May 8, 2025

Episode 356 - Abby Davisson: How to Make Decisions About Money and Love

May 8, 2025

Abby Davisson is an award-winning Fortune 200 leader-turned-entrepreneur; author and speaker; and expert on holistic decision-making (the type that takes multiple bottom lines into account). The book she co-authored, MONEY AND LOVE: AN INTELLIGENT ROADMAP FOR LIFE’S BIGGEST DECISIONS, was named a top business book and is required reading at Stanford’s Graduate School of Business. After spending more than two decades making change from within organizations, she launched her own, focused on helping ambitious leaders make smart choices for lasting success and wellbeing.

She shares actionable tips in her newsletter, Practically Deliberate. Abby’s professional experience includes 9 years at Gap Inc., where she served as president of the Gap Foundation and co-founded the company’s employee resource group for parents. She holds a BA from Yale University and an MBA and MA in Education from Stanford University. She lives with her husband and two sons in San Francisco, California.

How do we make the most important decisions in life with intention rather than impulse? In this episode, we are joined by Abby Davisson to unpack her practical framework for better decision-making. Abby is a Yale and Stanford alumnus, a former executive at Gap Inc., and the co-author of Money and Love. She is also the founder of the Money and Love Institute, which is dedicated to helping individuals and professionals navigate life’s most significant decisions. In today’s conversation, Abby unpacks her practical, research-backed “5Cs Framework” for decision-making and demonstrates how it can guide all the decisions couples need to make through life. We explore the idea of financial transparency, progressive pooling of finances, equitable division of housework, deciding when to outsource help, and navigating career pauses or transitions. Abby also shares how she applied the framework in her own life and offers an honest perspective for individuals navigating change. Join us to learn how to approach choices and the “life stuff” that doesn’t always show up in spreadsheets with Abby Davisson. Tune in now!

Key Points From This Episode:

(0:04:16) Myra Strober’s Work and Family course and how it led to writing Money and Love.

(0:07:21) The drivers of poor decisions and the five Cs in Abby’s decision-making framework.

(0:11:15) Discover the four big topics every couple should discuss and how to approach them.

(0:15:09) Learn the fundamentals of how couples should handle and combine money.

(0:17:49) Why division of housework is vital, how to approach it, and the role of gender norms.

(0:21:49) Outsourcing tasks and the impacts of not taking the division of housework seriously.

(0:24:27) How to decide where to live as a couple, and whether to rent or buy a house.

(0:29:08) A real-life example of how to apply to 5C Framework for decision-making.

(0:33:34) Navigating career ambitions, division of childcare, and stay-at-home parenting.

(0:37:16) Hear how the 5C Framework helps deal with separation and family dynamics.

(0:40:31) Ways the concept of retirement has changed and why families should discuss it.

(0:44:12) Find out how involved adult children should be in their parents' retirement planning.

(0:47:02) Advice for finding the right life partner and how to stress-test a relationship.

(0:52:05) What to consider before getting married and having children, and why.

(0:55:37) Abby’s biggest lessons from writing the book and her definition of success.

Read The Transcript:

Ben Felix: This is the Rational Reminder Podcast, a weekly reality check on sensible investing and financial decision-making from two Canadians. We're hosted by me, Benjamin Felix, Chief Investment Officer at PWL Capital, and Cameron Passmore, CEO at PWL Capital.

Cameron Passmore: Welcome to episode 356. We’re a little rough in the voice this week. Ben, I'm getting over the flu, and I think the first time since you and I known each other, I actually got a rough voice. It's brutal today. So, I sound a little bit different, I guess.

Ben Felix: First guest episode you and I have recorded together in quite a while. Nice to have you back though.

Cameron Passmore: Yes, the last one I did was a solo.

Ben Felix: After I had my surgery.

Cameron Passmore: Your surgery when I was solo, yes. Anyways, this is a great conversation. You got us to meet Abby Davisson. It was an award-winning author, speaker, and coach, specializing in "deliberate living and holistic decision-making." So, it's really decision-making around money and love, which is a topic of her book that came out, I think a couple of years ago now, that she co-authored with Myra Strober called Money and Love: An Intelligent Roadmap for Life's Biggest Decisions. We just cranked through the questions that she came up with her and she was fantastic.

Ben Felix: So, Abby's the founder of the Money and Love Institute. Prior to that, she spent nearly a decade as the president of the Gap Foundation. Gap is the clothing company. She co-founded Gap's Employee Resource Group for Working Parents. Prior to that, she had strategy-focused roles in the public, private, and not-for-profit sectors, and experience serving as an alumni career advisor and coach at Stanford Graduate School of Business. She studied at Yale before that. Her MBA is from Stanford, which is where she met the book's co-author, Myra Strober.

Myra is not on the podcast with us, but she did co-author this book with Abby. The two of them together, I mean, I guess that was their idea when they wrote it, bring a really interesting combination of perspectives. Because Abby has lived through all of these decisions they talk about in the book, and Myra has studied them as a labour economist. Their joint perspective on all this stuff being like the practical perspective from someone who's very recently lived all of these decisions, and Myra, who's studied them for a career, and is still living some of them, as Abby talks about at the end of the episode.

Myra's research and consulting focus on the economics of work, and family, and gender issues at the workplace. She's got her PhD in economics from MIT. The book is like, here's a framework for making good decisions. Here's how they apply to a bunch of decisions that couples have to make. That's what the title means. I like frameworks. I like that. Each section has the right combination of practical information, like here are the questions that you should think about, the specific things that you should talk about with your partner before making this decision. But then, it also has a nice dose of, here's what the evidence says about how people respond to this outcome, or how happy people tend to be when they make this decision. So, I found that to be a nice way to frame some really important decisions that every couple has to make throughout their lives. That's what we talked about with Abby.

Cameron Passmore: Beauty.

Ben Felix: I did want to say, somewhere in the episode, I mentioned the trusted contact person in Canada, but I was unsure of whether financial firms are required to have trusted contact persons for their clients or if it's recommended. So, I had to look that up. We are required to ask every client if they would like to assign a trusted contact person, but the client is not required. They're encouraged to assign one. We're required to ask, but it's not a required thing to be assigned. Anyway, it's relevant to one of the questions we discussed. You'll hear that in the episode.

Cameron Passmore: Viable amendment you made. So, that's great. Okay, with that, we'll go to our conversation.

Ben Felix: Yes, let's go to episode 356 with Abby Davisson.

[INTERVIEW]

Ben Felix: Abby Davisson, welcome to the Rational Reminder Podcast.

Abby Davisson: Thanks so much for having me.

Ben Felix: Excited to be talking to you. Loved your book.

Abby Davisson: I am so honoured.

Ben Felix: I read a lot of books. I think this is a really useful way to frame a bunch of important decisions. Can you tell us the backstory of the work and family course at Stanford, and how that ultimately led to this book.

Abby Davisson: I co-wrote the book with Professor Myra Strober. She's a labour economist and was actually the first female professor to get tenure at Stanford Business School. She went to the school in 1972 to start teaching there. And she, as one of the only women getting a PhD at MIT before that in economics and navigating different universities, had faced a fair amount of, let's say, work and family challenges in her own life.

The previous university where she taught offered her a lecturer track role instead of a tenure track position, which they had offered to her male colleagues who graduated from the same program that she did. When she went to ask why, they said, "It's because you live in Palo Alto." and she scratched her head. They were in Berkeley, and she said, "I don't really get that." Well, it turned out they were really saying, "You have two young kids. We don't really know what's going to happen to you." She decided to teach a course based on her own experience, and it was called at first, Women and Work. It was an interdisciplinary course because there was no such thing as feminist economics. She was a pioneer in that field.

Eventually, when she switched over to teach at Stanford, she started teaching to anyone who would come. One day, one of the years, an intrepid man took the course, and he said, "You would attract a broader range of students if you called it something more inclusive. I'm a man and I find these topics really important for me." So, she changed the name to work and family. That is what it was called when I took the course in 2008. I took it with my then-boyfriend at the time. We were both second-year MBA students trying to decide if we would live together after we graduated, and how we would navigate that. We ended up writing our final paper on all of the life decisions that we would need to make together and how we would do that with all the information that was shared in the course.

We graduated, fast forward, we had several kids, we navigated career changes, we dealt with our aging parents. When my co-author retired in 2018, she said, "I really want to write a book about the course." And I said, "You should, it has helped us so much." Ross and I, my husband and I, had been guest speakers in her class for many years. Then, when we had lunch about a year later and I asked her how the book was going, she told me she hadn't written a word. So, I said, "Oh, well, maybe you need an accountability partner." Because at the time, I was an executive at Gap Inc. I had helped to start the first Employee Resource Group for Working Parents at the company, and I did that with a working dad on the legal team. I knew how important a partner was for a big project.

She looked at me and said, "Actually, I need more than that. I need a co-author, and you have been navigating all of these lessons and the trenches for the past decade. Would you write this book with me?" I immediately said, "Yes." Jumped at the chance, thereby violating every rule in our book, which is, don't make big life decisions in an instant, but we had known each other for over a decade. She was a mentor of mine, and I knew it would be a fruitful collaboration, and it really has.

Ben Felix: Very cool.

Cameron Passmore: It's an amazing story. Can you talk about the challenges with making holistic decisions that optimized for the long run?

Abby Davisson: We have a lot of human biases that have kept us alive evolutionarily. So, one of those biases is that we're very wired for the short term, and we're very wired to see all of the negative consequences of our decisions. When we're often making decisions, we are in a state of stress. Our emotions are high, we might have anger, or fear, or guilt, or some other emotion that is preventing us from really accessing System 2 thinking, that Daniel Kahneman talks about. Our System 1 is emotional, very quick for us to access, it's frankly what we use to navigate all the decisions that we make that we don't even realize we're making every day. But when it comes to bigger decisions, decisions where money and love are on the line, which is most of the big ones that we make in life in terms of, do I marry this person? Do we want kids? Where should we live? Is this still the right person for me? Many years into a marriage. Divorce, elder care, et etcetera.

We need to find a way to trick our brains to overcome those human biases and move from System 1 to System 2 thinking. The challenge is getting yourself out of that emotional state into a more rational, logical, deliberate state. That is really tricky for us humans. This is one of the reasons we developed a framework in our book for how to think through big life decisions. Because the conventional wisdom is that you should really separate decisions about money, financial decisions, career decisions, from decisions about love. We've all heard that adage, "Don't mix money and love." Really separate those two, make romantic decisions with your heart.

Well, the truth is that every big life decision has a component of money and a component of love in it. So, by separating them, you are doing yourself a disservice and are more likely to make a decision that you regret.

Ben Felix: Let's go there. Can you talk about the five Cs in your decision-making framework?

Abby Davisson: As you mentioned, we call ours the 5Cs, and it starts with clarifying what's important to you. That's really about knowing your core values, tuning out all of the other voices you might hear, trying to influence you to tell you what you want, society, your parents, et cetera. It's really getting the inside view in Daniel Kahneman's terms. Then, you move to communicate the second C with those most affected by the decision, and clarify, and communicate go together because you clarify what's important to you. You communicate, say with your partner, you hear what's important to them. It might cause you to change your mind.

So, then you move to the third C, which is to consider a broad range of choices. Now, you're starting to get the outside view, and part of making a better decision is expanding your consideration set. You're trying to get away from the binary thinking that many of us get into when we're in these places of high stress. Do I quit my job or go for the promotion? Do we renovate our house, or do we move to find a bigger one? But there's many places in between that might actually be better solutions.

One of the ways you could access those creative choices is by the fourth C, which is to check in with trusted resources. These might be people who have faced the decision before. These might be even published studies that can give you insight. Start to get the outside view and to introduce more creative choices than you might see for yourself. Then, the final C, the fifth C is to explore likely consequences on broad time horizons. So, not just the short term that we're all wired for, but also medium and long term. Not only the negative consequences, which, again, as we humans tend toward the negative, we see more clearly, but also some of the positive consequences. This is a forecasting exercise.

The five Cs are iterative. I just went through them linearly, but you might learn something as part of one step that causes you to re-clarify, and then, you will go through the process again. That is the tool in a nutshell.

Cameron Passmore: What are some of the big conversations that couples should have early on?

Abby Davisson: I am definitely aware of all the conversations I didn't have in previous relationships before I started dating my current husband, and was forced by nature of the class to have those big conversations. Because sometimes when we like someone, and we think it's going well, we don't want to rock the boat. We don't want to introduce a weighty topic that we think might scare someone off, or we might find out that we're not on the same page. But the truth is, if you're going to find that out eventually, better find it out early on so that you can either decide that you can agree to disagree or that you realize, "Oh, wow, this isn't going to work out because we have some pretty fundamental disagreements.”

The four topics I say are really important are, number one, money. That is a topic that it is so taboo to talk about still, although it's getting less taboo certainly than in my parents' generation for sure. But spending and saving habits, do you have debt? What is your approach to investing? These are just philosophical questions that we have different points of view on. Also, we have money stories based on how we were raised, based on what we saw our parents do, and not do, that are informing our money.

The second topic is – and these are all interrelated, so you'll see as I go through them. The second is career aspirations. You might meet someone when you're in one profession, but you might know that down the road, you want to do something else. To make sure that you're sharing those career aspirations, particularly when it comes to the third topic, which is children. Do you want them? How many? When? What are you willing to do if you cannot conceive naturally? These are important topics to just get someone's view on.

Then, the fourth is home, and it can go in different directions. Where do you live? Where do you want to live? How would you decide when to move? What does home mean to you? Does that mean somewhere close to your family? You might meet someone when you're not living close to your family, but eventually, you want to move back to your hometown. All the way to how you imagine sharing household chores. I just did an event with a divorce attorney, and she was saying that so many of these topics are the ones that ultimately lead to divorce when people realize they're not on the same page. So, getting those topics and your feelings about them out early on is so critical because then, you start to build the muscle of being able to have uncomfortable conversations.

I liken it to weightlifting. The first time you lift a weight, it's uncomfortable, and you might be sore the next day. It's not a fun experience necessarily, but if you keep up and you continue to do the reps, you adjust, you build the muscle, and you find yourself stronger as a result.

Ben Felix: You mentioned that you and your now husband went through those questions, because you were in that class together. How would you suggest that typical couple who were just dating, how do they broach those topics?

Abby Davisson: Every chapter of our book, which is organized by each of the life decisions we tend to encounter, and roughly the order that people encounter them, has exercises. So, I like to say, blame the book. You might not be able to take the class, but you can certainly say, "Oh, I heard this author on Rational Reminder, and there are these questions I realize we've never talked about them."

But as a couple who's just starting out, I think the money question is really well approached in the context of something that makes sense. Before you go on a trip together, that's a perfect time to say, "We haven't talked about our budget for this trip." One thing I want to share is that I'm still paying off some educational loans. So, that means that my budget for our accommodations is X, and I'm hoping we can stay within that. But it made me realize, we haven't really talked about money. How do you think about your budget? It's a weight, and it feels more natural, and it's not so forced, and it starts to bring it up in small ways that then build up to some of those bigger topics.

You don't need to pull out your credit report on a first date or start to show somebody your paycheck, but you can introduce it in lower-risk ways and start to model revealing things that you might not reveal otherwise.

Ben Felix: Can you do a deeper dive on how important it is to discuss how you're going to handle finances as a couple?

Abby Davisson: There is research that says that couples who talk about money weekly, 78% of those couples say that they're happy, compared to 50% of couples who say they never discuss finances. So, it's actually a recipe for happiness, and it's because it's about getting on the same page, and building that trust, and the transparency. It's really crucial.

One of the things that we did as part of the course was talk about how to combine our finances. My husband was going to accept a job in finance at a hedge fund. I was going to work in the nonprofit space. We were making radically different salaries after business school. One of the questions we broached was, how should we contribute towards our rent? Is it fair for us to pay the same amount, split it down the middle, or should we contribute a percentage of our salary? How do we want to pool our finances? Should we pool everything, pool only a little, partial pooling, or do we want to manage that independently, and just send each other Venmo requests for things like rent? Well, I think Venmo didn't exist at the time, but you get the idea.

We looked at actually a variety of couples and how they managed their different finances. The arrangement that we decided to go with, which actually is what the researcher says is the best practice, is to pool some of our funds, but not everything. What we did was, when we moved in together, we set up a joint account that we contributed to based on a percentage of our salary. We then upped the percentage when we got engaged, and then upped the percentage of our contribution again when we got married. So, as we built trust, as we deepened our relationship, we had more at stake as a unit, and yet, we maintained our separate independent accounts to be able to do things like buy each other gifts, take vacations that the other one didn't go on, and have some financial independence. So, the phrase that Scott Rick uses, who I know has been a guest on this podcast, is “financial translucency.” I think that is the approach that the research says really leads to the best outcomes.

Ben Felix: That's really interesting. It's like a progressive pooling of finances as you build trust over time.

Abby Davisson: Exactly. I remember, we were reminiscing about when we first set up our joint account, and we've now been married 15 years, together for 18. We said, if we spend more than $100, we need to check with the other person. Now, you go grocery shopping, and that's immediately $100 right there. The times have changed, and our trust has deepened. So, our flag amount for when we have to check in with the other person has increased as well.

Cameron Passmore: I'm curious, how important is the division of housework in a relationship?

Abby Davisson: It is so important. It's one of these things where it's very easy to fall into a habit or a pattern that is not a conscious choice, but it's, "Okay. Well, you work from home, so it's easier for you to meet or pair people when they come in during the day." So suddenly, the person who works from home has all of these responsibilities that they didn't sign up for, but by nature of them being there, it's somewhat more convenient. So, it's very easy to slide into these types of decisions rather than decide. Then, that ends up in a very inequitable distribution of tasks.

One of the tools that I recommend, that I think is very powerful, is the set of cards from Eve Rodsky, it's called Fair Play. These are a set of 100 tasks that are required to manage a household and children, if that's part of the household. The goal is to look through the 100 cards; they're both one-time tasks, annual tasks, like doing taxes, all the way to daily tasks, packing lunches for the kids. You look through these 100 cards, you discard the ones that are not relevant for you, or you decide that you don't want to take on as a family.

If you don't care about thank you notes, great, discard the thank you note card; nobody needs to own that. But then, with the remaining cards, you have a conversation about how you want to divide those cards in a way that just makes transparent and visible all of the different tasks involved, and you are able to divide it in an equitable way. If your partner is not yet up for this game, you can start with a smaller set of discussions, but the key is to choose guilt over resentment.

You might say, "Oh, I feel guilty asking my partner to do all these things. They're working a lot. They're travelling." That might be uncomfortable for you to feel guilt, but choosing resentment where you don't say anything, and you just build up a frustration over time, is actually toxic for relationships.

Ben Felix: How influential are gender norms and how people tend to assign housework?

Abby Davisson: They're very powerful. And certainly, what you saw modelled in your own family starts to shape your own mental models of how housework should be divided, as well as what society expects. So, I'll give you an example. In our family, we decided that my husband would own the card for medical and dental work for our kids. This started when we had our first son, who's now 12, after the initial newborn appointments. He would be the one to take him to his pediatrician visits. And yet, the doctors would always call me to remind me and to me, "Make sure you're going to bring in your son on this date." And I would say, "Oh, that's great. Could you actually call my husband? He's the other name listed on the contact form and the one who's going to be there with him."

You have to sort of train society that you're going to be doing things differently sometimes. But again, the important thing is to make a deliberate choice that works for your family as opposed to defaulting to what is expected or what you saw modelled.

Cameron Passmore: Do you have thoughts on the best approach for couples to actually take and dividing up housework?

Abby Davisson: I think the Fair Play cards are great. The idea of re-examining on a periodic basis is also important because things change, and circumstances change. There was a period of time, for example, when I was writing the book and working full-time in my corporate job, and my husband and I had a deliberate conversation before I took on the task of writing the book. I said, "Look, for this next year, when I'm deep in research and manuscript writing, I'm not going to be able to do as many things related to the kids and running the household. That means I will need you to pick up some of that slack. Are you comfortable with that? Is that okay with you?"

So, pre-checking in when you know a big change is coming and when you know there's going to be a season that's going to be bonkers for you. Then, kind of addressing that proactively as opposed to letting that resentment build up, is also a best practice.

Cameron Passmore: When does it make sense to outsource house stuff?

Abby Davisson: I'm a huge fan of outsourcing, and we definitely outsource a lot. I think a lot of people look at their salaries, particularly when it comes to outsourcing for childcare. And they say, "Oh." In a different sex couple, a heterosexual couple, I often hear women say, "My salary was not even going to cover the child care, so we just decided I would stay home for the first few years." Well, I hate that math because really, it's not just coming out of one person's salary. The child care comes out of both people's salaries in a marriage, and there's an opportunity cost for being out of the workforce, and it might be very challenging to get back in.

I think you need to think about certain outsourcing tasks as investments, particularly childcare, that's an investment in your future career. You're not always going to pay such a steep rate for, particularly newborn care, that does decrease over time. So, sometimes, it makes sense to outsource because of an investment perspective.

But there also might be decisions where it's a domino effect. If you decide, for example, my parent moved into a senior community where they actually don't have to manage the lawn care, all the things that you do in a single-family home. That was partly because even managing the outsourcing of it was getting to be a challenge. So, when you decide outsourcing is something that we need because of our busy lives, think about one bigger decision you could make that would actually eliminate a lot of that outsourcing, as opposed to continuing to outsource everything.

Cameron Passmore: What are the consequences of getting the division of housework wrong?

Abby Davisson: First of all, I would say, you can course correct. So sometimes, I get the reaction of people who say, "Never had any of these conversations. It's too late for us." I would say, "It's not too late." But I think the key is, the consequences can be pretty significant. I mean, a divorce as one of the very significant ones. But then, also, just a real degrading of a relationship. There are studies that show that couples who contribute equally to the household income and to the household responsibilities have lower divorce rates than households where those contributions are less equitable.

If you look at the research, it makes rational sense to be talking about the contributions regularly, because as people change jobs, as kids' ages change, as there or other things that shift, it's something that you want to regularly revisit. And not just assume, because we had this conversation once, and we made one set of decisions that is going to endure for the rest of your time with someone.

Ben Felix: What are the main decision points people should think about when they're deciding physically where to live?

Abby Davisson: Certainly, the framework can be helpful, but I think it's helpful to think about things such as family help. So, this is something that there's been a lot of research around the early child years of any parent's life are tough. There's just a lot of demands, particularly if you're continuing to have a full-time career while you're bringing up children. And the difference between people feeling, "Yes, this is intense, but I can handle it,” and this is really breaking me, is how much help that they have, including, especially, from family. I think that's something that's been a trend where we're seeing people, whereas the trend, the norm was to move wherever the opportunities were for your career.

Now, I think there's a trend that we're seeing of people thinking through, actually, if we both want to continue to work in a lot of major cities, you need two incomes to really make it work. We need to be closer to family. So, that's something to think through.

Also, if there are other factors, whether it's for health perspectives, hobbies you really enjoy. There's really interesting research that different parts of, certainly the U.S., and I imagine this is true for Canada, attract different personality types. Richard Florida has done really interesting research in this area. You might think about the places in the country that are best suited for not just your career prospects, but also personalities, and the activities. Then, when it comes to a preference for a city versus a suburb, it's really thinking through what are the criteria that are important to you. We have an exercise in the book to help with this, assigning prioritization to those criteria just as you would as you're thinking through any nuanced decision.

Then, following the framework, having conversations with people who live there, trying to do some check-ins. And ultimately, not just looking at the financial, is this a good investment for us to buy here or to continue to rent here? But how is it going to make me happy or how is it going to contribute to my well-being on other dimensions? Which I think some of us often skip when it comes to those types of decisions.

Ben Felix: I love that.

Cameron Passmore: How would you suggest that people think about the rent versus own decision?

Abby Davisson: There are so many different calculators that you can find online right now. One of the things that I think is not discussed enough is your preferences for having autonomy. So, this idea of not being able to make much changes. Is it really great for you to outsource everything to a landlord? And that, again, is one of those decisions where you don't have to make a lot of sub-decisions under that because you have someone else managing it. Or are you going to be somebody who's frustrated when you really want to change the way a certain part of the home looks and you can't because it's not yours? So, thinking through some of the personality-related aspects can be helpful.

One of the things they sometimes get asked is, "Well, what do you think about home renovations?" There is a trend towards saying, "Okay, well, you can buy a house and then just evolve it over time." One of the things that I think is interesting is, again, personality-wise. Some of us tend to be more maximizers when it comes to decisions, meaning we're trying to really get the right answer, the best version of whatever it is, whether that's a pair of black pants, whether that's the perfect fixtures for a bathroom, and some of us are more satisficers. We're fine with whatever pair of pants as long as they fit, and are black, or if a bathroom works, and it lets me do what I need to do there, I'm good with it.

We saw this firsthand. My husband and I tend towards the maximizer type. So, we remodelled one bathroom and it nearly killed us, because we felt like all the different decisions that we had to make, it was like a second job after we performed our first job during the day. We had a ton of choices to make at night. Whereas, my sister-in-law remodelled an entire house as she was working full-time, expecting her second child, and she is much more of a satisficer. So, she just made the decisions and moved on. That's one of those areas where you don't necessarily think about that before you undertake a remodel, but it can really significantly impact your well-being.

Ben Felix: Oh, yeah. We did a kitchen years ago, and it was so stressful. Then, recently, we haven't started yet, but we're going to do another small renovation project in our house. I found somebody whose work I really like, and I was just like, "Listen, this is the general idea of what we want to do. I don't want you to ask me for any input. Just do it. I like what you do. Just please don't ask me anything and just do it." So, we'll see how that goes.

Cameron Passmore: Classic Ben.

Abby Davisson: I think it sounds like you made the decision to trust the expert that you hired, and you were going to be okay with whatever they did.

Ben Felix: Yes, exactly. Coming back to the 5Cs framework, can we use housing as an example? And can you take us through like how a couple would use the 5Cs to make that housing decision?

Abby Davisson: I can actually share a personal example, because I used it myself. Both my co-author and I actually used the five C framework to make decisions about whether to stay or move with different outcomes. So, she used it and decided to move twice, actually, since we've written the book. I could share my experience, which is, pre-COVID, we were in a small footprint home in the center of San Francisco. My husband and I commuted downtown. We had our two young kids in nearby schools. We had outsourced a lot of the childcare that we were just talking about.

When everything shut down in the pandemic, we found ourselves working remotely from rooms that were not intended to be home offices. Our kids were Zooming in to remote school from our dining room table. They were four and seven at the time. Eventually, we had a couple of college students who would come in and help them stay on Zoom tasks while we attempted to do our jobs, and we were all on top of each other all the time, and we thought, we just need more space. When we started to clarify, we said, we need more space, we need schools that are open.

So then, we would communicate with each other. I would say this conversation had been simmering, the city versus suburbs conversation for a while, and COVID really turned it up to a boil. What we learned is that where and when you communicate is just as important, in fact, more important than what you say in that communication. For example, we would bring this up as we were brushing our teeth, getting ready for bed at night. Not a great time to have conversations about major life decisions.

We started having these conversations on hikes. That was one of the activities that was available to us at the time. It turns out that when we got away from the stress of being locked down in our house, away from the dirty dishes and the chores that needed to be done, out into the hiking trails, we could think more expansively. Our kids would run ahead, and it was a better conversation.

Then, we considered the choices, decided on a specific suburb that was close to my dad, and we had some friends there. And we started checking in with realtors, with people who had left the city and moved to that particular suburb. But we also checked in with a published study. And interestingly enough, I was writing the chapter on moving as we were going through this process. I came across this study in the Journal of Environmental Psychology about the impact of density on well-being and family happiness. So, square footage per person, essentially.

You would think that the more space you have, the better. Well, it turns out, there's a point of diminishing returns. Actually, once the home gets too big, like if there's a separate wing for the kids, children, particularly boys, which is what we have, can feel disconnected and lonely. So, that was interesting. Then, it also turns out that a family's perception of a space is a far bigger indicator of family harmony than the actual physical square space.

As we were complaining about, "Oh, this place is too small and we're all on top of each other," we were not doing ourselves any favours when it came to our family functioning. We started to move to the consequences, and had some houses we were interested in. We're about to put in some offers, and we did the math. Based on the fact that everyone needed more space at the time, home prices were quite inflated. Also, we realized that taking on a bigger mortgage, which we would be doing, would be tethering us more tightly to our corporate salaries.

When we had that realization, we re-clarified and said, "Hold on. Do we really value more space and open schools, or do we value career flexibility?" We want to actually take advantage of the fact that we had been in our current home for quite a while. We had home equity built up, and that would provide a bit of a financial cushion. It turned out that we both decided we wanted career flexibility more than more space.

Once we made that decision to stay, it turned out we were able to think more creatively about how to get more space and schools that were open. So, I decided to rent an office, is where I'm speaking to you from an office that's a seven-minute walk from my home, and we ended up switching our kids' schools to an independent school that had more flexibility and was able to be open. That's where they both go today. This idea of, once you cut off one avenue, which you think is the only way to get what you want, you could have more creative choices that help you have your cake and eat it too. Now, fast forward to today, my husband and I both started our own businesses, and so we did get the career flexibility and went down the entrepreneurial path.

Cameron Passmore: Wow. Great story. How should couples think through the division of work and child care?

Abby Davisson: So, this is also one of those conversations that is so much easier to have when it's a theoretical conversation. Before, there's an actual baby that needs to be cared for. So, making it clear whether continuing to work full time is important to you. I, for example, had always thought my mom had paused her career when she had me and my brother, and then it actually went to work in a part-time capacity. And I thought, "Oh, part-time work seems like the way to have both." It turns out that in my co-author's class, I learned about all of the ways that part-time work is actually a great deal for the employer, and not such a great deal from the employee perspective in terms of, you often work more hours than you're being compensated for. You don't have as much access to benefits, et cetera.

I had resolved in that class that I was going to find a way to continue to work full-time. I had told that to my husband when we were first dating and said, "This is important to me. I want kids, but I also don't want to have to compromise my career in order to do that." He agreed that that was something he was open to. So, getting those conversations out early on to make sure that nobody has assumptions about, "Do you want kids, first of all? Do you want to continue in your career? What does that mean in terms of our budget needs then?" Because child care is quite expensive, particularly in the U.S. Then, talking about if you assume that your parents are going to help you care for your child, have you actually talked to them about it?

I think, sometimes, people make assumptions of, my mom is going to love caring for her grandchildren. Check in with her about it, because that might be like, I'd love to come visit and hang out with them for a couple of hours on a weekend, as opposed to, I would like to be your nanny. So, those are, again, important conversations to navigate ahead of time.

Ben Felix: My parents did that for my sister who has a young child. They're just now ending their nanny duty. I think they're super excited to do it, but I know now that it's come to an end, they're kind of like, "Oh, that was intense.”

Abby Davisson: Happy to go back to seeing them less regularly.

Ben Felix: Yes, exactly. You mentioned this earlier. How common is it for someone who decides to be a stay-at-home parent to successfully return to a career later?

Abby Davisson: The data is mixed on it. Definitely, a lot of factors help to ease those ramps back into the workplace. So, the ability of someone to keep their skills and their network warm during the time that they're away is really critical. If they have a license, say, they're a professional that has gone through a licensing program, continue to keep that license active, so there's not a re-licensing effort that needs to happen, is also important.

One of the things that if you do decide to take a career pause is to go into that intentionally, and say, "I'm making this decision for this period of time, but I know this is not forever." I think the challenges that we see are when people, again, slide into the arrangement as a gradual thing, or maybe they got laid off right before. The thing that we're actually seeing, unfortunately a trend towards, with all the layoffs that are happening, people getting laid off on parental leave. They are realizing, "Okay. Well, I thought I would have a job, but I don't. I'm not working right now. Maybe I'll stay home with this child." Then, not having put those steps proactively in place to think about how am I going to keep my skills and network sharp. Then, it is much more challenging to get back into the workplace afterwards. All of these decisions, the key is don't slide, decide.

Cameron Passmore: How would the five C framework apply to deciding whether to end a marriage?

Abby Davisson: I was just at an event speaking with a fellow panellist who is a divorce attorney, and the second C of communication is really the key. So, if you have tried to have a lot of conversations with your partner, there have been issues. You have tried couples therapy, you've tried to rely on trusted experts, and you're really not able to move past some of these insurmountable challenges. The key to clarify is how to separate while still maintaining a collegial relationship, because I think the hardest parts, particularly when there are children involved, is when the conflict becomes so large and toxic that it really has a negative effect on the entire unit.

So, my co-author went through a divorce with her first husband, and she talked about how it was very helpful when she clarified the 5Cs didn't exist at the time, but we developed it together as part of our research. But she said, the biggest help for her was to clarify that what was important to her was to maintain a positive relationship with her ex-husband, so that the kids would not have negative outcomes from that divorce. She eventually remarried, and her new husband and ex-husband actually knew each other. Her new husband, her second husband proposed, what do you think about having her ex, and he had remarried at that point, over for Thanksgiving, so our kids wouldn't have to go to two houses, to two different Thanksgiving experiences. She said, "That's interesting. Ask me again in five years." Five years later, he asked her, and she said, "Okay, at this point, I'm open to it."

Now, he's since passed away, but for many years, they hosted a joint Thanksgiving experience, and so, their children were able to have that, and still have all families involved. That point of clarifying what was important to you. Once you do that, it makes all the other seas move more smoothly because it is your North Star that you're using as a guide to solve for the situation. So, that's an example of how having clarity about what's the priority in that experience. It's not to say divorce is an incredibly hard and painful, but then, it can have a positive outcome for children when you have that type of clarity.

Cameron Passmore: That sounds like a really smart solution. How does divorce affect children more generally?

Abby Davisson: Studies show that what really is the lynch pin is the amount of conflict in the divorce. So, when you're able to work through the issues and set up an arrangement where the kids are having as much stability as possible, that does not have a negative effect on the children. We've seen creative solutions, such as parents often – one person is moving out of the home to a new home. We've seen creative solutions where the existing family home becomes the place where different parents move into. So, the kids continue to stay in the home. Each parent has a separate place that they're then moving into during the weeks that they're not parenting the kids. Obviously, that takes a lot of resources, so it's not an option for everyone.

Again, when you think about the choices, there are choices that help get you closer to having what is needed for children to maintain their stability after a family rift like a divorce.

Cameron Passmore: How has the concept of retirement changed over time?

Abby Davisson: It's changed a lot, and it's still changing, as longevity has gotten longer and longer. The demographers estimate that the average baby born today in an industrialized nation has a 50% chance, likelihood, of living to 100. When you think about that, you think about that our traditional retirement age is 65. The math doesn't math to just be educated for the first third of your life, work for a third of your life, and then be retired. So, you will end up having to pay for a very long retirement with that type of arrangement.

This idea of having periods of time where you're dialling up and dialling down the amount of autonomy that you have in your life, as opposed to just flipping a light switch off of your career at a certain age, is becoming more of the norm. So, you've seen perhaps this idea of many retirements in the news, where millennials or even younger people are saying, "I'm not going to delay retirement to 65. I'm actually going to take a couple of years and do some things that I might not be able to do when I'm older, from a physical perspective. I'm going to plan for that eventually, and I'm going to treat retirement not as one thing that I do at the very end of my life, but that's something I intersperse into my life because I want to work longer. I'm going to have to work longer to finance it, but I don't want it to be just a sprint that I'm working until one day I then suddenly have the entire day available to go be 'retired.'"

Ben Felix: In light of the changing nature of retirement, how important is it for adult children to discuss their parents' retirement plans with them?

Abby Davisson: I think it's really important, and it's certainly important for you to discuss not just retirement plans, but plans for how they want to be cared for when they can no longer care for themselves. Lots of things that are really uncomfortable. We don't like to think about endings, we don't like to think about death in our society, but these are really important conversations to have, Again, while it's still theoretical, while it's still, you're not sitting in an emergency room being like, "Has anyone talked to mom about what she wanted in terms of her care?" This is something, unfortunately, that my family had to do because we didn't have any of those conversations.

Then, my mom had a serious accident that left her in the ICU. We realized, we should have had a lot of these conversations earlier. It actually happened on the day – that was supposed to be her last day of job before she retired. So, life is very ironic sometimes.

I like to say, especially if you're working with a financial advisor, or if you're working on something for yourself, your estate plan, for example, it's a great time to approach your parents and to say, "We're starting to think through some of these questions for ourselves around our retirement planning, around how we want to be cared for when we can no longer care for ourselves. I realized we've never had these conversations. Can you help me understand how you approach these topics, the things that you've set in place?" So, that can be a good way into the conversation.

But there's also a lot of data on how dementia and some of these degenerative diseases can be diagnosed up to seven years earlier based on activity in bank accounts, as opposed to a doctor. So, if you start to see things like double credit card payments, missed credit card payments, there's an impact on credit scores. That can be a warning and an indicator that there might be some concerning neurological issues before, again, it gets to a point where they're giving an official diagnosis by the doctor. So, these are really helpful conversations to have because they can raise issues that you might not know about for many years.

Cameron Passmore: How involved should the adult children be in their parents' retirement financial planning?

Abby Davisson: It really depends on a lot of factors. An important conversation to have is how the parents want to care for themselves when they can no longer support themselves and care for themselves, whether they can pay for that, and how, if they anticipate needing any financial support. Depending on your family's situation, your parents might say, "Yes, we've thought about that. We want to stay in our home as long as possible, and we've set aside money funds in order to do that." Great. Other families might be in a very different situation, in which case, the children will have to be very involved not only in their financial planning but in actually providing support.

So, you're the sandwich generation, where you're paying for childcare as well as contributing to your parents being able to have care for themselves, is very real. As we are in this silver tsunami of more people turning 65 every day than ever, we're certainly going to begin to see more situations where people are supporting both their children and their parents. I think it's very critical to have the conversation to understand what you're working with so that you can start to take steps to understand how involved you'll need to be.

Ben Felix: Yes, it makes a lot of sense. Rather than it being a surprise when you're like, the adult channel doesn't have it factored into their own financial plan, and all of a sudden, they have to provide support unexpectedly. That could be very stressful.

Abby Davisson: It's one of these things where the conversation is so uncomfortable and I've had it myself in less-than-ideal circumstances. It is so much better to have it proactively when it's just a hypothetical than when it is a necessary situation.

Ben Felix: The point about cognitive decline is really interesting too. Here in Canada, we, by our regulatory body, are required, I think, encourage or required, I should know definitively. But anyway, something that we assign to client accounts is something called a trusted contact person, a TCP. And it's basically, if we see signs of cognitive decline, and it's a person who we can contact. So, the client gives us permission ahead of time to contact this person just to say, "Hey, this person who you're the trusted contact person for is exhibiting these behaviours. We just want to let you know."

So, we've definitely seen cases where in the client's financial accounts, we'll see something that just doesn't quite look right, and then, we'll speak to an adult child or another relative that they trust. In a lot of cases, it has come back where it's like, they have been struggling. So, thanks for letting us know. It makes a lot of sense.

Abby Davisson: Yes, I think it's not talked about enough, especially with so many ways that seniors are unfortunately susceptible to fraud as well, to phishing attempts, all the ways that our devices let people in when they shouldn't. That's certainly something that is another trigger for the concern. So, it's great that that is a requirement potentially. I know there are services that are set in place when it's called Careful, that is able to provide that monitoring as well.

Ben Felix: So, we've talked about all these money and love decisions. How should people apply this kind of thinking to finding the right partner in the first place?

Abby Davisson: A question that I get sometimes is, "Aren't you taking the romance out of it if telling me to apply a framework to my future partner?" I don't think it takes the romance out of it. I mean, I definitely think there's room for romance. But given that the person who you marry or decide to spend your life with is the biggest career decision you make, it's a huge financial decision. It definitely should be a decision that you go into with some planfulness and rational thought. Instead of just letting your heart lead you. I also do not believe that there's only one person out there for anyone.

I think letting go of that impossible standard of finding the one person is really important. There's some really interesting research when it comes to choices. So, thinking about using the framework, clarifying what is important to you. Again, not just the laundry list. My co-author likes to say, "Don't think about your potential partner as if you're ordering a pizza. I want olives, I want pepperoni. You might not find your wish list in one person, but clarify what are those values that you have that are really important to you that someone else shares?" Certainly communicating, having those conversations with a potential partner to see if you're on the same page, instead of waiting to see how the relationship goes before you broach them. That should be an indicator of how well the relationship is going is, are you able to talk about these tough things? Are you able to have these uncomfortable conversations in a way that actually helps you feel more connected as opposed to makes it seem like this is an insurmountable object or we can't have this conversation.

Then, when it comes to choices, there's really interesting research by a professor named Baba Shiv out of Stanford who looked at the effects of sequential choice. So, if you think about dating apps, it's lots of sequential choice. There's endless people who you can swipe and continue to see other options versus a simultaneous choice. He has an arranged marriage. When he was growing up in India, and said, "I'm ready to get married," his parents went out and found three potential partners for him. He met each of those three partners, told his parents which one was his first choice, each of his potential partners told their parents. Fortunately, for him, his first choice was also her first choice. So, they married. It got him thinking about what are the effects of having a simultaneous choice.

It turns out people who choose between simultaneous options have more satisfying experiences. Not just in the dating realm, but when it comes to deciding what to have for lunch. And if you always think there's a next great option around the corner, then you're going to be hungry forever. Thinking about using that research to guide you, checking in with couples who have endured long relationships in a positive way that you admire and ask them, "How did you think about deciding to get together, or what are the things that you attribute your long-standing relationship to?" Having that perspective with people you admire is helpful. Then, exploring the likely consequences.

Dating is a way of forecasting. I'm trying before I buy. I want to stress test this relationship. So, let's go on a trip together. Let's put ourselves in a stressful situation so we can start to see how we might do under pressure when we're not in the honeymoon phase, or when we have to face something that's really challenging. Making sure you're not just together under ideal circumstances all the time, but that you're actually modelling what it might be to be in a challenging situation.

Cameron Passmore: How should people decide when a relationship is serious?

Abby Davisson: That is a subjective term. I think, being able to have these conversations, if you think that this is someone that you're excited about, you want to take the relationship to the next level, then have these conversations with them. I think that, certainly, if it's somebody you want to introduce to your parents or other important people to you, if it's somebody you want to travel with, these are then the indicators that would say, "Okay. Well, try to have a conversation about money and see how that goes.” Try to have a conversation about children. Again, it doesn't have to be sitting down and saying, "Okay. So, how many kids do you want?"

I remember a conversation very early on that my husband and I had where I was raised Jewish and I knew that that was important to me to raise my children Jewish. He was raised with one parent who was Jewish, one parent who was Protestant, and both in neither. So, we had a conversation over dinner. We were just dating. Kids were light years away from either of our minds. I said, "It's important to me to raise my kids Jewish. I always imagined that I would do that." He said, "I'm open to that. My family celebrated Christmas, and Hanukkah, and everything. I felt like I didn't really have a specific religion. So, I like the idea of having kids who have a strong identity. That works for me." I remember being like, "Phew, okay." I think we just checked that item off the list, even though this wasn't something that was imminent for either of us, but we're able to talk about how we might want to handle that in a way when it still felt like we were fantasizing about it.

Cameron Passmore: What about marriage? So, as taking a relationship seriously, how should couples decide to take that next step and actually get married?

Abby Davisson: It is a really big step. There are lots of financial considerations that certainly in a long-term marriage, one more than 10 years, there are real requirements around. It's not a step people should take lightly. The data show that people are waiting longer to get married. It means they have more assets, and often, more debt when they get married.

Having a conversation where you are really transparent with your finances is really crucial if that's something that you're planning to do. My co-author and I really encourage people, even if they're not planning to get a prenuptial agreement, to do the type of revealing that is required in order to get a prenup, because that sparks really helpful conversations, and can breed more trust and intimacy. I think a lot of people have this concern that, if they have these conversations, they're going to lead to conflict. But my co-author's second husband was a psychiatrist, and he had this great term, which is intimacy, is "into me see." Meaning, you're asking someone to look into your deepest, darkest, innermost hopes, concerns, fears. Those are all linked to money. To be able to talk about those things with each other before you walk down the aisle, or as a way to determine if this is somebody you want to walk down the aisle with is a really helpful step.

Ben Felix: Last one on the framework thinking, what about kids? Marriage is a big decision. Kids are probably a bigger decision. How should couples think through that one?

Abby Davisson: There's so many aspects to it, and it's very tied to career, to money, to family, to home, all the other pieces. It's one of these things where there are actual biological realities where you cannot just put off this decision indefinitely. I remember looking at a chart that my doctor showed me, that showed age on one axis and level of complications on another axis. As your age increases, so do, unfortunately a lot of the complications and developmental differences that can happen in pregnancy. So, it was an area that my husband and I were kicking the can down the road on. We had like a rolling two-year plan, and then, got to two years and were like, "Well, we're not ready for kids." You're never going to feel ready for any of these big things, marriage, kids. I remember looking at the house for the first time. We didn't feel ready to buy a house.

The research shows that things that people regret are not the risks that they did take, but often the risks that they didn't take. The research is that happiness dips for parents pretty quickly, and then kind of as a gradual climb back up, but it's really about purpose and meaning. Parents have a high dose of that. So, if it's something that you think that you want to do, starting to embark on that journey sooner rather than later can be really beneficial.

Some of the people who have used the framework and have told me it's been so helpful for them are same-sex couples, because they know that it's going to be a bigger investment, more work for them, more effort. So, they want to make sure that they were going in as deliberately as possible into that journey. This is an area where you actually might want to do it separately, and then come together and talk about – I mean, certainly, have the conversations. But then, go do your own research, go talk to people who have decided to have children, not decided to have children, and then come back and talk about the results because you need to both be on the same page about wanting it.

Ben Felix: That's a really interesting idea to do it separately. You co-authored this book. As you've given us a ton of your own examples, you've lived a lot of these decisions. What were your biggest learnings working with your co-author in writing this book?

Abby Davisson: Well, she is just a wonderful person. I'd say she's a national treasure because she has just turned 84, and her second husband actually passed away while we were waiting for the book to be published. She did move again; she moved into a retirement community, and someone introduced her to a widower who was moving into that same community, and they have a wonderful relationship now. They just went through the process of getting a joint credit card.

So, money and love conversations can happen at any age, is what she has taught me. Another learning that I've had from her is, our chapter on senior years at the end of the book was originally titled The Golden Years. I remember when we were submitting the manuscript, she said, "This title doesn't work for me because these are hard years." She at that time was the full-time caregiver for her second husband, who had Parkinson's. She was also witnessing a lot of her friends and peers getting sick, passing away. She said, "I go to a funeral every other week, it seems like. This isn't the golden years. You're in the golden years. You have young kids. Your friends are healthy. You can pick up and go on a trip together without someone saying, they can't go because they just had this new diagnosis. You're in the golden years."

Frankly, that, plus a lot of other things in my life helped me clarify the fact that I wanted to pull forward this idea of radical autonomy for myself, and be more present for my kids when they're in a tricky middle school age, when I'm still as physically healthy as I can be. Working with her has given me a lot of insight, and I really attribute that to her wisdom and the perspective that intergenerational relationships can offer.

Cameron Passmore: Amazing. This has been so much fun, Abby. Our final question for you. How do you define success in your life?

Abby Davisson: I love that question. I've thought about it a lot. For a lot of years, I let other people's definitions drive my own. I went to really competitive schools. I tried to reach for the highest ring that I could and ascended to a job that was once my dream job, running the foundation of a Fortune 200 company. Ultimately, I've had to decide for myself that success means to have well-being in multiple areas of my life. That means being able to have a career that pays the bills, helps me be helpful to people, feels purposeful to me, but that also allows me to spend time with my family, and play tennis every week. So, I'm really happy to be able to do all those things. I think it's really critical that everyone thinks about the definition of success for themselves.

Cameron Passmore: Great answer, great to meet you, and thanks for joining us.

Abby Davisson: Great to meet you too, and thanks for having me.

Ben Felix: Thanks, Abby.

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