Unlocking Happiness: 52-Week Bucket List Challenge with Jeremy George [Podcast Ep. 26]

Ever wondered what it feels like to conquer a bucket list challenge?

Join me and Jeremy George, founder of BucketMatch, who completed the “What a Year” project where he attempted to conquer 52 things off of his bucket list in 52 weeks.

In this episode we talk about his experience, why he chose to take on this project, the importance of having a bucket list, and more!

Listen to This Podcast Episode About The Bucket List Challenge

Important Parts in the Show

• 0:13 – About Jeremy
• 1:21 – Why a Bucket List Challenge?
• 3:02 – What Did Jeremy Check Off of His Bucket List?
• 4:23 – What Surprised Jeremy?
• 8:10 – How Has This Changed Your Life?
• 11:25 – Would You Recommend This?
• 14:06 – Final Thoughts

Full Podcast Transcript of The Bucket List Challenge (Episode 26)

*Please note that we do touch on some heavy mental health topics in this podcast.*

Alexandra: Hello adventurers! Welcome to Tick It Before You Kick it – the podcast where we give you inspiration for your adventure bucket list.

I’m Alexandra, your host, and I run a travel blog called The Bucket List Mermaid, and on this week’s episode, we have a very special guest with us.

About Jeremy

Jeremy George is an Entrepreneur, TEDx Speaker, and Creator of the “What A Year” project – an ambitious attempt at crossing off 52 goals from his bucket list in 52 weeks.

From cliff jumping in Hawaii to overcoming stage fright, Jeremy’s year-long adventure was about pushing limits and rediscovering his purpose in life.

Now, as the Founder & CEO of BucketMatch, he’s helping connect like-minded people through their bucket lists and using AI to match them with the right partners and turn their ideas into reality.

BucketMatch accepts new users through a waitlist. Want to join the adventure? Sign up at www.bucketmatch.ai.

So, Jeremy, why don’t you just tell us a little bit about yourself?

Jeremy: Thanks for the intro. I’m really excited to be here and I think you covered a lot of the current state, so I guess I can just share…

I currently live in San Diego with my girlfriend and my dog, Chunky. We just moved here a couple of months ago and I’ve spent the majority of my career in software.

But, as you mentioned, I recently started a company all about bucket lists, and so I’m super excited to be chatting with you, obviously given the topic of your podcast as well.

Why a Bucket LIst Challenge?

Alexandra: Perfect. So what made you start this bucket list challenge?

Jeremy: There’s a very long winded version of it which gets into all these different you know concepts of life and death and what do I really want to do before I die?

And we can certainly get there. But I think the abbreviated version is, you know, I had hit a point in my career, my finances, [and] my lifestyle.

I hit these milestones that I thought were supposed to make me happy and it’s such a cliche story and you hear this so often. But I fell into that trap where, once I had hit those milestones, I realized I was no happier.

It’s not like suddenly my life was so drastically different and that actually sent me into a year-long search where I fell into a deep depression.

I actually struggled with suicidal ideation during that year and that was largely because I didn’t really know what would make me happy.

If all these things were supposed to make me happy didn’t, is it even possible for me to be happy at all?

And then, of course, COVID happened and we were all forced to reconcile with the fragility of life.

And that’s when I realized the reason I was unhappy and the reason I was struggling to determine if life is worth living is because I wasn’t living a life that was true to me.

I had all these things on my bucket list that I wanted to do or at least try to experience, but I was neglecting those things in pursuit these vanity metrics.

Flip the Script

So, let me flip the script.

I’m going to stop doing the things that I think I’m supposed to do and let me just try the things that I think will bring enjoyment, fulfillment and richness to my life, and let’s see what happens.

And then at the end of that year, as you mentioned, I had an opportunity to give a TED talk about the experience and it really transformed the way that I view the world.

What Did Jeremy Check Off of His Bucket List?

Alexandra: Wow, that’s absolutely incredible. I just love that. So, what were some of the highlights or your favorite things that you did check off? Give us some examples of what you did!

Jeremy: Yeah, totally, and I think when people hear the term bucket list, they often think of like just epic, travel and adventure.

I definitely did those things and I also [would] just like to highlight that a bucket list can have a lot of simple and seemingly meaningless goals to other people, but if they matter to you, then that should be on your bucket list too.

So, my list [has] wide variety!

I cliff jumped in Hawaii, as you mentioned. Probably my favorite one was I biked down the coast of California from San Francisco to San Diego. It was a 10 day trip, 650 miles, and that was really rewarding for a lot of reasons.

But you know, I did a lot of simple things too, like I dyed my hair just cause I was curious what that would look like.

Alexandra: What color was it? What color was it?

Jeremy: It was just bleach blonde. Probably something I won’t do again, but you know it was a fun experience for it.

I wrote and I recorded a rap, cause that’s always just something I’ve wanted to do. I paid for a stranger’s meal. So, like I mentioned a whole wide variety of things.

Alexandra: I absolutely love that, and I love how you say that you don’t have to go across the world to do these bucket lists.

They can be small as long as they’re meaningful to you. I absolutely love that.

What Was Surprising?

So, after you finished this challenge, what was one thing that surprised you about checking this off? We talked about, you know, finding happiness and everything. What happened with that?

Jeremy: Yeah, I think the biggest takeaway for me was that it’s really all about the people.

One thing I should mention is, although I set out to try to do 52 things in 52 weeks, which is one year, I only actually was able to cross off 32 out of those 52. So, I still I failed in some ways. Right, that’s like a D minus.

Alexandra: But that’s still a lot. That’s still a lot of things that you did end up checking off, which is super cool.

Jeremy: But I think the lesson was what made the year so transformational for me was the community that I was able to find myself in.

Through just deliberately pursuing these things that I cared about. I reconnected with people that I hadn’t talked to in years.

Shared Bucket List Goals

[And] because we had this sort of shared goal that I didn’t even know they had, and then we were able to go off and try to pursue it together.

Or, I had friends that had already done something that I wanted to do, that were able to help coach me through the process. One of the things you mentioned is I got over my fear of stage fright.

Something on my bucket list was to perform in front of a crowd. And another thing on my bucket list was to learn how to play guitar. Those weren’t necessarily connected.

But fast forward – a friend of mine whose a guitar teacher, he’s a guitar player, he’s in a band right now – he helped me learn how to play the guitar.

And then fast forward a few months later and he had a show coming up. And he said, “Hey, man. I know that one of the things on your bucket list is to perform in front of a crowd. Why don’t you open for me?“

Alexandra: Oh, my gosh!

I had no intention of doing, I was like, “No, I’m not ready.”

I gave all the excuses and he was like, “Look, you’ve got this bucket list. You said you want to do it. What’s what better opportunity?“

And so it was because of him. It was my friend Mitchell. It was because of Mitchell that I ended up doing that.

I mean, I’m pretty sure I blacked out during the performance. I don’t even remember how it went, but you know the sheer reaction of everyone at the end, the applause, they knew the context of what I was trying to do – it was incredibly rewarding.

Bucket Lists are about Connections

But it all goes back to the people, the connections, the opportunity to do something with someone else in your corner. I think that that was the biggest takeaway for me.

Alexandra: Right, and that’s so cool because, as I said, bucket lists are very personalized.

However, I think a lot of people do have similar goals. For example, you’re definitely not the only person who deals with stage fright, I’m sure.

It’s amazing how bucket lists aren’t just about you—they’re also about bringing people together.

Jeremy: Absolutely. And I think what’s really cool is that something that feels so easy, so natural, and so everyday for you might be the number one thing on someone else’s bucket list.

There’s such a huge opportunity for a value exchange between those two people—like, “Hey, I can help you do this thing, and maybe you can help me with something on my list.” 

If we have those conversations more, I think we’d find them incredibly fulfilling.

Conquering Your bucket LIst With Someone

Alexandra: Yeah, and if you check off a bucket list item with someone, it helps your relationship grow so much more.

Jeremy: Absolutely. There’s the tactical stuff—when you tackle a goal together, you can delegate work, save money on things, and so on.

Those are some clear, objective benefits. But beyond that, the whole experience becomes way more fulfilling.

It’s the memories, ultimately, that still stay with me even 4 years after I did this project. The memories, the relationships – that’s what makes it so exciting.

How Has This Changed Your Life?

Alexandra: Exactly. So, big question—how has this changed your life? I know we’ve touched on this, but how has it bettered your life?

Jeremy: Well, the biggest thing is that it solidified what I want to do with my life, which is what led me to start my company.

Not to turn this into an ad for Bucket Match, but for context—Bucket Match connects people based on their bucket list goals. We aim to bring like-minded people together based on what you tell us.

Through my personal experience, I realized how valuable it was to have someone who either shared my goal or had already achieved it and could coach me through the process.

That alone helped me get started, which is often the hardest part.

The truth is, most people have bucket list goals but don’t act on them until it’s too late.

The goal of Bucket Match is to help people take action sooner. People like you already take those steps, but many need accountability partners or just an extra push.

To answer your question and the way that it’s changed me is this journey gave me the experience, unique perspective, and conviction that I needed to dedicate my life to building something that could hopefully bring value to, hopefully, millions around the world.

Working During COVID

Alexandra: I absolutely love that. I used to be an EMT before this, working as a first responder during COVID.

I loved talking to my patients about their lives. In the back of the ambulance, I’d ask, “What’s the favorite thing you’ve done?” and so many people said what you’ve just shared.

I forget the term you just used – was it “vanity experiences”?

People often focus on the wrong things—things that don’t truly make them happy or fulfilled—and by the time they realize it, it’s too late. That really resonates with me. What you’re doing, connecting people, is so meaningful.

As someone who lives in an RV, I don’t always have people around to share these bucket list experiences with.

It’s so important—whether it’s making new friends or achieving bucket list goals with loved ones, either or.

Jeremy: Exactly! With all these tools and platforms allowing us to connect—like you and I are doing now across different states—it’s amazing what’s possible.

One Common Bucket List Goal

One of the most common goals I see in Bucket Match is learning a new language.

With today’s technology, you can connect with someone from Spain, China, or Thailand and learn directly from them, even if you guys aren’t directly together.

That’s exactly what I’m hoping to achieve—connecting people through their shared goals.

Alexandra: The best way to learn a language is to get a buddy.

Jeremy: Exactly! And hopefully, someone who knows it well enough to introduce you to not just the language, but the culture too.

Would You Recommend This to Others?

Alexandra: Exactly. So, would you recommend your bucket list challenge—like completing 32 out of 52 goals—to others?

Jeremy: That’s a great question, and I get asked that a lot.

There are people who thinks it sounds really cool but it’s not for [them]. And I think that is totally fiar.

I think it’s important to acknowledge that it’s not for everyone; I was in a unique place in my life where I needed something drastic to shake me out of a dark path.

I wouldn’t recommend this for everybody.

What Jeremy Recommends

For people in a similar situation, absolutely, go for it! But I’d recommend taking a moment to confront mortality or the concept of endings.

If you are in high school, confront the fact that you will no longer be in high school. Or if you are in college, confront the fact that you will graduate someday.

Whether it’s high school, college, turning 30, or having kids—when we are sitting in these moments and look back on it, we have so much clarity.

“I wish I had done that” or “I should’ve taken that risk.”

When people are at the end of their lives on their deathbed, studies show that 76% of people regret the things they didn’t do more than the things they did. My advice is to confront those moments now.

Think about what you’ll wish you had done, write it down, recruit a friend to help, and take the first step.

Facing Our mortality

Alexandra: I totally agree. People often distract themselves from thinking about those thoughts—like, “I’m not invincible, I’ll get wrinkles someday”—we tend to push [those thoughts] down.

If we have that attitude, life tends to pass us by.

A bucket list isn’t just about checking items off; it’s about embracing life’s fragility and making the most of the time we have.

Jeremy: Absolutely. It might feel uncomfortable or morbid to confront mortality, but when you talk to people at the end of their lives, it’s often a moment of clarity, not fear.

Life becomes easier and more focused when you embrace that mindset. You aren’t as distracted and you know what you want to do.

Alexandra: Yeah, I totally agree. Is there anything else you’d like to share about your experiences or the importance of having a bucket list?

Reach Out If you Need Help

Jeremy: Two things. First, on a somber tone—if anyone listening is struggling with depression, suicidal thoughts, or anything in that realm, I hope that you take the initiative to speak with someone.

Whether it’s a hotline, therapist, or doctor, don’t hesitate to reach out.

Lastly, if you want to reach out to me personally, I am happy to be that person to hear you out because I know what that’s like.

Celebrate Failure

Second, on a lighter note, one that that prevents a lot of people from taking that first step is fear of failure, fear of rejection, or fear of not knowing exactly what to do or not having a perfect plan in place.

That fear is natural. Something that has helped me and something I advise our users on is to celebrate failure and rejection as steps toward success.

They are a necessary precursor to success. Especially with your most ambitious goals.

For example, when I tried to get on a TEDx Talk, I reached out to 11 different venues and I only heard back from one. It was, like, a 10% success rate.

Nothing that comes easy will be worth it, but if you celebrate being rejected, you create neuropathways in your brain. You become a little bit addicted to just trying – not whether you succeed or fail.

Alexandra: I love that because every failure is a lesson. True failure only happens when you stop trying altogether.

Jeremy: Exactly!

Thank You For listening!

Alexandra: Well, thank you so much for coming on the show! That’s a wrap for this episode of Tick It Before You Kick It.

For more bucket list inspiration, visit thebucketlistmermaid.com, or check out Bucket Match to connect with Jeremy.

Don’t forget to subscribe to the podcast or find me on social media at @ thebucketlistmermaid.

Keep adventuring, and go check off that bucket list!

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