Rethinking the ‘Five-Year Plan’ Question
Why This Question Needs a Makeover
It’s a question we’re asked over and over again. Just graduated? Job hunting? Interviewing? Retiring? No matter the milestone, someone will inevitably ask: Where do you see yourself in five years?
Regardless of the context, the expected answer is rarely about you. It’s focused on what you’ll do, how you’ll perform, and how you’ll conform to a predetermined idea of success. You’re expected to have a polished, linear plan that checks the boxes, provides a sense of ambition, and makes them feel comfortable.
The problem? The expected answer is limiting and performative, and can point towards goals that you may not align with. And, before you know it, that answer becomes your reality, one that is misaligned and produces an unfulfilling career and lifestyle.
Flip the Script
What if you answered the question differently? What if you focused your answer on how you want to be living, and how work will support that, in five years? What if your answer was about where you (not others) see yourself in five years?
These questions or where I often start my work with clients. In this approach, the job title, salary, retirement plan, and type of work become tools, not destinations. They support a path that reflects your values, priorities, and vision.
To begin answering the five-year question on your terms, clients and I start here:
What kind of lifestyle do you want to be living in five years?
Who do you want to be?
What kind of activities and experiences do you want to have?
What kind of relationships do you want to have?
How can work support and facilitate this vision?
How does your current or prospective job help you move closer to this vision?
These aren’t always easy questions. They require honesty, reflection, and often, a realignment of priorities. But the clarity that follows is worth it.
What Happens Next
When you answer the five-year question from a place of intention, it stops being about checking someone else's boxes and becomes about defining your own. It’s no longer about making others comfortable, but about creating a life that brings you clarity, joy, and success defined on your terms.
Over the years, through coaching, training, and leadership development, I’ve seen what happens when people take agency over their five-year vision. Clients begin to shift how they work, what they pursue, and how they relate to themselves and others. Instead of chasing the next job title, they begin crafting lives that feel purposeful. The titles and success follow, but this time in service of their vision, values, and lifestyle, not in place of it.
Your Turn
So, where do you see yourself in five years? How do you want to be living and working?
If you’re ready to explore what that looks like, let’s connect! Through the program From Stuck to Strategic, I partner with women to rediscover and refresh their vision for their next five years and beyond.
