SPENCER: Raffi, welcome.

RAFFI: Thank you.

SPENCER: Do you think that most people don't learn the skills they need as adults, or at least don't learn them early enough?

RAFFI: Yes, I think that there are many adult skills that people learn through trial and error or life experience, and even some that must be learned that way, but there are many others that I don't think have to be learned that way. For example, someone could be in a relationship, and the relationship doesn't work out because the two people are incompatible but there could be another relationship that doesn't work out because the two people are actually very compatible, but one of them hasn't learned some very basic relationship skills that I think could be taught in the way we teach things like math, and that's really a shame, because if they had learned those skills, that relationship could have worked out. I think there are many examples like that, which is why I'm a fan of this idea of teaching adulting skills preventatively.

SPENCER: It sounds like you think there are both adulting skills that people will eventually learn through trial and error, but maybe things could be more efficient, or their life could be better if they learned them earlier. And then there's this other set of adulting skills that many people never learn.

RAFFI: Yes, and I think it's a big hodgepodge and spectrum for many different people. Maybe there are some things everyone learns eventually, like everyone will learn how to do their own laundry, even if their parents never force them to. In fact, it's not that hard to figure out. So even if someone has never been taught in school, the pain of figuring it out is not so great that it's worth teaching something so basic in school. But there are other things where the pain of having to figure it out for yourself, or of never figuring it out, is so great that it's worth teaching.

SPENCER: Now we're gonna get into a bunch of these specific skills, and hopefully you can teach our listeners some of them, at least give them a taste. Before we do that, what are some of the categories?

RAFFI: I grouped the curriculum in the course that I taught called Adulting 101 into four categories. So I had Financial Skills, that's how to invest your money, get insurance, and so forth. There's Career Skills, how to succeed in your first job and how to build a career long term. There's Relationship Skills, in which I include how to be a better communicator, how to go about dating, and deciding if and when you want to get married. And then the last category, which is actually the first one I teach, but it's the hardest to explain, which I call Mental Skills, some combination of mental health and resilience, but just basic ways that you can think better that lead to better mental health.

SPENCER: Let's start with Relationship Skills, because I think it applies to everyone, and we've already mentioned it. So what do you think a key relationship skill is that many people don't learn or learn much later than they should?

RAFFI: A big one is how to disagree constructively. I think when I use the term disagreement, it has negative connotations for a lot of people; a disagreement must mean an argument or that there's some unpleasantness involved. But I actually think a disagreement is the best type of conversation because it means that two people have different viewpoints, and so there's more to be learned from either side. I actually spent a good portion of my career teaching what I call the art of constructive disagreement.

SPENCER: What does that mean, constructive disagreement, rather than, let's say, destructive or whatever normal disagreement would be?

RAFFI: Constructive meaning that both people can gain something. There might be an argument that's fruitless, and that would not be a constructive disagreement, but constructive disagreement means that both people, I think it requires that both people have the attitude of wanting to learn. That's the number one technique or tip that I try to teach: if you approach a disagreement with an agenda, and that agenda could be, "I'm trying to win the argument, or I'm trying to look smart in front of my peers, or I'm trying to convince the other person that they're wrong and I'm right," that is more likely to lead to it not being constructive. But if you approach with an attitude of curiosity like "I want to learn as much as possible about the other person's perspective," it will be constructive.

SPENCER: Now, of course, you can, to some extent, control your own attitude, but you can't control the other person's attitude. If the other person is not coming in with the point of view of learning, but you are, does it still help, or does it have to be done by both parties?

RAFFI: I love this question. Yes, I think this is the key question. I would break it down into two sub-questions. The first one is, "Are all of these disagreements worth your time?" The answer is obviously no. There might be some people with whom you realize quickly that you're wasting your time, or even you can know beforehand it's a waste of time to talk to them. But what I would caution people against is making that determination just by yourself and too quickly. I think we all have in our heads this version of the Overton window. That term is used to describe what's acceptable in public discourse, but we all have our own version of it in our heads, and so we think that someone with an opposing viewpoint, let's say on politics. Let's say I'm a Democrat and there's a Republican who wants lower taxes, and I think lower taxes, that's just totally outside my Overton window, that's too crazy, I'm not even going to engage with that person because they don't know their basic facts. I think most people would look at that scenario and say, "No, that person should not be outside your Overton window." The question of what is the right tax rate is still a very open debate in the world, and it's worth engaging with people. So I think most people would say, "Yes, that's obvious. Expand your Overton Window. Be willing to at least engage with someone who disagrees with you on that." But I think the problem is that most people don't have self-awareness of how narrow their Overton window is. If you give yourself the excuse of being able to say, "It's not worth talking to this person because it's not worth your time." Your Overton window might stay narrow forever. I try to encourage people to approach conversations, even ones that you think might be outside of your window, with this attitude of adventure and exploration. Like, "If this person believes that the earth is flat, that is just downright crazy. They don't know basic science." But my attitude would be, 'If there's someone who seems like a decent, reasonably intelligent person who believes the earth is flat, why do they think that? That's fascinating. I'm really curious how they came to that conclusion." Maybe at the end of the conversation, I'll come away thinking, "Yeah, they just don't understand some basic things, or they're downright stupid. That's possible." But I think more likely, I learn something about them, and therefore something about human nature.

SPENCER: I think sometimes ideas seem outlandish to us, and we may not want to engage, but sometimes ideas are just offensive to us, and I think that often turns people off from having an engagement.

RAFFI: What do you mean offensive? I struggle with this word because I think it's semantically overloaded. It can mean different things to different people.

SPENCER: Well, I'm someone who's incredibly low in feeling offended, but I'm trying to get into the mind of a lot of people who feel offended. They would be on Twitter. They feel offended. I think what a lot of people are pointing out there is that they have an emotional or negative emotional reaction to what they're reading; they feel angry at the person who wrote it, or they feel angry at the person that post is about, let's say, or maybe they feel scared.

RAFFI: I would love to address this. I think it relates to the topics that I tend to teach about related to mental skills, of how to approach situations where you think that certain emotions are going to be triggered, even if you know the situation could be good for you. Reading an opposing viewpoint, probably good for you, but if it makes you angry in the short term, it's not good for you. So how do you get over that? I also wanted to make sure first though, that I addressed kind of the second part of your first question, or at least something that I think was implicit in it. A lot of people go into these disagreements and they say, "Well, I do want the other person to have that same curiosity towards me that I'm showing towards them. I do want them in an ideal world, to be persuaded by what I'm saying." And I think persuasion is possible. It just rarely takes place during the course of one conversation. I sometimes ask people, "Think about a time that you changed your mind on a deeply held belief during the span of one conversation." And it's very rare. I think what's more common when people change their minds is that a conversation can plant a seed. It's a seed of a new idea or a new perspective, and now that seed is in the metaphorical garden of your mind, it can be watered over time. So if you give me some argument that I'd never heard of before, like why taxes should be lower, the next time I see a piece of evidence or another argument that reinforces what you said, that seed will grow into a small plant and so forth, and eventually that plant may be so big that I have a new belief in my garden. And so I think that if your approach during conversation is a good one that's coming with curiosity and you're assuming the same good intention of the other person, you might end up planting a seed in their garden of their mind that will be watered over time. You just have to be equally open to having the seed planted in your own as well.

SPENCER: I think that's a nice way to put it. Can you give us an example of how a conversation might typically go that's not so good, and then what would be a better way for the conversation to go?

RAFFI: I think when a disagreement goes poorly, it's because, as you mentioned, people's emotions flare up. The psychologist Jonathan Haidt has a great metaphor for this. He says our minds are like a rider sitting on top of an elephant, and the elephant is our system one thinking, our intuitive, fast, sometimes emotional responsiveness, and our rider is the system two, the more rational, reflective thinking. We often tend to think it's the rider who's in control, but in reality, according to many studies, it seems like it's the elephant that's in control. What does that mean? It means when someone, let's say I'm part of some group, using my example but flipping it this time, I'm a Republican, and someone comes to me and says, "All Republicans are stupid." What's actually more likely to happen is my elephant is going to react. I'm going to have this immediate, intuitive reaction of, that is hurtful, that's offensive, it's going to make me angry. It's going to make me see the other person as an enemy and not a friend. All these things are going to happen before my system two thinking, my rider, can kick in. When my rider kicks in, it actually simply justifies the conclusion I've already reached. We all like to think that our rider is going to be more reasoned, but what happens more often is our rider thinks, "Yes, that person is denigrating you. He's bad too. You should treat him like the enemy." This whole framework around the rider and the elephant is helpful to keep in mind because it teaches you that when one of these flare-ups happens in a conversation, you can recognize the other person is struggling with that same inner turmoil and do what we call appeasing the elephant: trying to realign or reset expectations around the conversation, to lower the temperature, lower the flaring up of our elephants. There are some basic ways of doing that, like trying to show that you're on the same side, like, "Oh, it sounds like what I said just offended you. I apologize for that." Of course, you can always apologize for things like that. More importantly, you can say, "I want to learn what your perspective is. My goal here is not to offend you. My goal is not even to convince you that you're wrong. My goal is to understand where you're coming from, and that requires some effort on both of our parts, but I'm going to do my best to try to listen and understand." That's one thing you could say. What it's trying to do is establish a shared intent. The conversation is not a zero-sum game; it's actually a positive-sum game, where if we both learn, then we've both benefited.

SPENCER: Okay, so it seems like there are at least two pragmatic tips there. One is coming into that conversation really trying to learn from the other person, and the other is tracking the elephant, what are the emotions going on here? Making sure to deal with that by making the person feel comfortable, or if they're getting upset, addressing that before you proceed. Any other specific tips for having constructive disagreements?

RAFFI: I can try to clarify that with a framework. The framework is how to engage in empathetic listening, and it's especially useful when you disagree with someone, or when someone says something and your initial reaction is to feel hurt by it. The first step is just to acknowledge what they said. Be like, "You said this, that sounds like it was hurtful to you or offensive to you. I'm sorry for that, acknowledging their emotional state." The second step is to ask questions and try to understand better what their viewpoint is, so that you can do the third step, which is to repeat it back to them. I want to get to the point that I've understood your perspective so well that I can repeat it back to you, and you would say something like, "Yes, that's exactly what I mean. You said it even better than I could say." Only after that third step would I suggest going to the fourth step, which is sharing your own perspective, and then finally, trying to problem-solve together.

SPENCER: It reminds me of Rapoport's rules, if you're familiar with that. This idea that to do a really good job of debate, you should be able to explain your opponent's point of view as well as they can, or even better, so that they're like, "Thank you. You explained it so clearly." If you haven't achieved that bar, then you may not be ready to really have a debate with someone.

RAFFI: Yeah, exactly. If I'm reading into your example correctly, it's in the context of debate where your goal might be to try to outwit the opponent or prove them wrong. Of course, that's a super useful tool because if you can articulate their argument better than they can, you can then use it to your own rhetorical or logical advantage. But I'd say even in a conversation that's not adversarial and is intended to be constructive, it's so helpful because it really proves what I was saying earlier about showing that you're on the same side as the other person. If I'm able to articulate what you're saying better than you can articulate yourself, you're like, "Yes, you're on the same page as me. You understand me. You're actually trying to make an effort here."

SPENCER: I think those rules were also designed to create better, more constructive conversations as well, so it could be interesting for people to read about. Okay, so we've talked about disagreeing constructively. I totally agree with you, this is an incredibly important life skill, and we all face this when we talk to family members, friends, or on the internet. What's another relationship skill that you think is really essential that a lot of people don't learn early enough or don't learn at all?

RAFFI: I think a lot of people don't learn about dating. There are a few things here. One of them is that a lot of people grow up with these myths around romantic love that get perpetuated by pop music and Disney movies. As we alluded to earlier, some people naturally grow out of these and realize that they're myths. But for some people, the myths kind of stay with them for their whole life and poison all of their relationships. Another thing is how people approach dating. There are, I'd say, a great many people who have the long-term goal of wanting to end up with a single partner for life, but the way that they actually go about dating is sort of counter to that goal.

SPENCER: So what are some of these myths people encounter?

RAFFI: I think one of them is that your ideal partner should fulfill all of your needs. There's this idea that once you find your true love, you won't need anyone else, and they can provide for you in every way: emotionally, spiritually, financially, sexually, and so forth. If you meet a partner who can provide a lot of those things, that's fantastic, and they're probably more likely to be your "soulmate." But it's completely unrealistic to think that you will only ever need one person in your life. It's very likely you will continue to need to rely on your parents, your siblings, your children, your extended community, friends, and so forth. The myth can be harmful to people when they say, "Oh, my partner's great in these 99 ways, but there's this 100th way that they don't provide for me. They don't give me the same emotional support when I'm talking that my best friend does." Therefore, this person is not the right fit for me. I think that could be harmful because that person may very well be the right fit for you if they're ticking 99 of the 100 boxes, and the ideal life situation for you is you end up marrying that person, but you also keep your best friend because you do need your best friend, too.

SPENCER: Yeah, I think that's very wise. The other reality is the chance that someone fits every single need you have so perfectly is really, really low, but the chance that they are highly compatible with you is much less low. So you can kind of get a lot of gains there.

RAFFI: There's also, I think, a trope that may be less in Disney movies, but more in romantic comedies, that you start feeling attracted to someone else, and because you're attracted to someone else — I'm saying deeply attracted, not just sort of at first glance — that means there's something wrong with your relationship. A lot of the time, it's not true. It's perfectly human and normal to become attracted to other people. The question of how to make a relationship survive, thrive, and succeed in the long term is how you overcome those inclinations and stay committed to your partner. What often happens in these romantic comedies is you have someone who's in a relationship and it's fine, and then they meet this new person. The new person is more exciting, and that's the person they end up with at the end of the movie. Sometimes those are terrible endings in terms of what they teach, especially young people. What if you were actually the nice guy at the beginning who was with a nice girl, and there was someone else who came in and totally disrupted the relationship? That might actually be the untold hero of the story. It's basically teaching people implicitly that the happy ending is the one where you abandon your safer, stable, or normal partner and end up with a person who you're wildly attracted to. Maybe that's the right move for some people, but obviously not for everybody.

SPENCER: It seems to me that this is something there are individual differences in. Some people, when they're in a romantic relationship, seem to have eyes only for that one person, whereas other people, even in a deeply loving and happy romantic relationship, still feel sexual attraction to other people. I think maybe that can complicate the story because people have really different experiences with this.

RAFFI: Of course. I think it just proves the overall maxim here that there's no one size fits all for something as complicated as love or human relationships. Everyone has their own needs and proclivities. I think the meta-myth is that there is a one size fits all, or at least that there's a certain model that works for other people, therefore it'll work for you. You can always learn from other people's models, and you can take people's good examples and glean very helpful wisdom from that. But to assume that just because every Disney movie portrays love the same way, that love must feel the same to me, is probably going to set you up for disappointment.

SPENCER: You also mentioned that you think that dating itself can often be done in an ineffective way. What are some of the problems with the way people try to date?

RAFFI: I think that a lot of people, I'm going to generalize, but I think it's true. On average, a lot of people know they want to end up together with one person in a long-term monogamous relationship, but they think they have all the time in the world to get there. Especially because most of my audience is people in their 20s. Your 20s is a time for exploring and not committing. I think that might be true for some people, so I'm not going to give a one size fits all approach. But I think the danger of that attitude of infinite exploration is you don't realize how long it takes to build a relationship or how long it takes to find the person you want to end up with. You might get "lucky", and the first person you date might end up being your long-term partner. I personally am fortunate to have had that happen to me. The first long-term relationship I was in ended up becoming my marriage, which is amazing. But not everyone gets that lucky, and oftentimes it can take a lot of trial and error to find that person. If you're not lucky enough for it to happen soon, it might take you all of your 20s to find that person. Let's say you're living in a world in which it's going to take 10 years to find that person, but you spend those 10 years doing something else, which is exploring in other ways, like dating people you know you're not going to end up with or saying that, "I'm so busy with my job, I'm not going to date at all." By the time you're 30, you're not married. If it's going to take you 10 years, you'll only be married when you're 40, and for a lot of people, biologically, that might be too late to have children. That kind of attitude of having all the time in the world can set people up for failure.

SPENCER: How do you think about the fact that when people haven't dated much, it can be hard for them to evaluate if someone's a good partner, or what it even means for someone to be a good partner, or what it is they're really looking for? Is there some amount of exploration needed to kind of understand those important things?

RAFFI: Absolutely. I have two frameworks here that might help. The first one is this idea of approaching dating as a treasure hunt. I am naturally an introvert, and I know a lot of introverts like me don't like the social situations that might lead to meeting new people, especially new potential romantic partners. Going to parties, going out on activities, asking friends to set you up — these are either slightly uncomfortable or slightly unpleasant. I think this framework can be helpful for that type of person to say, "Your treasure, the love of your life, is waiting for you at the end of this quest. Every single step you take on this quest is getting you closer." Even if it doesn't feel like it, if you went to a party and didn't meet anyone you really clicked with, that's still part of the process of having to do that in order to find the treasure. Another thing that good heroes do when they're searching for treasure is maximize their odds by trying many different tactics at the same time. You might decide, "I am going to go into more social situations or meet more people. I am also going to ask all your friends to set me up, and I am going to be very clear about what kind of person I am looking for, treating it like an adventure," where you can diversify the ways in which you're placing your bets. The second framework that I think is helpful for someone who's in a relationship and is not sure if they want to commit is this idea that you can group you and your partner's compatibility or lack thereof into three piles. There's the good pile: these are the ways in which we're good together. The bad pile: the ways in which we're not. And the unknown pile: like, "We haven't yet encountered a scenario where we have to deal with a difficult family member. We haven't yet encountered a scenario where we're living in the same place and have to deal with cleanliness and that kind of thing." If the good pile is ever bigger than the bad pile plus the unknown pile, it's probably worth committing. What I mean by that is, if you basically say, "Okay, there are still a bunch of unknowns," but even if these unknowns turn out to be all bad, the good pile is still going to be bigger than them, then it's kind of a math no-brainer, like, "Yes, the good pile is bigger; you should make the commitment." The hard part there is determining what the actual unknowns are or there could be infinite unknowns, but how do you narrow it down to something finite? How do you determine when one of the unknowns is "solved" or not? I don't think there are any easy answers there, but I think what the framework encourages people to do is to think, "Just like the treasure hunt, we can experiment here. We can try to put ourselves in these situations. We can try to talk about things we've never talked about before and unearth all those unknowns in order to get to the answer faster."

SPENCER: That's interesting. So that would suggest that if you don't have many unknowns left, so the unknown pile is very small, then if the good is just slightly better than the bad, that's enough to commit. Do you think that's true?

RAFFI: It depends on the situation, for sure. I would probably advise someone differently, depending on the specifics of their situation. But as a general framework, I think what it helps people do is also get faster to the part where they reap the benefits of commitment. One of the benefits of commitment is you don't have to worry about this at all anymore. Every unknown is no longer a question of, "This could be a reason that we're going to break up or not end up together." Rather, every unknown becomes a fun mystery like, "I don't know this value; let's figure it out. Worst case, it's a bad thing, but we're still going to stay together. Our question is not going to be, should we break up? Our question is going to be, how do we resolve this difference, or how do we continue to live with each other despite having these differences?"

SPENCER: My mom once said something I thought was very wise, which was, "When looking for a partner, look for someone whose flaws are flaws that you don't mind so much." I found that really helpful because it orients you towards thinking you're not looking for a perfect person. Every person is flawed, no matter who they are. You want someone whose set of flaws is not that big a deal to you because it doesn't have any deal breakers. It doesn't make you unhappy, etc.

RAFFI: Yeah, I think one person's flaws are another person's benefits or pros. There was an episode of How I Met Your Mother that put this really well, where there are some quirks about a person that might really irk you, but to someone else, those quirks are actually really endearing and lovable. It's kind of taking your mom's advice one step further, not only finding someone whose flaws you don't mind, but actually finding someone who, while they have flaws, you would love those things about them.

SPENCER: It sounds like one thing you're emphasizing is that getting into a relationship sooner has benefits, like you get to enjoy that relationship for longer, and you can avoid the stress of looking, is that right?

RAFFI: Absolutely. And again, it depends on the person. Some people might know they never want to be in a long-term relationship. Some people might know they always want to keep dating. Some people might not want to be monogamous. All those people might have different models, and that's totally fine. But I think for the type of person who knows they want to get married, which, again, I think is the majority of people, according to most survey data, the sooner you can get to the point where you feel like the relationship is serious, the sooner you will learn the things about serious relationships that will set you up for success, such as how to be a good partner and how to reap those benefits of commitment.

SPENCER: It seems to me, especially if people want to have kids, that there's value in finding that partner early — especially if you want to have multiple kids — it makes it easier just on a biological level.

RAFFI: Absolutely. And I think similarly, a lot of people say that they want to have kids in the future, but they "don't put their money where their mouth is," meaning they don't prioritize the steps that it takes to get there, the first step for most people being to find that long-term partner. I just want to be careful here because I know that everyone has totally different opinions on this topic, and a lot of their moral values play into it. I definitely don't want to impose my own values. I'm hoping that nobody can even guess what they are, although maybe they can. It's more like if you say you're the kind of person who, "I want to get married and I want to have kids," you may not have as much time as you think you do, in part because of that biological ticking clock that applies primarily to women. There's nothing you can do to guarantee that you're going to have the outcome you want on the timeline that you want. But the best thing you can do to maximize your chances is to take that entire process seriously and commit to trying to find that commitment.

SPENCER: Switching topics, now. Let's jump into financial skills: what's an example of a financial skill you think people don't learn or don't learn often, or don't learn early enough?

RAFFI: There are many, but I just mentioned paying taxes. It's actually crazy to me. You are required by law to pay your taxes. If you don't do it, the penalties escalate up until the point that you can actually go to jail, and yet, nobody ever teaches you in a public education system how to pay your taxes.

SPENCER: Is it one of those things, though, where everyone kind of figures it out anyway?

RAFFI: Well, many people don't figure it out because they either never pay their taxes, or they never do it properly, or they outsource it to an accountant. I don't think there's anything wrong with outsourcing it to an accountant. It may be worth it if it's not worth your time to learn or to do it properly. Plenty of people do that, and that could make sense, but I think there are a bunch of problems with assuming you're going to do that from the outset. The first one is, you may not be able to afford it. It's a lot cheaper to do your own taxes, and you may not be in a financial position to pay an accountant forever. Second, you just won't learn how the system works. Therefore, you won't know how to make certain optimizations in the way you live to save on taxes. I think a lot of people don't realize in the long term how much taxes eat out of your long-term net worth. Therefore, some small adjustments you can make to the ways in which you live and earn and pay can save you a lot of money. I find that every year when I do my own taxes, and I say do my own with air quotes that you can't see because I use TurboTax, but TurboTax is still walking you through step by step. I notice, "Hey, if I'd done this thing differently, I would have actually saved money at the end of the year." Every year I learn new things like that.

SPENCER: So when do you think people ideally would learn how to do their taxes? Because I'm imagining if there was a class on doing your taxes in ninth grade, pretty much no way I would have retained any of that today.

RAFFI: Absolutely. I think it's most useful the moment you have to do it. When I talk about teaching adulting skills, I think they're most useful to teach when people have to actually start doing them because then the knowledge feels more urgent.

SPENCER: So maybe you could just give us a little taste. What are some things that people should know about doing their taxes that maybe they don't?

RAFFI: One of them is about credits versus deductions. A lot of people get these terms confused. I'm going to try to explain it in a way that normally visually helps. A deduction is saying that we're deducting this amount from my income. Let's say I earn $50,000 and I donate $1,000 to charity. I can deduct that $1,000 from my income for tax purposes, which means I'm only going to be taxed on the remaining $49,000. Let's assume my tax rate, just to keep it very simple, is 10%. That means I'm going to have to pay $4,900 in taxes. If I hadn't donated to charity, I would have had to pay $5,000, so that deduction was worth 10% of the amount that I deducted. That $1,000 donation saved me "$100 in my taxes." A credit means you actually don't pay the taxes on that amount. If you get a credit on something, it means that, let's say, a credit of $1,000, you actually get $1,000 back clean, not 10% of it on your taxes. These laws change all the time, so I'm not exactly sure what they are this year, but there was a year in the past where for child care, you could do a deduction and/or a credit. Obviously, the credit is better. It could be worth up to 10 times as much. You kind of had to figure out, do I take the credit on this amount? Do I take the deduction on that amount? Understanding that distinction that year, I think, saved me a couple thousand dollars.

SPENCER: Oh, nice. I do see people confused on this a lot. For instance, I often have seen people accuse billionaires of, "Oh, well, they just gave to charity because it saved them money on taxes." And you're like, No, there's no way that wasn't a huge net loss that donation."

RAFFI: Yeah, it basically means that if their marginal tax rate was 50% all in, that includes all the federal, state, and local taxes they have to pay. I think 50% is basically the upper limit in the US. That would mean that the donation only cost them about half as much as what they actually paid because the other half could be deducted from their taxes.

SPENCER: Exactly. So they still lost money. It's just they lost less than they would have without the tax deduction.

RAFFI: Sorry, to clarify, they would deduct the entire amount for their taxes, but half of that would be money back to them, because half of that is what they would have paid in taxes.

SPENCER: Very interesting. Any other tidbits on taxes that you think people should be aware of?

RAFFI: Tax is the most boring topic in my book. I walk through the entire form, step by step, which I think is a much better way to do it, because you see every question that you're asked and how to answer it. But I think the most helpful thing I wish I had known is that you have to save your records for up to seven years, because the IRS, which is the federal agency in charge of collecting revenue, meaning that does the taxes, can request information from you going back seven years. They say, "Even though you submitted your taxes for 2024, there's something you did in 2018 that we're not sure about, can you show us the W-2 that you still have, or something like that," and if you don't have it, you could get in trouble, or you would have to be audited, or one of those things could happen. And so I actually, way too late in my life, started keeping a literal filing cabinet of all these forms that I have going way back into the past.

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SPENCER: What about IRAs? I feel that's a huge topic that people don't understand.

RAFFI: Absolutely. A big question that people ask is, should I invest in a Roth IRA or a traditional IRA, because they're taxed differently. I think in order to understand that, you have to rewind a lot to understand not only what an IRA is, but how tax-advantaged retirement accounts work in general, and why a tax-advantaged retirement account matters. What is a retirement account? Why invest? What is investing? And how does it work? Is it okay if we rewind all the way to that?

SPENCER: Sure. Yeah, let's do it.

RAFFI: The other big secret that people don't tell you is that if you don't save money for your retirement, you will likely not have enough money to retire on. There is a social security system in the US, but it doesn't provide for most people enough to live comfortably, so they have to supplement that with their own savings. Of course, that could get worse over time, because there's all kinds of talk about how Social Security benefits might be cut or even eliminated by the time our generation is retired. So you have to save your own money. Seems like a lot of money. Let's say you want to retire at age 65 and you hope to live to age 90. That means you have to have at least 25 years' worth of living expenses saved up. It's hard enough to save up one year of living expenses. How do you do that? Well, there's this magical thing called investing, which means you don't have to save as much money as you think you do, because the small amount that you save can accumulate over time. Investing just means saving money in a way that's going to earn you more money over time. A very basic example of investing is if you put money into a bank account, it earns you interest. Most people are probably familiar with that. That is a form of investing. You put in $100; if it earns 5% interest, you're getting $5 added to your bank account, and that $5 compounds, meaning every year, not only are you earning interest on the first $100, you're also earning interest on the $5 and then interest on that and so forth. The amount you're earning every year grows. That's compounding. It's essentially exponential growth. There are other forms of investing too. Most people commonly think of investing in the stock market. It's putting your money in a way that's going to earn you more money over time, so that it's much more affordable or easier to save for your retirement.

SPENCER: Now a lot of financial gurus will say things like you should put a fixed percentage of your income into your investments automatically every month. Is that what you would advocate?

RAFFI: It really depends on the person and their situation. I typically offer a multi-pronged approach for what to do with your money before you get to the point where you could take that money and spend it on something like leisure. Some of those steps include getting insurance that's necessary to protect yourself, building up some emergency savings, and at some point, yes, investing that money, probably into a tax-advantaged retirement account. I can try to answer that question now about IRAs, which is when you invest money, it's going to grow over time; that growth is going to be compounded, but taxes eat away at that compound growth, because you're going to have to pay a portion of your gains every year back to the government in the form of taxes. The government has some carve-outs you can use; they're called retirement accounts, and they are tax-advantaged, so they've turned certain tax benefits. Some types of accounts are not taxed at all until you withdraw the money. Some are taxed when you put the money in, but then their growth is not taxed. It gets sort of confusing, but the ultimate purpose of them is if you know that you are going to be saving this money for your retirement and not using it sooner, you might as well put it into one of these investment vehicles so that the taxes won't eat away at the growth.

SPENCER: It can make a really huge difference, whether you put money in an IRA or not?

RAFFI: Absolutely. If we're talking about saving money over the course of your lifetime for retirement, I've done calculations. It depends on the person and their income, but it could save you hundreds of thousands of dollars, up to half a million dollars, in your total savings, whether you remember or not to put the money into one of these tax-advantaged accounts. The one that probably most people are familiar with is a 401(k). It's a kind of IRA that's provided by your employer.

SPENCER: You mentioned the stock market. Is that what you think people should be doing with their savings when they know they're not going to touch it for a while?

RAFFI: For the most part, it tends to be the best way to invest. I think I should clarify what I mean by the stock market. People can obviously pick individual stocks, Amazon, Apple, whatever, but they can also invest in an index fund, like an S&P 500 fund that tracks the 500 largest companies. What's interesting about that is that an index fund tends to smooth out the volatility of individual stocks. Some years, Amazon may go up, Apple may go down, but if you've diversified between the two, you kind of benefit from that hedged risk. The S&P 500 index fund itself can carry its own level of risk because obviously there are some years when the entire stock market goes down. People remember 2008-2009; the entire S&P 500 as a whole went down because the average company went down in value. That is the risk of investing. Your money may not grow; it might actually depreciate over time. But in order to determine if the S&P 500 is a worthwhile investment, I think it's worth looking at long time horizons. This is an analysis that I've done; I haven't seen other people do it, so it might be worth explaining how risky it is to put your money in the S&P 500 over a long period of time.

SPENCER: Because that's the thing that scares people, like, "Yes, the stock market, on average, has done really well, but what if, for seven years, it does dismally badly, and then you just don't have nearly as much money for your living expenses?"

RAFFI: Absolutely. I got data from an economist that goes back about 150 years of the US total stock market, essentially like the S&P 500, but it's even more comprehensive. I looked at the returns over different bands of time. As a basic example, let's take the band of one year, the best possible case of how much your money could have returned over one year. I don't remember the exact numbers, but it's somewhere around 50%, meaning you could have earned 50% on the money you put in. The worst case is negative 40-something percent. It could have lost almost 50% of its value. I think that was if you put your money in like 1931 or 1932, sometime during the Great Depression — I don't remember the exact year — that's the worst case. But what if we expand the time horizon to five years? What is the best case growth for five years and the worst case growth for five years? It gets a little bit narrower. I don't remember the exact numbers, but the best case is something like 20-something percent, and the worst case is negative 20-something percent. As you say, "I'm going to invest my money for longer and longer periods of time," that range of possible returns gets narrower and narrower, down to the point where you're saying, "I'm going to invest this money for 30 years." So put it in today, not touch it for 30 years. What's the worst possible case? The worst case is it depreciates by about 6%, and the best case is it appreciates by about 11%, and that's based on 150 years of history.

SPENCER: Yeah, that's really cool. Now, of course, we don't know about the future. The future could be different than the past. Maybe a civilization will get destroyed, and there will be no stock market. But it's really cool to see that as you aggregate to longer and longer time frames, the confidence level that you'll appreciate in capital, not losing it, goes up and up.

RAFFI: And not only appreciating but appreciating in a 6% to 11% range, which is pretty incredible when you do the calculations on how much that can compound. That risk you mentioned is very real. It's always possible this 150-year trend won't continue. Empires have fallen in the past. I just like to remind people that 150 years of history does include the Great Depression, and includes two world wars, September 11, and everything in between.

SPENCER: Right? So we got a lot of stress testing, at least. Do you advocate people invest internationally?

RAFFI: Not in particular, I haven't seen much evidence that it's better than the US economy. In fact, it seems like it might be worse, but I've only done this analysis on the US economy.

SPENCER: If you read the prospectuses of any kind of investment vehicle, they'll always say, "Past performance does not imply future performance." They kind of have to say that. But to what extent do you think that is really true?

RAFFI: I think it's extremely true, and all the evidence I've seen supports it. There are cases where you can have a fund manager beating the index, performing better than the S&P 500 for one year, two years, three years in a row, and they're no more likely to beat it in the fourth year than any other index fund, or any other fund manager picked out of a hat. Past performance does not indicate future performance, no matter how long your track record is. According to the studies that I've seen, which is pretty amazing, it basically means that nobody can consistently beat the average, the average being the S&P 500, so you might as well invest in it.

SPENCER: It seems to me there are funds that have clearly beaten the average systematically, like Renaissance Technologies being the famous example where, if I'm not mistaken, they've beaten the average of the stock market by 40 or 50% a year for easily over 25 years. To me, that seems impossible to happen by chance, but they're obviously a crazy outlier. I don't know what you think of that.

RAFFI: Yeah, I'm fascinated by Renaissance Technologies. I love them as an example for that reason. What's interesting is, and it's probably a caveat I should add to the claim I made earlier, these are all publicly accessible funds that the average Joe Schmo can actually invest their money in. The original Renaissance fund, if I understand correctly, is closed to the public; it's actually only a lot of the original owners and employees who have access to it. All the other funds they've started since then on the side have not actually outperformed on average. Part of the reason for that is the way their quantitative trading algorithm works. It's kind of capped by how much they can trade. They don't actually want to raise more money for that fund because it might affect their performance.

SPENCER: I think it's such a good example for that reason. My understanding is they kicked out their investors ultimately, or maybe they allowed a small number of investors to maintain their positions and they just filled it with their own money. Imagine you had this money-making machine; would you really want other people to use it or just want to use it yourself?

RAFFI: I think that's one explanation, but I think the other explanation is actually that it won't work if there's too much money, because some of the trades they're making, I don't know what they actually are, but just as a hypothetical example, if they're trading on some commodity in Zimbabwe and they're trading literally the size of that entire market one day, there's not more that they can physically buy up of it.

SPENCER: That's exactly right, because if it had unlimited capacity, then you might as well trade it yourself for your own money and let other people use it. But no, you're absolutely right. It's limited capacity. My understanding is actually they give back a lot of money to investors every year because they can't grow it. And you're absolutely also right that the much larger funds that they've released that are open to a much broader swath of the public haven't done nearly as well as their flagship fund.

RAFFI: And one thing that I find amazing is that everything we're seeing about Renaissance Technologies was once true of index funds, like these S&P 500 index funds. They were not open to the public. They were very tricky to get into. You had to have a certain amount of money and so forth. One of the big innovations in finance, and I think this was in the early 1970s, was making one of these funds, John Bogle, who started Vanguard, accessible to your average retirement investor, just someone who's putting their money away for retirement. I often like this question of what are the wonders of the modern world? With the seven wonders of the ancient world, I think one of the wonders of the modern world is a publicly accessible index fund, because it's basically democratized access to the prosperity of the stock market.

SPENCER: Let's switch categories and talk about career skills, because this is something that almost everyone has to face multiple times in their life and has such a big impact on what they spend a lot of their time and their life doing. Your job is one of the biggest sources of your efforts and time.

RAFFI: Yeah, the way that I try to describe it to someone who is just starting out in their career is you actually have two jobs. The first job is what you're doing all day, trying to succeed in your job. The second one is figuring out what the heck you want to do with the rest of your career. That often takes as much time, or at least is worth putting as much time into, as your day job. It takes a lot of exploration, talking to different people, reaching out, networking, and trying different things so that you can determine, "Am I in the right place, or do I want to move to somewhere else that's going to advance my career?" I think a lot of people don't put that amount of thought into the very first full-time job they take either because they don't know enough, because they're coming out of college, or they just don't have the time to do it. But once you're in that first full-time job, a lot of people start to realize, "This may not be right for me. What else do I want to do?" That second job of figuring it out is a huge time commitment.

SPENCER: It's so tricky, because if someone feels they're coming from a place of weakness where they're like, "Okay, well, I just needed to get a job. I'm just looking for someone who's willing to hire me." It feels difficult to then think about what their long-term goals are, because they're merely trying to put food on the table.

RAFFI: Absolutely. And I think that's why I try to describe it as having a second job. If you don't have a job at all, you have one job, which is to find a job, because most people need the income. Once you have that job and you have the income, you now have the ability, but also, in some ways, the impetus, to figure out if you should find a job that's going to be more advancing of your career in the future. One of the reasons that matters obviously includes your own personal fulfillment. But just from a financial standpoint, you can agonize over picking different investments, and we talked about the S&P 500 versus picking stocks and so forth. But even getting a raise of $1,000 at work that sticks with you over the course of your career — your income is permanently $1,000 higher and growing — makes more of a difference than a 1% return on your investments that you're putting towards your retirement for most people. So figuring out a job where you can get paid more matters a lot more than agonizing over investments. In the long term, the way to find the jobs that are going to pay you the most is to find the ones that align the most with your unique superpowers.

SPENCER: Yeah, could you unpack that a bit more about aligning the most with your unique superpowers?

RAFFI: Everyone has strengths and weaknesses, and I think what I learned early in my career is that smoothing over my weaknesses might help my career a little bit, but not nearly as much as leaning into my strengths. Pretty much every successful person I've met has figured out what it is that they're uniquely talented at better than all of their peers and tried to make that into their entire job. If you think about the market, the job market is one giant competitive environment. You're going to outcompete if you find your niche, and everyone has a niche. It's just that the niche might be really hard to figure out, because your niche may not be, "I'm the best writer." It might be, "I'm the best writer at this very specific type of thing," and you have to figure out what that is. Some people's niche might be a combination of three different superpowers, like, "I'm really good at explaining things, and I'm really good at talking to people, and I'm really good at convincing people," and that might lead you to become a salesperson or a politician or something like that. The faster you can figure out what your superpowers are, the faster you can find a job that takes advantage of them, and long term, it's going to maximize your earning potential and your personal fulfillment.

SPENCER: I think that's a really nice way of thinking about it, although I will say that sometimes I feel that people have a superpower, but it's not being unleashed because of some weakness. They're an incredible writer, but they seem to not have the discipline to write daily, so they only write three things a year, or whatever they get done, or they agonize over their latest article. So I'm just wondering how you think weaknesses fit into that.

RAFFI: I wouldn't say to ignore your weaknesses completely, because, as you're saying, if they serve as a blocker, it might be worth trying to overcome them. But in your example, it might turn out that no matter how hard you try, even if you spend your entire life, you cannot overcome that weakness of not having enough discipline to sit down and write for four hours a day. Then maybe you shouldn't become a writer, because writing is not truly your superpower. If it was, you wouldn't have that weakness going with it. I think that weaknesses should be worked on to the extent that they feel like they're really inhibiting you and blocking you from unleashing your full potential, but your full potential is on the side of those superpowers, not on the side of being a perfectly well-rounded person who doesn't have weaknesses.

SPENCER: It's interesting how school tries to get us to be well-rounded. Often, it makes us study a wide variety of subjects, and it grades us on each of them equally and averages the scores. It's like, "Well, in life, it actually is much more important that you're really good at some things, not that you're able to do, on average, well across a huge range of disciplines."

RAFFI: There's a benefit to that for sure. In other school systems, like Germany and France, they have you specialize early. I think there are pros and cons, because you might argue that when you're a child or even a teenager, you still need to be exploring these other things to figure out if they're a superpower or not. There are some people who are bad at math in fourth grade but start getting better at it when the math gets more abstract, like in geometry. I'm not exactly sure what's the right age to start doing that, but what feels obvious to me is that by the time you're in a full-time job, when you're 18, 19, 20, 21, or 22, you have enough maturity and brain development to basically start trying things and get a sense of whether or not they're truly a superpower. In that sense, you want to force yourself into as many niches as possible to see if they're working for you.

SPENCER: Yeah, I agree. It's good to expose young kids to a lot of different things. I just mean that the evaluation metric is evaluating you across all of them, which can give you the sense that that's how you're successful in life, is being good on average at a super wide range of things.

RAFFI: Exactly. If only grading was more like a Strengths Assessment, where it could say, "Well, what you've determined from this exam is not that you're an A student or a B student. We've determined that you're an A plus student when it comes to these things, and you're a D student when it comes to these other things. And maybe you should orient your career more towards the A things."

SPENCER: Yes. So what do you think people can do to approach finding a job more effectively?

RAFFI: I think the first step is to realize that most hirings don't happen based on job postings. There's some study that was done on how many jobs are actually filled because they saw a job posting and applied, versus how many were done through a much more informal process, and the latter happens more frequently. I don't think it means that there's some vast conspiracy or some shady underbelly where it's all about being elite and being connected. It just means that a lot of the time, the best way to get jobs is to establish relationships with people and get to know them, especially in industries where you want to end up working. When I was younger, I would say, "I hated networking," even the word itself kind of made me uncomfortable. It gave me a little bit of a gag reflex because it felt so uncomfortable. But I changed my attitude towards networking, and I think that helped a lot. In the past, I thought it was like, "You have to go to these fancy events and shake hands with people and drink cocktails," but I realized this is actually just exploring the things you're curious about by talking to interesting people. If you think, even if this is a distant thought in the back of your mind, "Hey, I might want to be a graphic designer one day. That seems cool," you can let that linger in your head, or you can say, "I'm just going to try to find a graphic designer who I really like, and I can try to talk to them and learn more about their talents and where they come from, and what they think about their work," and so forth. You're kind of killing two birds with one stone. One is you're figuring out what that job really means and whether or not it's actually appealing to you. Second, you're starting to network, to meet people who work in that space. What I suggest that young people do is basically look at what jobs, at least on paper, seem the coolest to you. Go on LinkedIn, find some people who have those jobs, reach out to them, and try to have a conversation. The point of the conversation doesn't need to be extremely pointed or like, have a specific goal that you're trying to get something out of them. It's more about just learning about them and asking them questions. Those people are happy to talk about themselves and tell you about their work and their lives. At the end of the conversation, say, if it's true, "This was great. Are there two other people I should talk to who'd be interesting to me?" Then your network starts growing exponentially.

SPENCER: One thing I find really useful at networking events is to focus on meeting a bunch of people there, but not lingering with people that I don't vibe with. I want to meet 10 people at this event, but I'm really looking for the people where I feel we have a vibe. If there's some way that we might be able to benefit each other from the point of view of business, that's great, but I'm not going to stay in a conversation with someone where we're just not gelling, just because there might be some kind of possible business advantage.

RAFFI: Absolutely. I think of it similarly to how we were talking about dating and going to parties. For an introvert like me who doesn't intrinsically enjoy parties with lots of people, if the purpose of the party is to make new friends or find a potential romantic partner, the goal is to meet that person, do the best you can with the conversation if there's loud music playing, but then eventually, in the business world, you take that conversation offline, follow up with that person later, and find an opportunity to actually get to know them. I'd say the same thing about networking events. I personally have never liked those, and to me, the purpose was always to find the people you might click with so you can then follow up with them and build a relationship.

SPENCER: Yeah, because realistically, usually you're going to have to build a relationship anyway for that to be a valuable connection in many cases. You sort of have to have that underlying, "Oh, I like this person, and I want to get to know them better."

RAFFI: Yeah, my recommendation is to follow your curiosity. That's what I do. If someone doesn't feel interesting to you, then there's a limited amount of time for which you can fake that you're interested in them. And it's more like, "Wow. Someone seems fascinating, what they do interests you, and there's more that you want to learn from them." Then when you follow your nose on those things, one person will lead to another person. Eventually, you'll have a network in a space that actually excites you.

SPENCER: It also seems to me that networking, in a positive sense, is something that really takes years to develop. It's not something that you can do quickly. It has to be a longer-term endeavor.

RAFFI: I think that's definitely true for building an entire career. Your network will grow over time, and that exponential growth will pay off the most later on. But I also think people find that their networking leads to opportunities much faster than they'd expect. I think about this in the context of my own childhood. I moved a lot, and every two years or so, on average, my family would move, and I'd have to make new friends. I found that it always felt like it took about a year to feel like I had new friends. During that entire first year, it felt like I was almost getting nowhere. I was trying to get to know someone or break into a social group, and I was lonely. Then the one-year mark would hit, and I'd be like, "Oh, now I actually have friends, solid friends, or multiple friends." In my observations of working with young people, it seems like that tends to happen. Maybe the timeline is similar. It feels like you're not making any headway, and then suddenly you look back, ""Oh I realize I've made a lot of headway." In just a span of one year, these connections can start to help you.

SPENCER: What about the topic of figuring out what you want to do with your life? We've talked about looking for your superpowers. What are other aspects of that you think are important?

RAFFI: The biggest one comes from a field in psychology called Adult Development. The theory goes that just as children go through developmental stages, adults do as well. However, unlike children, the developmental stages of adults are not tied to certain ages. Even though most two-year-olds can start forming words and sentences, some adults may never graduate from one stage to another unless they put in the conscious work to make that transformation happen. The reason I bring this up is there's a key transformation in this theory, where people go from one step to another. The first step is called the socialized mind, and the next one is the self-authored mind. The socialized mind is the stage that most adults are in, where you are primarily living your life according to what you think other people expect you to do. You have all these ingrained beliefs that come from what your parents told you when you were young, your teachers, your peers, and now that you're a grown-up, what your peers think of you, your bosses, and so forth. You have this internal compass, and most of the time that internal compass is actually wired towards the direction of some kind of Frankenstein version of all those people and their expectations, or at least what you think they are. The self-authored mind is graduating from that and determining for yourself where the compass should point, going through this critical examination process of, "Where did these beliefs that I have actually come from, who said them to me, do I still agree with them, what is the evidence for or against me continuing to believe in them?" and then coming to the conclusion of, "This is what I actually want from my career, my relationships, or my life." If you don't go through that process, you might continue living your whole life according to this weird Frankenstein monster of everyone else's expectations. That framework can very much apply to someone's career. For example, "I want to be a doctor." Why did you want to be a doctor? Is it because you admired a doctor when you were younger? Is it because your parents told you to become a doctor? Is it because one of your friends said, "I think doctors are so hot, and I'd want to sleep with one"? There are a million possible reasons that could have led you to believe that. When you examine the belief, you might determine you have good reasons for believing it. Yes, the first thing came to you because your parents said you should be, but then you realized you really love working with people and science and medicine. Or you might realize there are actually no good reasons to be a doctor, and you should be something else.

SPENCER: It seems to me that social influence works in this very subtle way where we're often not aware when we're socially influenced. It just feels like, "Oh, I want that thing, or I like that thing," and you don't realize, "Oh, no, I like it because other people like it. I want it because my friends want it."

RAFFI: Exactly. A belief is a belief. What I mean by that is it's very hard, unless you put in the conscious effort to be aware of where your beliefs came from and to know if they're a belief that was influenced by other people's expectations or a belief that came about through your own process that's true to you and your ultimate purpose. If you don't take the time to pick apart these beliefs, at least every once in a while, you're at risk of following, for example, just social influences.

SPENCER: I like to go back to values with regard to this kind of thing, where you think about what do I really, deeply, fundamentally value, and then make sure that your long-term goals are aligned with those values, so that you don't spend years and years pursuing this goal and then get to the end of it and be like, wait a minute, I don't actually care about this thing that much.

RAFFI: I read about your moral system based on intrinsic values, and I really like it. I think that a lot of these things can actually be complementary, and I'd encourage people who follow that system to do the same process with the values themselves. If you think that one of your intrinsic values is belief in God or not causing harm, or — I'm sorry if I'm butchering and I don't remember exactly what they are — but to really ask yourself, where did that intrinsic value come from? How intrinsic is it? Was it because my parents raised me that way? And if it is because my parents raised me that way, does it still feel true to me?

SPENCER: So I would distinguish between things that really are your intrinsic value, regardless of where they came from, whether it's through genetics or upbringing or culture, versus when you're living by other people's values. If, when you were three to 12 years old, certain ideas were impressed on you, and that ended up leading to a certain intrinsic value as an adult, I would respect that intrinsic value even though it came from your culture, because everything about us came from somewhere. It either came from our genetics or our culture or our upbringing. We didn't self-create our values. I just don't think that's the way values work. However, I would differentiate that from not really having that value, but your friends have that value, your parents have that value, and so you're trying to seek this thing that's not your value; it's someone else's value.

RAFFI: That's right. To your point about everything at some point came from culture or genetics or some combination of the two, that's probably true. But to me, the question is, have you examined it or not? It's much more likely that the belief is something you want to follow if you've taken the time to question it and figure out where it came from and ask these questions, versus if you don't, which you're at much more risk of drifting along.

SPENCER: A key aspect of career skills is negotiation. You're going to have to negotiate details of a job, your pay, all kinds of things. What are some tips you give around that?

RAFFI: Some people approach negotiation the wrong way because of how they've seen it done in movies, where one person says a high number, another person says a low number, and then they keep going back and forth. It's kind of this hard-charging contest of wills. There's an economist named Barry Nalebuff who says that a lot of people have a stereotype, and it's wrong. Usually, what negotiation is about is figuring out how you can expand the size of the pie. It's often less of a zero-sum game than people think. It's not that if I take a slice, you'll have less pie; it's more about what are the things we can add to the pie to make it mutually beneficial for both of us. I think the same thing is true if you're negotiating, for example, a raise from your boss. Unless you have some kind of adversarial relationship with your boss, which I know happens, let's assume it's not the case. Your boss often wants to support you; their life will be better if you're doing better work, and you'll do better work if you're more motivated. In an ideal world, if they could, they would pay you a million dollars to make you super happy so that you'll do the best possible work for them. But they can't pay a million dollars because they have to follow their own budget constraints or the wishes of their own boss. Then it becomes a more collaborative effort of, "How do we work together to come up with a compensation amount that motivates me enough and doesn't break your budget?" In practice, I recognize it's really hard to be that open about something like salaries or budgets, especially if you're very junior on a team; that might come across the wrong way. Instead, there are a series of tactics I recommend for how to approach the conversation that get at that underlying idea of expanding the size of the pie.

SPENCER: What are some of those tactics?

RAFFI: One of them is to start by telling your boss what your intention is. Similar to how I talked about approaching difficult conversations. If you come in and your boss has the impression you're young, inexperienced, feeling very entitled, and just want more money because your entire generation is lazy and wants more money, that's very different from coming in and saying, "I really like this work, and I want to do better work. Part of the way I can do better work is by having more money to outsource more things in my life. If I can order dinner more times in a week, then I'll be able to stay later in the office more times in a week." That line of thinking could be dangerous if you don't want to be working later and so forth. But the general principle I'm using the example to illustrate is if you show your boss, "I do care about this job. I want to work hard, and I want to be deserving of praise or promotion, let's talk about how I can get there." It establishes that shared intention, "We're on the same team; we're trying to figure out the best approach for compensation," rather than, "You're trying to squeeze more money out of me and I'm trying to squeeze less money out of you."

SPENCER: So taking a very non-adversarial approach.

RAFFI: Exactly. Another technique is to demonstrate that you've already started doing the work of the next level up. For example, if you have some mandate at your job, which is to write the marketing materials for three campaigns, and most people who are a senior associate handle three campaigns plus another client, you could say, "I've already started doing that. I have already started taking on another client, or something like that. I've demonstrated that I'm capable of doing that. So really, what you're doing by giving me this raise or this promotion is not giving me something new, it's just recognizing what I've already taken on." The best possible thing you can say in a negotiation or even as a line to put on your resume is saying, "I was tasked with doing X, and I accomplished X plus Y, and you typically pay people who do X plus Y more. So let's just formalize it and put that down."

SPENCER: When you think about negotiating with a boss, do you think about it as justifying that you deserve that amount? Or do you frame it fundamentally in a different way? Some people will come in and say, "Look, usually you pay people who do X plus Y this amount, I'm doing X plus Y, therefore I deserve to make this extra amount." I wonder, is that an effective framing from your point of view, framing it as I deserve this because I'm doing this thing?

RAFFI: I'd be very careful about using that word, because it could rub people the wrong way, especially given the current environment where a lot of, let's say older people think that younger people feel entitled. If you say, "I deserve this amount," it could really make it feel like it's coming from a place of entitlement, rather than a place of collaboration. As an aside, I think that word itself can be harmful if you let it immerse in your thinking too much. If you have this attitude of, "I deserve A, B, and C," you're more likely setting yourself up for disappointment in life. The hard truth is that basically nobody deserves anything just by virtue of being born. I would like to live in a world in which everyone is loved and taken care of and has everything they need, and that's great. I think people should strive to take care of each other, but in real life, just by virtue of being born, there's basically nothing that you deserve. If instead you say, "I'm going to go through life with this attitude of I want these things and I'm going to try to do what I can to get them," you're going to be a lot less disappointed if you don't get them than if you say, "I deserved it and I didn't get it," because that could lead you to think the world is unfair, or you don't have agency, or things like that.

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SPENCER: You mentioned a few minutes ago about this idea of looking for other elements in a negotiation that you can give to the other party. People often think of negotiation in terms of a single item being negotiated, like you're just negotiating pay, and you can either get paid more, in which case you win, or you can get paid less, in which case they win. But the reality is, often there are multiple elements in these negotiations. Maybe pay focuses on one variable, but let's say you're taking on a new job, you're about to get hired. There are a lot of different things to negotiate over. There's benefits, pay, vacation, and so on. One of the really interesting factors in negotiations is that you and the other party might care different amounts about these different factors, and that leads to a lot of opportunity.

RAFFI: Absolutely. Some of the factors you could put on the table are other forms of pay, like benefits, which are essentially being paid in another way, how much you do or don't have to travel depending on your preferences, or work remotely. Another big one is just how many growth opportunities you have. Unless you're in a very dire financial circumstance, it's probably best to think about your early career as how do I maximize the long-term earning potential that I have? Because of compound growth, it's going to pay off more in the long run to gain some growth opportunity than to just try to squeeze another thousand dollars for the year out of my boss. With that attitude, you can say, "I'm willing to take this lower salary you offer me, but what I really want to do is try to level up as quickly as possible. I request that you bring me to more senior meetings, or let me travel with you, or things like that." That would impress a prospective employer, and more importantly, might actually give you those opportunities. One of those other things you could put on the table is asking for more opportunities to learn and to grow faster.

SPENCER: Before we wrap up, I want to cover the fourth category you mentioned, which is mental skills. What's one of the big mental skills that you feel people really need to learn?

RAFFI: One of them is critical thinking. There's this saying that is sometimes called Sturgeon's Law, which is that, "90% of everything you hear or read is total BS." Anecdotally, for my own life, I feel like Sturgeon's Law has been true. People write and say a lot of stuff, and most of it is kind of made up or not really true. If you don't build yourself a mind that's critical and skeptical, you're at risk of just believing all kinds of things that will give you an incorrect worldview or set you up for failure in life. Cultivating a healthy amount of skepticism, in other words, becoming a critical thinker, can make you a lot happier in life. There's a process for assimilating new information that I try to go through. I first try to understand what something is saying. Is the message of this movie that I'm watching that I should do this kind of thing with my relationship, or that kind of thing? Once you understand what the message is, you say, "Oh, it was actually worming its way into my mind." Song lyrics do this a lot. You listen to a happy pop song a lot, and then you start to realize, "Oh, wait, the song is actually conveying disbelief or this value system." Once you understand it, then you can examine it and say, "Do I actually agree with this? Do I not agree with it? Why or why not?" For that reason, I tend to read nonfiction very slowly because I feel like every single sentence you read is making some claim about the world or the way people work. If you don't stop to think about it and say, "Do I agree? Do I disagree? Why or why not? How else would that change my views?" Then you're at risk of just unconsciously assimilating information, and you end up with a mind that's full of all kinds of clutter that was never examined and therefore is likely to be untrue.

SPENCER: I think about this in the way that people word articles. You imagine a wording, "the CEO told us that he had fired 100 employees," versus "the CEO admitted that he fired 100 employees," It's such a different vibe, just the slight wording difference of "told us" versus "admitted." Yet, journalists and writers are doing these kinds of things all the time, often subconsciously, but the word choice really influences what we take away from things.

RAFFI: Absolutely, I think it's so prevalent in the media. Sometimes the journalists have an agenda because they're trying to get people to like or dislike the CEO. Sometimes it's just unconscious on their part, but to your point, it still impacts how people interpret the message. I think this happens even more so in music and movies and just all the things that we do for entertainment. Movies and music have at their core the people who wrote the lyrics or the screenplays, and those people have certain values and beliefs about the world, and those are bleeding into the stories that they're telling. I think most people derive a lot of their ways of living from stories and from songs without really thinking about it. What you're at risk of doing is basically following a belief system that works for very successful writers in Hollywood or the entertainment industry and doesn't actually work for those people.

SPENCER: With regard to critical thinking, once you've figured out what the message is, what else do you do to think critically about the content?

RAFFI: The way I describe it is as a metaphor that your mind is like a Brita filter. You pour the water in, the information gets filtered through. You examine what's true, what you think is not true, and then it goes down into your jug of clean, pure water, is the filter is information. But if you take in information too quickly, if you've ever tried to pour water too fast at the top of the filter, it overflows to the top, something goes down the spout and mixes. So you're mixing unfiltered water into the filtered water, and then you end up with dirty water in your jug, meaning a bunch of views or beliefs or things that you don't even know if they're true or not because you've never examined them. The main thing that I try to do is limit my consumption of information so it's not happening too quickly. I read slowly, but I also try not to take in too much reading, too much listening, too many things in a day without enough thinking time to process it. My rough heuristic is that people, on average, probably spend 80% of their time consuming information and 20% thinking about it. To have a healthy and well-informed worldview, it should be the opposite. You should probably spend 20% of your time taking in information and 80% of your time processing it.

SPENCER: For news, I subscribe to Flipside, which is a newsletter that has one news story a day, and it summarizes a viewpoint from the left and from the right, and sometimes also gives a libertarian perspective. I feel like that's just the right amount of news. It takes me two minutes to read, and it's one story. Usually on a given day, there's not more than one story that's really worth learning about. I feel like that's a good way for me to limit the amount of intake.

RAFFI: I also like Flipside. My personal preference is that I actually think the correct amount of news stories that are helpful to consume any given day is closer to zero. I think history is a lot more interesting than news. People really care about, "Who is Trump going to pick to be his next cabinet Secretary of x, y, and z?" Looking back, I was really into this when Biden was elected, like "Who's he going to pick for this and this?" It was in the news, and I was eagerly anticipating the news because it felt interesting. But a few years later, I don't even remember who that person is, even though they're currently in office, and it's probably even more important than when they were first picked. I think people get into this cycle, a hype cycle, basically, for the news. This is exciting, it's interesting just because it's on all the time or because people are talking about it all the time, but it's not intrinsically interesting or even practical to your life. I think there are so many interesting things we can learn from history because history is so long, and you could just take the most interesting parts. I've kind of always hoped that someone would start a newsletter where, instead of every day, it's like, "Here's what's happening today in the news." It's like, I just picked this really interesting day in history, and I'm going to tell you about what happened on that day.

SPENCER: Do you think we can learn more from history than we learn from the news happening now?

RAFFI: Absolutely. I think one of those reasons is, as I mentioned, there's just more history. So you could pick apart the interesting days. Probably 364 days of the year weren't that important, or they weren't important in some place in the globe, and you could pick a different place if there's something to really learn. But I also think another reason is just the adage that comes from Ecclesiastes: there's nothing new under the sun. History tends to repeat itself. Human behavior repeats itself. I don't think that human psychology has fundamentally changed over the past few thousand years, even though the world has changed a lot. And so if you want to understand people, I think you can learn as much, if not even more, from seeing how people, over long periods of time, have reacted to changes in the world, rather than what's happening today in the news.

SPENCER: Another mental skill that I know you teach about is facing rejection. Tell us about that. Why is that important?

RAFFI: There was one semester in college that I called my winter of rejection, where I felt like I was being rejected from everything. I was in some political student group, and I ran for president, and I lost the election. Then they let you drop down, so I dropped down to vice president, I lost that election, then I dropped down to treasurer and I lost. So I lost every position. I was really into theater, and I auditioned for two plays. I didn't even get cast in both plays, not even a bit role. I applied to the theater to direct a play for the next year, and I got rejected from that. There was a girl that I had a crush on, and we actually got to know each other pretty well, and I finally had the courage to ask her out, and she rejected me. At the end of this whole semester of rejection, I took a one-week break during our vacation. I was in the mountains hiking with a friend, and I was just thinking, one way to approach these rejections is that they're actually giving me a superpower, and that superpower is not being afraid of rejection. Because if you're not afraid of being rejected, you'd be willing to try basically anything. I think fear of rejection holds people back from pursuing an opportunity, like a new job or asking someone on a date, because you know the rejection is going to hurt. But if you kind of inoculate yourself, if you get hurt or stung enough times by rejection, that doesn't hurt as much anymore, then you'd be willing to try all kinds of things. I went back to campus with that new attitude of, I'm going to treasure these rejections because they're inoculating me against the future. The girl that I ended up asking out and getting rejected by later, I asked her out again, and she said yes, and we are now married. That's Charlotte. Shortly after we got married and we were starting our careers, we created a rejection treasure chest at home. We said, every time we get rejected from an opportunity, we're going to print out the letter and put it in our treasure chest so we can treasure them instead of fearing them.

SPENCER: That's just a nice reframe. It's so interesting how bad rejection feels, even when it doesn't have very severe consequences for us. People are so afraid to be rejected, they won't ask out the attractive person they've been talking to for the last hour, and then they never see the person again. It's just because they were afraid of being rejected. But the reality is, if they were rejected, probably a few weeks later, they wouldn't even think about it anymore.

RAFFI: Absolutely, one of the salves that I think can help in the moment to alleviate that pain of being rejected is to remember that one of the reasons rejection hurts is it feels like someone else has evaluated you as a person and determined you're not good enough. So you apply for a job. You're like, "They saw my resume. I even interviewed with them. They got to know me, whatever, and they determined I'm not good enough." That hurts, but it hurts a little bit less if you realize they actually don't know you that well; they didn't get to know you that much. Maybe if they'd gotten to see a more complete picture of you, they would have realized that you would have been amazing for that job. Same thing with asking someone out on a date. Maybe this person doesn't know you well enough. If they knew you well enough, they would think you're amazing and definitely want to date you. At the moment, we tend to have this feeling of like my entire personhood has been deemed not worthy, instead of the reality, which is this one small aspect of my personhood that I had a very small and limited window to show got rejected.

SPENCER: It's interesting because we have so much evidence about ourselves that any kind of additional evidence like that, being rejected by a person or not getting a job, surely that couldn't rationally tell us that much about ourselves.

RAFFI: In some cases, I think it can. It can be edifying. Sometimes if someone really gets to know you and determines something is not right for you, that can teach you something about yourself. But I think that lesson very rarely gets integrated because the pain of the rejection is so great. I aspire to this level of zenness, where you'd say, "Rejections just don't hurt me at all. Not only can I not feel stung by them, but I can also see some of the truth in them and try to learn from that small grain of truth."

SPENCER: Right. I guess there's a big difference between you applying for a job and 100 other people applying and you getting rejected. Clearly, it means very little that you're rejected, or you meet someone for an hour and they don't want to go on a date. Clearly, it doesn't mean very much. Versus someone gets to know you deeply and then you date them for two years, and then they leave you because they're unhappy. That is a real learning lesson. That's a different sort of rejection.

RAFFI: Another way of putting it might be, a lot of people live their lives in a way where they're trying to impress people who don't care about them. I think it's better to live your life in a way where you're trying to impress the people who do care about you. If you get some kind of fancy job or are dating someone who is conventionally desirable, then some random person you don't know or someone in your peer group might say, "Oh, you're impressive," but those people don't actually care about you; they don't have your best interests at heart. The people who do care about you do. If you think, "I want the people who care about me and who know me best and actually know what's best for me more than some stranger," to impress them, those tend to mean things that are more like, as David Brooks puts it, the eulogy values rather than the resume values. People who know you best and who care about you the most tend to be impressed when you do something kind or show up for someone in a friendship or relationship.

SPENCER: It seems that social media really impresses on us this urge to impress the people that don't care about you. It's sort of the whole point, in a way. It's trying to get you to post for other people that are not in your close circle.

RAFFI: Exactly. That's probably exacerbating the problem. I think social media has made it a lot worse, but it probably existed for almost all of human civilization for a variety of reasons. If you subscribe to evolutionary psychology, there might be reasons it was an evolutionary advantage to be impressive to people in your group, even if they don't care about you that much, because it might mean that you can survive in some other ways. But I think a lot of those reasons are obsolete now, and so social media preys on that fundamental psychology in ways that can make it really unhealthy. If you can step back and just say, "None of these people online actually know about me; even worse, they don't even care about me, and so they might be encouraging me to do something that's bad for myself." I think the best, most obvious example is some kind of stupid stunt or prank. You could get a lot of likes or a lot of views for that kind of thing, but the people watching it don't care if you are actually hurt or not. It's kind of an inane example. I know not a ton of people do public pranks like that, but I think it demonstrates this principle that if you're going for people's attention or what might impress them for a short period of time, you're not actually doing what's going to impress them over a lifetime, which tends to be more of those values of kindness and so forth.

SPENCER: There's a wonderful essay by C.S. Lewis called it "The Inner Ring." I don't know if you happen to be familiar with it. It's about how many people spend their lives trying to get into the inner ring, which is sort of whoever they think of as being cool. They want to be accepted by that group. And then, of course, when they get in the inner ring, they discover often there's an inner ring inside the inner ring that they're still outside of. And it's sort of this endless chase about how unfulfilling that really is. So it's a lovely essay for those interested in this.

RAFFI: I would say my own experience validates that. Through my work, I work with a lot of very successful people. I run a community for CEOs and political leaders and things like that. In itself, it is extremely exclusive. But sometimes even the people in these communities feel like there are even more exclusive communities. In order to get into those, they need to make more money or aspire to a higher height in their career or something like that. So, if you're constantly trying to fulfill yourself by what's coming next on this path, you're basically never going to be happy. I think it's the general principle that it boils down to. There's a really wonderful summary of Proust's novels that was written by the guy who runs The School of Life. It's on the website, and in the summary, he's describing one of the stories in Proust's novels. Basically, what you said is he's trying to get into these more and more elite social circles. What he realized at the end is it was driven by this belief that if you get to the innermost circle, the people there will finally be the people you want to spend your time with because they're more interesting or better friends or something better to be around than all those other people. What he realized at the end is the rate of people who are good to be friends with is just totally evenly distributed across all these circles. It makes no difference if they're in the innermost circle or the outermost circle; the qualities you want in a friend, like how kind and interesting they are, are actually not correlated with that at all and probably, in some cases, are even reverse correlated.

SPENCER: Certainly, these kinds of inner circles often attract people who are desperate to be in inner circles, and that's their number one priority in life, and that often does not make for a good friendship.

RAFFI: Going back to that concept of striving for the next thing, it's actually something I try to mention right after I talk about rejection because rejection is when you're trying to get something for your life. You're trying to get a new job or title or something like that. But actually, I think what is a bigger problem for most people is not what to do when you get rejected, but what to do when you get accepted. For a lot of people, achieving something presents an even worse problem than not getting it because now you have it. But are you happy? If your entire wiring is in this achievement mindset of "I will be happy when I get the next thing," you will never be happy because once you have that thing, then you're going to want to get the next thing. The metaphor I use is you're climbing a mountain. You're trying to reach the summit, but whenever you reach a summit, you just see that there's another mountain with an even taller summit, and you need to climb that one. If you never stop to enjoy the view and look down at how far you've come and celebrate your achievement, then you're never going to be happy.

SPENCER: Raffi, I know that you have a book coming out. You want to take a moment to tell us about that.

RAFFI: It's called How to Be a Grown-Up. This is based on the course that I taught at Boston College about adulting, and that course itself was born out of my experience working with young people as a career coach and my own experience in the workplace, just realizing that I'd gone to a good college and had a good job and so forth, but I still didn't know all these fundamental things that could set me up for a better life and a better adulthood. That includes all the topics we mentioned, like personal finance, careers, happiness, and relationships. What I tried to do over many years is condense that information into a 14-week course, and now the 14-week course is essentially a 14-chapter book that anyone can read, and hopefully more people than just those students can benefit from that knowledge.

SPENCER: And we'll be sure to put a link in the show notes for anyone interested in checking out his book. Raffi, any final thought you want to leave the listener with before we wrap up?

RAFFI: I guess my final thought is, knowledge can only get you so far. My personal mission here is to try to equip people with more knowledge, at the very least, knowledge that I wish I had when I was younger. But unless you put that knowledge into practice, it's basically not going to do anything for you. I think the hardest thing about putting knowledge into practice is that we live most of our lives on autopilot. We're basically acting every day according to the patterns and the rhythms that have been worn into the grooves of our brain. Unless you break out of autopilot, you can't really change the way that you act. I encourage everyone who's trying to learn new things and wants to put them into practice to say, "How can I actually start doing this thing today?" and keep track of whether you're doing it today. That opens up a whole other can of worms on this topic of habit formation, which I think, Spencer, you're an expert on. I would encourage everyone to read your stuff about it, but basically to recognize that in order to break out of that autopilot, you have to decide that you want to live your life on purpose, not according to these expectations that have been ingrained in you, not according to these unconscious patterns that you just keep repeating every single day, but basically saying, "I'm at the stage in life where I'm deciding for myself what I want. I'm using knowledge to figure out how to get there, and I'm going to do all that with a sense of intention."

SPENCER: Fantastic. Well, thanks for coming on.

RAFFI: Thank you, Spencer, this was really fun.

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