365 Squarey Monsters: Are Today’s Graduates Ready for What Comes Next?

Sunday, May 31, 2026

Are Today’s Graduates Ready for What Comes Next?

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Are Grads Ready for What’s Next?

Across the country, graduates are walking across stages and into new chapters — from high school to college, from college into careers, and into adulthood. They deserve the applause and every word of encouragement for what they’ve worked so hard to achieve.

This season also carries an uneasiness about what comes next. The Class of 2026 is stepping into a world being reshaped by artificial intelligence, shifting career paths, and questions no commencement speech can answer. Still, there’s reason for hope.

👉 See why graduates may be more prepared than we think

My Message to Graduates

When I’m invited to speak to a graduating class, I always find it amusing. My path was anything but tidy. It included college in New Jersey, then New York, running St. John’s Home for Boys, bartending on weekends, and eventually buying a flower shop I didn’t quite know how to run.

But there’s a message in all those stories: believe something bigger is possible, stay curious, work hard, and be deliberate about the relationships that will shape your life long after the ceremony ends.

👉 Read the message I shared with graduates

In this week’s Power & Impact, Eric Ries, author of The Lean Startup and Incorruptible, joins me to ask a question every growing company faces: How do you keep success from becoming the thing that pulls you away from your purpose? Eric argues that companies don’t lose their way all at once, but drift through short-term pressure, narrow metrics, and decisions that put spreadsheets ahead of people. WATCH OUR CONVERSATION.

IN CASE YOU MISSED IT: In last week’s Celebrate Your Story , I spoke with entrepreneur Eliza Blank about building The Sill into a category-defining brand, the personal cost of ambition, and the path that led her to Farm Link, where she’s helping rescue hundreds of millions of pounds of surplus food for the 48 million Americans facing food insecurity. WATCH NOW.

One of my favorite parts of writing this letter is hearing from you — your stories, reflections, and the moments that connect us all. As we head into summer, I’d love your help with a few upcoming editions of the Celebrations Pulse

What are your summer plans? Whether you’re heading off on a big adventure, planning a quiet staycation, or doing something wonderfully unexpected, I’d love to hear about it. I’ll be selecting a few stories to feature as we celebrate the start of the season.

Let’s celebrate Amazing Dads. With Father’s Day coming up, I’m gathering stories about dads who’ve made a lasting impact — your own dad, a father figure, or someone in your community who deserves recognition. Tell me what makes them amazing.

👉 Share your stories