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The Thing We Never Talk About is an educational podcast about personal finance for creatives and other weirdos. We'll discuss managing cash flow with a lumpy income, when to save & when to invest, and how to reduce stress & build confidence when it comes to your money. No hot stock tips, no complicated strategies, and no finance bro jargon. We'll hear from artists, musicians, creative professionals, and other weirdos about how they navigate these questions for themselves. The Thing We Never Talk About is hosted by Timothy Iseler, CFP®, a former recording & touring audio engineer with 18 years experience in the music industry.
Timothy Iseler: Katie, I end every
conversation with a question for my guest,
and you asked if we could talk about how
I helped you rewire your internal story
to, in, in your words, "Look directly
at and take responsibility for money
instead of remaining in a state of chaos."
Welcome to The Thing We Never Talk About.
My name is Tim Iseler.
I'm a certified financial planner, and I
run my own independent financial advisory
business, helping musicians, artists,
and other people with weird jobs make
smarter decisions with their money.
You can learn more at iselerfinancial.com
If you have a question about money or
personal finance, please send it to me
by visiting iselerfinancial.com/podcast
and I will answer it in a future episode.
And if you enjoy this podcast,
please share it with a friend.
After that, please like and subscribe to
this show wherever you listen to podcasts.
Today I'm speaking with Katie Cunningham,
a freelance producer and writer-director
who works on commercials, events,
and her own narrative projects.
Part of the deal with my job is that
I'm not really allowed to say who I
work with, but I'm always happy when
my clients share that information.
And as you'll hear pretty quickly in this
episode, Katie shares that we have worked
together for several years, and this
conversation looks back at that journey
together from leaving her corporate
job in 2022, to the leap of faith that
launched her current career, and the
real, deliberate work of changing her
relationship with money along the way.
Katie also talks about Produce Your Life,
a project she launched to apply the same
systems and frameworks that she uses
on productions to her personal life.
You can learn more about Katie,
her work, and Produce Your Life
at her website, katiemaysay.com.
And Katie is spelled k a t i e.
So thank you for being here, and please
enjoy this conversation with producer
and writer-director Katie Cunningham.
Katie Cunningham: Hello.
Timothy Iseler: Hello, how are you?
Katie Cunningham: I'm so good.
How are you?
Timothy Iseler: I'm very well, thank you.
How you doing today?
Katie Cunningham: Today's really nice.
It's a beautiful sun,
like summer day in LA.
We love it
Timothy Iseler: Yeah.
Isn't it always a
beautiful summer day in LA?
Katie Cunningham: You know, it's been like
the May gray, June gloom thing out here.
And so it does start to lift as you, like,
come into later part of June, into July,
and you're back to, like, just a beautiful
LA energy, and you're like, "This is
why we, this is why we live out here."
Timothy Iseler: Awesome.
Katie, what do you tell
people you do for a living?
Katie Cunningham: I am a
producer and a writer-director.
So I am completely freelance
and produce everything from
commercials to experiential
events to my own narrative pieces.
Timothy Iseler: When was the last
time you had a conventional job with
a boss and, you know, and a paycheck?
Katie Cunningham: 2022.
Let me make sure that I really mean that.
yes, probably about this time
in 2022, so four years ago.
Timothy Iseler: How did you
decide to make that switch?
Katie Cunningham: You know, you were
actually a big part of that for me.
I had this overwhelming knowing
and feeling that I needed to
write and direct for film.
I was working a corporate job more
in, like, experiential marketing
land, and I just knew if I
stayed in that job, never do it.
Like, I think that there's a lot of
different blueprints for people, and I was
just a person that needed the, the risk to
go out and, like, make something happen.
And I knew that if I stayed in this
corporate job, I would always be in,
in the wheel that I didn't belong in.
And so I knew I had to pull myself
out of that wheel and kind of,
like, leap off the cliff in a way.
I remember talking to you about
it, and I was like, "I think I'm
gonna leave this job, and I think
I'm going to fund a short film."
Which at the time my finances
were not in a place to do really
either one of those things.
And, and the best part of all of it was
you had helped me so much get my hands
around at least, like, the true, the
reality of, of where my finances were.
And so I knew, I understood the risk,
but I was like, "I have to do this."
And you said, "If you have to
do it, then you have to do it."
Like, I'm never gonna stand in
the way of something that you
know that's true in your gut.
And what's really cool is I now make much
more money than I made in my corporate
job and and, like, genuinely love my life
Timothy Iseler: That's fantastic.
I'm really glad, really glad.
We might have talked about this
at the time, but often, when
I'm working with people, theyâ¦
I think people sometimes want
like, just make the numbers
tell me what to do, right?
And there's often, there's the
num- there's the answer where the
numbers say, you know, "I ran the
numbers, you have to do this," right?
Katie Cunningham: Yeah
Timothy Iseler: then often, uh, and
in fact, almost always, that's not
how people make decisions about money,
you know, because, well, like in your
example, the, the safe thing would've
been to stay where you were and keep
getting a raise and keep moving up a
little bit and a little bit But that's
not really how life happens, you know.
People make decisions
based on inspiration.
Sometimes they make decisions
based out of fear, you know.
So I think if you had stayed where you
were, that would've been less about,
kind of less of a financial decision
and more of like a fear-based decision.
Katie Cunningham: Mm-hmm.
For sure.
And there was a, was a piece, umâ¦
Oh, I have chills even
starting to talk about this.
when you and I started working
together, and I'm sure we'll talk a
little bit more about that time, but
y- you made me do the values exercise.
and we whittled values down to five.
I actually was trying to look through
my stuff before we hopped on to see
if I could find it quickly, but I
remember that two of the five that I
landed on were freedom and creativity.
And there's just this thing where, like,
when we started, when I started everything
through the lens of, like, what my true
five values were, I was like, "Well,
I'm not gonna not do this if I know
that I have to create in this way, that,
like, this is the way that I'm supposed
to put my stories out in the world."
And then I also want, I want freedom.
Like, I want something that isn't every
day I log on to a corporate machine and
have nonstop Zoom calls and something
that I don't have control over.
And there was just this understanding
around I stay where I am, then I'm
not really living by my values,
Timothy Iseler: Mm-hmm.
Katie Cunningham: and that was such a big
shift in my entire mindset around, like,
what do we, what do we start to do from
there now that we have that information?
Timothy Iseler: Yeah, that's,
that's interesting feedback
'cause sometimes I wonderâ¦
Sometimes I think people think those
exercises are silly and, and, you
know, to an extent they are, but
it, uh, when you can only choose
three or five or something, it,
it really forces you to get real.
'Cause in this exercise we're talking
about, like, all the values are admirable.
There's none of them that's like
Katie Cunningham: Yeah
Timothy Iseler: maximize
money over everything else.
Like, it's always things you
would w- you would admire if
you saw them in someone else.
And so when you have to narrow it down,
it kind of forces you to ask like,
"Well, what is more important than me?"
And, and sometimes I think people
still answer those based on what they
think they should say versus what
they really s- really want, you know?
Katie Cunningham: I remember
that exercise being, like, pretty
painful because to your point,
you're like, "Well, I want allâ¦
I wanna be all, all of these things."
but it does come down to, like,
what do you truly prioritize
and what's in your soul?
And it was, you and I did it together.
I can't rememberâ¦
I feel like I read through them
and I kinda took a crack at it,
and then we whittled them down to
the five together live on a call.
And internal dialogue for me was very
much a, well, I should want this, but I
actually really would rather have this.
I remember feeling that way and, like,
being very honest with you, um, which
is a testament to you that I felt like I
could be vulnerable and authentic from a
place of like, you know, it- it's scary
to tell people what you really want.
It's like the most, like,
out on a ledge thing.
but it, that exercise totally
changed how I view everything
Timothy Iseler: Yeah, that's excellent.
Thanks for sharing that.
Katie Cunningham: of course
Timothy Iseler: So when you made
that decision, I know that sort
of corresponded with a move.
Um, you were on the East
Coast, now you're in LA.
Katie Cunningham: Yep
Timothy Iseler: How did you set
yourself up for the best chance
of success when you did that?
Like, whatâ¦
You know, you didn't know what kind of
income you were gonna get, and it sounds
like you were outlaying a bunch of
money upfront to make this film happen.
How did you set yourself up
so that you had the best, best
chances of making it work?
Katie Cunningham: to be honest with
you, there were moments where I
probably didn't set myself up well.
But had done a lot of work around all of
the really annoying housekeeping that you
have to do, which, like, we spent weeks
getting all of my different retirement
funds, like, funneled into one fund.
Like, we spent weeks going through all
of my credit card statements or, or bank
accounts, seeing, like, what my monthly
subscriptions were and what we could cut,
and anything that was, like, trimming the
fat off of, off of just general expenses.
And so I went intoâ¦
I, I nomaded for a period when I quit
my job, and, um, knew I was gonna end
up in LA, but kind of wanted to have
that freedom value that we were talking
about, and using that, moment that I
had this awareness, like, that moment
in time I was like, "This is a time
that you could be unmoored, and it might
be the only, might be the only time
in your life, so, like, let's do it."
And it was so cool because
I got to go spend a month in
France with a great friend.
I got to go live in Maine
in a friend's house.
Like, I just got to, like, really
bop around and experience a lot of
different life, knowing that that was
gonna be, like, a finite experience.
Like, it wasn't gonna be forever.
And so from, like, a financial
setup, I had a couple people
that I knew n- that I knew that,
like, needed freelance producers.
And the beauty of freelance production
is you can pretty much do it from
anywhere, and you can always say no.
So there was something
that was really nice.
And, and early on in that
jump, I very rarely said no.
I say no a lot now.
But there was a cool, Like, the
energy matched where I was in my
life, where someone would say, "Hey,
we're, we have this event in October.
you available to do
all the pre-pro for it?
And then, like, we would need you
in the Hamptons August 14th through
20th," or something like that.
And I had this unmooredness that
allowed me to be like, "Sure.
Like, even though I'm not gonna be
in New York, I'll fly back for that."
And started taking these jobs that I think
that really worked for me, that worked the
way I like to work, the way my energy is.
And I just was very open to understanding
that this was not gonna be a time that
felt structured, and I needed to lean
into the kind of like fluidity of it all.
and it changed a lot of just how my
brain worked around like things will
come in when they need to come in,
and when they're not coming in you
can't panic that they're not coming in
Timothy Iseler: Yeah, yeah, yeah.
I lived that way for a long time when
I was a, a touring audio engineer,
and I got, towards the end, I got
r- a lot better about it, but it is
hard in those down times to like, you
know, you have a month off and you're
like, "Why isn't anyone calling?"
And then all of a sudden you've
got gigs stacked back to back to
back for the rest of the year.
So you gotta, gotta enjoy
that downtime when you get it
Katie Cunningham: Yeah, for sure
Timothy Iseler: So what do you
think, as a freelance producer, what
do you think most people get wrong
when they think about your job?
Katie Cunningham: Oh.
I think that a lot of people
think my job is glamorous.
Um, my job is a job.
My job isâ¦
when I'm in a production, it's constant.
It's, I open my eyes to 45 text messages
that need to be answered, and I work
15, 16 hours a day, and I go to sleep
with things still needing to be done.
It is taking me a long time to understand
that I have to set boundaries and,
um, create systems for myself so I
don't go insane in those sprints.
it is a lot of, it's a lot
of holding energy and also,
like, maintaining logistics.
The most beautiful thing of production
is that it takes a lot of people.
I mean, I know that you get that
from, from touring days, where the
running joke that I always make with
this director that I work with a lot
is, like, "If only we were painters."
Like, if only we could just, like,
clock into our studio and stand in
front of a canvas and paint, and
then, like, that would be our craft.
But that's just simply not our craft.
And my craft is bringing, you know,
anywhere from 10 to 150 people all to
one spot and getting everyone on the
same page, and letting them know what
the plan is, and then executing the plan.
And a lot of that is very
detailed, boring work.
It's very, like, you don't enter at
gate two, you enter at gate four.
Timothy Iseler: Yeah.
Katie Cunningham: right at this
place and it's, it's just a lot
of, like, understanding everyone
is coming from and getting ahead
of as many problems as you can.
And some days that is sexy, and
some days that is just, like,
a constant of babysitting.
Timothy Iseler: Mm-hmm
Katie Cunningham: but I do, I really
love it, and I really love the
process of making something like that.
I mean, I just fa- I genuinely fall in
love with every project that I'm working
on and with the people in that project.
And when you understand what
everyone's bringing, it's so
cool and special to see that.
and there's something about the
creative arts too where everyone is
like, "You wouldn't go through this
chaos unless you really loved it."
And I think that that's, that was
the thing that was missing for
me in some of my corporate jobs.
So I love that.
That's a, like, creativity value that
you and I honed in on of just, like,
even though it's chaos and constant,
and a lot of my job is babysitting,
Everyone is there for the same reason,
and it aligns so much with what my
reason is to be there that it is
actually very life-giving for me
Timothy Iseler: Yeah, that's great.
I thought about this as you were
talking that, like, I think a lot
of times when people just throw
around creativity, people think of,
like you said, like a painter or a
musician or an artist or whatever.
But there's s- there's certain jobs where
maybe you are not responsible for whatever
the artifact is, but the job itself
is so dynamic and unpredictable that
it's still a very creative environment.
Katie Cunningham: Yeah.
That reminds me of the first therapist
I ever had, who was incredible.
I was, you know, in this, probably around
the same time I was starting to work with
you actually, I was in her office and
I was like, "I just wanna, like, have a
creative life and I just wanna da, da,
da," and you know, we're just, like, in
that, like, what is my capital P purpose
kind of energy, kind of anxiety swirl.
And she looked at me and she was like, "I
have the most creative job in the world.
Like, I don't knowâ¦
All of my patients who I know so well
walk in that door every day, and I have
no idea what their life has been like.
They're gonna come in, they're gonna
tell me what going on with them, and I'm
going to have to make a plan on how I
guide them through the next 60 minutes."
And she was so fantastic because
she, you know, she would pull in
Greek mythology, she would recite
poetry, like, she would ask me very
roundabout, interesting questions.
And I will never forget her reframing
that creativity, exactly what you just
did there too, where it's like it's not
a painter in front of a canvas only.
It's how do you approach the problems and
how do you bring people together in that,
like, dynamic, I keep going back to the
word fluid, but, like, a very, like, fluid
way of life where every shoot I'm on,
I'm like, "I have no idea what problems
are gonna come up today, but I know there
will be problems, and we'll figure that
out," and that's the creativity part
that feels really, really fun to me.
Timothy Iseler: Yeah, that's great.
What makes a project successful for you?
Katie Cunningham: if people, wanna, like,
really give you the honest answer, like
If people leave feeling
like their cup got fuller
Timothy Iseler: Uh-huh
Katie Cunningham: instead of more
empty, that is success to me.
It, it is hard to create a set where
everyone's frequency raises instead
of, like, gets drained by chaos and
time constraints and money constraints.
And like every- name every
constraint in the book, like,
we probably go up against it.
but some of the sets that have really
worked, you feel people leave at the
end of the day just, like, happier.
Timothy Iseler: Mm.
Yeah
Katie Cunningham: And that's the cool,
that's the coolest, like, most successful
thing.
And it, and then it,
and it sticks with you.
Like, you-- I can remember.
I can name the shoots that I'm
like, "That one was a success.
That one was great."
And some of those, what's crazy,
some of the things that we've shot on
those shoots have never, it's never
been released, or it gets killed.
Or like, the way, like, a lot
of commercials get shot, and
then some don't make it out.
so it's not necessarily that they,
like, won awards or had the most views.
Some had zero views.
it's more like what the energy's like
when everybody leaves for the day
Timothy Iseler: Yeah.
In those sorts of situations,
how much are you putting the team
together and how much is that in place
and you're there to make it work?
Katie Cunningham: it's 50/50.
a good producer curates the
crew as much as he or she can.
there are always things that
are out of your control.
There are always things that I fight for
and then the client wants to go with a
different director or wants to go with a
different DP, and then you have to make,
that crew work, or you have to make that
location work, or you have to make the
certain like script they chose work.
And it's such a, such a balance of knowing
when to say, "I really feel strongly that
this person would be better in this role."
and then when you say, "Okay, like, we
will make it work no matter who is there."
And I have been pleasantly surprised like
more times than I can count when I was
sure something should go one way and then
it goes a different way and we make it
work that way, and I'm like, "That's the
way it should've been the whole time."
so there's a balance of like
surrendering to that and then also
knowing when the right, when I
have to do my job and, and push for
certain people to be in certain roles.
Timothy Iseler: Yeah, yeah, yeah.
That makes sense.
what you're describing is similar to a
lot of the work I did where, you know,
working with a band, certainly you're,
you're trying to prepare, you're trying to
make everything as, as right as you can.
But then sometimes I would also be a
tour manager or production manager,
where you're spending weeks trying to
make sure that the show happens the
way it's supposed to happen, the tour
happens the way it's supposed to happen.
And It, it's totally satisfying
when you've planned everything and
it works, and at the end of the
day, everyone feels good about it.
But the times that I look back when I
feel like the most proud or the most
heroic were the ones where it was
almost off the rails the whole time,
and it still worked, and everybody feels
like, like a hero in that situation
Katie Cunningham: Yeah.
W- there's something on the tip of my
tongue that's kind of around this idea of,
of a challenge or a struggle, and when, to
your point, everything is off the rails,
or a very common thing that people say
is, like, "We're in the trenches," right?
Like, nothing's going well, but
we're gonna b- like, we're gonna come
together and we're gonna make it work.
those are my favorite, most
confidence-building moments of my career.
And it does allow, when you get
through something like that, it
does allow everything else to just
feel so manageable, where you're
like, "Well, if we could do that,
we can do this, so, like, there's no
sense in us stressing out about it."
Timothy Iseler: Yeah, yeah, yeah.
It reminds me of the, the
freedom aspect, you know?
Like, in that uncontrolled environment,
that is both the, the blessing and
the curse, is like you get to be the
one to make it work, but then you also
have to be the one to make it work.
It's like both at the same time.
Katie Cunningham: Yeah,
stakes are important, you
Timothy Iseler: Yeah
Katie Cunningham: It's I have, umâ¦
I love being in charge in a way that's
like I'm gonna be left holding the bag.
Like, I, I like that.
I, I get energy from that.
And when I produce and when I help
other people, if I just, like,
day play on some stuff and I'm not
really in charge of the project, I
obviously, like, do a good job and Iâ¦
or I hope I do a good job, and
I, and I take it seriously.
But there's something for me that
feels most satisfying when I'm
like, "Well, I'm gonna make it work
'cause, like, if I don't make it
work, nobody's gonna make it work."
Timothy Iseler: Yeah
Katie Cunningham: and
I think that that'sâ¦
I hadn't really put together before
that that was also a thing that I
didn't love about being i- at a huge
corporation, where the, the system is
designed for it not to hinge on one
person because it would collapse if it
Timothy Iseler: Right
Katie Cunningham: one person.
And doesn't really hinge
on one person either.
It takes a village, but there are people
who Like, the DP knows if he doesn't
bring the camera and, like, roll the
film, like, we're not gonna have anything.
Timothy Iseler: Mm-hmm
Katie Cunningham: And then the same
way, like, if I'm producing it and I
don't figure out how to get everyone
there and to make sure that the math
is mathing, that gonna ha- we have
to do that or else it doesn't happen.
And there's something around those stakes
and a little bit of the adrenaline that
you get from knowing that you haveâ¦
that the responsibility
is on you, that I love,
Timothy Iseler: Mm-hmm
Katie Cunningham: that I respond,
that I respond to well, I think
Timothy Iseler: Yeah.
Yeah, yeah.
Speaking of the math mathing,
how do you decide howâ¦
A segue.
How do you decide how much to charge?
Katie Cunningham: Great question.
it is tough.
I mean, the answer is that it's and
it's fluid, and it depends always on is
this a job I'm taking for money or is
this a job I'm taking for connections?
Is this a job I'm taking out of love
for a person that's asking me to do it?
and as the person who usually comes into
the project and builds the budget from
the very beginning, it's a conversation
that I have with usually the EP on the
project, so the person who's actually,
like, paying everyone out and, and
managing the big chunk of the funds
on, I think that this is going to take
three months from beginning to end."
I think that, like, it's never fair
for someone to charge their full day
rate if they're gonna be on that long
of a shoot or that long of a project.
And so it's a lot of, it's a dance
and a bit of a negotiation on I think
that this is actually worth 20 days of
my day rate even though I'm actually
going to be working 60 days because
it's more of just a I know every day
isn't a full eight-hour day on this.
I know it's me dipping
in here, dipping in here.
that's a long way of saying that
it's, there's industry standards
and then it's a lot of, like,
flexibility based on factors.
Timothy Iseler: Yeah.
In terms of your day rate, how are you or
when are you thinking about raising that?
Is it like as you get bigger gigs, you're
like, "Well, I should charge more"?
Is it something else?
Katie Cunningham: it's, I think that it's
never a bigger gigs equal charging more.
I think it's a bigger gigs equal more days
Timothy Iseler: A
Katie Cunningham: which is
charging more, but, like, just in
a different way of looking at it.
So When, when w- do I raise my rates?
I wish I could, I wish I had a
better system to, to tell you here.
it is truly all based off of what the
client, like, who the client is and,
and how the EP and I are gonna work.
Yeah.
That's it.
Sorry, I, Iâ¦
There's not a true, like, here's
when I'm gonna bump up to the next
Timothy Iseler: Yeah, that's all right.
You don't need an answer
Katie Cunningham: I wish I had one.
Now I'm like, "This is my homework."
Timothy Iseler: There you go.
Well, let's say that the money works
or, or when the money works, how
do you decide what gigs to take?
Because you mentioned you're taking
less than you did when you made the,
the transition to working for yourself.
Katie Cunningham: Yeah.
the first thing is always schedule.
Can I make dates work?
good example is I'm going to Big
Sur next week with my mom, and
I got offered a gig that shoots
next week, so I turned that down.
That's an easy one.
The next one is more from does it
sustain a month of my lifestyle or not?
my lifestyle is around, like, 10
k a month when it's all said and
done, and I know if I take one
production and it gives me a month of
lifing, to me that feels very nice.
So that's usually kind of my benchmark
on a project that I take or don't take.
if it's someone that's like, "Hey, I
have this huge favor to ask," and like,
"Could you help me out with this?"
I, depending on the parameters of
it, I might take it or I might not.
And then there's a nice, a nice rule
of thumb for me is very much a is
this stress that's gonna happen even
on the, quote, "easy shoots," does
this stress give me a month of ease?
And if the answer is yes,
I will usually take it.
Timothy Iseler: Hmm.
Mm-hmm.
Without naming any names, can you think
of an example of when you turned something
down and, and why you turned it down?
Aside from just like, you know,
going to Big Sur with your mom.
Katie Cunningham: Yeah.
Um, I will turn projects down if I know
that they are going to be chaotic, if I
know that I can't control the energy of
the project, and that could be anything
fr- and there's one, there's one caveat to
that, and I'll come back in just a second.
But i- if I'm not able to use the
way I budget a production, or if I
can't bring my team in, or if I can't
bring the systems that I know, um,
allow me to work really efficiently
in, then I probably won't take it.
the caveat is if I have the opportunity
to work under someone or work under
a production company that I really
would love to know or learn from or
get in with, I'll take a lower job.
So like if someone who would
probably like support a lead
producer, I'll take that just toâ¦
At that point, it's not about the money.
It's all about like learning
from that person or being
in their world for a second.
so it's more of a strategic
move than a financial move.
one of my favorite producers, uh,
his name's Christian Luedtke, and
I use him as an example because he was
a line producer, so like kind of a top
producer for many, many years, like 14.
And someone asked him if he would PM,
which is a lower person on the totem
pole, a lower day rate, all that stuff.
This was a couple years ago.
And he was like, "I don't
know why, but I like said yes.
There was like something in it that I
was like, sure, I haven't done that in
a decade, but I'll do that for you."
And it unlocked this entirely new like
line of business for him through this
other production company because you
get, we've already discussed, like in the
trenches with a team, you bond so quickly.
They see what you're capable of.
And now he is like the most senior
producer at this production company that
I love, and all because he was willing
to kinda like put his ego aside, take a
job that didn't have the title, didn't
have the money that he normally would.
But he was like, "This makes sense for me
to get in with these, with these people."
And it's paid off handsomely
for him for a long
Timothy Iseler: Y- yeah, yeah, yeah.
That's, that's great.
I likeâ¦
Well, first of all, I like that
acknowledgement that there are
sometimes what seem like a step down
financially ends up being a real step
up in terms of what can, what can it do
for your career, or who can it connect
you with, and that kind of stuff.
But I also love the way you, you
said that earlier about, like, being
able to learn from someone else,
'cause I hadn't considered that.
But yeah, w- when you get to
see somebody doing your job
Katie Cunningham: Mm-hmm
Timothy Iseler: f- you know,
from outside of that job, you
know, you can learn things.
Katie Cunningham: You know, I
see this with directors a lot.
It's a disservice, I think,
to all of us when we don't
see doing it a different way.
And, you know, directors are the,
at the helm of the shoot day, and
they're, they're in control and, and
they're running a set in a certain
way with the help of a producer.
But they very rarely see
other directors work.
So I find they're so
different and distinct, and
would very rarely be on a
set in any other capacity.
Maybe as a creative director on
other things, but like for the
most part, they don't watch many
others, like really at work.
And what I am really fortunate to
get to do is as a producer, I get
to watch a lot of directors work.
So when I do direct, I have some or like
I've seen things that work really well,
and then I've seen things that like a
director just totally misses on set and
it causes a big problem down the road.
But from a producer standpoint, know,
I learn from my EPs that I work with,
so anyone who's above me I learn from.
And then I also learn from a lot of
coordinators and PMs and other producers
that work around me, because we're
all on tons of different sets with a
ton of different production companies.
It's kind of the beauty of freelance
in that all of our crews end up
being people who work in so many
different systems, and they usually
bring the best of what they've
learned other places to themselves,
and then they bring that to you.
And this like weird osmosis that
happens, where it does feel like
you're constantly learning or you're
seeing a new approach every time.
And it's good and bad 'cause like
constantly learning takes energy,
and then staying stuck in your
systems is never great either.
so yeah, there's, there's thisâ¦
I will take a job without even worrying
about the money if I'm excited to
learn and like get in with a team.
Timothy Iseler: Yeah, that's really great.
So I wanna switch gears a little bit.
You do all of this production work
facilitating projects for other people,
but you also recently launched your
own project called Produce Your Life.
Katie Cunningham: Mm-hmm.
Timothy Iseler: What can
you tell me about that?
Katie Cunningham: Produce Your Life was
a, totally launched on a whim, which
I think that some of the best work is.
It wasâ¦
I was in the middle of five different
massive shoots, and I w- I felt
like I was running them pretty
well and doing a very good job.
And then I was at home, and I,
like didn't have paper towels.
Like, this is always the example I give.
I'm like, "I was out of paper towels."
I felt like I didn't really have a grip
on anything in my life, and I was like,
"Why am I able to have such a solid grip
on these, massive productions, but I
don't have paper towels set to auto-ship?
Like, I'm so confused."
Like, that's the- if I was running
this as a producer, the first thing
I would do would be like, "What
are the things you buy every month?
Let's set those up to just get
delivered, and then that's one less
thing for you to have to worry about."
So it started on August 1st last year,
and I was in this production studio's, l-
like studio, essentially, on their psych.
And I was like, "I think I'm gonna just
start treating my life like a production,
and I'm gonna make a schedule, and I'm
gonna make a crew list, and I'm gonna make
a budget, and I'm gonna track the budget."
Like, there's just never a production
I would run where I wouldn't
look at the budget every day.
It's just never gonna happen.
I was like, "Why am I not
doing that with myself?"
And decided every week I would kind
of find the framework as I was going.
And so I would post on Substack
every Sunday of kind of the
element of production that I was
applying to my life every week.
And ultimately, what happened was
something really cool, and I got so
much of my life systemized, and I
got so much of my life very clear.
It kind of re- it reminded me of
the values exercise that we did,
but maybe just a bit more granular
or a bit more, like, executable.
That's not really a word,
but you know what I mean.
Like, it was like, oh, instead of
knowing that these are the values,
like, here's what we're actually gonna
do to put those values into play.
So every week I posted, and I started
these people, without really trying,
of wanting to this themselves.
so what's been really cool is I'm in
the process right now of taking all
the Substacks and turning them into
a workbook that you can just have.
or I consult now on the side just
people who are excited to use
the framework and don't really
know how to use the framework.
So that's been so rewarding too,
because it's the exact same thing
I do in production where you
hear a creative idea and then you
put actionable steps behind it.
And people come to me knowing what
they want or having no idea what they
want, but knowing, like, the vibe of
life, of what they're looking for.
And it's a very transferable skill
from making a commercial concept kind
of crystallize and then listening to
someone talk about what they want out
of life and being like, "Well, this is
what I'm hearing, and that feel right?
And then here are the five steps that you
should do to, like, get you your way."
Timothy Iseler: Yeah, yeah, yeah.
The way you described that, that,
systematizing your life and I
have similar tendencies, and I
know we've talked about this.
Like, one of the things you mentioned
that I put in my newsletter at some
point was that I make the same breakfast
pretty much at least five days a week.
Katie Cunningham: Yeah
Timothy Iseler: same thing.
And I, I know to someone, to certain
people, that would seem like I'm being
really rigid or, like, really boring or
something, but to me it frees up my mind.
Like, I don't have to
ever think about that.
Or like, you know, for, for years
when I was touring, I pretty
much always dressed the same.
I always wore a suit, so it's just
like, "What's my shirt for today?"
You know, socks and underwear.
I don't have to think about anything else.
I know how I'm gonna look.
It's all fine ifâ¦
and, and when you put those
systems in place, I think peopleâ¦
Some people would think that it means
that your life gets closed in, but my
experience with it is that your life
really opens up because there's all of
these things that used to just kind of,
like, flutter around in the back of your
head of like, "Oh, I gotta remember.
I gotta remember the paper towels.
Gotta remember this, gotta remember that."
And you get that out of your head, and
then you have so much space mentally, you
have so much space to focus on whatever
you wanna do, even if that's just, like,
getting home from work and relaxing.
You know?
Like, I don't have anything to do.
It's already taken care of.
Katie Cunningham: Yeah.
There's somethingâ¦
I mean, I, I've told you this before.
Uh, I mean, that, that newsletter
the way I thought about structure.
And it, and it comes up in Produce
Your Life a lot, where my direct quote
is like, "I can scream that I, like,
want balance until I'm blue in the
face, but until I have kind of these,
like, restrictions or structure or
time boundaried things in place, I'm
just always gonna be, like, wailing
and screaming that I want balance."
And I really started to y- work this
system and understand that I think a lot
of the, I think a lot of the chaos pr-
not in my, not in this, like, intentional
way, but a lot of the chaos was keeping
me in the wheel of feeling busy and
feeling important, and it was like I
wanted to, like, operate at this, at this
clip that my nervous system was used to.
And what I have found is since I've set
up things to kind of quiet that chatter
a bit, and there's still plenty of things
that I could set up to quiet more chatter,
but I've, I've put a lot of things in
place that there are days, especially
when I'm not producing something,
that I can come home and, like, read.
Or yesterday, I had
nothing to do after noon.
Like, and I just got to and I got
to know that it was, like, totally
fine to relax because when Iâ¦
'Cause that is the, that is the flow
and energy of my life, where I'm either
completely all in on something or I'm not.
And so when I'm not, I need to recoup and,
like, really give my body what it needs.
when you wrote about having
that same breakfast every
morning, I was just like, "Oh."
The, less, like, wise version of me
would be like, "Well, I never wanna
know what I have for breakfast.
Like, I want every day
to be an adventure."
And, and then you're like, "Well,
no, like, everything can't be
an adventure, or else we're just
gonna, like, spin off the planet."
Like, we laugh the ground
into something, you know?
Timothy Iseler: I think as you were
saying that, it's like I think that way
sometimes on, on a vacation or just like
even if it's not a vacation, even if it's
just like a break, you know, whatever,
holiday break or something where it's
like, "Let's make a special dinner."
You know?
Like we're, we're theâ¦
that is the activity.
That's your creative activity.
But when that's likeâ¦
When the activity is one thing you have
to do, and then you're gonna do three
other things that are more important,
like, you know, that, that kind of
spontaneity or that kind of creativity,
it's like, to me, it's pulling energy
away from the other thing, and that's,
Katie Cunningham: Yeah.
Timothy Iseler: that's why
I love systematizing things.
And then also when it comes to like my
job and the work I do with people, that's
one of the reasons I really, really
advocate for automating whatever you can.
Your, your credit card payments, your,
Katie Cunningham: Mm-hmm
Timothy Iseler: you know, transfer
to your savings account, transfer
to your retirement account.
Like don't think about
it, 'cause if you'reâ¦
if you wait until you feel like
you have enough money to save
money, you'll never do it, 'cause
Katie Cunningham: Yeah
Timothy Iseler: always a reason why
you should spend it instead of save it.
But if it just happens and
you don't have to think about
it, you know, you're takingâ¦
Again, you're like taking something
that's always kind of there in the
back of your head, and you're just
getting rid of it, 'cause it's just
happening without you thinking of it.
Katie Cunningham: Yeah.
I mean, and that's, it's m- all of my
credit card payments are now automated,
and my contributions to my retirement are
automated, and then you and I are about to
automate my savings pulls and all of that.
It just, it also, there's something about
it too that takes the emotion out of it.
Um, and I think that that is, the
system is so important, and it's
just one less thing to worry about.
But it's also this, like, it
doesn't have to be a big deal.
Like, that just, you have decided that
that's how much every month you're
gonna put into retirement, and it
goes, and you don't think about it.
And then every once in a while
I check in on that account,
and I'm like, "Look at it go.
This is great."
Timothy Iseler: Yeah.
Yeah, yeah, yeah.
Totally.
So I normally kind of ask this
question about your industry, but this
could be about your industry or, or
it could be about just people sort
of in a similar situation to you.
What do you wish that other people
like you, whether that's producers or
freelancers or creatives or whatever,
what do you wish they knew about money?
Katie Cunningham: I think that freelancers
especially, have to learn what, what our
life really needs to function, and then
you ha- like you have to have that number.
Like you have to know what
your life needs, and I can't
tell you what your life needs.
I know what my rent is.
I know that I like a certain
lifestyle in LA, and I know exactly
what my monthly spend needs to be.
And then you back into like,
okay, what work do you take?
What work do you not take?
When I get something that hits my account,
I immediately am like, "Well, that
will last me for X amount of months."
And just knowing that releases so much
pressure than I think for a long time when
I didn't know what that number was of what
my monthly, my lifestyle cost every month.
It was kind of like, okay, well, I've
made this money, like I hope this lasts
me or I hope that I can afford this thing.
And there was this, um, out of sight,
out of mind thing that wasn't helpful.
That's not a particularly groundbreaking
to say, but it's like I think that
freelancers and people who don't have
a steady thing they can count on is
like, "I'm just gonna figure it out.
I'm just gonna fi- I'm
just gonna figure it out.
It's gonna come, it's gonna go, and I'm
gonna, I'm gonna always make it work."
Which was very much my
MO for a very long time.
Then what I have found is like
understanding really how much I
spend every month, it allows me
to make so much better informed
decisions around what business I take.
And then on top of that, it allows me
to relax and have a clear understanding
of a runway that I have or what
a certain project can afford me.
I can't stress enough how long I was just
like, "make this work 'cause we always
make it work," and it was just this like
stressful feeling in my body all the time.
Timothy Iseler: Yeah, I'm
glad you brought that up.
That's-- I get that question a lot,
including from some guests on this
show, which is like, "I don'tâ¦
I've got it, whatever.
I'm an artist, I'm a musician.
I don't know what my income is.
How do I make a budget?"
Katie Cunningham: Yeah
Timothy Iseler: And when you have that
kind of an income, you have to do it the
opposite way of everyone else, where you
can't say, "I make this much, and I'm
gonna decide where every dollar goes."
You have to flip it the other
way and say, "I spend this much,
therefore I gotta make at leastâ¦"
You know, if you're taking taxes
into account, like, I gotta make
that plus 30% just to get by.
And like you said, it tells you,
You know, if you take a, if you take
a short gig and it pays for your
whole month, you're like, "Awesome.
I'm sorted this month."
Or if you take a big gig and
it pays you half of what you're
expecting, you're like, "Oh, no,
that's a terrible gig," right?
But you have to know first.
Katie Cunningham: Yeah, you have to
know or else it's just like a guess
and then you're taking things that
you think are gonna really help
you out and then suddenly like,
I would have this stress dream.
I don't think I've ever told you
this, Tim, but like it's so good.
It's, I would have this stress dream
of filling up a bowl in the sink.
This is so freaking like spot on on like
a metaphor, but I would fill up a bowl
in the sink and then my whole job would
be to get the bowl from the sink to
like the counter and every time it would
just like all the water would drain out.
Like it turned into a colander every time.
And it was so, these were like early
freelance days and it was just this
like, wait, where is that money going?
Timothy Iseler: Yeah, yeah, yeah
Katie Cunningham: Like I was like,
I was like why am I working all
the time and the money's leaving?
and it's just 'cause I didn't,
I wasn't looking at it.
I wasn't giving it the
attention it deserves.
And to your point, like I think it
was because, I'm backing into my
answer to your original question here,
like I thought I had to know what
I was gonna make to make a budget.
And then I was like, well, I don't
know what I'm gonna make so like I
guess I don't have to make a budget.
And really as soon as I figured out what
I actually need to live and need to put
aside in savings and need to put aside in
for taxes, and then into my IRA and all
that stuff like was like, well now I know
and now like we have this like plan at
Timothy Iseler: Yeah.
very, very similar to the idea
of, of, uh, systematizing things
or automating things or whatever.
I had this conversation with a musician I
know who I, I worked for for a while, and,
and I like him a lot, and he's a good guy.
But, um, he mentioned this thing
that the more he learned about money,
the less he thought about money.
And I think that's so true
because I think when you'reâ¦
I would say that from my experience
when I was growing up, I certainly
thought that about investing.
Like, I didn't know anything about
investing, and I thought that people who
did that were just, you know, they were
obsessed with money, and that's all they
cared about, and they're all greedy,
and, like, I don't wanna pay attention
to Wall Street and blah, blah, blah.
And, you know, I mean, there's some
truth to that, but it's also, like, kind
of an excuse to not ever deal with it.
And then once I started learning about
investing, I was like, "All of this is
so much easier than I thought it was."
Like, I thought this was gonna be
really, you know, really complicated
and also kind of, like, feel bad.
And instead it's like, you know,
it just, yeah, it just got easier.
Learning a little bit about it made
it easier instead of this scary thing.
Katie Cunningham: Yeah, I definitely
relate to that and definitely relate
to the piece of like, it's a little
bit of like the enemy you know.
It, which is like not the
right way to put that.
Like, money is not the enemy, but
like it's a, you're never gonna
be able to get your hands around
something until you look at it.
Timothy Iseler: Mm-hmm
Katie Cunningham: there's aâ¦
I really love having a teacher or
like a shepherd through something.
Timothy Iseler: Hmm.
Katie Cunningham: and that would be
another big thing that I would tell
people to do is like, especially
in the age of AI and in the age of
like social media influencers that
can teach you things about money,
anything, like find what works for you.
But for me, I like having a
teacher and I like having someone
that's kind of in it with me.
And that has been probably like
the forcing function I needed.
It was more like an accountability of you
being like, "Okay, we're doing the thing.
We're we're, we're picking your values.
Like we're setting up this account and
that means that you're gonna take all
of your retirement accounts that are
scattered all over the place and we're
gonna bring them together and you're
gonna look at it and like here we go."
and that was just like a very
important part of my journey was
just have someone like my face to it.
Timothy Iseler: Yeah
Katie Cunningham: which is to your point,
like once we did that I was like, "Oh,
this actually like isn't that bad."
Timothy Iseler: Yeah.
I, I don't consider myself a therapist,
so I'm not trying to put this out there.
But in a way, I think sometimes it'sâ¦
Sometimes I think the value of therapy
is just that you're able to say something
out loud that you've kept inside.
And I feel like there's a similar quality
where, like, just sort of saying, like,
"Okay, this is, this is what it is."
Like, you know, I'm not telling you
it's good, I'm not telling you it's bad.
It's like, this is just what it is.
And in that process, you get to
sort of see yourself outside of
your own head, if that makes sense.
Katie Cunningham: Yeah.
And money is such a funny thing
because it, I think it's changing.
I think that more and more people are
talking very openly about it and are
sharing, like real like figures or real
things that they are struggling with.
And I remember when, my friendsâ¦
You know, we grew up with our
parents saying like, "card debt is
the worst thing you can ever be in."
And it was just that.
So we had this like shame around
that, and around loans or, or
borrowing money or anything like that.
And I remember when I started being honest
with people about needing to dig out of
credit card debt, and then finding so
much solace in like everyone either being
like, "Hey, I was in that situation too.
Like, it's totally cool.
You'll get out."
Or like, "Hey, yeah, I moved into a house.
I'm like 20k in debt right now.
Like, I'm gonna figure out
a way to get out of it."
It was like totally the thing like when
you air a secret, and then everyone's
like, "Oh, I have that secret too.
Like, it's totally fine.
We'll figure it out."
it's just so much better than when you
just like sit with it in your brain.
Timothy Iseler: Yeah.
Yeah, Cause the story you tell
yourself is always worse than whatever
your friends are gonna tell you.
Yeah
Katie Cunningham: and I think that
what I tell people now, which is
exactly what you told me when I
was like, "I'm gonna quit my job.
I have really not a lot of safety net,
and any safety net that I do have I'm
gonna be pouring a creative project."
But I will tell people that
I have now, I, I now have no
debt outside of my car payment.
And, like, that is a very cool
thing for me to be able to say
as someone that I think always
thought she'd be in debt forever.
Timothy Iseler: Hmm
Katie Cunningham: like, a, this is, like,
a, a story of like, well, I am bad at,
with money, and, like, I'm just always
gonna have this, and, like, this is fine.
I'm gonna make my peace
with it kinda thing.
Timothy Iseler: Yeah
Katie Cunningham: but when people stress
about leaving a job that's making them
miserable or, like, wanting to take a
trip somewhere that they feel very called
to or do some sort of, like, go back
to school or, like, fill in the blank.
Like, anything that they just feel called
to, I always tell them the story of, of
me and you deciding, it's like, well,
this isn't on paper the smart thing, but
I can wholeheartedly tell you that the
reason I'm good at my job and the reason
that I get the opportunities that I get
job is because I made that first short.
And it's not, it's not that it, like,
won awards or went to festivals.
It taught me so much so quickly,
and then it allowed me to point to
something when people were like,
"Well, what have you even done?"
Or, "Oh, you direct?
Like, what have you directed?"
Like, i- having anything for me to
be like, "Here, I've done this,"
was, oh my God, it was priceless.
Like, it could'veâ¦
It's worth 20x what I ended
up going into debt over for.
Timothy Iseler: Yeah, yeah, yeah.
It's like you, you spent that
money building a resume that
you could show everybody.
Katie Cunningham: Yeah, and it's
more, I think more than anything,
it, it was a crash course, and it
taught me things to look for, right?
Like, it's like, well, I just
threw myself in and I made a lot of
mistakes, and I would do things wildly
differently now after four years.
But it, it taught me, like, how
to pull permits, and it taught me,
taught me how to edit something,
and there were just all these things
that it would've taken me much longer
to learn if I didn't just do it.
Timothy Iseler: Yeah.
Yeah, I don't throw this out a lot
because I think for some people
it's, a little hard to swallow, but
you'll- you can always get more money.
Everyone can always get
more money, you know?
Katie Cunningham: Mm-hmm
Timothy Iseler: like, I get it, like,
above a certain age, going to work might
be physically difficult, but below that,
everyone can always get more money.
But you won't get more time, and you
won't get more opportunities, you know?
So, like, it's totally possible that
you could have taken swing and, and it
didn't work, and you would've found a job
because, like, you can always find a job.
You can always find more money, you know?
There's always the next thing.
Um, which is not to say that everybody
should, like, only live for today,
but it's like, if you, if you, if
you feel like it's the time to take
a big swing, you might take aâ¦
You know, it might be the time.
Katie Cunningham: Yeah.
I can't express enough
how much like thatâ¦
I think that I was at a point in my
life where I would have done it anyway.
Like, I don't think that I, I don't
think I needed your blessing, but I
felt so supported by you, and I felt
so, you as this person who had kind of
walked me into the first rooms of, like,
being a financially empowered person,
you were like, "Fuck it, you b- you
may as well," you know, it's kind of
this, it was kind of this like, yeah,
if you feel like this, you have to.
it was this like, oh, there's so much
nuance and there's so much support
that when you just decide, right?
Like, and, and I think that, that you
b- I've told that story to so many
people and I think that it kind of
rattles the cage on, on the black and
white rules that we think we have,
where it's like, "Well, my financial
advisor told me to go into debt."
Timothy Iseler: And
look how it turned out.
Katie Cunningham: And look,
and look how it turned out.
It was, it wasn't debt.
It was like an investment, you know?
Timothy Iseler: There you go.
Investment in yourself.
Katie Cunningham: Mm-hmm.
There we go.
Timothy Iseler: There you go.
Katie, I end every conversation with
a question for my guest, and you asked
if we could talk about how I helped
you rewire your internal story to, in,
in your words, "Look directly at and
take responsibility for money instead
of remaining in a state of chaos."
do you feel like we covered that?
Do you wanna add anything to that?
Katie Cunningham: it's so funny
hearing that because I know I wrote
that, and even when you said it, I was
like, ooh, that just, like, hits me,
Timothy Iseler: Hmm
Katie Cunningham: in a way
that, like, that is what we did.
And I think that it
doesn't happen overnight.
This is something that I really wanna make
sure I say, and I wish that I had heard,
or maybe I did hear, but it didn't land
or stick on me for a long time, is, like,
it's just a series of very small steps.
Timothy Iseler: Mm-hmm
Katie Cunningham: And if you try to do it
all at once, it's gonna be overwhelming.
And we have worked together now
for years, and it's not like we
talk all the time, but there's aâ¦
Uh, even just what we talked about
a couple weeks ago, it's like, okay,
that's just the next step now, and
then we're gonna t- and then we'll
find the step after that, and then
we'll find the step after that.
But that kinda does go back to my point
on, for me, I needed a person to hold me
accountable and to be with me through it.
otherwise, I don't know if I ever
would have forced myself to do it.
Timothy Iseler: Yeah, yeah.
I wanna come back to that question, but
the way you said that, about it's just
the next step, it is just the next step.
I think o- one p- area where I am at
odds with a lot of other financial
planners is I don't really think the
point of a financial plan is that
I'm gonna map out everything you
should do for the rest of your life.
And I'll say like, "Okay, until
you're this age, do this, and then
at that age, switch, and then, you
know, when you're 72, do this."
Katie Cunningham: Right
Timothy Iseler: that's cool, and it
looks cool to generate the, the big
report that tells you everything that's
gonna happen the rest of your life.
But I just don't evenâ¦
I think it's impressive, but I don't
think it matters, because as soon
as I hand you that, it's obsolete.
You know?
Like one month goes by, it's obsolete.
And, and everybody who does it that
way, o- other financial planners,
they all kind of know that, and they
know that like, "Yeah, you're gonna
have to come back next year, and the
thing I told you is gonna happen next
year, we're gonna have to adjust it."
You know?
So
Katie Cunningham: Yeah
Timothy Iseler: I, I understand why
people want that kind of a plan and
they want that kind of certainty
of like, "If I just do this until
I'm 65, then it'll all work."
And I appreciate that and, and
What I want is to get people
pointed in the right direction.
Katie Cunningham: Mm-hmm
Timothy Iseler: And if you're making
good decisions now, like, you know,
if you're saving and investing, if
you're keeping your expenses where
they need to be, if you're keeping your
debt where it needs to be, all those
other decisions later will get easier.
You know?
Even though we don't know what's
gonna happen 10 years from
now or even one year from now.
We don't know, but if you're, if you're
in a good spot right now and you're headed
in the right direction, it'll get easier.
And that's sort of how I think
about financial planning.
It's not so much, "Let me tell you
everything from now on until you die."
It's like, " let's Figure out what you
need to do in the next six months."
And
Katie Cunningham: Yeah
Timothy Iseler: if we can get
that right, then we can look at
the next thing when it comes up.
Katie Cunningham: Which is very,
very, like, production mindset, right?
It's very, um, it's veryâ¦
This is, producer life, like when
I work with people, I'm like,
"We're not solving for your life.
We're solving for, like, what do you want
to feel in three months when you wake up?"
Like, we're just going against
that date, and we can't know
what comes after that date.
We can't focus on it.
Like, you have to, you have to baby step
it out, and you have to have a deadline,
and you have to know that, like, you're
not solving for the next six decades.
'Cause to your point, like, as
soon as you hand me that, like,
one, I'm gonna change my mind,
Timothy Iseler: Yeah.
Katie Cunningham: two, like,
the markets are gonna change.
Timothy Iseler: Yeah,
Katie Cunningham: three,
AI's gonna be here.
Four, like, a thing that I could
never see coming that just,
like, blesses me is coming.
It's gonna come in and change
everything that we're doing,
and there's just no point in us
acting like we know everything.
But it's kind of that metaphor of
the plane turns one degree as it
takes off from LAX, and, like, you
either end up in New York or Florida.
Timothy Iseler: Right
Katie Cunningham: it's that, and I think
that, like, that's very much what I, I
love about you and what I love about,
like, the way you approach finances is
it's like, let's just keep this, like,
okay, it's time for the next little
degree turn, and then the next one.
Timothy Iseler: Yeah.
Thank you for saying that.
Katie Cunningham: Yeah
Timothy Iseler: I do wanna giveâ¦
get back to your question and do a
little mutual appreciation society.
So you and I talked about this last
time we spoke, but that all of that
work around changing the internal
narrative, I used that with you as
my success story for years as kind of
like my model, my model client when I
would tell people about what about the
work that I do or that kind of stuff.
And when we started working together,
, it came up that, like, you were the
one in your family who was like,
in air quotes, "bad at money."
Right?
And, like you said, it doesn't happen
overnight, but we were able to do some
things and make some decisions and make
some changes, and then over the course
of, like, a year-ish, you had all of this
evidence that you weren't bad at money.
You know?
And it wasn'tâ¦
You know, it's like you're telling
yourself the new story, but then
you're also building evidence
that it's not true, you know,
because you're doing these things.
You are good at money, right?
And thoseâ¦
to the point of, like, keeping things
inside and the story you tell yourself,
like all of that stuff of like shame
about money , I'm bad at money, I
can't do this, people like me don't
do this, those are just stories.
And if you're telling yourself a story,
there's always room to tell a new one.
But, you know, again, to your point,
you c- it's really, really hard to just
one day say like, "Okay, now my-- all my
internal dialogue that my entire life has
been one way, now it's a different way."
It's hard to do that, so you kind
of have to kind of like baby step it
Katie Cunningham: Mm-hmm
Timothy Iseler: just face, you
know, o- one step at a time,
build up a body of evidence that
shows like, "Nope, I'm actuallyâ¦
I don't have to feel bad about these
things that I used to feel bad about."
Katie Cunningham: Yeah.
It wasâ¦
the bad at money thing came
from a- a place that was
like, I liked to spend money.
Like, I liked to go out, I liked to
buy the toy that I wanted at the store.
I liked to take the trip.
Like, I li- like, there were
always things that I wasâ¦
All it was was I was prioritizing
experiencing something over saving,
Timothy Iseler: Mm-hmm
Katie Cunningham: and that
meant that quote, bad at money.
And that wasn'tâ¦
I don't think that, like, wasn't
from my parents or anything.
That was just, like, a societal thing
that was, like, being, that was kind
of being, like, pushed around at me.
And I think at the end of the day, what's
really pretty cool is, like, again, like,
really digging into what was happening.
There was a world where I was like, "Wait,
maybe I rock at money," because I do
like to have this lifestyle that I have,
and I find ways to pay for it myself.
And I always make it work, and
I had 401s that I hadn't looked
at in 10 years because I just, I
don't know, like, didn't, like, r-
didn't have awareness around them or
didn't think that there was anyâ¦
Didn't understand that they
could really compound and grow.
And, yeah, I think it's really important
that looking at everything directly and
starting to work it showed me, like, how
to change mindset around, like, well,
you've everything that you've needed, in
one way or another, and, like, now we're
just gonna keep going and doing that in a
more intentional way over and over again.
Timothy Iseler: Yeah.
To your point about, like, you know,
wanting the nice thing, wanting or
whatever, the new thing, the new toy, the
new whatever, wanting to take nice trips,
there's nothing wrong with spending money
if you can afford that money, right?
You know, like, if you make enough
money that you can pay for a nice trip,
and you're still saving, and you're
still keeping your debt under control
and whatever, like, if you're doing
all the right things, spend the rest.
You know?
That's what it's there for.
If you're, like, going into debt and
you're not saving anything, like,
okay, then it's time to change.
Butâ¦
Katie Cunningham: it was
such a fascinating thing.
It was back to the, like, bowl turns
into a colander thing, where was
like, "Well, I ma- I have this, like,
tap of water that's coming into my
life because I'm working for it."
And then I just have awareness over where
it was all going, and I didn't haveâ¦
and this is one thing too that I'll, I
know we're kind of wrapping up, but that
I'll leave you with and leave people
with, like, I think that, like, to start
to rewire your spending habits and,
like, how you look at your finances,
like, you have to do it manually,
or I had to do it manually at first.
And, like, it wouldn't have worked,
and I know because I tried, to,
like, use the software that tells
you what you're spending that, like,
is like, "This is what you spent
this month in these categories."
Like, I had to, like, really go
in and, like, look at that to feel
it and to understand it, and maybe
that's just the way my brain works.
But there was something around the
attention that I gave that phase, and
that I have to do now every year with my
taxes, because I'm freelance in an LLC,
that I have to look at everything that
I spent and figure it out, and figure
out, like, what's a business expense.
And it is really, it'sâ¦
I hate it.
It's the worst part of my year.
Um, but it does, it is
intentionality, right?
Like,
Timothy Iseler: Yeah
Katie Cunningham: it isn't me just,
like, checking a thing and then
being like, "Oh, okay, I spent that
much at restaurants this month."
It's like, "Oh, damn, am I gettingâ¦
Is this where I want this
money to be going every month?"
Timothy Iseler: Yeah
Katie Cunningham: or no.
And there's a little bit of, not hard
work, that's not the right thing,
but just attention, I think, that you
have to give to it m- and question it.
Timothy Iseler: Yeah, yeah, yeah.
It's-- I-- There's this quote that's
often misattributed, so I won't
attribute it, but that what gets
measured gets managed, you know?
And I know certainly, like, if you start
paying attention to how many steps you
take, like, you're gonna take more steps.
If you start,
Katie Cunningham: Yeah
Timothy Iseler: look- looking
at your nutrition, you're gonna
eat more nutritious stuff.
Like, just whatever you pay attention
to, you're gonna start to doâ¦
uh, be more intentional about that.
Katie Cunningham: Yeah, I'm
actually writing that down.
I've heard that a trillion times,
but it's really n- like, you know
when somebody says it and you're
like, "That's the trillion and one
time that I needed to write it down,"
Timothy Iseler: Yeah.
Katie Cunningham: it is this, uh, oh,
it's like so true for everything, right?
But I think that it is a, especially
when it comes to finances, you're like,
yeah, it, when I know where I'm trying,
where I currently am or like what the
measurement is, then I'll be aware
if this month is longer or shorter.
Timothy Iseler: Yeah.
Awesome.
I think that's a great place to end it.
You feel good about this?
Katie Cunningham: I feel great.
That was so fun.
It's so fun to reliveâ¦
I mean, I can't believe
that it's been so long.
Timothy Iseler: Yeah.
Yeah, yeah
Katie Cunningham: But I
think it's been five years
Timothy Iseler: Wowie, how about that?
Katie Cunningham: Which is crazy.
Timothy Iseler: Awesome.
Thanks for doing this
Katie Cunningham: My pleasure.
Thank you for asking me, and I will
forever preach the gospel of Tim.
Timothy Iseler: Love it.
Thank you, Katie.
Bye
Katie Cunningham: Bye.
Timothy Iseler: Thank you to Katie
for speaking with me today and
sharing so much about her story.
I continue to appreciate how willing
Katie is to be vulnerable when it
comes to talking about money and what
it means to be, air quotes, "good
or bad" with financial decisions.
It's been a real privilege to work
with her over the past five-ish years
and to watch her build the career and
life that she wants on her own terms.
So thanks again to Katie Cunningham, and
you can learn more about her work and
Produce Your Life at katiemaysay.com.
That's it for today.
Next week, I wanna talk about kind
of a tricky topic: what happens when
the questions you have about money
aren't really about the money at all?
There's this sort of belief in our society
that making financial decisions should
just be a matter of crunching the numbers,
and then the answers will become clear.
But more often than not, the underlying
issues are less about making the
numbers work and more about life.
I will see you back here to
discuss that topic next week
The Thing We Never Talk
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