This is how each generation can freelance during and after the pandemic

Data shows that in the current COVID-19 landscape, half of companies are considering layoffs as a long-term operational strategy. Freelancers may be best positioned to pick up the work.

This is how each generation can freelance during and after the pandemic
[Photo: Sam Wheeler/Unsplash]

The job market is undergoing an unprecedented shakeup. Jobless claims topped 20 million in the U.S. since the start of the COVID-19 shutdown and month-to-month activity on freelance platforms nearly doubled in some industries.


To ride out the storm, professionals of all generations appear to be turning to “portfolio careers” to earn their living through a mix of contracted freelance jobs, consulting gigs, short-term projects, board membership, and other engagements that allow them to apply their expertise under flexible conditions.

While a continued job slump is almost inevitable for the time being, a group of economists predicts a ‘U’- or even ‘V’-shaped recovery. This is where the sharp plunge we’re experiencing now is quickly followed by an equally sharp rebound in the latter half of the year. It is possible that some of the jobs currently cut or furloughed will be replaced by part-time contractors and freelance consultants in the long-term. In March, half of CFOs described their teams as lacking the right skills to meet future business needs, for example.

Those who pursue portfolio careers may be better positioned to stay ahead of the eventual recovery, especially as companies seek to safeguard cash flow by balancing fixed costs with rising demands for new capabilities and talent.

Until now, much of the media conversation about the gig economy has focused on millennials and Gen Z. But COVID-19 has knocked the door down for more freelance work, and the portfolio career is trending across the generations. While many professionals may unwillingly find themselves ousted from stable full-time employment, emerging opportunities in the marketplace may also prove the portfolio career to be a boon for professionals of any age—especially those looking for higher income prospects, personal fulfillment, lifestyle changes, independence, flexibility, or excitement.

Here are some insights on how COVID-19 is shining an even brighter spotlight on portfolio careers across the generations—and strategies that professionals of all ages can leverage to seize new opportunities, reimagine their careers, and gain greater control of how they spend their time and energy during the COVID-19 recovery period.


Boomers are financially and personally motivated to keep growing

When we think about the gig economy, stereotypes of millennials and Gen Z often come to mind. But millennial freelance coders or bloggers typing away at the coffee shop aren’t the only ones who have been thriving in the gig economy. It turns out nearly half (49%) of freelancers are over the age of 50–by far the largest segment of the freelance workforce– according to data from FreshBooks.

The anticipated lifespan for baby boomers has increased, so many are choosing to work longer. But financial pressures are also at play in keeping boomers in the workforce. For example, after weathering the global financial crisis in 2008, and enduring years of stagnant wage growth, a study from the Insured Retirement Institute reports that 45% of U.S. boomers have no retirement savings. And for those who do, COVID-19 has triggered market volatility and upended retirement portfolios across the board.

Instead of remaining displaced, many boomers who find themselves unemployed will likely circumvent job market instability by working outside of the conventional “one job” model. According to data from the freelance platform Wonolo collected before COVID-19, boomers have been leading the pack in the global gig economy as they take on more jobs, earn more money, and receive better feedback than their younger counterparts.

Apart from financial pressures, many boomers are also taking on freelance work to enjoy a sense of personal purpose. Having a portfolio career allows them to dedicate time and energy to the causes they support, such as consulting for a nonprofit or offering leadership training to emerging professionals.

Boomers’ seasoned portfolios have prepared them for portfolio careers, allowing them to leverage their decades of experience to command higher contracted rates than their younger counterparts. Furthermore, like fine wine, professional networks tend to get better with age. A 2017 study from LinkedIn found that 81% of contractors on its freelance marketplace Profinder cited word-of-mouth referrals and personal networking as their primary sources of work. With their social and professional networks already years in the making, boomers could have a leg up in scoring freelance jobs in the COVID-19 economy.


Boomers should consider scaling up gradually. They need to market themselves strategically and be conservative with spending at first. Some may not realize that physical office space is no longer necessary, especially in a post-COVID-19 economy. Furthermore, it may not even be worthwhile to make expensive investments in branding and website development initially. Reputation, network, a basic social media presence, a services brochure, and a compelling white paper might be all they need to launch a portfolio career.

Gen X is ready to embrace new career horizons

Gen X’s reputation for being cynical and antiauthoritarian may not just be a stereotype when it comes to their experience in the traditional workplace. According to LinkedIn Learning, Gen X is, by far, the generation most stressed at work. They’re also more likely than millennials to be “actively disengaged” with their jobs, according to Gallup. And, according to data from MetLife, only about two in three Gen-Xers say they are happy at work compared to 75% of millennials and 74% of boomers.

With stronger levels of dissatisfaction building before COVID-19, it is safe to assume that this crisis may push Gen-Xers, in particular, to steer their careers in a new direction. According to data from BMO Wealth Management, 50% of Gen-Xers who have portfolio careers cite “having autonomy and control” as a top motivator for self-employment—the highest of all generations.

With an average of 20 years in the workforce, Gen-Xers boast an impressive combination of business experience, soft skills, technical skills, and established connections to help them thrive in portfolio careers. They may be the most well-balanced of all the generations currently in the workplace, a trait that could prove advantageous in the post-COVID-19 economy.

Despite the reputation for the cynicism of hierarchy, Gen X accounts for 51% of leadership roles globally, according to DDI World. This means that many Gen-Xers are already in stable, successful roles. Those who want to pursue a portfolio career instead should make sure they are first mentally and financially able to leave, with an alternative plan ready to execute. They need to make sure not to risk current employment by having the conversation too soon, especially in the job market lag of COVID-19. To avoid cold feet, approach the exit conversation firmly committed to leaving. If they cannot commit, the timing may not be right.


It’s also critical to research any legalities that might impact transition, especially in the evolving regulatory environment of COVID-19. For example, noncompetes are very common in employment contracts, and it is necessary to be aware how this might limit a portfolio career.

Millennials are a recession-proof brand

As the children of parents whose jobs and nest eggs became increasingly less secure in the 2000s, millennials entered the labor market amid the global financial recession and have experienced record unemployment, rapid digital transformation, and rising demand for new skills that are constantly evolving.

The economic despair of COVID-19 may conjure up sore memories from years’ past, but many millennials will be able to draw from the lessons they learned from starting up in a down economy. In particular, they’ve learned the value of constantly reskilling and not placing all their eggs in one basket. According to data from Bankrate, about half of millennials already have a side hustle, which challenges them to keep expanding their skill set and diversifying their career goals.

While millennials have an oft-cited reputation for being lazy, the data tells quite a different story. Millennials are willing to work as hard, if not harder, than the other generations: 73% report working more than 40 hours a week and nearly 25% work over 50 hours, according to a global study from ManpowerGroup. And the same study found that, while millennials still favor full-time employment, over half say they are open to nontraditional forms of employment in the future.

With only a few years of a steady paycheck–and many still paying off student loan debt–it is important that millennials are prepared financially to make the move into a portfolio career. This means either having projects lined up that will bring in immediate cash flow or having a cushion until they begin generating incoming. This cushion should be at least three to six months, but it may be better to have more in some industries. It’s also important to have health, life, and business insurance to remain fully protected in the absence of full-time employment.


Some other challenges facing millennials are perceived inexperience and escalating competition. They’ll likely be entering a field where consultants in their 40s and up have multiple decades of experience—and there might be a few hurdles to get over before landing that first client. This is where business planning and professional development become crucial for millennials.

Before beginning on a portfolio career journey, it is very important to strongly develop an identifiable, marketable area of expertise. After all, clients expect more knowledge, resources, and capabilities than they themselves have, and preferably a niche offering rather than something broad. A general range of expertise, such as marketing, won’t be distinguishing enough. But digital marketing for small businesses may help bring in clients, especially in the COVID-19 where most business networking has moved online. Finding a suitable and profitable niche can be challenging but, with enough due diligence and creativity, it is possible to carve out a niche and captivate the interest of prospective clients.

Zoomers want to be their own bosses anyway

Even before COVID-19 disruptions, many professionals from the youngest generation entering today’s workforce were heading toward portfolio careers rather than full-time traditional jobs. In fact, nearly half of Gen Z or “zoomers” workers are already freelancers—and this number is only projected to grow in the next five years, according to a report from Upwork. This same report found that 73% of zoomers freelance as a lifestyle preference rather than out of financial necessity, compared to 64% of millennials and 66% of boomers.

Zoomers are digital natives and have grown up in a tech-driven world. The oldest members of this generation were just 12 years old when the first iPhone was released. Having been immersed in technology their whole lives, zoomers have many of the technical skills highly in demand in today’s marketplace. And this is a generation that values reskilling and lifelong learning. According to data from LinkedIn, 67% of Gen Z professionals feel that the skills necessary to succeed in today’s workforce are different than those in previous generations.

Apart from having marketable technical skills, zoomers will need to refine their soft skills and other attributes necessary to succeed in a portfolio career. These include a strong work ethic, focus, confidence, tenacity, and the ability to strategically network.


With fewer years under their belt, it may be helpful for zoomers to start their portfolio career as a part-time endeavor. Moonlighting tests the ability to be independent while still retaining a full-time gig to gain expertise, develop a professional network, and become more financially stable.

It’s also helpful for zoomers to develop relationships with advisers and mentors. This trusted network can provide valuable guidance and feedback. A trusted mentor can help test and refine a plan for a portfolio career. They can also provide useful insights and perspectives on what is in demand in the marketplace and how to best apply skill sets.

The future of work

In the current COVID-19 landscape, half of companies are considering layoffs as a long-term operational strategy. But what happens when the post-COVID-19 recovery begins and companies need to rehire?

The trend toward contracted freelance work has been making waves in the global economy, even before COVID-19 sent many of us home. Freelancers are the fastest-growing workforce segment in the European Union and, in the United States, freelancers will represent more than half the nation’s workforce by 2027. In the Asia Pacific region, 84% of hiring managers are outsourcing work to freelancers, and 79% say a more flexible workforce will help companies navigate an increasingly globalized business climate.

As COVID-19 disrupts the global workforce and prospects for contracted work continue to outpace employment growth, it is possible that many of the jobs lost will be filled by portfolio career seekers–across all generations–looking to develop multiple skill sets, follow new passions, achieve personal growth, or simply enjoy the change of pace.


Sunshine Farzan is an award-winning marketing veteran and dynamic career coach with nearly two decades of global integrated marketing expertise to help executives design personal branding strategies that support corporate growth objectives and achieve omnichannel engagement.