September 8, 2025 • 31 mins
Anna Sale is what you might call a professional “haver of hard conversations”. As the creator of the podcast “Death, Sex, & Money,” she’s spent years exploring the big questions and taboo topics people tend to shy away from. In this episode, Anna reflects on what she’s learned from all of those conversations – what’s helped, what hasn’t, and what she’s still figuring out.
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Speaker 1 (00:14):
Pushkin hard conversations. I think we talk about them as
if there's these discreete things. What hard conversations are in
(00:35):
service of is a relationship and that is ongoing.
Speaker 2 (00:40):
Anna Sale is the creator and host of Death, Sex
and Money, a show that explores the big questions and
hard choices that are often left out of polite conversation.
She believes that sometimes the most powerful thing you can
say during a tough conversation is nothing at all.
Speaker 1 (00:58):
I think often when people jump in to fill gaps
in silence, it's to indicate that having an uncomfortable feeling
is okay.
Speaker 3 (01:06):
And maybe there's this other thing, you know, like, Hugh,
have you talked with arapist?
Speaker 1 (01:10):
You know, like we want to say something that's going
to make it feel tolerable, and sometimes big things just
need a little bit of air.
Speaker 2 (01:24):
On today's show, How to Have Hard Conversations, I'm Maya Schunker,
a scientist who studies human behavior, and this is a
slight change of plans, a show about who we are
and who we become in the face of a big change. Lately,
(01:49):
the world has been feeling super heavy, and it's made
me lose my appetite for hard conversations in my personal
life about even the small stuff. This worries me because
hard conversations are essential. They're how we process and work
through the challenges in our lives. Today's episode is a
gentle nudge to initiate those conversations that need to be
(02:11):
had and to bring our empathy, patience, and care to
these exchanges. Anna Sayle has spent her career leaning into
difficult topics, both on her podcast and for her book,
Let's Talk About Hard Things the life changing conversations that
connect us. In this episode, Anna reflects on what she's learned,
(02:32):
what's helped, what hasn't, and what she's still figuring out.
I wonder if you remember a time where you really
struggled to say something important to someone else, and what
was it about it that made it so hard.
Speaker 1 (02:46):
I have four sisters, So in any family, as you
get older, you realize that, like, the different siblings have
very different experiences in the family depending on how they
align with parents' expectations.
Speaker 2 (02:59):
Or I'm one of four, so you know, totally get it.
Speaker 1 (03:01):
Yeah, yeah, So I remember different sisters of mine at
different points in their lives. Teenagers call just would have
different responses to the way they talked about our parents
or whether they were felt like they had our parents' approval.
And I was a middle kid who did well in school,
and when I did things that were against the rules,
(03:23):
I never got caught. So like I just like slid through,
you know, I just like knew how to bob and
weave and didn't really have trouble with my parents and
other sisters of mine, like they had different responses to
confrontation and had different relationships with our parents. And so
I can remember those early conversations about, you know, try
and understand when something was upsetting them, and then also
(03:47):
having that parallel conversation or like desire to be protective
of how I saw our family and how I saw
our parents think it was too upsetting to let their
version of what their experience in our family had been
for me to sit with the conversation.
Speaker 2 (04:07):
Do you feel like you play a mediator role within
your own family, which is when you see that there's
some sort of strife, you try and actually facilitate an
open dialogue about it.
Speaker 1 (04:20):
Yes, And I think I would have more fully owned
that earlier in my life, because there's a way that
that fit with my idea of myself as super relationally
advanced and skillful. But there's this way that trying to
be in the middle and moderate and like help people
hear each other in ways that you think that they're
missing that that's like a power move that's kind of obnoxious. Like,
(04:47):
so when you step in to moderate something, you're becoming
the podcast host and the difficult relational piece in your family,
and not everybody wants you to play that role.
Speaker 2 (04:56):
Absolutely. I ask this because I am cut from the
same cloth. I don't know if it's a pathology around
peace seeking or the fact that my brain kind of
instinctively says, of course, a conversation would make this better.
But I feel such an impatience with silence and with
(05:16):
just pushing stuff under the rug that I feel like
a desperation in my life to expose everything, even if
it leads to a sense of calamity in the moment.
I think I just instinctively believe will be some sort
of payoff down the line.
Speaker 3 (05:32):
You so you're a disruptor, Yeah.
Speaker 2 (05:34):
Very disruptive, and often it works, but then sometimes it
makes things worse. And that is really a failure of
mine to empathize with a person who would prefer to
not talk about the thing I'm placing kind of a
norm on the other person, or I'm assuming they carry
my psychology.
Speaker 1 (05:54):
Yeah, and I totally get that impulse, especially when it's
like among people you really love and you want you
want it to get on with it. Let's just like
get on with it and move to a new way
of understanding each other. I mean, I wrote a book.
I wrote a benmore. I had a whole chapter about family.
I was like sharing drafts with all my family members.
Speaker 3 (06:15):
How's this read to you? How's this read to you?
Speaker 4 (06:17):
So?
Speaker 1 (06:18):
I think I was definitely playing that role when I
was doing that, and then it was kind of like, Okay,
I've done that.
Speaker 3 (06:25):
We're just going to like step.
Speaker 1 (06:26):
Back and let everybody have their own experience in the
family and sort of be a member of it and
observe and realize that this is an organism that has
a lot of different stuff going on.
Speaker 2 (06:37):
Yeah, so zooming out a little bit. I mean, you've
obviously made a career around having difficult conversations with people.
How do you prepare for a hard conversation with someone
with your family, with your husband, with friends. Yeah.
Speaker 1 (06:54):
When I think of hard conversations now. They don't happen
during podcast recordings. They happen with my husband, they happen
with my closest friends, because those are the ones where
there's stakes and where it hurts if you feel like
your intentions are not sort of seen clearly, or that
(07:14):
I'm missing something that's that I'm doing, that's really hurtful.
So I think that the way that I try to
prepare is I can feel it in my body when
I get seized up with sort of like I get
something to got to bring up, you know, I'm feeling wronged,
you know, And often it's something around feeling overwhelmed or
(07:36):
like some way that I've tried really hard hasn't been
sufficiently acknowledged and I'm worn out, and it's really hard
not to just start the conversation right in that, you know,
like pissed off way, Yeah.
Speaker 2 (07:51):
Like you don't appreciate that I'm doing the dishes every night.
Speaker 1 (07:53):
Yeah, And that doesn't always go well. It's like how
do I slow down and take a breath, And then
after I sort of can breathe a minute, I have
just a little bit more space around the emotion of
(08:13):
it that I can like be a little bit more
in control of how I respond, because when I don't
take that minute, it's just if you're pissed, you've got
something to say, it doesn't land well, and then you're
feeling like you're having to defend yourself. Then it's just
like tight self protection defensive Anna, She's just going to
(08:36):
be present in protecting herself until she gets tired.
Speaker 3 (08:40):
Then you can finally resolve.
Speaker 2 (08:42):
And I'm assuming you lack receptivity to what other person's saying,
so nothing other than Anna, you are totally right.
Speaker 3 (08:50):
Oh my god, And how could I not have seen?
Speaker 2 (08:53):
And I think to myself every day how lucky I
am that you were willing to marry me and that
you do do the dishes.
Speaker 3 (08:58):
My god, Maya, maybe we should get married.
Speaker 2 (09:01):
I know, I think so. So I think we can
all imagine pretty clearly what the pissed off version looks like,
Oh my god, you never appreciate me. What is the
more like, take a deep breath, slightly more reflective version
of that conversation? Look like?
Speaker 1 (09:17):
What I try to do is just starting that conversation
with like, Okay, can we back up and talk about
how we hope this thing goes?
Speaker 3 (09:25):
What do you hope for it? What do I hope
for it?
Speaker 1 (09:27):
It's trying to get to that place where you have
the spirit of Okay, I am doing the best I can,
and this person I have conflict with right now is
doing the best he can? And how do I not lash?
And like lash out is a good word, because like,
my kids are elementary school age, and I can see
when I lose my patience and I get a little
(09:49):
like snippy, it almost goes down like a little ladder.
I get snippy about something, getting get your shoes on,
get in the car, And then I can watch my
nine year old get snippy with my six year old,
and it's just like, oh, this isn't about some like
fundamental you know, misalignment and chores in this house. This
is like I felt bad, I madebody else feel bad.
(10:09):
They made somebody else feel bad.
Speaker 2 (10:11):
What about the conversations where you have no idea where
it's going to go. You don't know if they're even
willing to talk about it. How do you prepare for
something like that?
Speaker 3 (10:21):
I think.
Speaker 1 (10:24):
I have a friend who lost her dad. It's been
a few months, and every interaction that I have, I'm aware, Oh,
we're catching up and I want to know how she's
doing with grief.
Speaker 2 (10:39):
HM.
Speaker 1 (10:40):
But I don't want to be that friend who like,
every time we call, I'm like.
Speaker 3 (10:43):
How are you?
Speaker 1 (10:46):
You know, I've been close to enough people in grief
who know like, oh God, there's this weird currency to
getting updates on how I'm doing that people want in on,
And I don't want to be that friend.
Speaker 3 (10:59):
I want to be the friend who.
Speaker 1 (11:00):
Just like swims up to him and is like, what's
going on today? We can talk about the weather, we
can talk about whatever. We can talk about a menu.
Speaker 2 (11:09):
Or we can talk about your dad, or we talk
about how much nis him?
Speaker 1 (11:12):
Yeah, you know, So that's kind of that's like a
micro version of like how's this going to go? It's
kind of like when you know somebody's going through something.
But I don't want to be that friend who's like,
you know, how's it going?
Speaker 3 (11:25):
What are you dad? How's your heartbreak today?
Speaker 1 (11:27):
You know, there's other things where say there's like a
revelation where somebody is revealing something that's going to fundamentally
change the way the person you're telling understands the world
and their place in it. And I think with those
conversations if you can control the circumstances. It's to like
(11:48):
prepare yourself, prepare the person that there's going to be
sort of a different kind of can I talk to
you about something important? You know, you create a little
cocoon somehow for a different kind of conversation. I think
the best kind of planning for a hard conversation is,
like you plan for what you're going to say to
the person who's going to find out the thing, and
then you have consent circles outside of that of the
(12:10):
other people who know you're having the conversation, so you
can like debrief and get support from them so that
the initial reaction of the person isn't something that you
need to go a certain way because you just can't
control that.
Speaker 3 (12:24):
If somebody's finding out something.
Speaker 1 (12:26):
Fundamental about your relationship or something that hasn't been honest,
or if you're a manager who has to lay somebody off,
you can't go into that conversation expecting that they're going
to like appreciate hearing that information from you.
Speaker 2 (12:40):
Yeah, what about when when you're preparing for a conversation
where you might be on the receiving end of the revelation,
so you can tell someone's carrying something really heavy, and
your goal and the conversation is to create a space
where they could maybe feel comfortable opening up to you
about it.
Speaker 1 (12:57):
I think that the thing that I have learned from
talking to both people I love and I'm close to
in real life and people who are strangers as a
journalist about being that person that that someone is like
sharing something that they haven't shared before, is is it's
a huge compliment, but more like it is an immense responsibility,
(13:24):
because there's like, what is your first reaction? Are you
trying to lighten the mood and you laugh and it
could be construed as you laughing at them?
Speaker 3 (13:33):
Is it like.
Speaker 1 (13:36):
You don't know what to do with the information and
you feel like you want to offer some immediate, prescriptive
advice that's going to help make it feel less heavy,
And then that feels really pat and like you didn't
hear them. I've done all these things. By the way,
just be clear to all of these stings. You have
(13:56):
a responsibility to clarify with this person what the expectation
is about what you are going to do with this information,
how much it's kept confidential, who you might share it with,
and why, what you might do to help them, support them,
or advocate for them. You need their permission to do that.
I liked fashioning myself somebody who people would confide in.
(14:17):
That has long been part of my identity, And now
I almost feel rather than like going immediately into leaning in,
I keep the middle distance a little bit to make
sure I'm the right person, like recognizing your ability to
empathize and the limits of your ability to empathize. It's like,
am I the right person? And maybe I am the
(14:38):
right person, but I'm not the right person right now.
Like other mistakes I've made is not be clear about
my ability to show up. You know something about raising
young kids. As I've disappointed a lot of people and
let some friendships that were very like core to me.
They're a little bit dried up and need need watering
(15:01):
when I get more capacity. So I think that's the
other thing is making sure you're checking in and as
you can, and when you can't check in, figure out
how to like acknowledge that so that they don't feel abandoned.
Speaker 2 (15:16):
I'm so curious to know how having kids has shaped
how you think about difficult conversations. You're a mom to
two young children, and I imagine you don't engage with
them as you do with adults. So how have you
been navigating that space?
Speaker 3 (15:32):
It is profound.
Speaker 1 (15:35):
Something I think about a lot is restraint. I have daughters,
so there's like a mother daughter just like picture a
mother daughter trope. And in my version there's like the
way it expresses itself is I'm both the person that
(15:56):
they feel the most comfortable sort of falling apart with
after a long day of school. So they're the most
like Braddy to me of anybody in their lives.
Speaker 2 (16:05):
You're their safe space. Anna, That's what I always hear.
I had a friend and tell me recently, I don't
want to be my child's safe space anymore.
Speaker 3 (16:14):
Man, it's trying.
Speaker 1 (16:17):
So there's that, and then there's also when I really
want them to get something, and if I've had to
repeat it or if it's if it's something, the way
it shows up a lot is like if there's something
about interacting socially that feels very core to our values
as a family, whether it's how we talk to people
who're just meeting and manners, or how we just deal
(16:41):
with people who are different from us, Like your responsibility
as a parent is to teach this child how to
live in civilization. Right, the stakes are high, but kids
can only take in so much high minded instruction, so
like there's a certain point where you just get totally
tuned out. I think this is the same for whether
(17:03):
you're talking to a child or are grown up. We
all have our openings where we can hear, and we
have our times when we just like we're like, whatever,
what do I need to say to get this lady
to stop talking to me and move to my next thing?
And so I'm just I think being a parent has
made me much more aware about watching for your spots
and making sure you don't fill the space so that
(17:25):
them reflecting on something from the backseat of the car
when you're driving, you just like, don't talk over that
because you've got some lesson to impart. I love that kids'
timelines are different than grown ups. I mean, just imagine,
I'm like somebody who might I've built my professional life
around getting in there with people, and I'm gonna do
it with my kids. And like, you know what, Dinna,
(17:49):
you just got you gotta pace yourself.
Speaker 2 (17:56):
We'll be back in a moment with a slight change
of plans. What's your advice when you feel like a
(18:24):
difficult conversation needs to happen, but the other person does
not want to engage. So let's say there's a conflic
at work or with your partner and they're just not
having it. What do you do in a situation like that?
Speaker 1 (18:37):
You can't force somebody to engage in a way that
you want them to engage, And so then it's the
questions are if this person can't be with me in
this way that I want them to be and expect
them to be, and they're letting me down, can I
still have a relationship with them? Or do I want
(18:59):
to be around them? You know, and certainly an employer
employee relationship is lower stakes to move on from than
somebody in your family of origin, Like can you figure
out another way to be in relationship with them but
have things that you can't expect from each other?
Speaker 3 (19:16):
You know?
Speaker 1 (19:17):
If I feel like I need something from someone and
they are not giving it to me, what do I do?
That's a question about who you are, and you have
to sit with all those different possibilities that that could raise.
You know, I was married before, and in my first marriage,
any relationship has conflicts right and your earlier is like
(19:40):
part of getting to know each other. You discover the
ways that you're different, You discover the places where we
kind of misalign and have.
Speaker 3 (19:46):
To work at it.
Speaker 1 (19:48):
And then when a relationship you know that balance of
like we've lost so much of the connective tissue that
holds this together and I'm not giving you what you
need and You're not giving me what I need because
we want different things. You sort of knowed it. You
feel it's heaviness. You think about can I carry this around?
(20:09):
Is this going to change? Is this temporary or is
this forever? What does it mean about me that I
don't know how to have this relationship continue? If we
can't figure out this core hard conversation, Who am I?
If I'm somebody who doesn't want to stay in a marriage.
It's just like this kind of swamp you have to
(20:30):
trudge through to think, like what of this can I
tolerate and figure out how to live with? And how
much of this is so heavy and boggy that like,
I'm getting stuck in this mud.
Speaker 2 (20:43):
If the person is willing to engage, but you feel
like there's a moment in the conversation where they're starting
to close off. Do you have any advice for how
to help the walls go back down? Or do you
just kind of pivot? Do you take a break?
Speaker 1 (20:57):
I would try saying like, I noticed that you seems
like you're getting tired of this conversation. I notice that
you're sort of losing energy here. Do you want to
talk about this in another time? You know? Are you frustrated?
Are you angry? Like just kind of doing that thing
where you notice you make something that's unspoken or maybe
meta about the interaction and you make it explicit and
(21:18):
then see if it opens up and they might tell you, like,
you know, when you said that one word four sentences ago,
it really pissed me off, you know, and.
Speaker 3 (21:27):
You might not have been aware of it.
Speaker 1 (21:29):
Or it might be that you've talked for fifty minutes
and it's you know, eleven forty five pm, and it's
not the time to like come to a resolution. To
be continued can be okay, It can be really scary
for people who think of themselves as like I resolve
conflict to like sit with something that's unresolved.
Speaker 2 (21:50):
My worst night, Marianna, I can't even sleep well.
Speaker 1 (21:54):
I think that that's so interesting because I feel that
way too. And it's like something that my husband sometimes
says when we're like in the middle of some kind
of hard discussion. He'll be like, we're going to be okay,
but this really pisses me off when you do this.
It's just like so little, but just like it just says,
I'm not rejecting the whole idea of you as a
human person.
Speaker 3 (22:15):
Anna, you are not bad.
Speaker 2 (22:16):
Right now, and this relationship is not over.
Speaker 1 (22:19):
Yeah, because it gets to like our own feelings of
where we feel insecure and worthy, et cetera. So I
don't know, I think practicing sitting with unresolved conversations is
really powerful.
Speaker 2 (22:32):
I just felt that in my soul father way, and
I'm sorry to interrupt. I felt you were going to
say something else. I think that's so small it We'll
let it resonate in your soul a little bit.
Speaker 1 (22:41):
Ding.
Speaker 2 (22:43):
Yeah, that is what I personally need to practice. You
need to practice sitting in the discomfort of an unresolved conversation.
And I'm sure a lot of people who are listening
to this will resonate with that. We want closure. We're
desperate for closure and clarity and definitive answers, And so
(23:04):
when we don't get that on our timeline, when we
impose our timeline and someone else who is a very
different timeline and a very different level of patience and
tolerance for uncertainty or unresolved things, that's when we drive
ourselves crazy.
Speaker 1 (23:18):
Yeah. Well, it's a little bit like that gear that
I will go into at a dinner party. It's the
way I like to relate to somebody who's like driving
right to them. The other thing about that interaction is
I never feel out of control. I am like engaging
with somebody in the way that I want to engage
with them, and if they're giving it back to me,
we're like digging in.
Speaker 3 (23:38):
I don't feel out of control.
Speaker 1 (23:39):
I feel out of control when somebody is like I
don't want to engage with you in the way that
you're coming at me, it's.
Speaker 2 (23:45):
Like what, yes, okay, wait, tell me more about that. So,
like when you're doing the Anna version and they're not
having it, you can kind of feel like things are
going off the rails a little bit. Are there questions
or phrases or mechanisms you have to help pull yourself
back for a second and kind of recalibrate, like re engage.
Speaker 1 (24:04):
I mean, I think it's just, uh, I think it's
off putting me or it's surprising to me because it's
a it's an affront to my version of charm.
Speaker 3 (24:15):
You know.
Speaker 1 (24:16):
I'm like, this is how I work, and you're not
meeting me, and it makes me feel It'll make me
feel self conscious. It'll make me be like, oh God,
don't they see that I'm coming with good intentions and
I'm good, and I'm worthy, and I'm righteous and whatever,
Like I'm curious, I'm all the things that I was
taught to be in Unitarian.
Speaker 3 (24:34):
Church, you know what I mean.
Speaker 1 (24:38):
But the fact is, like I'm not in control. I
think of it in three D. It's three dimensional space.
It's not me being able to come at somebody and
have the kind of transaction I most want to have
to feel the most emotionally sort of secure and fed.
But like, if I can figure out how to be
next to them without needing them to like do the
(25:01):
thing in the way that I know how to do
it best, and I can be patient and humble, it
is a surrender of control. I guess, like Anna, you
have no idea what somebody is going through in a
certain day, even somebody you know really well, if it's
not clicking, you're going to think, oh, it's me, and
I want to figure out how to get back into click,
(25:22):
and I'm going to like force it.
Speaker 3 (25:23):
But sometimes it's just like not your day.
Speaker 2 (25:27):
You know, a lot of us, when we think about
approaching hard conversations, we focus so much on saying the
right thing. So in my head, I'm rehearsing throughout the
day exactly having to phrase this line and that line,
and what's my delivery going to be like, and anticipating
what they're going to say in response, and we forget
actually that one of the greatest tools at our disposal
is silence. It's just letting moments sit. You're the Queen
(25:52):
of observing silences, So tell me a bit more about that.
Speaker 1 (25:56):
It's a little bit like when you're talking with someone
and something has just happened, like you feel it happened
in a conversation, whether it's a sentence that sums up
something really big that you were sort of talking towards and.
Speaker 3 (26:09):
Then like oof.
Speaker 1 (26:12):
It's almost like when you don't rush in to just
tell them you understood, or you have another question or
like make them feel better when you just sit and
just let it. You know, it's kind of like throwing
a brock into a pond, like you just let it
have its moment. It's sort of a sign of reverence
or what has just been expressed.
Speaker 3 (26:34):
It also can be.
Speaker 1 (26:39):
Just like a you know, you're a musician, it's sort
of like arrest or almost like if it's a really
big thing, you're like, maybe we need to move to
the next movement. I'm gonna I want to just like
respect that something. This was something, So what I'll do.
(27:01):
I noticed my this isn't conscious, but I've noticed myself
over the years, like just sitting and I'll take a
deep breath in an interview set, and then unnoticed, the
person I'm interviewing will take a deep breath because they've
been sort of moving towards this saying, and then something
happens and then it's like, oh yeah, yeah. It's letting
something be big without having to be fixed or smoothed
(27:27):
over stand it over. I think often when people jump
in to fill gaps in silence, it's to indicate that
having an uncomfortable feeling is okay, and maybe there's this
other thing you know.
Speaker 3 (27:39):
Like have you talked with arapist?
Speaker 1 (27:40):
You know, like we want to say something that's going
to make it feel tolerable. And sometimes just big things
just need a little bit of air before you can
start thinking about what to do about them.
Speaker 2 (27:55):
For someone who's listening, who's mustered up the courage to
have that big, hard conversation, is there one final thought
you would leave them with, or some form of encouragement
or some wisdom from all of your years doing this
in your personal and professional life.
Speaker 1 (28:10):
I think if you're on the doorstep of a conversation
that makes you feel intimidated and nervous, just practice. It
might seem so dorky, but practicing really helps with someone
who knows you, with someone who can sit with you
and say, like, what's the most important objective you have
for this conversation? Is it to tell them this thing?
(28:34):
Is it to feel reconnected in this other way? Like,
we have a lot of different mixed objectives when we
have relational conversations, and there's sometimes at cross purposes, and
it can be so clarifying to just have an ally
who helps you figure out just that forest of feelings
(28:57):
so that you can feel confident that what you are
trying to express or bringing to the conversation is something
you've thought through and then you have that person to
come back or whether the conversation goes well or goes terribly,
Because these siks are not one and done like these
hard conversations. I think we talk about them as if
there's these discreet things. What hard conversations are in service
(29:21):
of is a relationship, and that is ongoing. And so
it's about that particular relationship where you haven't want to
talk about that thing, and then surrounding yourself with one
or as many relationships as you need to feel like
you've got back up to go into that scary thing.
Speaker 2 (30:01):
Hey, thanks so much for listening. If you enjoyed this episode,
please follow a slight change of plans wherever you listen
to podcasts and join me next time when we explore
what happens when the dream you've spent your whole life
chasing begins to hurt your well being.
Speaker 4 (30:16):
I almost saw myself as this piece of glass and
it got a crack, and you get up and you
try to put a little band aid on it. You
know that doesn't work, and then another crack, and another
and another, and then you kind of just wonder, at
what point is it just gonna shatter?
Speaker 2 (30:34):
That's next time on A Slight Change of Plans. A
Slight Change of Plans is created, written, and executive produced
by me Maya Schunker. The Slight Changed family includes our
showrunner Tyler Green, our senior editor Kate Parkinson Morgan, our
producers Britney Cronin and Megan Luvin, and our sound engineer
Erica Huang. Louis Scara wrote our delightful theme song, and
(30:58):
Ginger Smith helped arrange the vocals. A Slight Change of
Plans is a production of Pushkin Industries, so big thanks
to everyone there, and of course a very special thanks
to Jimmy. You can follow A Slight Change of Plans
on Instagram at doctor Maya Schunker. See you next week.
Pushkin hard conversations. I think we talk about them as
if there's these discreete things. What hard conversations are in
(00:35):
service of is a relationship and that is ongoing.
Speaker 2 (00:40):
Anna Sale is the creator and host of Death, Sex
and Money, a show that explores the big questions and
hard choices that are often left out of polite conversation.
She believes that sometimes the most powerful thing you can
say during a tough conversation is nothing at all.
Speaker 1 (00:58):
I think often when people jump in to fill gaps
in silence, it's to indicate that having an uncomfortable feeling
is okay.
Speaker 3 (01:06):
And maybe there's this other thing, you know, like, Hugh,
have you talked with arapist?
Speaker 1 (01:10):
You know, like we want to say something that's going
to make it feel tolerable, and sometimes big things just
need a little bit of air.
Speaker 2 (01:24):
On today's show, How to Have Hard Conversations, I'm Maya Schunker,
a scientist who studies human behavior, and this is a
slight change of plans, a show about who we are
and who we become in the face of a big change. Lately,
(01:49):
the world has been feeling super heavy, and it's made
me lose my appetite for hard conversations in my personal
life about even the small stuff. This worries me because
hard conversations are essential. They're how we process and work
through the challenges in our lives. Today's episode is a
gentle nudge to initiate those conversations that need to be
(02:11):
had and to bring our empathy, patience, and care to
these exchanges. Anna Sayle has spent her career leaning into
difficult topics, both on her podcast and for her book,
Let's Talk About Hard Things the life changing conversations that
connect us. In this episode, Anna reflects on what she's learned,
(02:32):
what's helped, what hasn't, and what she's still figuring out.
I wonder if you remember a time where you really
struggled to say something important to someone else, and what
was it about it that made it so hard.
Speaker 1 (02:46):
I have four sisters, So in any family, as you
get older, you realize that, like, the different siblings have
very different experiences in the family depending on how they
align with parents' expectations.
Speaker 2 (02:59):
Or I'm one of four, so you know, totally get it.
Speaker 1 (03:01):
Yeah, yeah, So I remember different sisters of mine at
different points in their lives. Teenagers call just would have
different responses to the way they talked about our parents
or whether they were felt like they had our parents' approval.
And I was a middle kid who did well in school,
and when I did things that were against the rules,
(03:23):
I never got caught. So like I just like slid through,
you know, I just like knew how to bob and
weave and didn't really have trouble with my parents and
other sisters of mine, like they had different responses to
confrontation and had different relationships with our parents. And so
I can remember those early conversations about, you know, try
and understand when something was upsetting them, and then also
(03:47):
having that parallel conversation or like desire to be protective
of how I saw our family and how I saw
our parents think it was too upsetting to let their
version of what their experience in our family had been
for me to sit with the conversation.
Speaker 2 (04:07):
Do you feel like you play a mediator role within
your own family, which is when you see that there's
some sort of strife, you try and actually facilitate an
open dialogue about it.
Speaker 1 (04:20):
Yes, And I think I would have more fully owned
that earlier in my life, because there's a way that
that fit with my idea of myself as super relationally
advanced and skillful. But there's this way that trying to
be in the middle and moderate and like help people
hear each other in ways that you think that they're
missing that that's like a power move that's kind of obnoxious. Like,
(04:47):
so when you step in to moderate something, you're becoming
the podcast host and the difficult relational piece in your family,
and not everybody wants you to play that role.
Speaker 2 (04:56):
Absolutely. I ask this because I am cut from the
same cloth. I don't know if it's a pathology around
peace seeking or the fact that my brain kind of
instinctively says, of course, a conversation would make this better.
But I feel such an impatience with silence and with
(05:16):
just pushing stuff under the rug that I feel like
a desperation in my life to expose everything, even if
it leads to a sense of calamity in the moment.
I think I just instinctively believe will be some sort
of payoff down the line.
Speaker 3 (05:32):
You so you're a disruptor, Yeah.
Speaker 2 (05:34):
Very disruptive, and often it works, but then sometimes it
makes things worse. And that is really a failure of
mine to empathize with a person who would prefer to
not talk about the thing I'm placing kind of a
norm on the other person, or I'm assuming they carry
my psychology.
Speaker 1 (05:54):
Yeah, and I totally get that impulse, especially when it's
like among people you really love and you want you
want it to get on with it. Let's just like
get on with it and move to a new way
of understanding each other. I mean, I wrote a book.
I wrote a benmore. I had a whole chapter about family.
I was like sharing drafts with all my family members.
Speaker 3 (06:15):
How's this read to you? How's this read to you?
Speaker 4 (06:17):
So?
Speaker 1 (06:18):
I think I was definitely playing that role when I
was doing that, and then it was kind of like, Okay,
I've done that.
Speaker 3 (06:25):
We're just going to like step.
Speaker 1 (06:26):
Back and let everybody have their own experience in the
family and sort of be a member of it and
observe and realize that this is an organism that has
a lot of different stuff going on.
Speaker 2 (06:37):
Yeah, so zooming out a little bit. I mean, you've
obviously made a career around having difficult conversations with people.
How do you prepare for a hard conversation with someone
with your family, with your husband, with friends. Yeah.
Speaker 1 (06:54):
When I think of hard conversations now. They don't happen
during podcast recordings. They happen with my husband, they happen
with my closest friends, because those are the ones where
there's stakes and where it hurts if you feel like
your intentions are not sort of seen clearly, or that
(07:14):
I'm missing something that's that I'm doing, that's really hurtful.
So I think that the way that I try to
prepare is I can feel it in my body when
I get seized up with sort of like I get
something to got to bring up, you know, I'm feeling wronged,
you know, And often it's something around feeling overwhelmed or
(07:36):
like some way that I've tried really hard hasn't been
sufficiently acknowledged and I'm worn out, and it's really hard
not to just start the conversation right in that, you know,
like pissed off way, Yeah.
Speaker 2 (07:51):
Like you don't appreciate that I'm doing the dishes every night.
Speaker 1 (07:53):
Yeah, And that doesn't always go well. It's like how
do I slow down and take a breath, And then
after I sort of can breathe a minute, I have
just a little bit more space around the emotion of
(08:13):
it that I can like be a little bit more
in control of how I respond, because when I don't
take that minute, it's just if you're pissed, you've got
something to say, it doesn't land well, and then you're
feeling like you're having to defend yourself. Then it's just
like tight self protection defensive Anna, She's just going to
(08:36):
be present in protecting herself until she gets tired.
Speaker 3 (08:40):
Then you can finally resolve.
Speaker 2 (08:42):
And I'm assuming you lack receptivity to what other person's saying,
so nothing other than Anna, you are totally right.
Speaker 3 (08:50):
Oh my god, And how could I not have seen?
Speaker 2 (08:53):
And I think to myself every day how lucky I
am that you were willing to marry me and that
you do do the dishes.
Speaker 3 (08:58):
My god, Maya, maybe we should get married.
Speaker 2 (09:01):
I know, I think so. So I think we can
all imagine pretty clearly what the pissed off version looks like,
Oh my god, you never appreciate me. What is the
more like, take a deep breath, slightly more reflective version
of that conversation? Look like?
Speaker 1 (09:17):
What I try to do is just starting that conversation
with like, Okay, can we back up and talk about
how we hope this thing goes?
Speaker 3 (09:25):
What do you hope for it? What do I hope
for it?
Speaker 1 (09:27):
It's trying to get to that place where you have
the spirit of Okay, I am doing the best I can,
and this person I have conflict with right now is
doing the best he can? And how do I not lash?
And like lash out is a good word, because like,
my kids are elementary school age, and I can see
when I lose my patience and I get a little
(09:49):
like snippy, it almost goes down like a little ladder.
I get snippy about something, getting get your shoes on,
get in the car, And then I can watch my
nine year old get snippy with my six year old,
and it's just like, oh, this isn't about some like
fundamental you know, misalignment and chores in this house. This
is like I felt bad, I madebody else feel bad.
(10:09):
They made somebody else feel bad.
Speaker 2 (10:11):
What about the conversations where you have no idea where
it's going to go. You don't know if they're even
willing to talk about it. How do you prepare for
something like that?
Speaker 3 (10:21):
I think.
Speaker 1 (10:24):
I have a friend who lost her dad. It's been
a few months, and every interaction that I have, I'm aware, Oh,
we're catching up and I want to know how she's
doing with grief.
Speaker 2 (10:39):
HM.
Speaker 1 (10:40):
But I don't want to be that friend who like,
every time we call, I'm like.
Speaker 3 (10:43):
How are you?
Speaker 1 (10:46):
You know, I've been close to enough people in grief
who know like, oh God, there's this weird currency to
getting updates on how I'm doing that people want in on,
And I don't want to be that friend.
Speaker 3 (10:59):
I want to be the friend who.
Speaker 1 (11:00):
Just like swims up to him and is like, what's
going on today? We can talk about the weather, we
can talk about whatever. We can talk about a menu.
Speaker 2 (11:09):
Or we can talk about your dad, or we talk
about how much nis him?
Speaker 1 (11:12):
Yeah, you know, So that's kind of that's like a
micro version of like how's this going to go? It's
kind of like when you know somebody's going through something.
But I don't want to be that friend who's like,
you know, how's it going?
Speaker 3 (11:25):
What are you dad? How's your heartbreak today?
Speaker 1 (11:27):
You know, there's other things where say there's like a
revelation where somebody is revealing something that's going to fundamentally
change the way the person you're telling understands the world
and their place in it. And I think with those
conversations if you can control the circumstances. It's to like
(11:48):
prepare yourself, prepare the person that there's going to be
sort of a different kind of can I talk to
you about something important? You know, you create a little
cocoon somehow for a different kind of conversation. I think
the best kind of planning for a hard conversation is,
like you plan for what you're going to say to
the person who's going to find out the thing, and
then you have consent circles outside of that of the
(12:10):
other people who know you're having the conversation, so you
can like debrief and get support from them so that
the initial reaction of the person isn't something that you
need to go a certain way because you just can't
control that.
Speaker 3 (12:24):
If somebody's finding out something.
Speaker 1 (12:26):
Fundamental about your relationship or something that hasn't been honest,
or if you're a manager who has to lay somebody off,
you can't go into that conversation expecting that they're going
to like appreciate hearing that information from you.
Speaker 2 (12:40):
Yeah, what about when when you're preparing for a conversation
where you might be on the receiving end of the revelation,
so you can tell someone's carrying something really heavy, and
your goal and the conversation is to create a space
where they could maybe feel comfortable opening up to you
about it.
Speaker 1 (12:57):
I think that the thing that I have learned from
talking to both people I love and I'm close to
in real life and people who are strangers as a
journalist about being that person that that someone is like
sharing something that they haven't shared before, is is it's
a huge compliment, but more like it is an immense responsibility,
(13:24):
because there's like, what is your first reaction? Are you
trying to lighten the mood and you laugh and it
could be construed as you laughing at them?
Speaker 3 (13:33):
Is it like.
Speaker 1 (13:36):
You don't know what to do with the information and
you feel like you want to offer some immediate, prescriptive
advice that's going to help make it feel less heavy,
And then that feels really pat and like you didn't
hear them. I've done all these things. By the way,
just be clear to all of these stings. You have
(13:56):
a responsibility to clarify with this person what the expectation
is about what you are going to do with this information,
how much it's kept confidential, who you might share it with,
and why, what you might do to help them, support them,
or advocate for them. You need their permission to do that.
I liked fashioning myself somebody who people would confide in.
(14:17):
That has long been part of my identity, And now
I almost feel rather than like going immediately into leaning in,
I keep the middle distance a little bit to make
sure I'm the right person, like recognizing your ability to
empathize and the limits of your ability to empathize. It's like,
am I the right person? And maybe I am the
(14:38):
right person, but I'm not the right person right now.
Like other mistakes I've made is not be clear about
my ability to show up. You know something about raising
young kids. As I've disappointed a lot of people and
let some friendships that were very like core to me.
They're a little bit dried up and need need watering
(15:01):
when I get more capacity. So I think that's the
other thing is making sure you're checking in and as
you can, and when you can't check in, figure out
how to like acknowledge that so that they don't feel abandoned.
Speaker 2 (15:16):
I'm so curious to know how having kids has shaped
how you think about difficult conversations. You're a mom to
two young children, and I imagine you don't engage with
them as you do with adults. So how have you
been navigating that space?
Speaker 3 (15:32):
It is profound.
Speaker 1 (15:35):
Something I think about a lot is restraint. I have daughters,
so there's like a mother daughter just like picture a
mother daughter trope. And in my version there's like the
way it expresses itself is I'm both the person that
(15:56):
they feel the most comfortable sort of falling apart with
after a long day of school. So they're the most
like Braddy to me of anybody in their lives.
Speaker 2 (16:05):
You're their safe space. Anna, That's what I always hear.
I had a friend and tell me recently, I don't
want to be my child's safe space anymore.
Speaker 3 (16:14):
Man, it's trying.
Speaker 1 (16:17):
So there's that, and then there's also when I really
want them to get something, and if I've had to
repeat it or if it's if it's something, the way
it shows up a lot is like if there's something
about interacting socially that feels very core to our values
as a family, whether it's how we talk to people
who're just meeting and manners, or how we just deal
(16:41):
with people who are different from us, Like your responsibility
as a parent is to teach this child how to
live in civilization. Right, the stakes are high, but kids
can only take in so much high minded instruction, so
like there's a certain point where you just get totally
tuned out. I think this is the same for whether
(17:03):
you're talking to a child or are grown up. We
all have our openings where we can hear, and we
have our times when we just like we're like, whatever,
what do I need to say to get this lady
to stop talking to me and move to my next thing?
And so I'm just I think being a parent has
made me much more aware about watching for your spots
and making sure you don't fill the space so that
(17:25):
them reflecting on something from the backseat of the car
when you're driving, you just like, don't talk over that
because you've got some lesson to impart. I love that kids'
timelines are different than grown ups. I mean, just imagine,
I'm like somebody who might I've built my professional life
around getting in there with people, and I'm gonna do
it with my kids. And like, you know what, Dinna,
(17:49):
you just got you gotta pace yourself.
Speaker 2 (17:56):
We'll be back in a moment with a slight change
of plans. What's your advice when you feel like a
(18:24):
difficult conversation needs to happen, but the other person does
not want to engage. So let's say there's a conflic
at work or with your partner and they're just not
having it. What do you do in a situation like that?
Speaker 1 (18:37):
You can't force somebody to engage in a way that
you want them to engage, And so then it's the
questions are if this person can't be with me in
this way that I want them to be and expect
them to be, and they're letting me down, can I
still have a relationship with them? Or do I want
(18:59):
to be around them? You know, and certainly an employer
employee relationship is lower stakes to move on from than
somebody in your family of origin, Like can you figure
out another way to be in relationship with them but
have things that you can't expect from each other?
Speaker 3 (19:16):
You know?
Speaker 1 (19:17):
If I feel like I need something from someone and
they are not giving it to me, what do I do?
That's a question about who you are, and you have
to sit with all those different possibilities that that could raise.
You know, I was married before, and in my first marriage,
any relationship has conflicts right and your earlier is like
(19:40):
part of getting to know each other. You discover the
ways that you're different, You discover the places where we
kind of misalign and have.
Speaker 3 (19:46):
To work at it.
Speaker 1 (19:48):
And then when a relationship you know that balance of
like we've lost so much of the connective tissue that
holds this together and I'm not giving you what you
need and You're not giving me what I need because
we want different things. You sort of knowed it. You
feel it's heaviness. You think about can I carry this around?
(20:09):
Is this going to change? Is this temporary or is
this forever? What does it mean about me that I
don't know how to have this relationship continue? If we
can't figure out this core hard conversation, Who am I?
If I'm somebody who doesn't want to stay in a marriage.
It's just like this kind of swamp you have to
(20:30):
trudge through to think, like what of this can I
tolerate and figure out how to live with? And how
much of this is so heavy and boggy that like,
I'm getting stuck in this mud.
Speaker 2 (20:43):
If the person is willing to engage, but you feel
like there's a moment in the conversation where they're starting
to close off. Do you have any advice for how
to help the walls go back down? Or do you
just kind of pivot? Do you take a break?
Speaker 1 (20:57):
I would try saying like, I noticed that you seems
like you're getting tired of this conversation. I notice that
you're sort of losing energy here. Do you want to
talk about this in another time? You know? Are you frustrated?
Are you angry? Like just kind of doing that thing
where you notice you make something that's unspoken or maybe
meta about the interaction and you make it explicit and
(21:18):
then see if it opens up and they might tell you, like,
you know, when you said that one word four sentences ago,
it really pissed me off, you know, and.
Speaker 3 (21:27):
You might not have been aware of it.
Speaker 1 (21:29):
Or it might be that you've talked for fifty minutes
and it's you know, eleven forty five pm, and it's
not the time to like come to a resolution. To
be continued can be okay, It can be really scary
for people who think of themselves as like I resolve
conflict to like sit with something that's unresolved.
Speaker 2 (21:50):
My worst night, Marianna, I can't even sleep well.
Speaker 1 (21:54):
I think that that's so interesting because I feel that
way too. And it's like something that my husband sometimes
says when we're like in the middle of some kind
of hard discussion. He'll be like, we're going to be okay,
but this really pisses me off when you do this.
It's just like so little, but just like it just says,
I'm not rejecting the whole idea of you as a
human person.
Speaker 3 (22:15):
Anna, you are not bad.
Speaker 2 (22:16):
Right now, and this relationship is not over.
Speaker 1 (22:19):
Yeah, because it gets to like our own feelings of
where we feel insecure and worthy, et cetera. So I
don't know, I think practicing sitting with unresolved conversations is
really powerful.
Speaker 2 (22:32):
I just felt that in my soul father way, and
I'm sorry to interrupt. I felt you were going to
say something else. I think that's so small it We'll
let it resonate in your soul a little bit.
Speaker 1 (22:41):
Ding.
Speaker 2 (22:43):
Yeah, that is what I personally need to practice. You
need to practice sitting in the discomfort of an unresolved conversation.
And I'm sure a lot of people who are listening
to this will resonate with that. We want closure. We're
desperate for closure and clarity and definitive answers, And so
(23:04):
when we don't get that on our timeline, when we
impose our timeline and someone else who is a very
different timeline and a very different level of patience and
tolerance for uncertainty or unresolved things, that's when we drive
ourselves crazy.
Speaker 1 (23:18):
Yeah. Well, it's a little bit like that gear that
I will go into at a dinner party. It's the
way I like to relate to somebody who's like driving
right to them. The other thing about that interaction is
I never feel out of control. I am like engaging
with somebody in the way that I want to engage
with them, and if they're giving it back to me,
we're like digging in.
Speaker 3 (23:38):
I don't feel out of control.
Speaker 1 (23:39):
I feel out of control when somebody is like I
don't want to engage with you in the way that
you're coming at me, it's.
Speaker 2 (23:45):
Like what, yes, okay, wait, tell me more about that. So,
like when you're doing the Anna version and they're not
having it, you can kind of feel like things are
going off the rails a little bit. Are there questions
or phrases or mechanisms you have to help pull yourself
back for a second and kind of recalibrate, like re engage.
Speaker 1 (24:04):
I mean, I think it's just, uh, I think it's
off putting me or it's surprising to me because it's
a it's an affront to my version of charm.
Speaker 3 (24:15):
You know.
Speaker 1 (24:16):
I'm like, this is how I work, and you're not
meeting me, and it makes me feel It'll make me
feel self conscious. It'll make me be like, oh God,
don't they see that I'm coming with good intentions and
I'm good, and I'm worthy, and I'm righteous and whatever,
Like I'm curious, I'm all the things that I was
taught to be in Unitarian.
Speaker 3 (24:34):
Church, you know what I mean.
Speaker 1 (24:38):
But the fact is, like I'm not in control. I
think of it in three D. It's three dimensional space.
It's not me being able to come at somebody and
have the kind of transaction I most want to have
to feel the most emotionally sort of secure and fed.
But like, if I can figure out how to be
next to them without needing them to like do the
(25:01):
thing in the way that I know how to do
it best, and I can be patient and humble, it
is a surrender of control. I guess, like Anna, you
have no idea what somebody is going through in a
certain day, even somebody you know really well, if it's
not clicking, you're going to think, oh, it's me, and
I want to figure out how to get back into click,
(25:22):
and I'm going to like force it.
Speaker 3 (25:23):
But sometimes it's just like not your day.
Speaker 2 (25:27):
You know, a lot of us, when we think about
approaching hard conversations, we focus so much on saying the
right thing. So in my head, I'm rehearsing throughout the
day exactly having to phrase this line and that line,
and what's my delivery going to be like, and anticipating
what they're going to say in response, and we forget
actually that one of the greatest tools at our disposal
is silence. It's just letting moments sit. You're the Queen
(25:52):
of observing silences, So tell me a bit more about that.
Speaker 1 (25:56):
It's a little bit like when you're talking with someone
and something has just happened, like you feel it happened
in a conversation, whether it's a sentence that sums up
something really big that you were sort of talking towards and.
Speaker 3 (26:09):
Then like oof.
Speaker 1 (26:12):
It's almost like when you don't rush in to just
tell them you understood, or you have another question or
like make them feel better when you just sit and
just let it. You know, it's kind of like throwing
a brock into a pond, like you just let it
have its moment. It's sort of a sign of reverence
or what has just been expressed.
Speaker 3 (26:34):
It also can be.
Speaker 1 (26:39):
Just like a you know, you're a musician, it's sort
of like arrest or almost like if it's a really
big thing, you're like, maybe we need to move to
the next movement. I'm gonna I want to just like
respect that something. This was something, So what I'll do.
(27:01):
I noticed my this isn't conscious, but I've noticed myself
over the years, like just sitting and I'll take a
deep breath in an interview set, and then unnoticed, the
person I'm interviewing will take a deep breath because they've
been sort of moving towards this saying, and then something
happens and then it's like, oh yeah, yeah. It's letting
something be big without having to be fixed or smoothed
(27:27):
over stand it over. I think often when people jump
in to fill gaps in silence, it's to indicate that
having an uncomfortable feeling is okay, and maybe there's this
other thing you know.
Speaker 3 (27:39):
Like have you talked with arapist?
Speaker 1 (27:40):
You know, like we want to say something that's going
to make it feel tolerable. And sometimes just big things
just need a little bit of air before you can
start thinking about what to do about them.
Speaker 2 (27:55):
For someone who's listening, who's mustered up the courage to
have that big, hard conversation, is there one final thought
you would leave them with, or some form of encouragement
or some wisdom from all of your years doing this
in your personal and professional life.
Speaker 1 (28:10):
I think if you're on the doorstep of a conversation
that makes you feel intimidated and nervous, just practice. It
might seem so dorky, but practicing really helps with someone
who knows you, with someone who can sit with you
and say, like, what's the most important objective you have
for this conversation? Is it to tell them this thing?
(28:34):
Is it to feel reconnected in this other way? Like,
we have a lot of different mixed objectives when we
have relational conversations, and there's sometimes at cross purposes, and
it can be so clarifying to just have an ally
who helps you figure out just that forest of feelings
(28:57):
so that you can feel confident that what you are
trying to express or bringing to the conversation is something
you've thought through and then you have that person to
come back or whether the conversation goes well or goes terribly,
Because these siks are not one and done like these
hard conversations. I think we talk about them as if
there's these discreet things. What hard conversations are in service
(29:21):
of is a relationship, and that is ongoing. And so
it's about that particular relationship where you haven't want to
talk about that thing, and then surrounding yourself with one
or as many relationships as you need to feel like
you've got back up to go into that scary thing.
Speaker 2 (30:01):
Hey, thanks so much for listening. If you enjoyed this episode,
please follow a slight change of plans wherever you listen
to podcasts and join me next time when we explore
what happens when the dream you've spent your whole life
chasing begins to hurt your well being.
Speaker 4 (30:16):
I almost saw myself as this piece of glass and
it got a crack, and you get up and you
try to put a little band aid on it. You
know that doesn't work, and then another crack, and another
and another, and then you kind of just wonder, at
what point is it just gonna shatter?
Speaker 2 (30:34):
That's next time on A Slight Change of Plans. A
Slight Change of Plans is created, written, and executive produced
by me Maya Schunker. The Slight Changed family includes our
showrunner Tyler Green, our senior editor Kate Parkinson Morgan, our
producers Britney Cronin and Megan Luvin, and our sound engineer
Erica Huang. Louis Scara wrote our delightful theme song, and
(30:58):
Ginger Smith helped arrange the vocals. A Slight Change of
Plans is a production of Pushkin Industries, so big thanks
to everyone there, and of course a very special thanks
to Jimmy. You can follow A Slight Change of Plans
on Instagram at doctor Maya Schunker. See you next week.
Host
Dr. Maya Shankar
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