Introduction

In a world where layoffs have become commonplace and job security feels increasingly elusive, Abby Schommer offers a revolutionary perspective: the traditional single-income career path isn't the only option—and may not even be the most secure. On a recent episode of the Strategic Thinkers podcast, Abby shared insights from her experience with layoffs at Facebook and her subsequent journey building a portfolio career, helping professionals reclaim control over their career trajectories and develop greater resilience in the face of uncertainty.

Layoffs: A Transformative Experience

Unlike conventional approaches that focus on quickly securing another full-time position after a layoff, Abby emphasizes looking at the broader opportunity for career transformation. "When you get laid off, it literally changes your life. It'll change the way you look at work for the rest of your life," she explains. This perspective shift becomes particularly valuable in today's workplace environment, where corporate loyalty is increasingly one-sided.
By acknowledging the reality that no job is truly secure, professionals can proactively build resilience through diversification rather than placing all their eggs in one corporate basket. "You have no control," Abby notes, referring to the layoff decision-making process. "You can be a top performer... it really has nothing to do with performance in most cases."

Portfolio Careers: Taking Back Agency

Abby's unique approach comes partly from her experience being laid off from Facebook in 2022 despite stellar performance ratings and recent career advancement. This unexpected shift led her to recognize the power of building multiple income streams.
"My career is literally the culmination of all of these different things that I have," she explains. "I'm the lady with nine jobs. Truly, I just collect jobs." This approach allows for greater agency and control over one's career trajectory, as losing any single income stream becomes less devastating when balanced with others.
The portfolio approach also offers protection from the whims of corporate decision-making. While you can't control whether any single client or employer will keep you on, you can control the overall umbrella of opportunities you develop and maintain.

The Power of Freelancing in Career Transitions

One of Abby's most counterintuitive insights challenges our culture's stigma around "side gigs": freelancing isn't just a stopgap measure but can be a strategic career move. Rather than viewing freelance work as a step backward, she positions it as an essential component of career development and security.
"There is this fallacy that you need to be all in on your business in order for it to be successful," she notes, highlighting how this mentality is "laden with privilege." Not everyone can afford to cut off all income streams while building something new.
For those transitioning after a layoff, freelancing offers immediate benefits:● Rebuilding confidence through quick wins● Creating income while searching for the next opportunity● Expanding professional networks● Developing new skills and staying current with industry tools

Understanding the Freelance Landscape

Abby advocates for a pragmatic approach to entering the freelance market: "Rather than getting overwhelmed or bogged down with the details of 'I need a website, I need an LLC,' let's make sure that you can appeal to clients and that there's a very clear value exchange."
She suggests starting on platforms like Upwork, Fiverr, or Pangea to gain experience and understand the market. While these platforms take a percentage of earnings, they provide valuable insights into job scopes, client needs, and competitive rates. Over time, freelancers can move to direct client relationships and referrals.
"I got my start on Upwork, worked with a number of clients through there. And then after time, I just started to build out my own services one sheet and reached out to clients directly," she explains. This gradual approach allows professionals to learn the business aspects of freelancing while still generating income.

Emotional Well-being During Career Transitions

Perhaps the most overlooked aspect of career transitions is the emotional impact. Abby addresses this head-on: "I think what's really powerful in a way that you can build confidence over time is by just continuing to remain open to opportunities."
For those supporting someone going through a layoff, she recommends a "listener-first approach," cautioning against immediate job suggestions or reassurances. "Don't try to reassure them that, you know, you heard this person got a job or 'don't worry, things will turn around' because inherently that can feel incredibly invalidating."
For those experiencing layoffs firsthand, she suggests:
1. Taking time to rebuild confidence before diving into applications
2. Finding quick wins through small projects or gigs
3. Focusing on networking rather than cold applications
4. Considering freelance or contract work as a pathway to full-time roles

Managing Multiple Clients: The Birth of CalPal

The conversation extends beyond freelancing strategies to address the practical challenges of managing multiple clients. Abby shares how her own portfolio career led to the creation of CalPal, a calendar management solution for independent professionals.
"I would have meetings thrown on my calendar for my freelancing clients. But then I would also have a completely separate calendar dedicated to my startup," she explains. The resulting scheduling conflicts and inefficiencies inspired her to create a tool specifically designed for those managing multiple professional commitments.
CalPal offers features like:
1. Calendar synchronization across multiple professional commitments
2. Time tracking analytics to identify how time is allocated across clients
3. Client budgeting tools to prevent overcommitment
4. Dynamic booking links that adjust availability based on time allocations
This tool represents a significant innovation for the growing segment of professionals managing portfolio careers, addressing challenges that traditional calendar solutions haven't resolved.

Learning Through Execution

A key benefit of portfolio work is the opportunity to remain hands-on with practical execution rather than becoming disconnected from implementation. Abby acknowledges that some might see this as a step back: "You might find yourself doing work through consulting that feels a little more executional than what you were doing prior."
However, she reframes this as an opportunity: "There's so much to be said for being hands on keyboard and being intimately familiar with the day-to-day of what it takes to do this job." This practical knowledge becomes increasingly valuable as tools and platforms evolve, ensuring professionals remain relevant in their fields.
"When I got back to running Facebook campaigns for my clients, I realized... so much had changed. There was so much additional automation. There were all these different campaign types," she shares, highlighting how this hands-on experience kept her skills current in ways that strategic oversight alone wouldn't have.

Building Business Development Habits

For sustainable success in a portfolio career, Abby emphasizes the importance of continuous business development: "Continue to build your pipeline of potential prospects. Never stop doing business development. Never stop content marketing yourself."
This proactive approach provides not only financial security but also increases professional confidence and negotiating power. "The beauty of continuing to say yes to opportunities is it helps you build your confidence and it builds your ability to say no," she explains.
By maintaining multiple opportunities in various stages of development, professionals gain greater control over which clients and projects they accept, leading to better alignment between work and personal preferences.

Practical Applications

For those looking to apply Abby's insights, several key practices emerge:
1. Start small and practical - Begin freelancing without the overhead of formal business structures2. Leverage existing platforms - Use freelance marketplaces to understand the landscape before going independent3. Build your service offerings organically - Let client needs guide the expansion of your services4. Maintain continuous business development - Never stop networking and prospecting, even when busy5. Track time investments across clients - Ensure compensation aligns with time commitments6. Set clear boundaries - Establish expectations early in client relationships7. Embrace execution - Value hands-on work as an opportunity to maintain relevant skills8. Create supporting systems - Implement tools like CalPal to manage the complexity of multiple commitments

Conclusion

In an era where job security has become increasingly illusory, Abby Schommer's approach offers a refreshing alternative. By reframing career development as a portfolio rather than a linear path, professionals can build resilience against market volatility while maintaining greater control over their professional lives.This shift represents more than a trendy career technique—it's a fundamental repositioning that places agency back in our hands. Rather than being at the mercy of corporate decisions and market fluctuations, we can proactively build diverse income streams that collectively provide both security and satisfaction.For professionals navigating today's complex workplace landscape, this perspective provides not only protection from sudden job loss but also a more fulfilling approach to long-term career development. As Abby reminds us, the goal isn't to eliminate all uncertainty but to focus our efforts where it matters most: the areas where we have genuine control.
Want to learn more about building a portfolio career and managing multiple professional commitments? Check out Abby Schommer's resources:
● CalPal: www.getcalpal.com - A time management solution designed specifically for independent professionals● Follow Abby on LinkedIn for insights on portfolio careers and freelancing strategies● Listen to her podcast on marginalized professionals for additional career wisdom