Wrong Way Forward
Well, bless your heart and clutch your pearls— She’s Katy Montgomery: Georgetown-educated lawyer, sought-after executive coach, and Southern-bred straight-shooter. He’s Justin Joseph: one time prosecutor, former Emmy-award winning investigative reporter, and her wildly opinionated counterpart.
These best friends are serving subpoenas to bad advice weekly with Wrong Way Forward - the advice column reboot you never knew you needed. Sparks fly. And, so does the hilarity. Join them as they turn questionable wisdom into a masterclass of smart irreverence.
Launching September 18th, we’re coming for the worst advice from the week’s hottest topics. Think of it as a public service: we suffer through the nonsense so you don’t have to. Sign up now - streaming on your favorite podcast site.
Wrong Way Forward
48. ONE Thing You Should Do Today (Before You Die).
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What if your obituary became the blueprint for how you live today?
This week on Wrong Way Forward, we sit down with Mary McGreevy, creator of the wildly popular Tips From Dead People (450,000+ followers), to explore one of the most unexpected sources of life advice: obituaries.
After reading thousands of obituaries, Mary has discovered that the people remembered most fondly aren't necessarily the richest, smartest, or most accomplished—they're the ones who made people feel something.
In this fascinating conversation, we discuss:
- Why most obituaries get it completely wrong
- What people actually remember after you're gone
- The biggest regrets people leave behind
- Why your obituary shouldn't read like a résumé
- How thinking about death can help you live a fuller, happier life today
It's funny, surprisingly uplifting, deeply moving, and guaranteed to make you think differently about what really matters.
🎙️ Watch the full episode on YouTube or listen wherever you get your podcasts.
Follow Mary McGreevy:
📱 @TipsFromDeadPeople (Instagram, TikTok, Facebook, YouTube & Substack)
📧 wrongwayforwardpodcast@gmail.com
📱 Text us: (720) 251-4450
Subscribe for new episodes of Wrong Way Forward every Thursday.
She's Katy Montgomery. He's Justin Joseph. These best friends are serving subpoenas to bad advice weekly with Wrong Way Forward. Now here's Katy and Justin.
Katy MontgomeryHey everyone, my name is Katy Montgomery, and welcome to Wrong Way Forward, where we roast the worst advice. And sometimes we try to give you some good advice too. I'm here with my best friend Justin Joseph and co-host, but today we are so excited to have Mary McGreevy join us. And Mary McGreefy is the creator and host of a popular social media site called Tips from Dead People. It has more than 450,000 followers. She holds an undergraduate degree from Notre Dame University and a Master's of Public Affairs and Public Policy from Law Follette School of Public Affairs at UW Madison. However, as Tips from Dead People has taught her, it's the little things that are the big things. So Mary would prefer that you know that she is punctual to a fault. And Justin and I can attest to that. She was perfectly on time. She's obsessed with tap dancing and has never had a cup of coffee in her entire life. She lives in St. Paul, Minnesota with her husband Ernest and their dog, Mr. Bane. And we are so excited to have Mary, who has been reading obituaries since she was a little girl. And so just to get started, Mary, how about you just tell us a little bit about yourself and how you became to love obituaries and the lessons you've you've taken from them?
SpeakerAnd how I found my community of fellow nerds online.
Justin JosephWe're happy to be to join that community.
SpeakerI know, of course. It's the best group. Well, let's see. I'm from Sioux Falls, South Dakota originally. And my mom, when I was a middle schooler, was the obituaries writerslash editor for my hometown paper briefly. It wasn't a great job, so it was a it was a short job. But I think it was the right age for me, and I started paying attention. And I started this hobby of reading obituaries, which of course I had no idea it would turn into a lifelong hobby or anything else, of course. But I think at that age, I was just reading because it was interesting to me. I was kind of and still am sort of a natural gossip and a curious person. And so I would look and see, well, if there's two husbands, why is the second one not mentioned? Or what does the phrase succumb to your demons mean? Like I wouldn't have known what that meant as a child. Um, and then I moved as an adult to, I don't know, five or six different cities, and I would subscribe to the print paper and cut out the obituaries that said something different or something unusual with no intention or purpose behind it whatsoever, just shoved them in a folder. And then a few years ago, I was in the middle of a big work project, like a work work project, and it was stressful. And I thought to myself, like, I don't have a creative outlet. I don't sing, I don't cook. I mean, yes, there's tap dancing, but hard, hard to bring tap dancing along on vacation or sit around a campfire and tap dance. So I thought, I'm gonna dig that folder out and see if it's still interesting to me. And if so, I wonder if there'd be any other people interested in it. So I did, and I I I do think it was really interesting. And I have three daughters in their 20s, and I asked them at the time, what platform do you think would be fun for this? And of course, if a cringe could be audible, that's the response I got. Now, of course, they're my biggest fans, but it was it was challenging at first. Um, so I just started reading excerpts, saying what they meant to me, and then slowly but surely people would start to send me good ones too by DM. And then one very strange video caught this algorithmic breeze, and I went to bed and woke up and had a million views and thousands of comments. And I think after that it started, I started getting put on faster highways. I still don't quite understand all the social media stuff, but it just sort of kept growing and growing. And then people would start to ask me to give speeches. So, but the last thing I'll say about this is that I think this whole hobby started out of curiosity about life, but I really think what is so meaningful to me is that it turned into a mirror for me to look at my own choices and my own life and the things that people always told me mattered in life, like degrees and jobs and esteem and achievements and all that kind of stuff. I would read obituaries where a person was traditionally accomplished, but it didn't come off that they were adored. Or conversely, I would read obituaries where you might charitably call them a hot mess, and yet this is the person that you want to talk to or have a drink with, and it was just like suffused or oozing with love. So it's it really for me, an anxious, sort of competitive person who never really found the professional lane that everybody said you'd find if you follow your passion. It was a great relief to see that, oh, there are different things that matter here. Because by the end of life, what is it? What is can we boil it down to the essence? So while it started off, I think just kind of superficial, people love stories, it has turned into something so much more meaningful for me, and I hope for other people. So that's a long background.
Justin JosephAnd so, Mary, what makes a good obituary? I mean, you've you've spent so much time with them. What's the one takeaway you have for people who may be considering this? What makes a good obituary? And should people be thinking about their own obituary?
SpeakerBoth awesome questions. I think for me, it's it's different for everybody. Some people don't care about the quality of an obituary. It's just like a task to do in the hubbub of after someone dies, and I totally get that. But for me, if you want to, if you're in the middle of the night, you're missing your person so much, and you want to somehow reclaim the feeling of being with them, a good obituary can make you feel once again that you're with them. And I think that has to do with authenticity. I know that's kind of like an overused word, but the good, the bad in between, I love it when an obituary gets really minute in its attention to detail, the things that they love, the things that they hated, the pranks, the habits, the hobbies, or whatever. That to me elevates to what matters the most. Whereas the ones that just you know feel like dumb LinkedIn or resume or whatever, I don't think people are gonna go back to that for a feeling of anything. When I now at this point, I'm getting sent like dozens and dozens of obituaries a week. And when I'm I try to read and respond to every single one, but when I'm thinking about what I want to share online, I think it's gotta be someone who's non-famous because we love our famous people, but they get a lot of attention. And it gets to the heart of the person, good, bad, and in between. So, like to the point of your podcast, there's a lot of like cautionary tales inside obituaries. And when I share those, I'm bracing for people to get mad. There's so much etiquette around death and so forth. And it's always the opposite. It's like cathartic for people to hear the truth in a story. And should people be thinking about their own? I think so. I think it's kind of fun. Like personally, I have uh just a note on my notes app that says she loved and she hated. And I feel like if I die tomorrow, people will have that list and they can run with it. But I of course, I love a funny obituary that's amazing. But there's also ones that are bittersweet and poignant and even savage that hold a lot of truth too. So I I guess I like the most when something doesn't feel templated.
Justin JosephYeah. We're talking today to Mary McGruby, who's the host of the popular social media channel, Tips from Dead People. Mary has more than 450,000 followers. Before we get too far along, Mary, where can people find you on Insta, on your other channels? And um, so that if they are interested, they can go to go to you now.
SpeakerI'm on all the platforms now. I started on TikTok, and that's when TikTok was growing, and then all the stupid political stuff happened with TikTok, and then it just kind of stalled. I don't quite know what's happening there. So I then at that point I was like, well, just to be safe. So I started on Instagram and Facebook and YouTube, and and then I'm playing around with writing. So I'm I started a substack too. So all of those places. I would say Instagram is probably the most active one right now.
Justin JosephOkay, and what's your handle on Instagram?
SpeakerTips from dead people on all of them. Weird, nobody else wanted that handle.
Justin JosephWell, just in case somebody's listening, is like I want to go see what this is about. And for people who don't know, basically what Mary does is she goes through obituation, she gives uh she takes takeaways from. Is that a fair statement?
SpeakerMm-hmm. Absolutely right. I think when I when I I'm reading through the submissions, because pretty much they're all submissions at this point. Um, I think would this have helped me at some point in my life? If so, it's worthy of sharing. Is it just really funny or really sad or well written? That's another criteria, I guess. But I feel like if it would help me to think again about what matters and what doesn't matter, then it might help someone else. That's usually the main filter that I have. And I I try to keep the videos around three minutes. So I do like trim things, I don't change what people have written, but sometimes you'll just trim the obituary down.
Katy MontgomeryYou know, Mary, um I had two parents who died unexpectedly. And so I wrote, you know, along with my sister, both of their obituaries. And then really I'm Catholic, and so in their funeral masses, even tried to take some liberty with the prayers of the faithful, but got in trouble with the priest. And edited. Well, I just, you know, I wanted to do some prayers of the faithful that were a little cheeky or that kind of brought out my parents. Um, there was one that was a little political and um they were edited back. But that led me to what you were talking about as kind of like the etiquette of death. And when we're kind of talking about the wrong way forward, a lot of times we talk about etiquette. Like, what etiquette rules are we just gonna, should Mary, should we just put to the wayside when it comes to death and grieving?
SpeakerI think, boy, there's little things to answer to that question, and there's big philosophical things too. Like, I mean, big philosophical questions. I think there should be compassionate choice in every single state, and I think we should broaden the parameters for what people can use. But in a on a like a micro level, I had the same experience. My mom died in November, and um uh the it was a Catholic Mass as well, and um the priest was amazing, he was great, but he did say, is it fair to say that she had she was in a lover's quarrel with the church for her adult life? And I was like, that's that is exactly fair to say for sure. So and we had the restrictions of whoever's gonna, they didn't really want people to give remarks, but if someone was gonna do it, it had to be this this small and so forth. But I think on a micro level, one thing that is fairly freeing is this etiquette around language. So we have passed away, we have loved ones, we have memorials, we have tributes. I try to stay away from all of those and just be really blunt about your dead, it's fun to make it's still okay to make fun of your dead person. Um they died, they didn't pass away. This is just a personal preference of mine, but I feel like if we can inject some of the earthiness and even humor, like the Irish do, for example, back into this process, people wouldn't be so scared of authentic obituaries. Like, why would we not share about the addiction? Why would we um not share about all the different spouses and so on? So I I really believe that it's refreshing to not use some of those euphemisms around death. So, yeah, that's good, and I that example is on my mind because I'm in the middle of writing a book. And that's I, you know, as you go back and forth with editors and so forth, I think the natural instinct for people when they think about anything around death is to tiptoe and to be really tender and not to shock people's sensibilities. But I am taking that language out and trying to insert blunter language in if I can.
Justin JosephAnd again, we're talking today with Mary McGreevy, host of Tips from Dead People. Um, she you can find her on Instagram and on various social media channels. Mary, when we'll come back, let's ask you about some of your favorite uh obituaries that you can remember, and we'll talk about that on the other side. We'll be right back with Wrong Way Forward.
Katy MontgomeryYou've been listening to Wrong Way Forward, where bad advice goes to die, and then gets resurrected just so we can roast it again.
Justin JosephIf you're enjoying the chaos, hit like and subscribe and come back every Thursday for new episodes.
Katy MontgomeryHave a new topic or some disastrously bad advice you want to dissect, email wrongwayforwardpodcast at gmail.com. Include your contact info.
Speaker 1Now back to Wrong Way Forward. Roasting the worst advice ever. Welcome back to the Katy and Justin Podcast.
Justin JosephWelcome back to this week's episode of Wrong Way Forward. We are talking to Mary McGreevy, who is host of the popular social media channel Tips from Dead People. She has more than 450,000 followers. It sounds like she's an author in making, talking about some of her best takeaways from obituaries. And Mary, talk to us about some of your most memorable obituaries that you have highlighted in your uh on your various channels.
SpeakerOne of my favorites, and she's gonna be uh the book that I'm in the middle of writing, it's gonna have 50 obituaries, and she's number one, is a woman named Trish. And by any normal metric, she was a job hopper, maybe didn't have a great work ethic, but it was clear from the obituary that she was a natural, intuitive parent and funny and so forth. But the last two paragraphs of her obituary were very simple. Here's what Trish loved, and it's a list of about 25, 30 things, and they're they're so small, it's Skittles, square shaped bullet points, the long and lean trouser from the gap, capri candles. It's like that level, all of them micro. And then the next paragraph is here's what Trish hated. Cold butter, Caillou, the PBS uh cartoon guy, um, people who are phony. So when I give talks to people and so forth, I always use that example as if you think about the metrics that we're all told matter, which is like achievements and honors and awards, and that's what fills up a lot of paid space and obituaries. This to me is so much better because if if the metric that matters to me, which is like who would you rather have dinner with, who would you rather have a drink with? Someone who's talking about KPIs and month over month revenue or Trish, and you could go down deep with cold butter and Skittles for 20 minutes. To me, that's like that's success. That is success. And I always feel like when I'm telling people that the little things in life are really the big things, as I'm saying it, I I cringe because of the cliche-ness of it. But she's a good example in the flesh, so to speak, of what that would look like and why that's actually the truth.
Katy MontgomerySo I love that you're talking about, you know, the typical obituary is like a list of accomplishments and what we kind of as a culture, you know, find important, certain milestones. Um if you were writing your own, would you just say, to hell with the education, to hell with the career, and instead, like you said, just do a love and hate list? Or would you mention, you know, those kind of highlights?
SpeakerIf I were writing my own, I would not include the education or the I mean, I have kind of a zigzaggy job history myself, so it's like whatever. I don't yeah, I don't I don't begrudge people that like I I read a lot of obituaries with that progress, that sort of straight line progress narrative in it. It isn't that I begrudge people that experience or how proud they are of it or how proud their family is of it. But if that's what defines someone, it feels kind of empty to me. So personally, I don't care. And I think my kids have heard enough of my videos that they get it, they will get that. But yeah, it's not that I would say listen to me and don't do any of that, because there's a lot of tenderness in that too. But um, I personally just don't care. It doesn't like that, doesn't I get to know someone that way.
Katy MontgomeryYeah, and I love that you're saying, like, you know, what really matters. And I do think if you're fortunate enough to be able to be with someone during the dying process, right? Where they can, you know, plan their funeral, talk about their obituary, is, you know, for example, we know Trish didn't like cold butter, but it would be great if Trish said, This is what really mattered to me, you know, like and you know what you're kind of bringing to mind is I don't know if you ever wrote Watch Six Feet Under, but I think about that very last episode where like Claire sees her life, you know, kind of a, you know, and it's not like you said, the accomplishments, it's the feeling, right? It's and so I I'm I think I might start a note section of things I love and hate too, but but what mattered? And and I think if we asked the average person, they would probably say family, love, relationships. But how do you articulate that, right? Or how do you show that? I think that's really interesting. It's what you choose to say, I think.
SpeakerI haven't seen Six Feet Under. That's a like a gap in my educational history. I think I should watch that. But I even remember in college reading Tolstoy's um The Death of Ivan Illich, which is the classic deathbed. I I am alone on my deathbed because I didn't tend to my relationships, I only worked. And then if you look at a variety of TED talks and things like that, the top five regrets of the dying, it's all of that theme. It's I did too much of this, I listened too much to what society was saying, and I didn't do enough of what my heart told me. I read an obituary recently for a woman from Berkeley who it was so poetic and and people really resonated with it. But it was basically like I at the too late, I started listening to that little voice that was inside me from a kid that was just suppressed. Too late, but I did it. I started listening to her, and after that, all these great things happened. And I think maybe even especially for women of a certain age, it was like she said what I'm feeling, she articulated this, and it's like she's articulating regret about what she was doing along the way. And I feel like that's just so helpful and great and special and unique.
Justin JosephSo do you often get asked to write someone's obituary? Like, do you get solicited for that?
SpeakerI never have. I mean, actually, so I shouldn't say never. I have in DMs. People will ask, do you help write? I'm so silly on social media. Like, I haven't really figured out monetization or anything like that. So I suppose I should at some point set up a hey, book 20 minutes with me or something. But I have never done that. So the first full obituary I wrote was last November for my mom.
Justin JosephAnd how was that process for you? I mean, because now you I would think you'd be in your head because this is kind of who you are.
SpeakerYeah, I know. Well, it's gotta be perfect. I think it went great. I do think that I come from a a little bit more traditional family. They're all readers and bookish and nerdy and progressive and that, but they do, it's like a it's it's more mainstream. So I feel like I stretched the form to the point of people still feeling comfortable, but also it felt kind of original. I did the love and the hate paragraphs, and people, that is the one thing people kept coming up and asking me about. So I think it's like tried and true now for me in my head. So it's like a realization that not everybody is gonna want David Sederis type of obituary. I love those kinds of things, but I understand that people are in an environment and everyone wants to be happy, and they don't. It's so hard to step out of that mindset that to be funny or brusque around death is disrespectful. And sometimes you just can't get there in the days after a death. But I've I feel pretty good about it.
Katy MontgomeryI I do. So, Mary, what's gonna happen with the death of the newspaper? I mean, I know we have like legacy.com. But you know, what you know what what's going to be the future? What's going to be the future of obituaries? And and you know, and you know, I don't know how old you are, but Justin and I are both in our 50s. Excuse me, I have my sister's dog here. But you know, when when I think about the future and like what is going to be the future of obituaries, you know, what is that going to look like? What if you had to anticipate, what do you see? Oh my gosh, we could talk about this for an hour.
SpeakerI know more about the business side of obituaries than a person should. So obituaries have gone back to the Roman times. It's only with the advent of the printing press post-Civil War that it became um part, a feature of your regular newspapers. And at first it was just for notables in the community who died. And then it got to the point where it became sort of like a classified ad. You're paying to sell your lawnmower and then over here in the same department you're going to pay for the obituary. And that's where it still sits in the majority of newspapers. It is a profit center and they are really reluctant to change the model and thereby in my opinion sealing their fate in the same way that Craigslist took away classified ads from newspapers and now Facebook Marketplace and everything else made paid ads for your lawnmower irrelevant. I believe that unless they change course the exact same thing will happen to newspapers because Legacy started its its business as the back end obituary provider for the Chicago Tribune. And then because it was the original because it was a good business model they started gobbling up newspapers to the point where they ended up with like 90% of the newspapers in the country. They are the back end repository of all the new bits for that paper. Legacy even is pivoting to try to get funeral homes to use their service and to tribute now they don't advertise it for 150 bucks you can go on and personally put something on legacy. They didn't ever advertise that before because it was shooting their newspaper partnerships in the foot. So the landscape has completely changed. There are startups out there like Epilog and Ever Loved and Keeper where you just go on and you create a free memorial kind of like the knot did change things for weddings. So I feel like right now in the heat of the moment people just put it on the funeral or the cremation home site because they get the sticker shots gonna be $1200 for a day to put it in your newspaper. So I think that's where it's going that's crazy. Pardon that's what obituaries cost my mother in law's obituary was $1200 for one day in the Dallas and particularly if you need to be in more than one newspaper right now.
Katy MontgomeryYeah it's crazy.
SpeakerMine would be Justin hated the $1200 obituary I know exactly and it's like a template that you're never going to see again. There are some exceptions. For example there's a community newspaper in Berkeley called the Berkeley side and they made a choice to have all of their obituaries for free. And you look at the obituaries on their site it is beyond it's colorful language it's long stories it is a true reflection of the community in the newspaper the old newspaper model if you were to look at say Detroit 1975 here's the obituary section it would not reflect the composition of the community because of all these equity issues around finances and literacy it's there's there's a huge equity issue in obituaries. But when a newspaper decides to make this free it changes the game completely. I I emailed the editor of the paper at the Berkeley side just to ask when you decided to do this did engagement go up? Did it go down? What was and he said it went way up so like if a publisher were to talk to me I would say if it's not already too late pivot to this I know it's so hard to give up a profit center but it's going to shrink anyway where you are still the center of history and truth of your community but it's seeping out and going away from them. I'm a I'm a diehard newspaper subscriber so I say this kind of with sadness but it is what it is.
Justin JosephWell Mary it's been such a privilege to have you talk all night about this I know tell us when your book is launching we'll have you back when your book launches how's that going it's I'm a first time writer.
SpeakerI I think real writers probably look at people like me with a large social media following like why did they get a book deal? They're not even a writer and I hundred percent agree with them I am not a writer but it's been really fun. So the book is um going to be 50 of my some of my favorites that I've shared over the last couple years and where the family has agreed um to have them in the book. And then I say about 300 words of commentary for each obituary um kind of like how I do online but just more literate. What when are you launching do you know yet or when the book's going to be released 27 August of 2027. But it's going to be done and written by the end of July of 2026 because I didn't know this about publishing they start marketing and selling a full year in advance.
Justin JosephWell we wish you the success of like a chicken soup for the soul franchise I hope you get 10 books.
SpeakerI would love that I used to make fun of that but now I'm like genius I would love that.
Katy MontgomeryWell thank you again for joining us amazing yes and just a few takeaways I think you know be real it's not about the accomplishment have people feel um and and continue to think about your own obituary and those that you love and let's let's take kind of this um shame or embarrassment or discomfort you know around and let's be honest in our obituaries. Let's say what we love and we hate. I'm going to start my list today, Mary.
SpeakerIt's it can genuinely change people's lives. Other people's stories can change your life all the obituaries that I've ever shared online there's a few hundred at least are at the link in the bio on any of these channels I just have them all reverse um chronological order and it's you know that's inspo. That's life inspo and it's writing inspo right there.
Katy MontgomeryI love it. Well you've been an inspiration thank you so much Mary it was such a pleasure we wish you all the success. Yeah and when we do social media we'll tag you and you know and all that kind of stuff um and so we'll go from there.
SpeakerOkay well I'm so glad to know about your podcast and let me know if there's ever anything I can do for you too. Thank you.
Justin JosephTake care bye thanks for streaming Wrong way forward the weekly reminder that advice is usually free for a reason. We call out bad advice wherever it hides boardrooms, break rooms and even book clubs.
Katy MontgomeryEnjoying this dumpster fire? Like subscribe and check back every Thursday for new episodes. Want us to roast your favorite piece of nonsense? Email us at wrongwayforward podcast at gmail.com. Be sure to include your contact info. We're not psychic just judgmental. And now back to Wrong way forward. Roasting the worst advice ever welcome back to the Katy and Justin and we're back and this is Wrong Way Forward with Justin Joseph Katy Montgomery and just a huge thank you to Mary McGreevy. I learned so much from her today and I think the conversation that Justin that she's having around death and being honest and making sure people feel and when you really show the essence of someone rather than the accomplishments that maybe we think what society expects it really gives us a chance to know someone to mourn to grieve and to remember how important they were in our lives. Love that let's give our first of just our top two or three that come to mind loves and hates oh yes okay loved for me loved um dogs for me I love I love that where you like you laugh so much you kind of fall over you know like you laugh with your whole body that's one of my favorite things. Love that any hates um I tardiness that's a big hate for me oh I I really hate lateness too but I would say you know I really really hate when you're on the I think I've talked about this a million times but I think it's so rude when there are two people on the sidewalk and there is a process for this and also people who have like a crowd of people or a dog and don't kind of get in a single file. They just think they have the entire sidewalk that that can really tick me off.
Justin JosephMy last love and I always say this is is about five o'clock in a pool when the sun is lazy and it's setting and it's just it's just it's warm but it's not hot. I love that time of day.
Katy MontgomeryI love it when a kid um when one of my nieces or nephews on another you know floor in a house and I hear Aunt Katy just yelling I love that.
Justin JosephWell we could go on and on maybe we'll do this at the end of each episode but we want to thank everybody for watching we're over time this week we'll see you next week on Wrong Way Forward bye everybody. All right that's a wrap on this week's episode of Wrong Way Forward. Remember the only thing worse than taking bad advice is giving it.
Katy MontgomeryIf you've liked what you've heard like subscribe or follow us wherever you stream podcasts. And if you've got a topic or need some advice will probably regret giving email us at wrongwayforwardpodcast at gmail.com.
Justin JosephThanks for listening to this week's episode of Wrong Way Forward