Ep #227: Why Tough Topics Are Hard to Talk About: An Interview with Anna Sale

The Widowed Mom Podcast Krista St-Germain | Why Tough Topics Are Hard to Talk About: An Interview with Anna Sale

There’s often a disconnect between stories of loss and the physical manifestation of it for the people experiencing it.

Anna Sale is an interviewer and the host of the award-winning podcast, Death, Sex & Money, where she has mastered the art of listening and offering space for being listened to when we go through hard things.

Join us on this episode as Anna offers what she has learned from all the interviews she has conducted on tough topics that are hard to talk about, and how we can make these conversations easier.


Listen to the Full Episode:


If you want to create a future you can truly get excited about even after the loss of your spouse, I invite you to apply for Mom Goes On.


What You’ll Learn from this Episode:

  • What motivated Anna to create a podcast where she talks about tough topics.
  • Why it’s often hard to talk about messy or taboo topics.
  • How Anna’s perception of grief and grieving has shifted over time.


Featured on the Show:


Full Episode Transcript:

Welcome to The Widowed Mom Podcast, episode 227, Why Tough Topics Are Hard to Talk About: An Interview with Anna Sale.

Welcome to The Widowed Mom Podcast, the only podcast that offers a proven process to help you work through your grief, to grow, evolve, and create a future you can truly look forward to. Here’s your host, Master Certified life coach, grief expert, widow, and mom, Krista St-Germain.

Before we jump into today’s podcast, I want you to check out this message from one of my Mom Goes On members. Here it is.

Hi, my name is Pam and I would like to invite you to join Mom Goes On like I did one year ago. This amazing program has totally shifted my life as a widow experiencing prolonged grief. I found Krista’s podcast and connected right away because it seemed like this was the first time in six years as a widow that someone really understood me and all I was going through.

Along with Krista’s guidance and coaching, the program has taught me skills that will be valuable to me the rest of my life and that have helped me move forward with my life in positive ways which I could not have imagined one year ago. Come join us in Mom Goes On for an experience that is sure to change your life in numerous ways.

Hey there, welcome to another episode of the podcast. What’s going on in your world? How are you doing? Fall is here, you know, that means I’m excited. Also I told you I’d share what I’m getting joy from these days. Something I recently got a lot of joy from and anticipate joy for years to come from was that my daughter decided to go through recruitment as a sophomore and joined Delta Gamma, which is my sorority. I am a proud Delta Gamma alum. I never honestly imagined that I would be in a sorority.

I wasn’t interested at all when I first was given the opportunity but later decided to join after having a fairly boring first semester on campus and also getting to know some women and realizing that the stereotypes I had in my mind were not actually what it was like. Turns out that was one of the best decisions I ever made. Delta Gamma gave me, honestly, just such a great experience, such a safe place for me to learn to lead and to communicate and to have hard conversations with people, to learn to be a champion for someone who maybe I didn’t see eye to eye with.

And of course, if you’ve listened to the podcast for a while, you probably know, but the whole reason Heather’s Camp was started was because my sister, Heather Muller, died, and we wanted to do something in her memory. And so we created Heather’s Camp, which is a camp for kids who are blind or visually impaired. And we have been doing that camp for about 20 years when the accident happened that killed my husband. So we were coming back from Heather’s Camp and that was when the accident happened.

So suffice it to say that the women who have experienced the highest of highs in my life and absolutely the lowest of lows, the ones who really rallied around me were my sisters, they were delta gammas. And so that connection means a lot to me. I have been singing delta gamma songs to my daughter since she was in the womb. So I realized after watching her go through this process, I didn’t think she was interested in it, honestly, and she decided she was and she kept an open mind and went through it.

And wow, I didn’t realize how biased I was until I watched her go through that process. It was so hard for me to tell her to follow her heart. When I just really wanted to say, “Join Delta Gamma, there can be no other.” But it was really cool to be part of the process and to watch her go through it, to be there. I got to watch the preference night ceremony. As soon as they started singing one of the songs which I used to sing to her as a baby, she just burst into tears, which made me burst into tears.

And it was a whole emotional thing that I just did not anticipate but then really cool to be there for her bid day and her pinning ceremony and just experience this through her eyes again. It’s brought back so many amazing memories that I have had, not just of college, but of all the things that I have had the pleasure of experiencing and the person who I have grown into because of my membership, really, really cool for me. so lots of joy from that.

I look forward to watching her go through the new member process and seeing what she contributes to the chapter and what she gets out of it. Just so, so fun for me. So that’s what’s bringing me joy these days and of course, I mean fall, fall you all, always brings me joy, so my favorite season bar none.

Alright, here’s what I have for you this week, you may have never heard of Anna Sale. But she is the host of an award winning podcast called Death, Sex and Money. And I was lucky enough to interview her on today’s episode of the podcast. The reason I wanted to talk with Anna and the reason I think that it’s valuable for you is because we are in positions as widows to talk about really hard things all the time. And that’s what Anna does on her podcast is she talks about things that are hard for people to talk about.

And so I hope you enjoy this conversation and learn a little bit from her on what she has learned from all the interviews that she’s done about why things can be so hard to talk about and how to make them easier. So with that I will let you listen to my interview with the amazing Anna Sale.

Krista: Alright, welcome, Anna to the podcast. I’m delighted that I have found another human who wants to come and talk about hard things so thank you for being here.

Anna: Thank you very much for having me.

Krista: Yeah. Why don’t you just start and just tell our listeners a little bit about you, what you do, who you are.

Anna: Yeah. I am an interviewer. I work in public radio and for almost 10 years now I’ve hosted a show called Death, Sex and Money which when we started it in 2014, the intention was pretty simple, which was let’s create a space where we’re going to talk about these things that can be hard to talk about, can be isolating, can feel stigmatized. And try to bring a spirit of curiosity and swapping stories so that we all feel like we have a little bit more company as we go through these hard things in life that also affect each and every one of us despite how alone we can feel.

Krista: Yeah. What was the impetus for wanting to have conversations about hard things on a podcast?

Anna: It kind of was a weird origin story. I covered politics before that and I found that when I would go to strip malls and parks and talk to voters about how do you think things are going in the country? The tape that I would often use in stories was about who they were going to vote for but what they really wanted to tell me was about some big stuff that was going on in their lives. And it was affecting whether they felt like things were going in the right direction or the wrong direction. And then I would be interviewing politicians.

And there was just a lot of talking about things in a sort of performative way that didn’t feel totally authentic. And so it was kind of a reaction to that, let’s actually talk about this stuff, let’s actually. I wanted to flip it so rather than getting to know a voter so I could do a story about who they were going to vote for. I wanted to just do a story about a person who was telling me something about their life that was affecting something big. So that was kind of intellectually the idea.

And then in my own personal life I had, I was in my early 30s, my first marriage ended, I got divorced. I was very sort of in one of those moments where you feel like gravity is suspended and all of a sudden you just don’t know, that yearn for feeling grounded again and not knowing the next step to take. And I just wanted to talk with people about how they had encountered those moments in life and what they had done next and what was helpful to them.

And so it was that combination of kind of feeling like I was interested in people’s stories, so I think other people would want to listen in and really need to get personally. And I don’t think I appreciated, and you know this as a podcast host, the thing that’s really special about this medium is you are creating these very intimate clubhouses where you are reaching people in their most kind of solitary time. Maybe it’s on a treadmill, maybe it’s folding laundry, maybe it’s on a walk.

But I think the medium itself is really conducive to digging into stuff that maybe at other times you might flip that page in the newspaper. But the podcast is when you’re ready to slow down, I think and dig in.

Krista: Yeah, and maybe looking for connection too. You described that so well. I think probably everyone that’s listening right now in my audience specifically would really relate to that suspended gravity and wanting to feel grounded and not really knowing. I mean I think my listeners, most of them feel that way because they lost their person and so of course it makes total sense but it can be a surprise how ungrounded one can feel in that.

Anna: And I remember feeling kind of surprised, but I have this visual of feeling like a helium balloon that just could not stay in this terror of not feeling in control. I was just subject to the whims of wind and that didn’t feel freeing. That felt terrifying for me. So I was like, “I need some scaffolding.” And the quickest way to create scaffolding I found was just somebody tell me they understand one little piece of what I’m experiencing, so I at least have a relationship to hold onto for just a few minutes even.

Krista: Yeah, my visual was, what’s that commercial? It was like, was it a Robitussin commercial or maybe it’s a Dayquil commercial where the person’s head is floating off like a balloon. That was how it felt to me. I felt like I kept trying to grab myself and pull myself back down, it’s like, yeah, yeah. So your podcast is called Death, Sex and Money.

I find whenever I, I mean always we’re talking about death because I work with widows specifically. But whenever I talk about sex and money, those are always the most downloaded podcast episodes, so I can only imagine the combination of all three. Do you have one that has been particularly more insightful or enjoyable or worthwhile to you than another?

Anna: I think they’re all so interesting. I mean, the sex episodes, when it’s an episode where we’re really getting into something, whether it’s experimenting with different relationship forms or different ways that people have formed relationships, things about paid sex work. That’s always very interesting to me because it feels like it’s a window into lots of different ways of experiencing intimacy.

And money is interesting to me because it’s so much in a black box all the time, even though we’re always dealing with money. Every three hours of our lives we’re doing something financial and still it’s this energy that is ever present but never discussed. So I think that I’m just magnetized to that, any simple question about it can be so illuminating.

But I do think the episodes where I have talked with people who have experienced profound loss. Those are the ones that I find myself, it’s kind of like they’re handles that I will reach for when something in my life is going on just to remind me of, I don’t know, the big structure that we’re all doing this within, which is that we’re all headed for an end, each of us. Most of us experience a profound loss of someone before we get there ourselves.

And I am very interested within we can talk about it, we can share about it. And also the way that that disconnect between stories around loss and then the physical manifestation of it and how people who are in say their first year of having lost someone very close to them, it’s kind of un-narratable in a way. What I like to really acknowledge with profound grief is it’s we so want to wrap an arc around it as a way of kind of containing it. And that is so impossible.

And I like giving space for that idea that you might in one moment be breaking down as you’re thinking about the loss of your husband. And then 30 minutes later, you might be so annoyed at the neighbor who’s checking in on you again and wanting to see if you need dinner because you just want to be left alone. The mix of anger and unappealing-ness and also profound loss and needing care is, I think, just really rich and not shared enough because it’s messy.

Krista: Yeah. So obviously, since you have had a lot of hard conversations with people, why do you think conversations around the messier subjects or the more taboo subjects are so hard for people?

Anna: I would be interested in what you have experienced as an interviewer. I have found if someone has gone through profound loss, it’s not so much that it’s so hard for them to talk about. It’s hard for everybody to kind of get clear on what the expectations are about how much we’re getting into this. Or managing that feeling of, oh my God, I don’t want to end having shared this with you having to comfort you in some backwards way.

And so I think maybe it’s harder for the listener to figure out how to listen and tolerate what comes up for them than it is for someone to talk about it.

Krista: Yeah. I kind of find it varies based on, at least it has for me with where I am in my own peace around the topic. So, early in the days when my husband died, it wasn’t an easy thing to talk about. And later it became easier, not really because time passed, but because I was able to think consciously about it and kind of reconcile it for myself. But something like money, even as it related to his death, I felt way more comfortable with his death before I ever felt comfortable talking about money as it related to his death.

So it just kind of follows that trajectory for me anyway of, I’ve got to do my own work first and make my own peace with whatever it is. And then it doesn’t feel so weird for me to talk about it. And sometimes talking about it is part of making peace with it. But until I actually investigate whatever it is that’s holding me back in that one area, yeah, it’s hard to talk about, is internal judgment happening?

Anna: Yeah. And there’s certainly maybe it’s easier to talk with this one person in this one moment in your life because they get this one piece of it. But then, oh, my God, do I have to talk about this at drop off when I’m getting my kid to the first day of school? How do I get out of this weird social encounter, this ought to be pretty surface but how do I explain?

Krista: The million times people say, “Oh, you’re so strong.” And you just want to punch them in the throat.

Anna: The throat.

Krista: I mean, you know why they say it and you get it but also you just, you get so tired of hearing it, you don’t want to hear it anymore, when you don’t feel that way. When you don’t feel strong, you don’t want to be told that you are. So I know you’ve interviewed a lot of widows, what have you taken away from those interviews, what have you learned?

Anna: It’s so varied. There’ll be some moments, I’m married now and one that comes to mind, an interview, I interviewed the writer, Leslie Gray Streeter. And her husband died suddenly of some kind of cardiac event in the middle of the night. And when I say a death episode that flashes back to me, that’s one that I think about because sometimes I’ll look over at my husband and it’ll be just this reminder of this is not forever. This is not guaranteed this moment. And so I think of moments like that.

I also think of older women I’ve interviewed where there were complicated marriages, some that ended in divorce, some that were just complicated, not always easy marriages. And that mix of profound loss was also creating a lot of new space that didn’t exist before. I think it’s really interesting to hear women talk about, certainly women who came of age maybe before the mid-70s and for whom this is a really new feeling, I think it’s interesting to talk to people at various stages after.

I think often people are telling their widowhood stories maybe in the first few years. But I like hearing people talk about just the way it’s an alive process, the grief. And how three years after there was really intense fury at not getting to have a good death, whatever that is, because the husband couldn’t tolerate the fact that it was happening. And then how years after that, that fury has shifted into something else and the death experience is less of what is top of mind when the husband comes up in conversation.

So it’s really varied. I’m so interested in relationships and intimate companionship. And I think that people who have known that and then who have lost that, just I’m just interested in the different, the terrain of it. So I don’t think there’s a certain set of things that I’ve learned from widows. It’s more like what’s this been like for you? Tell me what.

Krista: Yeah, because it’s all so different. Yeah, I think it’s like you said before, we want there to be this arc of maybe hope and similarity and hope in a process or hope in stages. And then when you dig into it, you find out that that’s not what it’s like for most people. It’s kind of all over the place.

So when my husband died, one of the things that bothered me the most in retrospect, was that I really felt pretty unprepared for grief. I didn’t really know what I didn’t know and the only thing I knew was the five stages. I was kind of like, I’m going to get the grief A plus. So I’m going to read all the books and do grief right, because I thought that was a thing. So I’m curious to know how your views on grief and grieving, maybe mourning, what they might have been in the early days before you really started having lots of conversations about death and how that has shifted over time.

Anna: Yeah. I mean the way you say you were going to do it right by following the curricula. I am very much that personality type as well. And I think I brought that spirit generally to every hard thing in life. I was like, “I’m going to be a student”, from a very young age. I collected quote books and I would, this is how you, this is what life is about. And I had older sisters, so I really did feel like I could be this very careful student of how life unfolded. And you could navigate your way through in just the right way.

And I think maybe that was also part of the origin story of wanting to start the show of just now I’ve experienced having my life fall apart. Let’s learn how to have your life fall apart and have a year of yes and do it just right and the whole thing. And that kind of very quickly fell away as I started doing interviews for the show and I became much more interested in the idea that many people have discovered before I have that we’re not dealing with equations here and algorithms and life hacks to get our way around and through these difficult things.

And the only thing that helps, that is sure to help is figuring out how to have a little company while you get through it, connecting relationally. That can mean that you share a lot with a group of friends. That can mean having a really useful, helpful mental health professional accompanying you. That can mean a profound experience of connection with the spiritual life. But where it’s not just sitting inside of you and that part of that relational process, I talk about talking about hard things, but it’s also surrendering to when you’re overcome.

And seeing it as this ocean that you’re in where you are subject to these waves that you are not going to control by just the right self-help book and I’ve tried. And I think I also kind of came to that when I was divorcing, when my first marriage was ending, I was a big student of marriage books. And there is this trope that at the time, this was how many years ago, 12 years ago.

It seemed like every hot marriage book started the introduction with some note about how second marriages failed at a higher rate than first marriages. So it wasn’t that you had the wrong partner, it’s that you did marriage wrong basically just the message I took away from it.

Krista: Cool. Thank you.

Anna: And I was like, “Oh, okay.” So that is not, I don’t actually, I don’t, I think sometimes you are not with the right partner. However, I did take from that this idea of marriage as this living, breathing process and intimacy as this living, breathing process that is not good or bad. It’s this organic thing, this organism that you’re building with this other person.

Krista: A great way to think about it is kind of its own entity. I love that. What was occurring to me as you were talking about the things that we go through. I think for me was that I kind of thought the point was to get through. And what I have come to realize is that it’s really about, for me being here with whatever it is. So Hugo was my second marriage too. The first one, I feel like, I don’t know, maybe we’ll have to compare ages and trajectories, but I feel like the timelines, the positive quotes are kind of lining up for me as I listen to you talk.

But I stayed in that marriage way too long. And part of it was for some of the things that you were saying, is that there’s a right way to do it and maybe I’m doing it wrong and made my bed, need to lay in it, those kinds of things, finally do get out. And then met Hugo and believed, okay, this is it. This is what I’ve been looking for the whole time and finally found it and then to have it taken away from me.

So in that time then again it’s still thinking that this part of life is awful and I got to get to the good part. And so for me, the journey has been realizing, actually where we all are is always where we are. And it’s not about skipping it. It’s not about wishing it were Friday or wishing you were at a less terrible place in your grief. Yes, it makes sense why we do that, but how can we actually just be with ourselves where we are in what we’re in? Because that is what our life is in that moment, and it’s how we relate to it I think that matters so much more than trying to get somewhere.

Anna: And it’s really, that’s so hard.

Krista: It is hard.

Anna: It is so hard because if you’re not totally all about your present, it’s hard to stay in the present because you’re like, “How do I”, for me, that idea of there can be a sense of hope in this idea of if I can just create the right momentum to shift this stuck feeling but I think you’re right. It’s zooming way out, the deepest friendships in my life are with people who have encountered profound loss. What they sort of constructed after a lot fell down is so, they just have so much, there’s so much richness that they can share.

And for some reason this is something that keeps coming to mind is I love talking to unmarried women who have been partnered about their closets and how they think about the prospect of sharing space again. And the sense of ownership over their own space that has taken hold slowly of after living alone. That sense of wait, there’s like this whole story of when will I find the partner again? But wait, you’re actually asking me, am I going to move my stuff out of my space to make room for this person in this closet?

And then it just flips the whole idea to think about what you would be having to make smaller that you’ve built in the absence, while you’ve been on your own. And I like being reminded of that. I think so much of our cultural expectations around partnership and companionship, it can create this expectation or this feeling, you’re incomplete or you’re in between rather than look at the way you could spread out all your glorious treasures that you’ve collected. Do you know what I mean?

Krista: Yeah, totally. It reminds me of Shell Silverstein’s, The Missing Piece. For a long time I remember really buying into that of thinking that I was looking for other people who were my missing piece. And then at a certain point, at least I didn’t realize it until after Hugo died. I think I fully viscerally realized, actually I am the one. I am okay. I am the creator of my safety. I am the creator of my piece. I have everything I need.

And then the whole idea of relationships completely changed for me because it became an opportunity to give instead of before is what I saw was just an opportunity to receive or something I needed as opposed to something that could be fun and light.

Anna: And do you think, as you made that transition, was it in relationship with other widows where you started to sort of rethink things or were you contrasting your life to partnered friends of yours where you were like, “I’m getting to do this in a different way?”

Krista: Yeah, I think it was probably a combination of things. So for one, it was seeing people who had lost their person, be it married or not. And then rebounded quickly because I could tell they were trying to fill what they perceived was a hole. And seeing that not work, in many cases fail miserably. And also being repelled completely by the idea of being in another relationship for quite a long time.

Because the first one didn’t work and then the second one died and I was like, “Forget it.” I remember going out with a coworker, a former coworker one time. I thought it was just for dinner. I thought we were just hanging out. And then I realized, no, he thinks this is a date. I was rip roaring mad after it was over, mad I was in that situation. I don’t want to date. I just want what I had, I can’t have it, all the tears, all the things. And so it was just for me the furthest thing from my mind for a long time was a new relationship, which then kind of gave me.

And then also watching other, what was happening in different grief groups I was in and just eventually coming to the conclusion that actually what I really want is just to be at peace with myself and to come back to me instead of trying to find something outside of me and figure that part out.

And then it’s this weird experience of loneliness where you sometimes feel it, but also not because you like your own company. And you don’t really feel the need. It feels like a more freeing place to live from for sure, because you don’t need to go find it. It becomes something you could have if you wanted it, but not something that I used to feel was a problem if I didn’t have.

Anna: You’re reminding me, this isn’t about losing a partner, but the writer Brandon Taylor, he’s a novelist and short story writer. He described his ideal emotional state as being a little bit lonely, alone and a little bit lonely. And it’s, for him it’s because it’s this entre into this world of books and words where he feels most at home and in himself. And I love that because there’s that little hunger for stimulation that’s outside of yourself but kind of liking it.

Krista: Kind of fuels you just a little bit little, a little bit of something. That’s interesting. So of the three topics that you talk about, I mean I know it’s a little more nuanced than just saying just because your podcast is called Death, Sex and Money. But what do you find is the most difficult topic for people?

Anna: I mean it certainly depends on where people are in their lives. I think we lack skillfulness the most in money conversations. And I think what I’ve come to sort of notice is that it’s very difficult to just start a conversation about how you feel about your financial life, what’s your relationship to scarcity or stability. What you hope for yourself and your kids and your family, it’s really hard to launch into that conversation where you don’t have the reference points. They’re not clear for who you’re speaking with or who your audience is.

And in the US, in western countries we don’t talk about class and money unless we feel like we’re talking within our own, however, we think of our own tribe. So I think that’s responsible for that’s what drives a lot of the silence and then that’s what drives a lot of the shame around money. Or that’s what drives a lot of the lack of confidence about the parts of your financial life that you can have some agency over.

For me, when I’m doing an interview, it’s not so much, “Tell me, what did you earn last year? What was your taxable income?” It’s more, tell me about your relationship to your survival instinct and how do you think about risk? And hearing Lynn Nottage, who’s a Pulitzer Prize winning playwright, two times describe, she was working an office job for a human rights organization. And she decided she needed to make art, and she decided to cash out her 401(k) when she was a young woman and to do that.

I find that useful to hear her share because when I think about my own financial life, I am so much somebody who wants to make sure I’m following the rules. And so hearing people talk about money as there’s something you can relate to with sets of values that shift over time. And depending on, they’re context specific. I think that is very helpful. I think it’s really helpful for people to be invited and to think about the cost of housing or the burden of student loan debt in a way where they don’t think, what have I done wrong that this thing that I’m not supposed to be struggling with, why am I struggling with it?

And to create conversations that help people recognize, no, this is a generational thing. If you’re a millennial, if you went to college after the financial crisis, higher ed cost a lot more. And so I think there’s a real service in trying to have a lot of different sorts of conversations around money. That said, back to your original question of what’s the most difficult conversation to have?

I would say for me where I am in my life right now as a parent of two young kids. When I know I have an interview coming up about someone losing a child. Those are the interviews that I can feel it in my body, I’m dreading it. I know I need to schedule a long walk afterwards. It’s going to take a lot out of me because just witnessing the possibility of what can be lost, which is important to do because it happens every day to people. But it’s such a visceral sense of it’s such a deep fear that it’s difficult for me at this point in my life to talk about.

Krista: Yeah. So you told me you go on a walk after. How do you support yourself in the middle of that interview when you’re feeling that fear or anticipating that fear?

Anna: It’s kind of like when I’m doing an interview, it’s different than being in a conversation with someone who I’m in relationship with. But when I’m doing an interview, so much of my focus is on really wanting to pay attention to making sure I’m understanding all the things they’re communicating to me. What are the words they’re choosing? When their answers get clipped, do I need to signal that we can move to a different topic, we don’t have to go deeper into this.

I am very focused on wanting to make sure I’m understanding what they’re trying to say. And also that I’m doing the interview in a way that feels ethical, responsible and relational. Really just kind of something I do is I’ll notice back, maybe what I’ve had therapists say to me, when a therapist might notice, if I exhale before answering. I’ll notice, I noticed you just, you said it this way or can you tell me more about that? So it’s not so hard for me in the moment because so much of my attention is on exactly what’s happening minute by minute.

And it’s only after and I’ve had to learn this, especially during the pandemic, I can’t just go to the next Zoom about whatever, open enrollment [crosstalk]. I’ll be a mess. I have to lay horizontal and breathe and let what I just witnessed and participated in together with the person I was talking with, I have to let it hit me, yeah.

Krista: So it sounds like you’re really good in the moment of focusing on the other person and the task at hand, but then you also know yourself well enough to know that you need to create some space afterward for your own processing.

Anna: Yeah. And that’s trying to do the things that they tell you to do, go for a walk, take deep breaths and it helps. But it’s still really heavy work. And it’s heavy also especially when it’s a remote encounter because you can’t, I also, I’m like, “What is the aftercare for that person that they’ve just talked to this podcast interviewer about this?” And we went deep and are they going to the store now? Do they have to pick up their kids right away? What is happening with them? And what was their experience of that?

So the way I’ve learned how to manage it is how do I manage the walk for myself. But then also really trying to be in communication with someone afterwards so they know it’s not just a parachuting in journalist who’s extracting their story and moving on.

Krista: And then leaving them in a pile and discarding them. I think I’m kind of lucky in that most of the people that I interview, when we’re talking about hard conversations, typically have been my clients. So I have the benefit of knowing I’m coming into the conversation having already kind of armed them with some emotional processing tools. And having had big discussions about really hard things in their life before. So I’ve never been in that position where I had to have tough conversations with people who I’m not already in pretty strong relationship with.

Anna: And I think in those cases we’re talking about hard conversations, but you can also feel the opposite, which is the sense of deep connection and power that can come from co-creating a conversation and listening, feeling listened to. So I feel that’s the part where when I do feel there are icky parts of this work of making people say hard things and then putting [inaudible].

I do think it is, there’s a mission and there’s a service to it, which is the person who you’re paying attention to and letting them be the narrator of their story at length can be a very empowering experience. And then there’s the service of having for the listener who needs to feel like they’re not the only one.

Krista: If you were trying to find the silver lining in every story, find the positive happy outcome. It sounds like in your teenage years where probably would have been inclined to do it would feel probably pretty creepy.

Anna: Yeah, I took a Moth style storytelling class before I started the show and my teacher, Adam Wade. He’s a storyteller in New York. It kind of echoes in my head when I’m doing edits. He would always say, “Don’t put a bow on the end, take off the bow.” Just let the end just sit there and land for a listener instead of being like, “And that’s it so, here are your takeaway.” Because the bow is like let’s make this not have loose ends. And I really think loose ends are where it’s at, we’re all dragging around some loose ends every day.

Krista: I love that so much. I think actually that’s a huge thing in coaching too, because I think I am a coach, but also I train coaches and especially master level coaches. I think that is one of the hardest habits to break. When you put that kind of pressure on yourself as a coach to tie it all up, to make it pretty, to show them where they’ve come. And also it’s a little bit, it’s so limiting because I think loose ends open the door for the next introspective moment that they might have on their own. And if you kind of tidy it up too much, they miss that.

So it’s kind of a weird experience for the coach because, I don’t know, just feels creepy. But I get why we do that. If we think, and this is what I used to think, I’m curious about your opinion on this. I used to think when I discovered coaching kind of the goal was to feel better. I was still in that place where I was kind of buying into the happiness is the goal of life place. And so as opposed to what I believe now, which is just being human and feeling the feelings is the point of life and consciously creating what we want and that doesn’t mean it’s all good at all.

But because I was coming from a fix it because it’s broken mentality, that really showed up in my coaching versus now I feel like feelings aren’t problems to be fixed. They’re just experiences to be allowed. We don’t know why these things are happening to us other than because we’re human. But it’s not like we have to find the silver lining or be grateful. It’s this happened and then what do I want to make of it? And I’m feeling this way and now who do I want to be?

And none of it is morally superior or somehow better than. It’s just choices we get to make along the way, which is really different than, I feel like I could get my journal and show it to you and you’d be like, “Yeah, I have those same quotes written down from 16.” Of the point is to be positive and happy and do it right, I don’t know.

Anna: I mean this idea of not messing up and it’s something I’ve been thinking about lately is if that’s your paradigm of if I’m managing things well, I’m not messing up. When you do not know that next step, the shame, man, why can’t I figure this out? And shame is heavy and shame gets in the way of experimentation and taking risks. I’m turning 43 this week, as I turn 43 I’m trying to, yeah, move away from that idea.

Have more self-compassion and that when you don’t know, that’s your information right now. And I saw this quote, this is an Instagram quote, I still like quotes, but this quote was nice. I think it’s a [inaudible] it was some years are questions and some years are answers. And I really appreciated that because the heaviest emotional times in my life have felt like when I feel a heaviness, but I don’t know an action that will help it lift. And so then I feel like I’m not competent and I feel shame.

Krista: Because the heaviness is somehow a problem that you’ve caused?

Anna: Yeah. Or a problem I’ve caused or even if I haven’t caused it, can’t I work my way out of this? Can’t I do the right yoga routine or the right whatever? Our culture teaches us that it’s just you just need to keep tweaking your self-care and you’re going to feel alright. And I think it’s so freeing to be like, “Oh, I’m noticing this is new, it’s a new question.” If I can bring that spirit that feels so much sort of looser.

Krista: Yeah. To be able to be with uncertainty and let something show itself to you as opposed to needing to try to solve it or figure it out. Yeah, I resonate with that too. I think that was what was initially really attractive about life coaching was that it to me, had the answers. It’s like the great bait and switch. No, actually, you don’t need all the answers. You’re never going to get them. And how about we just make peace with uncertainty? Surprise. [Inaudible] transition now. So tell us about your book.

Anna: My book, it’s called Let’s Talk About Hard Things and it started as kind of people would ask me, “How do you know how to talk to people about hard things? How do you get people to open up?” Because I don’t have, I’m not a psychologist. I don’t have a mental health background. I’m a journalist. And I was like, “Well, what is it that I do? How is it that I create the conditions in an interview to slow down enough and to make enough room that we go to places that are often unexpected for me and the person that I’m interviewing?”

And so that’s how it started. And then it kind of, as I thought more about the utility of such a book, I also felt really clear that hard things are not new in life. We have always had difficulties dealing with death, sex money or any number of hard things. But I do think that in 21st century America we have less rituals, we have fewer sort of go to institutions. We have less sort of customs that we follow collectively that accompany us on going through these hard things.

And it feels to me like the onus is on each of our shoulders individually to become more skillful at talking about hard things. One example could be, if I meet a mom, a drop off who I learn lost a loved one during COVID, what is that thing I’m going to say quickly as I’m getting to know them, to let them know I heard them? I understand how their family is built now and that it’s part of this collective loss we’ve all been through as a culture. There’s that example.

Or there’s figuring out, should I refinance my mortgage? And it used to be that we would go to our neighborhood brick and mortar bank and sit down, maybe with somebody who we’d known for years and talk to them. And now I don’t know about you, but I make all my major financial decisions by Googling and going to various personal finance websites and then entering calculators and then I hit submit.

And I have been the only way I’ve gotten through the gauntlet of early parenthood and childcare costs and figuring out what to do is being the one who’s brave in a conversation with another parent of young kids. And saying, “Hey, how do you do this?” So there’s those two ideas of I wanted it to feel like an invitation, let’s talk about hard things. All of us have hard things. It’s a series of kind of reported characters that you meet who talk about kind of learning key sentences that have been helpful in dealing with hard things.

One in the sex chapter is, what are you into, a sentence that can lead to all sorts of clarity with a potential partner or a long term partner that you haven’t had that conversation with. But also that there’s a real responsibility I think we have to not dodge in because we’re building back some connective tissue that I think has just been tattered in our communities. And we can do a little work relationally to build that back by not being as scared to talk about things we don’t always know exactly how to start talking about.

Krista: Yeah, and I think the more and more we depend on social media and the more siloed we are and where we get our news and the more binary we are in how we think about groups of people and what they believe. I like that you use the word responsibility. I probably would have used the word opportunity, but I like responsibility better of that is how we find common ground and move forward and connect as humans, is by one at a time having uncomfortable conversations and getting to know where someone’s coming from.

This isn’t really necessarily about grief, but there’s just so much value in that, and it really is going to take individual conversations, which to me, for me personally is being willing to feel something that my primitive brain doesn’t want to feel. Being willing to expose myself to rejection, which my brain decides also means I could die. And being willing to let those feelings exist and be open to a conversation that maybe isn’t easy.

Anna: Or opening yourself up again to a different kind of uncertainty. Maybe you think you know all the things that you believe about a certain thing. But you’re hearing somebody who might have a life that looks really different to you, talking about some different way they see it. And can you tolerate that? Can you tolerate maybe it’s more complicated than how I have slotted it in my brain?

Krista: Yeah, secure in my brain. This is literally having a, I was going to say conversation with myself on my walk this morning. I was thinking about [inaudible] on my brain. I wasn’t even preparing for the interview. It was just what I was thinking about. I’m curious because I know we’re going to have to wrap up soon, but I’m curious to know because I struggled with it and a lot of widows that I have worked with struggled with it.

But what have you seen and why do you think we struggle with it so much as it relates to money after your person dies? So they die, you get life insurance or some sort of payout. And then I call it wealth purgatory, where you have more money than you thought and you think you’re going to feel good but you actually feel terrible. What have you seen in the interviews that you’ve done with people as it relates to money after a circumstance they didn’t want?

Anna: I mean it’s complicated. I just talked with, we did an episode about paying for weddings. And one of the people I talked to was a young woman whose mother died suddenly and she inherited money that she did not know she was going to inherit, including a fund specifically for a wedding. And so she was enabled to have a wedding celebration that was much fancier than she and her partner had ever thought would be possible for them.

And there were all sorts of feelings that came up around that, including, oh my gosh, would my mom think I paid too much to the dry cleaner who I had? Because she’d bought a used wedding dress that was a good value, but she thought her mother would think that she paid too much to have it cleaned, dry cleaned. And then there was the social anxiety of all of our friends and loved ones know what we do for a living and they know that we could never afford this on our own. And how do we acknowledge how we paid for this?

And how do we bring my mother into the room and thank her for the generosity? Also, the fear of, she was afraid, she realized she hadn’t budgeted for tips, and so she was over budget for all of the caterers and things. So then she was like, “Do I put it on my credit card or do I ask my dad for help even though he’s just lost his wife?” All sorts of hard, guilty, shaming, money stuff come up. And it’s because it’s not about money. It’s about our relationship to this memory, and I don’t feel secure and then I have more money than I ever have and that doesn’t make sense.

And what is money even for? That’s a question that can be updated and quite probably needs to be after how you thought your life was going to be, is going to be if it’s a sudden loss, what matters to me? And so I think that money is this container, this money, I have so many feelings about this money. You have a lot of feelings about the loss of this person. And alongside that you have this question of what do you do with these dollars that are in this account? And it’s staring at you, that you haven’t made choices or whatever or maybe your partner left you with a lot of debts you didn’t know about.

So I think it’s really hard. And I think the other thing that when I was working on my book that I talked to therapists and health professionals about is it can also be difficult to find a therapist who’s really willing to talk about the emotional dimensions of money. Because as a class, as a group, as a cohort, therapists tend to be kind of money avoidant. They tend to be very service oriented people. So not people who like to think about money being a key value. So talking about it can feel crass.

So you’ve got to find the right person who can dig in there with you about it. It’s about what I have observed is making choices about money are real choices you have to make. And the best you can hope for is getting clear on what are the feelings around it by kind of trying to unbraid the feelings you have about the money with what the money as a tool can achieve for you.

Krista: Yeah. And sometimes you’re being asked to make those decisions at a time when people are telling you, don’t make big decisions, which is also super fun. And feeling like as you described, gravity has been suspended and we’re now floating above the earth.

Anna: Yeah. And what are you going to do with the house? Yeah.

Krista: Right, yeah. So many rules. I wish we had more than an hour. This has been a really great conversation. Thank you for coming on.

Anna: Thank you for having me, I really appreciate it.

Krista: Was there anything you wanted to talk about that we didn’t? So they need to go listen to your podcast Death, Sex and Money. Let’s talk about her things on your book.

Anna: I mean the one curiosity I have is have you found, I’m just curious, in your work talking to people who have lost their partner or their person, are you able to connect? How much are you able to connect intergenerationally and how much do you feel that your precise experience you feel the most kind of understood when it’s somebody who is in a similar life phase? Because I imagine it just feels, you have so many different expectations around how long a partnership might last when you’re in midlife versus when you’re coming to the end.

Krista: Yeah, I don’t find it difficult to connect so much. And I guess in my mind I am kind of just always trying to view the world from kind of a neutral perspective from where I sit, but also simultaneously viewing it as they view it. I think because a lot of what I’m doing is dealing with pretty intense stuff. Some of that is just helping, it’s just education. It’s helping people understand what goes on in the human brain when we’re partnered. And why it takes time, but also time isn’t the only thing it takes.

Because people don’t know much about grief, no matter how long they were with their person or how their person died or whatever, because they don’t know much about what to expect. What I notice is that the similarities are that they tend to blame themselves. They tend to think there’s something wrong with them. They tend to think there’s a right way that they should be experiencing it. They expect it to be linear staged. They’re never where they should be, of course they should always be further along.

And so it’s those things that connect more to me than the circumstances of the loss or the relationship. That’s why I eventually decided, well, it’s been a number of years ago. But in the beginning I only did one-on-one work with people and that’s what eventually made me decide, no, this needs to be done in community. Because most of what I’m coming up against with people as their roadblocks or that they think that what’s going on with them is only happening to them or that is some sort of character flaw within themselves.

And if I can get them in a group and I can normalize what’s happening and they can see it in other women with very different life experiences. So I’ve got a woman coming to the program. I’m so excited. She’s 86. I am so here for it. And then I also have all the way into low 30s. But it doesn’t really matter how or when or whatever has happened, none of it needs to be weaponized. None of it means we’re crazy. None of it means we’re doing it wrong because it’s just not possible to do it wrong.

It’s those things that people can see in each other and then normalize and find comfort in the relationship of, okay, I see myself in her and maybe this is just really hard and I’m not broken. Maybe this is just what grief is like. And that to me, those are easy connections to see. I was just going to say, look at me trying to ask you a closing question and then you get me all started again. I’m like, do we have to be done? We could just keep going.

Anna: Sorry. Yeah, that’s really interesting. I’m really glad that we connected over video and I’m excited to dig in more to your work.

Krista: Well, same.

Anna: It sounds like you’re providing quite a community for people who need it.

Krista: I love what I do on a level that I would have never expected truly. Yeah. Well, thank you again so much. Maybe you could come back.

Anna: Yeah, let’s hang again.

Krista: Thank you. I would love to do that. Thanks, Anna.

Anna: Okay. Bye.

If you like what you’ve been hearing on this podcast and want to create a future you can truly get excited about after the loss of your spouse, I invite you to join my Mom Goes On coaching program. It’s small group coaching just for widowed moms like you where I’ll help you figure out what’s holding you back and give you the tools and support you need so you can move forward with confidence.

Please don’t settle for a new normal that’s less than you deserve. Go to coachingwithkrista.com and click work with me for details and the next steps. I can’t wait to meet you.

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About your coach

I created a new life using small, manageable steps and techniques that made sense. The changes I experienced were so profound I became a Master Certified Life Coach and created a group coaching program for widows like us called Mom Goes On. It’s now my mission to show widowed moms exactly how to do what I’ve done and create a future they can look forward to.

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