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December 12, 2024 • 16 mins

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What if crossing items off your bucket list could transform your life? 

Join us as we unlock this idea with Jeremy George, an entrepreneur and TED Talk speaker who set out to conquer 52 bucket list goals in just 52 weeks. 

Jeremy's incredible journey took him from feeling unfulfilled despite achieving conventional milestones to finding true happiness through exhilarating adventures and meaningful connections. 

In our conversation, we confront the fear of failure and rejection, exploring how facing these challenges can lead to personal growth and resilience. 

Embracing the fleeting nature of life, Jeremy encourages us to gain clarity on our deepest desires and take meaningful actions. 

We also discuss the vital importance of mental health and seeking help when needed. 

By sharing lessons learned from embracing rejection and celebrating persistence, this episode offers a roadmap to living a life true to oneself and invites listeners to connect by sharing their own bucket list adventures.

Let's Go Adventuring:
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Get in Touch:
alexandra@thebucketlistmermaid.com

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Alexandra (00:00):
Hello adventurers, Welcome to Take it Before you
Kick it the podcast where wegive you inspiration for your
adventure.
Bucket list.
I'm Alexandra, your host, and Irun a travel blog called the
Bucket List Mermaid, and on thisweek's episode, we have a very
special guest with us.
This is Jeremy George.
He's an entrepreneur, a TEDTalk speaker and creator of a
what A Year project theambitious attempt at crossing
off 52 goals from his bucketlist in 52 weeks.

(00:22):
From cliff jumping in Hawaii toovercoming stage fright,
Jeremy's year-long adventure wasabout pushing the limits and
rediscovering his purpose inlife.
So now, as the founder and CEOof Bucket Match, he's helping
connect like-minded peoplethrough their bucket list and
using AI to match them with theright partners and turn their
ideas into reality.
The Bucket Match now acceptsnew users through a wait list,

(00:43):
so if you want to join theadventure, you can sign up at
bucketmatchai.
So, Jeremy, why don't you justtell us a little bit about
yourself?

Jeremy (00:49):
Sure Well, yeah, thanks for the intro.
I'm really excited to be hereand I think you covered a lot of
like the current state, so Iguess I can just share.
I currently live in San Diegowith my girlfriend and my dog,
chunky.
We just moved here a couple ofmonths ago and I've spent the

(01:14):
majority of my career insoftware.
But, as you mentioned, Irecently started a company all
about bucket lists, and so I'msuper excited to be chatting
with you, obviously given thetopic of your podcast as well.

Alexandra (01:21):
Yeah, perfect.
So what made you start thisbucket list challenge?

Jeremy (01:30):
So you know, there's like a very long winded version
of it which gets into sort oflike all these different you
know concepts of like life anddeath and what do I really want
to do before I die.
And we can certainly get there.
But I think the abbreviatedversion is you know, I had hit a
point in my career and myfinances, my lifestyle.
I hit these milestones that Ithought were supposed to make me
happy and it's such a clichestory and you hear this so often

(01:51):
.
But I fell into that trap where, once I had hit those
milestones, I realized I was nohappier.
It's not like suddenly my lifewas so drastically different and
that actually sent me into ayear-long search where I fell
into a deep depression.
I actually struggled withsuicidal ideation during that
year and that was largelybecause I didn't really know

(02:12):
what would make me happy.
If all these things weresupposed to make me happy didn't
, is it even possible for me tobe happy at all.
And then, of course, covidhappened and we were all sort of
forced to reconcile with thefragility of life.
And we were all sort of forcedto reconcile with the fragility
of life, and that's when Irealized, you know the reason I
was unhappy and the reason I wasstruggling to really determine
if life is worth living isbecause I wasn't living a life

(02:32):
that was true to me.
No-transcript.
I'm going to stop doing thethings that I think I'm supposed
to do and let me just try thethings that I think will bring,
you know, enjoyment, fulfillmentand richness to my life, and

(02:54):
let's see what happens.
And then at the end of thatyear, as you mentioned, I had an
opportunity to give a TED talkabout the experience and it
really transformed the way thatI view the world.

Alexandra (03:02):
Wow, that's absolutely incredible.
I just love that.
So what were some of thehighlights or your favorite
things that you did check offLike?
Give us some examples of whatyou did.

Jeremy (03:11):
Yeah, totally, and I think you know when people hear
the term bucket list, they oftenthink of like just epic, travel
and adventure.
I definitely did those thingsand I also just like to
highlight that a bucket list canhave a lot of simple and, you
know, seemingly meaninglessgoals to other people, but if

(03:32):
they matter to you, then thatshould be on your bucket list
too, and so my list wide variety, right?
Um, I, I, you know, I I cliffjumped in Hawaii, as you
mentioned.
I my probably my favorite onewas I biked down the coast of
California from San Francisco toSan Diego.
It was a 10 day trip, 650 miles, and that was really rewarding
for for a lot of reasons.
But you know, I did a lot ofsimple things too, like I dyed
my hair just cause I was curiouswhat that would look like.

(03:52):
What color was it?
What color was it?
It was just bleach blonde.
I love that and probablysomething I won't do again, but
you know it was a fun experiencefor it.
I wrote and I recorded a rap,cause I was that's always just
something I've wanted to do.
I paid for a stranger's meal.
So, like I mentioned a wholewide variety of things.

Alexandra (04:13):
I absolutely love that, and I love how you say
that you don't have to go acrossthe world to do these bucket
lists.
They can be small as long asthey're meaningful to you.
I absolutely love that.
So, after you finished thischallenge, what was one thing
that surprised you about justchecking this off?
We talked about, you know,finding happiness and everything

(04:34):
what.
What happened with that?

Jeremy (04:36):
Yeah, I think the biggest takeaway for me was that
it's really all about thepeople I think and when I.
When I say that, you know Iguess I.
One thing I should mention is,although I set out to try to do
52 things in 52 weeks, which isone year, I only actually was
able to cross off 32 out ofthose 52.
So I still I failed in someways.

(04:58):
Right, that's like a D minus.

Alexandra (05:00):
But that's still a lot.
That's still a lot of thingsthat you did end up checking off
, which is super cool.

Jeremy (05:06):
I and and and fantastic experience.
But I think you know the lessonwas like what made the year so
transformational for me was thecommunity that I was able to
find myself in.
Um, through just deliberatelypursuing these things that I
cared about, right I, Ireconnected with people that I
hadn't talked to in yearsbecause we had this sort of
shared goal that I didn't evenknow you know they had, and then

(05:28):
we were able to, like, go offand try to pursue it together,
or I had friends that hadalready done something that I
wanted to do, that were able tohelp coach me through the
process.
You know, one of the things youmentioned is I got over my fear
of stage fright.
Something on my bucket list wasto perform in front of a crowd,
and another thing on my bucketlist was to learn how to play
guitar.
Those weren't necessarilyconnected, but if I fast forward

(05:51):
, a friend of mine who's aguitar teacher, he's a guitar
player, he's in a band, right,he helped me learn how to play
guitar.
And then fast forward, a fewmonths later he had a show
coming up and he said hey, man,I know, one of the things on
your bucket list is to performin front of a crowd.
Why don't you open for me and Iwas like, and I had?
you know I had no intention ofdoing.
I was like no, I'm not ready.

(06:11):
You know I gave all the excusesand he was like look, you've
got this 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 thatI ended up doing that Right,
and then, having performed, Imean I'm pretty sure I blacked
out during the performance.
I don't even remember how itwent, but you know the sheer

(06:31):
reaction of everyone at the end,the applause they knew the
context of what I was trying todo was incredibly rewarding.
But it all goes back to thepeople, the connections, the
opportunity to do something withsomeone else in your corner.
I think that that was thebiggest takeaway for me.

Alexandra (06:45):
Right, and that's so cool because Cause, as I said,
bucket lists are verypersonalized.
However, I think that a lot ofpeople do have very similar
cause, like you are not the onlyperson who deals with a fear of
stage fright, I'm sure.
So I think it's really coolthat bucket lists are not only
for you, but they're also forbringing people together.

Jeremy (07:04):
Absolutely.
And I think what's really coolis that what you'll find is
something that for you is likeso easy, so natural, so
day-to-day, for someone elsemight be like the number one
thing on their bucket list,right, that they want to move
over.
And there's a huge opportunityfor a value exchange between
those two people to say, hey, Ican help you do this thing and,
you know, maybe you can help medo something else on my bucket

(07:24):
list.
And I think if we just if weconfront those conversations
more, I think we'll find it tobe really fulfilling.

Alexandra (07:30):
Yeah, and I think if you check it off together, if
you check it off with somebody,I think that that helps your
relationship grow so much more.

Jeremy (07:38):
Absolutely.
I mean, there's the tacticalstuff which is literally just,
if you do it together, you candelegate work, right, you can
maybe save money on things Likethere are some like very just
like objective, clear reasons,but what I found in addition to
that is it makes the entireexperience way more fulfilling.
Right, it's the memories,ultimately, that still stay with
me, even, you know, four yearsafter I did this project.

(07:59):
The memories, the relationships, that's, that's what makes it
so exciting.

Alexandra (08:03):
Exactly so big question how has this changed
your life?
I know we've kind of alreadygotten into it, but how's it
bettered your life?

Jeremy (08:12):
Well, the big thing for me is, I think it helped
solidify what I want to do withmy life, which is the company
that I started.
Now.
So and you know, not at allintended to be an ad for Bucket
Match, but just the context is,what Bucket Match does is we
help connect people based ontheir bucket list goals and, as
you mentioned, we try to findlike-minded people based on what
you tell us.
Through my own personalexperience, I know that one of

(08:34):
the most helpful things was if Ijust had found someone else who
either wanted to do the samething as me or had already done
that thing and could help coachme through the process.
That was, in and of itself,valuable to help me actually get
started on that goal, becausethe biggest problem is the
majority of people.
We have things that we want todo before we die.
We know what they are, but wedon't take action on them until
it's too late, and so the goalof Bucket Match is to help

(08:57):
people take action sooner.
Obviously, someone like you Ithink you probably fall into
that category of people who aretaking those steps, but
sometimes other folks needaccountability partners.
They need just that extra push.
It has given me really theexperience, the unique
perspective and the convictionthat I needed to say, hey, this

(09:20):
is something that I'm preparedto dedicate my life towards, to
try to build this company andreally bring that value to,
hopefully, millions of peopleacross the world.

Alexandra (09:28):
I absolutely love that.
Yeah, I actually was an EMTbefore this, so I worked as a
first responder during COVID andI obviously love travel, so I
would talk to my patients a lotabout you know, when we were in
the back of the ambulance I'd belike, hey, what's your favorite
thing that you've done?
And so many people said exactlywhat you said.
And, um, I forget, I forgetexactly the term that you use,

(09:48):
just like vanity experiences.
I think a lot of people tend tofocus on the wrong thing and it
doesn't make them happy.
It doesn't make them happy, itdoesn't make them fulfilled, and
by the time they realize it,it's too late.
So I really resonate with thatand I think it's really amazing
what you're doing withconnecting people, Because, also

(10:09):
, I live in an RV, as you cansee, so I don't have a true home
base, so sometimes I don't havea lot of people to do these
bucket list things with.

Jeremy (10:20):
So I think that that is really, really important to
maybe make new friends orconquer some bucket lists with
your loved ones either, orTotally, totally, and I think
that, especially with theproliferation of all of these
different systems that allow usto communicate even like you and
I were in totally differentstates, but we're able to have
this conversation and thisconnection over Zoom, we're
seeing more and more of thatbeing democratized across
everybody, right?
So, if you know, one of themost common bucket list goals I

(10:42):
see in Bucket Match today is Iwant to learn how to speak a new
language.
Right, a lot of people want tolearn a new language.
Well, you can actually connectwith someone in Spain or in
China or, you know, in Thailand,wherever it is, and you can
actually have that opportunityto learn from that person, even
if you guys aren't directlytogether.
And that's, you know.

(11:02):
That's another way that I'mhoping to just connect people in
the world based on what theirsimilar, you know, shared
desires are yeah, that's.

Alexandra (11:05):
The best way to learn a language is just to get a
buddy.

Jeremy (11:09):
Exactly and hopefully, someone that you know, knows it
really well and can introduceyou to more than just the
language, but the culture andeverything else.

Alexandra (11:16):
Exactly yeah, so would you recommend you know, I
know that you did what was it 39out of 52, 32, 32 out of 52.
Would you recommend thisexperience of, you know, really
hitting your bucket list hard?
What would you recommend toothers who are looking to take
this journey?

Jeremy (11:33):
Yeah, that's a great question.
I get asked that a lot becauseI think there are people that
say, hey, that sounds reallycool, but I don't know if it's
for me, and I think that'stotally fair right.
I think I was in a very uniqueposition in my life where I
needed something to really joltme out of the path that I was on
, because it was a pretty darkpath at that time.
I wouldn't recommend this foreverybody.

(11:54):
If you have that desire,absolutely you should go for it.
What I do recommend is taking amoment to sort of confront
mortality or confront the end,whatever it is right.
If you're in high school, youknow, confront the fact that you
will no longer be a high schoolstudent someday.
Or, if you're in college,confront the fact that you will
graduate someday and you havethis sort of unique experience.

(12:14):
And you know, if you're aboutto turn 30, right, confront
whatever it is.
You're about to have a kid.
There are all these milestonesin our lives that when we're
sitting in those moments and welook back on it, we have so much
clarity right, oh, I wish I haddone that, or I should have
taken this risk or what it is.
As you mentioned, you know,people at the end of their lives
, on their deathbed or in thesestark positions.

(12:35):
There have been studies shownthat 76% of us will regret the
things that we didn't do morethan the things we did, and so I
think, really, therecommendation that I have is
try to confront that moment,think back on.
What is it that you're going towish you had done?
And then the good news is youactually have the time to do
that thing, and so that would bemy recommendation is write it
down, try to recruit a friend tohelp you do it and take the

(12:57):
first step.

Alexandra (12:58):
Yeah, I totally agree , because I think that we tend
to distract ourselves from thatthought.
You know like, oh, I'm notinvincible, I'm going to get
wrinkles someday.
You know like we tend to justpush that down, and I think it,
if we have that attitude, lifetends to pass us by.
If we have that attitude, lifetends to pass us by.

(13:21):
And yeah, and I think that withbucket lists, it's so much more
than just, oh, I want to, youknow, go to Spain or I want to,
you know, have a snowball fightLike it.
It really forces us to livewith that mortality and make the
most of the time that we havehere.

Jeremy (13:31):
Yeah, absolutely, and I get it because it can be
uncomfortable to sort of andfeel maybe morbid, to like
really confront mortality.
But I think if you talk to mostpeople and you've, you know, as
an EMT, had this opportunitybut when you speak with people
who are actually in that moment,it's not as scary as as we
perceive, right, it's typicallya moment of clarity, right.
It's like wow, you know, lifeis fragile and so I think, if

(13:54):
you, if you just allow yourselfto immerse, immerse yourself
into that, that attitude, you'llfind that life becomes a lot
easier because you're not asdistracted and and you know what
you want to do.

Alexandra (14:03):
Yeah, yeah, I totally agree.
So is there anything else thatyou want to share about your
experiences, why having a bucketlist is important, anything
along those lines?

Jeremy (14:14):
I think, two things that I typically like to say.
The first is, on a more sombertone.
If anyone who's listening tothis is going through anything
on the spectrum of suicidalideation, depression, anything
that they're struggling with, Ihope that you'll take the
initiative to speak with someone.
I think that's the mostvaluable thing.
That's the most important thingis just to share it.

(14:36):
There are hotlines, right Ifyou want to talk anonymously.
Talk to a doctor, therapist, orif you're able to open up to
your friends.
Lastly, if you want to reachout to me personally, I am also
happy to be that person, to hearyou out, because I know what
it's like.
And then, on a maybe more funnote, I think I would say that

(14:56):
one thing that prevents a lot ofpeople from actually taking
that first step is a fear offailure, a fear of rejection, a
fear of not knowing exactly whatto do, of not having the
perfect plan in place.
I think that's a really naturalreaction.
A lot of our users on is toactually celebrate failure,
celebrate rejection andrecognize that failing, getting

(15:18):
rejected or whatever it is allof those are just one step
closer to eventual success andthey are a necessary precursor,
honestly, to success, especiallywith your most ambitious goals.
And so if you celebrate gettingrejected as an example, when I
tried to get on the TEDx talk, Iactually reached out to 11
different venues and I onlyheard back from one right.

(15:40):
So I was like a 10% successrate, but the one that responded
was like hey, we'd love to haveyou, and so nothing ever will
come easy if it's worth it.
But I think if you celebrategetting rejected, you create the
neural pathways in your brainto become a little bit addicted
to just trying, not whether yousucceed or fail.
So that would be my last sortof tidbit there.

Alexandra (16:01):
Well, yeah, and I love that, because I feel like
every time you fail you learnsomething, and only true failure
comes when you stop tryingaltogether.

Jeremy (16:08):
Absolutely, I would agree.

Alexandra (16:10):
I absolutely love that.
Well, thank you so much forcoming on this show.
That is a wrap for this episodeof Take it Before you Kick it.
As always, if you want to headover to thebucketlistmermaidcom
for more bucket list inspirationor you want to head over to
bucketmatchai and spend sometime with Jeremy over here, you
can subscribe to this podcast orreach out on social media at

(16:31):
thebucketlistmermaid.
Thank you, guys, so much forwatching.
Keep adventuring and check outthat bucket list.
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