255 | Work With Your Feelings: EQ, Emotional Regulation, and Rewriting Your Money Story with Jess Robson

Hilary Hendershott: Well, hello, Money Lover. I have with me today someone fantastic. Her name is Jess Robson. She’s a coach who works with business leaders and their teams to expand trust and connection–amazing–so they can move with more speed and purpose toward goals. Her work focuses on feelings. We’re going to talk about feelings today!, helping you grow your emotional awareness and emotional intelligence so you can work with your feelings instead of getting worked by them.

Hilary Hendershott: Wow, there are moments I could use that. She’s also recently launched a podcast called Too Many Feelings, Too Little Time, which helps listeners get unstuck and stop spinning so they can spend more time doing what really matters to them. Welcome to the show, Jess.

Jessica Robson: Thank you so much. I’m really excited to chat today.

Hilary Hendershott: Yeah, I can’t wait. Emotions and money are so intertwined. And in my industry, for someone who calls themselves a financial advisor, the ability to even have a conversation about emotion seems rare, so I think we’re gonna have a good chat today. I hate the phrase, “Treat me like a 3rd grader.” But let’s set the stage for this conversation with some definitions.

Jess Robson: Totally.

Hilary Hendershott: Start with the basics. Where in the world–I obviously know human beings have a lot of emotions–but where do they come from?

Jessica Robson: Oh, man! And that is a question that people who study emotions and neurobiology and feeling are literally still answering. So this is what I love about–love/ hate for lack of a better term–about working in the world of emotions is because the number one, I don’t know if you want to call it push back or “yeah, but” that people would have about it is, are emotions even real?

Jessica Robson: And what we know, I mean, “Thank you for the question, that’s not helpful” to the people who are questioning the validity. But what we know is that number one, off the cuff, each of us as individual human beings out in the world humaning around, we each have our own very distinct, very unique emotional experiences, emotional backstory and emotional climate, when it comes down to it.

Jessica Robson: As a general–let’s call it a generally accepted principle–is how emotions happen is, we actually have a physical input first. We have a felt sense somewhere in our body which triggers an emotion- that triggers a reaction that runs through our emotional brain, so the limbic center, before transferring forward into our prefrontal cortex, which is where our communication and rational thought live. And the tricky part about our emotions…

Hilary Hendershott: Is that when we get messed up by them? Yeah.

Jessica Robson: Literally. Yes. So it’s that transfer from the limbic system forward into where language comes from, where rational thought, like I mentioned and communication come from is inside the limbic system, is also part of our brain that’s the least evolved from prehistoric times. So our emotional brain- things get a little bit clunky and stuck up because our brain, that part of it, is assessing for where there’s a saber-toothed tiger in previous times, and constantly scanning, constantly scanning for threat because it’s working, and it’s doing its job to keep us safe.

Jessica Robson: Unfortunately, current day threats are social and emotional mostly, right? And so we’re interpreting…

Hilary Hendershott: Less saber-toothed tigery, more “I feel rejected-y.”

Jessica Robson: There you go. You named it exactly. And, not wanting to get too far into it too soon, but that’s where things can go a little sideways. Because if we were to just trust everything that came through our emotional brain and threw itself forward into our language, into our actions, into our behaviors, we’d be taking a whole bunch of movements; taking a whole bunch of actions that probably wouldn’t align with what we really wanted, because we haven’t fully processed what that part of our brain’s really trying to tell us.

Hilary Hendershott: Yeah.

Jessica Robson: And really thought through and gotten ourselves to a really integrated, rational state before moving. So emotions come through our body, come through the emotional brain, and then move through the rest of our system after that.

Hilary Hendershott: Okay. That was a good answer. I have more questions. So we’re just gonna leave that one be, and we may come back to it. Let’s talk about three terms and hopefully provide some definitions here. So, and I don’t know if these are synonymous, EQ, self-awareness, and emotional attunement or regulation.

Jessica Robson: Hmm.

Hilary Hendershott: Should we go one at a time?

Jessica Robson: Let’s do it.

Hilary Hendershott: EQ- obviously, I know what it stands for is emotional quotient which comes from the IQ. So then people coined the phrase EQ. What do you mean when you say EQ?

Jessica Robson: So when I say EQ, I was trained in a specific emotional intelligence model. And inside that model we define emotional intelligence as a set of social and emotional skills that ultimately allow us to live, act, exist in a more effective state, more frequently.

Hilary Hendershott: Hmm.

Jessica Robson: Yeah. So it takes it out of concept and turns it into tangible, actionable skills that literally anybody can learn.

Hilary Hendershott: So, then, is that synonymous with self-awareness?

Jessica Robson: Self-awareness is a skill inside emotional intelligence. It’s actually an emotionally intelligent skill. And like, specifically inside that model, I talked about the EQi 2.0. We name that skill “emotional self-awareness.” So it’s a pretty like specific aspect of overall self awareness. But I do see an expanded sense of self awareness as a skill that serves our emotional intelligence.

Hilary Hendershott: Okay. And emotional attunement?

Jessica Robson: So, I will put emotional attunement and emotional regulation as separate.

Hilary Hendershott: Okay. Okay.

Jessica Robson: Emotional attunement, I look at it two ways. So there’s internal attunement or internal recognition. Again, this is another one of the skills inside emotional intelligence. Being able to understand, identify, and discern distinct differences in our own emotions. And also witness and understand how our emotions affect people around us.

Hilary Hendershott: Aha!

Jessica Robson: Yeah, there’s another sense of emotional attunement that we look more so in like a relational dynamic, where it’s our ability, and it’s an empathetic practice–empathy is another one of these emotional intelligence skills–but it’s to be able to look at someone else and understand or discern what emotional state they may be in. Not necessarily taking that on, but just be able to see what state they’re in, as well.

Hilary Hendershott: Okay. And I noticed one of the tools you sent me–and we’re going to make this available to listeners in the show notes for today’s episode. But you referenced The Feelings Wheel.

Jess Robson: Yeah.

Hilary Hendershott: And yeah, I was part of a global organization called Entrepreneurs Organization. And each month, we would update our small group from the Feelings Wheel. So there was this whole framework of updates we would do, and that was- It was really informative for me to learn that there are people who struggle to identify their emotions. I don’t struggle to identify my emotions. I sometimes struggle to control them.

Jessica Robson: Like I feel them really well.

Hilary Hendershott: I know what it is. Yes, yes, this is why I’ve learned–my major adulting skill is to learn that if I’m upset, sleep on it before you send the email.

Jessica Robson: Oh, my gosh! I’m such an advocate for write the email that you want to send, and then send it to yourself.

Hilary Hendershott: Save it in drafts.

Jessica Robson: There you go. Yeah, yeah, there’s something about that, for sure. And I think The Feelings Wheel is such an incredible tool, like, I always put my hand up for being someone who really struggled with emotional identification. I grew up thinking it was like three emotions of happy, sad, or tired. By the way, tired is not on The Feelings Wheel.

Hilary Hendershott: Tired is not an emotion.

Jessica Robson: Yeah, it’s not an emotion. And getting a more, like an expansive emotional language or emotional literacy, that tool–it’s literally feelingswheel.com–it is incredible for being able to not only see how many emotions are actually identifiable, but then also to challenge ourselves. My friend Makenzie Chilton, she’s a previous therapist who’s now a coach, and she used to always position… when someone would say, I’m feeling X–happy, sad, angry–she’d go okay, pull out the Wheel. If you’re angry, but you can’t say angry, what other word are you?

Jessica Robson: And this is where we get to get into that like- I call it fun, because it’s “my thing.” The fun practice of getting more granular about what it is we’re actually experiencing; what it is we’re actually feeling.

Hilary Hendershott: Right. Right. Okay, well, feelings is fascinating. And let’s tie it to money. Yeah? Money. Oh, my goodness, it’s an emotional topic. And I think more so for women, although I’m not sure if I just talk to more women, or if they’re more open with me- like, I’m not saying that that’s a fact. But why do you think money turns out to be such an emotionally charged topic?

Jessica Robson: I sense that there’s emotional charge behind money, and I will point people in the direction of people that I know that work on money story a lot more frequently. But from what I understand, and even from a little bit of the personal work that I did about understanding my own money story, is the emotion comes from experiences that we watched around money growing up, and the story we tell ourselves about what that means about us, what that means about people in the world.

Jessica Robson: And it’s through the storytelling about what money means or what we mean in relationship to money that causes this emotional attachment that increases our shame; that amplifies guilt; that tells people the story that, or owns the emotion of disgust around money, whatever it is that comes up for people. I really do see how story amplifies feeling or amplifies emotion, and then makes it really real for people, which I can only imagine is, is something that’s nuanced to tease through when you’re working with your clients.

Hilary Hendershott: The narrative runs the show–I experience with people, myself and people–the narrative runs the show until you’re willing to look at it as a narrative, but then, all the time you spend not dealing with it, the repression becomes another thing. It’s like this cage that people live in about money. What I’ve learned, I mean, I’ve been talking with people about money for years, the vast majority of us, I mean, I would go so far as to say 80% of us are miswired when it comes to money. There’s like a dysfunction to it. Of course, everyone’s dysfunction is unique.

Hilary Hendershott: And so I, I find that for many people, when you go with your gut about money, we go awry. Right? So what would you say about that? About, we have so much in society today, we’ve made so many advancements. And yet some of the doctors and scientists making the medical advancements are making mistakes with money.

Jessica Robson: Yeah.

Hilary Hendershott: Why do you think that? How do you explain miswiring like that?

Jessica Robson: Oh, gosh! When it comes to the wiring itself, I think there’s–what I understand about the way that our brain works around decision making has to come down to the things that we expose ourselves to and then how much we’re willing to try different things without proof that it’s going to work.

Hilary Hendershott: Ooo. That’s juicy. Tell me more about that.

Jessica Robson: What I witness in, in a lot of the coaching that I do with the clients that I work with is we get stuck in habitual patterns. So whether that is– and I’ve been open with this, I don’t coach people on finances or on money–and so I put it in the context of habits or ways that they show up at work. Actions or behaviors that they use with their team, ways that they operate to get heard around the boardroom table. Whatever it is that you’re noticing where there’s like a consistent or habitual pattern.

Jessica Robson: So what I always look at with folks is, what’s the action that you’re taking that’s consistent or persistent? And what’s the outcome that you’re getting? “I’m getting heard because I get loud when I’m trying to get a point across.” We’ll just use that as an example. So those people, or in these situations, it’s often that they have an experience that if they wait to speak at the boardroom table, that they’re asked to talk, because they always talk first. And so there’s stress for them between wanting to say something and then sitting back and letting other people contribute.

Jessica Robson: The more people allow themselves to be exposed to that challenge, or that change, of doing something differently, or they’re allowing themselves to have opportunities to find success, i.e. the outcome they’re looking for, through new avenues. But it’s that space in between of willingness to try something different–even if the thing they’re doing doesn’t get them what they really want, trying something different seems scarier or more challenging than going with what they know, and just getting a maybe a mediocre outcome more of the time.

Hilary Hendershott: It sounds a lot like the experience I had when I hit my own financial rock bottom. And I’ve shared about this on this podcast many, many times. But it was like, I really got clear that my behavior was a set of patterns. And that the behaviors were producing bad results, and that if I wanted to produce different results, I needed new behaviors. And so I just got like, really awkward. I just started doing stuff I had- I was like, I don’t know what I’m doing. I’m just doing the opposite of what I used to do.

Jessica Robson: Yes. Yeah. Nailed it.

Hilary Hendershott: Yeah. You know, my view of it now is that it was all fruitful, but I think in the moment, I was like terribly strange to people.

Jessica Robson: Yeah. And it feels so uncomfortable to go outside of what you know, even if you can see that it’s not working, or it’s exacerbating the issue. I talk about it with folks who are kind of in these developmental pivots. Much like you said, we always talk about doing the one opposite action, right? So if I keep on cutting people off around the boardroom table; if I keep putting my hand out first. What’s the opposite action? I sit back, and I like some people– you can do it on Zoom when you turn the camera off–literally need to hold their lips shut. Simply, is this, like, gentle exposure to trying an opposite action.

Jessica Robson: Right. So let’s say, like I noticed at one point that I had an overspending issue, and that I was spending or shopping online when I was feeling a little insecure. I was able to pick up on the nuance of that over time, and so I noticed, like I would open a cart on a website, and the minute I would get to the checkout page, the one opposite action was to close it down.

Hilary Hendershott: That’s powerful.

Jessica Robson: And it felt strangely large in the moment, because I was in such a repeated habit of just like, this will make me feel better. It’ll make me feel better. It never did. And I think that’s the, the opportunity is, what’s the opposite action?

Hilary Hendershott: I love it.

Jessica Robson: What’s one thing I could try that’s different? And then the flip side to that, and you mentioned it, and I love that you use the word “awkward.” I use the word “clunky”, people use the word like it feels like “friction”, or that there’s a big rub in trying something new. That’s grounded in this principle that Dr. Dan Siegel developed, called the Window of Tolerance. And I call it like, how much capacity for tension each of us can hold.

Jessica Robson: And the goal that we’re creating with people, or people that I’m working with, especially when it comes to how we integrate our emotions into our decision making, into how we show up out in the world, whether that’s professionally or personally, is, we’re constantly working on, how do we expand or open up our Window of Tolerance, or how much intense emotion or stress we can handle while still being the version of ourselves that we want to be; while still taking the actions that we want to take, that align with our values; that keep us in integrity with what we’re committed to.

Jessica Robson: And how do we also experience more–let’s call them like extreme emotional states–but find ourselves able to come back into that regulated, integrated, more open and more whole sense of ourselves.

Hilary Hendershott: Wow, that was big.

Hilary Hendershott: I think for many people, most people probably, when they start to examine their financial life, the emotions are big. They start out pretty darn big. What is your coaching; what is your advice; what is your thought process around, how should I interact with, as a human being, these huge emotions which make me want to do things in the moment, and then inevitably, most of the time, I regret them later. And I’m probably speaking for many people who are listening, right? How do I conceptualize that?

Jessica Robson: Yeah. The one thing I’ll absolutely say off the cuff and off the top… Feeling big feelings can be really, really scary. And I think that’s a number one reason why we stay in patterns that ultimately don’t work over the long run, because exposing ourselves to the bigness of certain feelings isn’t something we’re taught all the time.

Jessica Robson: I mean, I was a bit of a what I like to call a “champagne bottle kid.” I would rather push things down and shake the champagne bottle and be really on edge quite frequently, rather than feel into something, allow it to be there, understand or learn what I could from it, and then move on. And that’s what I learned about emotional regulation and integration and processing over time.

Jessica Robson: So what I’ve experienced around big feelings is, first of all, they can be incredibly scary for a lot of people to feel, especially if it’s something that we’re touching in on for the first time, and we don’t have a lot of experience in that space of feeling emotional distress, or emotional friction.

Jessica Robson: My friend Ashley Brodeur, she’s a psychotherapist out of Toronto, Ontario, and she recently introduced me to an acronym that was offered up by Tara Brock, and it’s RAIN. And for people who are just starting to identify that there is a big emotional experience going on in relation to finances, in relation to money, or anywhere that they’re noticing it. This is a really accessible way to start investigating; feeling–safely–investigating, and then knowing what to do with a feeling as it arises. So the R in the RAIN acronym is recognize.

Jessica Robson: Can I simply recognize that I’m having an emotional reaction, a real emotional response to something that’s coming up. You might feel it in your physical body. You might feel your heart start to beat faster. You might feel your throat start to get tight; shoulders. I get a lot of my emotions in my traps and my upper back.

Hilary Hendershott: Oh, wow!

Jessica Robson: So that’s where my body normally feels first. Some people will get like an unsettling…

Hilary Hendershott: Mine are in my stomach.

Jessica Robson: Yeah, I was just gonna say, tight tummy.

Jessica Robson: The A in it is to allow. And I think this is where a lot of us have the opportunity to do a little bit of slowing down and allowing the emotion to be there. It’s so human and so natural for us to find a vice to feel better in the moment. But what that does is it’s bouncing us off our emotions and keeping us in patterns–that we talked about–that might not work. And it doesn’t give the emotion a chance to give us a little bit of the insight it’s trying to poke through the dirt, if you think about it as a seed. So in allowing the emotion to be there, it doesn’t mean we have to do anything with it. We simply have to recognize it’s there, and then give it a second to do its thing.

Jessica Robson: And if we can sit with it, we then have the opportunity to access the I, which is investigate. And in some situations, whether it’s a really, really big feeling or too overwhelming, investigating it–that’s where some people might notice that they could use an expert insight to help them process it through or do that investigation piece. That’s where counselors and therapists sometimes come into play and can be really supportive.

Jessica Robson: Other times, if it’s a lower intensity emotion, or it’s just something that’s there that we can get curious with, we can ask, “Okay, what’s this about? What’s it connected to? What’s here for me to understand?”

Jessica Robson: And then the N is nurture. What can I do that’d be really nurturing for myself? How can I take care of myself in this moment, knowing that I’ve got something going on? I might not know everything I need to know about it yet, to make, you know, to take my next step in an integrated, aligned, or purposeful way. So what can I do for myself that would be really gentle? And this is a little bit of what we would consider like preliminary emotional regulation skills.

Jessica Robson: Deep breathing. Breath work is an incredibly important skill, and when I’m talking about breathwork, it’s literally taking a deep breath through your nose for four to six counts, holding it for a couple counts, and then a long, slow exhale. And doing that four or five times is a really nurturing thing for our nervous system to slowly start to calm and regulate. Other people, it’s stepping outside, getting into nature, going for a walk. For some people, it might be meditation. But how can we nurture ourselves inside that experience, too?

Hilary Hendershott: When you said you were a champagne kid, that’s what I thought you were talking about, drinking champagne to stop feeling emotions.

Jessica Robson: I mean, I’m not saying I didn’t. But that’s like, and that’s what I talk about–vices. We’re, in so many different ways like– I had a really long day, or I had a really rough week. I need a drink.

Jessica Robson: And there’s no shade or shame. I consume, and people that do; people that don’t, it’s all good. It’s simply, there are so many different ways that we numb ourselves out a bit from the different life experiences that we’re having. And again, I know the bigness of what I’m asking people to do in this, especially in bigger feelings. But what if we sat with it for just a second. And instead of numbing it out; trying to smooth it over; trying to shove it down, we let it be there long enough for us to know what it’s trying to tell us?

Hilary Hendershott: Yeah.

Jessica Robson: “I’m nervous because this feels really important to me. It feels really important for me to do something meaningful with my money, so that I set up my family for a different future.”

Hilary Hendershott: Yeah.

Jessica Robson: Right? There’s something there for us to take out of those feelings that are coming up, and if- I’m going to say like, if we had the courage and we’re brave enough to sit with it and put our bottle of champagne, or glass of champagne, or glass of whiskey to the side, even for five minutes. That’s a really effective way to start to get into relationship with these feelings that come up and work with them in a new way.

Hilary Hendershott: I noticed–and you talked about narrative when we first started talking about emotions, or story–I noticed for me, if I’m able to disconnect the big feeling from the story, the story inevitably is making me worse off in the future.

Jessica Robson: Yes, yes.

Hilary Hendershott: If I can just set it aside and feel the feel, it helps. There’s like a- the distance from the intense feelings.

Jessica Robson: Totally. Yeah. What I would add to that is… the thoughts, the stories that we tell often pour like lighter fluid onto our emotions. And so the more we tell ourselves the story, the more intense it’s going to get, the more worked up we’re going to be. And the further away from the facts of the situation we get.

Hilary Hendershott: Right.

Jessica Robson: And, in decision making, for example, just thinking about how we need both. We need external data. We need facts for a situation. We need our head. We also need our heart. We need the emotions to give us the data that they’re there to offer us. But if we overplay either of those- if we were to completely ignore our feelings about something, or the story, then we’d be missing out on something really useful to help direct us in a meaningful direction. But if we only lean into the story, we miss out on really important facts that could help us, again, make a more integrated, purposeful decision that serves the long term.

Hilary Hendershott: Right. So one of the things that’s very interesting in my world, is how our emotions about investing- so, money is separate from investing, I mean, investing is a subtopic of money. But there’s a lot of emotions around investing.

Hilary Hendershott: More and more people are leaning into stock market investing. I mean, I started doing this 25 years ago, and you had to like really pitch people, some people, on leaning into that. But it really is like in the Zeitgeist now. And we have a model in my industry called the Cycle of Market Emotions–market being the stock market. So the stock market goes up and the stock market goes down, and our emotions tend to go with the market. So at the top, we’re elated; we’re excited. Everybody wants in. And at the bottom, we’re terrified. Everybody wants out. Now, of course, we don’t know when it’s the top or the bottom, only in hindsight; we only know as we look backward.

Hilary Hendershott: But the facts of the case, as you were talking about, the data, the reality of it, are that at the top, stocks are the most expensive, and the only place for them to go is down. And at the bottom, stocks are on sale. They’re cheap, and the only place for the price to go is up. And yet even some of the world’s smartest, most successful people really struggle to internalize that. And just being transparent, even I, as I watch the stock market go up, am joyful about that.

Jessica Robson: Yes.

Hilary Hendershott: Right? And I don’t like watching my own accounts go down. I don’t enjoy the process. I’m intellectual enough about it to know that I can’t, I’m not going to do anything about it. But I suffer from the same thing. So can you just address this phenomenon called, our emotions are exactly the inverse of what they ought to be, and how do we be about that?

Jessica Robson: Yup. I love this example, because it really– I mean, I don’t love the stress and tension people feel in the process of investing in that way–but what I love about this example is it really amplifies the necessity to not trust our knee-jerk emotion. And why, like I was saying, it’s so important to yes, feel our feelings, take the insight from them, and also know that there is a lot more to look at outside of how we feel about something when it comes to making a sound–and when I say sound, I mean like values aligned, a purpose-driven, meaningful decision.

Jessica Robson: So, when I think about where you were sharing with like joy escalating as the market goes up, that happiness for some people, or the anticipation, or the expectation that they would build off of that might take them past what they had set as an upper limit of where they wanted to see a certain stock go to, or a certain amount that they were willing to wait to see if it hit.

Hilary Hendershott: Sure. Or they’re imagining themselves as wealthy.

Jessica Robson: Exactly. “This is going to be the one, and the multi millions are going to rain down on me.” Whatever that is. And so when expectation, elation, joy–all of those really and like beautiful big feelings that we want to feel–overtake our ability to see the full picture, if you will, then that’s where… That’s that more tactile data that I was pointing at, that could take them out of integrity of the commitments that they made to their money, or to the whole reason they got into stocks in the beginning; their why.

Hilary Hendershott: Right.

Jessica Robson: And so, that’s that kind of practice of, yeah, we want to feel all those things. We want to be excited. We’re not, like emotional intelligence isn’t about becoming like an emotional cucumber, you know, where we’re always just cool and like just hanging out. It’s about integration when it comes down to it. It’s really about integrating, okay, yeah, I’ve got this really big feeling. Where do I need to ground myself? What is it that I need to remember that I was initially committed to? Or that’s like, how am I grounding myself and my values around this, so that I can be really excited, and I can also be purposeful? Where I can be really nervous, and I can also be really purposeful. And that’s again one of these pieces of, of how we’re holding capacity for intense emotions. I think we think intense emotions that we think of; the more challenging ones to sit with–grief, stress, anger, frustration. An intense emotion can be mass joy, or massive elation, right? So the more we can hold those big feelings, but do it in an integrated way, where we are still rooted in our purpose, in our goals, in our values, in our vision.

Jessica Robson: That’s where we’re able to kind of counter ourselves and go, “Yeah, I’m stoked and. Here’s what I’m actually here for.” Yeah, “I’m totally freaked out right now, and I’m watching all my accounts go down. And. What’s the long term? What am I committed to here that’s beyond this moment in time?”

Hilary Hendershott: When I first started in the business, I told one of my first clients who got really excited about watching her accounts grow in value, I said something like, “You know, look at, to the degree you’re happy about the upswings, you’re going to be sad about the downswing, so like knock it off” kind of a thing.

Jessica Robson: Right.

Hilary Hendershott: Her reply was something like, “Okay, I’ll, I’ll try to stop feeling good about that. Thanks.”

Jessica Robson: Like, well, you’re welcome.

Hilary Hendershott: I never said that twice. Just so you know. I do learn.

Jessica Robson: Self-awareness. Yeah. Expansion.

Hilary Hendershott: Okay. So a lot of our financial learning- because, a child’s brain is very impressionable. Money is super conceptual, very hard. Anyone who’s taught their kids about money or tried to, you realize that money makes no sense to a kid.

Jessica Robson: Got it.

Hilary Hendershott: And so they take on; we take on, mindsets, attitudes, and emotions of money from our parents, or the people who raised us; the people around us. “Money doesn’t grow on trees.” “There’s never enough money.” “Money is the root of all evil.” These kinds of things. And then sometimes people realize and have the opportunity to transcend what was possible for their parents, or the people that raised them, about money, and I watch them block themselves.

Jessica Robson: Hmm.

Hilary Hendershott: In other words, “I can see that frontier, and I could step into it. But I don’t want to basically be better than my parents.”

Hilary Hendershott: What would you say about that, or are we now getting into therapy?

Jessica Robson: I mean, yes. And there’s so much like- This is where we let narrative and story dictate our possibilities.

Hilary Hendershott: Yes.

Jessica Robson: Right? Where we really like- Number one, for someone to be able to identify that and be able to see like, okay, this is actually something I’ve got baked in, that’s intrinsically not letting me, you know, step into that frontier that you can see for them, or identify, or just make those moves and have it expand in such a massive way. And that’s where- absolutely there’s work to be done with a clinical professional that would be incredibly supportive, because that’s space that coaching doesn’t really step into.

Hilary Hendershott: Yeah.

Jessica Robson: In like past-based integrations and how to pull, you know, those stories into the present, but not have them dictate your future, kind of thing.

Hilary Hendershott: Yeah. I mean, there’s a set of possibilities we wound up with.

Jessica Robson: Mmhmm.

Hilary Hendershott: And then there’s a set of possibilities we can create as thinking beings.

Jessica Robson: Yeah. Yeah. And in a really like beautiful way, I have this mentor, Suzanne Conrad. And she used to always- in a similar and a parallel kind of discussion, we would talk about, “What are the gifts that our parents gave us, and what are ones that we would want to give back?”

Hilary Hendershott: Mmhmm… Oh, like return, give back, like, “Thank you. But no, thank you.”

Jessica Robson: Yeah. Yeah, and like, you don’t ever have to tell them you’re doing this, by the way.

Hilary Hendershott: Of course. Not necessary. At the Thanksgiving table, “Mom, giving this back. Don’t want this one.”

Jessica Robson: And outside of more deep processing stories that a professional would be able to help with, that could be a conversation of, like, you know, there’s something maybe there about really wanting to honor their family or not be better than or otherwise. And so how could we, you know, honor them and take values that they gave us, or the gifts that our parents gave us, and then also give back the stories that aren’t serving us? And what could that do to give them a little more space to make decisions that could expand their possibilities, informed by what we, as intellectual, individual people are choosing for ourselves versus what past-based stories need to choose or decide for us.

Hilary Hendershott: Let’s round this out by talking about what I think is one of the most stressful situations for people, and that is talking about money with your romantic partner. And I was thinking about this before our conversation, when I was thinking about what to talk about, and I think there are really three big issues. First, we fear bringing it up, right? Because what if they don’t want to talk about it, what if they reject me because I brought it up? What if it’s just super awkward?

Hilary Hendershott: Second, we fear what they’ll think about us, and our financial situation, right, because we measure ourselves by our own numbers.

Hilary Hendershott: And third, I think we really fear knowing the truth about them. Right?

Jessica Robson: Yeah.

Hilary Hendershott: Because most of us do want financial freedom. We want a partner who has some kind of financial security. More assets, less debts, right? And we don’t want to feel materialistic if their financial situation makes us not want to hang out.

Jessica Robson: Mmhmm. Yup.

Hilary Hendershott: I don’t know if you want to talk about how you navigated this. I mean, I know you’re married… I guess what it requires is courage for people to take on, and a willingness to think through frameworks that work for them in their life. But what would you say about that?

Jessica Robson: I mean you said the C word, and courage is, that’s the first thing that came to mind. It is incredibly courageous. Because fear is pervasive. And fear is normally going to be there for most things, most of the time. And being able to meet ourselves in it and choose to have those conversations anyways, is incredibly courageous and incredibly brave.

Jessica Robson: And jumping the void between sitting in the fear of financial conversations with- even if this isn’t like a spouse, but like a partner, someone you’re even just beginning to date; you’re getting to know well enough that there’s a potential future there… To sit with all of those questions. What will they think of me? What will I think of them? Can we alchemize around this? And how would we bring together divergent views? All of those are open ended questions. Right?

Jessica Robson: I think the thing to get moving in the direction of those conversations, are a couple of things. Number one, our own personal values and commitments. And I feel like a broken record talking about that, especially with clients, because the number of times I’m like, well, let’s come back to your values, and let’s come back to the commitments, and what are we making? But that’s the foundation of most of our ability to move through things like fear and things like trepidation. Whatever’s there around a conversation we want to have-

Jessica Robson: Because fear, in those contexts, it’s pointing to something that’s important. Right? And yes, if we think about that part of our brain that’s always scanning for potential danger, and the, you know, social implication between you and that person, of, “But what if they have a problem with my numbers? Or what if I have a problem with theirs?” Our brains are wired for connection, and they’re also wired for collective safety, right? So it threatens our safety inside that dynamic. But, when we come back to our commitments to ourself, our commitments to our financial future. And we can really sit in ownership of those things, and then choose to ask to have the conversation to start, not even get ourselves into what the conversation is going to sound like yet. But even just that first ask is a step in the direction of facing the fear and choosing–exactly–doing it differently. One thing at a time, literally.

Jessica Robson: And then I also like to think of- Mel Robbins has this “let them” theory, that’s really about like, we can’t control what people are going to do. We can only show up. And like I said, when we’re grounded in values and commitments, we can show up with integrity to ourselves. We can be responsible for our thoughts, our actions, our beliefs, all of those things. And what people do with them is theirs. And so inside of that, if we were to ask to have the conversation and we get into it and we’re received, we’ll say, quote unquote negatively, let them receive it negatively. And then ask, is that someone you want to be with?

Hilary Hendershott: Right.

Jessica Robson: I mean, that’s getting into relationship coaching.  But there is that kind of like, can we get rooted enough in what our values and commitments are, and choose to have the conversation anyways, and then see who the person is around money, and see what we do with it.

Hilary Hendershott: I say something semi-frequently–not because I think it comes up so frequently, but because I think it’s so important to give yourself permission–I say, “It is okay to leave someone over money. It is.” Now, I hope people don’t have to do that very frequently, but I mean, we just are terrified that other people are going to think we’re materialistic. If he’s got $300,000 of credit card debt, it’s okay to say goodbye, for now.

Jessica Robson: Mmhmm. Maybe figure it out. And let’s chat later.

Hilary Hendershott: Yeah, right? Like, circle back, circle back. And then your answer to that question just generated an additional question that is related to money, but it’s also not. Why is fear so pervasive?

Jessica Robson: Ah, gosh! Our fear brain is- and I think this is one of those things that comes back to how our brain thinks that it’s protecting us, right? That’s what I was talking about at the beginning, where it’s like, we’re only exposed to so many things in life, and something new, something novel, a threat to our belonging-  all of those different things. It’s our brain’s natural function to try and keep us safe. And in certain situations, it also functions to keep us small. I.e. not having the conversations that are really meaningful to us; not pushing ourselves into our financial possibilities; not stepping into a career possibility because too scary, too much. What does visibility mean? How will people perceive me? All of these thoughts that really take us out of our… power, when it comes down to it.

Jessica Robson: So I think it’s there because it’s a part of our natural wiring, in a way, that we get to–if we see it as an opportunity–come up against and go, “Okay. But what do I actually want? What am I really committed to? And how is this helping me?” A pal of mine, Alex Mazerolle, she’s a yoga teacher, among many other things, and I was on a retreat with her a couple of years ago, and she was talking about thought awareness. And if we really tuned in and listened to the thoughts that are going through our head, which is over 60,000 thoughts a day, we would see how many of them are negative and how many of them are fear based. And this is where–so many of them–and being meticulous about the thoughts we actually let take up mental real estate is annoying, and it’s very subtle work.

Hilary Hendershott: Laborious.

Jessica Robson: Laborious and that literally–from countless podcasts that I’ve listened to, from neurobiologists, and people who study the brain and study habits–that’s our job, like that’s the work if we want to get closer to the things we want, is being way more tuned into what’s going on between our ears and way more responsible for which ones we let take root, which ones we let take up space. And being conscious of our language, conscious of the way we speak to ourselves, conscious of the language that we use to describe our world, all of those things, it all adds up.

Hilary Hendershott: I’ve said before, I really do think wealth building is the final frontier of feminism. And I think this, learning to deal in an adult way with your emotions is the, the spear point of that.

Jessica Robson: Yes.

Hilary Hendershott: That you can’t move forward or make major alterations in what’s possible for you with money until you have a sense of being able to manage the emotions that come with money.

Hilary Hendershott: Thank you so much. Say a little bit about how you work with people, and where can people find out more about you?

Jessica Robson: Yeah, I work one-on-one in groups, with teams. Whether you’re a creative business owner, whether you’re a business leader who has a group or a team behind them. And the work’s really about helping people integrate emotionally, so we can move faster as groups, as teams, and get more done when it comes down to it. If you’re interested in learning more, whether that’s about one-on-one coaching or about group opportunities or keynotes, you can get me at hello@jessicarobson.com, and we can get the conversation started there, or you can meet me over on Instagram, @JessRobson. And if you’re into conversations about feelings, my podcast is “Too Many Feelings, Too Little Time.” And that’s just six episodes in. So we’re new, but having a great time doing it.

Hilary Hendershott: All right. That’s exciting, how cool, to use your voice in that way. Alright, Jess, if your money were loving on you and writing you a thank you note or a love note, what would it be thanking you for?

Jessica Robson: My money would be thanking me for doing the emotional work.

Hilary Hendershott: Yeah.

Jessica Robson: To work with it more thoughtfully, and it would also be thanking me for letting it do a job; for being intentional about where I put it–when, how, and why–and to giving it space to grow.

Hilary Hendershott: I think it would also thank you for closing the browser on the cart when you…

Jessica Robson: That’s what I meant, doing the emotional work to let it actually do some stuff for me! And not just have like… I was never a shoes gal, but it was like, I can’t even tell you the stuff that I bought emotionally. So yeah. Closing the browser. It’s thanking me for closing the browser.

Hilary Hendershott: Nice. Thank you so much for being here.

Jessica Robson: Such a pleasure.