Episode 45: Beware the Other Box
July 3, 2025
The dangers of black-and-white advice is that it can quietly lock you into a new kind of rigidity, just with better branding.
Rules of thumb are supposed to set us free from rigid thinking, yet they often become rigid themselves. Whether it is advice from improv classes, leadership seminars, or motivational posters, we are surrounded by maxims that say "never do this" and "always do that." This episode questions that binary approach and looks at what happens when one well-intended rule just replaces another. Sometimes good judgment means knowing when to break your own pattern; not because the rule was wrong, but because context changed.
Transcript
i've never done improv personally like taking an improv class or i think i was involved in one of
like an like a small improv random thing at a conference once but generally speaking i really
haven't done anything with improv but they they talk about this idea of you when when you're
responding when one person's does something in the improv your mindset and sometimes literally
what you should say but definitely your mindset you should you want to get into a mindset of yes
and as opposed to a no or as opposed to even a yes but so this means you know in order for a
successful improv scenario to play out everyone needs to kind of play off of each other and whatever
the scenario is that's given and whatever the other people that you're working with
are doing you can't just throw up a wall on that right if if they do something and you're not sure
what to do with it or you don't like the direction it's going that's not a good mindset to be in what
you're trying to and those would be the no mindsets right like the idea would be they do something and
then you kind of shut it down that's going to lead to a pretty bad improvisational you know scenario
instead what you're kind of taught to do is this mindset of yes and so whatever they do your job is
to kind of accept that amplify that and then if you want to move on to something else that's fine
but it should be in some way related and it should some way play off of the last thing and it shouldn't
just be a hard cut it shouldn't just be a hard no so it's this idea of you know a yes and this is
similar advice years ago um i was listening to someone talking about being a a good game master for like
tabletop role-playing games and their advice was similar although slightly different spin
it's kind of a similar situation where you have a group of players and if you're if you're a bad
game master what typically will happen is someone will say they want to do something
and then you say no you can't and that's very stifling in the game and also it doesn't lead to
anything interesting like if and sort of the overall premise of this really was that if you're running a
game and you know again it's like a tabletop role-playing game kind of thing if you're running
a game and you have such a set idea of where you're trying to get the story to go or your characters to
go or whatever then you shouldn't really be running a game you should just be writing a story the i the
whole premise of a game is that other people can interact with it and there's i mean these types of
games they can interact with it and they can change it and you have to kind of work on the fly so the
advice from from these folks was to never say no instead you should say a yes but so the actions of
the players might have consequences that's the but but you should always lead with yes so i these pieces
of advice are are similar i think often in life we get pieces of advice like this where not this
specific piece of advice but things like this where someone comes around to you and says you know you
should never say no you should say yes and or you should never say no you should say yes but or maybe
you've heard this kind of thing professionally right never ask for permission always ask for forgiveness
or never micromanage always empower people or you know never say i can't instead you know say i'll try
or i'll do it or you know whatever they're very black and white right the advice comes in the form this
this pattern comes in the form of never do x instead always do y and i think in a lot of ways
when things are framed this way they're often running counter to the very thing they're trying
to do because in theory the the the reason these sorts of phrases are around is because typically
people do thing a and this phrase is trying to get you to break out of that box and think a little
bit differently and do maybe do it the thing b instead but i think when you when you i have a
few problems with this right because because first of all if you phrase it like that then all you're
doing is is putting yourself in a different box never say no always say yes and okay well now you're in
a new box and i'm not saying that's a bad advice from an improv level like especially when you know
you're first learning to do that i assume that's very good advice it's a good rule of thumb but if
you take it to heart too far right and and you never say no or if in a work scenario you take advice like
never say i can't instead say i don't know whatever professional phrase you've been taught to say
instead you're just in a different box sometimes you can't and you should probably be all honest about
that even other advice you know things that i do kind of agree with when you hear things like oh
you should never micromanage yeah but every now and again you probably should like it does come up
and i think that this idea of taking these sort of pieces of advice that are so black and white and
that are if you use them correctly right if you use them as a rule of thumb they're very very helpful
because probably 95 98 99 percent of the time you should do things in these ways but you still are a
person of judgment like you still have presumably some amount of common sense and judgment that you
probably should use in order to make the right decisions and sometimes the right decision
could very well be to to do the thing that you're often advised not to and i would argue
that that's where people with really good decision making capabilities that's where they shine it's
knowing that you know the last 99 times they empowered their team to do a thing
and now this 100th time this is the thing that now they have to micromanage for whatever reason
or they generally always look for solutions and 99 times before they've looked for and
maybe they haven't succeeded every time but they always look for a solution
and now this this is the 100th time and it's time to
this one you have to say you can't for whatever reason or or again when it's the improv example
the last 99 times you did this you always said yes and but now this scenario is the one where you
have to say no for whatever reason and and and i think that's where people with really good
decision making and judgment capabilities that's where they shine so the you know the the point of
this really is just to say when you hear things that are extreme and i think we're surrounded by
statements that are so black and white like all you gotta do is pull up a linkedin feed and you'll
see it all over the place telling you to always do something in one direction and it's just like
anything else in life the truth is probably somewhere in the middle but at the very least
don't close yourself off to the thing that they're telling you not to do because once in a while
most likely that will be the correct thing to do and the thing you need to do and the thing you should
do and that becomes a chance to to really flex your decision making and do something that otherwise
if you take the you know whatever advice or rules of thumb to heart so deeply that you never ever
consider the alternative that's where where you where you end up right back in the same spot you were
before just in a different box