Flirting with Possible Selves
Discover who you are by acting, not just thinking
Herminia Ibarra's research on career transitions found that the standard advice, to reflect deeply and develop a plan before acting, is backwards. People cannot discover their professional identity through introspection alone because they cannot know what they want until they have experienced it. Instead, successful career changers engage in a process Ibarra calls 'flirting with possible selves,' testing out different identities through small experiments before committing.
This framework rejects the idea that everyone has a single true calling waiting to be discovered through reflection. Instead, identity and interests are developed through action. You learn who you are by doing different things, noticing what resonates, and iterating. This is fundamentally different from the 'plan and implement' model taught in most career advice.
The research aligns with findings that personality changes throughout life far more than people expect (the 'end of history illusion'), that the matchup between person and career matters enormously, and that late specializers who explored broadly before committing are less likely to end up in mismatched careers.
- You cannot figure out who you are or what you want through introspection alone; identity is developed through action
- Successful career changes happen through small experiments and iterations, not grand plans
- Personality and interests change significantly throughout life, making early rigid commitments risky
- Match quality between person and role matters more than seniority or time invested
- Quitting a bad fit is not failure; it is optimization
- Design small experimentsInstead of planning your ideal career in the abstract, create small, low-risk experiments that let you test different possible directions. Volunteer, take on a side project, shadow someone in a different role, or take a course in an unfamiliar field.Pro tipHerminia Ibarra calls these 'identity experiments.' They should be small enough to be reversible but substantial enough to give you real information.
- Act first, reflect secondDo not wait until you have a complete plan or certainty about what you want. Act, observe your reactions, and then reflect on what you learned. The standard advice to 'follow your passion' assumes you already know your passion; most people need to discover it through experience.Pro tipEconomist Steven Levitt found that people who made major changes when uncertain were happier six months later than those who maintained the status quo. When in doubt, lean toward action.WarningThis does not mean acting recklessly. It means acting in small, reversible ways to generate information.
- Evaluate match quality signalsAfter each experiment, assess: Did this energize or drain me? Did I learn quickly? Was I intrinsically motivated? Did I lose track of time? These signals are more informative than abstract self-assessment.Pro tipPay special attention to the activities you find yourself doing voluntarily on your own time. These reveal genuine interest rather than obligation.
- Let go of sunk costsDo not stay in a mismatched career just because you invested years in it. Economist Seth Godin argues that we fail to quit the things that are not working because we confuse persistence with identity. Strategic quitting is a skill.Pro tipWest Point research showed that cadets with the most grit persevered through the initial hazing (Beast Barracks) but later left the Army at disproportionate rates because their rigid persistence trapped them in mismatched careers.WarningThe sunk cost fallacy is powerful. Just because you spent years getting a law degree does not mean practicing law is right for you.
Hesselbein never planned to be a leader. She volunteered to lead a Girl Scout troop because no one else would, discovered she loved it, and progressed through a series of unplanned roles. She became CEO of the Girl Scouts, was called the best CEO in America by Peter Drucker, and received the Presidential Medal of Freedom.
Before becoming a painter, Van Gogh failed as an art dealer, a bookshop clerk, a schoolteacher, a university student, and a missionary in a coal mine. He did not begin painting until age twenty-seven and did not produce his masterworks until his thirties.
Ibarra, a professor at INSEAD business school, studied professionals making major career changes and found that the successful ones did not follow the conventional plan-then-act model. Instead, they tested new professional roles through small commitments: short assignments, volunteering, side projects, and conversations with people in different fields. Paul Graham, Y Combinator cofounder, gave similar advice in a graduation speech: do not plan too far ahead, because you cannot know what you will want until you have more experience. Epstein weaves in stories of Frances Hesselbein (who led the Girl Scouts after a lifetime of unplanned pivots), Van Gogh (who tried and failed at multiple careers before painting), and Phil Knight (who set out on a worldwide trip with no long-term plan and ended up founding Nike).