Some days, it feels like you’re supposed to have your life mapped out already. You’re constantly asked what you want to study, what career you’re aiming for, where you see yourself in ten years. And sometimes, you have an answer. Other times, you don’t. The pressure of watching classmates seem so certain can make uncertainty feel like failure, like you’re already behind.
But when Seattle Prep alumni responded to that same question, from recent graduates to members of the class of 1997, a different image started to emerge. Not one person described a straight or predictable path. Instead, their stories were shaped by uncertainty, unexpected turns, and decisions made without knowing how things would turn out.
“I didn’t have a clear picture of what I wanted to do with my life when I was in high school,” said Mike Lovejoy (Prep ’04). “I knew I wanted to go to college, but I didn’t have a vision of what my life would look like beyond that.” Years later, even with a law degree, his plans shifted dramatically. Facing a difficult job market, he chose a completely different path, joining the Marine Corps, something he had “never previously considered.”
That kind of unpredictability wasn’t unusual. Chris Potts (’97) admitted that as a student, he was more focused on music and baseball than any long term career. “I thought I would either be a rock star or do something in baseball,” he said. Today, Potts founded The Bouldering Project, something he never originally planned. “I didn’t go to business school or have traditional certifications. My grandfather was an inventor, and we took everything apart and put it back together.” That mindset shaped how he approaches problems and ultimately how he built his career. Looking back, he describes his life as “a wild and enjoyable and exciting series of things unfolding in the most surprising and unpredictable ways.”
Even people who ended up in highly structured careers didn’t get there without setbacks. Ashley Alwood (’97), now a doctor, shared that she struggled early in medical school and had to repeat her first year. That experience, she said, forced her to rethink how she approached challenges. “Failure has been a better teacher than success.”
For Kevin Uno, those challenges are part of a much bigger perspective. As a scientist and professor at Harvard, he says he has “failed so many times at so many things” that it has become essential to how he approaches both research and life. Rather than avoiding failure, he sees it as proof that you can “pick yourself up and get back to whatever it is you care about.”
But not every story is defined by a single setback. For Asta Wylie (’17), the uncertainty came from having too many possible directions. Torn between artistic and academic interests, she chose to take a gap year and move to Nashville to pursue music. What shaped her path most was not one decision, but a willingness to explore. “I’ve worked in a wide variety of jobs, and each experience helped me weed out what I didn’t want and get more intentional about what I was looking for.” Instead of trying to predict outcomes, she focused on something more stable. “I try to tie my decisions to my values rather than worrying about the outcome.”
Others described moments when their identity had to completely shift. Victor Steinbrueck (’07) saw himself only as a basketball player in high school. “My entire identity was tied to playing basketball,” he said. When that path didn’t work out, he found himself struggling to move forward while others around him seemed certain. Over time, that uncertainty pushed him to grow in a different direction. What stayed with him most was not a specific plan, but a mindset. “I’m not sure much scares me more than looking back and regretting not having given myself the chance.” That fear of regret became a motivator to take risks even without guarantees.
For Marc Dela Cruz (’97), now a Broadway actor known for performing in Hamilton, the uncertainty itself is the point. “You don’t know, and that’s the beauty of it,” he said. “I don’t want to know what comes next. That would ruin the surprise.” Instead of trying to control the future, he focuses on experiencing it fully.
If there’s one thing these stories make clear, it’s that very few people actually know what their future holds. But that doesn’t mean they’re lost. Instead of focusing on having everything figured out, they focus on what they can control.
Ashley Alwood described making important decisions by asking simple questions. “Does this fit my values? Does it move me in a better direction than where I am now? Will I be okay with this choice in five or ten years, even if it’s hard?” Rather than planning everything, she focused on choosing the next step that felt meaningful.
Brianna Chiodo (’97), currently a tech manager for Starbucks, took a similar approach. After realizing her original academic path in science wasn’t the right fit, she began exploring classes that interested her and discovered a passion for people, culture, and connection. Her career eventually grew from those interests. Looking back, she emphasizes that “your decisions and experiences can lead you to a totally different path than you thought you’d be on and that’s okay.”
For Trey (’19), who is preparing for law school, the balance between certainty and uncertainty is something he experiences every day. Some moments feel clear, especially when he thinks about his goals. Other moments are filled with unknowns, like where he will live or how his field might change. Still, he focuses on what remains steady. “The things I can control, my faith, my love for my family, the effort I put forth every day, are all strong and will remain that way.”
Across generations, that mindset stays consistent. You may not be able to predict the future, but you can prepare for it.
“I can’t predict where I’ll end up,” Mike Lovejoy said, “but I can make sure I’m ready for wherever that is.”
That idea might be the closest thing to an answer. The future is not something people figure out once and for all. It takes shape over time. Plans change. Interests shift. Setbacks happen. But through all of it, people keep moving forward, one decision at a time.
For students who feel unsure, that might not be the answer they expected. But it might be the one they need. You don’t have to know exactly where you’re going. You just have to be willing to take the next step.
