Case Kenny: Stop “Settling Down” and Start “Settling Up”

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1:13Steven, Brandon, and Bruno, the business owners of SandCloud, reinvested their 2 % cash back to help build the company's retail presence. Capital One, What's in your wallet? Find out more at CapitalOne.com slash Spark Cash Plus Terms Apply. Today on the James Altucher Show. I think the right relationship should make you more independent. A total reversal of how I used to think of a relationship. And I reference a little bit of research in that as well. I kind of refuse myself to be like, wow, this is like, I want to lock this woman down and get the government involved in it and marry her deep down.

1:52I was like, I don't know if I'm a relationship guy. We are adopting expectations. That is assumptions about how fast the relationship should go. And it's really not true to us. And there's no right way and there's no right pace of a relationship. And, you know, a lot of people nowadays talk a lot about for women, it's the right person. And for men, it's the right time. My whole mindset is that when you're dating, don't date to be liked, date to be seen.

2:20This isn't your average business podcast, and he's not your average host. This is the James Altucher Show.

2:37I've got Case Kenney with me, the author of the new book, The Opposite of Settling, and also the host of the podcast, New Mindset, Who Dis? Case, welcome to the show. Thank you. Thank you for having me, James. Appreciate it. Now, Case, I've been in the dating world. I've been in the married world probably more times than I would like to admit for both. And the opposite of settling, maybe I want to hear you describe what you mean by settling, but also I want to hear your story. I want to hear like when you felt you might have settled and then started to work on the ideas that became so poignant in your book.

3:18For sure. Well, yeah, I mean, I think, you know, I wrote the book because a couple years ago, I sat down and I was thinking about like some of my younger self resistance to commitment and relationships, right? So like classic 20, mid 20 something guy, avoidant mentality. And I was thinking back about like why maybe I was that way and younger men are that way as well. But I'm sorry to interrupt, but can I ask what way were you? What does it mean? Like, give me, what was a specific example? Not bought into the concept of a relationship, right? So like not seeing... So like you would be dating someone and what would happen?

3:52And then, you know, classic male avoidant of letting it die because you didn't see the purpose of a long-term commitment and marriage and, you know, and that in its totality. I didn't see the point of a relationship because it was always couched in the context of the phrasing. And I almost called the book this, but the phrasing was settle down, right when are you going to settle down when i maybe i want to settle down but i don't know i always thought it was curious phrasing right this idea it's got the word settle in it for one it also has the word down in it for two and i always just thought that that was curious because my whole world and mindfulness is that of emotional vocabulary and language and how we speak about ourselves in life and i was like man maybe it had a little bit to do with that that my anticipation of a relationship was this lessening was this well you're going to lose your independence you're going to lose some of your spark and some of your passion and your ability to be spontaneous and it's down.

4:51And I was like, maybe that's why when I was younger, I didn't have a great sales pitch for what love and a committed relationship had to offer. So I wrote it through that lens. And now I'm 37 now and I have found my person and even chapter two of the book, I believe, is about how I think the right relationship should make you more independent, a total reversal of how I used to think of a relationship. And I reference a little bit of research in that as well. But yeah, that is kind of my evolution. And it started, but it started with that phrasing. Was there like someone who you were dating who in retrospect, you think maybe you could have had more of a relationship with, but you were so avoidant that you pushed that person away?

5:38Like what's a, what's a time when you actually, what did you do that ended a relationship that maybe, and what were the qualities of that person and, and so on? Like, give me a real example. Yeah. I mean, that's a doozy of a question, right? And in hindsight, probably the answer is probably yes. Like I probably could have made a certain relationship work better and go to the next level. I mean, what was it, what was it about that person? Like that makes you think that now? Uh, what was the, what was the situation? I mean, I can think back to like someone I dated in my 20s, you know, attractive, all the qualities that I was looking for, I suppose, you know, ambitious, funny, easy to get along with.

6:16I think, you know, at the time, you know, I did because I wasn't so bought into it. I just kind of didn't pursue the next step. I kind of refused myself to be like, wow, this is like I want to like lock this woman down and, you know, get the government involved and marry her. I think that was my mentality. So unfortunately, it was like that passive letting go. Like what? Like you didn't respond to some messages or you're not ready to settle down? I mean, I think to be honest, it was like, yeah, I mean, I probably should have pushed like, I want to meet your family and I want you to meet my family.

6:52And I didn't do those things because I knew, you know, I deep down was like, I don't know if I'm a relationship guy. So like it was the obvious things that you would do, right? You get to know their family, you do vacations, you talk about the future. I think that was like something you look back in retrospect and I kind of cringe a little bit at not being the guy to talk about the future and, you know, noncommittal in the little ways as well as the larger ways. And then, of course, yeah, just being kind of passive and letting that go. So I look back at that younger version of myself and like, man, that is, you know, a little embarrassing and immature to let a relationship die in that sense instead of either communicating about it.

7:33But, you know, I'm so luckily lucky now to, of course, have found my person. And, you know, I dedicated this book to her and then to, you know, be able to have this Emily. Emily. How did you meet her? I met her in Chicago right before we moved to Miami. We started dating in Chicago and then we dated for about a year. And then we road trips down to Miami together and then moved in and I've been down there for about three years. How did you guys meet? We met on a dating app. So very modern, modern age love story. And then when you met her, was it like, oh, I like this person more than anybody I ever dated before?

8:10Actually, I would say it was a pretty slow burn, which I talk a lot in the book about the way that a lot of the times we are adopting expectations, that is assumptions about how fast a relationship should go. And it's really not true to us. And there's no right way and there's no right pace of a relationship. for us I think I'm really glad that it was a slow burn and that it allowed for us of course to get to know each other but I think it also opened my perspective as far as oh well you know this is an amazing woman and we we have all the compatibility and we have the creative compatibility and the ambition compatibility and the humor compatibility you know on all the different ways that I look at a relationship but I think doing it slowly over time was like wow you know I could let this person in more and more.

8:53And this isn't a threat to my identity. This isn't a threat to what I want to get out of life. Um, you know, very much so felt through her. I felt encouraged to be more independent, um, both like literally like, Hey, so you should do this thing and that thing, but like on a, on a soulful level, maintaining of that, of that, uh, you know, kind of identity. I think the slowness there was, was really helpful. And then, um, and then we moved down to Miami and moved in together. And then you learn a whole lot about a person by, you know, living with them. And I think with her, it was, it was, it was special.

9:27And, you know, a lot of people nowadays talk a lot about how for men, it's, it's, it's all about timing, right? For women, for women, it's the right person. And for men, it's the right time. I don't know if you've heard that before. And it's, it's, it's, what was it, in Sex and the City or something, the cab, the taxi light theory or something that when a man puts the cab light on that he's looking for someone, you know, the next person who comes along, that's the person. I don't think that's necessarily true to me because that kind of cheapens the compatibility. But I think timing is important.

9:59I think also at the same stage have really thrown myself into my work for years and years and years and really consider myself to be much more mindful and self-aware and emotionally self-sufficient along the way. And I think all those things combined just led to that, oh, you know this is not the sales pitch i thought of a relationship this is and i call it in the book settling up that is with her getting more out of life being more ambitious together having this you know i refer to them in the books through the gotman institute of bids for connection the way that we connect with each other on a level that i don't think i had in the past and just seeing it as this energizing uplifting thing in my life versus this expectation that it would pull me down.

10:42So just like a big mindset shift. Yeah. Like given that you work so hard and you're, and you're, you know, obviously you're very successful on social media and as a writer and so on, did you think that this was going to, um, distract you from, from your work or, or, or give you fewer things to say about relationships? Cause now you're going to be in like one relationship. Yeah, certainly. I mean, cause I wrote a book in 2020 called single is your superpower, which I would say is, you know, still very true. And I evangelize very much so for figuring out yourself and your life and your spark through your single years.

11:16But yeah, I think I identified very much through that and, you know, really came into myself as a single dude. But yeah, I think certainly that was a fear. And then, you know, on the ambition side, like I want to, I want to be a prolific author and entrepreneur and doing all these things and to travel. And it was just a bad assumption, frankly, I think. That's why I wrote the book. And that's why I wrote about flipping the framing of what is the sales pitch for love that doesn't include settling, doesn't include settling down. So I'm glad I was patient in the pursuit of that. And now I can truly say that, you know, I practice what I preach.

11:53And, you know, I'm lucky to have found this person. You know, you mentioned in the book that there's some research that suggests that men in general perceive themselves as not as likable as they are. I forgot the exact phrasing you use, but that they walk into a room and they think basically everyone hates them when actually that's not true. Yeah, yeah, yeah. That's an extreme version of it. But that does make someone feel like, oh, I better lock this down because if everyone doesn't like me and this person seems to like me, I better lock it down before they realize the truth. Yeah, right. I mean, you think about it.

12:30So it's called the liking gap. And it was men and women alike, but it was basically just the overarching statistical research that says that we tend to underestimate how much people like us after we have a conversation. and in turn the liking gap it causes us to do all kinds of behaviors one namely having a scarcity mindset that if oh someone finally likes us then we need to jump on board or two that it leads us to self-censor to be overly critical of ourselves when in fact the reality is people are more receptive to us than we assume and you know a lot of this is rather logical and that the reason that we maybe think that people don't like us is because we're in performance mode and we're judging ourselves versus being present in the conversation.

13:20And they also, they also, the researchers suggested that the reason that we, you know, we, we don't, we don't take time after a conversation to like get feedback, which would be a little strange, right? For me to be like, how do you think our conversation just went like a post conversation survey? But it's like a combination of those things that really just lead us in this unfair self judgment loop. So I like that as context for the fact that overwhelmingly so, you know, statistically, you are more likable than you think. So take a deep breath. Perhaps we don't need this scarcity, chase, chase, chase mindset.

13:54And I like just a little wind in your proverbial sail. I mean, I think this is extremely valuable advice because if you go into every situation thinking you're not going to be as likable as you are, you're going to go into sales mode. Like you said, you're going to be in performance mode where, oh, what can I do to get this person to like me? As opposed to, and you mentioned this in another part of the book, as opposed to sitting there saying, how does this, actually wondering for yourself, how does this person make me feel? Do I feel good? Do I feel bad? Like actually being present to determine if this is a good situation for you or not, you get stuck in this performance mode and where victory is the girl or guy likes you.

14:34and failure, as you point out, is ending or they don't like you. When that might not be value at all, that might be a success. You just have to, it's like you say, you have to have a new mindset for dealing with this. Like just being aware of that one thing, I think would have helped me a lot when I was younger. Yeah, me too. I mean, my whole mindset is, the mindset is that when you're dating, don't date to be liked, date to be seen. And that's a bit of a self-help-ism, right? But like the whole idea is, yes, of course you want to be liked. who wouldn't want to be liked but having that be your motivation is very distracting for one especially if you don't think you're likable then everything we just referenced but for two people can trick you into thinking that they like you and they get to say the right things date to be seen is the whole thesis of the idea which is the opposite of settling is you date someone who amplifies who you are they make you more of yourself which if you talk to people nowadays especially women women lose themselves in relationships men deceive others in relationships relationships, just on the hyperbole spectrum there.

15:37So just to be able to be comfortable in who you are and to use that as the lens for whether someone is compatible or not. I also talk in the book about the research that also supports that non-conforming traits are overwhelmingly attractive. That is the thing that we think makes us unlikable or too loud or too quiet or too intense or too whatever. That is the thing that draws people to us. And of course, it might repel the wrong people, but it will bring in the right people. People, according to the research, likely are drawn to non-conforming traits. So you put that together with you're more likable than you think you are.

16:14Maybe it gives you a firmer foundation off of which to launch and say, I'm dating to be seen. I would like to be liked, but it's part of the process to not be liked because I'm dating to be seen. Well, can you tell me like, what's a specific example or a story of a non-conforming trait? Like what were your non-conforming traits when you met Emily and what were hers? I mean, I think, I don't know. I mean, I share my feelings for a living. It's a somewhat non-traditional career path. It doesn't have the greatest financial security. So it's a little out there creatively as far as what I do, especially in a world where men very much identify by what they do.

16:50And I worked in advertising technology sales for 12 years before doing this. So it was a big switch. It was like throwing that away. So I'd say that. I think a younger me was like very introverted as well. So like nonconforming go both ways, right? It's like you're too loud or you're too quiet or you're too this or you're too that or you're too traditional or too non-traditional, whatever it may be. So I think, yeah, for me, probably those two certainly at least gave me a little bit of insecurity sometimes. And now, of course, you know, I'm proud of what I do. And I joke that I share my feelings for a living.

17:24Like I've stepped into the description.

17:30Take a quick break. If you like this episode, I'd really, really appreciate it. It means so much to me. Please share it with your friends and subscribe to the podcast. Email me at alcatra at gmail.com and tell me why you subscribed. Thanks.

17:51Being an entrepreneur is a 24-7 job. And when you're hiring, you need a partner that works as hard as you do. That hiring partner is LinkedIn Jobs. When you clock out, LinkedIn clocks in. LinkedIn makes it easy to post your job for free, share with your network, get qualified candidates that you can manage all in one place. For one thing, you can post a job. LinkedIn's new feature can help you write job descriptions and then quickly get your job in front of the right people. You get qualified candidates. At the end of the day, the most important thing to your business is the quality of the candidates.

18:22And with LinkedIn, of course, you can feel confident that you're getting the best. Based on LinkedIn data, 72 % of small and medium businesses say using LinkedIn helps them find high-quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn. Post your job for free at linkedin.com slash altature. That's linkedin.com slash altature to post your job for free. Terms and conditions apply. When you say you were introverted, like, what does that mean? I mean pretty and there's nothing wrong with being introverted to be clear yeah um I think uh yeah it was I would it's funny I would say to answer your question I would say I would rather listen than speak in the past and now I can't stop yapping I love to talk I love to express my opinion and uh I owe that to a couple things I think most mostly just coming into myself and understanding my creative purpose in life but then also I think I worked in sales for a while for a long time to my point and I think it really helped me step into confidence and so I always recommend you know everyone try to do sales at some point wait tables at some point it teaches you a lot about yourself I think I just needed those contexts to really pull it out of me and that I mean that was the whole reason I started the podcast because in 2018 I was doing really well in my career but I didn't feel like I knew myself that well like I feel like I knew what to do in my career I knew how to like I promoted a regional vice president and that's fantastic but I didn't know I didn't have a worldview.

19:52I didn't have a sense of self. I didn't have a sense as a partner, as a brother, as a son. And I wanted that. And that's why I sat down and started. How did you know that? I think that's a hard thing to know about yourself. Well, it was somewhat simple for me, I suppose, because somewhat introverted, but very type A. And I just felt like I would go to work and I felt so clear. Like, oh, this is the thing. This is what I say. And I just had the blueprint. but then the second I left the work, I was just like a shell of a man. And I don't know the best way to describe it, but it just felt like I would have clarity and then no clarity.

20:29And I would have confidence and then no confidence. And of course, it's great to have your job put a little wind in your sail, but I didn't like that fact that I felt like I was one person here and another person there. A mask here, no mask there. I just didn't like that fact. And I was like, I want to be the same person all the time. And that was kind of the motivation for the podcast. But maybe after work, you were just like tired. And so like you were talking all day, you were selling all day and then you just needed a break from that at 6 p.m., 7 p.m. whenever you got off work. No, it was more just like anytime like I had to formulate an opinion on what is right in life or what do I think about a political event or something?

21:07I just, I would look around at other people's examples. And I think that was just like, well, that's crazy because at work, people come to me. I'm the guy who sets the tone and the leader and we do the things. And I just didn't like that fact that everywhere else I was looking around for other people's examples. I was doing a lot of borrowing and just overall rushing. And yeah, when I was like single, I was like, oh, this is what a single guy does. You need to go out and buy bottle service and do this and have a roster. And at a certain point, I was like, well, this just doesn't seem like it's coming from me.

21:39And I was frustrated by that fact. And voila, podcast. So you felt like maybe you were like what on a date would you basically say what you thought the other person wanted to hear versus you saying what you really felt uh why i wouldn't consider possibly probably a little bit of that just to you know try to create the best date possible um but it was more just like of not having an intention which is like the worst thing like when women are dating men who men who don't know what they want right and men who date women who don't know what they want i think it was more of that mentality. Like if you really try to crack the egg open, it would be more a matter of, yeah, case like, what are you looking for?

22:21And I would say, I'm looking just to, for someone great and to see where things go. You know, nothing like manipulative or like having game. I definitely did not have game. So more of just, I think you probably had a little more game than you admit, but I'll, I appreciate that. I don't know. I don't think so. But nowadays I've got more of a way with words than I did in the past. But yeah, it's just that, that feeling of not knowing myself. And that translating into other areas of life that frustrated me. And I think it led me here, which I'm grateful for. And, you know, you talk about this thing, which when you're in a relationship, you talk about this thing called peak end rule, where, you know, it seems like it's the worst case scenario for something to end.

23:03And you can't even get it out of your head that, no, this might be the right thing for me. Because you think you've somehow convinced yourself, this is the best situation I've ever had. There's no one going to be like this. Plus, everybody hates being rejected. So you really fight hard for a relationship not to end in general. I'm not saying this about you or me or just in general. And how do you avoid that? How do you say, hey, this is not working out for me. I shouldn't try anymore. Because a lot of people say, oh, there's going to be ups and downs in everything. How do you know when the downs are too much?

23:34Well, for sure. I mean, in reference to the peak end rule, I think, again, it's helpful observations to have with us, right? Similarly to you're more likable than you think you are. the peak end rule would say, hey, for the most part, your memories are distorting your current clarity. The peak end rule says that we remember experiences by their emotional peaks and their endings. And such so, we tend to choose the one that kind of hurts us more. Like, we'll remember the middle, which was amazing, and it's this emotional peak. But then we had lost that, and we're like, oh my gosh, I lost everything.

24:11I'm incapable of finding that again, and we beat ourselves up. Or we remember the end where maybe it was this dumpster fire of a relationship ending and we're like, oh my gosh, like I can't imagine of her dating again. That was so bad. Either way, in a negative sense, the peak end rule leads to all these limiting beliefs in the present. I think, and I talk a little bit about in the book, but it's like the idea in life and blanking on the philosopher who said it, he says that cheerfulness is the ultimate sign of wisdom in that to be successful in any area of life, as I'm sure you'd agree, there has to be some mentality of being able to appreciate good memories in the past without throwing them all away because it didn't lead to exactly what you wanted, right?

24:54So to be able to appreciate the second date that was amazing and you have a good memory, even if the relationship ended, to not do what so many people do nowadays, which is just throw out the complete chapter because it didn't end in a marriage, for instance. I think if you want to have a more optimistic mindset around dating which is the whole point of the book and my ethos is The ability to still appreciate a good memory with a temporary person and to not do what We tend to do which is to villainize that person Villainize that chapter to be able to say I appreciate that emotional peak even though the ending was bad I still appreciate it or to be able to look at the end and say yes That ended in a poor way but I can still appreciate the concept of what happened in the relationship without burning it all to the ground.