Should a Five-Year Plan Be Part of Your Five-Year Plan?

   Image:      Levo League

Image: Levo League

By: Katie J. Cartwright, GWWIB VP of Communication

Originally published on

Since high school, I’ve been no stranger to the idea of constructing the perfect five-year plan. Parents, family friends, and professors encouraged me to “think big” and dream up a grand scheme of how my life would look in the next half-decade. Where will I go to college? Once I’m in college, what will I major in? Where will I intern? Will I study abroad? At the end of it all, where will I accept my first ever full-time job? Where will I build my life?


At GWWIB’s Sixth Annual Spring Conference, Gillian Gorman Round, President of The Lucky Group, told us to do something I’d never heard before: “Rip up your five-year plan right now, because it’s not happening. And that’s a good thing.” After that, I started hearing the same message in career development articles, at internship events, from career coaches.


Who wouldn’t be left wondering whether a five-year plan should be, well, part of their five-year plan?


I think the need for a five-year plan comes down to a having sense of determination, passion and confidence, which develop with time and practice. A five-year plan is a great tool when you’re young, learning what you love and what you want to do in your career. As I’ve gotten older, I’ve parted from the plan I originally made for myself. I trusted my drive and passions to lead me in the path that was right for me. As I’ve gotten older, inevitably, my five-year plan evolved past a few dates and bullet points.


In the past year, I’ve held three Board positions with GWWIB, interned in NYC for a summer, and started my own blog  – three things that I never considered making part of my five-year plan, but that I know are taking me to where I want to be.