149. Why Success Feels Empty Even When You Feel Like You Have Everything | ft. Jess Ekstrom

Summary

---

Podcast Summary: Call Her Creator with Katelyn Rhoades

Episode 149: Why Success Feels Empty Even When You Feel Like You Have Everything | ft. Jess Ekstrom

Release Date: April 28, 2026
Guest: Jess Ekstrom, author, speaker, entrepreneur

---

Episode Overview

This episode explores the hidden side of achievement for ambitious women: Why does success often feel empty, even when it appears you have “everything”? Host Katelyn Rhoades is joined by Jess Ekstrom—mother, acclaimed speaker, author of Making It Without Losing It, and founder of Headbands of Hope and Mic Drop Workshop—to dive deep into the emotional realities behind female ambition, achievement, identity, and fulfillment in the creator economy.

Together, Jess and Katelyn discuss how childhood wounds, people-pleasing tendencies, and social comparison shape our hunger for more, how to redefine success on our own terms, and practical strategies for building a thriving business without sacrificing your health or sanity.

---

Key Discussion Points & Insights

1. The Illusion of Success as Safety

Timestamps: 01:21 – 06:55

• Safety vs. Satisfaction: Katelyn observes that many ambitious women associate success with safety, believing, “If you make more, do more, become more, then you’ll finally feel okay.”
• Jess shares that achieving visible goals doesn’t necessarily lead to a sense of relief or fulfillment:
  • Quote: “We think once I get this, then I’ll feel like I can relax, or then I’ll feel safe, and that moment never comes.” (Jess Ekstrom, 02:39)
• Mindset Shift: Jess introduces the underdog vs. champion ambition:
  • Underdog ambition: Scrappy, no expectations, room for mistakes (e.g., early startup days).
  • Champion ambition: Shift from “playing to win” to “playing not to lose”—a defensive, pressure-filled mode.
  • Quote: “Your life is going to be a tug of war between beginner and expert...you’re constantly going to be shifting.” (Jess, 05:24)

2. Jess Ekstrom’s Backstory: From Public Scandal to Entrepreneurial Success

Timestamps: 06:55 – 11:15

• Jess recounts how her family was affected by the Bernie Madoff scandal (her mom’s uncle), which shaped her drive to “make something of herself.”
  • Quote: “I’m gonna just do something so good that it’s almost going to cover up this bad, you know?” (Jess, 07:44)
• Launches Headbands of Hope in college, inspired by children with illnesses opting for headbands over wigs. The company’s buy-one-give-one model leads to millions donated and eventual acquisition before she turns 30.
• Despite outward success, Jess struggles with feelings of emptiness and the constant search for the next validation:
  • She introduces the term “false summits” for the achievement highs that don’t satisfy as expected.

3. Therapy & Uncovering the Roots of Ambition

Timestamps: 11:15 – 14:06

• Katelyn and Jess discuss therapy’s role in understanding their “ambition”—often rooted in childhood wounds or a need for validation rather than pure drive.
  • Quote: “The therapist is like, actually, no, that’s not ambition. That’s grief.” (Katelyn, 12:04)
• Both note the importance of asking, “Who am I trying to please?” and confronting the motivations behind achievement.

4. The Purpose Test: Would You Do It Anonymously?

Timestamps: 16:27 – 18:31

• Jess introduces a powerful self-check from her book:
  • Imagine achieving your goal but being required to remain anonymous—would you still pursue it?
  • Quote: “If I got the thing that I’m chasing, but then I had to remain anonymous, would I still do it?” (Jess, 17:27)
• Katelyn admits this question shifts her perspective, revealing how much her goals are tied to others’ recognition.

5. Navigating “Finish-Less” Goals and Embracing the Climb

Timestamps: 18:39 – 22:25

• The conversation turns to the reality that most meaningful achievements in life (raising kids, building a business, self-growth) lack clear finish lines.
• Jess warns against “pickle jar problems”—craving pass/fail validation in areas of life where none exists.
  • Quote: “Most things in our life, most problems that we have aren’t pickle jar problems. They’re more nuanced.” (Jess, 19:30)
• True dopamine hits come during the pursuit, not the achievement.
  • Quote: “We actually don’t get the hit of dopamine at the outcome. We get it in anticipation of the outcome, we get it in the process.” (Jess, 20:50)
• “In the words of Miley Cyrus, it’s the climb.” (Katelyn, 20:42)

6. Decoupling Worth from Outcome & Setting Healthier Boundaries

Timestamps: 22:25 – 29:37

• Jess reflects on growing up in systems with clear progression (grades, report cards) and the resulting void in adulthood.
• She describes her fear that letting go of anxiety about success might mean losing her “edge”—but discovers that embracing presence and loosening her grip makes her a better speaker, mother, and business owner.
  • Quote: “You don’t have to grip it so tightly to get what you want to squeeze the juice out of it.” (Jess, 25:43)
• Katelyn shares her own experience with burnout and stress-induced health challenges, realizing the importance of not sacrificing health and relationships for business goals.
  • Quote: “This is not worth my health...what’s the point of all that if you don’t have someone to celebrate it with or you have bad health?” (Katelyn, 28:45)

7. Focusing on the “Gain,” Not Just the “Cost”

Timestamps: 29:37 – 32:05

• Jess encourages women to assess both what they’re gaining from ambition and what it’s costing them—time, health, sanity.
• She uses a fitness analogy: not desiring the lifestyle required for a “super-jacked” physique; similarly, not everyone should chase the sacrifices that come with “Mel Robbins”–level fame if it’s not aligning with their values or preferred lifestyle.
  • Quote: “I like my unlimited chips and salsa form of business.” (Jess, 31:12)

8. Comparison, Jealousy, & Social Media

Timestamps: 32:05 – 39:03

• Katelyn and Jess discuss the trap of comparing themselves to high-profile entrepreneurs and creators online.
• Jess shares a personal story of unfollowing peers whose success made her feel inadequate, recognizing it as her issue to work on—not theirs.
  • Quote: “Their success was making me feel less, and that was me, not them.” (Jess, 33:25)
• Jess’s “thought interrupter” when feelings of lack or exclusion arise: “Oh, well.”
  • Story: A 70-something woman at a retreat shared this as her mantra for moving on from comparison without overthinking.
  • Quote: “She just recognized the situation for...not what she wanted it to be, and then she was like, ‘Oh, well,’ and then...go about my day.” (Jess, 37:18)

9. Building Sustainable, Aligned Success (vs. Chasing Fame)

Timestamps: 39:47 – 45:44

• Promoting the book: Jess credits building community before needing it (5,000+ core community, 300k email list) as key.
  • Quote: “I am so glad that we built a community before I needed it.” (Jess, 40:55)
• She experiments with tech-driven resources (custom GPT tools drawn only from her book’s content) to meet her audience where they are.
• Jess’s “intern test” for using AI: if she wouldn’t give it to an intern, she won’t delegate it to AI (e.g., ideation and voice stay human).
  • Quote: “That’s a muscle that you have to keep in the gym...if we are like, oh, I just have something that I could skip the gym, then we lose that muscle.” (Jess, 44:14)

---

Notable Quotes & Moments

• On Ambition & Safety:

  • “It’s just a safety thing for me…do you feel more safe when you’re successful?” (Katelyn, 03:30)

• On Childhood Roots:

  • “No, that’s not ambition. That’s grief.” (Katelyn recalling her therapist, 12:04)

• On Comparing Paths:

  • “The world already has a Mel Robbins. What is it that you have to say?” (Jess, 32:28)

• On Social Media Comparison:

  • “I had to unfollow people that I…felt less because of, and that was me, not them.” (Jess, 33:25)
  • “She goes, ‘You know, I do. I walk in the room, I look at everyone, and then I just go, oh well.’” (Jess, recounting story, 37:18)
  • “In a world full of hacks and steps and mental gymnastics, just give me something to cut the mental gymnastics.” (Jess, 39:17)
  • “I love ‘oh well.’ I’m probably going to name this podcast title ‘Oh, Well. Yes.’” (Katelyn, 39:03)

---

Practical Takeaways

• Check Your Motivations: Use Jess’s “purpose test”—would you work towards your goal if no one knew it was you?
• Celebrate the Climb: Find fulfillment in the process, not just outcomes.
• Watch the Cost: Continually consider what your success is costing you (health, time, peace).
• Build Community Early: Don’t wait until you need support—nurture your audience from day one.
• Use Tech Mindfully: Use AI and automation to enhance, not replace, your creative and relational strengths.
• Interrupt Comparison: Adopt a “thought interrupter” like “oh well” when you catch yourself spiraling into jealousy or inadequacy.

---

How to Connect with Jess

• Book: Making It Without Losing It (releasing May 5)
• Website: jessiekstrom.com/makingit
• Mic Drop Workshop: Community for women speakers
• Weekly “Hype” Text: Text HYPE to 704-228-9495 for Monday motivation
• Instagram & Email List: Highly accessible, transparent online presence

---

Podcast Host: Katelyn Rhoades
Guest: Jess Ekstrom
Listen & Learn More: Call Her Creator with Katelyn Rhoades

---

Section Recap with Approximate Timestamps

| Segment | Timestamp | |:--------------------------------------------------|:------------:| | Introduction & episode theme | 01:21 | | Ambition as safety, underdog vs. champion mindset | 03:50–06:55 | | Jess’s entrepreneurial backstory & “false summits”| 06:55–11:15 | | Therapy & childhood roots of ambition | 11:15–14:06 | | The Purpose Test | 16:27–18:31 | | No clear finish lines / “pickle jar problems” | 18:39–22:25 | | Letting go of “grip,” prioritizing health | 25:27–29:37 | | Cost vs. gain, business/life trade-offs | 29:37–32:05 | | Comparison, jealousy, “oh well” mantra | 32:05–39:17 | | Promotion, tech, AI, building community | 39:47–45:44 | | Book launch & wrap up | 45:47–46:29 |

---

For creators, entrepreneurs, and any woman wrestling with the tension of ambition and presence—this episode is a must-listen.

Transcript

[A]

This episode is sponsored by Shopify, Homeserve and Fora Travel.

[B]

Shopify.

[A]

Starting a business sounds exciting until you're actually in it. The website, the products, the emails, it's a lot. That's why I love Shopify. With hundreds of ready to use templates, Shopify helps you build a beautiful online store that matches your brand's style. And HomeServe. Owning a home is amazing until something breaks. And it's never anything small. It's always those expensive, worst timing situations. That's why I love the idea of HomeServ. It's like a subscription for your home, helping cover those unexpected repairs. And plans start at just 4.99amonth. And Fora Travel, are you the one who always plans the trips, hotels, itineraries, all of it? You're basically already a travel advisor. You're just not getting paid yet. With Fora, you can change that. From building your business to protecting your home to even getting paid to plan your next trip. These are the tools that make it all easier. Launch your business with Shopify. Sign up for your $1 per month trial at shopify.com CHC and HomeServe. Protect your home systems at homeserve.com or become a fora advisor at foratravel.com CHC that's F O R A travel.com CHC

[B]

all right, welcome back to another episode of Call Her Creator. I am so excited for today's episode because I'm. We're speaking to my twin flame. I think, like, we're going to talk about some very important topics. And the more I learn about this person, the more I'm just like, oh, my God, am I her? Is she me? And you'll probably feel that same way too, after you hear Jess speak. So this conversation today is for that very specific girl, the one who's doing all the right things, building the business, showing up. She's making money, but it still feels like she just maybe can't turn off or if she slows down, she'll lose it all or everything might fall apart. So I think for a lot of us, success just starts to feel like safety. Like if you make more or do more or become more, then you'll finally feel okay. But Jess is going to show us, like, you'll get there and then you'll be like, wait, why do I still feel like this? So today I get to introduce you to Jess Ekstrom. She's a mother, she's a Forbes top rated speaker. She's been listed inks female founders 500 list. And she just launched her book, which we'll get to talk about. Jess, I'm really excited for this conversation. Welcome.

[C]

Oh, my gosh. Thank you so much. I'm equally such a fan. Twin flames all the way. And when you said, for a lot of us, success feels like safety. That hit so hard, I'm like, can I go back to my editor and put that in the book? Because it's so true. We think that there's going to be, like, something that. Oh, once I get this, then I'll feel like I can relax, or then I'll feel safe, and that moment never comes. So how do we deal with that? So I love that you said that.

[B]

It never freaking comes, never does. Or we think it's coming, and we're like, oh, it's here. And then I'm like, no, it's not leading. It's really bad, too. Like, there's a lot of girls, girlies that listen to this podcast. So I don't mind talking about our cycles, but, like, I'm in that luteal phase right now. And so Sunday, I'm like, all in my heels, and I told my husband,

[C]

I'm like, burn it down.

[B]

Yeah, well, I say that every other week. But I'm like, you know what? I'm not ambitious. I'm just too scared to lose it all. It's just a safety thing for me. And he's like, come on. Like, yes, you are ambitious. I'm like, no, I'm not. It's just. It's a safety. Do you feel like. Do you feel more safe when you're successful?

[C]

It's. It's so interesting because, you know, I talk about this and making it without losing it. I'll tell you a quick story. When I was in high school, I was on the track team, and I. It took me a while to, like, I can say this. You know, we're girls. It took me a while to even own this. But I was the state champion discus thrower, and I thought that that was, like, made me look manly. Cause I could, like, throw something really far now. I'm really proud of it. Cause I have a daughter. I'm like, hell, yeah. Like, throw it. Do it. But I got this. I won the state championship my junior year, and I didn't come back and compete my senior year. And I, like, came up with some excuse. And when I think about that, I was like, I was afraid to lose it, like, because I already got it. And so there's kind of these two different types of ambition that we pull from. We have, like, underdog ambition where we're scrappy and no one's expecting anything of us. We have maybe, like, we're starting a new platform from scratch. We are like a podcasting, but it's just like, our mom listening. And we're. We can just make mistakes. We do. No one is expecting anything of us. We can be scrappy. And the good thing is, is everyone loves an underdog. We love an underdog story. We love Seabiscuit, like, Jamaican bobsled team. But then this other part that we play for him that you're talking about. Caitlyn is a champion, like, motivation, where we go switch from playing to win to playing not to lose. And that is a completely different type of ambition that we pull from of, like, protecting versus gaining. And so I totally feel like that. I feel like when I first started my company, my first company was out of my dorm room in college. I was like, whatever, Slap a headband on a website, sell it. Cool. I made 15 bucks today. And then now that I have all these things surrounding me or what it feels like. Cause I also recognize, like, no one's looking at your shit as much as you think that they are almost like my confidence waivers a bit, because I feel like I'm playing not to lose instead of playing to win. But the reality is, is that if you are an ambitious person, because people, when I give that. When I give a talk, I talk about, like, the underdog versus the champion mindset. And they ask me, which one's better? Like, which one should I play from? And my answer is both. Like, if you're an ambitious person, your life is going to be a tug of war between beginner and expert. Like, you're constantly going to be shifting. Think about how we all feel right now with AI. Like, it's scary. It's. Everyone who was once an expert at something now is, like, basically relearning their industry with this new thing in it. And so instead of saying, like, am I a champion or am I an underdog? Recognize that you're gonna ebb and flow between them, and that's. That's okay.

[B]

I love that. I love that. And speaking of the headbands, I do want you to take us back for a second. So for anyone that's just, you know, tuning in, I always like to start with, like, your story of how you got to where you got. Because there's so many of us women out there that want to build something really cool, and they don't know where to even Start.

[A]

So tell us your story first.

[C]

Yes. Let me think of where I want to begin. So it started when I was in college. I would say I. My family, when I was in high school, went through this pretty public scandal of my mom's uncle. This is like the. The podcast version. I'm like. I'll be. Let me say the real version on here.

[B]

Yeah.

[C]

My mom's uncle is Bernie Madoff, who's, like, the biggest financial fraud in history. He's, like, stole a bunch of money from people. $64 billion, like, with a B. And so we lost all our money. People lost all their money. It was a very public thing that my family experienced. And so I kind of was. It kind of just woke me up a bit of, like, what is life? What do I want to do with this life? So when I got to college, I just wanted to make something of myself, and, if I'm being honest, make something of myself to kind of make my parents happy again. Not that I felt like they. Looking back, they hand. They were. They are awesome. But I was like, I'm gonna just do something so good that's almost gonna cover up this bad, you know? And so it started. I got an internship in Disney World. That Disney internship led to a Make a Wish internship, which. That's when I discovered just this opportunity where I was like, these are. There's so many kids that are losing their hair to chemotherapy, being offered wigs and hats, and wanting to wear headbands. And I just thought it was such a cool gesture of confidence that they wanted to wear headbands instead of covering up their heads. So I started a company called Headbands of Hope. For every headband sold, we donate one to a child with an illness. And, I mean, it was a bumpy road, but eventually went on to donate millions of headbands all over the world. Did headbands for the NBA, the wnba, sold in Kohl's. Just all these, like, really cool things. And just to kind of bring it back here, it was always like, the next thing is going to be the thing that scratches that itch or checks that box or gonna be the reason why I can say I did it. And that company eventually went on to get acquired, you know, right before I was 30, and which was like, you know, kind of when you start a business is almost. It's like, if you were looking for a finish line, that was it, you know, there. And it was this, like. I don't know, just this identity crisis that I went through. And then I just talked to A bunch of different people, no matter where they're at in their careers, whether they're self employed, whether they're working for a company, whether they're just, you know, working parent or stay at home. Mom. Everyone has these, I call them false summits in the book. These, like, things that we think are gonna be the threshold of happiness that just never hits the way we want it to. I'm like, man, if I'm experiencing this, and I bet a lot of other people are, this idea that, like, achievement, we perceive it as less than, like an ambition, as a. Of like a. A place that we haven't arrived yet. And when we're not there yet, there's, like, just never a moment to be proud of who we are or happy in who we are. So making it without losing it came from this quest of, like, can we be ambitious towards the future and fulfilled and happy in the present at the same time? And we can, but it's a very constant, like, rewiring that we have to do.

[B]

Have you been to therapy?

[C]

I have. Can you tell?

[B]

Well, yes and no, but I just hear your words and it's just like, it's so what you're saying to me. I went to therapy for, for some of this stuff, and it. So it's. You are definitely, like, you're nurturing me with your words right here. And I know there's a girl out there too, you know, that's hitting a milestone or making a. You know, maybe they've hit their goal, but then they feel confused when it doesn't feel how they expected it to feel.

[C]

Was there anything that you learned? I want to know from you, was there anything that. That helped you through that, that you learned in therapy?

[B]

Oh, God, I've learned a lot. I think one of the biggest things was I do a lot of things myself, right? And I'm like, oh, I'm just this ambitious, independent woman. And no, the therapist is like, actually, no, that's not ambition. That's grief. And I was like, wait, what? And then she's like, you know, biologically, we are. You. You lean on your parents for the thing. And I grew up the way that I grew up. My parents had me very young. My mom was 17 when she had me, so she was still a child herself. And she. They. My parents weren't the best parents. Luckily, I had really great grandparents. And my mom, we've talked about this. She is apologizing. She's being a better mom now that we're older. But that was very traumatic in my lifetime. And like this through, like, you know, grade school, college, all the things it really. We haven't had a, A relationship really until I got older is when we started to really understand each other. But it, I learned that it. A lot, A lot comes from, you know, your childhood wounds and stuff like that. And I think that's where my success comes from too. Why I, why I strive so hard to build something is one, from Satan. Two, because I'm trying to get that attention, maybe, which when I think about that, I don't, I don't want attention from this stuff. But there is that. You know, I've built this Instagram following. My main goal is visibility, but I think there's something deeper there and I'm still working through that.

[C]

Yeah, and I love that you're even thinking about it because I think, you know, you and I have a very similar story where it was like kind of something happened in childhood that we are using accolades and achievement to cover up. And it doesn't mean that you have to have some, like, traumatic experience. Maybe you do that that is making you maybe be more ambitious or achievement driven. But I think it's important to take a step back and recognize, like, who am I trying to please?

[A]

Okay, I have a question for you. Are you the friend who plans everything when it comes to trips? Like, you're comparing hotels, finding the best spots, building the itinerary, and everyone else just shows up.

[B]

If that's you, you've probably already thought

[A]

like a travel advisor. You just haven't been paid for it yet. And that's exactly what Fora is built for. Fora is a modern travel agency for people who love planning travel and want to turn that into real income. They give you everything you need. The training, the booking tools, and a full community of advisors. So you're not figuring it out alone. And what I love is how simple it actually is. As a Fora advisor, you get access to over 7,000 travel partners, everything from luxury hotels to boutique stays. And you can offer your clients perks like upgrades, resort credits, and late checkout, things most people don't even know how to access. And every time you book a trip, you earn commission. So if you're already the one planning the trips anyways, this is one of those, why am I not doing this moment. Now's the time to turn your love for travel into something that actually pays you back. Become a fora advisor today at foratravel.com CHC that's f o r a travel.com CHC and make sure, you tell them that we sent you. Let me ask you something. Have you ever had an idea for a business but you immediately thought, what if nobody buys? Or what if I don't know what I'm doing? Because I've been there. When I started my business, I didn't have a full team. I didn't have the perfect systems in place. I just had an idea and the willingness to figure it out as I went. And honestly, having a platform like Shopify would have made that process so much easier. Shopify is the commerce platform behind millions of businesses around the world and literally powers 10% of all E commerce in the US so whether you're just getting started or scaling, it grows with you. You can build a beautiful online store with their ready to use templates, use built in AI tools to write product descriptions and content, and even run email and social campaigns all in one place. And one of my favorite parts, that shop pay button, it makes checkout so seamless, which means fewer abandoned carts and more actual sales. So if you've been sitting on an idea or you're ready to take your business seriously, it's time to turn those what ifs into

[B]

with Shopify.

[A]

Sign up for your $1 per month trial today at shopify.com CHC that's shopify.com CHC right now.

[C]

Because if it's like the boy that dumped me, you know, or the parent that didn't show up to my games, or the teacher that said I would never make something of myself and granted for all of those people, there's also amazing teachers and everyone else and recognizing like, oh, when I realized I was trying to be super successful to fill a gap that no one asked me to fill in my family that I could never fill, then it started to shift from, you know, how do I, like fill this bucket? And instead, how do I build something that I like, who I am while I'm building it? And I like what I'm doing, building along the way. And I think one of the big things that I think about when I look at like what I want to go after is I run it through something called the purpose test and I talk about this and making it without losing it. And we can all do it right now on this show. But if you imagine the thing that you're chasing, you know, whatever it is, maybe it's a follower count, maybe it's a, you know, a project, a, a role, whatever it might be. And then imagine that you got it, it's yours, you got the email, you refreshed you got the phone call. But the kicker is that no one knows it's you. You have to remain anonymous. You can't tell your partner, you can't post on LinkedIn and then ask yourself, like, if I got the thing that I'm chasing, but then I had to remain anonymous, would I still do it?

[B]

Oh, my God.

[C]

And for a lot of us, maybe that changes, you know, maybe it's like

[B]

100% changes for me.

[C]

Yeah, it does. It.

[B]

Yeah, it does. Like, because what are we working towards this. I always say I'm doing it for my children so that they can have like, the best life. But, like, if my children didn't and I don't even, you know, it's something else I struggle with, Jess, is I don't know what, do you have a finish?

[A]

Like, not a finish line, but, like,

[B]

do you have a goal? No, I don't either. I don't know what it is.

[C]

I know. And so that, that usually, like, we want, oh, this is the amount of money that I need, or this is the amount of followers that I need or whatever it might be. And most things don't have clear finish lines. In fact, I would argue the best things don't have finish lines. I mean, raising kids, like, creating a culture, like self exploration, there's none of those things have like a clear done. Even though we look for it, you know, and I call them like pickle jar problems. There's, you know, it's very clear when we struggling to open a pickle jar, which I will never ask my husband to help me. I. It's clear whether you do it or you don't. It's like a pass fail, which is really satisfying, you know, when you hear that pickle jar pop. But most things in our life, most problems that we have aren't pickle jar problems. They're more nuanced. Like, how much money do I need? How many Am I like, do I have enough friends? Am I like, healthy enough? And so we have to kind of learn to be comfortable in the nuance of like, not pass, fail. Yes, no, did it, didn't do it. Which means we have to get comfortable, like, in the process of things. Like, maybe getting healthy is more important than just being healthy, like a threshold. Or maybe like growing our business is more important than having a, like, Forbes Inc. Whatever business. And when you look at some of, like, the top people, I don't know, like Caitlin Clark or whoever, it's not because they have had a goal that they, like, wanted to hit, like, one Thing, it's usually because she just, like, loves playing basketball. And I'm not saying that we have to just, like, love every second of it, but I do think in order to be great at something, we do have to find a way to enjoy it.

[B]

In the words of Miley Cyrus, it's the climb.

[C]

It feels so cliche, but it so is. And there's even brain studies about it, like dopamine, you know, the happiness hormone that we're all chasing in our brain, that we want to feel. They studied our brains at Vanderbilt University and showed that, like, we actually don't get the hit of dopamine at the outcome. We get it in anticipation of the outcome, we get it in the process. And that's why so many singular achievements or singular days have such a big letdown afterwards. Like, you hear people that. It's like you get married and it's like you spend so much time focused on the wedding, and then it's like, boom, it's over and you feel kind of shitty or Olympic athletes have talked about this. Michael Phelps, Simone Biles, about, like a depression after the Olympics. Because you, like, spend all this time focused on this one moment. And so my kind of, like, you asked if I have goals, and I think as a company, it's great to have goals so you know that everyone's kind of pointed in the right direction, like measurable goals. But I know that I. If I get too attached to, like, singular moments, outcomes, endorsements, this person, that person need to get, you know, this book is coming out, I need to hit the New York Times or like, any of that, then I'm just basically attached, matching my worth and my happiness to something that I can't control. And that's just not how I want to live.

[B]

So what can we do instead? And is this why you wrote the book? So that you could help women that are, you know, measuring their worth up against their success? Like, is that why you thought to write this book?

[C]

A hundred percent. I mean, you and I could jam on this forever. Because it's like this, I think when we're kids, you go to school and you're told, oh, you completed first grade, you get to go to second grade, second grade, you go to third grade. And you have these check ins of report cards of how well you're doing or where you need work. And you know if you're good enough because you make it to the next round. And then all of a sudden that just goes away and you're like, wait, who's telling me how I'm doing and who's telling me if I'm good enough to advance or if I'm where I'm supposed to be, if I'm learning what I'm supposed to be learning, it all of a sudden dissolves. And so, like, our most formative years are told to, like, we'll know when it's time to advance and we'll know how we're doing, and then that goes away. And it can be like a total mind fuck. Excuse my French, but. So I wrote this book for anyone, but I have a soft spot for women who might feel stuck in that, like, kind of survive in advance. Hamster wheel. And the thing is, is that I think I had this fear that. And I don't know if you've had this fear, but, like, if I'm not anxious, if I'm not constantly, like, worried about what's next, will I lose my edge? Will.

[A]

Okay, real life moment. There is nothing more humbling than owning a home and realizing, oh, I'm responsible for everything. Like, when something breaks, there's no landlord to call. It's just you, Google and a potential $2,000 problem staring you in. And you never know what it's going to be. It could be a water heater going

[B]

out or a burst pipe.

[A]

It's always unexpected and it's always expensive. And the worst part, a lot of those things, the plumbing issues, the H vac breakdowns, they're not always covered by your standard homeowner's insurance. That's where HomeServe comes in. They offer plans that help protect against those kinds of repairs starting at just 4.99amonth. So instead of scrambling to find someone last minute, you can call their 24.7hotline and get connected with a local experienced technician. It's super simple. You just choose a plan that fits your needs and your budget and something on your plane goes wrong. You just call to start the repair process. And honestly, that is a peace of mind for me. If I needed something like this, HomeServe is what I would use. HomeServe has been helping homeowners for over 20 years with a network of 2,600 local experienced contractors and over 4.5 million customers. So if you want to help protect your home systems and your wallet from covered repairs, go to homeserve. Com. Find a plan that's right for you. That's homeserve. Com not available everywhere. Most plans range between 4.99 to 11.99amonth. Your first year terms apply on covered repairs.

[C]

I not Be successful because I felt like, well, my constant anxiety or pulse on the future is what makes me good. You know, like, as a mom, I had, you know, postpartum anxiety. And I'm like, but this is what's keeping my baby alive. Like, I need to constantly be worried. And I've found that, like, this approach to work or whatever it is that you're creating approach to life, you don't have to suffocate it to be successful. Like, you don't have to grip it so tightly to get what you want to squeeze the juice out of it. In fact, when I became a mom, you know, most of my career is public speaking, and I teach other women how to do it. But, like, a lot of my time is spent on stage. And I was listening to this interview recently with. I want to call him Michael Scott, but that's not his name, Steve Carell. And he was. I was like, that's not his real name. Michael Scott. Steve Carell. And he talked about how when he had his kid, like, he was notorious bad at auditions. Like, anytime he'd go on an audition, he was so bad at it. Then when he had a kid, he got really good at auditioning because he had something else that was more important than that. And I kind of. I felt that with speaking, I look at footage before I had kids and after. And I'm not saying you have to have kids to, like, loosen your grip on something, but I recognized what happened when I loosened my grip on an outcome and when I loosened my grip on trying to win everyone over, that I actually got better at it. I had more fun. I was more loose. I could be do more, like, improv crowd work. Because I wasn't like, okay, here is the thing. Here is my script. Here's what I'm gonna say. And I ha. This has to be good. And so I think for any, like, person or woman out there that is just tightly gripping a date on their calendar, a singular moment in achievement. Like, once I then I mindset then making it without losing it is hopefully can get you on the right. Adjust your track.

[B]

Oh, I can't wait to read it. And it's. That really hits me too, because the end of last year, I really started feeling burned out just because I've had my grip so grippy.

[C]

Yeah.

[B]

Even though, again, I can't tell you, I. Maybe I think I have a. A money goal in my mind that I want to hit. Like, I always get so close, and then it. I drop the ball or something, and it's not even dropping the ball, but I'm just not hitting that goal. Um, but for the last five years I have been hustling my ass off to hit that and it's taken a toll on my health. So at the end of last year I was diagnosed with Hashimoto's and this came up with rashes on my skin. It made me very tired. I got shingles twice too.

[A]

During all that.

[C]

I got stress induced shingles too. Yeah, it happens.

[B]

And, and it was at that moment when I was like, holy, this is not worth my health. Like I can't even get out of bed some days and I have two children that need their mom and like, I would much rather do what I love to do but not have such a strong grip on it to where I have to reach that goal. And like, I'm so stuck on that goal and everybody else is just a blur. Like that's just not my main focus anymore. And so at the end of last year, I'm like, I almost went into like my soft girl era, but I'm still my booty off. I do my work every single day. But like today I know I have meetings till about 2 o' clock and then I'm going to log the F off because I need to time with my children. The last two days I've been on my phone doing stuff because we're launching a new offer and things like that. But what's the point of all that if you don't have someone to celebrate it with or you have bad health?

[C]

It's, it's so spot on. Caitlin of focus on the gain and not the cost. It's like, I'm gaining this much money, I'm gaining this much status, I'm gaining this. But what is it costing me? And is it costing me time? Is it costing me health? Is it costing me sanity? You know, and I think that there's so much talk around success without talking about the cost. There was this like fitness influencer that I follow and you know, he was talking about how like you see these super jacked people on like TikTok and Instagram and six pack abs and he's like, and they're doing like, all you have to do is like five push ups a day and you know, 30 pull ups and like, this is how I maintain. And he's like, the life that they live is maybe not like worth it to you to get that physique, get that like body. Like they're not having like unlimited chips and salsa at like, you know, taco Tuesday, and I'm like, yeah, I like my unlimited chips and salsa. I like eating the rest of my kids peanut butter and jelly even though I just ate my own lunch. Like, I like not freaking out about that stuff. So I am okay with the physique that I have and it's, it's the same thing when it comes to like work and business. You know, I can, I've seen the bigs up close. Like, not like super up close, but like Brene Brown or you know, Simon Sinek and Mel Robbins. And I'm like, holy cow. I respect mad respect the hustle, but I'm wouldn't trade the lifestyle. So I am good with like my 10, 20, 30%, maybe year over year growth. It's not this like hockey stick, can't believe Cinderella story, but the lifestyle that I live where I'm like done at three. I'm picking and choosing what speaking I want to do so I'm not on a plane every week like I was five years ago. I'm okay with that. I'm okay with the chips and salsa unlimited form of business where I'm like, the cost is too much for me right now to be that.

[B]

That's. And that's what I came to the understanding of too, because Mel Robbins. Were you saying her? That's like, that was a goal I thought I wanted. I thought I wanted Robbins status, a podcast. And then I'm like, wait, that means. Let's really look back on, think about what that means. Yeah, do. She can't just go into Target and go shopping probably. Like, actually I don't want that.

[C]

And also the world already has a Mel Robbins. And so something that I like talk about in Mic Drop workshop is like a lot of people say, well, I just want to be like the next Mel, the next Brene, the next Rachel hall is like, whatever it might be. And I'm like, those people already exist. And so what is it that like, you have to say that you're doing and you could do it in a way that they're not. I mean, Mel has her own playbook and maybe Caitlin has a different one. And it could mean that you reach a level of success that you really like without the expense of your peace or your health. And I think in, you know, obviously I'm on every platform. You know, this like show is Color Creator. There's a lot of people that are online and it is so easy to just like start painting your version of success because you see someone else's. It's like, well, I Should vacation with my family in Europe for six months or I should be further along because this person is. And I am. I one time got in, like, a. Not an argument, but it was like a damaged relationship because I was so in my head about what other people were doing that I just had to unfollow people that I. That were for no fault of theirs. Their success was making me feel less, and that was me, not them. And then one of them had something that showed them where they were unfollowed. I was like, I didn't even know that was a thing where people could see that you unfollow them. And she reached out to me, like, why'd you unfollow me? I was like, oh, my gosh. I didn't like. And I just had to be honest. I was like, you're crushing it. And that's awesome. I'm just in a spot. This was like 10 or so years ago. I'm just in a spot where that makes me feel really insecure and I'm working on it. And now I do feel like I'm in a point where I can be genuinely excited for other people and they're. I've built a whole business off of creating my own competitors in my space. Like, I want to see other women speaking and being on stages, but you have to get so comfortable in your own abilities and knowing that you have a unique way to get there. Like, you have an individual path that's gonna be different than their path, because otherwise it feels like there is just one track and one person and one way that's gonna get there. And if they took it, then it's gone, which just isn't the case.

[B]

Not the case. I would actually like for you to break that down a little bit more nitty gritty, too, because just this weekend, you probably saw it too, on Instagram. There was a bunch of the bigger girls together, like Amy Porterfield, Maria went. Jen Gottlieb. Did you see they were all together? It was like this eight figure business owner.

[C]

Okay, yeah, probably. Yeah, I probably saw it. Yeah.

[B]

I caught myself being, like, feeling jealous. And I'm like. Like that. First of all, stay in your lane, Caitlin. Like, they've. They've built incredible businesses. But what for someone that does that? I know I'm not the only woman that does that. What are some real life things that I could do, Jess, that make me step back and. And not get in that mindset? Like, do you have any, like, strategies for someone like me when that happens?

[C]

I do. And I've felt it before, too. And it's. It's not even like watching the, like all the. The big people get together. It goes back to just like, I remember as a kid being, you know, at school and hearing about a birthday party the past weekend that, you know, I wasn't invited to. Or like, we all have these moments where you're like, oh, that sucks. You know, like, I wasn't there. So there's this part of the book I'll tell. I'll share a story first and then I'll give you the framework. But I went to this retreat for women and who are, like, business owners. And everyone there was like, in their 30s, maybe 40s. And then I saw this woman there who was probably late 70s, early 80s, and I was like, wow, what a baller move to, like, come to this retreat. And so I'm talking to her, and I don't know what came over me. It was so rude. But we. In the moment, it worked. But this question sounds super rude. I said to her, I was like, do you ever get self conscious showing up to these things? The age that you are versus the age everyone else is? She goes, you know, I do. I walk in the room, I look at everyone, and then I just go, oh, well. And then I just go about my day. And I was like, like, what a power move. She didn't have a running pros and cons list. She didn't try to push herself into the positive. She. She just recognized the situation for, like, not what she wanted it to be. And then she was like, two words, oh, well. And then like, it's almost like I think sometimes when I try to say, like, you shouldn't feel worried about this, like, it's okay, other people can have friends. And it almost is just putting kerosene on a fire that already exists when I try to make sense of it. And so finding, like, a thought interrupter for you that allows you to validate the feeling of being left out without attaching to it. And even better yet, not making a supplemental narrative of, like, well, they probably are all talking about, like, you know, this or that. And so I've found myself in so many scenarios being like, I wish that a gig that I applied for. And then I see that who they selected and it wasn't me. And I'm just like, you know, I could say, well, what does she have that I don't? Or what were they looking for that I didn't have? And instead I'm just like, oh, well, and go about my Day. And so. And I'm not perfect at that. Of course I have to work at it, but I would just say, like, don't even try to make sense of it and don't give it more airtime and find your phrase, maybe it's like, you know, that sucks, whatever it might be, and have that be your thought interrupter so you can recognize the feeling for what it is, which feels kind of shitty, but then move along into something else and not give it more space.

[B]

I love ol And I'm probably gonna name this podcast title. Oh, well, yes. Like, you know what I mean? That is so good. It's so dumb because we all say it, but it's like, that's. That's mind blowing, actually.

[C]

It really is. It's like the simplest thing and in a world full of, like, hacks and steps and mental gymnastics, I'm like, just give me something to cut the mental gymnastics. And I told her, I was like, you should write a book called, oh, well, like that. I would read it in a second, but it could just be one page because it's so simple.

[B]

Yes. Oh, my God, I love that so much. That's just. That's my new phrase. So thank you for that.

[C]

Yeah.

[B]

Okay. You're amazing. I love this conversation. Me too. Talk to us. When does the book launch?

[A]

For? Sure.

[B]

Like I. I heard you saying upcoming,

[C]

May 5 is when it comes out. So you guys are listening to this potentially before it comes out. And so if you go on my website, JesseXtrom.com making it, there's some fun pre order perks that you can be a part of to get it early.

[B]

I love this. And Ken, from a creator point of view, because I have a lot of ambitious creators that listen to this podcast. What are you doing to promote this book? Like, if someone has an offer out, there might not be a book. It might be a digital course or their first PDF guide. Tell us some of the things that you're doing to get your book out there.

[C]

Okay. This is such a great question. And I would say in a world of like, digital information, which we is awesome. And that's like our bread and butter, what we do at Mike Drop Workshop is delivering digital information. One of the things I am so glad that we accidentally did years ago in 2018, when I started Mic Drop, was we built a community, a community of women speakers that has grown exponentially. We have around like 5,000, you know, women in that close community. But then our email list for all the free programs and things that we do is like, almost 300,000 women on our email list. And I am so glad that I built a community before I needed it. And so if you're thinking about, like, that you might have a book or a podcast or something that you eventually want to launch. Before I think about, like, how do I push it? I would think about how do I, like, bring people together in a way that's delivering value without asking something big of them first. Maybe it's like a, you know, free boot camp or a training or. And it doesn't always have to be free. But I'm just like, man, I am so glad that we've built a community before I had stuff to deliver to it. So I would say that. And then the other things that I did that could be interesting for creators on here is, you know, I'm someone. My attention span is so short, just like everyone else, and it's getting worse by the second. And so I'm like, if I am not super excited to sit down and read a book from start to finish, maybe not a ton of other people are. So I created a. And I hope the book is entertaining enough to where you want to. But just in case, I created a custom GPT called your success Fingerprint Coach. And there's this part of the book where it helps you figure out, like, how did you define success in your childhood, like we were talking about at the beginning of this show? And how do you want to define it going forward in this, like, season of your life? And it breaks it down into steps, boundaries, what you want your day to look like, and things like that. And so I made it into a custom GPT, which was super easy to do. And it's not sourcing from anywhere on the Internet except for the book. And so people can use it as, like, a pocket coach when they buy the book. I found that. That and just meeting people where they are, which might not be sitting in a field reading a book is helpful in just the marketing of, like, just basic expectations. I'm like, yeah, I get it. Life is hard. So here's a different resource if that's helpful for. For you. So maybe creating an AI tool that's like a companion. I don't necessarily want a full AI product that replaces what we're doing, but even in our course, we have. We call him Mike. It's like our assistant. And if you're looking for something that you can't find, Mike only feeds from the IP that we give it. If you're looking for, like, a contract or, like, oh, I just the event came back and they said this and they want that. What do I say? It pulls from our own ip. And so it's supplemental to the course, but not in replacement of it. So I would maybe play around with building an AI tool.

[B]

I love that. Okay, so.

[C]

And I'm like, the least techie person ever. And the great part is you can just ask AI how to build it and it'll tell you.

[B]

Isn't that wild? I love it. I love it and hate it. Right, Right.

[C]

I know.

[B]

Cool.

[C]

So I did see someone post the other day, if they wouldn't give the task to an intern, they're not giving it to AI. And it. That has been a good guardrail for me because as a someone who's a creator and creative, it's like, that's a muscle that you have to keep in the gym. And if we are like, oh, well, I just have, you know, something that I could skip the gym, it's like, then we lose that muscle. And so I wouldn't ask, like, an internal to, like, share my thoughts or opinions or ideas, create my own thoughts or opinions. I might ask them to proof it. I might ask them to research something for me, but I'm not asking them to create my ideas. And so that's been a good, like, quick test before I open up a AI source.

[B]

I love that. That is super, super helpful. Thank you. Ah, this was so good. Very good conversation. I loved this. Thank you so much for coming on.

[C]

Thank you, Caitlin. And I've been following you, and you are just. It just goes to show, like, stuff that you're telling me. I'm like, you just never know what people are going through behind the scenes. And just because, of course, on my lens, I'm like, oh, my gosh, she's got it all figured out. She doesn't have a problem in the world, and she's just crushing it. And you are. But it's like, oh, everyone has their own path, their own journey. And I appreciate you being transparent about it because that's just helpful for everyone else. Else. So thank you.

[B]

I will always be. Thank you so much. And how can people connect with you?

[C]

Yes, I'm not hard to find. I'm very available on the Internet. You can buy making it without losing it wherever, like, books are sold. I love local, so if you can ask your local bookstore, that'd be great. And then I do send out a text every Monday with, like a hype text or a quote, a question, something to chew on throughout the week. I send it at 11am Eastern. So you can text me the word hype to 704-228-9495, and you'll get that every Monday at 11.

[B]

I love that. Okay.

[C]

It's my favorite thing I do. Yeah.

[B]

Ah. I'm gonna sign up right now. Awesome. Okay. Well, this was amazing. I really, genuinely. I love your story. I love everything that you're doing, and I can't wait to read your book, so thank you.

[C]

Thanks, Caitlyn. You're the best.