[00:00:00] Dylan Bain: Hello, and welcome to Intuitive Finance. I am so excited to bring you another one of our interviews. This time is with an internationally acclaimed relationship coach whose work has reached more than 250 million people worldwide since 2009.

[00:00:16] My guest today is Mr. Jordan Gray. He runs a relationship coaching practice that has fundamentally changed how I think about relationships. With his mission to empower people to have the healthiest and most nourishing relationships possible, I found a new way in which I think about relationships both with myself and with other people. Our conversation today covers a lot of different topics, and I cannot wait for you guys to be able to enjoy it and be able to get a lot of value out of it.

[00:00:44] So without further ado, my interview with Mr. Jordan Gray.

[00:00:47] Intro: We’re saying goodbye to the rigid numbers and strict budgets, and putting relationships back at the heart of personal finance. This is more than a podcast, it’s an invitation to reimagine your money story and journey with us through a landscape of intuitive strategies and abundance. Join a community that nurtures transformative financial mindsets.

[00:01:12] Welcome to Intuitive Finance. I’m your host, Dylan Bain.

[00:01:23] Dylan Bain: Ladies and gentlemen, I am super excited for my guest today. His name is Jordan Gray. He is a relationship coach and a money coach, and somebody that I am just itching to have a conversation with.

[00:01:35] Jordan, thank you so much for being on the podcast.

[00:01:37] Jordan Gray: Thanks for having me, Dylan. Excited to be here.

[00:01:39] Dylan Bain: Oh my God. As you know, this is episode 100. And so like, I saved this one special for you. I just want you to know that.

[00:01:47] Jordan Gray: I really love round numbers. So I feel deeply honored that I get this spot.

[00:01:53] Dylan Bain: Fantastic. Well, let’s just start off with, can you tell me how you got your start in relationship coaching and, where did you start and where are you now?

[00:02:04] Jordan Gray: Sure. I knew that I wanted to do this work from a very young age — like a freakishly young age. When I was seven years old, I was asking my parents what university degrees there were that helped you be a therapist for only talking about marriage? You know, I was in like second grade, third grade when I was having these conversations.

[00:02:22] I started it as an actual full time job at 21. I basically did a Google search for my hometown of local companies that did something that was as close to what I wanted to do as possible. I found a company, basically pushed my way in, created a job for myself by working for free for the first few months. Worked with them for about four years, and then jumped ship when they were pivoting in a different direction than I wanted to go. Started my own business at 24, 25. And yeah, this business is now coming up on 11 years old and has reached over a quarter billion people across the world.

[00:03:02] Dylan Bain: Wow. So starting off, just kind of bullying your way in, then up to a quarter of a billion people that have been touched by your work. So if someone was to ask you like, put a pin on what it is that you do specifically with relationship coaching, what would you say?

[00:03:19] Jordan Gray: I don’t have a top of mind one liner, but the most honest spitballed response I can think of right now is I help intentional, proactive people have even better relationships, especially intimate relationships. Yeah, I once had one of my clients, one of my favorite multi-year clients. He was like, you don’t help relationally morbid obese, lose 10 pounds. You help marathon — marathon runners shave seconds off of their time.

[00:03:50] And that tends to be — a lot of my clients are often kind of semi-facetiously joke that they have like, superhero syndrome. That they like really want to be 10/10 in every life pillar simultaneously, which is a blessing and a curse because you can make a lot happen with that mindset, and it can also, you know, trap you because it’s a lot of pressure. Most of my relationship clients tend to just be like, a couple steps more neurotic versions of me. Because I’m also — I have a lot of overlap with them, which is why they tend to resonate with my style of work.

[00:04:24] Dylan Bain: Amazing. So tell me more about that neuroticism and like, what it is that, you know — shaving seconds off a marathon, like that you’re already talking about the elite at this point. What does that even look like in the realm of relationships? You know, and like specifically, what is it that they’re doing in the beginning that you’re coaching them to move away from or towards something else?

[00:04:45] Jordan Gray: Yeah. I mean, it’s very common in the initial kind of intake form or application form for one on one clients, especially that they’re like, my wife and I are great. Or my husband and I are great. We’re like, we’re really good as a couple. We’re the envy of our peer group. She isn’t complaining. He isn’t complaining. Like, things are smooth. And I know that fill in the blank, X could be better one out of 20 times. I lose my erection when we’re being sexual and it messes with me. How do I nuke the possibility of that happening?

[00:05:17] Or our three kids, you know — we’re empty nesters. Our three kids just left the house. You know, our relationship has been fine and stable and like, very functional. And with this new vacuum of, oh, it’s just us again and our youngest is off to university. Okay. Let’s like — what’s the smoothest way we hit the ground running as an empty nester couple again? You know, things like that. They’re like, they’re not two seconds away from divorce. They’re like, I don’t need a coach and I’d like this little thing to be tweaked. And yeah, I’ve always enjoyed those small tweak clients more. ‘Cause it just, it’s a bigger challenge to like have someone be like 92% of the suggestions they make, they’re like, yeah no, that’s good. That’s good. Oh that. Okay, yeah. There’s something I get juice out of that, like micro-nuance of pointing out a subtle blind spot that a highly self-aware person hasn’t been able to get on the pulse of through months of journaling or talk-based therapy, whatever.

[00:06:24] Dylan Bain: Well, so it sounds like when you’re talking about that, like it’s — they’ve got that one thing, but they’re so dialed in and so many other places, they can’t see it. Am I on base there?

[00:06:34] Jordan Gray: Totally. I mean, I think that’s something that I would just extrapolate to all of humanity. You know, one of my favorite expressions is you can’t read the label from inside the jar. I think that everyone needs, whether it’s an intimate partner or a coach or a therapist or men’s group or whatever the case may be like, we all need reflections. We all have some 1%, you know, shadow or blind spot. So they are as close to themselves as anyone else is, and so they also need external reflection from people that don’t live inside their heads.

[00:07:04] Dylan Bain: I am totally stealing that you can’t read the label from inside the jar. I hope that you don’t have a trademark because I’m taking it. Because I get clients that come in to the financial side of things and they’re like, well, I feel we got spreadsheets. Like we’re doing just fine. I don’t know why we would need a coach. And my whole point to them is like, what is it that you don’t want to look at? What is the thing that you’re missing? That keeps you up at night or is in the back of your head? What is the thing that if we were having a cocktail party and we’re like, hey, let’s pull out your books and take a look, that you’re not going to want people to see? Because that is the place where I can help you.

[00:07:37] Jordan Gray: Totally. Yeah, it’s the exact same place with the relationship. It’s like, there’s something that either, there’s the most shame, fear, resistance, embarrassment around, or there’s a mountain of reaction formation of, okay, I know that this thing’s there. And so to not be with this, to not feel this, I’m going to build up several major pillars of my life so that I’m always sprinting away from being with that thing. Because I know that it’s there and I don’t want to talk about it or look at it.

[00:08:06] Dylan Bain: Oh my God. That is so poignant because I was just having this conversation this morning with a potential client. And they said, well, you know, but I’m really dialed in. And I said, yeah, but that’s your comfort zone. You have adrenalized and have focused on this thing because you don’t want to have the conversation we’re starting to have, and so you’re desperately trying to move it back. I would love you to talk more about the shame and that fear resistance that people build up. I’m sure you’ve seen that a lot, particularly because you’re touching into sex. I’m touching into money, arguably maybe more intimate, but they’re in the same jar, so to speak.

[00:08:42] Jordan Gray: Totally. They’re very, yeah, similar place on the shame continuum. It’s funny. I actually remember — so my longest term mentor, P.T. Mistlberger talked about how, you know, he was like a direct disciple of Osho, and he was very active in inner growth work in the ’80s.

[00:09:00] And in one community that he was a part of around my birth year, coincidentally, there was one process — I forgot the name for it, but it’s like a 30 person experiential, you know, shadow work group. And one by one, each person would completely disrobe. They’d be completely naked, they’d stand in front of the group, and they would talk about every detail of their finances, just like, every bit. Like, here’s my debt, here’s my savings in this account, and like, that was the process. Everyone else is clothed and just sitting there and looking at you. And you get completely naked and say everything about your money. It’s like, yeah, that would be, you know, an edge not just in the ’80s, but for anyone ever. I mean, I can’t speak to the future, you know, in perpetuity, but like, yep. This stuff carries a lot of charge for people.

[00:09:47] Dylan Bain: Oh my God, I’m blushing just thinking about that. Like, and I’d be happy to talk about like, the balance sheets and stuff in my life. But the idea of having to do it naked like, you’re getting naked twice. Totally. Right?

[00:09:59] Jordan Gray: Yeah, I mean, the second kind of nudity, I think most people don’t touch on forever. You might have a sexual partner in your entire life, and so you’ve been physically naked in front of someone. Have you ever had that conversation of like, here’s actually everything about my financials? Unless you’re talking to you or, you know, maybe your accountant or bookkeeper, but even then you can hide certain accounts from those people, so. What was the original question? This is a big tangent.

[00:10:25] Dylan Bain: No, but you know, it was right in the same spot though, right? Like, because I do have couples who come into the financial court class, and they’ve been married for 40 years. Yeah, they’re married for years, they’ve got kids, they got grandkids. They’ve done everything, but they’ve never had the conversation we’re about to have. And so what I would like you to do is to talk a little bit more about the shame and fear that people build up like — and I feel like on some levels, these things function as defensive mechanisms. And so I would love your experience and be able to just kind of like, get the Jordan view of that shame and fear.

[00:10:59] Jordan Gray: Totally. I mean, our minds are meaning-making machines, and when it comes to our physical body, our self-perceived and other perceived physical attractiveness, our sexual desirability, how financially fit or abundant or not abundant we are. Our mind loves — and you know, society and conditioning and millions of messages that we get — love to tie these things of like, ooh, this thing, this means something about you. In fact, it kind of means everything about you. This number, it’s your identity. It’s your worth as a partner. If your physical attractiveness goes down, oh, they might divorce you. Oh, you lose a job? Oh, you made three bad financial decisions within a two-year period. Guess what? They might leave you even more.

[00:11:46] And like, you’re going to get different checks and balances, different weight attributed to different things based on the default conditioning — the expression of — at least in default Western conditioning, this notion of, you know, women are sex objects, men are success objects. And these things are balancing and shifting over the last 60, 70 years, maybe compared to most of human history beforehand. But there’s still deep feelings associated with both these things of like, yeah, if a woman loses physical attractiveness, if a man has several hits financially and is like, ooh, I’m not doing the core thing that I’m supposed to do. Like I’m dropping in this really important pillar, and maybe it means something about me. Maybe I’m going to lose love from my kids, from my partner, from my in-laws, from my peers, from my coworkers.

[00:12:41] So yeah I think, you know, people go to great lengths to, you know, I was talking about reaction formation before, to guard these things that our identity is so innately tied to, that until we hold it up in the light at all, and see at least some percentage of the fallacy of like, is my bank balance my worth? Is it just a fucking number? Do I need to make this mean it’s absolutely everything? And if it dips for, you know, more than a quarter consecutively, then like I’m a failure as a person, and I should probably leave that before they leave me.

[00:13:20] Like, people just have such deep conditioning around this stuff that it’s inevitable that shame and whatever meaning we make these things will bubble up quite persistently until we see the fallacy, have the conversations, bring the shadow content out into the light.

[00:13:38] Dylan Bain: Have you ever seen people use shame as a safety blanket?

[00:13:41] Jordan Gray: Oh, totally. I think that’s one of the main things that people use it for.

[00:13:44] Dylan Bain: Tell me more about that because I think when people think shame, they feel the bad feelings. And here’s a phrase — I’ll just kick up the phrase. The phrase I hear a lot in financial coaching is where they say, I would do anything to not feel this way. This sucks. And I always ask him, I’m like, what are you getting out of it? And they said, I’m getting nothing out of it. I hate this. And to me, it’s like a kid holding on to their safety blanket, and I can’t quite convince them that they don’t need it. I would love you to talk more about that.

[00:14:11] Jordan Gray: Totally. I’ll also, I’ll give to relational equivalence of what I frequently see as being examples of those, not just tied to money.

[00:14:21] So for women, you know, you talked about the 40-year married couple that have never talked about their financials. Maybe one partner has deep awareness of the money, and the other one’s totally in the dark. And that’s just their dynamic that they both play into. I’ve met similar couples who’ve been married for decades where, you know — and these are quite gendered examples — but here we are, with the woman who’s like, I’ve never had my husband see me without my face on. Like they will literally get up in the morning and do their makeup before they see their spouse of decades.

[00:14:52] Or some of the men that come to me and go, I want to nuke the possibility of ever going partially soft during sex or not being able to get it up initially to have sex. And so they will secretly take Viagra or Cialis — you know, low dose Cialis on a daily basis — and they’ll hide their pills from their partner for years on end while increasingly upping their dose to always be ready to not only be sexual, but to never have the situation where I’m not flawlessly hard immediately. Because if I’m not, the story is likely, I’ll be judged. I’ll be perceived as impotent. I won’t be a good husband provider. She’s going to leave me just like my parental figure left me 40 years ago.

[00:15:36] So yeah, people really go to great lengths to avoid shame. And last micro example, I think that’s also one of the main reasons why porn, you know, statistically more men use it. And yeah, female clients will come to me and go like, they’re just baffled by it and I’m like, there’s emotional safety. There’s no emotional risk. That’s why. Porn never says no. That’s why it’s compelling compared to his real-life — you — partner. Even if you’re excited and willing and wanting to get in there. Yeah. People go to great lengths to avoid shame.

[00:16:10] So how is shame also productive? How do people use shame as the safety blanket, I think was your way you worded it? Yeah. It’s a very convenient way to stay small, to disown our power, to not lean into certain growth edges that are completely within our range of do ability. If we are just like shrinking up and kind of in this just like tight masturbatory like, oh, but if I’m a small piece of shit and I’m not good at life and, oh, look at my bank balance. I’m so bad with money. I’m so bad at relationships. I’m still single at 31. Oh my God. You know, whatever the thing is, we get to avoid taking some responsibility. We have to avoid the next growth edge, whatever that thing is for the individual.

[00:17:03] Dylan Bain: Oh my God. And I loved your example where they’re like — in my head, I could just kind of see the person like beating themselves like a monk. Being like, whipping themselves and they’re getting off on it. Like one of the phrases I’ve heard you use in the past is like, it’s the ego jacking itself off.

[00:17:18] And that’s exactly like, I’ve seen people with their money where it’s like, they get to the end of the month and it’s zero in the bank account and they have like, this story where like, you can almost see the red cape flying behind them. And they’re the hero ’cause they get the wolves from the door and now she’s going to fuck me. And of course, they didn’t have that conversation, but you know, and he was like, well, I didn’t keep the wolves far enough away from the door. So then they spend more to create a bigger pressure to just continue to play this story.

[00:17:46] Jordan Gray: Yeah. And they get to have the 24/7 free drug drip of adrenaline of life. Oh, there’s always never enough. This is so great. I always get to be like right there, right on the razor’s edge of living. Like it’s a really, it’s a cheap secondary payoff that, you know, you get to feel this like, mission, this purpose, the sense of aliveness. In the, oh, I’m always almost fucked. Like, there’s an egoic excitement to that. You get to feel the friction of aliveness, even if your mind, even if your self-concept or identity says, oh, I hate it. I hate being broke. This isn’t fun at all. Okay.

[00:18:25] And is it at all fun? Are you benefiting from it somewhat? Are there financial decisions that you make on a monthly, quarterly, annual basis that do keep you in that range? Because just like some people love roller coasters, some people love horror films, some people love skydiving. There is some excitement in it, but like, the ego hates acknowledging that there’s even 1% decisions we’re making or responsibility that we’re taking, it’s like, okay. No, I just, of course not! I hate it. I only hate it! Okay. But maybe not, maybe something to look at and just consider that there’s a 1% sliver of enjoyment or at least secondary payoff. Okay well, I guess I get to avoid this other scary thing. Okay, cool. That’s progress.

[00:19:15] Dylan Bain: Oh, amazing. Well, and while you were saying that, the one thought that popped into my head was predictability. You may hate all of these shame points, but it’s predictable. You’ve been there for so long. It’s your homeostasis. It’s the Cialis guy, right? Like he’s taking the boner pills because now the boner is predictable. You can manipulate your wife because it’s predictable. I take six shots of tequila. I know exactly what’s going to happen. And it’s all bypassing, isn’t it?

[00:19:41] Jordan Gray: Yeah. And there’s a lot of comfort in that guarantee of like, even if it’s a situation or an outcome that I say I don’t want, there is the safety blanket. There is comfort in that familiarity of like — well, again, the same as until there’s conscious intervention and self-awareness with it, you know, people don’t tend to initially, at least — they don’t call in partners or track partners that are ideal for them. They just call in what’s familiar. Oh, you’re like my mom. Oh, you’re like my dad. Perfect. Let’s do this. And then two years in, I’ll go, oh, you’re just like this person! It’s like, well, they were from day one. You just didn’t face it initially.

[00:20:18] Dylan Bain: Fun fact. I was — I’m in a men’s group and one of the guys in the men’s group, we were having a conversation last night and he was telling me about like, well, you know, it’s really nice. And I liked this person. I’m like, yeah but, you describe your mother and then you describe this person and they’re like the same person, just 40 years younger. And he’s like, I don’t think that’s true. And I’m like, have you considered that you’re in this relationship because now you have someone who’s like your mom, but they love you this time? And now that you’ve hit two years and the cool points are off, it’s starting to come apart?

[00:20:49] And that was a conversation he was not ready to have. But it’s the same thing, I think with money of like, we either do the same thing our parents did, right? Whatever we saw. Or we do the exact opposite because we think it’s going to be predictably the different thing. And both are wrong.

[00:21:05] Jordan Gray: Yeah. I mean, I think either way, we’re going to carry the torch one direction or the other. I think that’s kind of, you know, for my world view, that’s kind of the best case scenario is we go, okay, here’s the relay race. They passed me the baton. They were able to take it this far. Now I take it, and whether I run, you know, 10 feet or a hundred thousand feet is up to me. But yeah, until you get someone to really face that personal responsibility piece of like, okay, can you be with reality, see what your situation actually is, who your desires actually are, where do you want to carry this baton, how far is up to you. Now what? What are you going to do with it?

[00:21:44] Dylan Bain: Amazing. Talk to me more about the reality piece. When you, because one of the things you said was, yeah, we want you to be with reality. Here’s something I hear a lot back. Who decides reality? And it’s like, as if it’s this like, amorphous thing that — anyone could have any version of reality. How do you ground clients into reality?

[00:22:03] Jordan Gray: Well, one of the first things I tend to lead them in with is just getting really clear about like, what the reality is of their situation. What results do you have in your life? I’ve never read the Bible, but I think there’s some quote that I’m paraphrasing and it’s like, “And you shall know them by their fruit,” something like that. I’m just like, what results do you have? Like the person who’s like, hmm, but what’s reality and whose reality? It’s like, that’s already very like, slippery mind, you know, ego noise.

[00:22:34] And I’m like, okay, so let’s just — of the infinite realities, and yeah sure, you have a different reality when you’re sober and waking up versus consuming four grams of mushrooms, like whatever. Fine. Yes. You can have your multiple tears of consciousness and blah, blah, blah. But for the sake of this conversation that we’re having, that I’m having with this hypothetical person: what are your numbers? What’s your bank balance right now? How do you feel about it? How paid off is your mortgage?

[00:23:04] Just like, how is your life going? What are the results of what you are currently sitting with? So through the filter, through the lens of, we’re talking about that level of reality, there are certain things. And yeah, the reality piece matters to me especially because, yeah, especially around money-focused clients that I’m working with. People that have really struggled for years, if not decades, tend to have a really like, patchy, creative, martyr type relationship with reality.

[00:23:36] Like I was talking to one client a few months ago and he was like, oh, the growing rate for rentals in my city. Like they’re this, but they really should be like this. And it’s like, what do you mean they should be? Really doesn’t give a fuck about your like, what you think the going rate of rental should be for the thing that you’re looking for.

[00:23:55] It strikes me as like, someone being in a sailboat and be like, the wind’s blowing this way, but it really should be going this way. It’s like, who the fuck are you to say what direction the wind should be blowing? The wind’s blowing a certain direction. Get right with the reality, feel that in the tangible three-dimensional world of like, this is a world I inhabit. I’m looking to influence or manipulate or shift energy in the material realm. So, that realm. So if the rentals are this, that’s what the rental is. If your bank balance is this, that’s your bank balance. If you think that an OnlyFans star shouldn’t make more money than the priest that your local parish like, you’re wrong.

[00:24:35] So let’s just like, strip away all the bullshit and all the noise and all the shoulds. And just get increasingly sober about how the world is currently working. Because if you strip Warren Buffett of all of his cash reserves today, and you do the same thing with me, I think he’ll probably figure out a way to monetize his life faster than I would even without personal contacts, because he has a clearer right relationship with reality than I do. And so, the degree to which you have deviated from reality into stories and shoulds tends to really show up in the tangible results in your life.

[00:25:17] Dylan Bain: You kept saying should, I’m like, that’s it. When they say should, that’s the unreality. I think about some clients where we start talking about the money stuff, and then they want to talk about sex, right? Because it’s a more comfortable topic and they, you know — and sometimes I’ll indulge them. Most of the time I won’t. But I remember that like, there’s a guy who was like, well, I find myself looking at other women, but I shouldn’t be doing that. And I’m like, well, but that’s a judgment, right? Like you’re judging that, but you are. And so like, how do you deal with where you’re at right now and then move forward from there?

[00:25:49] Jordan Gray: Totally, yeah. And that orientation is very like, I shouldn’t be doing this, is that like, self-whipping ego I should think of like, oh, like reality should be different. It’s like, okay. If you’re actually pointing out on a level of responsibility, I noticed myself looking at these women a bit too long and it doesn’t feel right and it’s like, spill the energy? Cool, clean it up. Do something about it.

[00:26:11] But if it doesn’t feel true for you, like you don’t actually want to shift the behavior. Maybe you’re, you know, you’re single and you’re looking at someone and you’re like, oh, it’s wrong, and is this toxic masculinity because I’m looking at another human? It’s like, if it’s just bullshit and you know the growth edge of self-acceptance to go, this is fine. This is okay. I’m a human mammal. I’m allowed to look at other people. Either the realm of responsibility, do something about it, shift the pattern, or you’re shameful self-assessment out of here because what is it actually doing for you? Nothing.

[00:26:41] Dylan Bain: Amazing. Amazing. Just in, just listening to you talk about like, you have to look at this and you know, it’s bullshit and it’s self-acceptance being the edge. Right? When you’re working with a client and they’re having trouble with that, and they’re saying like, but I’m not worthy of this. I’m not worth this. I’m supposed to be this other thing, and how could I be accepted until I’ve done X, Y, or Z, right?

[00:27:03] You know, and I’m thinking like in the money world, it’s like, I’ll be complete when I have a million dollars. I have clients who have a million dollars, and I can tell you categorically, that’s not true, right? Or I’ll be complete when I pay off my debt. Or I’ll be complete when I fucked a hundred women. Or I’ll be complete when I finally get married, right? Like, what is — when you’re driving towards that edge, what’s that like shepherding a client towards that edge? Where they’re going to have resistance, they’re going to have shame, the ego is just going to go completely bonkers. What’s that like?

[00:27:30] Jordan Gray: I tend to orient more towards the, you know, the sliver, the wedge of doubt. It’s like, are you a hundred percent sold? And you know, is there complete rigidity here and there’s no openness to the notion that reality could be anything but that? Are you confident that this is irrefutably the case and you can’t think of one other example of another human being out of the 8 billion plus, where that’s not the case? Or is your version of reality the objective, correct one, and you don’t actually want to change it?

[00:28:01] So like, if there isn’t a hundred percent certainty of like, this is the only way — it’s the only way it’ll ever be like, yeah. I just, I get into the — okay well, if you could be 1% wrong, if there could be any other reality, let’s just play in that 1% little wedge in the pie chart, and then see if we can make it even more wrong by deploying new behavior even if your mind is like, this is stupid, this won’t do anything. There’s, you know, nothing good will come of this. But then you get positive results from doing the weird, stupid thing. And oh no, now the 1% wedge, it’s like a 6% wedge. Fuck, my identity is feeling threatened. And then I did it again. And now the 6% is 31%.

[00:28:41] Like you just, you get into the thing and go, okay, well, if you say you want this result, then just on the behavioral level, let’s do some different things. See if you get different feedback, different data from, you know, the new reality that you are open to existing in the first place. And then you just, you build the evidence to the — at a certain point becomes so laughably like, oh, this thing just like drowns out the old thing. And now I can increasingly see how the old thing — yes, it was a safety blanket made out of asbestos and it kept me warm and it was killing me, so yeah, I will put that in the dumpster and move forward.

[00:29:21] Dylan Bain: I just get this image of a guy standing there and refusing to move, and you sitting there with shims and a hammer underneath his feet. Like, just building it up until he falls forward. Then he stands up and he’s moved. You’re like, yes! Okay, let’s get more shits. Just keep chiseling them forward. And that is how it does feel sometimes.

[00:29:39] Jordan Gray: Yeah. And you know, everyone has their different pace. You know, some people are — they come to you when like, they’re really kind of on the — they’re becoming quite tired with the belief or usually the results, like the results just aren’t resulting. So like, okay, maybe there’s something I’m not seeing. It’s usually less maybe my beliefs are off and more like, okay, maybe there’s some blind spot. There’s some way that I’m applying my definitely correct belief that isn’t going well.

[00:30:11] And for those people, there has to be enough pain. They have to have smashed their head against the same brick wall enough times. And you know, the blood’s running down to their waistband. And they’re just like, okay, maybe I’m wrong. And in that sliver of openness, then they tend to be more receptive. And yeah, the people that aren’t in max pain stage, just tend to have more fluid identities, you know, have had — I have cultivated more of the habit of like, I love when I’m wrong. Please tell me where I’m wrong, because when I’m wrong, and I know that I’m wrong, and I get to like, comb out all the psychological knots from decades of prior existence, like only good things ever come of it. So change of self-perception, change of identity, change of habits, isn’t as scary to those people because that’s just what they’ve been doing for years at that point.

[00:31:01] Dylan Bain: Well, it sounds like a lot of this is helping the client get to a yes. The shame is all no, no, no, no, no, but then walking them to a path to be able to be open and say yes. And I know in your own path through business, through relationships, that you had a number of those as well. So what do you say to the person who wants to say yes, but is afraid? What is the path to yes?

[00:31:23] Jordan Gray: Who wants to say yes to a new like, level of them?

[00:31:26] Dylan Bain: A new level. Somebody who wants to quit their corporate job and be a banjolele player, right? Or that person who’s just really been into baking their whole life and they just can’t do it. Or the person who really just wants to be able to date a woman. Or somebody who wants to make a million dollars. How do we get to yes?

[00:31:43] Jordan Gray: Yeah I mean, there’d be a decent amount of calibration as to who the person was, how they were speaking, just, you know, you can kind of hear someone’s worldview by the word choices that they make. So someone that would need a bit more leverage — like usually someone who’s really been in a sense of life purgatory, you know, has golden handcuffs, is quite comfortable. Things are fine. Things have been fine in my marriage, in my career, my finances. I’m not drowning, but I’m not happy.

[00:32:14] For those people — because sounds strange to some, but I think that like the purgatory, the forever-in-the-middle zone is one of the most dangerous places to be because people that are feeling the max pain, usually they have motivation pretty accessible because they really hate the current state of their life. They hate the results. They hate the job. They hate their finances, whatever. And so it’s easier, you know, someone with a splitting migraine and someone’s like, here’s a magic painkiller that will take it away right away. Decently high motivation to stop the pain that is very clear and obvious to them.

[00:32:47] So someone in the more middle path purgatory, for most people — again, I’d calibrate somewhat, but usually I go pretty quick to death of like, death is the ultimate motivator. You have 10 years, 40 years, 75 years if, you know, we really extend longevity from whatever your current age is. How do you think continuing on this trajectory of middle path purgatory, very quiet misery — how do you think this compounds? Even in five years? Not, you know, not your death bed, not, ooh, imagine what this feels like with 50 more years of bullshit? But like, okay, you today. You’re in this place, not really happy. Your kids are getting this version of you, your spouse’s getting this version of you.

[00:33:36] When you look in the mirror, you’re like, eh, this isn’t who I know I could be, take this and compound it five years. Everything that has any joy, brightness, aliveness, the light in your eyes. Let’s just assume that we can turn the dimmer switch down 70% on all those things. And all of your drinking, your neuroticism, your nightmares, the physical tension in your mid-back. Whatever things are the annoying kind of backburner grievances, let’s turn those up 70% because personally, I think that there’s nothing more self-esteem-eroding and just misery-inducing than conscious misalignment. I know one thing and I’m not doing anything about it.

[00:34:21] I got goosebumps saying that. It’s like, there’s something in that of like, okay, I hate my job, but whatever. I only spend all my waking hours doing it. And, you know, sure. I haven’t gone on a date with my spouse. And, you know, my kids barely respect me and don’t want to talk to me, and my spouse is clearly the favored parent. But yeah, just that state of like, I know things could change. I know that I’m nowhere near living up to the upper threshold of what my potential is. I’m going to do nothing about it. I think it just like, it really eats people. Like when people have a heart attack at 42 years old, when they look healthy and functioning and they’re a member of the country club. It’s like, yeah, if you turn your back on your heart, you turn your back on your soul, your essence on a daily basis for decades. How’s your body not going to fight back? Like, of course that’s the outcome.

[00:35:13] If you’re like, you know what? Fuck you, body. Fuck you, spirit. Fuck you, inner child. I don’t give a shit. I’m just going to show up and be a correct adult so that I don’t have to face the disapproval of my deceased parent or my friends who I don’t even fucking like, and they’re all cheating on their spouses anyways. And they’re all alcoholics. Like, what are you actually optimizing for here? Because at a certain point, and that’s, you know, circling back to the getting in right relationship with the reality, at what point do you just drop the fucking stories and go, this isn’t working and what am I going to do about it?

[00:35:47] Dylan Bain: Amazing. Yeah, like I’m all jazzed up, like nervous system wise. Like I’m ready to go run a marathon. Like, put me in coach. God, that, that could be the mic drop moment of the entire interview right there of like, what are you going to do about this thing that you don’t like? How is it going to compound? And I love that frame, especially for people who are doing nothing. I get a lot of people who are like, they’re totally avoidant. They don’t want to look at things.

[00:36:11] And I always tell them, a do-nothing strategy has a 100 percent chance of failure. You have chosen certainty. That’s what they’ve done. They’ve chosen certainty. But the idea of like, your inaction is inaction. It’s a choice. To not choose is a choice. So what is the compounding effect of that? Like speaking for myself, physically, I did that with my health. Now, going through graduate school, go back to school, get my CPA, and I chose to just sacrifice my body and be like, yeah, it’s fine. I can eat five chicken sandwiches a day. It’s fine. I’ll be okay. Well, guess what, I’m not. Putting on all the weight.

[00:36:44] Jordan Gray: And you’re doing something about it.

[00:36:46] Dylan Bain: I am now. I am now, but it’s been a hard road. But it goes right back to what you were talking about with the shame and the fear and the stories and the unreality. Because part of the unreality is, well, if I don’t look at the scale, then it can’t hurt me. Clearly not the case, right?

[00:36:59] Jordan Gray: Yeah. And I still have infinitely more respect for someone that, at any size, at any point in the trajectory goes, ‘kay, today, something changes, and like, you’re on the path at all. To me, that’s like, that’s just it. That’s like, to me, that’s the purpose of life. Of like, audit where you’re at. See what you want to shift. Ideally more often than not from a place of truth and alignment, and soul and heart versus just ego it gains. And whatever, use all of it as well, because going, well, I want to be healthy and fit and thriving so that I get to have a personal relationship with my grandkids. And because I want to be fitter and feel more attractive when I’m having sex with my spouse, even if she’s already like, oh no, like I’m great, I’m super attracted! It’s like, I know, and I also want to push this forward for ego reasons. So why not?

[00:37:52] Dylan Bain: Yeah. I want the boner for me as well. Right?

[00:37:54] Jordan Gray: Yep. Totally.

[00:37:57] Dylan Bain: Amazing. Well, okay. So when we’re talking about like, moving this forward, what do you see are big stumbling blocks for people who are always struggling? The question in my mind always comes down to people like, okay, I can see what Jordan’s saying. It’s a beautiful picture. I can see the sunset. It’s a hero’s journey. Great, great, great. But what are the stumbling blocks? If it really is that clear and that simple, what the fuck are we doing? Why are we not moving forward collectively and individually?

[00:38:25] Jordan Gray: I mean, I have several layers that I can speak to for that. I’ll skip a stone over a couple and then get deeper into a few others. One of the things keeping this on the financial, the money level stuff. If you ask anyone for an expression about money, I would say nine times out of 10, the easiest thing to pull, you know, the most top of mind thing is going to inveitably be a negative saying or expression or phrase about money. Money doesn’t grow on trees. Rich people are pricks, whatever. You have to have a job to get a job, you know. Like, just these things that are just like limiting and tight.

[00:39:04] And, I saw your post the other day about the zero sum game. That’s a huge stumbling block. If someone really — and I think the majority of people have this relationship to money, to finances of, for me to win, that means someone else loses. And I don’t have that worldview in the slightest.

[00:39:21] I have wildly financially successful friends that, you know, make $200 million a year. And I don’t, you know, no shred of my being is like, oh, you must be doing something that like harms the earth or someone else lost for you to make that. Like they’re some of the most generous, flowing, eco-conscious, whatever, all the checkpoints that someone would want someone with money to have. It’s like, the richest people that I personally know — I don’t know the rich people in the world, but I know some people that are doing great. Like they’re truly some of the best, most, you know, integrated actualized people that I know. Are all the rich people that I know like that? Of course not. People are still people. Some people use their pain as fuel and then never get off that rocket ship ride for the rest of their lives.

[00:40:09] So yeah, first level is just the default conditioning. The default narrative that is, you know, spun about rich people. And the part of us, the part of someone who sees someone driving down the road in a — Rolls Royce goes half a million dollar car and immediately goes like, oh, what an awful waste of resources. And, you know, you could have bought a house for that. You could have donated that money to charity. You can buy a $20,000 car. Why would you waste the resource on this thing? And to me, I don’t necessarily see it as inspiring. I’m super not a car guy. Like, you know, that specific example.

[00:40:49] But in my world view, someone spending half a million dollars on a car is like as much a donation to charity as someone giving that money directly to charity. It just takes a couple more steps to get there. But like them putting their money into the market, into the economy, and like buying things, I’m like, buy things away. Go for it. Like, it’s still going to whatever your favorite charity is anyways. It just like, you know, ping pongs around for a while.

[00:41:15] So the zero sum game, the terrible condition that people get of people with money or awful people. And I’m not an awful person, so of course I’m not going to play that game. Yeah, the conditioning is awful. Habit, momentum, the things that they’ve seen there. Parents, grandparents, peers, mentors, whatever. Just how the people around them, the people, their caregivers acted around money. It can feel like such an active break from your parents or caregivers of like, oh, I disagree with this thing that they always said is really make sure you save every penny! Or make sure you always do this tight, scarce thing. Or business owners are all jerks because my boss was a jerk once, and don’t be a business owner.

[00:42:00] You know, whatever the story is that we inherit, we go, oh, I’m going to have to like, go against one of my parents top five biggest teachings that they really made sure to get in there at a young age and consistently. If I go against that, it’s like that kind of break in reality from — yeah, just like that level of conditioning with our closest people can feel like, that’s like a slap in the face. I’m like, I can’t go against that. That was like one of their biggest, most important things.

[00:42:31] Dylan Bain: Well, then there’s got to be the question of who am I? If I’m going to dismantle this thing, this gift, and I use the term gift lightly, right? This gift my parents gave me, and I’m going to put that aside. Then who am I? I’ve always had it. Who am I without that? Like, I feel like there’s a grieving process that actually has to occur there to grieve the old perception. And then the old safety, the old certainty, I kind of feel like there’s some people who like, they try to white knuckle it, like they try to force it. I don’t have to grieve it, I don’t have to look at it. I’m just going to just, I’m going to be really disciplined. That’s always the phrase I hear men say, I’m going to be disciplined. And then they’re completely going backwards at light speed in about a month and a half, right? Because they have to go through that grieving process.

[00:43:14] Jordan Gray: Totally. I mean, there’s going to be grief, yeah, of any like, oh wow, I spent this number of years with this level of awareness. And now from this new vantage point, I see how not it that was. And so there can be grief of like, hmm, the story would be as the identity begins to shift, did I just like lose those decades of life living under this totally bullshit narrative? And if so, people don’t tend to just automatically snap to, well, new awareness, new life. Here we go! Yeah, there was a like, oh, wow. I was in that jail cell for quite a while, and there wasn’t even a key. I could just walk out. But I didn’t have the awareness. So that’s just the next iteration of a new creative way to whip ourselves like, oh, if only I’d known. You didn’t know. Otherwise you would have acted differently. Now you know, no need to shame yourself. Move on with it. Oh, amazing.

[00:44:08] Dylan Bain: Yeah. When I start teaching people how to save money and invest and like grow that, you know, so their money’s growing by itself while they sleep? They always go like, I always see this like shame drop off of like, oh I should have done this 10 years ago. And I was like, what were you doing 10 years ago? Oh, I was traveling in Thailand. I was in my first marriage, totally in love. I was like — there’s always something. And I’m like, okay, so you weren’t in a place where you’d even see this. How could you possibly expect yourself to make these choices if you yourself had no ability to even see. You didn’t have eyes!

[00:44:40] Jordan Gray: Totally. I mean, the relational equivalent that comes to mind is a couple of months ago, a woman came to me and she was like, whenever my husband and I get into an argument, like I just, escalate like crazy. And I just, you know, my mind, my ego gets hooked in and I just like, can’t put it down. And I like just, I turned up to 10 and I stay there for days.

[00:45:00] And you know, with a little bit of question and answer, it comes out to like, well, where’d you learn this? Well, my mom modeled that to me because she, that’s how she argued with my dad. And it’s like, okay, then you came by it honestly, like it was modeled to you. You as a child were like, okay, that’s how to be as an adult. And then you carried it forwards until it wasn’t fun anymore. Like, to me, there’s so much room for grace and compassion of like, you did what you did with the level of awareness that you had.

[00:45:32] Dylan Bain: And there’s the forgiveness piece that’s got to go in there too, right? You know, so many people will come in whether with budgets or with arguing spouses of being like, I should know better. And again, there’s that should, right? I should know better. My question is, well, but why? Like with budgeting, you were mammals, right? Like we were descended from the most advanced caveman ever created, right? And that caveman was concerned, was feeding itself, fucking his wife, and staying out of the cougar, right? Like that was the thing. That’s all they had to worry about.

[00:46:01] Where’s the budget and spreadsheet? Us as the monkeys now have anxiety because of our spreadsheets. There’s no God given reason why you should just know how to do this and especially on the relationship side, being in such a fragmented society, right? Like, I live in the suburbs. I’m surrounded by people. I don’t know any of them, you know, let alone be able to have a conversation about raising kids, or what do I do with my wife when she’s upset, or like — we’re so fragmented that there has to be at least some level of acceptance and forgiveness for ourselves to say, yeah, it would be nice if I knew this, but I don’t. And so now I’m going to hire the people. I’m going to find the people who’ve got the life I want. I’m going to be with them and I’m going to glean the knowledge I can from them.

[00:46:39] Jordan Gray: Totally. Yeah, just, you know, really allowing yourself to see yourself as being inside of a system, society, set of narratives, conditioning stories, money beliefs that is 99% false, working against you, designed to keep you small. And then like every now and then, there’s going to be some little sliver of wisdom or some life raft or something that can have you shift directions, like relationship equivalent, the money side.

[00:47:10] It’s like, if most of the models and most of the things you’re seeing in TV and movies, peer group, aren’t healthy and aren’t the direction you want to go in — to me, there’s infinite reasons to not like, set up shop there and just like live in the swampland, but to have compassion for — of course, I’ve been acting this way. How would I not? It would have been a miracle for me to just like, figure this out on my own or to transcend my entire family system or a larger cultural narrative, and just like pop into the healthier freeway lane where I can add value and utilize leverage and like, figure out some stuff that no one around me knew how to do. Yeah, it’s just like, of course.

[00:47:54] Dylan Bain: Yeah, amazing. Amazing. And that’s of course, where you’ve come in with the relationships and that’s where I’ve come in with the finances.

[00:48:02] Jordan, this has been an amazing conversation. And I think, I feel like we could talk for like another three hours on this topic. But before we sign off, how could people find more of, you know, more Jordan Gray in their life?

[00:48:15] Jordan Gray: Google my name. If you go to JordanGrayConsulting.com, that’s the main hub where everything else goes from. You can find my Instagram, you can find me on Amazon, but JordanGrayConsulting.com is the main spot.

[00:48:27] Dylan Bain: Fantastic. We’ll link that up in the show notes.

[00:48:30] Jordan. That’s been an amazing conversation. Thank you so much.

[00:48:33] Jordan Gray: Thank you, Dylan. Super fun.

[00:48:36] Outro: Thanks for listening. The conversation doesn’t end here. Please share the show with friends and make sure you keep up with all the latest updates on Instagram and Threads @TheDylanBain, and dive deeper into the world of finance with me at DylanBain.com where you’ll find insights, resources, and strategies to reimagine your money story.