Beyond The Side Hustle: How Execs Are Redefining Freelance Work
While it hasn’t generated the same attention as quiet quitting, career cushioning or resenteeism, we’re living in the era of another notable workplace trend: side hustles. Senior executives who occupy full-time, often demanding roles within companies are now pursuing part-time gigs as well, often as part of a portfolio career. Some may be open about these side projects, viewing them […]
While it hasn’t generated the same attention as quiet quitting, career cushioning or resenteeism, we’re living in the era of another notable workplace trend: side hustles. Senior executives who occupy full-time, often demanding roles within companies are now pursuing part-time gigs as well, often as part of a portfolio career. Some may be open about these side projects, viewing them as the extension of a “passion;” others may be more private about their enterprise.
But they are definitely doing it. Data shows that nearly 40% of working adults in the United States have this kind of “side hustle” and even more believe that they need one. Anecdotally, I can report that a significant number of executives with whom I interact are actively engaged in some kind of project outside of their full-time role, and they are not looking to pare down.
The options for these side gigs are limitless. These executives do not feel in any way bound to their “main” industry. From public-facing roles (paid speaking, book deals, teaching, strategic advising, board services), to operating a small-scale family business or a franchise (farming, real estate, restaurants), to roles that leverage expertise they’ve gained in their main job, albeit not necessarily in the same fields (tech consulting, fundraising for a charity), these execs are stretching the bounds of what a “job” looks like, and redefining the idea of freelance itself.
Examining A Trend
Multiple factors are contributing to this trend of executives choosing to freelance. A notable one: changes to the gig economy itself.
Ten to 20 years ago, the gig economy was primarily attractive to younger folks, who in some cases had trouble getting a foothold in established industries without experience under their belts, and also had the stamina to weather less consistent, more hustle-driven work due (in part due to not yet having responsibilities such as families). These younger employees enjoyed the freedom of working outside of an office, on their own terms. However, with the pandemic, more senior career professionals experienced remote working—sometimes for the first time—and found it yielded new levels of personal productivity, along with a more desirable work-from-home lifestyle. The experience opened their eyes and appetite for new possibilities.
The gig economy itself—largely driven by the presence of digital platforms that allow workers to connect with contract, freelance or other short-term jobs, has grown two-fold in value in the past five years alone. This economy is expected to grow steadily worldwide, and one of the factors contributing to this phenomenon is the influx of more experienced professionals and executives into the gig work market. Particularly as businesses across the globe are navigating return-to-office expectations (some with extremely unpopular results), surveys suggest that more people are seeking flexibility.
A Surprising Focus
Interestingly, from what I’ve seen working with senior executives, the opportunity to make more money is not a primary motivator for the decision to engage in a side hustle. Rather, one of the strongest drivers is a desire for fulfillment and meaningful work, usually related to a deep personal passion, or the impulse to make an impact in a way they feel is not possible through their regular role. (For example, I talked with one corporate CFO who is passionate about education and teaching youth about managing personal finances.)
Another frequently mentioned reason is a desire to learn continuously and stay in touch with the latest industry developments, particularly for older, more seasoned executives who may be considering retiring in the next few years, but aren’t quite ready to do so yet. These executives may be driven to interim roles where they can focus on what they see as the most impactful part of their work, with an eye toward ultimately gaining a better work-life balance as they approach retirement.
A Changing Strategy
Aside from their own involvement in the gig economy, key decision-makers and employers within major enterprises are changing the prevailing view and utilization of “gig” talent. With a focus on restoring business productivity after the pandemic, companies are struggling to find and entice the right talent—at any level. In response, a new strategy has emerged: Focus on contingency/gig workers as a more flexible solution for uncertain, transient times. The so-called “invisible workforce” is here to stay, and executives are now looking for long-term solutions to manage these new types of contributors strategically.
For executives and non-executives alike, it is simply never too early to start thinking about impact beyond one’s current role. Even if they have no plans of retiring anytime soon, seasoned employees would do well to consider their strategy for a portfolio career, and what types of side hustles might be lucrative, enjoyable or impactful—in combination with a main role, or eventually, as the main role. Building one’s network, exploring board roles and nurturing meaningful interests are all productive efforts towards this end. The gig economy is here to stay; it’s important to have a plan in place.
Article written by: Orville Lynch, Jr.
Mr. Lynch, a member of the legendary two-time Ohio Civil Rights Hall of Fame Award winning Lynch Family.
Mr. Lynch is a nationally recognized urban media executive with over 20+ years of diversity recruitment and serial entrepreneur with numerous multi-million dollar exits.