May 6, 2025 • 42 mins
When does structure become a cage?
In this coaching session, entrepreneur Ryan Estes explores:
- The tension between productivity systems and creative spontaneity
- How success can disconnect us from original passions
- The walls we build that eventually imprison us
- Finding harmony between responsibility and authentic expression
For founders feeling successful but unfulfilled, this episode offers a framework for reconnection with what once sparked your entrepreneurial journey.
Enjoyed this episode? Ready to take your leadership and personal growth to the next level? Please visit my website to learn more about coaching with me.
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Transcript
Episode Transcript
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Speaker 1 (00:00):
Welcome to Slow Down and Speed Up, where we have real
one-time coaching sessions withstartup founders working
through the challenges ofleadership.
I'm your host and executivecoach, brian Wang.
Today we're joined by RyanEstes, a founder who once toured
as a musician but now runs hislife on tight schedules and
spreadsheets.
He comes to the session askingthe question how do I balance
structure and creativity betweenthe artist and the operator?
(00:22):
As we explore this tension, wetouch on something that's a bit
non-obvious the productivitymechanisms that help us succeed
can also end up cutting us offfrom joy.
For Ryan, this manifests aswalls built between his
responsible business self andhis creative musical identity.
Many founders experience thiscompartmentalization without
realizing it sacrificing passionfor productivity, creative
(00:45):
expression for control.
If you've ever feltdisconnected from what
originally inspired you or sensesomething vital has been
missing from your leadershipjourney, despite outward success
, this session containsimportant wisdom about
reclaiming those lost parts ofyourself.
All right, let's dive in.
Hey, ryan, it's a pleasure tosee you today.
Speaker 2 (01:05):
Oh, it's wonderful to be here.
Thanks, Brian.
Speaker 1 (01:07):
Yeah, so we spoke a little bit before this and I'm
just going to start right offand ask you what are we working
on?
What are we here for today?
Speaker 2 (01:13):
Yeah, I really appreciate this time.
This is something I've beenthinking about a lot and it's an
apparent conflict of interest,we'll say, between structure and
rigor, and improvisation andcreativity.
So specifically, the contextwould be in business, you know
(01:33):
and I'll probably use a lot ofmusic metaphors because a lot of
my experience with creativityhas been in music and it's there
.
There's there's a way thatstructure and improvisation work
out really well, and probablythe best example of that is
Charlie Parker.
And Charlie Parker, if peopledon't know, was possibly the
(01:55):
best saxophone player that everlived.
He invented bebop music and hehad what he would call
woodshedding, which meant thathe went to the woodshed to
practice every single song andevery single key over and over
and over and over and over again, and as a result of that he was
able to improvise like nobodybefore or since you know.
(02:18):
So for me there's this tensionhere between the rigor of wood
shedding and then the ultimateoutcome of creativity, which
involves release.
You know, the fastest way todestroy your improvisation,
saxophone or otherwise, is tryto wonder where the next note is
(02:40):
going to come from.
You just allow it to come.
Now, the one thing I'll kind ofadd to this story is the reason
Charlie Parker became BirdParker and went through this
kind of transformation was hewas in St Louis and he was a kid
probably, I think, 14 or 15,and got on the bandstand and
(03:01):
started soloing, and it was sobad the drummer took his cymbal
off of the cymbal stand andthrew it at him, and so he left
humiliated and, you know,dedicated himself that that
would never happen again, andcertainly it never did.
So that's what I'd like to talkabout.
You know what's this tensionbetween creativity and
(03:22):
improvisation, and rigor andstructure?
Largely, if you're thinkingabout productivity, time
blocking everything that goesinto running.
A business has to be veryregimented to make sure
everything stays clean, but then, as a creative person, an
entrepreneur, you have to allowopportunities for improvisation
to emerge.
Speaker 1 (03:41):
That all makes sense to me.
But from a business perspectiveand also just from a musical
perspective and listening to you, I hear you talk about the
tension at a high level I'mwondering can you spend a little
bit of time describing how youexperienced that tension that
(04:01):
you're describing?
Speaker 2 (04:03):
Yeah, you know it's interesting because there was an
article that got me thinkingabout this and it was a study
done about product hunt launchesand it was essentially on two
sides of the table.
One side was productivity appsand then the other side was
games like video games, iosgames, something like that, and
(04:24):
they did a venn diagram of the,the audiences and the people
that contribute to the campaign,and they were completely
separate, you know.
So there was the.
The spirit of the thing waskind of bashing productivity
culture and it made me look atit in a different way, because I
have had to train myself to bevery regimented largely, I think
(04:49):
, because I am a creative personand perhaps other entrepreneurs
can kind of relate to thatwhere it's like you get into
business as a creativeexpression and you end up in
spreadsheets and QuickBooks, youknow, and HR documents.
So you know, the tension to meis am I providing myself enough
room or with nothing, noscheduling, no agendas, just
(05:16):
literally the uncarved block?
And how should I be likeapproaching that if I am truly
looking at kind of a creativeendeavor?
Speaker 1 (05:24):
Hmm, just to make sure I'm understanding you, ryan
, are you saying that?
And how should I be likeapproaching that if I am truly
looking at kind of a creativeendeavor?
Just to make sure I'munderstanding you, ryan, are you
saying that there's some sensethat, like, maybe you're not
providing yourself enough ofthat open space, or is it that
not enough structure or maybesomewhere in between?
Speaker 2 (05:40):
I think so.
I think I'm looking at it aslike a massively undervalued use
of time.
The open space, the open space,yeah, I mean, and I I've been a
meditator for a long time, youknow, but I never take the
intention of my sitting practiceas a place for creativity.
Rather, creativity is a greatpersona that will come to me
(06:03):
when I'm sitting by.
Allow I allow that to go, justas anything else business or
anything else that comes through.
But even that, that issomething that's scheduled on my
calendar and it's veryregimented and rigorous.
So this is the kind of tension.
Is all of this productivitygains actually hindering the
(06:26):
company and everything else I'mtrying to do?
Is it in the way?
Is it a distraction?
Speaker 1 (06:31):
Yeah so.
So let's say, let's just playwith it for a second.
Let's say it was a distractionand you were to change this like
what would you actually wantthis thing to look like instead?
Speaker 2 (06:43):
That's the scary part .
I don't know.
Speaker 1 (06:46):
Cool, let's hang out there then I don't know.
Speaker 2 (06:50):
You know, how do you, how do you release the reins a
little bit?
You know, this could probablybe another place that I'm
challenged with, you know, isdelegating, trusting people,
allowing things to happen.
You know, as opposed to like, Idon't think I'm a micromanager
or I'm like overbearing in anysense, but definitely I'm
(07:12):
keeping all the everything closeto me.
You know what I mean.
Speaker 1 (07:15):
Okay.
So there's like a thing herearound control and there's some
sense that like I don't knowwhat I would do if I let go of a
little bit of that structureand control.
Speaker 2 (07:32):
I think so, I think so and I think it's it's.
I have a hunch that it's, uh,not serving me.
You know that there's somethinginteresting around the corner.
If I can get to it, you know,cool Is it cool.
Speaker 1 (07:40):
If we just explore that in real time, then you bet
that thing yeah, okay cool, yeah, okay cool.
So, um, my first question therewould be yeah, so let's say, um
, you were able to like turn thedial down, like, like, let's
pretend there's like some, uh,like a fader right music analogy
, so there's a fader on a mixerand now you're like, you're
(08:00):
turning the control down likeseveral decibels here.
Yeah, what would that feel like?
What would you have to feel inthat situation?
Speaker 2 (08:11):
You know, when I, when I do that, I ended up
feeling lonely and isolated andout of the loop and uninformed
and by myself.
You know, if I was like toreally get to the core of it,
like what the feeling in my bodyis, like a kind of an ache and
a hunger, you know, like, oh I,I don't know what's going on,
and it makes me feel separate,you know, and and that's not a
(08:35):
good feeling, sure you?
Speaker 1 (08:38):
know, is it all right if we hang out with that just
for a little bit right now?
Sure, okay, yeah.
So you described like thisloneliness, like where does
where do you experience that inthe body?
Speaker 2 (08:51):
I think kind of like um, let me see in, like the
stomach, and I feel that mystomach and a tightness up the
front of my esophagus, I think,is like a pulling in, like a
curling, a hunching feeling, youknow, like a constriction I
think, great, yeah, constrictioncurling kind of sounds like
(09:13):
it's moving up and down in this,in this area.
Speaker 1 (09:15):
Yeah for sure, yeah.
And it seems to have somethingto do with control as well, like
if, if you turn down thecontrol, then this, the valence
of this feeling, seems to bemore noticeable.
Speaker 2 (09:26):
Yeah, absolutely, you know.
I think the other thing withcontrol too is it served me well
.
I've had positive outcomes fromlike really being like, you
know, having my hands in all thepots, you know.
So there's kind of like ahistorical memory there where
it's like, hey, you, if you dothis, good things happen.
You know what I mean.
(09:46):
Yeah, so you have.
Speaker 1 (09:48):
You have two good reasons to keep the control to
keep it going.
Yeah, exactly like these likegreat outcomes and it also it
seems to also mean you don'tneed to feel that, that
constriction, that curling that.
You were describing lonelinessright.
Yeah, if you're still in touchwith that feeling of the
loneliness, I wonder um, let'ssay you were giving it voice.
(10:11):
It was trying to say somethingto you, ryan, like what would it
be saying?
Speaker 2 (10:17):
boy.
You know, I think the voice isvery paranoid.
You know, this is almost like akey marker that I noticed is
like if I'm going through it,then I'll have this feeling of
paranoia, like the whole world'sagainst you, everyone's
conspiring against you.
This, this would be the if itgets loud.
And then when I hear that, I'mlike oh, oh, oh, oh, okay, I
(10:39):
need to make some changes,because now I'm getting this
like paranoid sensation.
You know, the little, thelittle demon on the shoulder,
the angel angel on the shoulder,that demon it's.
It's very paranoid and scared,you know.
Speaker 1 (10:52):
Yeah, and it's scared .
It seems like part of the fearis that there's like the world's
against you.
There's this oppositional sortof energy to it.
Yeah.
Speaker 2 (11:04):
And I know it's a little bit melodramatic, you
know it's also probably veryself-centered to think that the
world might conspire against me.
You know, yeah, I get it, butnonetheless it's like, it's a
feeling, you know, it's afeeling of like, oh man, I need
to shift my dimension in someway So'm harmonizing with um the
(11:27):
universe and its patterns, so,as I'm not pushing against the
flow like, I need to like gowith it a little bit, you know
yeah, yeah.
Speaker 1 (11:36):
So this voice is like , ah, like, this is my words,
but it's like you better watchout.
Things are dangerous, peopleare against you, right, us
versus them, sort of energy,absolutely, and that your
reaction to that is, when younotice it, like, oh, I got to
shift something, I got to shiftsomething, do I have that?
Speaker 2 (11:58):
right so far, I think .
So I'm very averse to thatsensation.
You know, kind of what I, whatI've been taught over the years
is that, like the aversion isthe is like the fatal blow.
You know, it's like, of course,when great feelings emerge, you
embrace those and you kind ofrun with those, um, and you love
(12:19):
it.
But when you have a verse, youkind of want to run with it too,
because it allows it to come inand leave.
You know, as opposed to beinglike, oh my God, why am I such a
psycho?
You know, why am I so paranoid?
Like that, that question, likethe questioning the question,
you kind of create this deathspiral, you know.
Speaker 1 (12:40):
Yeah, you might be familiar with the idea of the
second arrow.
You familiar with this idea.
Yeah, the second arrow.
You familiar with this idea yeah, absolutely yeah, so you're
describing firing the secondarrow, um, but let's say we, we
move away from that for a momentand if we let's say we like
just we're moving closer then tothis, this paranoid voice.
Okay, so you got this paranoidvoice.
Let's say we're just getting alittle more curious about it and
(13:06):
and let me just pause it it'sshielding you from something,
protecting you from some feelingor some experience by and doing
that by saying like, oh, thethings are against you, like
people are against you.
You got to watch out.
Like what?
What is it trying to protectyou from?
Exactly what is it trying toprotect you?
Speaker 2 (13:24):
from exactly what is it trying to protect me from?
Um, I don't know.
Probably like hurt and betrayal.
You know it's that's the thingI think with.
With paranoia is like you, youmight just be paranoid, but the
world might be working againstyou too.
(13:44):
It could be, it could be real.
So you know, I think, if you'vebeen hurt before.
Absolutely yeah, and, andwithout a doubt you know all of
us the the the longer you liveon planet earth, the more you're
going to be hurt and betrayedby people you love, by friends
and family, by, by everybody.
It's just, it's guaranteed tohappen.
(14:04):
So you know, I think that youknow it's a one once bitten,
twice shy, and a lot of likekind of our, our, that little
demon on the shoulder.
Maybe it's an angel in disguise, in the sense that like hey,
it's like trying to protect youfrom like hey, this, this could
you could get hurt again.
You know, I think maybe the, the, the bravery which pulls you
(14:25):
out of it is like okay, maybebeing hurt is inevitable and
that's the right thing to do,cause I want to live in a
virtuous way, or something likethat.
You know what I mean.
So two ways to look at it, Iguess, but also nonetheless very
unpleasant and also probablydelusional.
It's like creating a potentialfuture that doesn't exist yet,
(14:48):
of course, but it's kind oflatching on to a potential
negative outcome, as opposed tothat outcome being one of many.
I think it's another form ofcontrol in some sense.
Absolutely.
Speaker 1 (14:59):
Yeah, yeah.
So how much then is that needfor control, a way to avoid the
feeling of that hurt?
A?
Speaker 2 (15:09):
hundred percent.
Yeah, that's what it is,definitely.
But you know, if paranoia is anangel in disguise as a demon,
the one way it doesn't work isit just destroys creativity,
like I don't know if I look atcreativity and like new ideas or
like something to come out ofnothing.
(15:32):
I don't know where it comesfrom, but I know that it does
not come from paranoia, sure,although I have seen some
journals of schizophrenics thatare pretty cool you know.
Speaker 1 (15:45):
So here's a question that what um might not make any
sense, but um what's the linkbetween the pain and the
creativity?
Probably a substantial one.
Speaker 2 (15:56):
You know, I I think I was gonna say all of the great
art, but I don't think that'strue.
But I think a lot of great artis derivative of pain, you know
sure yeah, so the greatest youknow, sad songs or or art and
movies, vin, vincent, van Gogh'sentire catalog.
(16:17):
There you go, yeah, yeah,absolutely.
I mean there's, yeah, there's,there's definitely a seed.
I mean it's, it's often, youknow, it's probably.
I mean the blues, right, it'slike, why does the cage bird
sing?
There's like so many analogiesof, like you know, art becoming
like a great channel for pain, Isuppose sure so.
Speaker 1 (16:40):
So, coming back to you, ryan, like you turn the
fader of control down a littlebit, so so that you can then
start to hear a little bit moreof the angel devil and then the
protection of that stuffunderneath.
What happens for you, then?
Speaker 2 (16:58):
what happens typically, or if I'm just
happens for you right now, inthe present moment if I turn it
down, um, I think it makes meuneasy, it makes me feel that
the future would is going intoan uncertain direction or have
(17:18):
less certainty, or at least theillusion of certainty, you know,
and potentially like givesopportunity for those voices to
start creeping in.
You know, there's like abusyness associated, I think,
sometimes with work.
That you're checking off allthese tasks is very satisfying,
you know, check off tasks, getstuff done, um, but also, like,
(17:41):
maybe to the point of thisconversation, is a lot of that
busyness really just there tokind of subdue some potential,
you know, voice that's creepingin?
Speaker 1 (17:50):
Yeah, in my experience, those voices tend
not to stop talking when we'recovering it over with the
checklist.
Speaker 2 (17:58):
Right, they're just quieter.
They're in the backgroundwaiting for you to wake up at 3
am.
Sure, then they get real loud.
Speaker 1 (18:06):
What are you hearing it say right now, if anything?
Speaker 2 (18:39):
Well, it's Monday, we're recording this Monday
morning, you know, and kind of,I always have this.
I have this gut check for memyself which is like, hey, man,
how does all this stuff's goingto come together?
Like that kind of feeling.
So I think I always bring thatinto a case of the Mondays, you
know.
So you know there's that, andthen there's just this other
feeling of like this greatopportunity.
I'm loving this conversationand being able to, like, have a
cool podcast with you.
It's really cool.
It fires me up, you know, makesme really excited, you know.
So for me, you know, and alsothere's this question that we're
(19:00):
talking about.
That's always kind of workingthis way around, you know, and
as we're talking about it, itseems like there is a link to,
like the pain perhaps, of likebetrayal and fear of being hurt,
and the creative component thatmight harmonize this thing, you
know, in some way.
And then perhaps it's like,maybe what it is is it's not in
(19:25):
the business arena, Maybe it's amaybe it's a blue song.
You know what I mean.
Maybe the problem isn't aconflict of productivity and
creative at work.
It's like no man.
Maybe you got some like somelike hurt in you that needs to
be, like you know, soothed alittle bit.
You know, maybe write a bluessong.
You know there's this.
(19:50):
I read this article once aboutthis emotion called leg it.
It was like it was.
It was considered to be a novelemotion and the emotion it was
found by this anthropologist, Ithink in the Philippines, where
it was like an indigenous tribe.
And what would happen is therewas different tribes that were,
(20:11):
you know, warring against eachother and let's say, like your
brother went to battle anddidn't come back, he got killed
by your ops.
Well, what would happen is thetribe would gather around that
night and they would startmoaning.
They start moaning like this,like guttural, you know, like
putting it out, and theneveryone in the tribe would like
, would start like mimicking it,and they would all be making
(20:34):
this moaning sound and theywould get, work themselves into
a frenzy and then be like boomand then go get their their
weapons and go set out and fight.
So the the emotion was kind ofdescribed as like this mourning
and this, like um murderous rage.
You know, and I was like that'sa heck of an emotion to like
(20:56):
find novelly.
You know it's not like it'svery subtle and sublime, you
know, but I always somethingabout that story resonated with
me, you know, and like it's likeyou can hear that in certain
music.
You know, mourning andmurderous rage, you know whether
it's like there's like ahaunting quality, maybe that's
(21:16):
the, the, the charlie parkerthing, maybe that's what rage
against the machine is tappinginto, maybe that's triads, minor
, minor triads, I don't know I?
Speaker 1 (21:25):
yeah, I totally get it.
What.
What made you think about that?
For your own self, right I?
Speaker 2 (21:29):
think the the ritual of it, the ritual of taking this
horrible thing that's happenedto you and and like
materializing it into the world.
You know, like it's this, it'sthis chorus, this moaning chorus
, that comes into the world asas being like a healing and
motivating, uh, exercise.
Yeah, you know so.
Yeah, I suppose that's what I'mthinking of is like, okay,
(21:51):
maybe there's like a ritual here, maybe there's some kind of
like creative ritual that youput in that, you know, allows
for some of the spontaneity andthings to happen to, to be a
ballast, I think, maybe for therigor or something.
Speaker 1 (22:07):
Yeah, I mean to reflect on that for a moment.
I think that's exactly rightthat you're describing there's a
container, there is some, someset of steps that are predefined
, but it's really just acontainer for the human
expression to then expand intothat and who knows what that
will actually end up lookinglike.
Right, there's a spontaneity toit and there's the expression
(22:29):
to it, and I wonder what doesthat look like for you?
Ryan, you started thisconversation talking about the
balance or the tension betweenstructure, productivity, control
, and creativity and expression.
But if we were to say, actually, these two things are not at
odds, they can actually workwell together.
What does that look like here?
Speaker 2 (22:49):
Yeah, man, maybe I'm just trying to talk myself into
making a record, you know.
Speaker 1 (22:57):
Have you ever done that?
Speaker 2 (22:58):
Yeah, yeah, former life I was a touring musician.
You know.
I made three records and didmixtapes and used to play all
the time, you know, and at onepoint I was like no more music,
it's done, and that was it what,what was happening, that made
you say that?
And that was it.
What was happening that madeyou say that?
You know I was playing a showand it didn't go the way I
(23:19):
wanted to.
They stiffed me on payment forprobably the 12th time.
I mean, the music industry ismore corrupt than the boxing
industry and the boxing industryis the most corrupt business in
the world.
So I had two young children atthe time and was working on two
bands and doing a bunch of stuffand just was exhausted, I think
(23:41):
, and that kind of was the.
That was the thing that reallyjust ended the music career.
But even more than that, I knewthat I couldn't.
I couldn't just dabble withmusic.
I was so it is so important tome, it was my entire world, you
know my profession, everythingthat I couldn't.
I couldn't just dabble withmusic.
I was so it is so important tome, it was my entire world.
You know my profession,everything that I couldn't just
like do it halfway, I had tolike kill it.
(24:02):
I have to be like no more, youknow, and all or nothing, all or
nothing, yep, and it's likeNope, no more music, not working
in this business anymore, I'mnot making music, it's all over,
it's done behind me and move on.
Now, that's not, it's not thatdramatic.
You know, still, I play songshere and there and there's
guitars kicking around my, myhouse, all over the place, but
(24:23):
there was definitely like a wallthat came down and was like no,
you know, what I mean and thisis probably the tension I'm
discovering is that it does seemto be a wall.
For me is like all in creativeor all in with you know the, the
rational, um, you know uh,rigor based kind of uh lifestyle
(24:44):
, I suppose right, right control, scheduling, left, brain, sort
of yeah left brain, right brain,and there's, just like you know
, a bulletproof wall in betweenthem.
Speaker 1 (24:56):
Yeah, yeah yeah, I'm, I'm, I'm visualizing that wall
like if it's, if it starts tocome down a little bit or go,
however you want to visualize it.
But like that, let's say likethe it's, it's, it's less
impermeable, right, right Nowthere's some actual room to
breathe between both worlds.
(25:18):
Let's call it.
What does that produce for Ryanhere?
Speaker 2 (25:23):
If it's permeable.
Speaker 1 (25:25):
Yeah, less of this, all or nothing.
Speaker 2 (25:28):
But it just makes me happier.
You know, I think it's probablypretty clear.
You know it's interesting.
You know, I think it's it'sprobably pretty clear, you know
it's interesting.
But again, like when I when Idid that, you know, like I
stopped listening to music andjust went all in on podcasts and
then, as a result, developed awhole career around podcasting,
(25:49):
you know.
So it's like, okay, well, yeah,that was either.
The rational side of me is like,yeah, man, that's that's
working for you, that's good,you know.
But I think it's just like, forwhatever reason I'm this, I
have this like black or whitetendency in here.
But there's all this gray grayarea, you know, and it's funny
that, like you know, this wouldkind of creep in professionally
(26:10):
first, but like no-transcript,and I think there was like, you
(26:45):
know, you get so busy and I, youknow, my kids now are in high
school, and so it's just onething after the other, the other
, the other.
There is no relenting, you know, and I'm so blessed and lucky
that, like, I have a successfulbusiness and I have a beautiful
family that loves me and isgreat, but the the like speed
and pace is like it's intense,and I think I felt like I was
(27:07):
like losing a little bit of likewhat I like to do, like I've
kind of forgot who.
I have so many responsibilities.
It's like, well, what do I?
I have so many responsibilities.
It's like, well, what do Ienjoy doing?
And there wasn't like a clearanswer until I was like sitting
in the woods and was like, oh no, you love green chili and tacos
, you know for sure, but youalso really like music, you know
(27:27):
, and it felt really good justto think about these things that
I like to do, you know yeah, solike when you were like in the
woods, like just in nature, itsounds like you were slowing
down and then you were able toreconnect with these just simple
things, uh, that that reallyyou enjoy, that that feel really
good to you and your system.
Speaker 1 (27:49):
Um, and I I don't know about you, but when I
listen to you that that soundslike the opposite of rigid
control.
It sounds like there was moreof this sort of openness for you
.
Does that track?
Speaker 2 (28:05):
Yeah, I think so, but you see, I still start making
lists and action items.
Speaker 1 (28:12):
You got to start somewhere.
Speaker 2 (28:13):
Yeah, sure, I know.
Yeah, no, but that was was itand it was actually comforting,
you know, it was like okay, yeah, you still like things, there's
still things you like there's.
Just there was been a lot ofthings that I've been doing that
I'm just questioning like Idon't think I like this, yeah
okay, yeah, it's amazing whenyou just say it out loud yeah, I
(28:33):
know sitting on snowboardingand I'm like I love, love
hanging out with my kids, but Idon't think I like snowboarding
anymore.
I don't think I do and it's likesomething I'd love forever, but
I was like I actually I hatethis.
I'm not doing this anymore,okay.
Speaker 1 (28:50):
Okay, Okay, cool.
So let's say you keep followingthat.
You just give yourselfpermission to name what you're I
don't like this, I do like thatand then you orient yourself
around that.
What happens then?
Speaker 2 (29:07):
I don't know.
I think I'm happier.
I don't know.
I also feel weird saying thisout of my mouth.
Does it seem strange that youforget what you like and what
you don't like?
Is that odd?
Speaker 1 (29:18):
I think it's actually incredibly common, do you
really?
Speaker 2 (29:21):
Yeah, yeah, that's good, that's good.
So, yeah, I don't know, I thinkthat's you know.
I don't know, maybe that's howyou just go with the flow.
It's like you just pick up acouple branches alongside, if
you like branches to mixmetaphors all over the place
here.
Yeah, you know.
Speaker 1 (29:41):
Yeah Well, just to reflect a bit from what I'm
picking up from you, ryan, partof what I hear is that you
actually are really, really goodat following your interests,
your desires, the things thatyou enjoy, and also you've
encountered a lot of thingsalong the way that resulted in
(30:04):
hurt, burnout, intensity.
You know, that has its way ofsweeping somebody up as well,
and there's like a way in whichwe can lose ourselves in that.
Um, maybe there's some sense ofobligation, uh, that comes in,
uh, to play uh along the way aswell.
I'm just maybe speculating alittle bit based off of what you
(30:25):
said.
And so to your question like isit, is it normal, like, do
people do this where, like theysort, there's a way in which
many of us can lose touch withthat right?
They lose touch with, withwhat's authentic to them because
they replace that with what'sexpected of them, what they're
(30:46):
supposed to do, externalobligation, that sort of thing.
So that doesn't seem strange tome at all.
I I guess, as I'm saying it,I'm curious, like, how's that
landing?
As I reflected back to you.
Speaker 2 (31:06):
Yeah, I think that's it, you know, and I think too
that I've I've led such a funand creative career, like the
way I've, you know, earned aliving over the years is just
like.
It's so fun, you know, and it'slike, and I have a lot of
passion and and a lot ofenthusiasm when I'm going
towards something, and I thinkpart of that is like making sure
that what I'm going towards isvery clear.
(31:26):
And when it's not and I thinktoo, like, the more complicated
your lives get and you know, themore you add families and
businesses and stuff, itdefinitely gets complex that you
kind of lose track of, like,where you're headed, and so it's
hard to sustain the amount ofenthusiasm.
Or rather, maybe the enthusiasmyou know kind of morphs into
(31:48):
something else, cause I'vealways felt like I've got extra
energy.
You know I've got extra energyI've got to burn off, usually
through, you know, physicalactivities, but also through,
like, my pursuits.
And if I have extra energy andit's channeled as enthusiasm for
the mission of where I'm going,you know it's perfect.
(32:08):
But like, if the mission startsto get hazy, because life is
complicated and there's a lot ofdifferent things, you're
balancing the enthusiasm, theextra energy changes its tone.
Speaker 1 (32:20):
Yeah, what do you think?
What do you think is in the wayof having the clarity of
mission?
Speaker 2 (32:28):
What is in the way, boy, I don't know.
I think kind of what you weretalking about.
You know obligation.
You know as like.
You know obligation.
You know as like you know again, I think you know if you want
to be a responsible, productiveperson, then you pick up as much
(32:52):
responsibility and obligationas you possibly can, hold as
much as you can carry, carry asstrong as your back is, take
every ounce on because, honestly, I think that you got an
obligation to the world, likethe you.
You owe the world your best.
You know um, but you know it's,it's tiring, you know, and
(33:15):
maybe it's counterproductive toyou know the, the, the artist in
me that just wants to be flyand be free.
You know.
Speaker 1 (33:24):
Yeah, so it's like you contain these multiple,
multiple selves here, Like the,the, the part of you that's give
the world it's the best and Iowe it to the world.
And then there's just thisartist also in you that's that's
needing some more space fromwhat I hear to the world.
And then there's just thisartist also in you that's
needing some more space fromwhat I hear?
Speaker 2 (33:42):
Yeah, totally, and for some reason there's a wall
between them.
I have a hard time opening thetwo and letting them chill
together.
Opening the door, it's likeeither I'm totally free and I
tasted that you know and I Itasted that you know so, or it's
(34:04):
like, nope, you're taking on asmuch responsibility as you
possibly can, because the worldneeds responsible men.
Speaker 1 (34:09):
Huh, yeah, cool, okay .
So so let's, let's pretend, ifyou're game for this, like,
let's pretend the two of themare seated together at a table
and and you're facilitating somedialogue between them.
I know it seems like they mightnot see eye to eye here, but
what is it that the artistdoesn't understand about the guy
(34:34):
who's operating fromresponsibility that would be
important for him to know?
The guy who's operating fromresponsibility, that that that
would be important for him toknow.
Speaker 2 (34:40):
You know, my first instinct is they'd be critical
of each other first and thenthey'd be encouraging in some
manner.
You know, um, and it's probablylike why I love podcasting and
why I love conversation ingenerals, because you'll meet
each other in the middle.
Yeah, you know, eventuallyyou're going to be like hey man,
(35:00):
actually we got a lot more incommon than we thought you know,
yeah, so they worked throughsome of that stuff to get to
some common understanding here.
I think they would immediately,but there's just no dialogue
there.
I think I mean, maybe for thesake of hyperbole and somehow
bifurcating my personality intothese two distinct entities,
(35:22):
it's helpful to look at them aslike they're not talking to each
other.
You know what I mean?
Yeah, they're probablycompletely reliant on each other
, for sure, but they're notwilling to admit dependency
because they want supremacy.
Speaker 1 (35:40):
Okay, Well, you were just a minute ago.
You were sort of referring to aworld where they're getting
along here, so like it soundslike you're imagining some
scenario where they are actuallyin dialogue, 100%.
Yeah, how do you get there?
How do they get there?
Speaker 2 (36:00):
The more I think about it, the more I think I
just need to write some songs,you know like, actually just do
it, you know, use the rigor partof my brain to, you know time
block a weekend and just gowrite some songs and hang out
with myself.
You know, I think thatultimately might be, might be
just it myself.
Speaker 1 (36:19):
You know, I think that ultimately might be, might
be just it, you know yeah, seemsto link back to what we were
touching on earlier, just likethe what was that?
That novel emotion you'redescribing like, okay, we're
gonna, we're gonna enter intothe ritual, but then we're gonna
fill the space with, with ourexpression yeah, yeah, I think
that I think that's probablyprobably it, and then let things
(36:41):
fall where they may.
Speaker 2 (36:42):
You know, it's just, it's just funny to say this
stuff and realize that, likeit's like I all, I want this all
to like have merit, Like it'slike I'll do it if I feel like
I'm going to get something outof it.
You know what I mean.
Speaker 1 (36:56):
Let me ask you this, so what?
Okay, let's play with that.
So when this tribe or thisgroup of people are out there in
mourning, are they doing itbecause they need to get
something out of it?
Speaker 2 (37:10):
No, I think they're just channeling something that
exists.
I think they just hit thatfrequency and they're just in
that.
I don't think they're trying tobe productive with it at all.
You know, I think, yeah, I mean, I, I put up when I kind of
went no music and was like, okay, I'm being very selective with
(37:34):
my time because I only have somuch of it and I have people
that are counting on me, youknow, because I only have so
much of it and I have peoplethat are counting on me.
You know.
So what I, what I did, is I saidI'm not doing anything that
isn't of service, fun and makesmoney.
It has to make money for me todo it, otherwise I am, I, I'm
(37:56):
letting people down, you know.
So this, this, which workedgreat, you know, it was like boy
that really kept me on astraight and narrow, because
otherwise I would just, I would,I would be in my closet writing
love songs forever, I justwould, you know, and it's like
you gotta, you gotta dosomething else, buddy.
So the, the, the, theparameters really worked well,
but I think the, I think theremight be, I think there's a cost
(38:19):
, you know, and maybe the costisn't worth it To some point.
You know, it's like that was 15years ago maybe yeah, about 15
years ago that I really madethose kind of like very rigid
rules for myself, and it's likeyou know, maybe you relax.
Speaker 1 (38:38):
Yeah, it was 15 years ago.
It's, that's not now.
How much is that needed now?
Yeah, is the question yeah, howmuch you know yeah I'm I'm
really looking forward tohearing the music that you put
out from here did you start withmurderous rage moaning?
Speaker 2 (39:00):
oh yeah, that would be a great hell.
Yeah, it's so funny, nice.
Yeah, yeah, man, I think Icould do that.
I could do that.
Speaker 1 (39:14):
I love it I I this feels like a pretty good spot.
I don't know about you like,how are you feeling just coming?
I, I'm just tuning into whereyou are now.
Speaker 2 (39:24):
It feels good.
You know, this is reallyunexpected kind of conversation.
I'm not sure to do most of theyour, your episodes go like this
.
Speaker 1 (39:32):
I got to say this is probably one of the more unique
ones we've done.
Speaker 2 (39:38):
Yeah, I don't know, it felt really good.
I appreciate it.
Like sometimes you gotta like.
You know, I got a palette ofall these thoughts and emotion
going through me and putting itout like this like makes it seem
pretty clear like there doesn'tnecessarily need to be a
tension between this and that.
Speaker 1 (39:53):
You know, yeah, so well, let me, let me ask you
this, ryan, as we start to closeout.
Then, um, yeah, just tuninginto where you are now, and then
you look, look to how westarted this, this conversation.
Um, what do you want tohighlight?
What do you want to, uh, reallyunderscore coming out from the
(40:13):
session?
Speaker 2 (40:15):
I want to highlight how much I appreciate what you
do.
This has been awesome.
I think it's gotta be veryfulfilling and satisfying, you
know, talking, talking throughpeople and their, their weird
angels and demons on theshoulder, you know, so that's
really cool.
I don't have the opportunity todo a lot of conversations like
this, so I really appreciate it.
I think it's also justinteresting that it like
(40:40):
actually did bring up a lot ofemotion in me, like this is
something that like needsattention, you know, and and
busyness.
As much as I love work, it'snot gonna.
It's not gonna do it, it needs,I need something else.
I can tell if this is what's onthe tip of my tongue right now,
Monday morning or Mondayafternoon you know it's like all
right, like this is probablydeserve some attention, so I'm
(41:01):
going to pay heed to that.
Speaker 1 (41:03):
Awesome.
Well, I am really, reallylooking forward to hearing the
output, and you know, I love howyou started this conversation,
talking about Charlie Parker,and now I want to know what Ryan
Estes comes up with.
I'll be the first Spotifysubscriber, nice, all right, man
, I'll let you know, subscriberNice.
Speaker 2 (41:19):
All right, man, I'll let you know.
Speaker 1 (41:21):
Yeah, awesome, well, ryan, thank you so much for
coming on.
Appreciate it.
Brian, thank you so much.
The walls we build to protectourselves often become the very
barriers that block our growth.
Ryan's session illustrates howmany founders construct rigid
systems, not just forproductivity, but as shields
against vulnerability.
I've witnessed this patternrepeatedly in my coaching
practice.
What presents as productivitychallenges frequently masks a
(41:44):
deeper disconnection fromauthentic joy.
For Ryan, his musicalcreativity has been deliberately
walled off for years in serviceof responsibility and
obligation.
Now, two elements stood out tome from this session.
First, our protectivemechanisms develop for good
reason, but they often outlivetheir usefulness.
Stood out to me from thissession.
First, our protectivemechanisms develop for good
reason, but they often outlivetheir usefulness.
Secondly, reconnection doesn'trequire abandoning structure.
(42:06):
It's not black or white.
We may just need more permeableboundaries between different
aspects of ourselves.
So here's the question worthconsidering what parts of
yourself have you shut down inthe name of success?
The path forward isn't aboutperfect balance, but recognizing
when the walls we'veconstructed have become too
rigid.
Sometimes growth comes not whenwe push harder, but when we
(42:27):
loosen the grip of control justenough to let our authenticity
emerge again.
So I invite you to considerwhat that might look like in
your own leadership journey.
All right, that's anotherepisode of Slate On To Speed Up.
Thank you for listening.
If you enjoyed this episode,please remember to give it a
like, subscribe and a positivereview in your podcast app.
See you at the next one.
Welcome to Slow Down and Speed Up, where we have real
one-time coaching sessions withstartup founders working
through the challenges ofleadership.
I'm your host and executivecoach, brian Wang.
Today we're joined by RyanEstes, a founder who once toured
as a musician but now runs hislife on tight schedules and
spreadsheets.
He comes to the session askingthe question how do I balance
structure and creativity betweenthe artist and the operator?
(00:22):
As we explore this tension, wetouch on something that's a bit
non-obvious the productivitymechanisms that help us succeed
can also end up cutting us offfrom joy.
For Ryan, this manifests aswalls built between his
responsible business self andhis creative musical identity.
Many founders experience thiscompartmentalization without
realizing it sacrificing passionfor productivity, creative
(00:45):
expression for control.
If you've ever feltdisconnected from what
originally inspired you or sensesomething vital has been
missing from your leadershipjourney, despite outward success
, this session containsimportant wisdom about
reclaiming those lost parts ofyourself.
All right, let's dive in.
Hey, ryan, it's a pleasure tosee you today.
Speaker 2 (01:05):
Oh, it's wonderful to be here.
Thanks, Brian.
Speaker 1 (01:07):
Yeah, so we spoke a little bit before this and I'm
just going to start right offand ask you what are we working
on?
What are we here for today?
Speaker 2 (01:13):
Yeah, I really appreciate this time.
This is something I've beenthinking about a lot and it's an
apparent conflict of interest,we'll say, between structure and
rigor, and improvisation andcreativity.
So specifically, the contextwould be in business, you know
(01:33):
and I'll probably use a lot ofmusic metaphors because a lot of
my experience with creativityhas been in music and it's there
.
There's there's a way thatstructure and improvisation work
out really well, and probablythe best example of that is
Charlie Parker.
And Charlie Parker, if peopledon't know, was possibly the
(01:55):
best saxophone player that everlived.
He invented bebop music and hehad what he would call
woodshedding, which meant thathe went to the woodshed to
practice every single song andevery single key over and over
and over and over and over again, and as a result of that he was
able to improvise like nobodybefore or since you know.
(02:18):
So for me there's this tensionhere between the rigor of wood
shedding and then the ultimateoutcome of creativity, which
involves release.
You know, the fastest way todestroy your improvisation,
saxophone or otherwise, is tryto wonder where the next note is
(02:40):
going to come from.
You just allow it to come.
Now, the one thing I'll kind ofadd to this story is the reason
Charlie Parker became BirdParker and went through this
kind of transformation was hewas in St Louis and he was a kid
probably, I think, 14 or 15,and got on the bandstand and
(03:01):
started soloing, and it was sobad the drummer took his cymbal
off of the cymbal stand andthrew it at him, and so he left
humiliated and, you know,dedicated himself that that
would never happen again, andcertainly it never did.
So that's what I'd like to talkabout.
You know what's this tensionbetween creativity and
(03:22):
improvisation, and rigor andstructure?
Largely, if you're thinkingabout productivity, time
blocking everything that goesinto running.
A business has to be veryregimented to make sure
everything stays clean, but then, as a creative person, an
entrepreneur, you have to allowopportunities for improvisation
to emerge.
Speaker 1 (03:41):
That all makes sense to me.
But from a business perspectiveand also just from a musical
perspective and listening to you, I hear you talk about the
tension at a high level I'mwondering can you spend a little
bit of time describing how youexperienced that tension that
(04:01):
you're describing?
Speaker 2 (04:03):
Yeah, you know it's interesting because there was an
article that got me thinkingabout this and it was a study
done about product hunt launchesand it was essentially on two
sides of the table.
One side was productivity appsand then the other side was
games like video games, iosgames, something like that, and
(04:24):
they did a venn diagram of the,the audiences and the people
that contribute to the campaign,and they were completely
separate, you know.
So there was the.
The spirit of the thing waskind of bashing productivity
culture and it made me look atit in a different way, because I
have had to train myself to bevery regimented largely, I think
(04:49):
, because I am a creative personand perhaps other entrepreneurs
can kind of relate to thatwhere it's like you get into
business as a creativeexpression and you end up in
spreadsheets and QuickBooks, youknow, and HR documents.
So you know, the tension to meis am I providing myself enough
room or with nothing, noscheduling, no agendas, just
(05:16):
literally the uncarved block?
And how should I be likeapproaching that if I am truly
looking at kind of a creativeendeavor?
Speaker 1 (05:24):
Hmm, just to make sure I'm understanding you, ryan
, are you saying that?
And how should I be likeapproaching that if I am truly
looking at kind of a creativeendeavor?
Just to make sure I'munderstanding you, ryan, are you
saying that there's some sensethat, like, maybe you're not
providing yourself enough ofthat open space, or is it that
not enough structure or maybesomewhere in between?
Speaker 2 (05:40):
I think so.
I think I'm looking at it aslike a massively undervalued use
of time.
The open space, the open space,yeah, I mean, and I I've been a
meditator for a long time, youknow, but I never take the
intention of my sitting practiceas a place for creativity.
Rather, creativity is a greatpersona that will come to me
(06:03):
when I'm sitting by.
Allow I allow that to go, justas anything else business or
anything else that comes through.
But even that, that issomething that's scheduled on my
calendar and it's veryregimented and rigorous.
So this is the kind of tension.
Is all of this productivitygains actually hindering the
(06:26):
company and everything else I'mtrying to do?
Is it in the way?
Is it a distraction?
Speaker 1 (06:31):
Yeah so.
So let's say, let's just playwith it for a second.
Let's say it was a distractionand you were to change this like
what would you actually wantthis thing to look like instead?
Speaker 2 (06:43):
That's the scary part .
I don't know.
Speaker 1 (06:46):
Cool, let's hang out there then I don't know.
Speaker 2 (06:50):
You know, how do you, how do you release the reins a
little bit?
You know, this could probablybe another place that I'm
challenged with, you know, isdelegating, trusting people,
allowing things to happen.
You know, as opposed to like, Idon't think I'm a micromanager
or I'm like overbearing in anysense, but definitely I'm
(07:12):
keeping all the everything closeto me.
You know what I mean.
Speaker 1 (07:15):
Okay.
So there's like a thing herearound control and there's some
sense that like I don't knowwhat I would do if I let go of a
little bit of that structureand control.
Speaker 2 (07:32):
I think so, I think so and I think it's it's.
I have a hunch that it's, uh,not serving me.
You know that there's somethinginteresting around the corner.
If I can get to it, you know,cool Is it cool.
Speaker 1 (07:40):
If we just explore that in real time, then you bet
that thing yeah, okay cool, yeah, okay cool.
So, um, my first question therewould be yeah, so let's say, um
, you were able to like turn thedial down, like, like, let's
pretend there's like some, uh,like a fader right music analogy
, so there's a fader on a mixerand now you're like, you're
(08:00):
turning the control down likeseveral decibels here.
Yeah, what would that feel like?
What would you have to feel inthat situation?
Speaker 2 (08:11):
You know, when I, when I do that, I ended up
feeling lonely and isolated andout of the loop and uninformed
and by myself.
You know, if I was like toreally get to the core of it,
like what the feeling in my bodyis, like a kind of an ache and
a hunger, you know, like, oh I,I don't know what's going on,
and it makes me feel separate,you know, and and that's not a
(08:35):
good feeling, sure you?
Speaker 1 (08:38):
know, is it all right if we hang out with that just
for a little bit right now?
Sure, okay, yeah.
So you described like thisloneliness, like where does
where do you experience that inthe body?
Speaker 2 (08:51):
I think kind of like um, let me see in, like the
stomach, and I feel that mystomach and a tightness up the
front of my esophagus, I think,is like a pulling in, like a
curling, a hunching feeling, youknow, like a constriction I
think, great, yeah, constrictioncurling kind of sounds like
(09:13):
it's moving up and down in this,in this area.
Speaker 1 (09:15):
Yeah for sure, yeah.
And it seems to have somethingto do with control as well, like
if, if you turn down thecontrol, then this, the valence
of this feeling, seems to bemore noticeable.
Speaker 2 (09:26):
Yeah, absolutely, you know.
I think the other thing withcontrol too is it served me well
.
I've had positive outcomes fromlike really being like, you
know, having my hands in all thepots, you know.
So there's kind of like ahistorical memory there where
it's like, hey, you, if you dothis, good things happen.
You know what I mean.
(09:46):
Yeah, so you have.
Speaker 1 (09:48):
You have two good reasons to keep the control to
keep it going.
Yeah, exactly like these likegreat outcomes and it also it
seems to also mean you don'tneed to feel that, that
constriction, that curling that.
You were describing lonelinessright.
Yeah, if you're still in touchwith that feeling of the
loneliness, I wonder um, let'ssay you were giving it voice.
(10:11):
It was trying to say somethingto you, ryan, like what would it
be saying?
Speaker 2 (10:17):
boy.
You know, I think the voice isvery paranoid.
You know, this is almost like akey marker that I noticed is
like if I'm going through it,then I'll have this feeling of
paranoia, like the whole world'sagainst you, everyone's
conspiring against you.
This, this would be the if itgets loud.
And then when I hear that, I'mlike oh, oh, oh, oh, okay, I
(10:39):
need to make some changes,because now I'm getting this
like paranoid sensation.
You know, the little, thelittle demon on the shoulder,
the angel angel on the shoulder,that demon it's.
It's very paranoid and scared,you know.
Speaker 1 (10:52):
Yeah, and it's scared .
It seems like part of the fearis that there's like the world's
against you.
There's this oppositional sortof energy to it.
Yeah.
Speaker 2 (11:04):
And I know it's a little bit melodramatic, you
know it's also probably veryself-centered to think that the
world might conspire against me.
You know, yeah, I get it, butnonetheless it's like, it's a
feeling, you know, it's afeeling of like, oh man, I need
to shift my dimension in someway So'm harmonizing with um the
(11:27):
universe and its patterns, so,as I'm not pushing against the
flow like, I need to like gowith it a little bit, you know
yeah, yeah.
Speaker 1 (11:36):
So this voice is like , ah, like, this is my words,
but it's like you better watchout.
Things are dangerous, peopleare against you, right, us
versus them, sort of energy,absolutely, and that your
reaction to that is, when younotice it, like, oh, I got to
shift something, I got to shiftsomething, do I have that?
Speaker 2 (11:58):
right so far, I think .
So I'm very averse to thatsensation.
You know, kind of what I, whatI've been taught over the years
is that, like the aversion isthe is like the fatal blow.
You know, it's like, of course,when great feelings emerge, you
embrace those and you kind ofrun with those, um, and you love
(12:19):
it.
But when you have a verse, youkind of want to run with it too,
because it allows it to come inand leave.
You know, as opposed to beinglike, oh my God, why am I such a
psycho?
You know, why am I so paranoid?
Like that, that question, likethe questioning the question,
you kind of create this deathspiral, you know.
Speaker 1 (12:40):
Yeah, you might be familiar with the idea of the
second arrow.
You familiar with this idea.
Yeah, the second arrow.
You familiar with this idea yeah, absolutely yeah, so you're
describing firing the secondarrow, um, but let's say we, we
move away from that for a momentand if we let's say we like
just we're moving closer then tothis, this paranoid voice.
Okay, so you got this paranoidvoice.
Let's say we're just getting alittle more curious about it and
(13:06):
and let me just pause it it'sshielding you from something,
protecting you from some feelingor some experience by and doing
that by saying like, oh, thethings are against you, like
people are against you.
You got to watch out.
Like what?
What is it trying to protectyou from?
Exactly what is it trying toprotect you?
Speaker 2 (13:24):
from exactly what is it trying to protect me from?
Um, I don't know.
Probably like hurt and betrayal.
You know it's that's the thingI think with.
With paranoia is like you, youmight just be paranoid, but the
world might be working againstyou too.
(13:44):
It could be, it could be real.
So you know, I think, if you'vebeen hurt before.
Absolutely yeah, and, andwithout a doubt you know all of
us the the the longer you liveon planet earth, the more you're
going to be hurt and betrayedby people you love, by friends
and family, by, by everybody.
It's just, it's guaranteed tohappen.
(14:04):
So you know, I think that youknow it's a one once bitten,
twice shy, and a lot of likekind of our, our, that little
demon on the shoulder.
Maybe it's an angel in disguise, in the sense that like hey,
it's like trying to protect youfrom like hey, this, this could
you could get hurt again.
You know, I think maybe the, the, the bravery which pulls you
(14:25):
out of it is like okay, maybebeing hurt is inevitable and
that's the right thing to do,cause I want to live in a
virtuous way, or something likethat.
You know what I mean.
So two ways to look at it, Iguess, but also nonetheless very
unpleasant and also probablydelusional.
It's like creating a potentialfuture that doesn't exist yet,
(14:48):
of course, but it's kind oflatching on to a potential
negative outcome, as opposed tothat outcome being one of many.
I think it's another form ofcontrol in some sense.
Absolutely.
Speaker 1 (14:59):
Yeah, yeah.
So how much then is that needfor control, a way to avoid the
feeling of that hurt?
A?
Speaker 2 (15:09):
hundred percent.
Yeah, that's what it is,definitely.
But you know, if paranoia is anangel in disguise as a demon,
the one way it doesn't work isit just destroys creativity,
like I don't know if I look atcreativity and like new ideas or
like something to come out ofnothing.
(15:32):
I don't know where it comesfrom, but I know that it does
not come from paranoia, sure,although I have seen some
journals of schizophrenics thatare pretty cool you know.
Speaker 1 (15:45):
So here's a question that what um might not make any
sense, but um what's the linkbetween the pain and the
creativity?
Probably a substantial one.
Speaker 2 (15:56):
You know, I I think I was gonna say all of the great
art, but I don't think that'strue.
But I think a lot of great artis derivative of pain, you know
sure yeah, so the greatest youknow, sad songs or or art and
movies, vin, vincent, van Gogh'sentire catalog.
(16:17):
There you go, yeah, yeah,absolutely.
I mean there's, yeah, there's,there's definitely a seed.
I mean it's, it's often, youknow, it's probably.
I mean the blues, right, it'slike, why does the cage bird
sing?
There's like so many analogiesof, like you know, art becoming
like a great channel for pain, Isuppose sure so.
Speaker 1 (16:40):
So, coming back to you, ryan, like you turn the
fader of control down a littlebit, so so that you can then
start to hear a little bit moreof the angel devil and then the
protection of that stuffunderneath.
What happens for you, then?
Speaker 2 (16:58):
what happens typically, or if I'm just
happens for you right now, inthe present moment if I turn it
down, um, I think it makes meuneasy, it makes me feel that
the future would is going intoan uncertain direction or have
(17:18):
less certainty, or at least theillusion of certainty, you know,
and potentially like givesopportunity for those voices to
start creeping in.
You know, there's like abusyness associated, I think,
sometimes with work.
That you're checking off allthese tasks is very satisfying,
you know, check off tasks, getstuff done, um, but also, like,
(17:41):
maybe to the point of thisconversation, is a lot of that
busyness really just there tokind of subdue some potential,
you know, voice that's creepingin?
Speaker 1 (17:50):
Yeah, in my experience, those voices tend
not to stop talking when we'recovering it over with the
checklist.
Speaker 2 (17:58):
Right, they're just quieter.
They're in the backgroundwaiting for you to wake up at 3
am.
Sure, then they get real loud.
Speaker 1 (18:06):
What are you hearing it say right now, if anything?
Speaker 2 (18:39):
Well, it's Monday, we're recording this Monday
morning, you know, and kind of,I always have this.
I have this gut check for memyself which is like, hey, man,
how does all this stuff's goingto come together?
Like that kind of feeling.
So I think I always bring thatinto a case of the Mondays, you
know.
So you know there's that, andthen there's just this other
feeling of like this greatopportunity.
I'm loving this conversationand being able to, like, have a
cool podcast with you.
It's really cool.
It fires me up, you know, makesme really excited, you know.
So for me, you know, and alsothere's this question that we're
(19:00):
talking about.
That's always kind of workingthis way around, you know, and
as we're talking about it, itseems like there is a link to,
like the pain perhaps, of likebetrayal and fear of being hurt,
and the creative component thatmight harmonize this thing, you
know, in some way.
And then perhaps it's like,maybe what it is is it's not in
(19:25):
the business arena, Maybe it's amaybe it's a blue song.
You know what I mean.
Maybe the problem isn't aconflict of productivity and
creative at work.
It's like no man.
Maybe you got some like somelike hurt in you that needs to
be, like you know, soothed alittle bit.
You know, maybe write a bluessong.
You know there's this.
(19:50):
I read this article once aboutthis emotion called leg it.
It was like it was.
It was considered to be a novelemotion and the emotion it was
found by this anthropologist, Ithink in the Philippines, where
it was like an indigenous tribe.
And what would happen is therewas different tribes that were,
(20:11):
you know, warring against eachother and let's say, like your
brother went to battle anddidn't come back, he got killed
by your ops.
Well, what would happen is thetribe would gather around that
night and they would startmoaning.
They start moaning like this,like guttural, you know, like
putting it out, and theneveryone in the tribe would like
, would start like mimicking it,and they would all be making
(20:34):
this moaning sound and theywould get, work themselves into
a frenzy and then be like boomand then go get their their
weapons and go set out and fight.
So the the emotion was kind ofdescribed as like this mourning
and this, like um murderous rage.
You know, and I was like that'sa heck of an emotion to like
(20:56):
find novelly.
You know it's not like it'svery subtle and sublime, you
know, but I always somethingabout that story resonated with
me, you know, and like it's likeyou can hear that in certain
music.
You know, mourning andmurderous rage, you know whether
it's like there's like ahaunting quality, maybe that's
(21:16):
the, the, the charlie parkerthing, maybe that's what rage
against the machine is tappinginto, maybe that's triads, minor
, minor triads, I don't know I?
Speaker 1 (21:25):
yeah, I totally get it.
What.
What made you think about that?
For your own self, right I?
Speaker 2 (21:29):
think the the ritual of it, the ritual of taking this
horrible thing that's happenedto you and and like
materializing it into the world.
You know, like it's this, it'sthis chorus, this moaning chorus
, that comes into the world asas being like a healing and
motivating, uh, exercise.
Yeah, you know so.
Yeah, I suppose that's what I'mthinking of is like, okay,
(21:51):
maybe there's like a ritual here, maybe there's some kind of
like creative ritual that youput in that, you know, allows
for some of the spontaneity andthings to happen to, to be a
ballast, I think, maybe for therigor or something.
Speaker 1 (22:07):
Yeah, I mean to reflect on that for a moment.
I think that's exactly rightthat you're describing there's a
container, there is some, someset of steps that are predefined
, but it's really just acontainer for the human
expression to then expand intothat and who knows what that
will actually end up lookinglike.
Right, there's a spontaneity toit and there's the expression
(22:29):
to it, and I wonder what doesthat look like for you?
Ryan, you started thisconversation talking about the
balance or the tension betweenstructure, productivity, control
, and creativity and expression.
But if we were to say, actually, these two things are not at
odds, they can actually workwell together.
What does that look like here?
Speaker 2 (22:49):
Yeah, man, maybe I'm just trying to talk myself into
making a record, you know.
Speaker 1 (22:57):
Have you ever done that?
Speaker 2 (22:58):
Yeah, yeah, former life I was a touring musician.
You know.
I made three records and didmixtapes and used to play all
the time, you know, and at onepoint I was like no more music,
it's done, and that was it what,what was happening, that made
you say that?
And that was it.
What was happening that madeyou say that?
You know I was playing a showand it didn't go the way I
(23:19):
wanted to.
They stiffed me on payment forprobably the 12th time.
I mean, the music industry ismore corrupt than the boxing
industry and the boxing industryis the most corrupt business in
the world.
So I had two young children atthe time and was working on two
bands and doing a bunch of stuffand just was exhausted, I think
(23:41):
, and that kind of was the.
That was the thing that reallyjust ended the music career.
But even more than that, I knewthat I couldn't.
I couldn't just dabble withmusic.
I was so it is so important tome, it was my entire world, you
know my profession, everythingthat I couldn't.
I couldn't just dabble withmusic.
I was so it is so important tome, it was my entire world.
You know my profession,everything that I couldn't just
like do it halfway, I had tolike kill it.
(24:02):
I have to be like no more, youknow, and all or nothing, all or
nothing, yep, and it's likeNope, no more music, not working
in this business anymore, I'mnot making music, it's all over,
it's done behind me and move on.
Now, that's not, it's not thatdramatic.
You know, still, I play songshere and there and there's
guitars kicking around my, myhouse, all over the place, but
(24:23):
there was definitely like a wallthat came down and was like no,
you know, what I mean and thisis probably the tension I'm
discovering is that it does seemto be a wall.
For me is like all in creativeor all in with you know the, the
rational, um, you know uh,rigor based kind of uh lifestyle
(24:44):
, I suppose right, right control, scheduling, left, brain, sort
of yeah left brain, right brain,and there's, just like you know
, a bulletproof wall in betweenthem.
Speaker 1 (24:56):
Yeah, yeah yeah, I'm, I'm, I'm visualizing that wall
like if it's, if it starts tocome down a little bit or go,
however you want to visualize it.
But like that, let's say likethe it's, it's, it's less
impermeable, right, right Nowthere's some actual room to
breathe between both worlds.
(25:18):
Let's call it.
What does that produce for Ryanhere?
Speaker 2 (25:23):
If it's permeable.
Speaker 1 (25:25):
Yeah, less of this, all or nothing.
Speaker 2 (25:28):
But it just makes me happier.
You know, I think it's probablypretty clear.
You know it's interesting.
You know, I think it's it'sprobably pretty clear, you know
it's interesting.
But again, like when I when Idid that, you know, like I
stopped listening to music andjust went all in on podcasts and
then, as a result, developed awhole career around podcasting,
(25:49):
you know.
So it's like, okay, well, yeah,that was either.
The rational side of me is like,yeah, man, that's that's
working for you, that's good,you know.
But I think it's just like, forwhatever reason I'm this, I
have this like black or whitetendency in here.
But there's all this gray grayarea, you know, and it's funny
that, like you know, this wouldkind of creep in professionally
(26:10):
first, but like no-transcript,and I think there was like, you
(26:45):
know, you get so busy and I, youknow, my kids now are in high
school, and so it's just onething after the other, the other
, the other.
There is no relenting, you know, and I'm so blessed and lucky
that, like, I have a successfulbusiness and I have a beautiful
family that loves me and isgreat, but the the like speed
and pace is like it's intense,and I think I felt like I was
(27:07):
like losing a little bit of likewhat I like to do, like I've
kind of forgot who.
I have so many responsibilities.
It's like, well, what do I?
I have so many responsibilities.
It's like, well, what do Ienjoy doing?
And there wasn't like a clearanswer until I was like sitting
in the woods and was like, oh no, you love green chili and tacos
, you know for sure, but youalso really like music, you know
(27:27):
, and it felt really good justto think about these things that
I like to do, you know yeah, solike when you were like in the
woods, like just in nature, itsounds like you were slowing
down and then you were able toreconnect with these just simple
things, uh, that that reallyyou enjoy, that that feel really
good to you and your system.
Speaker 1 (27:49):
Um, and I I don't know about you, but when I
listen to you that that soundslike the opposite of rigid
control.
It sounds like there was moreof this sort of openness for you
.
Does that track?
Speaker 2 (28:05):
Yeah, I think so, but you see, I still start making
lists and action items.
Speaker 1 (28:12):
You got to start somewhere.
Speaker 2 (28:13):
Yeah, sure, I know.
Yeah, no, but that was was itand it was actually comforting,
you know, it was like okay, yeah, you still like things, there's
still things you like there's.
Just there was been a lot ofthings that I've been doing that
I'm just questioning like Idon't think I like this, yeah
okay, yeah, it's amazing whenyou just say it out loud yeah, I
(28:33):
know sitting on snowboardingand I'm like I love, love
hanging out with my kids, but Idon't think I like snowboarding
anymore.
I don't think I do and it's likesomething I'd love forever, but
I was like I actually I hatethis.
I'm not doing this anymore,okay.
Speaker 1 (28:50):
Okay, Okay, cool.
So let's say you keep followingthat.
You just give yourselfpermission to name what you're I
don't like this, I do like thatand then you orient yourself
around that.
What happens then?
Speaker 2 (29:07):
I don't know.
I think I'm happier.
I don't know.
I also feel weird saying thisout of my mouth.
Does it seem strange that youforget what you like and what
you don't like?
Is that odd?
Speaker 1 (29:18):
I think it's actually incredibly common, do you
really?
Speaker 2 (29:21):
Yeah, yeah, that's good, that's good.
So, yeah, I don't know, I thinkthat's you know.
I don't know, maybe that's howyou just go with the flow.
It's like you just pick up acouple branches alongside, if
you like branches to mixmetaphors all over the place
here.
Yeah, you know.
Speaker 1 (29:41):
Yeah Well, just to reflect a bit from what I'm
picking up from you, ryan, partof what I hear is that you
actually are really, really goodat following your interests,
your desires, the things thatyou enjoy, and also you've
encountered a lot of thingsalong the way that resulted in
(30:04):
hurt, burnout, intensity.
You know, that has its way ofsweeping somebody up as well,
and there's like a way in whichwe can lose ourselves in that.
Um, maybe there's some sense ofobligation, uh, that comes in,
uh, to play uh along the way aswell.
I'm just maybe speculating alittle bit based off of what you
(30:25):
said.
And so to your question like isit, is it normal, like, do
people do this where, like theysort, there's a way in which
many of us can lose touch withthat right?
They lose touch with, withwhat's authentic to them because
they replace that with what'sexpected of them, what they're
(30:46):
supposed to do, externalobligation, that sort of thing.
So that doesn't seem strange tome at all.
I I guess, as I'm saying it,I'm curious, like, how's that
landing?
As I reflected back to you.
Speaker 2 (31:06):
Yeah, I think that's it, you know, and I think too
that I've I've led such a funand creative career, like the
way I've, you know, earned aliving over the years is just
like.
It's so fun, you know, and it'slike, and I have a lot of
passion and and a lot ofenthusiasm when I'm going
towards something, and I thinkpart of that is like making sure
that what I'm going towards isvery clear.
(31:26):
And when it's not and I thinktoo, like, the more complicated
your lives get and you know, themore you add families and
businesses and stuff, itdefinitely gets complex that you
kind of lose track of, like,where you're headed, and so it's
hard to sustain the amount ofenthusiasm.
Or rather, maybe the enthusiasmyou know kind of morphs into
(31:48):
something else, cause I'vealways felt like I've got extra
energy.
You know I've got extra energyI've got to burn off, usually
through, you know, physicalactivities, but also through,
like, my pursuits.
And if I have extra energy andit's channeled as enthusiasm for
the mission of where I'm going,you know it's perfect.
(32:08):
But like, if the mission startsto get hazy, because life is
complicated and there's a lot ofdifferent things, you're
balancing the enthusiasm, theextra energy changes its tone.
Speaker 1 (32:20):
Yeah, what do you think?
What do you think is in the wayof having the clarity of
mission?
Speaker 2 (32:28):
What is in the way, boy, I don't know.
I think kind of what you weretalking about.
You know obligation.
You know as like.
You know obligation.
You know as like you know again, I think you know if you want
to be a responsible, productiveperson, then you pick up as much
(32:52):
responsibility and obligationas you possibly can, hold as
much as you can carry, carry asstrong as your back is, take
every ounce on because, honestly, I think that you got an
obligation to the world, likethe you.
You owe the world your best.
You know um, but you know it's,it's tiring, you know, and
(33:15):
maybe it's counterproductive toyou know the, the, the artist in
me that just wants to be flyand be free.
You know.
Speaker 1 (33:24):
Yeah, so it's like you contain these multiple,
multiple selves here, Like the,the, the part of you that's give
the world it's the best and Iowe it to the world.
And then there's just thisartist also in you that's that's
needing some more space fromwhat I hear to the world.
And then there's just thisartist also in you that's
needing some more space fromwhat I hear?
Speaker 2 (33:42):
Yeah, totally, and for some reason there's a wall
between them.
I have a hard time opening thetwo and letting them chill
together.
Opening the door, it's likeeither I'm totally free and I
tasted that you know and I Itasted that you know so, or it's
(34:04):
like, nope, you're taking on asmuch responsibility as you
possibly can, because the worldneeds responsible men.
Speaker 1 (34:09):
Huh, yeah, cool, okay .
So so let's, let's pretend, ifyou're game for this, like,
let's pretend the two of themare seated together at a table
and and you're facilitating somedialogue between them.
I know it seems like they mightnot see eye to eye here, but
what is it that the artistdoesn't understand about the guy
(34:34):
who's operating fromresponsibility that would be
important for him to know?
The guy who's operating fromresponsibility, that that that
would be important for him toknow.
Speaker 2 (34:40):
You know, my first instinct is they'd be critical
of each other first and thenthey'd be encouraging in some
manner.
You know, um, and it's probablylike why I love podcasting and
why I love conversation ingenerals, because you'll meet
each other in the middle.
Yeah, you know, eventuallyyou're going to be like hey man,
(35:00):
actually we got a lot more incommon than we thought you know,
yeah, so they worked throughsome of that stuff to get to
some common understanding here.
I think they would immediately,but there's just no dialogue
there.
I think I mean, maybe for thesake of hyperbole and somehow
bifurcating my personality intothese two distinct entities,
(35:22):
it's helpful to look at them aslike they're not talking to each
other.
You know what I mean?
Yeah, they're probablycompletely reliant on each other
, for sure, but they're notwilling to admit dependency
because they want supremacy.
Speaker 1 (35:40):
Okay, Well, you were just a minute ago.
You were sort of referring to aworld where they're getting
along here, so like it soundslike you're imagining some
scenario where they are actuallyin dialogue, 100%.
Yeah, how do you get there?
How do they get there?
Speaker 2 (36:00):
The more I think about it, the more I think I
just need to write some songs,you know like, actually just do
it, you know, use the rigor partof my brain to, you know time
block a weekend and just gowrite some songs and hang out
with myself.
You know, I think thatultimately might be, might be
just it myself.
Speaker 1 (36:19):
You know, I think that ultimately might be, might
be just it, you know yeah, seemsto link back to what we were
touching on earlier, just likethe what was that?
That novel emotion you'redescribing like, okay, we're
gonna, we're gonna enter intothe ritual, but then we're gonna
fill the space with, with ourexpression yeah, yeah, I think
that I think that's probablyprobably it, and then let things
(36:41):
fall where they may.
Speaker 2 (36:42):
You know, it's just, it's just funny to say this
stuff and realize that, likeit's like I all, I want this all
to like have merit, Like it'slike I'll do it if I feel like
I'm going to get something outof it.
You know what I mean.
Speaker 1 (36:56):
Let me ask you this, so what?
Okay, let's play with that.
So when this tribe or thisgroup of people are out there in
mourning, are they doing itbecause they need to get
something out of it?
Speaker 2 (37:10):
No, I think they're just channeling something that
exists.
I think they just hit thatfrequency and they're just in
that.
I don't think they're trying tobe productive with it at all.
You know, I think, yeah, I mean, I, I put up when I kind of
went no music and was like, okay, I'm being very selective with
(37:34):
my time because I only have somuch of it and I have people
that are counting on me, youknow, because I only have so
much of it and I have peoplethat are counting on me.
You know.
So what I, what I did, is I saidI'm not doing anything that
isn't of service, fun and makesmoney.
It has to make money for me todo it, otherwise I am, I, I'm
(37:56):
letting people down, you know.
So this, this, which workedgreat, you know, it was like boy
that really kept me on astraight and narrow, because
otherwise I would just, I would,I would be in my closet writing
love songs forever, I justwould, you know, and it's like
you gotta, you gotta dosomething else, buddy.
So the, the, the, theparameters really worked well,
but I think the, I think theremight be, I think there's a cost
(38:19):
, you know, and maybe the costisn't worth it To some point.
You know, it's like that was 15years ago maybe yeah, about 15
years ago that I really madethose kind of like very rigid
rules for myself, and it's likeyou know, maybe you relax.
Speaker 1 (38:38):
Yeah, it was 15 years ago.
It's, that's not now.
How much is that needed now?
Yeah, is the question yeah, howmuch you know yeah I'm I'm
really looking forward tohearing the music that you put
out from here did you start withmurderous rage moaning?
Speaker 2 (39:00):
oh yeah, that would be a great hell.
Yeah, it's so funny, nice.
Yeah, yeah, man, I think Icould do that.
I could do that.
Speaker 1 (39:14):
I love it I I this feels like a pretty good spot.
I don't know about you like,how are you feeling just coming?
I, I'm just tuning into whereyou are now.
Speaker 2 (39:24):
It feels good.
You know, this is reallyunexpected kind of conversation.
I'm not sure to do most of theyour, your episodes go like this
.
Speaker 1 (39:32):
I got to say this is probably one of the more unique
ones we've done.
Speaker 2 (39:38):
Yeah, I don't know, it felt really good.
I appreciate it.
Like sometimes you gotta like.
You know, I got a palette ofall these thoughts and emotion
going through me and putting itout like this like makes it seem
pretty clear like there doesn'tnecessarily need to be a
tension between this and that.
Speaker 1 (39:53):
You know, yeah, so well, let me, let me ask you
this, ryan, as we start to closeout.
Then, um, yeah, just tuninginto where you are now, and then
you look, look to how westarted this, this conversation.
Um, what do you want tohighlight?
What do you want to, uh, reallyunderscore coming out from the
(40:13):
session?
Speaker 2 (40:15):
I want to highlight how much I appreciate what you
do.
This has been awesome.
I think it's gotta be veryfulfilling and satisfying, you
know, talking, talking throughpeople and their, their weird
angels and demons on theshoulder, you know, so that's
really cool.
I don't have the opportunity todo a lot of conversations like
this, so I really appreciate it.
I think it's also justinteresting that it like
(40:40):
actually did bring up a lot ofemotion in me, like this is
something that like needsattention, you know, and and
busyness.
As much as I love work, it'snot gonna.
It's not gonna do it, it needs,I need something else.
I can tell if this is what's onthe tip of my tongue right now,
Monday morning or Mondayafternoon you know it's like all
right, like this is probablydeserve some attention, so I'm
(41:01):
going to pay heed to that.
Speaker 1 (41:03):
Awesome.
Well, I am really, reallylooking forward to hearing the
output, and you know, I love howyou started this conversation,
talking about Charlie Parker,and now I want to know what Ryan
Estes comes up with.
I'll be the first Spotifysubscriber, nice, all right, man
, I'll let you know, subscriberNice.
Speaker 2 (41:19):
All right, man, I'll let you know.
Speaker 1 (41:21):
Yeah, awesome, well, ryan, thank you so much for
coming on.
Appreciate it.
Brian, thank you so much.
The walls we build to protectourselves often become the very
barriers that block our growth.
Ryan's session illustrates howmany founders construct rigid
systems, not just forproductivity, but as shields
against vulnerability.
I've witnessed this patternrepeatedly in my coaching
practice.
What presents as productivitychallenges frequently masks a
(41:44):
deeper disconnection fromauthentic joy.
For Ryan, his musicalcreativity has been deliberately
walled off for years in serviceof responsibility and
obligation.
Now, two elements stood out tome from this session.
First, our protectivemechanisms develop for good
reason, but they often outlivetheir usefulness.
Stood out to me from thissession.
First, our protectivemechanisms develop for good
reason, but they often outlivetheir usefulness.
Secondly, reconnection doesn'trequire abandoning structure.
(42:06):
It's not black or white.
We may just need more permeableboundaries between different
aspects of ourselves.
So here's the question worthconsidering what parts of
yourself have you shut down inthe name of success?
The path forward isn't aboutperfect balance, but recognizing
when the walls we'veconstructed have become too
rigid.
Sometimes growth comes not whenwe push harder, but when we
(42:27):
loosen the grip of control justenough to let our authenticity
emerge again.
So I invite you to considerwhat that might look like in
your own leadership journey.
All right, that's anotherepisode of Slate On To Speed Up.
Thank you for listening.
If you enjoyed this episode,please remember to give it a
like, subscribe and a positivereview in your podcast app.
See you at the next one.
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