Episode 06 · 11 December 2025 · 44 min
Grief at Xmas
with Jennie Cashman, Grief specialist
Christmas doesn't make grief disappear. Sometimes it turns the volume up.
Jennie Cashman explores the particular weight of grief at Christmas: the empty chair, the traditions that suddenly feel different and the expectation to be joyful when you're anything but. A conversation about supporting yourself and other people through a season that can make loss feel especially visible.
Core themes explored
- The particular weight of grief at Christmas
- The empty chair and changed traditions
- The expectation to be joyful when you're not
- Supporting yourself and others through a difficult season
TranscriptRead +
Carly OsmanSo, hi Jenny, thank you so much for joining me today. I'd love to, before we get into the crux of grief and especially grief at Christmas, tell me a little bit about yourself.
Jennie CashmanOkay, so i live in two countries. I mean, I've lived in lots of countries, but at the moment I live in two. And I'm in Brussels today. and I also wear two hats in terms of what I do for my job, for my career. So I mainly work with purpose-driven creative entrepreneurs. so I work with them one-to-one. and I help them build sustainable businesses. So what I mean by that is I tend to work with founders and freelance creatives, music managers, often people working in the music industry, because that's kind of the background that I have. And they're people who have an entrepreneurial mindset, and they want to build something that is bigger than themselves something that goes beyond like hitting the next income goal but yeah I'd say they're ready for something for something different in their businesses they want it to look and feel different different they understand that what got them here isn't going to get them to where they want to go to and they care about their work deeply and they're really passionate about it but they don't want it to just completely dominate their lives anymore and they want to find some more ease with it. So yes, they want it to sit at the center of what they do, but they want it to feed them or nourish them. rather than drain them. And so, yeah, build a business or a career that supports the life they're trying to build. Not one that just completely consumes it, which is very difficult in the world that we live in. And then the other thing that I do is I facilitate high performing groups and teams. So, and I focus on how they can be more productive, more innovative and collaborative by leaning into things like experimentation, creativity, and curiosity. And then prior to that, i was the founder and CEO of a grassroots music organization called the Abram Wilson charity. which I established in 2012 in honor of my late husband, who was a critically acclaimed jazz musician from New Orleans called Abram Wilson. I set it up to help minoritize young talent access the music industry. And then mine and Abram's story ended up inspiring me to accidentally write a children's book, which was published by Little Tiger. It's called Becoming Brave. And that was named as the one of the Guardian's best new picture books when it was published. So yeah, that's bit about me.
Carly OsmanAnd it's the grief area that I really want to dive in with you today. We met a couple of years ago and at the time you were really helping people around Christmas
Jennie CashmanTwo years
Carly OsmanGo through what is a really transformate transformation, kind transformative, but that's not even a word stage where quite often people were in that first year of grief when they had lost someone that they loved. And it was, how do you face Christmas without that person? How do you go through this time that is meant to be full of merriment and joy when it's just not feeling there? So my kind of first question is to you why Well, well what I know why Christmas is so hard, but how what can people do?
Jennie CashmanOh my gosh, that's such a good question. Yeah, so that was one of my projects a couple of years ago when we met. So I was kind of exploring different sort of avenues and things that I could do. I sat down from the Abram Wilson charity, I think it was August 23. And so it must have been the following Christmas, right? 24? 2024? and jenny four And yeah, I think I've been, I was sort of thinking about different things. And for me, Christmas had always been such a struggle. So my my baby brother died i a week before Christmas. He was three three months old when he died. i was And I just turned four. So it was a week after my fourth birthday and a week before Christmas. And I think looking back, that had monumental impact on how we celebrated Christmas as a family. And and I just remember it, the feeling of Christmas. I was quite a sensitive kid. I'm still quite a sensitive human being, to be honest. But I just remember the feeling of Christmas just being very sad. And, you know, just little things like, I don't know, my mum would just sort of she she'd do things like she'd she'd sort of be really disorganised with presents. It sounds so silly. But like, I remember being a teenager and like having to wrap up like everyone's presents apart from mine, because my mum just like, I think it was just part of her... you know, she just couldn't deal with it, basically. I mean, it was, you know, I guess we were probably like, it was probably a decade on. And I think that's the thing about grief, isn't it? Like, if you've not been through it, if you've not been through the the experience, if you've not experienced losing someone who you're really close to most people don't understand it. It's like, they think, oh, it's a year later, or it's two years later, or it's three years later, like, come on, time to get on with it. And it's like, you know, it lives with you always, you know, and and I think depending on the relationship and depending on, yeah, but how that person passed away, you know, it can really take a long time to get to a place where, where you're okay again.
Carly OsmanThank
Jennie CashmanAnd sometimes you, sometimes you're not, you know, sometimes people just aren't. So it just, it kind of depends on the person I think. And so in terms of like what you can do, like I just didn't celebrate Christmas very well for like ages. I hated Christmas and I just really wasn't into it and I just really struggled with it. And then I think I just spent some time that kind of first year that I wasn't running the April Wilson charity anymore, just thinking about that a bit more deeply and realizing why that might be and actually trying to make a bit more of an effort around it and also just have a bit more of a conversation about it. I'm realising I'm talking a lot, so I'm just going to pause there.
Carly OsmanNo, this is perfect. suppose it No, this is perfect. So you've kind of described it as an, well, grief is nonlinear, and it can kind of hit in waves, and it looks different from everyone else. Is there any way? And I'm going to caveat this, I've not someone who has experienced deep grief, I've lost grandparents, but I've not lost anyone close to me. So I'm always looking from the, I'm an outsider looking in and my personal mis kind of selfish mission here is how do i one, plan for it better, but also, two, support people around me who have lost people?
Carly OsmanWhat can I say to them? How can I be a better friend? How can I show up in a better way when they are in deep, deep grief at this time of year and all the traditions they've gone with Christmas and their loved ones have suddenly disappeared? Like, is there anything I can say and anything I can do? Or is it just... you've got to let this person be and actually trying to make small talk, trying to push it through is actually making it harder and worse.
Jennie CashmanYeah, it's a really good it's a really good question, right? Because we want to help, but also, you know, especially if you were if you grew up in the UK, but you're not really quite sure how to go about it. And, you know, talking about big feelings or dealing with big feelings could sometimes be a challenge depending on your upbringing. so So, for example, one of my friends, one of my best friends lost her mum a couple of Christmases ago. And she's actually one of the friends who helped me to love Christmas because she loves Christmas, like really loves Christmas. She's just, it's so cute how much she loves Christmas. Her and her family are just so into it. And, you know, they'll have like a Christmas tree up like, latest 1st of December I'd say and and it's it's a lovely thing and then you know and then her mum passed away just before Christmas and you know that was awful because she she loved Christmas and then you know and her mum had been you know basically going going through cancer and had eventually started sorry had eventually decided to stop treatment and so they knew it was coming they just didn't know when And it was a good death in the sense that, you know, her and her brother were both with her mum when she passed away.
Carly OsmanThank
Jennie CashmanI might cry. so yeah, I hope that's OK. But I think it was. She was somebody who didn't really want to talk to anyone unless they'd been through something similar. So I was one of the friends that she let in. But also she's not, we're quite different in the way that we express ourselves. You know, like I think the way that I express myself when Abram died was to be very open about it. And I was very, I mean, he was, he was a public figure in in the UK jazz world so I got a lot of messages and emails and phone calls when he passed away and and so I would write about it quite publicly and we had a big public celebration of his life and you know and I set up I set up an organization a charity and built that for 11 years and you know and I talked about him all the time, you know, and every time we did an event, every time we did a gig, you know, i'd be up on stage, I'd be telling his story. I was, you know, i mean, that was my whole life of pretty much my entire thirty s Whereas my friend, whose mum passed away a couple of years ago, is you know, she was more private with it, much more private with it. And really, you know, didn't want to talk to people who hadn't gone through something similar. and i And I think she was quite angry as well because her dad passed away when she was very young. So that actually she she doesn't have parents now. And that really hit hard. And I think also, you know, the fact that it was around Christmas, which was her favorite time of year. So I just tried my best to let her know that I was there. And I kept checking in and... kept sort of asking what she needed, what I could do. I mean, it's difficult when you're sort of in that state because you don't really know the answer, but it's also nice to know that people are around and, you know, some people, people are different. That's the thing. So you have to sort of gauge it based on the person and your relationship with them. I have another friend whose wife passed away a couple of years ago and he's been incredibly private about it. And he didn't want to... He didn't really... hes I've never had a conversation with him about it. Like, we've been... We corresponded a little bit via email and text. But I've never actually had a conversation with him about it. The only conversation I had with him was when she was diagnosed with cancer, and it was a very similar cancer to Abrams. And then I think it was, like... Maybe two years later she died, something like that. i can't remember the exact timeline. But I've never spoken to him about it since. And because he's been incredibly private. So i don't I suppose what I'm saying is I don't have the answer necessarily because it depends on the person and it depends on their relationship with that with the person who's passed away and how they're going to how they're how they're going to grieve and everyone's grieving process is different and some people will just push everyone away and other people will do the complete opposite and then you've got everything in between.
Carly OsmanSo what I'm kind of bor i' hearing is just for an outsider, just constantly offer and say, I'm here. Just let the person know that you're here. And if they're ready to talk, if they want to talk, it's completely up to them, but you're always thinking about them. And then for someone who is deep in grief, how do they navigate this pressure to perform? And I think it's this, everyone's got to be festive. Come on. It's the 1st of December. Let's get into this festive spirit. How do you How do you put your boundaries in place and how do you say no if you're not in that mood or how, how do you put yourself first?
Jennie CashmanThank you. So i think, personally, I think that if you've lost somebody sort of recently, you've so so society kind of gives you a little bit slack, right? I think you've probably got about three months of slack. based on my experience, others might feel differently, where you can basically just say and do whatever you want and people will be fine with it.
Carly OsmanOkay.
Jennie CashmanBut then after that kind of three-month period, people's patience and understanding starts to diminish, shall we say, because they're not going through what you're going through. you know And the longer that yeah the longer the time goes on, the the more that kind of patience and understanding diminishes. And so then that's when you really have to start thinking about how to protect yourself and and what it is that you need. And be clear about that. And you know and and people aren't necessarily going to like it because they also have needs and they also have wants. And Christmas is a very like, you know it's quite a tricky time of year at the best of times. you know like I think most people will find it difficult in some way, even if, you know, like, you know, this friend that I mentioned, they love Christmas, you know, there's, that you know, they're having to deal with in-laws or they're having to deal with, you know, teenagers or they're having, you know, there's something that's kind of going on that's kind of, you know, we've all got to spend time together. And so for lots of people, it's a tricky time of year anyway. But I think, you know, if you're grieving, and you're able to to even, you know, because it's tricky, isn't it? If you've got kids, for example, and I think this is where my mum really struggled because, you know, her baby died a week before Christmas and she had two young children. She had a four-year-old and a two-year-old. And a husband that was, frankly, bit, well, emotionally stunted, to put it politely. So, you know, i i don't i honestly don't know how she got through that. I don't think she did particularly. so And I think that's why Christmas was so so difficult, was because she was really trying to put on a brave face. And she grew up in a household that really loved Christmas and really celebrated it And I think it just... you know the fact that the anniversary of of her of her baby's passing is a is a week before Christmas I mean like we never I never forget that I know she doesn't so I think it's you know I it's tough it's tough there's a lot of pressure there isn't there so I think it's about personally I think and I you know obviously I'm not the kind of bible on this but but
Carly OsmanThank
Jennie CashmanIs You've really got to to tune in to what it is that you need. And even if it's just teeny tiny things that you can do for yourself, then, you know, a little no here. A little no there, you know, a little, a nice little, you know, treat here, nice little treat there, you know, or just don't. I mean, the first Christmas that i went that I had after Avon passed away, so Avon passed away in June. And so it was six months later when we were, you know, celebrating an inverted commas Christmas.
Carly OsmanThank
Jennie CashmanAnd I, my dad was living out in, where was he? I think he was out in the, UAE. So I just, I flew out with one of my best friends at the time. And she, you know, was spoke to her mum and dad and said, is it okay if I don't see for Christmas this year? I'd really like to support Jenny. So we flew out together and we had a completely different Christmas, a friend's Christmas with my dad in the sun for a couple of weeks. And That was really nice, you know, it was just, it was just away from everything and everyone.
Jennie CashmanAnd I was very lucky that I was able to do that. and not everyone can do that. You know, I didn't have kids with Abram. I didn't have those sorts of responsibilities. I was like 32, you know? So i think, yeah, I feel like I'm not being very like definitive in my answers because I think it depends on the person's situation and their responsibilities and, you know, also their financial constraints as well. But I do think that there are ways, regardless of these, where you can tune into yourself and really ask yourself what it is that you need. And even if it's just pausing for five minutes and having a quiet cup of tea, you know, that's something.
Carly OsmanDid you ever struggle with guilt of enjoyment? So you said that first Christmas, you actually had a nice time with a friend and your dad in the sunshine. Was there any guilt that came with that?
Jennie CashmanWhat guilt that I was celebrating and grieving at the same time.
Carly OsmanYeah.
Jennie CashmanYeah, it was, I don't know if it was guilt, but it was just, it was such a crazy time, if I'm being honest, you know, like I kind of, I mean, I'm 44 now. So sort of look back and I'm like, wow, I was so, you know, you turn 30 and you think you're so grown up.
Carly OsmanThank you.
Jennie CashmanAnd then something like that happens and you're like, oh my gosh, I'm really not that grown up. So yeah, it was, I i think I've always been I think i when it when it comes to big things like that, I think I've... I've been quite good at making decisions for myself based on what I need, even though it's not necessarily like... Even though there there might be some you know some people frowning you know though at the decision. But like I said, you've got a little bit of leeway in the first few months. So my I could sort of feel my time was definitely like running out.
Carly OsmanThank you.
Jennie CashmanAnd I think, yeah, so I think they're probably... was guilt there. But I also knew that it was something that I needed. and I was very happy to sort of be with someone that I was very close to. You know, she was one of my best friends. She knew me really well. She knew Abram. And we were just able to kind of hang out and i could just be myself and I could, yeah, it was, it was, in a way it was easier because I was away from everything, you know.
Carly OsmanYeah
Jennie CashmanAnd my dad is sort of one of those people that he's not, he can't sort of emotionally engage particularly. so So we were just able to kind of pretend that everything was fine, even though it wasn't fine, which I kind of sort of, I just didn't want to really get into it. And, you know, I could do that with my friend, I suppose. And then my dad was just there going, another glass of wine so that yeah well there wasn't kind of that pressure I think because so you know it was the other the other that the way of Christmas had always been tricky anyway especially around my mom not so much now but so I just I was just able to get away from all of that and I think that was there was definitely a bit of guilt I think but it was overridden by by what and by what by what I needed at the time.
Carly OsmanHave you always been an an emotionally open person or is this something that you've you've learned and you've grown over time? Because I think to your point, we live in the UK. And it's a stiff upper her lip of keep calm, carry on, just trundle through it will be all right. Let's squash down any feelings and emotion until we boil up and explode. Have you been quite good at actually going, okay, what am I feeling here? What is that? Let's name the emotion. Let's talk about the emotion. How does that feel? And how is that manifesting?
Jennie CashmanI think have I always been I don't know if I've always been good at it but I think I learned to be good at it I think when did I start therapy that was probably when I started to get better at articulating how I was feeling about stuff and then I think actually Abram passing away was a big turning point for me speaking about it speaking from the heart and being open and honest about how I was feeling. i think I think I've been i think i've been very always very good at tuning into other people's feelings and knowing, yeah, just, I don't know, connecting with other people on an emotional level. so i i didn't And I think there was also something about the fact that when my brother died, My parents' response was to just completely shut down. They didn't want to talk about it at all. So there was zero conversation about my brother passing away, which meant that Even though I was four, I wasn't able to really process my grief around that until quite a lot later. And I think I needed to do it because i thought it was my fault, for example, because I didn't look after him because he was my baby brother.
Carly OsmanThank you.
Jennie CashmanI thought I hadn't been looking after him properly and that's why he died. So, you know, i when Abram passed away, i didn't i wanted to do the opposite of that. You know, i wanted to be i wanted to kind of take the moment and use it as a as a way as a a way of giving people an opportunity to talk openly about death and about grief and about loss and what that feels like. And and we don't... You know, it, like you say, it doesn't happen as much in our society in the UK. And it just felt, it felt important to me to do it because I was like, well, this is, this is enough. This is a chance for me to do something, to do it differently and to see what that is like. And while I don't regret it, it did mean that i was talking about my late husband for over a decade publicly.
Carly OsmanYeah.
Jennie CashmanAnd now I don't have to do that anymore. And I'm and my life is I have a very different life as a result. Like I'm not defined by that now. Whereas I really kind of lent into it and it it sort of ended up defining me in many ways.
Carly OsmanYeah. That's really interesting. I suppose what you're talking about there is it's a balance of getting, using the time to get to know yourself a little bit more. And would you recommend therapy to everyone going through grief?
Jennie CashmanYes, but it's about finding the right therapist.
Carly OsmanYeah.
Jennie CashmanI think people get put off therapy because they go and see somebody who's just because somebody is a therapist doesn't mean that they're a good therapist or that they've dealt with their their own stuff. Well, so it's really important to to do your research and to go and meet a few different people and find who you click with. So, you know, I mean, my my the friend that I mentioned earlier, whose mum passed away a couple years ago, you know, she was seeing a therapist before her mum died and she did continue to see that therapist. And I think although the therapist wasn't quite right for her or wasn't challenging her in the way that she wanted to be challenged she still recognized that it was a good thing for her to do and obviously there's lots of different types of therapy as well so I mean I was lucky i feel like I was lucky because I'd already been seeing a therapist for three years when Abram passed away so she she knew our relationship really well
Carly OsmanYeah.
Jennie CashmanAnd I didn't have to start from scratch which and she was she was amazing and she was so you know I didn't have to explain myself right it was like I could just be in my grief I didn't have to kind of you know explain the relationship or explain what he was like or we could just carry on the conversations that we were having and and there was an opportunity for me to, palliative the palliative care team offered therapy after Abram passed away. And so i said to my therapist, I said, oh, well, I'm going to go along and meet somebody because, you know, it's it's free and it's part of, you know, the NHS. And, you know, they might sort of specialize in grief and maybe they might be able to offer something that that my therapist isn't able to offer me. And she was like cool about it. She was like, yeah, sure. If you want to do that, that's totally fine, obviously. And I went and it was like one of the worst experiences I think I've ever had. It was, she you know, just like from the moment she came out to greet me, it was bad. you know and then we sat down and she was asking me lots of probing as soon as I mentioned that he was you know well known within the world that he operated in she started probing me wanting to know who he was and trying to get a sense of like how famous he was in inverted commas you know mean he he was a jazz musician he was never going to be that famous but
Carly OsmanYeah
Jennie CashmanBut I was just like, what the hell is going on here? Like it was just, I mean, fortunately I went to see my my normal therapist straight after. so was kind of able to like download, but you know, I could i could really see how like therapy therapy can be quite damaging if you're not careful, that you have to, you know, you have to really, especially if you're going in at the worst time, you know? So you so i would say you just have to be discerning, but yes, it's a good thing overall.
Carly OsmanI also think it's probably challenging time as well because I think when someone dies they're always seen in this oh they were wonderful they were perfect but actually quite a lot of people have quite complex relationships with family members or partners or whoever and actually you need to get you need to kind of grieve that part as well that
Jennie CashmanYeah.
Carly OsmanIt wasn't the ideal, it wasn't perfect, but you can be sad and it's allowing space for the two things to coexist.
Jennie CashmanOh my God, yeah, totally. Like, you know, Abram was not a perfect human being by any stretch of the imagination. And, you know, we had our issues like any couple. But he was also an amazing human being. And, and you know, I've yet to meet another musician like him. And i've I've met and worked with a lot of musicians over the last 15 years. Like, he was quite extraordinary. But he was also so annoying.
Carly OsmanThank you.
Jennie CashmanAnd so chaotic and so single-minded at times and you know that and and you know and that that could be that could be tough and so yeah to be able to to grapple with that and you know and also you're either depending on the relationship I mean obviously you know I was 31 when he died you know I thought I was going to spend the rest of my life with him so I also had to grieve the life that I wasn't going to have with him and and and and sort of pivot and start to think about building a new life and embracing that and what would that be but I couldn't really do that until I properly grieved him and grieved what I believed that that we were going to try and build together and also accepting that that might not have worked out either so you know there's all sorts of layers there and it's you know like you know the friend the friend to whose mum passed away you know her relationship with her mum was was complicated as often is our relationships with our parents so you know but she's she she was she was still heartbroken you know
Carly OsmanYeah.
Jennie CashmanShe's she was her mom at the end of the day and she loved her and and and like deeply but it was a complicated relationship so you know that I and I think depending on the relationship it's it sort of yeah I think it can be it it can be helpful to to to to be seeing a therapist, for example, where you can talk about all of it.
Carly OsmanThank you.
Jennie CashmanBecause, you know, you you might say something, I remember saying something to a friend of Abrams and he was so shocked when I said it, but it was just my way of dealing with what had happened. And I was just like, well, you know, if it had been the other way around, and I died, Abram would not be coping right now. And he was just like completely stunned that I said this out loud. And I was just like, well, it's kind of true though, isn't it? You know, it it would have been a total disaster. So, you know, was kind of me going, well, it's better. I suppose it's better this way around because, you know, i' I'm able to kind of deal with all the admin. And, you know, it was this it was it was a throwaway comment. but and a true comment but also I suppose it's that thing isn't it of like oppose two opposing things being true at the same time which is you know like I yeah I don't know I loved Abram to bits he was amazing but he was also totally chaotic and and I i if I could change what had happened, if if he you know if I could bring him back, I would, but I'm also incredibly grateful for the life that I've had as a result of him passing away.
Carly OsmanYep.
Jennie CashmanLike all of the experiences that I've had since 2012 are because he died. i wouldn't have had that life. I wouldn't have met those people. I wouldn't have had the experiences I've i've had if he hadn't passed away. And I'm so grateful for all of it. And it has been, you know, it has been tough and it's been amazing and it's been all those things that life is. And also, i wish he hadn't died.
Carly OsmanAnd this is what I think we need to talk about more. It's the ands that two things can coexist at the same time and they are both true and there's space for both things.
Jennie CashmanYeah, both opposing things.
Carly OsmanYeah.
Jennie CashmanI think that's the key, isn't it? It's like they're opposite, they're in tension with each other.
Carly OsmanYeah.
Jennie CashmanAnd and they're both true and I think that's an important thing just to remember for life generally it's like you know i've got client at the moment and he's he's struggling with with with conflict and dealing with conflict and and trying to understand what what his true opinion is when he can genuinely see both sides you know he's like I i agree with both sides I'm not really sure what what my opinion is and you're like well that's
Carly OsmanThank you.
Jennie CashmanThat's actually a good thing to be able to do that it would be great if if more of us could be like that where we could genuinely see the the benefits of both arguments or you know it's so but I but I think it's a tricky thing to to to get your head around for sure it's like wow you're grateful for the life that you've had because the person you love died and you wish they hadn't died
Carly OsmanYeah. Yeah. So, if Jenny, have you got any parting words for, God, that sounds take terrible.
Jennie CashmanBut but
Carly OsmanHave you got any, I can't even say final words. was not
Jennie CashmanIt
Carly OsmanHave you got any words, let's just say, whether it's their first Christmas or their 21st Christmas, it doesn't really matter to just how to get through the next month.
Jennie CashmanJust do you do you do what you need to do and don't don't don't worry about it it's just at the end of the day Christmas is a couple of days isn't it and i And I understand that the build-up is relentless these days. But I think just even if you're stretched, your work is super crazy busy and you've got kids and you've got no time for yourself, just try and find a moment or two, you know, fit for you and what you need if you're finding this time of year difficult. And I think probably the other thing I would say is It does get easier and amazing, magical things can happen when you least expect it.
Carly OsmanThank you. You're amazing.
Related conversations
Episode 21
Sex and pleasure
Why do we expect ourselves, and our partners, to just know how sex is supposed to work?
Episode 20
Making Money
What if making good money doesn't have to mean working yourself into the ground?