Fractional Executives Enjoy Multiple Income Streams with Portfolio Careers

By Bill Ellermeyer, Executive Career Strategist, Ellermeyer Connect
The iconic CEO of GE, Jack Welch, once advised: “Change before you have to."
No Gold Watch
The way we work today differs from how our parents used to work. It’s now uncommon to hear of someone retiring after 30-40 years with the same company and receiving a gold watch. In fact, the U.S. Bureau of Labor Statistics states that the average person is expected to hold ten different jobs before turning forty, and this number is likely to increase.
As a result of this shift from past work practices, today’s professionals are actively adjusting their involvement in the job market. Workers are adapting to the new norm. Instead of waiting for the inevitable end of traditional, single full-time employment, they are taking control by diversifying their job opportunities (and income) through multiple sources of work engagements.
A single job is no longer enough. Fractional work is becoming more common, either as an addition to a conventional job or as a foundation for creating a new work-life balance.
In the last 15 years, the work environment has been continuously evolving. Traditional workplaces have become less stable, and senior executives are feeling more at risk. This trend is being accelerated by Artificial Intelligence, the “silent job eliminator” that is rapidly replacing professional roles.
Emergence of the Gig Economy
This noticeable shift has led to the expansion of the “Gig Economy.” Independent workers now make up around 35% of the global workforce and 36% of the U.S. workforce. It is estimated that by 2027, over 50% of the workforce will be independent.
More and more, executives are transitioning into what I refer to as the “Portfolio Career” model, allowing them to leverage their core skills and experience across multiple income streams. This is often built on fractional roles such as CFO, CMO, or CTO —serving as the foundation from which executives can build a portfolio of additional income-generating activities. Here are five examples of how an executive might structure their portfolio:
- Fractional CxO. Serving multiple companies as a C-Level executive one day (or several days) per week.
- Adjunct Professor: Teaching courses at a nearby college or university.
- Board of Directors: Participating as a member of the board (or on multiple boards) of a startup, public company, or non-profit organization.
- Marketing a Training Course: Developing and selling a training course based on one’s professional expertise.
- Coaching: Providing executive leadership and performance coaching to multiple clients.

These examples are most suitable for individuals who engage in fractional (i.e., long-term, part-time) work as their foundation. However, those with traditional corporate roles and more limited time can still pursue a Portfolio Career. For instance, they might begin by teaching one class per week, which could gradually expand to multiple evenings as they transition thoughtfully into a fractional leadership role.
This potential strategy is especially beneficial for executives over 50, helping them avoid the “in and out” cycle of corporate roles. At some stage, they must learn to operate independently, remain active in the professional sphere, and continue working well into their 80s and beyond. The evidence supports this—physical activity, mental engagement, and health are interconnected, and many prominent billionaires today remain active into their 90s.
For the professional workforce, it will ultimately become clear that shifting to “free agency” through a Portfolio Career is the optimal path. True job security often comes from pursuing an entrepreneurial approach, a strategy that has positioned the United States as a global leader in innovation and the delivery of new products and services.
As I’ve advised my clients and community for years, “You Are The Enterprise!
About the Author
Bill Ellermeyer of Ellermeyer Connect is one of the most recognized Executive Career Transition Consultants in Southern California. Bill regularly speaks about career management, entrepreneurship, and "un- retirement." He is a master connector who helps clients build relevant quality contacts, something he believes is the bottom line for every senior executive in transition. More than a career counselor, Ellermeyer acts as a personal agent to his executive clients, introducing them to powerful connections and helping them build portfolio careers. Hundreds of Orange County executives over the past 25 years have benefited from Bill's remarkable talent and solid expertise.
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