Stop Waiting, Start Living

What if you stopped waiting for “someday” and started checking off your bucket list now? That’s exactly what Jeremy George did—and not just once in a while. He crossed off 52 bucket list items in 52 weeks. His story is way more than a thrill-seeking adventure—it’s a wake-up call to reconnect with what actually matters: purpose, people, and being fully alive.

Here’s how Jeremy turned a dark season into a life-affirming mission—and how you can too.

From Rock Bottom to BucketMatch

Jeremy wasn’t chasing excitement when he created BucketMatch, a platform that helps people connect over their dreams. He was battling depression. From the outside, things looked good: New York City life, a recent promotion, financial security. But inside? He felt lost.

Then his mom nearly died. That moment, paired with a pandemic layoff, forced him to ask the question most of us avoid: If life ended tomorrow, what would I regret not doing?

Instead of spiraling, Jeremy grabbed a notebook and wrote down every dream he’d shelved. Then he gave himself a bold challenge: do one bucket list item every week for a year.

What Is Bucket Match?

Think of BucketMatch as part goal-setting tool, part social network, and part accountability buddy. You create a profile, list out everything you want to do before you die, and then the platform matches you with people who share your goals—or who’ve already done them and can help you.

Why? Because we’re wired for connection. Research from Cornell University shows that most people regret what they didn’t do in life—not what they did. And simply sharing your goals with someone makes you nearly twice as likely to achieve them.

So if you’ve ever wanted to skydive, write a book, or learn to dance but keep putting it off... BucketMatch might be your crew.

The Top 5 Lessons Jeremy Learned Chasing 52 Dreams

Jeremy’s year of saying yes wasn’t perfect. In fact, he “only” completed 32 out of 52 goals. But the lessons? Priceless. Here are his top takeaways:

1. Face the Hard Truth: Life Is Finite Sounds intense, but thinking about death helps you focus. What really matters? What do you not want to miss?

2. Don’t Just Dream—Document Write your goals down. Add photos, quotes, journal entries. Make them real.

3. Find a Partner in Crime Goals get way more fun (and likely to happen) when you invite someone else in.

4. Make Your Goals SMART That means Specific, Measurable, Attainable, Realistic, and Time-bound. Vague dreams = no action.

5. Celebrate the Fails Trying > perfect. One goal was to turn $1,000 into $10,000 in 24 hours by gambling. He lost. But the story? Gold.

The Power of Facing Mortality

Jeremy’s biggest mindset shift came from staring death in the face—not literally, but by asking: What would I regret not doing if I died tomorrow?

That single question flipped a switch. Suddenly, life wasn’t about climbing ladders or checking society’s boxes—it was about living on purpose.

And if you’re young or feel like “death is far away,” he suggests using other “mini-deathbeds”—like the end of a school year, job, or relationship—as prompts. What are you postponing that matters most?

Don’t Just Write a List—Make It a Vision

Jeremy didn’t just jot down “bike the California coast.” He made it a mission. He researched the route, printed out photos, saved travel tips, and wrote why it mattered to him.

One of his most meaningful goals? Meditating for 90 days straight. It helped him manage his mental health and build inner strength.

The more personal your list is, the more powerful it becomes.

Why You Shouldn’t Do It Alone

For every goal, Jeremy brought someone along. Sometimes a friend, sometimes a total stranger. That choice added depth and joy to every experience.

One standout moment: cliff jumping in Hawaii. A friend who couldn’t swim joined him (safely!)—and ended up loving it. Moments like that, Jeremy says, made the journey unforgettable.

Even during his 90-day meditation streak, he had a group of friends checking in. That’s how you build habits that stick.

Failure Is Part of the Win

Jeremy didn’t hit all 52 goals. And that’s OK.

The failed goals came with their own stories and laughs. Like trying to make $10,000 overnight or learning a language in a month. “Failing” helped him grow—and gave him great dinner party material.

Start Your Own Bucket List (Today, Not Someday)

Feeling inspired? Good. Here's how to begin:

1. Think About the End Ask yourself: What would I regret not doing?

2. Write It Out Go beyond the basics. Why does this matter to you?

3. Get Specific Turn “travel more” into “hike the Dolomites by summer 2026.”

4. Share It Tell a friend or join a community like BucketMatch.

5. Take One Small Step Sign up for a class, buy the gear, book the ticket. Movement matters more than perfection.

Final Thoughts

Jeremy George’s story reminds us that life isn’t about perfection—it’s about intention. It’s about connection. And it’s about squeezing as much meaning and joy out of the time we have.

Whether your dream is to run a marathon or finally forgive someone, the magic happens when you start.

Learn more about BuckMatch on his website and follow him on Instagram.

Watch this full YouTube episode on the Let's Go Win podcast.