Our Messy Relationship with Money & Stuff - A thoughtful conversation with author Deidre Woollard

I’m a big fan of Deidre Woollard, Substack author of The Money Library. 

It’s hard to put Deidre’s work in a single category. What I enjoy most about her work is the way in which she navigates the very human tension between capitalism and what it means to be a thinking, caring human being.

As the owner of a small business I am constantly navigating the uncomfortable middle ground between my profit imperative and my desire to make a positive difference. This conversation will give you some good questions to consider when it comes to your own middle ground.

Hang out with Deidre at The Money Library on Substack.

If you find the Marketing Root Work podcast valuable, please become a subscriber! 

My mission is to change the way small business owners market themselves and it’s very important to me that I reach as many people as possible.

Transcript

Judy Murdoch

Hello and welcome to the Marketing Root Work Podcast. I am your host, Judy Murdoch.  


Deidre Woollard

I'm Deidra Woollard. I am a financial writer, financial podcaster, tax prepare, declutter, financial literacy coach. Just at this point in my life, I'm sort of a bunch of different things that I care about. 


Judy Murdoch

So you're somebody who kind of like helps people like get their shit organized.  


Deidre Woollard

That's really the underlying thread. Figuring out people's relationships with their finances, with their stuff, with how they live their lives and you know, just trying to help where I can. Sometimes it's as simple as understanding what you're bringing into the house and or as complicated as figuring out if you should have a Roth IRA. 


But it all comes down to understanding your own motivations. And I think that's the thing I'm working on personally, is that so much of what we think we should be doing is coming from outside. It's not coming from inside.  


Judy Murdoch: 

Totally agree. 


So I don't know you well, I know you primarily through your Substack, but it sounds like you have this really interesting work background and so I'm wondering if you could share a little bit of your journey with the attention to what, what are some of the, like what's the gold thread that seems to connect everything for you? 


Deidre Woollard

Yeah, my first like grownup job was as a workers' comp insurance adjuster, which, um, I still have friends in that industry, but then worked in magazines for a little while, went back to school, um, got an MFA, which, you know, whatever it was, was a great experience, but not necessarily preparing one for something. 


And I. Sort of came out of that at the time that professional blogging was starting. And so at that time there was Gawker and Weblogs Inc. So I ended up meeting Jason Calis, who was, um, doing Weblogs Inc. With, uh, Brian Alvy. And so ended up being a professional blogger. With them through being bought out by a AOL. 


What I did there was write a luxury blog. So I was doing a lot of real estate stuff. Wow. First estate of the day online. So then after that went to realtor.com with their social team. Did that for a while, uh, transition from that into working for a couple of  high profile real estate brokerages in Los Angeles doing, uh, 


Judy Murdoch

Okay. 


Deidre Woollard

Marketing work, content work. Promoting celebrity homes, things like that. All very exciting stuff. So, uh, also did some writing on commercial real estate. Uh, eventually worked with the Motley Fool for, uh, just about five years, which brought me back to the East Coast. And then I've just sort of been doing my own thing for a little while. 


Judy Murdoch

I just wanna say what a great background do you have. 


Deidre Woollard

Thank you. 


Deidre Woollard

Doing some of the real estate stuff was, was really fun. And I still sort of, I think that may be a, that that's kind of a thread of understanding people's relationships with real estate, both financially and sort of it's this emotional decision. 


It takes up so much energy of, you know, our houses do.  


Judy Murdoch

Yeah, I agree. I've lived in the Denver area since 1999, so for over 25 years now. And the, the Denver real estate market from the very beginning, um, it's very expensive. It was really expensive when we moved here, and that was relative to living in the city of Chicago, which is also a very expensive market.

It feels insane to me personally. When I'm seeing little bungalows, like two bedroom bungalows that are going for over a million dollars. I mean, that is just. Like, you're on the East coast, you've been to Los Angeles, so I'm sure you've also seen some really crazy pricing, but there are just days where I look at it and I'm just like, they, they must have screwed up a comma. 


Like no way. You know? How is that even possible?  


Deidre Woollard

Well, that's one of the weird things in this country is that the same piece of real estate, depending on where it is, is you know, is 200,000 or, or 2 million, and that's, you know, we sort of live with that knowledge and we don't really think much about it. 


But when you actually think about it. It's, it's kind of bizarre.  


Judy Murdoch

It's always been that to some degree, right? 


Deidre Woollard

 Yes. Yeah. 


Judy Murdoch

I mean, like for example, Manhattan has always, always, always been very expensive to live in with some exceptions and with rent control and that type of thing. Um, but it seems a lot more widespread now. 


And I'm beginning to think about retirement and downsizing and just living somewhere a smaller, more simple life. And, um, it's really daunting to try to find that, you know, unless like I really wanna live somewhere where I don't think I would be happy. 


Deidre Woollard

One of the things I think I'm thinking about is, are the advantages of cities the same that they were 20 years ago? 


Judy Murdoch

Mm-hmm.  


Deidre Woollard

Are they the same for young people that they were when I was in Boston and in my twenties and real estate was expensive, that was okay. You live with a bunch of roommates, you make it work and you know, but, but part of the benefit I was getting was going out with friends or being in a place where there were lots of other jobs and I'm not sure that today's young people. 


Are getting as much of the benefit of being in cities that we did back way back when.  


Judy Murdoch

I agree. Um, I know living in Chicago in my twenties and early thirties, I had a blast. Yeah, it was, it was just a great place to be. Um, I had a good job, so that was definitely supporting me. But I had student loans, which you may be able to relate to. 


Um, so that was taking up a big piece of my paycheck. But, you know, I was just telling my husband, who's also from Chicago, that we just have so many good memories of going to clubs and going to restaurants and mm-hmm. All the, the weird, quirky little things that you could find in Chicago because there were. 


Just a lot of, uh, creative people out there, a lot of people doing interesting things, and it was just a, it was just a fun experience.  


Deidre Woollard

Well, one of the things I think about too is the fact that younger people aren't, aren't drinking.  


Judy Murdoch

Isn't that crazy?  


Deidre Woollard

It is. It is an interesting phenomenon that, you know, now we have a little over 50% of people. 


I think it's like 53 or 54% of people drink, which is like the lowest number. And for young people it's even lower. There was a stat I heard recently that in the eighties and nineties, young people had tried alcohol by the time they were in eighth grade and now it's high school. 


The same level.  


Judy Murdoch

Wow. So do you think some of it is like, because like marijuana is like widely available and so people smoke pot instead?  


Deidre Woollard

I think that, I think that's a lot of it. I think, yeah, vaping culture is a lot of it. And it's also just. I think people are home with their computers. I think there's less running around and getting into mischief. 


It's good that kids aren't drinking and driving, but there is some loss of social communication. 


Judy Murdoch

I agree. 


Deidre Woollard

And, and the stupid things that we get up to when we're, when we're young and drinking.  


Judy Murdoch

Well, I did a lot of stupid things when I was young and drinking, but I don't really regret too many of them. It was fun. 


So in talking about wealth discrepancy, I don't know what generation you are of. I am the very tail end of the boomers. So my childhood and teen years were in the sixties and seventies. When I graduated from college in the early eighties, there was a recession. I also had a ridiculous major. 


I was a marketing major, but I had just this obsession with, I had to do consumer research. That was it. I didn't, so, because I wasn't willing to do sales, I couldn't find a job. If I wanted to sell, I could have easily found a job, but I didn't wanna sell. I wasn't willing to. So it took me a while to find a job, but. 


What I remember at that age and as I was getting older, was I always felt that opportunity was there. I always had a sense of expansiveness and opportunity. I don't know if I was ever looking to surpass my parents in terms of their achievements, but I certainly felt like the future that I desired was within my grasp if I was willing to work hard and be creative or do whatever. And I don't feel that way today and I don't think it feels as much that way-- I have a 30-year-old son, and I don't think it feels that way to him either. I'm just wondering, what's your take on it? 


You read a lot and I'm just sort of curious. Again, like what threads or trends do you see that are contributing to the way things are currently?  


Deidre Woollard

I think there's so many things. So, um, I'm a little younger. I was, I was, I'm sort of the very start of Gen X, so, okay. I grew up, uh, mostly in the seventies and eighties, so 

Was working late eighties, early nineties. In that transition from in an office to, in an office with computers? Sort of, yeah.  


Judy Murdoch

Yeah.  


Deidre Woollard

Just as emails started, just as you know, one of my first jobs, um, after the workers' comp thing, I was in a, um, a computer reseller that sold like, that, did like outfit, conference rooms and things like that. 


So did marketing proposals for them. But it was a very different world in terms of technology and I always felt like if I just learned more things and I worked harder things would fall into place.  


Judy Murdoch

Yeah. That's how I felt too.  


Deidre Woollard

It's not that I felt like it was a completely level playing field, 'cause I certainly felt that there was some sexism but I felt like if I worked hard, if I found the right mentors that there was a path. 


Judy Murdoch

Yes. 


Deidre Woollard

And I think that's what's missing is that now it feels kind of up in the air for a lot of younger people. 


Judy Murdoch

Yeah, it does. 


Deidre Woollard: They're floundering. They don't know. There's not really a path and there's not really a way to succeed. 


And what's happening with AI, it's only at the beginning and it's just knocking people off their feet. In content, in marketing, in SEO, like so many of those jobs are just shifting and changing so fast, and I'm seeing all of these people with real talent in their thirties, are all of a sudden not able to get a job. 


And it floors me.  


Judy Murdoch

 Well just as a note of what my son is experiencing. Um, he had a, he has a degree in computer science. Um, he got some really good jobs, really well paying jobs and at some point one of his employers just said, sorry, the project that we hired you to do, well, it's not working out. So it's been real and have a good life and take care. 


And he has been, to his credit, really giving a lot of thought to sort of, well, what do I wanna do, you know, in the world. Um, he was fortunate in that he's a person who really saved his money. So he's been able to, you know, live pretty much at the standard he'd been living at. And he had, he sort of has the space. 


To do the research and not worry about having a job. But he decided finally that he's gonna go back to school and get a degree in counseling. And I actually think that it's a pretty good decision on his part. I think for one thing, he'll be really good at it. And for another thing, there's no shortage of people unfortunately who need Mental health assistance. 


So like he's in some ways kind of a poster child.  


Deidre Woollard

Well that healthcare thing is where I see a lot of people going because that just is one of the places where jobs continue to proliferate and we'll keep doing so because we're all getting older. 


We're all gonna need more healthcare of all kinds of varieties. 


Judy Murdoch

That's right. Good point. 


Deidre Woollard

That's part of the trend. But there's also what you mentioned and I had talked about it on my substack and you commented was that idea of the. If you work for a company and then they decide whatever it is they hired you for, they don't need anymore. 


And that just happens over and over again now.  


Judy Murdoch

Yeah. 


Deidre Woollard

And I did not used to see that happening. And I think that's one of the biggest shifts. And it sort of started in the early two thousands and just has continued to grow because as these tech companies get bigger. Or even as startups get bigger, they hire you for one thing and then they go and do a different direction because they're more, there's more money there or something like that. 


So it ends up where people feel like they're in this constant state of, of disruption and 


Judy Murdoch

Right. 


Deidre Woollard

It's really hard.  


Judy Murdoch

So, I have a question for you. I wanna hear what your thoughts are because part of me gets that technology tends to be pretty fast moving. I mean, that's just sort of the nature of the business. 


There's always a lot of research being done. There's always changes happening. Technology is changing all the time, and so it's very disruptive. And I get that. And I also get that there is a need. If you work in technology, you work in technology to be adaptive and flexible in the way that you work. 


And in your most recent substack post, it was about a woman who worked in tech. It sounds like, from what I read, that she, she did her absolute best to be adaptable, to make things work in a way that was from what, in my opinion, was very gracious. I don't think I could have been that gracious if I had been in her shoes. 


And there's also this issue with. How we are as human beings, meaning that as human beings, we have a lot of capacity for being adaptive. In some ways human beings are amazingly fluid and really able to adapt very quickly. It's probably one of our, it saving graces as a species, but. 


You know, having read, read what you wrote about this book in particular, I just kept thinking to myself, you know, at what point is it just ridiculous? At what point is it that pivoting? It's a word I hate by the way, but, you know, we use it. But you know, like doing a pivot like twice a week or three times a week. 


What is it just kind of like really. Is that really necessary? 


Deidre Woollard

Yeah, so the book is a exit interview by Christie Coulter, who worked at Amazon for about 10 years. And she talks about all of the different parts of Amazon that she worked on and all of that. 


And I feel sort of struck by this both because I'm, you know, I'm an investor and I'm also a human being and I feel this, this, this tension between those two. Because as an investor, I want a company to keep growing, keep going in the directions that are making money probably and, you know, and thrive. 


That's otherwise none of us make money. But I'm also so aware of the fact that those are people, you know, I've been, I've been through a corporate layoff. It's not pleasant. And it's very hard to pivot when it's not your choice. Because if you're an entrepreneur and you're running your own business and you see the need for that pivot and you make it. 


It's much easier when someone else from, you know, infinite layers above you says, we're going in this direction. And that thing you just worked on for a year is now dead. Don't speak of it again. That is really hard.  


Judy Murdoch

Yeah, agreed. Been through it. It's very painful. During the.com bust in the early two thousands I was doing technical writing. 


Which is something I still really enjoy doing, and I worked for, I think maybe five different companies. In every single company, I was hired a couple times as a full time employee. The other things were consulting. But in all cases, I was hired to like, create something, you know, like training materials for a new system or whatever it happened to be. 


You know, something new was coming in. It was an initiative, and my job was to do whatever documentation, training, whatever kind of communication materials. Were needed in order to help people use the new system. And in every single case, I probably got fired within six months. Not because of anything I did. 


They were all very apologetic, like, you do great work. We're so sorry, but because in one case, they just closed the Denver office, they just said, you know what? You guys are expensive and. We're gonna close the office. In another case, the company had like one, you know how that is? 


Like, they have one client, one client that's really keeping them going, and the client just said, we're sick of you guys. 


Deidre Woollard

Oh yeah. 


Judy Murdoch

If this hasn't happened to you before, it sounds incredibly harsh and it is, but I went through this five times and that was actually my impetus to become a business coach. 


'cause I finally felt like I love tech writing. I really do. And I still do it, but, you know, I think there's something I could do that would make more of a positive difference in people's lives. And so that was really what pushed me into coaching. 'cause I just thought like how long do I wanna be doing this? 


And going through this.  


Deidre Woollard

Yeah, I could definitely understand that. I mean, I feel that way to some extent certainly about writing because I mean, there was a point where I was my husband found recently my old blogging contract from like early two thousands, I was supposed to blog like 325 posts a month. 


That's crazy. I don't know how I was doing that. 


Judy Murdoch

That's insane. Oh my God. 


Deidre Woollard

That's how it was in the early era of blogging and none of that, and this is all way before AI or anything else, you would just find a story, write it up quickly and keep going. Now with ai, I mean, I've sort of felt like for the last few years I kind of felt like John Henry and the steam engine where AI was just coming and coming. 


I can't outright it.  


Judy Murdoch

Yeah, yeah.  


Deidre Woollard

I could be a freelance writer for other publications at this point, and I just couldn't make myself do it. 


Judy Murdoch

Yeah, I hear you. No, I hear you. 


Deidre Woollard

I love to write, I still write and I write for things that I care about, but that hustle, that engine, yeah, I couldn't put into it anymore. 


So yeah, I think that's why I've found other ways to really be connected to people, because for the last 20, 25 years. Most of my time was, most of my relationship was with the computer, and now I really get to talk to people or work in people's houses or have conversations in person, and that matters to me. 


Judy Murdoch

Okay. Yes, and I totally agree. I also, being with people as. Probably my favorite part of what I do. If people were not involved, I wouldn't be doing this. I'm thinking about a couple different places to go and I'm gonna let you decide which way you wanna go. 


We can continue talking about sort of. Kind of our extreme capitalism. Um, we can continue talking about that. 'cause I'm, I'm again interested in hearing more about your thoughts about it. Another place we could go is, I know you do personal organizing for people, and I know too, there's some really interesting stories. 


There's something really important in there that tells us sort of about the human condition and our relationship to stuff. I find both areas really interesting. Where do you wanna go?  


Deidre Woollard

Let's talk about stuff, because I love to talk about people's stuff and I'm a person who has like, no stuff. 


I'm a pretty hardcore minimalist and, my father was a minimalist. My mother is definitely the opposite and. I'm in people's houses. I've been working with a franchise called Caring Transitions, which helps people 


Do estate cleanouts and things like that. 


So I've been in a lot of people's houses. I see the same stuff over and over again and I see the same problems over and over again. And just about every friend of mine that I talk to. Tells me about how their parents have too much stuff and are trying to give them old China and old Crystal and they don't have room for it. 


So this is a problem that I see on such a massive level, and I have no idea how we're gonna fix it.  


Judy Murdoch

Yeah. What do you think contributes to that? Like how do you think we got there?  


Deidre Woollard

Part of it is that people took the stuff from the previous generation and never got rid of it. I have gone to people's houses that are senior citizens moving to assisted living. 


And they have boxes of their mother's China that they never used, but they still have it. 


Judy Murdoch

Oh, interesting. 


Deidre Woollard

And so we have that obligation. So much of it, so much of the things we buy. Yeah. Or the things we keep is about obligation and feeling like we owe the person who gave it to us or something like that. 


It can be as simple as, you know, everybody gets stuff they don't want for Christmas and so many of us keep it. Yeah. It's like you don't, you don't have to keep it. It's awesome. Someone gave you something, but if you don't, if it's not for you. You can donate it, you can sell it, you can let it go with love. 


Judy Murdoch:

Yeah. I'm gonna make the assumption you read the book by, I can't remember her name now. She's the woman, she's Japanese.  


Deidre Woollard

Oh, the Maria Kondo book, correct? 


Judy Murdoch

Yes. Yes. I'm assuming you read that.  


Deidre Woollard

Yeah.  


Judy Murdoch

Yeah. And I thought her idea of giving away anything that doesn't spark joy. I thought that was like a brilliant idea. 


I really liked that. What I have found myself in trying to put that into action is that giving away something, even if you never use it, as you said, it can feel really difficult. It almost feels like I was given something to take care of and I'm giving it away, like betraying somebody almost. 


I don't know if that's quite the right way to say it.  


Deidre Woollard

I've had people say that to me before. 


Judy Murdoch

Like you're betraying the relationship or something. Related to what you said, so when I got married. I, in my registry, I asked for everyday wear. I did not want China. I don't really entertain, um, China, I always, I have so many memories of my mom, like washing the China on polishing the silver, and I just thought, man, you know, I don't wanna have to have that kind of  


Deidre Woollard

Yeah. 


Judy Murdoch

Obligation. So I got every day where, which I use, which makes me happy. At some point, my mom was getting rid of things that belonged to her mother and she said, you know, grandma has like these boxes of really nice China. Do you want them? And I thought, well, I don't have any China, so sure, why not? 


You know, send, send me Grandma's China. So my mom sent us my grandmother's China, and what was so funny about it was it promptly went into a storage space. And I never looked at it again.  


Deidre Woollard

Yep.  


Judy Murdoch

And so finally I did give it away and I didn't feel bad about that, maybe because it was my grandmother's, not my mother's, but I know too, like my mom has a ton of gorgeous bone China and silverware, and it's just like, I don't want it. 


Deidre Woollard

And unfortunately so much of it is now flooding the markets that things that people paid a lot of money for. Aren't worth what they used to China, because there's so much of it. So even the name brands, like a limo or a Lennox isn't worth what it was. The brown furniture, I mean, I love beautifully made brown furniture, but the big China hutches or the big sideboards, or the big headboard and the bureau and the dresser, that whole set. 


You can't give it away. It's just people don't want it anymore.  


Judy Murdoch

That's heartbreaking, isn't it? 


Deidre Woollard

From a craft perspective. Yeah. 


Judy Murdoch

The quality from the craft perspective is where I'm speaking. Yeah. That is very, very interesting. That gives me so much to think about. 


Deidre Woollard

It's something that nobody thinks about it until they have to.  


Judy Murdoch

Maybe that's part of it. Nobody wants to have to think about when they have to give it away and can't use it anymore.  


Deidre Woollard

Well, and some of it is, there's this thing called Swedish Death Cleaning, which is the idea I've, that idea that you tidy up your life, not just your, it's your stuff, but it's also your financial life. 


You make everything as easy as possible for the next generation.  


Judy Murdoch

Mm-hmm.  


Deidre Woollard

And some people really, really get attached to that. And some people really have, you know, I don't wanna think about death, I don't wanna death clean. That sounds awful to me. So, it depends on how comfortable you are with the idea that you're not gonna live forever and, and you know, your stuff isn't going to remain in the state that it is when you have it, it's, it's gonna go somewhere at some point, you know. 


Judy Murdoch

I think it makes me think also about in our culture that we just don't really have as much space for death and the end of life. 


Deidre Woollard

True. Yeah. 


Judy Murdoch: You know, we just don't really think about it very much until, as you said, until we have to. And I think that that's always been the case. Um, at least I think, you know, for the 20th century and certainly in the 21st century, largely because the child mortality rate has decreased so much. I think it's always interesting that before the 20th century, before antibiotics, people had huge families and they would feel fortunate if half their kids made it to adulthood.You know, we just, we don't, we live in a time where children are dying from measles and whooping cough and scarlet fevr, all these things that killed kids. 

And so now we have like just a lot of kind of elderly people. And there's nothing really in our culture. I mean, I'm elderly, you know, technically. And I don't feel like there's any messages in the culture unless I very intentionally start going to depth cafes or something like that where people talk about the fact that in 20 years you may not be here, you may not be here on planet earth. 


There's a really good possibility of that and it feels like a conversation that needs to be had.  


Deidre Woollard

It does. There is that, that holding on aspect of things that I find not just with the physical objects in your house but also with money, especially with older people not wanting to share the details of their financial lives with their own families. 


We're taught not to talk about money. You'll hear people say like, oh, you'll get this when I go, or something like that. And it's like,  


Judy Murdoch

Yeah, yeah, 


Deidre Woollard

No, talk about it now. Talk about it with a financial professional, meet with A CFP and, and go through it and meet with an estate lawyer. Help your family understand that stuff. 


I mean, I was lucky. My father died when I was pretty young. I was 28, he was 55 when he died, so, uh, a little younger than I am now. He was very good at doing that for me, like took me to meet his financial guy, took me to meet the lawyer, showed me what was, what was going on. I mean, because he knew, it was a form of cancer. 


He knew we probably wasn't gonna live that long. But because of that, I think it sort of prompted him to do that. But in situations where people live so much longer, 


Judy Murdoch

Right? 


Deidre Woollard: They don't feel like they need to talk about it. They don't feel like they need to share it. It's not their child's business at this point. 


It'll be their, their business to deal with later. But then you never know what's gonna happen. So, 


Judy Murdoch

Yeah, 


Deidre Woollard: I feel like getting comfortable with that and having those conversations is important. A friend of mine, Beth Pinsker, wrote a book called Your Mother's Money. Really, really good book about her experience. 


Dealing with her mother's financial picture.  


Judy Murdoch

Yeah, I agree. You know, I was fortunate that my dad, like your dad was extremely forthcoming. For whatever reason, he genuinely seemed to enjoy kind of bringing me- I've got two younger sisters- sort of into the details, so I had a chance to meet his financial planner and my sister's actually a CPA and so she was able to sort of take things over. 


We were lucky that we had a dad like that, who really trusted us and wanted us to get involved.  


Trust. Yeah. The idea of trusting people is sort of the underlying threat of all of that.  


Judy Murdoch

Yeah. I'm thinking about if it were up to me, it's not of course, but if it were, I would really like to see more movement in terms of just getting people thinking more about the fact they are gonna die. 


To think more about their legacy and to think more about the fact that you're not always gonna be healthy, you know? 


Deidre Woollard

Yeah. 


Judy Murdoch

And not in a negative way. I think more in a way of just acknowledging our humanity and the fact that we have human bodies and they don't go on forever. I just think there's a lot of grace in that. 


Deidre Woollard

Well, and in terms of a entrepreneurial perspective too. There are gonna be so many businesses that come up out of this need to help people who are 80 plus deal with life. 


Judy Murdoch

Agreed. 


Deidre Woollard

We've never had a population of this size and age in written history. Hasn't happened. 


Judy Murdoch

Yeah. 


Deidre Woollard

We're seeing a little bit of it through Japan, which is a bit ahead of us on that, but also that's a much smaller population and a, and a much more homogenous one, so 


Judy Murdoch

Correct. 


Deidre Woollard

What we're going to be seeing is something really phenomenal and I don't think we're prepared for it because it is so hard to confront. 


Judy Murdoch

It is, and fingers crossed, maybe this is something I need to be involved in more. 


That it is done from a very humane and loving perspective. It doesn't have to be religious necessarily, but I would like it to be something that is very humane and caring and focused on that we are human beings with human needs. And one of my biggest, I guess, complaints about the current situation is that most assisted living and nursing homes are for profit. 


And I am not anti-capitalist. However, I do think that in places where compassion, kindness, and this really deep need for human beings to just feel deeply connected to others, to feel loved and appreciated. There's gotta be a better economic model for that. 


I don't know if it's not for profit. This is not my area of expertise. What I do know is I don't think for-profit assisted living spaces do a very good job serving the various people who are involved with them. So not just the people who live there. 


Deidre Woollard

Yeah. 


Judy Murdoch

But the people who work there, it's just kinda like, no.  


Deidre Woollard

There is a stark difference between retired life you're going to have depending on how much money you have. 


That is unfortunately where we find ourselves. 


Judy Murdoch

That's true. 


Deidre Woollard

So people who work at higher end assisted living places get more salary, get more benefits, get they have a nicer working environment and that makes them happier so they're nicer to the people. And unfortunately the opposite happens on the other side. 


And one of the things I'm passionate about, and one of the things I see is older women on their own- especially women with, without children or without a support system and 


Judy Murdoch

Mm-hmm. 


Deidre Woollard

How we find our way. A lot of my friends have that idea of like, well, we'll just live together when we get older. 


Judy Murdoch

I know some older women who do that. 


Deidre Woollard

It, it may come down to that, we'll just get a house and we'll hire help together and we'll figure it out somehow.  


Judy Murdoch

Yeah. I know some older women who did that. In their particular case, it worked out really well. They were very intentional about it, and they were probably very like-minded and their values were probably very similar. I have seen when that works and it can be really cool.  


Deidre Woollard

Yeah, there's always a way to figure things out. The world is unfair and I'm probably pro capitalist, but I also see the problems of extreme late stage capitalism, which is where we find ourselves. 


Judy Murdoch

Yes. 


Deidre Woollard

And I know that our superpower is our ability to connect with people, to band together, to pool our resources, to figure things out. That's what we've got.  


Judy Murdoch

Agreed. Agreed. Yes. Okay. Cool. So on that note. I wanted to ask you because you read, you read so much. I mean, that's like your whole substack. 


Deidre Woollard

Yeah. 


Judy Murdoch

Tell me some authors or resources that you especially love. You know, ones that like, they're doing it right or they've got something really good to say.  


Deidre Woollard

Oh gosh, I don't know. That's, that is a hard one. 'cause I read okay. I read so much. 


I read a lot of new stuff that's coming out. Most of the stuff I read is on money, business bios, capitalism, things like that. So, that's sort of the field in which I learn, and it's not necessarily stuff that's a lot of fun for other people to read. 


Judy Murdoch

I just wanna say this, Deirdre, that you make these topics really interesting to me. I think because you do have that focus on the human element. And you, you manage to make, you know, some topics that I would otherwise find yawn inducing and dry. 


And when I read them I get pulled into it. So I think it might be like you're able to take your own interest and enthusiasm for the topics and you're really good at bringing that out in your writing so that other people get interested as well. 


Deidre Woollard

Yeah, and there's some writers that do that really well. Like Andrew Ross Sorkin, his new 1929 book. Nobody really wants to read about that crash. But he's really good at taking you to the place. So you're walking down the street with this businessman in 1929, seeing what's happening in real time. 


That really brings you in. So many people have this resistance to money, and yet we're all forced to deal with it and it's so uncomfortable, especially I've noticed for women, I and I come from that place of having that I'm a creative brain. I got an MFA, not an MBA, I don't. 


Judy Murdoch

Right. 


Deidre Woollard: You know, all of this makes me a little nervous and a little unsettled. And so, you know, when my father taught me about money. Sort of early days of the internet, there was the Motley Fool on a AOL but there wasn't a lot of other stuff. So I just sort of had to learn it through the stories. I would get an annual report back when they used to print them and they were beautiful. And I would read the story of the company and I think, okay. I understand what this company does, these numbers at the back, I don't really understand them at all. But if I understand what the company does,  


Judy Murdoch

Yeah.  


Deidre Woollard

Then I can start to think. 


Then I can get more comfortable with the idea of looking at the numbers. The numbers are telling me, the backup to the story I've learned.  


Judy Murdoch

 That is a really, really great way to look at it, and it's very interesting because if you were a number person, my sister's A CPA, and she's very much a number person. The numbers speak to them. 


Deidre Woollard

Right. 


Judy Murdoch

The numbers come alive for them. They bring the organization alive for them by looking at the numbers. But our temperament is different and we wanna see the human side of it because that's just what our brains work with. So that's a really interesting way to look at it. 


And you're right about Andrew Ross Sorkin too. I've heard some podcasts with him and he's great to listen to.  


Deidre Woollard

Yeah. Yeah, he is. And that idea of writing versus money it's interesting, because at the Motley Fool, we talked a lot about that. What makes a good investor? 


Do you have to have an econ background? Do you have to have a math background? 


Judy Murdoch

Mm-hmm. 


Deidre Woollard: And a lot of the great investors said, no, you need to understand history. You need to understand cycles. 


Judy Murdoch

Mm-hmm. Mm-hmm. 


Deidre Woollard

You need to understand 


Judy Murdoch

Yeah, agreed. 


Deidre Woollard

How the world works, how people work. You need to understand psychology because so much of what's going up and down in the market is psychology. And so it's really interesting to think about investing as being much larger than numbers.  


Judy Murdoch

Yeah. One of the areas that always appealed to me was the idea of value investing, which sometimes people make it sound so complex, but what always made sense to me was just looking at the company and asking the question, what do they do? 


What do they make? And where's the value in it? Like, is there a value story in it or is there not? Is there just like a story that somebody wants to have? So for myself that always made sense that companies do, for the most part, create value. I mean, that's how you make money. 


If you're not creating value, then you know, I would be a little worried about your valuation, right? So like I think it's one of the reasons people talk a lot about the AI bubble. Right now, we're not sure where the value is other than the fact that all these data centers are being created right now. 


Deidre Woollard

Oh yeah. Yeah. As someone who lives in Northern Virginia. Yeah. I see a lot of those data centers and yeah. The valuation for AI is tricky. I mean, for the last few years it's been the, you know, whatever they call it, the magnificent seven, then it's the magnificent five. Then it's the FANG stocks, whatever it is. 


It is not, you know, it's not Coca-Cola, it's not, it's not some company that makes, you know, it's not fastenal, which makes like screws and things like that. 


Judy Murdoch

Right. 


Deidre Woollard

It's this unknown thing that we don't really know how it's gonna play out, but oil. 


Judy Murdoch

Exactly. 


Deidre Woollard

Boy oh boy, we gotta shovel all the money and all the power and everything at it. 


Judy Murdoch

Right. Exactly. 


Deidre Woollard

And we don't know where that's gonna lead and there's no  


Judy Murdoch

Right.  


Deidre Woollard

Real proof that it's going to lead where people say it's gonna lead. So much of this 


Judy Murdoch

Agreed. 


Deidre Woollard

Is, is hype.  


Judy Murdoch: It's speculation.  


Deidre Woollard

Yes.  


Judy Murdoch

Several people have said it reminds them of the early internet days. But I felt, even back then, the internet itself, I always felt that the value was pretty obvious in terms of what the internet enabled people to do. 


And with ai, they have ideas about what AI will be able to do at some point. Currently, i'm not seeing it. And there's a lot of questions in terms of when they will get there and where "there" is exactly.  


Deidre Woollard

I think a lot about that for the.com bust, 'cause that was my first experience as an investor. 


Judy Murdoch

Yeah.  


Deidre Woollard

And terrifying. Panicking. I had no idea that this was a thing that could happen. And it took about 10 years for companies like Microsoft to come back from where they were. And that was a hard period to go through. Is it gonna happen like that again? It may. And I think that's one of the things that I've learned in understanding the psychology of money is we're so caught up in recency bias that we can't understand that there may be a period of time in which things stagnate for a while. 


It's happened before, it may happen again. And we have to be prepared for that.  


Judy Murdoch

And there's disruption. You really never know where it's gonna come from.  


Deidre Woollard

Yeah.  


Judy Murdoch

You know, who knows? Alien Technology, who could say. That'd be cool, right?  


Deidre Woollard

Yeah.  


Judy Murdoch

So, Deirdre, having said what an awesome author you are, how can people get in touch with you? How do they get an opportunity to experience your writing and read it?  


Deidre Woollard

Substack, uh, the money library is where I hang out. So it's mostly writing on books I've read, sometimes a podcast or two.  


Judy Murdoch

I highly, highly recommend it. 


As I said, you make the topic, which for me, I often find rather dry and dull very lively and engaging for me.  


Deidre Woollard

Oh, thank you. I enjoy your work too.  


Judy Murdoch

Thank you so much, Deirdre. Anything else that you wanna talk about that we have not touched on? 


Deidre Woollard

No, this was fantastic. I really appreciate the time.  


Judy Murdoch

Good. Thank you so much.  


Deidre Woollard

Alright, thank you.