
Leap
10 minLeaving a Job with No Plan B
Introduction
Narrator: Imagine being at the absolute peak of your career. You host a nationally syndicated radio show with millions of listeners. It's the job you dreamed of, the one you worked decades to achieve. Then, one day, you walk into your boss's office and quit. With no plan, no backup, no idea what comes next. The immediate reaction from a friend on Twitter sums it up perfectly: "WHAT THE HELL ARE YOU DOING?!?!?!" This isn't a hypothetical scenario; it's the true story of Tess Vigeland, and it forms the heart of her book, Leap: Leaving a Job with No Plan B. The book is a raw and honest exploration of what happens when you step off the established path into the terrifying, exhilarating, and identity-shattering void of the unknown.
The Leap is Followed by an Inevitable Free Fall
Key Insight 1
Narrator: The decision to leave a stable, successful job is often preceded by a long period of internal turmoil. For author Tess Vigeland, her body knew it was time to go long before her mind fully accepted it. She describes the physical symptoms of stress—nausea, dizziness—that plagued her as she wrestled with the decision to leave her hosting job at Marketplace. The moment she finally handed in her resignation, a wave of euphoria washed over her. This initial high is a common experience for "leapers."
Wendy Harris, a successful securities litigator, felt a similar rush. After quitting the high-pressure law firm where she felt her work lacked meaning, she couldn't stop smiling. She planned to take a week off, a mini-vacation to celebrate her newfound freedom. But then, Monday morning arrived. For both Vigeland and Harris, the euphoria evaporated, replaced by a stark, terrifying thought: "Good Lord, what have I done?"
This is the "Oh Sh!t" moment—the pivot from exhilaration to panic. The unstructured reality of unemployment sets in, and the cultural discomfort with not having a plan creates intense anxiety. As INSEAD professor Herminia Ibarra explains, we are conditioned to believe that success requires a clear, linear path. When that path disappears, it’s not just a financial or professional crisis; it’s a psychological one. The freedom of the leap is immediately followed by the terror of the free fall.
Quitting Your Job Means Quitting Your Identity
Key Insight 2
Narrator: In modern society, the question "What do you do?" is often the first one we ask a new acquaintance. Our work has become inextricably linked with our identity. When that work is gone, who are we? This is the central crisis for many who leap. Vigeland, once a proud national journalist, found herself dreading social situations, fumbling for an answer to that simple question. For nearly a year, she would answer with what she used to be, a clear sign of her struggle to forge a new identity.
This isn't just about ego; it's about a fundamental sense of belonging and purpose. The book introduces a support group of fellow leapers in New York who called themselves the "North Stars," all searching for their new direction. One member, Wendy Harris, noted how difficult it was to stop introducing herself as a lawyer. Another, Kate, a former executive, articulated the group’s shared challenge: redefining success. She concluded that success had to be about happiness and satisfaction, not just money or external validation from others.
The book argues that to navigate this identity crisis, leapers must consciously detach their self-worth from their professional titles. This means shifting the focus from external validation—the job title, the salary, the approval of peers—to an internal barometer of success based on personal values, happiness, and fulfillment.
Society Stigmatizes Quitting, Making It Psychologically Difficult
Key Insight 3
Narrator: The phrase "Winners never quit, and quitters never win" is deeply ingrained in our cultural psyche. This stigma makes leaving a job, even a toxic one, feel like an admission of failure. The book challenges this notion, presenting quitting not as a weakness, but as a healthy, adaptive response. Author Peg Streep, who studies the science of quitting, argues that it’s a vital strategy when a goal is unreachable or a path is a dead end.
However, our brains are wired to resist. Behavioral economics studies show that going against the norm is inherently difficult. Furthermore, the "sunk-cost fallacy"—the feeling that you can't leave because you've already invested so much time, energy, and money—keeps many people stuck. Courtenay Hameister, a former variety show host, perfectly described this trap. She felt her job had become the most interesting thing about her, and "quitting my job without feeling like I was quitting myself" seemed impossible.
Overcoming this requires a powerful mental shift. It involves recognizing that past investments don't have to dictate future happiness and that separating one's identity from their job is crucial for making a rational, healthy decision to move on.
Leaping with Dependents Requires a New Definition of Security
Key Insight 4
Narrator: The decision to leap becomes exponentially more complex with a family to support. The fear of financial instability and the guilt of being "selfish" are immense. The book shares the story of Sibyl and Rob Chavis, two Harvard-educated lawyers with two young children. Despite their professional success, they were deeply unfulfilled. Their biggest obstacle to leaving was the thought, "But we have children!" Yet, they ultimately decided that modeling a life of passion and courage was more important than demonstrating a life of unhappy, albeit stable, work. They downsized, lived on savings, and took a calculated risk that paid off when Rob landed a job as a writer for an NBC sitcom.
Similarly, Aaron McHugh was motivated by the desire to provide for his family, especially after his daughter was born with severe disabilities. For years, he stayed in a stable but unfulfilling job for the health insurance. After his daughter passed away, the tragedy forced a reevaluation. He realized that true security wasn't a steady paycheck, but freedom. He had built up a "Freedom Fund" and used it to quit. He discovered he could make more money consulting in less time, and his biggest takeaway was a shift in priorities. As he put it, "I would love a new car with leather seats, but not as much as the freedom to say I’m not coming to work tomorrow."
The Path Forward is Paved with Experimentation, Not Just Planning
Key Insight 5
Narrator: While the book champions the leap, it doesn't advocate for recklessness. It presents a powerful cautionary tale in David Sobel, a man who quit his unfulfilling office job to become a writer but ended up severely depressed and financially ruined, soured on the idea of following his dreams. His story underscores that passion alone isn't enough.
The more successful leapers often followed a different model: experimentation. This is the idea that "doing comes first, knowing second." Rather than trying to think your way into a new career, you must act your way into it. Russ Kendall, a photojournalist watching his industry crumble, didn't just quit. He started a "Plan B" on the side: making and selling pizzas at a local farmers' market. When he eventually left his newspaper job, he already had a tested, viable business. His new venture was not a blind leap but a calculated step onto a bridge he had already started building.
This approach allows you to test new identities, acquire new skills, and build a narrative for your transition. It reframes the leap not as a jump into a void, but as a move toward a future you have already begun to explore.
Conclusion
Narrator: The single most important takeaway from Leap is that the modern definition of a career—a linear, upward climb on a single ladder—is a dangerously outdated concept. The book argues that true success is not found in a title or a salary, but in the courage to redefine your life on your own terms, even if it means stepping into terrifying uncertainty.
It challenges us to stop asking "What do you do?" and start asking "What makes you happy?" or "What are you passionate about?" The ultimate message is not a simple instruction to quit your job, but a profound call to action: to continuously evaluate your life, to dream even while you're in the dream, and to have the courage to leap when your internal compass tells you it's time, trusting that the net will, in some form, appear.