In a recent LinkedIn post, Ani Filipova discusses the concept of “career optionality,” using the example of fashion mogul Tory Burch to illustrate how previously acquired skills can be foundational for future ventures. Filipova’s analysis emphasizes that career transitions often involve leveraging, rather than discarding, past experiences.
Filipova introduces Tory Burch’s journey as a case study, noting that Burch did not initially train as a fashion designer. Instead, she built a robust career in public relations, marketing, and copywriting, working with prominent fashion houses. This period, Filipova argues, was crucial for developing industry insight.
“For years, she was learning the industry from behind the scenes. Then, at 37, she decided to use that experience in a different way.”
The Foundation of Transferable Skills
Filipova highlights that Burch’s early roles were instrumental in her later success. “PR taught her how to communicate. Marketing taught her how to understand customers. Working inside established fashion businesses taught her how the industry operated,” Filipova writes, underscoring that these were not “wasted years” but rather essential skill-building phases.
The core of Filipova’s argument is that career changes do not necessitate a complete erasure of past professional life. “We often think a career change means leaving our previous experience behind. Usually, the opposite is true,” she states. This perspective challenges the conventional notion that a new career path requires a complete restart.
Defining Career Optionality
Filipova defines career optionality as the state of possessing sufficient skills, relationships, reputation, and experience to pursue multiple credible directions, rather than having a single, predetermined next step. This contrasts with the pressure many feel to identify one perfect career move.
“The job may change. The industry may change. Even your professional identity may change. But the experience travels with you.”
She poses a thought-provoking question to her audience: “If your current role disappeared tomorrow, how many credible directions could your experience take you next?” This question directly prompts readers to assess their own “career optionality.” According to Filipova, understanding this is key to navigating professional uncertainty and seizing new opportunities.
Assessing Your Own Optionality
To help individuals evaluate their own professional flexibility, Filipova has developed a “Career Optionality Score.” This tool is designed to reveal the extent of an individual’s current optionality and identify areas where they might be overly reliant on a single career path.
“That is what I mean by career optionality. Not having one perfect next move. Having enough skills, relationships, reputation and experience that you have several.”
Filipova’s post serves as a compelling reminder for professionals to recognize and cultivate the transferable value of their experiences, positioning them for greater adaptability and choice in their careers.
📝 About This Content
This article is based on insights shared by Ani Filipova on LinkedIn.
📅 Originally posted on October 3, 2026 | View original post on LinkedIn →