This month, I’ve been lucky enough to attend two graduations—and I have another one this weekend! It’s hard not to get swept up in the excitement, hope, and possibility that fills the air at these ceremonies. It also got me thinking about some of the most iconic commencement speeches ever delivered. Whether you’re crossing a stage, cheering in the audience, or reflecting on your own journey, the wisdom from these speakers still resonates.

In life—and in real estate—there are moments that feel like turning points. A new job, a big move, a dream home, or a child heading off to college. Graduation season reminds us that change is both inevitable and beautiful. And the best speeches offer inspiration not just for students, but for all of us navigating the unpredictable paths of adulthood.

Here are a few of my favorite commencement speeches, and the timeless truths they offer:

💡Steve Jobs – Stanford University, 2005

“Stay hungry. Stay foolish.”

Jobs’ address is arguably the most replayed commencement speech of all time. He didn’t lecture about Apple or innovation—he told three stories from his life. One about dropping out of college, one about getting fired from the company he started, and one about facing his mortality. What made it powerful? Honesty. Vulnerability. Simplicity. Jobs reminded us that life is short, and following your curiosity—even when it doesn’t make logical sense—often leads to the most meaningful chapters.

💡 Oprah Winfrey – Harvard University, 2013

“Failure is just life trying to move us in another direction.”

Coming from someone who has achieved extraordinary success—and faced more than a few setbacks—this message felt real. Oprah talked about owning your story, getting up when life knocks you down, and finding purpose through service to others. It was a beautiful reminder that even when things don’t go as planned, we’re being redirected—not rejected.

💡 David Foster Wallace – Kenyon College, 2005

“This is water.”

Wallace’s speech didn’t go viral right away, but it’s become a cult classic. His message was quiet, reflective, and deeply philosophical. He spoke about the grind of everyday life and the importance of choosing awareness and compassion over autopilot. “This is water” became a metaphor for seeing the invisible structures around us and choosing how we react. A little heavy, maybe—but oddly comforting, too.

💡 Sheryl Sandberg – UC Berkeley, 2016

“Option A is not available. So let’s just kick the hell out of Option B.”

After the sudden loss of her husband, Sandberg gave a raw and honest speech about grief, resilience, and moving forward. She didn’t sugarcoat anything—and that’s what made it resonate so deeply. Her words remind us that life doesn’t always go as planned, but we are still capable of finding strength, meaning, and even joy on the other side of heartbreak.

💡 Barack Obama – Howard University, 2016

“Change requires more than righteous anger. It requires a program, and it requires organizing.”

Obama delivered a passionate and pointed message about identity, activism, and responsibility. Speaking to a historically Black university, he urged graduates to honor their heritage while also stepping up as leaders. It was a speech about power, potential, and the importance of doing the work—not just dreaming about it.

Graduations aren’t just for the young—they’re for all of us. They’re a reminder to reflect, to celebrate growth, and to keep moving forward, even when the path isn’t clear.

Whether you’re embarking on something new, helping a loved one spread their wings, or simply navigating your own “Option B,” I hope these words offer a little spark of inspiration.

And as always, if there’s a milestone ahead that involves a change in address, I’d be honored to help guide you through that next chapter.

Cheers to growth, gratitude, and great speeches!

XX,

MG