example, Seed Club is a DAO that advocates for the use of ‘social tokens’, which provide ways for fans to invest in (and subsequently benefit from) the success of creators early in their careers. Another project is Remix Artist Collective (RAC), which has become the music industry’s go-to crypto source. It has a vision of using NFTs to cut out the industry’s middlemen, enabling assets to be controlled by creators themselves, including for resale over their lifetimes. 

These projects are important because, often, private markets are where the largest growth curves take place. Previously, it was only VCs, hedge funds, and institutional investors that could access many of these deals. But as technology makes these forms of investment more accessible, they may become important investment sources for the average person, helping more people build wealth. 


  • Could access to private markets help average people save more money for their retirement?  
  • Would you invest in the lives of your favourite artists and creators early in their careers?

Rethinking Retirement

Retirement as we know it is a relatively new phenomenon. In her book, The Evolution of Retirement, economist Dora Costa argues that until the late 19th century, people typically worked until they were not physically able to continue, at which point they relied on their family to take care of them. In 1880, she says, the average worker would labor up until fewer than two years before they died.

The point isn’t that we should accept the decline of retirement altogether, but that we should understand the familiar version as an artifact of a specific time—one that has a mix of positive and negative qualities. For most of us, when we look forward to the forces that will characterize our experience in retirement, we project forward many of the assumptions that have characterized the past. Some of these assumptions, however, may no longer be safe.

The forces that will impact retirement can’t be captured in mortgage and savings rates alone. Things like how we live, and where, and the ways we choose to work are equally tied to the ways we’ll retire. And, in this, we always have a choice—choices that are subject to vast and surprising change. As futurists like to say, “the future is already here, it’s just not evenly distributed.”