The question that has transformed my coaching (and life)
“Where do you want to be in five years?”
It’s a simple question, maybe even an obvious one. But over time, I’ve found it to be one of the most powerful questions we can ask young people as they move through early adulthood. It’s also a question I’ve asked organizational leaders, peers, and loved ones I’ve coached, both formally and informally. And it’s a question I return to myself at least once a year.
Why is it such a powerful question? For a few reasons. First, it’s uncomfortable. In school and work, we’re often good at setting short-term goals and imagining big-picture dreams. We know how to think about what we want next week, next semester, or someday far off in the future.
But the in-between is harder.That five-year space, that’s not immediate and not forever, sits right at the edge of what many of us are practiced in imagining. High school and college are structured around four-year timelines. Beyond that, we think in yearly resolutions, quarterly goals, KPIs, and questions like, “What do I want to be when I grow up?”And then adulthood arrives, and many of us still don’t know. I don’t think that’s because we’re lost. I think it’s because we don’t spend enough time building those middle-mile markers, the milestones that connect today’s decisions to tomorrow’s life.
I was reminded of how transformative this question can be on a random Wednesday in February. That day, I had three different conversations, all grounded in the same framing: five years from now.
The first was with Cris, a college senior and Obama Foundation Voyager Fellow. Cris has worked tirelessly to support his community, his family, and his own growth through service, advocacy, leadership, and academic excellence. As soon as we started his coaching session, he very stoically informed me that he had been accepted into many graduate programs and fellowships he applied to. Over a dozen opportunities, and many more potential paths, are ahead for him. He felt excited and humbled by the acceptances, and unsure, even a little overwhelmed, by making the decision on what path to take. So I asked:
“Where do you want to be five years from now? What do you want to be doing? Where do you want to live? What do you want your daily life to feel like?”
He paused. He admitted he’d never really thought about life in that way. Then he began to describe a not so distant future: education policy work, staying connected to his family, experiencing new cultures, building financial stability. Suddenly, the decision in front of him wasn’t just about choosing the “best” program. It became about choosing what moved him closer to that five-year vision. And even if his reality is that many of the potential paths can move Cris in that direction, by the end of our call, I could hear the clarity in his voice, and see the relief settle in.
Later that day, I FaceTimed with Kiana, someone I’ve had the honor of mentoring for nearly a decade. We first met when she was in high school. Now she’s in her mid-twenties, navigating her first career-oriented role in youth development. She shared the mix of excitement and frustration that comes with being early in your professional life: learning organizational dynamics, managing burnout, trying to find balance. As a result, she was in a moment of uncertainty. After listening for a while, I asked:
“What do you want for your career five years from now? And how can this moment support you in getting there?”
As she talked, she realized she already had opportunities in front of her, training, potential roles, and pathways that could move her toward becoming a youth programming director – something attainable within five years. Furthermore, she clarified that working with and mentoring young people who shared similar lived experience to her was important, as well as continuing to cultivate financial stability. Again, nothing became instantly easy. But the path became clearer. “These young people keep me going,” she said as we closed out the conversation. Not only did that resonate with me on a personal level, but it was a signal that she’s on the right path. Now she’s got some decisions ahead and a five-year vision to measure them against.
Finally, there’s the ongoing conversation I have with my mom. She’s in her mid-seventies, and entering a new chapter of life, one no longer defined by raising a son and working to provide for our family. She did that. Many of the lifelong goals that once gave structure and purpose have been accomplished, and yet, there is still so much life ahead. So I ask her, and often do:
“What do you want life to be like in five years?”
She’s still figuring it out. But week by week, her vision becomes a little clearer: having enough financial security to no longer work full-time, having the time and energy to explore hobbies, travel a bit more (our Copenhagen trip is on the horizon), and still be fit enough to go on walks, stay connected to her community, and maybe even volunteer a bit. And each time I ask the question, I hear the excited curiosity in her voice and she considers what’s next.
That’s the power of the question. Five years is far enough away to invite possibility, but close enough to shape action. It helps us make decisions with intention. It turns uncertainty into direction. And it reminds us that no matter what stage of life we’re in, we’re still allowed to dream what’s next.