“Why Successful Comedians Can Become So Boring” - Whitney Cummings
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Whitney Cummings argues in this discussion that high achievers and successful comedians often fall into a trap where their creative output becomes stale because they lack real-life experiences to draw from. He illustrates how constant touring or an intense work grind can dry up the "pool" of material, forcing artists to rely on repetitive observations like airplanes instead of genuine human interaction. Cummings shares a personal anecdote about working in three writer's rooms simultaneously and realizing that his pitches were limited solely by his own workaholic lifestyle; he could only generate ideas based on office life because he had stopped engaging with the world outside of work. He emphasizes that creativity requires stepping out into society to observe behavior, whether at a zoo or a restaurant, rather than retreating into isolation where one's imagination eventually runs dry. To combat this tendency toward professional burnout and "productivity purgatory," Cummings advocates for intentionally scheduling time to do nothing and process emotions without the distraction of technology or business goals. He references Dr. K, a psychiatrist who works with Twitch streamers like xQc, suggesting that staring at a wall can force individuals to confront suppressed feelings they usually avoid through busyness. This practice helps uncover unresolved issues such as shame over past comments or anger toward others, preventing these emotions from festering into unhealthy states. Cummings also cites the Netflix documentary *Cheer*, noting how one of its young stars took months off after her show aired simply to process her fame and experiences, a concept that inspired him to schedule regular processing time for his own life rather than constantly filling every moment with activity. The speaker further details practical strategies he uses to manage decision fatigue and the urge to say "yes" out of fear of boredom or dread. He employs techniques such as scheduling specific times in his calendar to worry about problems, allowing him to address them efficiently without constant anxiety permeating his day. Additionally, he schedules dedicated blocks for making decisions regarding sponsors and other commitments to avoid impulsive choices driven by a lack of self-respect or faith in one's own schedule. He warns against "addiction to dread," where people fill their lives with unwanted obligations just to avoid facing themselves, noting that agreeing to things you don't want to do is often a sign of disrespecting your own time and energy. Ultimately, Cummings concludes that fun and socializing are not wastes of time but integral components for staying relevant and creative in any field, from comedy to app development. He reflects on his past guilt regarding leisure activities versus the current understanding that earning moments of joy is essential for mental health and productivity. By integrating these practices—observing real life, processing emotions through stillness, scheduling worry rather than succumbing to it, and respecting one's own time—he aims to prevent the slow decline into boring repetition that plagues many successful professionals who fail to maintain a balance between their career grind and genuine human experience.
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you said this other thing I listened to
you say this other thing I thought was
so [ __ ] interesting you said in order
for art to imitate life you have to have
a life that's it and this
is definitely something that I see in
high Achievers High performers people
that are sort of on that grind where the
creativity and the space that they had
to be able to think about whatever it is
that they're going to do whether it's
business or career moves or writing or
an online coaching platform that they're
trying to start or content creation or
whatever uh and after a while you take
up so much of your days doing that thing
that the font uh like the pool from
which you withdraw in order to be able
to present [ __ ] is just Barren it's dry
that's it that's exactly it I mean you
see it with comedians all the time you
see these great comedians amazing
observational comedians they get more
and more famous more and more successful
all they're doing is touring and then
all of a sudden they're only doing jokes
about airplanes cuz they're only on
airplanes you know or they like have
nothing to talk about because they don't
do anything I remember I was in a
writer's room for a sitcom that I made
and I was running three shows at one
time three television shows which was
very you know taxing was working all
weekend you know 20 hours a day not
sleeping and we're in the writer's room
and I'm like we need to pitch on like
something that the couple does like on a
weekend and someone was like oh what if
they like went to a wine tasting and I
was like no one goes to a wine tasting
and then like what if she like had to go
to a baby shower I'm like no one goes to
a baby and they're like no Whitney you
don't go to a b like you don't have a
you know and I realized like I was
limiting myself and how you know I'm
like well what if like they're at work
and this happened like I could only
pitch on workaholism like and every
character was all of a sudden a
workaholic I you know and so to me it's
like you know especially being you know
a standup comedian I'm like I got to go
out in the world and I got to do things
and that doesn't mean be mercenary when
you do because there are times where I'm
like I really have to do something
social this week and I'll call friends
and I'll be like can you guys make sure
I don't turn this dinner into work or
turn a hobby into a business because
that's the other thing is that I'll get
a hobby and then I'll turn into a
business yeah you know what I mean spin
this thing up and sell it I'll start
knitting and I'm like oh this will be
good merch I'm like no can't do that you
know an idea I came up with for that
called productivity Purgatory so it's
one of the things that you do for fun
and done purely to like you go for a
walk in nature not because you want to
calm down and just have a good time but
because you once saw an Andrew hubman
podcast that says your productivity
increases by 15% if you spend 20 minutes
a day with sunlight in the eyes or
whatever like productivity Purgatory
everything that you do is in service of
this of this thing I literally got the
Apple watch because the phone is just a
camera at a certain point and I would go
on these hikes and then I would be like
I got to do a video about there's a
plant and I got to do a bit with the I'm
like nope I got to just not even bring
my phone with me on walks anymore
because I will find a way to make a Tik
Tok or or I'll be writing down a I'm
like I got to just like you know so I
really have to play defense on that
because I will slip into that workaholic
[ __ ] or I mean just being on a date with
a guy and being like that's not a just
stop nope that's not a joke you're just
in the moment and you're not going to
make write a scene you're not going to
get a movie idea you're just going to be
in this moment you know and I think that
for people that do all kinds of things
it's not even just creators if you're
someone that's like building an app or
this you have to go out in the world and
see how people behave and see what they
do and you got to like go to the zoo is
basic I call it going to the zoo you got
to go out to a restaurant and see like
okay I'm I'm building my my whoop band
okay people usually wear it on the left
side would you know you just have to
like be in the world and I I I didn't I
always thought that socializing doing
things that were fun were like a waste
of time or that I was falling behind you
know um but now I know that it's like an
integral part about being creative and
staying relevant and it's good to have
fun every now and then like you've
earned it I think that I used to operate
from such a place of like guilt and
you're such a piece of [ __ ] and you're
never going to make it and that served
me really well it just doesn't serve me
anymore yeah this I've got this idea
about uh fuel that you use that kind of
a fuel that
very uh anxious sort of toes toes down
for forward thing is potent for probably
about 5 or 10 years but toxic if you use
it for much longer than that I'm also
big my new thing is doing nothing okay
how do you how are you getting on with
doing nothing it's weird I mean a lot of
times it's kind of just like sitting
outside and just I get to look at nature
chilling but there's just no such thing
as doing nothing I think being around
hes wouldn't class because that's still
doing something if I'm well that's still
counts as doing something probably a
little bit but doing nothing next to a
horse they really like you uh Dr k uh
healthy gamer he's a a psychiatrist
psychotherapist eastern and western
trained and he helps with young people
that have got um screen addictions
gaming addictions he also works with
some of the biggest twitch streamers on
the planet he's done with every big
twitch streamer xqc and and Charlie from
penguin zero and all that stuff and um
one of his exercises that he gets his
like Discord group to do is stare at the
wall for 30 minutes and some of the
things that apparently people break
break down crying it starts screaming at
the wall you're like dude it's staring
at a I haven't done it I haven't [ __ ]
i d do it I don't know if I'm going to
it would be a total fever dream I don't
know what's going to go on I It's tricky
because I I was almost too embarrassed
to say it uh but a lot of times I end up
crying if you're just like being alone
with yourself because you're like what's
what am I running from What feelings am
I trying to not feel what thoughts am I
trying to not have or what comes up when
I stop anesthetizing with busyness with
action with productivity right
and it might just be
like you know that agent that did like
it's right there it's right there oh
that person that said that thing or that
YouTube comment like it's right there
and to go like okay this is stuff I need
to work through this is stuff that I'm
carrying this is stuff that I need to
purge this is someone I need to forgive
like this is something like a Mal I'm
that I'm um trying to get a feeling I'm
trying to get out of right that is
haunting me or it's something that's
taking up real estate in my brain brain
that has no business being there that if
I don't feel this feeling it's just
going to you know alchemize into
something unhealthy anger at someone
else or some kind of shame or [ __ ]
so it's like it's like I kind of sit
there and sometimes have to feel my
feelings and a lot of times it's shame
it's cringe it's God why did you say
that thing to that person you know
sometimes it's to forgive myself
whatever it is but like you know there
was um I don't know if you ever saw that
show cheer on Netflix no it's about the
best cheerleading uh it's such a great
documentary about the best cheerleading
team uh in the country uh Nao it's
actually in Texas the coach is
incredible it's so great such an amazing
show it's about you know these cheer
they work wasn't there a big Scandal
there was a scandal one of the guys send
some texts he shouldn't ass sent and ask
for some photos he shouldn't ask for but
it's still incredibly inspiring it will
inspire you not to send those DMS um and
to never never DM somebody without
having seen their driver's license um
and uh and why am I bringing it up why
am I bringing it up oh so one of the
girls on it they all got really famous
off of it the show was really big and
this girl is just like 18 years old
famous cheerleader you know she's
getting all these brand deals she all of
a sudden has four million followers from
being on this Netflix show being this
you know athlete and I'm in uh in Austin
with some friends and we go see they do
this live show and I you know the show
came out like a year and a half ago and
I asked her I was like so what didn't
you do this summer and she was like oh
I'm going to take a couple months off
just to you know
process and I was like
what she's like I just need to like
process all this and I was like I don't
get like I it I didn't know know what
she was I was like oh yeah I need to
schedule time to process things I've
never thought about that before and it
made me start to take time every week to
just process what happened so I uh I'm
incorporating in America it's taken ages
cuz your guys' tax system and legal
system and everything I only got social
security number two months ago anyway um
started working with accountancy firm so
I've kind of got got a parttime CFO
part-time CFO [ __ ] all he does is
finances and I was at dinner with him a
couple of nights ago and he said yeah
every Friday I just have the entire day
to think like yo you live on XL like
what thinking is that it's just numbers
in numbers out like am I doing deals has
this person paid their taxes blah blah
blah like what thinking is there to do
and the accountant guy the head of this
accountancy firm is like yeah I spend
every Friday just thinking obviously
that's a luxurious position to be in but
like the rule I think is right I used to
I used to have this uh um again another
problem you guys to have a license
equivalency between the US and the UK
which means I need to take my theory
test my theory driving test again in
Texas a place that has by far the worst
drivers I've ever seen in my life and
I've been to Rome right so I I I have to
do that again but I used to love when I
was back home really great hack sorry we
don't give half of our money to a queen
yeah that's true well she's anymore oh
yes uh it's a it's a tough
day um sorry our our our leaders aren't
born into Power yeah if you had a
genetic pull about that big sorry we
don't have inbred mascots running our
country okay all right okay there we
there we go I'm sure you're going to
need to sell some tickets in the I'm
kidding I'm kidding yeah I know love you
guys love you
guys.com yeah um driving the car with no
music or podcast on W what a [ __ ]
like wow what a crazy thing
you know what I mean what comes up and
it's great because you've got the front
of your it's like doing nothing when
you're washing the dishes your front of
the brain is nice and nice and occupied
and the rest of the brain is just free
to do its thing really great really
great I do have a a tool that really
works for me where I schedule worrying
about things and schedule worrying about
things I schedule worrying about things
so it's like if it's like I have to make
this decision about whether I'm going to
do this thing or not say the deadline is
November 12th I'll go okay November 10th
and I'll put it in my calendar I'll say
10:00 a.m. to this I'll worry about it
instead of just constantly perseverating
it until about it until then I will just
schedule when I'm going to worry about
it do you do that with somebody do you
find it's easiest to worry in with a
right hand or with a like if I know I
need to run something by someone I'll go
like hey like come and worry with me
yeah can you come can we go panic
together or if I'm like because it gives
me time to also go who are the best
people to reach out and ask about this
like I feel like it's also your life
starts getting better when you know who
to ask advice from you know again go to
married people to ask Rel advice you
know podcast go to someone who knows
what they're talking about you know so
for me it's also instead of just talking
about it to everyone all the time and
getting bad advice from people getting
sort of mixed data just constantly
worrying about something I'll go like
you have two hours to worry about this
in 3 weeks and then I also will schedule
making decisions about things I get
really bad decision fatigue so it's like
we were just talking about like making
decisions about you know sponsors and
stuff like that you know I can go like
okay I'm going to make this decision on
this date at this time I'm not going to
think about it until then but this is
when I'm going to schedule thinking
about it and so that's like I think a
version that works for me of what your
CFO kind of did and I'll put it in my
calendar it's like and then I can't talk
I'm like I can't talk for the next hour
I have to think about this thing busy
worrying yeah I'm busy worrying or I'm
busy doing my pro and con list but
instead of just constantly worrying
about five or six different things all
the time I will schedule it and that
really helps and then I now schedule
processing cuz like there are times
where you look back you're like why did
I say yes to that what was I thinking oh
I just automatically said yes I just
went into my default software you know
like which we do it's like you move into
a new house like you're going to drive
to your old house for the for for like a
couple months just for like habit you
know so to me yes I have the if it's not
a hell yes it's a no I have like posted
notes all over my desk that are like the
answer is probably going to be but
sometimes I'll just [ __ ] say yes and
I'm like why did I do that like and I'll
just go through I'll go through my
calendar that's a big thing is like I'll
sit down and like really get thoughtful
about my calendar and be like I need to
cut 30% of this out yeah period in the
end yeah there's a a couple of
interesting things that if you find
yourself continuing to say yes to stuff
and then when it comes around regretting
the past version of you that made future
you go to this thing when you get asked
again ask yourself if this was tomorrow
would I say yes because we you know
there's this um hyperbolic discounting
so like you one pound tomorrow is worth2
in a year's time in the way that we see
it and the same is kind of true with
what you're prepared to oblige yourself
to go and do it's like uh something that
you'd say no to tomorrow you feel a
little bit more okay saying yes to for
six months but I first of all take a
good look at yourself and make sure
first you're not addicted to dread which
I think wow Jesus which I believe I was
right number one and number two I would
go oh well I have nothing that
day yeah it's three and a half months
away this is better than nothing that's
what I'm saying about this plan okay I
have nothing that day busy addiction but
why don't I want to do nothing why am I
like I got to do this thing cuz
otherwise I do nothing and then oh God
I'd be alone with one of my thoughts
let's just fill it with something you
know like what are you really saying
when you agree to a plan that you don't
want to do or you're kind of like ah
about like I'll do it like how little do
you respect yourself and how little do
you respect your time you know that
you're saying yes to that like I really
had to look at that and then I didn't go
like well by then and then the lack of
faith in yourself like what if I have a
person by then what if I'm going to need
to be making dinner for my guy that or
going to the farmers market that day
like I need to hold that day cuz what
I'm saying is my life's not going to be
any better by this day and the best I
can do is this [ __ ] thing where I
don't even really want to do it like
what a what a wildly um self-destructive
Instinct what a
sloppy you know Death By A Thousand Cuts
of just fill your life until you die in
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