#351 - Jillian Jacqueline on Recording A Song on Her Debut Album While Holding Her Newborn + What She Learned from Her Parents Getting Divorced When She Was 13 + Debating Albums vs. Singles with Bobby - Bobbycast

Episode Transcript
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Speaker 1 (00:01):
I welcome to episode three fifty one with one of
my favorite artists, Jillian Jacqueline, meaning my favorite, like I
listened to her music when I just get to pick
my own music to listen to, meaning if it's me time,
I listened to Jillian. For example, when I'm talking about
Jillian song, because this is an older one, it's called
Reasons We've Got all. This is older stuff from Jillian.

(00:27):
I should say this too, that I took Jillian on
towards me for a long time and years ago, but
I was such a big fan. She came out and
opened a bunch of my comedy shows. And they weren't
married at the time. I think they were just dating.
But her husband now was her guitar player. And she's awesome.
She's awesome, he's awesome, And they came to my wedding.
Like That's how much I really enjoyed and really respect Jillian.

(00:50):
So her debut album, Honestly is out now. Just a
couple of things we've talked about and featured on the show.
Bandwagon is the current single, and we've played it on
the Women of By Our Country, the big weekend show
Here You Go Go Away. This little song those fifteen minutes.

(01:13):
So that is her new single on the new record.
And here is Better with the Broken Heart with t
j Osborne. They've came in and played on the show before.
Jillian and Brian just had a kid, a little son
named Rockwell. Pretty awesome. This is her debut album, and

(01:34):
I'll talk about in a minute how it crazy to
me that it's her debut album because I've just been
listening to her music for such a long time. But
when you get pretty deep here, I mean it's cool
to have a friend in because you can kind of
go a lot of places without having to feel it out.
That makes sense. Definitely a different dynamic. Yeah, Like if
it's somebody that I really that I know, no, I
don't have to weigh in and be like, I don't know,

(01:54):
do they like that? If I don't back out, just
go right into it. And she's such an interesting person
and artist and maybe this is your introduction to her.
So Jillian Jacqueline, enjoy this and go support her music.
Streamer music if you like it. Thank you guys. It
is a Bobby cast and here we go. I walked
into a conversation about the beach, which I hate. The
beach so I don't know what the conversation was about

(02:17):
the beach. I don't hate the beach. I don't don't
like being at the beach. I guess it's a difference
because I don't hate that the beach exists. I don't
care like I don't see the beach and a picture
and go get your beach. I hope you burned down beach.
You don't enjoy being on the beach. I don't see
the point, but not love the ocean. No, Oh, I
understand that. I understand the point of the ocean, but

(02:39):
I don't understand the point for me. I don't understand
the point of being on a beach. I don't like
anything about it. I understand why my wife likes it.
She likes to go in land a beach and just
relax and let water here the water and Jim get
in the water. Sometimes like why does it? Why don't
have to be near water if you're not gonna get
in it. It's like going for a boat ride and
not jumping in the water. Yeah, I have to go
in it. Yeah. So the beaches, I'm hot, sand everywhere.

(03:04):
I don't drink, and I think if I drank a
little bit. That probably help. It helps, but you have
to make sure you have a cooler with ice so
that the drinks are cold. But I don't. But I
don't drink. If I were able to drink, I think
I would enjoy everything more drink. That's probably true. Yeah,
Like I said, you have to come prepared. Convince me
in thirty seconds why I should like the beach. Oh

(03:24):
my god, there's nothing more to me. There's nothing more
cleansing and joyful than swimming in the ocean. I literally
feel like my happiest version of myself when I'm swimming
in the ocean. Where'd you grow up in Pennsylvania? So
you had the ocean near you could drive to it
in three hours? Right? Okay? I sent a lot of

(03:45):
times the ocean might Cape Cod and Nantucket and stuff. Yeah,
that's my point. Yes, I grew up doing that. I
never saw the ocean toss and now I happen to
drive by it. I'm from Arkansas. We're extremely landlocked, and
I didn't get to the state much, and so once
I thought it was pretty cool. When I saw I
was like, Wow, it's so big. And then the first
time I got in it, I was like twenty four,

(04:06):
so and I was like, let tastes like crap. So
not only does it taste bad, and listen, I'm not
a drink in the ocean. Water is taking big golds
of the salty. My only point is I think your
association with the feeling of the beach is that feeling
of being a kid. Yeah, okay, sure, yeah, I'm also

(04:28):
Pisces and I just love the water. So you see,
I also believe, and pardon this, that astrology is complete gibberish.
That yeah, right and right, and my husband thinks that.
And I like it for why it exists. I think
it can be fun. I think it can lead to

(04:49):
self discovery and ways of going. Oh you know why
I agree with I am like this or I'm not.
But as far as like basing it on anything scientific whatsoever,
there is none. I know, you should talk to my
three sisters because they're all like so hardcore astrology and
I'm actually the one that's more like you. But there
are certain things where like all my Pisces friends we
do have we do have these similarities. I like it

(05:09):
because I think if it makes you a better person
or a happier person, or gives you an interest. That's great.
So I for so astrology, for what I feel it
is great. Yeah, for people who feel like it's a science,
it's absolutely But you know, I'm like, I don't know
that that's because that wouldn't make sense. Everybody born on
my birthday is not like me and a little bit.

(05:31):
It's like when John Edwards the psychic would be like,
all right, yeah, I'm talking to somebody from your past.
There's a I don't know, there's like an aunt with
a vowel. I was like, well, this is crazy. I
feel like a little bit it could be that, but
you're allowed to associate your own feelings and emotions with
whatever is said. All that to say that I think
the beach for a lot of folks is some sort

(05:55):
of a flashback to a a better, easier, less stressful
childhood time. Same thing with music, I guess. And that's
the point I was gonna get to here. Yes, um,
but so I hate the beach. We'll end on that.
I'm not a beach guy. I'm going We're going to
the beach and I'll go and sit, but I I

(06:16):
end up laying there with I'll put music on her podcast.
My phone is up overheating and that sucks, or my
headphones get hot and have sand and I can't swim
in it because I don't have someone in the pool.
I'll be honest with you. Why just sit in the
body of water for the sake of being in the
botto water? Body water? A normal got to agree to
disagree on this one. I don't even no, no, no,

(06:37):
I'm an idiot, and I'm not even arguing absolutely, I'm
not arguing that I'm right. I just don't like a pool. Okay,
that's my wife will lay outside of a pool if
you will read a book, And I'm like, you could
read the same book in the air condition in the
house with instead of out in the because you wouldn't
just go stand in the heat for and walk around

(06:58):
and read the book. But why being in proct Do
not enjoy the feeling of feeling like weightless, like when
you're floating? Yeah with the great WiFi? Yeah? Um, you know, no, okay,
I really like that feeling. You know. My association with
water is boats and fishing and lakes and swimming was

(07:19):
pretty fun. But but but I like to do I
like to have activities. I see, I don't like that
I don't like boats. I don't like, um, all those
like parties that people do, like on yachts. I hate that.
I've never done it. But you're not in the water.
I'm jealous of all the rich people, so I hate it. Yes,
well you can do it now. Yeah, but I, um,
maybe you should get a vote. Do you have a boat? Okay,

(07:41):
we've talked about getting a boat. My wife's like, we
should get a boat, but she's so balanced and normal,
and I'm like, why do we need a boat? Yeah?
We can so all of that to say, we have
these thoughts about our our childhoods that allow us to
enjoy things still today, and you know, even musically. You know,
I was I was listening to like a clash sick
rock station yesterday, m excuse me. And classic rock now

(08:05):
is weird because some of the songs that I grew
up on are now played on classic rock, which is
stupid and they should never allow that. They shouldn't play
Radiohead and Nirvana on classic row. That's actually crazy. Oh.
I thought you were gonna say like Journey, but now
I grew up on Journy Jelly. I didn't think you
were that old, but hey, I listened to journey in
high school, so did I. But yeah, again, I wouldn't
be upset a class work for my journey. That sure, okay,
But you mean like Radiohead and Nirvana, that's crazy. That's

(08:27):
not classic rock now. But I'm listening eye blind classic yes,
if it's not, because it's defined by a year and
agoin that makes me feel very old. And I'm listening
and yesterday, we're driving to dinner, and this is all
You're gonna see some full circle and then be blown
away at how I just point you and I am
in an amazing interviewer. And so we're driving to dinner.
What is on? Hey Man, Nice Shot? So hey Man,

(08:50):
Nice Shot is on from like late nineties. Caitl's like
this is oh, I like this pretty aggressive and she
goes in for you, that's pretty aggressive because I don't
listen to anything rest of now. I like singer songwriter stuff.
I like. I like McKinney, Chesney slow, I like, I
like a vibe. What you like for the beach. I
guess I like my slow music, right, And I was like,
you know, I guess because I liked it when I

(09:12):
was a kid. Like I'm still into this. I'm still into.
And then a song followed it on a rock station
that was a new song, but it sounded very similar,
and I was like, you know, I don't actually mind
this either. So here I am still enjoying something that
I liked as a kid. So I don't really think
I enjoy anymore. But because I have this association with
I'm like, I just kind of feel comfortable in it. Yeah,
you can like compartmentalize and go back to that version

(09:34):
of yourself. I didn't know I really could until yesterday,
when this is happening. Yeah. That that's really strange and
makes a lot of sense. I feel that way too.
I think if I listened to all American Rejects right now,
I wouldn't hate it. And I should technically because I
don't listen to that kind of music anymore. But that
was the first like pop rock band that I got into,
and it's just nostalgic. It's like something in your body
is like responding emotionally. There's a book that I've referenced

(09:56):
a few times that I read many years ago called
I'm Okay, You're Ay, and it's basically a book about uh,
the psyche and feelings and emotions and um the most
scientific book on emotions that I've ever found, which tough
because it's it's emotion. It's not really data driven. We'll
feel for different reasons. And they talk about certain songs

(10:16):
when you hear them that if you've heard it so
many times for us, you know, brief, it's not even
a second, for a brief uh micro period of time
in your brain, your brain releases the same exact chemical
that it released when you heard and enjoyed it when
you were a child. So and it can be music,
or it can be a smell, but I think I

(10:37):
think it was something that I've never heard of before
that it's probably related to that, right, But but it
was these smells are these sounds that we hear for
and that's why it feels. And you just said nostalgia.
That's what a lot of nostalgia is where you're like, oh,
I feel this again, but it's really because you are.
You're for a split second, you're reliving that that that
feeling and that emotion. Yeah, you know, it's weird. Having

(10:59):
a baby um feels sometimes like constant deja vu because
I'm experiencing joy through what he's experiencing and I'm like, whoa,
why do I feel like I've done this before? Oh?
Because I was him once and I felt so excited
about bathtime, you know what I mean. So you that's interesting.
I've never heard it a position like you actually think
you can remember those feelings of being a young I

(11:20):
won't say baby, but a young young kid. Yes, yeah,
oh yeah. Like when we're outside and he's looking up
at the trees and I get this rush of like
in my body it's like joy, it's like fulfillment, and
I'm like, oh my god, I'm feeling what he's feeling
like it's the first time. That's interesting. It's amazing that
you can because I'm sure our brains have all that store,

(11:41):
we just can't access it. I'm sure what they have
they have a month in store. Do you remember your
first memory as a human, Well, I think it'd be
I think you have to remember your first memory just
by that sentence. Okay, do you remember your first moment
in life? Like? Yeah, can you? Here's what I remember?
I remember cares this bear with me. It's pretty dark.

(12:04):
Where I was was pretty dark, and then all of
a sudden, it was like somebody had opened a door
or something, and then I remember moving and then all
of a sudden I looked up and then the doctor's
head was there and I was coming out of a vagina. No,
I don't. My first memory is that, like five four
or five years old, I really got me there. I

(12:24):
was like, where is he going to go? I have?
You know, you know there's people that claim they do
remember that. I have idiot friends who think that. Do
you really think that's impossible? Though I know I don't
think it's impossible. I have no way to know if
they actually do. We have no idea. It could be possible.
Someone just told me that there was a baby born
with all of its teeth. Anything, it's possible. I see
fish born with teeth sometimes. But I agree in that

(12:46):
if I can't prove it's impossible, that I can't believe
it's impossible. Correct. So, but my friends are idiots who
say this, and so based on their other actions, I
don't believe it. Yeah, you're like, your track record does
not lend itself to you make any sense? Have you
stuck your kid in the ocean yet? Yeah? I gotta
tell you it was such a lesson in expectations. Like

(13:07):
I said, I love the water. I love the ocean.
And when we put Rockwell's feet down in the sand
right at the as the tide was coming in, he
started screaming and wanted to be picked up, and there
was like this part of me as a mom. I
was like, no, you like it, you like it. You're
you're supposed to like the ocean. And Brian was like, no,
he's really not into it, and my heart kind of sank.
I was like, oh, no, my kid doesn't like the ocean. Well,

(13:29):
he gets to be kind of like your husband too,
you know, yes, I think the Brian was coming through,
but it was such a lesson for me, and like,
this has nothing to do with you. This is his experience,
his life. Let him be his own person and he
probably will grow to love the ocean, and if he doesn't,
that's okay too. But I was like kind of disappointed
because I wanted his first moment to be like this sweet,
blissful like guys flashing in the waves. No, that was

(13:51):
not it at all, which leads me to track one
The Ocean featuring featuring Charlie Wassham. Here you go soon

(14:11):
more of a metaphor type thing, but still, you know
you get it. Charlie's wonderful, So wonderful is wonderful? Um,
and so you wrote this with tofor and Hillary Lindsay,
which is pretty strong room right there. Yeah. Track ones
are always interesting to me on why they and again,
albums are becoming I'm gonna separate albums from bodies of

(14:33):
work two different things in my mind. Don't don't don't
hate me when I say bodies of work can be
three songs, seven songs, that it can be an album.
Albums are losing importance two bodies of work based on
consumption and um, the A D D of our culture. Okay,
so this question I probably won't even ask it in
two years because of how music is kind of moving along.

(14:56):
But track one, like, why what what about this song?
Was it? The tempo of the song, the message of
the song? Because track wants a big decision because it's
up there first? Why the ocean? First of all? It
makes me so sad that you're not going to be
asking this question in two years. Because I think albums
are going to survive. I don't. Here's what I think. Yes,
in a way, I think concept albums will survive. Yeah,
I don't think thirteen songs. Is a body of work

(15:18):
matters because what's happening is and I speak from this
is someone who loves music. You love music. I don't
have time to listen to thirteen songs enough times, no,
if I really like them or not. So songs get
lost in the mix because there's something else great, then
well that's your okay, So that's your opinion on why.
But there's also there's still something that we said for
the creation of albums. I think they're still important, even

(15:40):
if you have to piece meal in and say, okay,
I'll listen to these six songs. That's great. Yeah, that's
not what we're talking about. So we're talking about an album.
I don't need to argue against it. I mean you should.
I like it. You're right if you put out thirteen
songs at once and just presented as an album and go,
this is my new album. I believe there are probably
and I'll do your you have eleven on yours. Um.

(16:01):
I believe that people if they're just discovering you. I
don't think let's say, um song that it's been out
for all magic Yeah, okay, maybe if they never heard it.
Maybe because Magic is such a lovely lovely song. If
they don't listen to it twice, they don't really understand
how great of a song that is because they didn't
have enough time because there was so much to get through. Yeah,
well that's just a whole bigger conversation. That's collective culture. Yeah,

(16:26):
so I'll track one track one the ocean. Um well,
this was, um the only song on the record that
actually the concept came to me like in a not
a dream. But I was like half asleep and I
was like, oh my god, I have to write this song.
So we wrote this song. I brought it into Hillary
because I always try to come in with something really
solid with her because you know, she writes really fast

(16:49):
and you can it's just she's very powerful. So we
came in, we wrote it for you know, it took
up like an hour, and um, you wrote song a really,
I would think, so that's super quick because the chorus
fell out and then the verses were very autobiographical, and
you know, she's very confident and she'll just say, yeah,
that's it, that sounds great, like let's move forward. And
so I was very trusting of kind of her instincts

(17:10):
and and tof you know, it's just so great too.
So anyway, when it came to the track list, I
was just thinking of every song intro and then outro
into the next song. And I like records that start
with a really powerful moment, and I love the intro
to the ocean, and it feels like this wave kind
of leading in. And also there's this overarching um sort

(17:33):
of optimism um and and sort of a bridge to
me between like where I was. You know, I'm talking
about my past and then I'm also talking about finding
my future and that really sums up a lot of
what honestly represents. So it just felt felt right message
based song, you like the message the field of as

(17:54):
opposed to just like the like tempo. I wasn't thinking
about that at all when I didn't think you did.
I don't know that that's ever, you know, with with
your music. I don't know, it's like all right, one
toy PPM, let's get someone. I mean, if you've listened
to my record, you know that it's it's not like
one slow, one fast, one slow fast. It's actually a
very um there's a lot of mellow kind of you know,

(18:15):
just I don't know byby moments on the record, do
you know what's interesting to me that I didn't realize
until I was just I guess looking at some notes
about the album is because I've been a fan obviously
of the music for a long time. Is that? And
I could be wrong, but is this your first, like
full album first? Really? Yeah? Really? I was shocked by that,
and I thought it was a type of because I
guess I've just spent so much time with your music

(18:38):
that I thought I've listened to a lot of her music.
Surely there's an album. But it also shows me how
I'm gonna get back to it. How I don't think
I lost anything because you didn't put out an album.
I just needed music from you all the time. Yeah, no,
I hear you. That was intentional. It was all kind
of it happened by a mistake, and it was a
very messy. I felt very for straight at a lot

(19:00):
of the time about how things didn't go um because
Side and Side B were supposed to be a full
album and I felt in my heart and my remembering
their albums to me and I don't six song albums. Yeah,
I don't mean that in like, why weren't they albums?
Or what happened I mean again, I'm just going from
how I think and feel about what I've listened to

(19:21):
and why I think albums as thirteen unit entities aren't
as important to be that long anymore. Maybe that's what
I should say. Maybe maybe I shouldn't say albums are
become less important. I don't think they need to be
that long anymore. So you could do a six song
album and not call it an EP. Who cares? Here's
my question for you. Because digital there's no EP. On digital,
There's no such thing, right is it? Does it have

(19:42):
to do maybe with the how saturated how many people
are putting music out, because because if there were people
like if you had all of these Joni Mitchell types
or John Mary even like people that make records because
they it's an entire experience, if that was all you
were listening to, you'd we want the album. I love
the argument you just made. I'm gonna tell you when

(20:05):
you there a couple of words you just said and
I was like, well I just won this one. Sometimes
it's like whenever, it rarely happens with my wife because
she's way smarter than me, and it sucks. I'm not
used to this, but every once in a while she'll
float something out there and I'm like, oh, I'm a
goot to win this argument. I cannot believe it. So
so I love that you use the word winner in marriage.
Good luck. I know, I got a lot of work

(20:25):
to do. Um. John Mayer has also started to put
it out in waves and three songs, and I do
enjoy it all together, but I like to spend time.
I have no I don't have an issue with people
feeding songs out, you know, periodically until the record comes.
But I do think that if it's leading up to

(20:46):
an album, I'm I'm so much more excited about that
because I think you took the time to tell me
something in a it's an art form, there's something here
that it all goes together, and it's it's a collaborative
meeting of like all your inspirations, and it's important. Nobody's
disagree with you. I'm not disagreeming Again. My only disagreement
is if you go, here's thirteen new songs, Oh god no,

(21:07):
because nobody, nobody has time. And you know, the old
album format is it was on a c D and
you couldn't get it early or a single and so on.
People like, I'm a big album person. I hear them
going this is I'm gonna put a couple of songs,
and here's the rest of the fourteen songs. And I'm like, man,
you have so much good work that I hate to
say this to you, but people are gonna spend enough
time with it because it's too much at one time.
Do you think that I should have put out more
songs before I put out the Yeah? Oh you do? Yeah, Okay,

(21:30):
we put out what four? Yeah, okay, so we should
have put out like seven? What do I know? I
didn't know that. I'm a huge fan of yours, and
even now as I've listened through the album on my own,
even before this, but even again, because of this, I
probably haven't spent enough time with some of the songs
because okay, well I love Ben Rector's album. Well I

(21:50):
love Brett Eldridge's album, and I tell him brought some of
of my best friends, like, you can make up more
before you put put out the whole thing. Yeah, that's
only that's only me, but I think that's just the
general culture. We just can't take a whole lot of once.
It's like too big of an awesome meal. Yeah, I've
been saying I've been saying this a lot um, this
thought of like where do we go from here? We're
going so fast and so forward, and I just keep thinking,

(22:12):
when are we going to hit the wall? I'm gonna
tell you only only went ten seconds of a song.
I want ten more seconds of a song every day.
Give me ten more seconds and then what we just
internally combust? Um. No, I think you are swaying. I
mean you're making a very good argument, because there are
artists that I love who have albums out right now.
Their albums have been out for six months, and I
love them, and I'm like, I'm a fan. I'd buy

(22:32):
their ticket. And still I don't know what track number
seven is. And that's your that's at your point, and
I understand that. And if they probably put out two
or three songs at a time, I bet you would
listen and invest in those two or three songs because
it doesn't feel like too much of a commitment. And
it's my point of the albums as a full package,
once fully released, are dead. But I need him increments
me only me, um, and then I need because I

(22:53):
want to spend time with my favorite music and really
get to know the songs, and I don't, and I think,
I I what a lot of consumption is Um, I
don't give enough time to think. This raises a really
good question about how much the artist pays attention to

(23:15):
the audience, because if an artist is making a record,
they are probably you know, in today's world, most of
the kids on TikTok, that's all they think about is
what does my audience want? What songs should I write
that They're going to use that thirty second clip and
put their own video to it. Um. I am constantly
at I'm resisting, and I'm in at war with this

(23:37):
whole concept. It's very hard for me to wrestle with
the idea of like I should just do what feels
right to me instinctively as a human, as an artist,
as a creator. But then there's also this whole other,
you know, argument for paying attention to what people want
and kind of adapting to that. And well, I don't
think you're adapting your message or your content or your integrity.
I think you're adapting. Yeah, but a lot of your

(23:58):
integrity feels like you just tell the same message. You
can put out every one of these songs. You know,
three at a time, for even two at a time. Well,
this bleeds out into so much more. Though there's social media,
there's content, there's how you promote the songs. I mean,
it's not just it doesn't stop. It like, yeah, give
them a song at a time. It's like no, no, no no,
you gotta have a visual for every song. You have
to have a dance that goes with it. You have

(24:20):
to also teach them how to make it. I didn't
see any of your dances. I don't. You have to
have a cocktail that also matches every single song. I mean,
it's like this whole thing it doesn't stop, That's what
I'm saying. And it never will and there is no end.
And are you you okay with that? Like you feel
have no choice? So yes, I have no choice. But
isn't there something to be said for the people that
resist the wave? Like we don't need those people at all.

(24:43):
We do. We need every kind of person. But you,
as an artist, what you were saying a second ago
is you know, I don't want to change how I
feel or question um, but do you want your message,
your true message, to get to the most people. I
guess that's what I wanted of course, okay, And if so,
it's that walking that high wire of man, I need

(25:05):
to do what we'll get to the most people in
the way that matches most with how I want to
present it. And it is, and it's it's never you're
never right. There's not a right answer, and that mind's
not about a message or your integrity as an artist.
It's just about delivery and consumption. And I have friends

(25:26):
that are like, I'm only gonna put out twelve song
albums and I respect that, and I say that's great
because you know the mays you want to walk people down,
but you're gonna walk far fewer people down it totally. Yeah, Well,
and that a lot of your friends probably have the
luxury of people waiting for that album, you know, the
friends you're talking about, it's probably like a million people
are waiting for that twelve times even then not anymore,
not as much anymore. So, Yeah, I think we're everybody's changing. Man,

(25:49):
It's crazy. And am I okay with it? No? I
don't like it, But you have to be okay with
it because if you're not okay with it, you're you're
arguing with the clouds. But you can't win that I
spent a lot of time doing that. Does that show
maybe that's why it took me three years to get
this album out? Why? Why? Um? Well, you know there
was a pandemic. I don't know if you heard, but
I wonder did you hold off or did you or

(26:11):
were you not able to because there's a difference, there's both.
It was both. Yeah, it was. I wasn't ready two
thousand and the end of two thousand nineteen, music wasn't ready.
It was just had just started being kind of formed,
and then uh March everything shut down. Um. I put
out Wait for the Light, which you so kindly supported,
and and we kind of just used that time where

(26:33):
there was so much uncertainty to really hone in on
what the record needed to be. And then um, and
then partner. We had to find a partner. You know.
I didn't want to put it out fully independently because
I really wanted, like you said, I wanted it to
reach as many people as it could. So, um, we
spent a few months kind of meeting with people, and
then Virgin came along and it just felt great and

(26:54):
and then brought us to now. I'd like to say,
for those that are listening, here, I think Jillian are
having this very healthy conversation while we don't have to
exactly agree on everything. And I can have this with
you because I admire respect and I am friends, so
we can kind of do this and it be wonderful.
It's very fun because I massively respect you, and I

(27:16):
think that you have such a handle on um our
culture and like what what motivates people? And also, um,
you're really good at sniffing out intentions when people do things.
I think you're very perceptive and like what someone's intention
is when they're doing something. So, um, every time you
say something, I always take it to heart. I don't. Okay, here,
here's the next one. I'm gonna tell you, And I'm

(27:37):
gonna play some of these tracks that I really that
to me for one reason or other hit me in
a different way. Um. And so the song with t
J Osborne, which you played on my show, God dang man,
it's just it's just the best. It's just the best.
So here's better with a broken heart like wonderful mality.

(28:19):
It's uh, t J is such a great addition to
that song. Just I love the song. What's funny is
I don't actually and I was drawn to that song.
I don't actually feel that anymore about me personally, but
that was my jam forever, meaning that that feeling that, uh,
it sucks. Everything sucks, So I need music that sucks
to go with my socks. Yeah, totally. And so when

(28:40):
I hear this, it reminds me of that and the
most wonderful way and that you know, music is just
to make us feel one way or the other one.
And it's also just my kind of paying tribute to
our love and country music of just the sad pulling
up to the bar, drowning your sorrows kind of feeling
like I grew up on so many of those songs,
and I wasn't in that position when I was thirteen

(29:00):
years old, but I was like, oh, yes, I feel it.
My heart is breaking, like I love just kind of
owning that, and it's just what our you know, what
our genre kind of um embraces when I hear that.
When I heard it the first time, I was like, man,
four years ago, I'd like, this is my favorite song
because I just liked those songs that made me feel
that way. It's like, you know, I just rather do that.

(29:21):
I'm sad anyway, I'm not. I'm not that anymore, oddly
for the first time ever that there are a lot
of factors, mostly it's meeting my wife. But that's such
a strong song that it reminded me of how I
used to feel. And that's a really good thing. I
like that. I like, you know, you have a lot
of songs that actually, um make me feel or remember
that I used to feel things. That's very cool to hear. Yeah. Yeah,

(29:43):
I think there's a difference between like telling someone how
to feel and also letting them kind of find their
way to that feeling. Like there's a juxtaposition that has
to happen between like the lyrics and the melody and
the production, you know. And I think Better is almost
like this, like Classic has like a saloon esque kind
of like you know, raise your glass kind of feeling.
I want to play a little bit of the last track,

(30:04):
and I want to ask kind of the similar question
I did with the first track, and against such this
question would have been awesome for the seventies. I mean,
it really would have been the question. But I still
I'm kind of into the idea of why things are
put in certain places, even set less, like I'm still
fascinated and love to get into the mind of people
who put set less together. And I do mind for
different reasons. If I'm telling jokes that we're doing funny

(30:25):
songs were done. Um, but like a real artist as yourself,
I'm gonna play Honeymoon. I'm gonna come to you for that.
So here's the last track on the record, Honeymoon. Heyst
late with you. I don't know that forever. So to

(30:47):
light on your skin on want it awful? So now
the sky tune and paint in a boom. Oh is
you in the globee? This is you at your best?

(31:07):
Just a piano you can you can hear the uh
perfections and imperfections of your voice because it is it's
so close. I mean, it's it's just that's that's just
you at your best. In my opinion, Thank you. Um.
When it comes to musically, so I'm gonna give you
my idea of what I feel at the end of
this song, not what the song is about, but why
I thinks and you tell me the real reason. Um.

(31:29):
So when I hear this song, I don't hear an
ending to the record. I hear an ending much like
Castaway ends with Tom Hanks and he's at the like
the four way or the road and he's like, all right,
here goes and then you don't know, right, it's it's
it's it's the end, but it's the beginning. Oh god, yeah,
that's very well said. It is the end in the beginning.
So when I hear this, don't don't tell me I'm

(31:51):
right or wrong yet. I'm just out because I'll just yeah,
I hear this song, and I hear and it's like, well,
that's the end of the record, and that's the end
of this. But some records end, and I felt like
this record, this, this ends. Where did we go next?
That that's what I feel here. So you tell me,

(32:11):
first of all, love the song just like I said,
it's you at your best? Why did you put a
track the last track of the record. It's um, you know,
I've always sort of romanticized the like end of the show,
curtain call kind of feeling and record and um this

(32:34):
song was written about my husband, which is a lot
of the record is the theme of falling in love
and really saying are we going to do this forever?
And then I had a baby during the process of
making this album, and I cut this vocal while holding
rockwell he was sleeping, and then I think you can
actually hear him wake up at one point because it's
like a full one take thing. Um, And I realized

(32:57):
that that was the beginning that was also singing about
at the beginning of someone's life, starting and wanting to
hold onto these precious moments of the beginning of him
being my baby and he won't be that way forever.
And um, but there's also, you know, a big question
mark for me. I'm already thinking about what I'm going
to make next, because I do not music, you know.

(33:21):
But um, kind of like you said, like where do
we go from here? You know? This record was twelve
years in the making, no longer because it was the
record I've always wanted to make, and so knowing that
it's out and it's done, there is sort of this
like whoa, Okay, that took a really long time and
it means way more than I ever thought it could mean.
And now there's like this sort of this weird gray

(33:45):
area where I'm like, Okay, where do I go next?
You know? And I'm already thinking about the songs that
will shape the next record. Um, I don't know if
that answers your question. But I feel like i've once
in my life somewhat it hit me the same way
that you were trying to send it out. In music.
You know, it's allowed to hit us in a hundred
different ways. It doesn't matter exactly what you meant. We

(34:07):
all accept and interpret it different ways. That's the point
of it, you know. I don't think you can speak
for yourself here. I don't think every artist puts out
a message and demands it be interpreted exactly as they
said it. I think people are allowed to take and
accept and um understand their own you know, with music
and with At the end of this record, I was like, well,
that's the end of the record. But I just feel like,

(34:27):
to me, it was Tom Hanks at the end of
The Castaway and he's like, it's it's in the movie,
but it's a whole beginning for him totally, so at
the end of the beginning. At the same time, it's
weird to feel like twelve years in like the debut album,
there's so much life in it. And also, yeah, it's
it's a heavy beginning in a way, you know, it's like, wow, here,
I'm gonna dump this all out. I had to get

(34:48):
it all out, and now it's like, okay, let's uh
find a new island. I don't know, you know that's
hypothetically you know, well you I didn't know that you're
holding your whenever you were singing there. That makes sense
to me because you know, as I listened to the
song and possibly my favorite song on the record. Uh,
I did say before you told me that I like

(35:09):
I could hear again your vocal perfections and imperfections, which
is just you singing it all the way through. That's
pretty cool. Yeah, and hoping that he doesn't like start crying. Yeah,
I had to do that quite a few times actually,
so that that song just lovely. I do want to
play a bit of magic, which I guess i've Why
do I know has this song been out the longest?

(35:30):
Why do I know this song so well? It was? Yeah,
it was the first one we put out. Got it?
That makes sense? That makes sense? And I wrote it
like five six years ago. Here is Magic from Jillian
wasgic just Slee Jack Druck just to social media. Yeah,

(36:05):
I saw you a post and I knew where it
was going. Um, and it was like great thematically, but
you're posting iconic do a couples? Maybe A first it
was just it was couples, right, not sing sing singular
people A couple That was yeah, and so I knew
it was something. I knew it was building for that,
but I thought it was really cool. And I didn't
know if it was going to be iconic or I

(36:26):
didn't know. But so I'm gonna play this. We'll talk
about that, but here is um iconic tweet? Did sweet

(36:49):
we could be? I'm gonna go a little backward here,
but so that's that's ten Honeymoons eleven. So we're with
the last track. Those two, to me, more than any
other couple of songs, felt like they were brother and
sister songs. Yeah, definitely, Well, yeah, I think thematically, you know. Yeah, Um,

(37:13):
I know I felt a little risky putting those songs
next to each other too. I was like, are people
going to fall asleep or they get just gonna cry?
Who knows? Um? Yeah, so that song um I wrote
after I got engaged to Brian in Paris, um under
the Eiffel Tower. And you know, there's a lot of
this record that I kind of wanted to feel like
you're walking through the streets of Paris or some beautiful

(37:34):
like you know, European city or something. And um, this
was one of the first songs that we started playing
for people, and it was actually Karen Fairchild. I have
to give Karen props. I haven't told anyone this, but
when we played her like four songs off the record,
Iconic was like the last. When we played because it
was really slow and just emotional, We're like, you know,

(37:54):
she probably won't want to hear that, and then we're like,
we'll just play this last one, you know. And after
hearing all the other songs, she was like, that's the
one and I was like, what do you mean. She's
like that's the song, Like that's the song that people
are going to hear and like get it. And I
was like, oh okay, wow. And then she was like
and I want to shoot the music video for you
in Paris and I was like, are you gonna fly
us there? That's so great, let's do it. Um. But yeah,

(38:16):
you know, Iconic is you know, for me, it's this, Uh,
I'm diving into that idea of being scared of forever
when you come from divorced parents, um, you know, not
knowing what that feels like and feeling like every second
the other she was gonna drop, and like someone's gonna
just leave and you're not gonna be able to get
through the hard times, you know. Um. And it was

(38:37):
just kind of my my very vulnerable, naive question to
Brian of like, what if we did it? You know,
can we do it? I'm scared? Are you scared too?
And it, uh, it's a very emotional song for me
and I you know, convinced him to be in the
music video because it's a little voyeuristic, but we played
all these this footage from my wedding day, um, and

(39:00):
it felt very brave and I was I was actually
really proud of myself because I can be a very
private person with my personal life, and it was kind
of my way of declaring to the world like, whoa,
I got married and now we've got to make it
work forever, you know, and you just got married, so
you know that feeling right? Yes, I you're talking about
things that that I struggle with as well, meaning you know,

(39:22):
the parents thing. And I always and listen, I'm in
therapy often where I always feel like everybody's leaving because
I always have and so when did your parents get divorced?
How old were Okay? So, I mean very much a
time when you're figuring out who you are. UM, so
very much, and it's gonna scar you at any point,

(39:44):
regardless if it's six or twenty two. But I think
the scars are are different length and depth depending on when.
Thirteen is pretty rough time. I think to have to
have it split up. Um, your relationship with both parents
was it good? Was there at the time? Was there
a villain? My mom was the villain and she has
since not. You know, nobody's the villain anymore because marriage

(40:05):
is hard because you know you I know them both,
and you know the world. You know, Yeah, I have
grace for things I couldn't have when I was thirteen,
and that's you know, that's on me. It's Um, I
definitely villainized my mom. Sorry, Mom, I'm apologizing publicly to
you now because I was a bratty little thirteen year
old that was like why why you know? And you're

(40:26):
you're too you're too cognitive, you're too aware, and you're
kind of like, what can I do to fix this
between you guys? I literally remember sitting them down and
I was like Okay, I know things are getting hard,
like is it me? Like what can I do to
fix it? And that was like they they've told me
since then. That was kind of the first instinct or
indication to them that I was very empathic because I
got and maybe egoing. I was like, it's my fault,

(40:49):
It's all about me. But you know, I think as
a kid, You're like, I gotta fix this, um and
I couldn't. I couldn't fix it. And two people that
I thought were so in love and had this perfect marriage, uh,
chose to leave each other. And so there was this
brokenness when it came to commitment for me, and and
Brian knew that. And you know, it's very understanding to

(41:11):
that my wife deals with that with me, and that
you know my you know, mom had a pregnant fifteen,
and you know, my dad was seventeen. I don't he's
not my dad. Will call my dad, but you know
they were together for four or five or so before
he left, and it was just anybody that came in
and now always went out. Ever, so even my mom,
you know, I don't you know she when she died

(41:32):
in her forty So I just never expected or and
I'd given up on hoping that anybody would stay ever.
And it takes a really specific, compassionate, special person to
know that about you and also to somehow instill trust,
like I'm going to be here and it's tough, and

(41:58):
it's it's me. She's awesome, and she comes from two
parents that still are together and love each other, and
she had that example, she had a she had a model,
and I don't, and I just think that everybody's gonna
always leave, you know, And that's what we did. That's
inside even when my mind says, okay, look at this logically, yeah, well,
that goes into your defense mechanisms and your your your

(42:21):
panic mode when you know the fight or flight. You know,
that's like obviously your therapist probably talks to you about that.
Mine has definitely talked to me about it. Where you know,
you have your go to and you learned it very
young how just survive and how to take care of
yourself and trust me, there is that escape pod in
the back of my mind where it's like, okay, so
in case this happens, so we're gonna do. What you're
gonna do is gonna run down these stairs like it's

(42:41):
real and my wife's always like, hey, I'm not leaving,
and she's like, every time we disagree, that doesn't mean
this is some huge blow up. We're never going to
talk again. I don't she because she knows I like
go e to z immediately. Oh yeah, yeah. Are you
the lean in person or you the retreat like when
when things completely I I have isolated my whole life

(43:03):
and that's been a struggle for her to deal with
because she's very much talk it out. Let's spend time,
let's sit down, let's figure out what the root is.
And I just want to go and be alone and
figured out myself because I spent my whole life being
alone and figured out things myself. Yeah, and you feel
like that person is not going to be able to
hold space or understand and she can't because she hasn't
and I can't understand her. But we're learning to actually

(43:25):
understand our process better and that we don't understand the
early building blocks of each other because I don't know
what it's like to have two loving parents. Now that
means say they're they're they're different dynamics with that too,
that I don't understand that good and bad. So when
you say this stuff. I'm like, yeah, they just play
guitar behind that, sing this to me because this is

(43:47):
a song. Totally, it's like, what is your what are
your defaults? Keep kicking? Yeah, I mean I think Brian
also came from very, very happy, you know, a wonderful
home and his parents were still together, and it's just
his default is like, oh, we're gonna be okay, everything's
gonna be fine. And that's not mine. It's you. It's
exactly same, exactly the same. And I know it's not
my default, but yes, I mean this is this is

(44:11):
the same. But I get to have a problem with
Brian to come from a loving fan he wears too
much black. You can't wear that much black and come
from that much love. Well, yeah, we gotta stop that.
Stop being oh my god, totally they called him. I
mean he so Brian is sort of the anomaly of
his family. I mean, you know, to fare well enough,
you know my producer, and uh, Brian is I I
joke and say he's a vampire because he probably would

(44:33):
stay in his studio in the dark all day every day.
That's his happy place. He's a very he's a very
you know self sustaining, um independent person and that's what
I love about him, you know, And I'm that way too,
But also in relationships, I'm much more the I don't
know if you call it um anxious attachment where you know,

(44:56):
if there's something going on, I will be like, wait, wait,
what's going on? Let's fick sit you know? Are you
fixed too? I'm trying to I'm trying to fix all
the time. Yeah, I'm learning that I don't have to
try to fix and sometimes it's not to be fixed. Yes,
And that's hard. It's really hard because I can't physically.
It's almost makes me sick when things are off, like
I feel it internally. It makes me uncomfortable to not

(45:19):
try to fix something that isn't whole or right, and
I'm just supposed to sit in it. It's that's so hard.
And you know, my extremely balanced wife is like, hey,
sometimes just sit here with me. You have to fix it. Wow.
And that's the hardest thing. Your skin is like crawling.
Oh yeah, I'm like no, no no, no, I need to

(45:39):
fix it right now. Because if you're feeling this is
not good for you, it's not good for me. So
I'm gonna fix it and She's like, I don't need that.
I just need you to be here with me right now.
Do you guys do couples therapy? No, yes, and what Yes,
but not as frequent as we should. We spend a
lot of time um in therapy apart and we have,

(46:01):
but not every week. I guess it's my answer. I
hate to commit and say yes we do when we
we weren't consistent with it. But it is very important
to us to go to therapy and try to figure
each other out and then work on ourselves together. I
think that's so smart. We're we just started doing it together.
We should probably go every week just for maintenance. Everyone should.

(46:21):
It never gets to a point where you feel like
we got to go to therapy. Um. But we we
work on ourselves and and together enough that as long
as we're going my individual therapy that was so important
to me. Yeah, it is. If I don't go, I
spiral quick, um A spiral quick. It's crazy, especially coming
from your background, you need that objective just listening ear

(46:44):
you know. Yeah, opporctunities. The thing I didn't understand that
I would value the most. Yeah. I never thought I
would want somebody to have any influence that actually didn't care.
And what I mean if I don't care is it
doesn't affect their day the rest of the day. Right, Yeah,
But I need because I need somebody who does infect
the day the rest of the day to actually give
me their objective opinion about stuff. Yeah, even with art, right,

(47:06):
I think to have that. I hate that. I mean,
it's great, and just let it go. I don't want. Okay,
I like that. It sucks. It sucks, but it is
what I feel for me is most needed at times,
even though I hate it the most. Who. So, who
in your life do you get professional feedback from. I'm

(47:28):
gonna tell you you used to be nobody. I just
wouldn't accept it because I thought because I don't have
any mentors in any business. I just always felt like
nobody understands it. I'm doing it differently, not because I'm like,
I have this great idea do differently because I don't
have a skill set to do do it like anybody else.
So I figured out how to do it in ways
that nobody else did. Yeah, I was so advanced, but
oh I can't do it that way. So how am
I going to figure out how to get there? Through

(47:50):
digging under the dirt instead of climbing the ladder. You
know there was no blueprint already there for you. Yeah,
and if it was, I wasn't good enough to use.
I don't. I didn't have the skill set to actually
use the blueprints. So that being said, I never trusted
anybody to tell me what was good or not. UM,
and I struggle even today. And in my last book,
I guess I'm my last book. I have a kid's book.
UM sent you a picture. I know I was gonna

(48:12):
give you one with with with an autograph, but who cares? UM?
So my last book fail until you don't. I wrote
a thing about it's hard to trust people that say
that you're wonderful if they also haven't in the past
been accurate when they told you you're not, because it's
easy for someone to go it's amazing, and for you

(48:33):
to believe it if you're not. It's it's easy because
you just want to believe you like, please give it
to me, Give it to me. But if you have
that trust with someone who's come to you and it's
been very uncomfortable, and they've said, I don't think this
is the best, or I don't think that that sucks,
and that in that instant you may not be better
from it, but you can actually trust them when they
say the opposite. Yeah, I know, and that's important. I'm

(48:56):
still working around the shame feeling that I get when
I hear something that's you're not great? Yeah, so how
do you? Because I'm still really wrestling with that even
with my manager, who I respect, and I want her
to tell me the truth, you know, Melanie, she uh
if she's ever like, you know, I don't like what okay,
what do you mean? Like what you know? I can't
handle it? And I'm like, that's not okay either, But

(49:16):
it's okay not to be able to handle it. I
don't handle it well, but to what is happening in
somewhere deeper where it's like I'm believing that you you
have to have this reserve of confidence. You know that
and you but you do you have a different reserve
of confidence. Now here's what I want to say to that,
because I think we have a lot of similar struggles.
I am. I'm just I'm not confident in a lot

(49:39):
of things, um that you would think I would be. Yeah,
so you fooled me. Yeah, that's the plan right right,
and so um and I am very I'm like, I
create and I make jokes like ours, but I do
create a lot of things, and I'm very sensitive. I
think if you're you're creating, you want to put things
out that people enjoy, consume, live by love, and when

(50:00):
they don't, it hurts, even if you don't let it
be known that it hurts. UM. And so I struggle
whenever I don't hear what I like. But what I've
learned is that it never is going to feel better.
But I've learned through experience of having it happened so
many times that it usually ends up better for me.

(50:21):
And A It's like an investment. I treated like if
I'm investing in some putty money and something it sucks,
I gotta pay money and maybe make more later or not. Um,
but it's usually a good investment comes back to you
later and you're like, well, I'm so glad I did that.
It hurt for a second, but I'm glad I did it.
So when that person who you trust tells you that,

(50:41):
do you have a hard time staying close to that person?
I get so offended and I recoiled almost and I
want to lash back out for not even depending on
what they said, they could be absolutely accurate and they
could be saying complete truths. But I'm so defensive and
scared that they're right that all I want to do
is be like I'm still worthy. Oh god, yeah, I

(51:02):
feel that. So I actually isolate, like I I in
some part of me hate that person. I'm like, I
gotta hate you now because you don't think that I
am everything that I'm supposed to be telling you that
I am. It's terrifying, like, oh god, they're seeing something
that I'm not supposed to be letting them see. Yeah,
and you it's very vulnerable. Um and so I didn't

(51:25):
have somebody for a long long time that I really
would trust with that um my harshest critic. And on
the flip side of that harshest critic, maybe isn't the term,
but for this to make it easy, who will come
at me the quickest and say, hmm, I ain't good
And we'll also say, but I know when they say
that is good, that they're absolutely telling the truth. Is

(51:47):
my wife. She's so funny. She will fix jokes for me.
I'll show go out and watch me do a set
at the operry or I just a couple and she's
like all right. And I used to get so mad.
I'm like, what are you know? And I wasn't mad
because she wasn't good. She was actually she was right,
and I was so offended that she was right. I

(52:08):
would I would have it get mad. And she would go,
you know whatstide of that joke when you're talking about
this dream? What if you said it and you kind
of walked him over here and then you flipped it
and into the joke like this, you're saying exactly the thing,
but it's like a few different words and you're good.
And the first time she did that, I was leaving
the operation. I felt like it just crushed. I did
like thirteen minutes and some new material, and that's an
older audience and I don't really expect to crush with

(52:28):
the operation ever because of the crowd. But I just
let him have it. And I was feeling great and
I was driving back and I was like, man, it
was really great. She was like it was great, and
she goes, now, do you want it to be better? Oh? God,
that wouldn't really get me, yeah, And I said yes,

(52:49):
I didn't. I didn't want to say yes, but I
feel like I had to say yes. And she said
that she telled me how to fix this joke, and
I was very offended, you know what. You know, I
tell the joke now the way she told me then.
But you were you were coming off the high of
the show, you know, and that takes a lot to
go out there and tell your jokes, and you were
feeling that, and then in some ways you were probably like,
oh God, why now come on, let me just have
my moment. I'm glad she did it then, and she

(53:10):
knew it too because I was still in it. Yeah,
she needed me to be in it so I could
actually reflect on why what happened could have happened a
little better because I just in it. I love that
it's weird. It's weird, and I get so upset and
now the growth in me and it's not always the case.
But um, I've put together this show. It's it was
an hour and a half the last time we did it.

(53:32):
I did two shows this past weekend, and I've built
this entire show with a little silent films in it,
and it's it's comedy and motivation and it's this show.
It's very vulnerable. It's quite funny. Um, I've not seen
a show like this before. And I said, you know
what a tackle this thing. I spent three or four
months not only writing the jokes and creating the stories,

(53:54):
but conceptualizing the videos that run on the screens. I
paid extra for all these screens to go up in
the theater, and I said to my management team, I said, hey,
I need to do not one night at the rhemants,
I need to do two nights or three nights like
a thousand, because I need to do it a few times,
a couple of times to make sure that, um, I'm

(54:15):
doing it right. Because I have to go out and
and works workshop stuff with real people. I can't practice
guitar and then have it. I have to go and
get reaction. Oh it's a joke, it's a story. I
can think that something funny. Many times I think something
hilarious and I go out and nobody last or even
thinks that's a joke, And I'm like, oh God, that
wasn't a joke at all, was it. So I do
these shows and this is where I just it's funny.

(54:37):
Bring this up as I finished show one, and is
good for for a show one, and this whole new
idea that I had is slightly clunky, but I thought
it was really good to give it a B minus.
And you know, I went to her and I was like, Hey,
what's up. What are your thoughts? And she was like,
it's really good. She was like that show mattered. And

(54:58):
she was like, I think it's the first thing you've
done where people that have no idea who you are
if they happen to see, Oh, let's go to the
show that's in this theater they walked and they'll be
like I love that because you have your people and
the people that you talk to in the kind of
she goes, but I think this is the first thing
that I've seen you do that. It's just like, straight up,
somebody can just stumble on Netflix and like that's and so.
But she's telling me this and I'm like, wow, she

(55:20):
never says this, not in a never in a bad way,
but I believe it so much. And then she's I
was like, well, what can I do? How can I rete?
And then we sat and we rearrange stuff, and I
just loved that and trusted that because of the uncomfortableness
that we had when I wasn't comfortable enough to take it.

(55:40):
I do have that. Yeah, I'm really proud of you guys.
I'm still working on that with my husband. I don't
think you'll ever figure out or will I ever? But
what's that like for you with folks? He is that
person for me too, so so he is a lot
of Caitlin where he's very honest, brutally brutally honest. Like
even the other day, he was like, sometimes I feel
like you post photos of yourself that don't really show

(56:01):
how beautiful you are. And I was like, which one
that's a compliment and it's all the same time, wow exactly.
I was like, well, can you show me on my Instagram?
He's like, I don't know, You're just like so beautiful
and sometimes you post a photo and he said it
makes me wonder what you think about yourself. And I
was like, okay, let's just unpack this. But when it
comes to like shows, if he's like backstage and he's like, wow,
that was really good, I'm like, Okay, that was really good,

(56:22):
you know. Or if he's like yeah, yeah, it was good,
you know, like I just know immediately and thank god,
but I'm still not comfortable I'm not where you are.
Where I'm like, hey, baby, will you tell me like
what I could do better? Like that is where I
need to really work because right now it just makes
me feel like failure, failure, failure. You know, you're not
perfect and we got you know that's a huge issue

(56:43):
for me and me too. Yeah, and you will absolutely
get there, especially if you respect the person who's telling
you what they're telling you, why they're telling you it.
I hate I hate people to be like I don't know,
I don't know this what I hate it. I mean,
it makes me feel like I'm not worthy. Period. I'm
not good enough. Do you think I'm not good enough?
All you're doing is validating the fact that I already
think I'm not good enough totally. That's what it is.

(57:04):
That's honestly, get down to it. I don't think I'm
good enough. I'm hoping I'm fool on everybody. You're reminding
me that I'm I'm right. I'm not gonna so I
just have to ask because you've you've been so successful
and you it seems like we connect a lot on
that inner monologue that's happening. You know that we grew
up sort of believing this, if I prove myself that
I'm worthy, then I'll be good enough, then the world

(57:24):
will love me, then I'll be successful. So despite those
you know, do you feel like a lot of the
people you meet at your level, at your level of success,
just have this inner confidence and you're like, WHOA, Like,
why don't I have that? Or is it kind of
like everybody has that thing? A little bit of the
second one. I think everybody has a little bit of
imposter syndrome. Everybody. Okay, I do, I think, but I

(57:46):
think some people that have an absolute skill that has
allowed them to develop a confidence that's unquestionable because their
skill is so good. And I don't have an undeniable
skill that I can present to someone and be like, well,
regardless of the whole world field, I'm not Mariah Carey
with a voice like that. Who is she can be

(58:07):
the biggest dev in the world. Everybody hates her. She's
still freaking out her voice. Maybe now she's the holder.
But you know, um, so I have imposter syndrome because
I don't feel that I have a skill I can
present and go regardless, I still got this. I don't
have that thing, Okay, I feel like you do have that,
but I don't name it name. I mean, I think

(58:28):
you're exactly you can't name it? No, no, no no, can
I say it? I was already feel unomfortable. Wow? Really no? Okay,
do you know like why, like David Letterman is like
you are that? Like that's a skill, like an interviewer,
being able to actually like have a conversation with people
that the public wants to listen to. That's an actual gift.
But it's not. It's a It's a skill that I've

(58:51):
developed and that I didn't do well for a long time,
and I couldn't do it like the greats did it,
so I had to figure out a way. You don't
think that it's a skill to be so interesting to
people that they just want to hear you talk. I
think that at this point, I've been through a lot
of crap and I can my superpower here you go,
let's get down to it. My superpower is empathy. Yes

(59:13):
that I don't feel sorry for you. I in many
ways understand where you're coming from, so I don't have
to shy away from it, and I can go well
because I relate to you. Whence your parents get divorced.
I don't have to. Yeah, and so and then you
and then you don't go. It's weird. It's not really
your business to get any deeper in that. But but

(59:34):
you go, Well, he understands that I can talk with
him about it. That's that is It's that that is
a skill. I will argue that is a skill. No,
it's an incredible skill. There's so many people that I've
sat in the same position with and I feel guarded
and uncomfortable, and I want to leave the room and
I don't want to tell them anything about myself. Fair

(59:54):
I will say, that's not a skill I've developed. Um,
it's not a talent. I've developed a skill. Also get
a fend people time. I'm talented, really very very offended. Yeah,
why because I've had to work for it all and
I don't feel like I have a natural talent, okay,
And so when people go you're so talented, I'm like,
you have no idea at the hours I put into
this crowd. It's dumb and I shouldn't And and I

(01:00:17):
was talking to Breland. He was like, yeah, you're basing
that off intention. You need to base it off intention.
They're being nice to you. They are and they're not
saying that you didn't work hard for what you have,
and so I struggle with that. I could see that,
and I can see he also probably understands that very
well more than anyone um because you've had to work
tenfold because of where you came from and what you're
trying to do. Sometimes I think you're such an anomaly

(01:00:40):
to me because there doesn't seem to be a limit
to what you're capable of, which is a lot of
people have that one thing that they're really good at.
And it seems to me, like I've said this to Branam,
like he will become like a governor. I mean, he
probably could be president. Like I actually think that there's
nothing that you can't do. It's funny that that's what
you think, because in a weird way, it's the opposite.

(01:01:01):
For me. It's where I feel like I have to
try everything. I have to like I have to go
at everything because I really don't have one thing I
can rely on. So this is just, yeah, that's the truth.
I feel like I need to try things and try
at all because I have nothing that I can Is
it like panic diversity? You're like, I'll diversify myself absolutely,
maybe not panic, but fear diversity. So yeah, well, okay,

(01:01:24):
See mine is the opposite where I only think I
can do this one thing really well, and I still
question if I can do it well at all. So
I just do it constantly to the point where I
don't do anything else. When you've finished the record finished,
whenever you heard all the tracks, fully mixed, everything done,

(01:01:47):
We're okay, we're sailing it up. Turn the key. When
you listen back to all of it, what song were
you most proud of? And it could be one we've
talked about already, meaning the message sonically, you're like, we
really captured whatever that is, We really captured that. What
was that? Honeymoon was definitely that for me. I was

(01:02:08):
very proud of that, um just because bare bones, you know,
like just a piano and a vocal. I've never really
done that and it felt very brave. UM. And then Hummingbird.
Hummingbird was like, that's a song that I listened to.
Is if it's not mine, you can do that, Huh,
that's awesome. I listened to it all the time. So
this is so weird to say, but I'd never done that,
and I actually, I'm like, I want to listen to
Hummingbird right now. Um. Somehow, writing that song was very fast.

(01:02:32):
I wrote it with Daniel Tashin and Andrew D. Roberts,
and it was such a quick session and I kind
of feel like Daniel has this jarring, sort of unum
disarming way of kind of being like you want to
be vulnerable and then you are and you're like, oh god, wait,
oh okay, is that okay? And so we wrote it
and then when I listened to it later, I was like,
oh wow, this is about my parents and me and

(01:02:54):
my fear and running from everything because I'm so afraid
that I'm not enough. Okay, Well, and now I listen
to it and I'm like, it feels like I'm listening
to another girl. I don't know. It feels powerful. Here
is humming Bird every time it well, thing a song

(01:03:25):
good in a tree, so simple and so sweet? Wouldn't
that be easy find a place to rest, to be
done with discontent? Sometimes I wish it weird to look
at something that you've done and be able to appreciate
it as something that you just appreciate it as something

(01:03:47):
that's not normal like other things you've done because occasionally
I'll have that I don't know if you've heard song
Hobby Lobby Bobby, but it's pretty fairs No, but you know,
it's every great. Once in a while I'll be like, damn,
I'm quite proud of that. It's rare, but it's even
more valuable. And it sounds like that's the case here
with how I'm bird for you it is. Yeah, I

(01:04:08):
think it's a new concept for me to sort of
open up about being fearful and anxious. Um, owning that,
you know, instead of being like, oh, no, I'm easy, breezy,
I'm I'm happy, everything's great. You know, it was a
little bit uncomfortable for me. Um, I can't even I'm
like not even looking at you as I'm saying it
because it's so uncomfortable. I'm like, yeah, I'm anxious. I'm

(01:04:29):
an anxious person, like I you know, I make sure
that I take things that make me less anxious. Like
that was a whole thing for me in life, was
accepting that I have anxiety. It's fun. Um, we're on
something we're talking about earlier without realizing it, where you know,
you were like, I don't know that I can do
that yet is to just take it from somebody and go,

(01:04:49):
you know, this is why I didn't think it was
as good as maybe you did, or this is what
you can do better. You know ten minutes ago that conversation,
you've done the thing in other parts of your life
to grow an area you just talked about it there.
It's just uh doing it and saying please do it
to me. It sucks because it's exposure therapy and it sucks,

(01:05:13):
and I just say it one time. It sucks. It's
never easy, but you actually get so much better at
it after it's done, and you realize every time that's
someone let's issues Brian for example, Uh, you know you
write a song. I'm gonna create a scenario here, so
just allow me to do so. You can write a song,
and let's do it. He goes, Um, it's fine. You know,
I don't really understand why you said this, or I

(01:05:35):
don't know that the melody here kind of matches. And
you're probably pierced because you felt like you did a
good job. But the more times that you actually are
open and invite it to happen, the easier. Easier is
not a good word. The quicker you can learn from
it and be better and actually help other people at

(01:05:56):
the same time in the same way. So we was
thinking about because you asked me, like, how did you
do it? Just exposure? I think you're you're on too exactly.
What makes like great songwriters great? Like they don't take
it personally. They ask for the feedback like I feel
like Shane and take it very personally. Yeah, well you do,
but and I would too. But I think that people

(01:06:18):
that are able to separate that you know, their work
from who they are, which I can't do. I don't
know how to do that, but it would make it
a lot easier. Just rip the band. It doesn't have
to be songwriting. It could be you know, anything you're
talking about creatively where you're like, you know, how do
I how do you hear from somebody you care about?
Do you suck? Yeah? See, I'm afraid you're right. I
just need to keep doing it and just make it easier,
because right now it feels like if I actually opened

(01:06:39):
that door, I would spiral so far and quit music.
And you will spiral music, and you may quite music
for a second, and then it may happen again. You
may spik a little less, quit music. For a less
time and then eventually you just go, oh, this sucks. Yeah,
but I actually get to grow. This is this is
my growing pill. Yeah, and it sucks too. It hurts

(01:07:00):
to grow, growing hurts or anything. If you're twelve, when
you're growing as a human being, you're at that age
where you're growing, or if you're having to grow because
something happens in your personal somebody that there's all these
growth never feels good. Ever it does afterwards, once you're
taller or you're smarter. Are you able to kind of
gauge like in life when you're in um are you
feel do you feel like you're constantly growing and craving

(01:07:22):
growth experience? I don't know. No, I don't want it, okay,
because I feel stagnant something I don't want. I don't
want it. I don't like it hurts, it sucks. I
want it to be so perfect there's no need for growth.
But I have to understand and realize that's not the case.
And there are sometimes where I don't have the ability.
I don't have even the capacity to take growth right
now because I'm at I'm in a not in a
good place, and so there are times where I just

(01:07:45):
can't emotionally take growth. So we're just good but not
not often. But but when it's that, I know that,
I know it's. Um. You know, I will write something
and you don't have a management team and one of
them be like, you know, I don't know about that,
and I'm like, I don't. I can't right now. I'm
gonna come back to this and then I'm gonna take
this in. But right now I'm just not in a
good place with it, like three things. So I hold

(01:08:07):
you back, but I'm gonna take in a little bit. Well,
that's good that you know that about yourself. You know,
I root for that for you because I because I
know it, because I was there. That's why I guess
that's why I'm rooting for me. I guess I'm rooting
for you in that situation. Um, you're just listen. I
just I just think you're just the greatest, just in
all the ways as an artist. Obviously, I love like

(01:08:29):
your voice and your sound and your songwriting. And you know,
you're not so bad as a person. Your husband's okay
too makes me uncomfortable, Yeah I should, because that you're
the kind of person that would make me too. But
you should know that, Like, I have the most respect
for you. Thank you as a person and as an artist.
I'm and I'm a massive fan at the same time.

(01:08:51):
So it's like I would pay money to watch you
do a show, and so it's all those things. And
because of that, I hope people go and they check out, honestly,
and it's just a great I'll say, it's a great album.
We need more full length albums. That's we come all
the way around. This changed your mind with the eleven

(01:09:11):
songs that I dumped on the world way too soon,
not too soon? Maybe if maybe, if a few more
trickles and between, well, I'll tell you that there is
another song coming. Um, it's actually a re reinvention of
an older song with one of my favorite bands coming out.
And uh, and you know, I waited too long to

(01:09:33):
put this record out, and now I'm on the train
of like not stopping. So we'll just kind of keep
it going. And so I will be doing what you're saying,
I would just be putting out so well not for
a while. I'm not gonna catch up and listen to
these enough. See, I'm just in a bad a few months. Yeah,
just only listen to my album for the next month.
Maybe that's it's it's tough. That's tough to do, but
it is great and it is up there, and the

(01:09:54):
ones that I will listen, I've got about four now
and I'm like, what mood I in yep, and this
is definitely I wanted them. Um, and we only have
a couple minutes left. We already done over an hour,
which is so easy to do with you, which, by
the way, it's been awesome. Hope it's been fun for you. Uh,
album music right now that you're really into for whatever
chapter of your life now. Um yeah, I mean like you,

(01:10:17):
I only kind of listened to a few at a
time and I kind of just like play them over
and over again. Um My, coach, I love Madison Cunningham.
Do you know Madison cunning him. You're going to say
all these artists that I don't know because you're way
cooler than me, so I don't. But you can just
keep talking about really drawn to female artists that can
play really well and have something to say, So Madison
cutting them. Yeah. Maddie Diaz is another one that I

(01:10:41):
put on all the time. She's a friend of mine
and she's incredible. Um, you know, Ah, it's tough. I
go to a lot of older things. You know, I
listened to a lot of like Simon and Garfunkel, like
greatest hits. I'm not really up on like what's super
hip and new right now? Um well, some would say
it's super hipp new to say Simon and Garfunkle, I'm
just saying, really, I don't know about that. I was

(01:11:02):
listening a couple of days ago on Diamondson. I'm a
big Paul Simon fan, just love, but that's super hip.
You're want a Judge T shirt and you're like, that's
all but your hip. I don't think I am. No.
I think I'm actually the opposite of hip, which maybe
maybe that's it, right, I don't know who knows, But yeah,

(01:11:25):
you go to any shows? Get is that? I know
you have a baby. But let's let's say, well, I
like small shows. I don't like going to big shows,
like I don't really crave going to the arena. Um.
I did go to see John Marrith Arena and it
was great. I loved that because I love John Mayre.
But um my, my dream is like going to see
a singer songwriter that I really love like at the

(01:11:46):
basement and like just dealing with like a hundred people
and that's fun for me. Yea. But yeah, I do
go to shows. That's cool. Yeah, that's that's a thing
to say, like that tip. Yeah, well so hit, I
really do like feeling in someone's window and watch him
sing alone. I'm so yeah, Yeah, I don't. I don't

(01:12:10):
get to go to a lot of shows anymore because
not home a lot, traveling a lot, um, So when
I do, it's very valuable. We went, We're going Saturday
to watch Ben Rector. I love Benn. He's a friend now.
Um in his record now it is like a chapter
of Caitlin and his life all the time. So all

(01:12:30):
those songs remind us of this this time period for us. Um.
Brett's last album that just came out, Brett Elder's last
album was really good because it's like, uh, singer songwriter Brett.
I love all that stuff that he does. I mean
I toured with him when he hadn't done that yet,
and then this album came out, and I mean, he

(01:12:51):
just has such a fantastic voice and um, yeah, I
think he's diving in really deep now and kind of
without fear, even though it could, I won't say be disastrous.
He's got a great career, but he's risking a bit
because he could easily put out three minutes yeah tempo bangers,
but he like, I don't want to. I want to
talk about growth though. That's exciting to me. I feel

(01:13:13):
like I'm watching someone grow in real time and it's
really exciting. Um, having a girl's latest record is really good. Really,
it's really good. Okay, well, I have a dance record
for you. I love having a know but Caitlin will
love it. It's lucious, you know, Lucius. I just saw
them at the Rhyme and there to two girls and
they are I mean, I never do this, but I
was like standing dancing the entire time. I'm usually like

(01:13:35):
the curmudgeon, just like sitting down like listening, like you know,
so serious, but I was dancing and singing along and
laughing and it was like so much fun. It's also
incredible that you can do that, because I can't really
do that at a show Mom's night out. It's hard
for me to like, let lose at a show and
dance and have fun. It's not very hard, it's hard.
I actually get mad at people when they do it.
I'm like, can you start on? Sit down? Oh no.

(01:13:56):
There was this guy at John Mayer that was just
like just bopping the whole time and I was to
get out of the way, man, but he was having
a great time. Yes, and this is not what it's
all about. Yeah, okay, everyone everyone listening to this. So
she's Jillian Jacqueline. Her album is honestly, we've we're gonna
end on playing some Bandwagon, which is the current single,
and we're gonna play it out and then we're gonna go.

(01:14:18):
And I'm glad we get together because um I got
sick and we didn't weren't able to it last time,
and the time before that, I think you just forgot it.
I was fifteen minutes later and then you can't. You
said no, don't come, but I was ten minutes early
this time to make up for it to be fair,
and it's unfair as well. Uh, you're accurate, And I
did say that. I just I'm on stupid calendar. Oh

(01:14:40):
I know, I know. And I actually was so upset
in my car. I was like, oh god, and I
saw I saw your manager at the opery and she
was like Jillian so sad, and I was like, I
don't know who that is. I don't know her name,
so I knew you were going to do that. I
was terrified in my cars, like he's gonna hate me.
He's gonna be so mad. He hates when people are late.
I felt so bad. Okay, here is Bandwagon, Jillian. Great
to see you. You You guys, follow at Jillian Jacqueline. Go

(01:15:02):
hit her up when she gets back on the road,
go see her. Just listen to the record stream the
crap out of it. Here is Bandwagon, Go ahead again
on this one is almost gone. Hat on you lift
those fifteen minutes like where the sun says, will follow?
Who's the next piece? Lines of kicking it up days.

(01:15:24):
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#351 - Jillian Jacqueline on Recording A Song on Her Debut Album While Holding Her Newborn + What She Learned from Her Parents Getting Divorced When She Was 13 + Debating Albums vs. Singles with Bobby

Episode Transcript

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Bobby Bones

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