Featured on Strategic Thinkers Podcast™

Strategic Insight

"I'm the lady with nine jobs. Truly, I just collect jobs."

What We Learned

After being laid off from Facebook despite strong performance, Abby stopped treating any single job as secure and started building multiple income streams instead. She treats freelancing as a legitimate strategic move, not a fallback — advising people to start on marketplaces like Upwork or Fiverr to learn the market before shifting to direct client relationships and a real service offering. She also stays hands-on with execution rather than purely overseeing, which keeps her skills current as tools and platforms evolve.

Notable Observation

Abby's own scheduling chaos — juggling separate calendars for freelance clients and her startup — became the direct inspiration for CalPal, a calendar and time-tracking tool built specifically for independent professionals managing multiple commitments at once.

Why We Invited

I invited Abby Schommer because she treats freelancing and portfolio careers as a legitimate professional services practice, not a stopgap, and backs that up with the actual mechanics — service one-sheets, continuous business development, boundary-setting — that make a services-based career sustainable rather than chaotic.

Featured Conversation

Beyond the Layoff: Building an Unshakable Portfolio Career
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Abby Schommer has led growth strategy for companies ranging from pre-seed startups to Fortune 100 companies over more than 10 years. She’s the co-founder of CalPal, a tool that centralizes calendar and time management for independent professionals juggling multiple clients, and she practices what she teaches — running her own portfolio career as a marketing consultant for eCommerce and gaming companies. She also hosts conversations with industry leaders on her podcasts, Marginal (by CalPal) and Going Deep (with Plunge Games).

Co-Founder, CalPal & Marketing Consultant