Stop Waiting to Feel Happy: The Mindset Shift Every Ambitious Person Needs | Jess Ekstrom - EP 796

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1:11Visit joinmidi.com. Specialist-led care, virtual visits, insurance eligible. Midlife needs Midi. Results may vary. Medications prescribed only if clinically appropriate based on a consultation with a clinician. Insurance coverage varies. Check with your plan for coverage. Coming up next on PassionStruck. There was this interesting study at Vanderbilt that looked at dopamine. Dopamine is honestly the feeling that we're all chasing. It's the feel-good hormone, that happiness chemical that we get when we call a friend or eat a good piece of cake or something. And we're looking for that feeling. And this study at Vanderbilt thought that we got that dopamine hit at the result.

1:49when we get the raise, when we hit a certain number or promotion. But this study showed that we were wrong. We actually, it studied our brains and we get that hit of dopamine in anticipation of the results, not the result itself. Welcome to Passion Struck. I'm your host, John Miles. This is the show where we explore the art of human flourishing and what it truly means to live like it matters. Each week, I sit down with changemakers, creators, scientists, and everyday heroes to decode the human experience and uncover the tools that help us lead with meaning, heal what hurts, and pursue the fullest expression of who we're capable of becoming.

2:30Whether you're designing your future, developing as a leader, or seeking deeper alignment in your life, this show is your invitation to grow with purpose and act with intention. Because the secret to a life of deep purpose, connection, and impact is choosing to live like you matter.

2:53Hey, it's your friend, John, and welcome back to episode 796 of the PassionStruck podcast. I want to ask you a question. Have you ever achieved something you worked incredibly hard for only to discover that the feeling didn't last nearly as long as you thought it would? Maybe it was a promotion, launching a business, publishing a book, reaching a financial goal. For a moment, it felt incredible. And then your attention quietly shifted to the next mountain. If you've ever wondered why that happens, today's conversation is for you. Because I think many of us have been taught to believe that purpose is something we discover somewhere out there in the future.

3:36What if purpose isn't waiting to be found? What if it's something we create? That's the question we're exploring this week as we continue our series on flourishing, how humans become fully alive. Over the past three weeks, we've explored why flourishing begins with presence, why lasting change requires us to rewire familiar patterns of thinking, and how the environments around us quietly shape who we're becoming. Today, we reach another turning point. Because flourishing doesn't stop with personal growth, it naturally expands into contribution. And contribution begins when we stop asking, how can I become more successful?

4:16And start asking, how can I create something that genuinely improves another person's life? Today's guest, Jess Ekstrom, has spent her career wrestling with exactly that question. Jess is a bestselling author, entrepreneur, founder of Headbands of Hope and mic drop workshop, and one of today's most thoughtful voices on ambition and purpose. In this conversation, she challenges the idea that purpose is a destination and offers a far more liberating perspective, one that has stayed with me ever since we recorded this interview. You'll learn why the arrival mindset keeps so many high achievers from enjoying the lives they're building, how contribution reshapes our relationship with success, and why purpose is often created through small, consistent acts of service rather than one defining moment.

5:05I think this conversation will change the way you think about ambition. More importantly, I think it will change the way you think about your own life. So let's dive in. Here's my conversation with Jess Siegstrom. Thank you for choosing PassionStruck and choosing me to be your host and guide on your journey to creating an intentional life that matters. Now, let that journey begin.

5:30I am absolutely thrilled today to welcome Jess Ekstrom on PassionStruck. Jess, how are you today? I'm good, John. Thanks for having me. I am so excited to have you. You are such a phenomenal keynote speaker. Your TED Talk is incredible. And I am so excited to talk about your new book, Making It Without Losing It. What an amazing title. We are all losing it in some way, shape, or form. So maybe that means we can all make it too. Jess, I know we all have defining moments and they come in many shapes and forms. Some of them are highlights. Some of them are lowlights. I understand you had a defining moment years ago that involved a tiara.

6:14I was hoping you might educate us on that story. Oh man, John, this one cuts deep. I was doing an internship for the Make-A-Wish Foundation and I was doing a lot of behind the scenes work. Interns are notorious for doing the busy things. I was doing exactly that. I was organizing supply closets, filling coffee for people, cold calling people for donations and getting hung up on. But it was truly the first time in my life where I realized it wasn't about what I was doing because I was so clearly connected to why I was doing it. Every single thing I did, no matter how boring or tedious it might have seemed on paper, I could connect the dots.

7:01I could draw a straight line to helping make a wish come true for a kid. And so it was towards the end of this internship, my boss decided she was going to give me a little bit more responsibility to round out my summer before I went back to school at NC State. And she assigned me a wish child and I got to be the coordinator of her wish and really make her wish come together. I was reading her file. Her name's Renee. She's four years old. She wanted to go to Disney, but specifically she wanted to go to Disney to meet Sleeping Beauty. And I started planning her wish, calling the parks, making sure Sleeping Beauty could be there for all of her meals.

7:39And then about a week before she was scheduled to go to Disney, she had some symptoms flare up, wasn't feeling well. They sent her to the hospital, had done some scans and realized that there was something they had missed in their previous scans and her cancer had started to return. And they said that she was not going to be in good enough condition the following week to fly or drive to Disney. And they had to cancel her wish. And I remember being in the office that day and just thinking this can't be the story because we have experiences in our life that we can't control. We can't control the weather.

8:24We can't control our flight, but our stories are things that we can control. It's how we react, respond what we do with our experiences. And so I couldn't make her better. I couldn't get her to Disney world, but maybe I could rewrite the story. So I went on to Google, looked up local costume shops in Charlotte, North Carolina, where we were. And then a few hours later arrived on her doorstep with a tiara dressed as sleeping beauty and spent the whole day with her. Yeah, it makes me emotional every time I talk about it. But I spent the whole day with her and her family as Sleeping Beauty and character and tried to make her wish come true that day.

9:06And years later, I can pinpoint that as the biggest before and after moment of my life. And that's an incredible story. When my kids were young, each of them for a prolonged period of time went into character. My son for almost two years was Peter Pan. every single day. We created this Peter Pan custom costume for him, and we had to make three or four of them because he would not take it off. I love that you all just embraced it too, didn't try to change him. My daughter is that way, right? My three-year-old is that way with Elsa from Frozen. She is all in, and you just got to ride it out. Let kids become who they are.

9:47My daughter wanted to be Dorothy. She had that blue. Classic, an old soul. I love that. Yeah. Yes, I love it. I have a North Carolina State story for you. Do you really? My Wolfpack? It's ancillary, but Red Hat was located on the campus of NC State. So I was a senior executive at Lowe's and I get this call that Red Hat wants me to be their CIO. So I go and I do this whole interview and my ego got the best of me because at that time I was interviewing for these big fortune 50 CIO jobs. And I'm like, why would I go to this puny startup company? And I'm meeting the CEO. I ended up not taking the job because I didn't think it was a big enough job for me.

10:37And fast forward two, three years later, my first cousin is a freshman at Duke and his roommate is the CEO's son. So I happen to be up there visiting and I run into the CEO again and he goes, you are such an idiot. I'm like, well, I love the company. I love this, et cetera. But I just didn't think that this was the career job for me. He goes, I was hiring you to be my replacement because my daughter had a health crisis and I knew I was leaving and I needed someplace to park you. So it wasn't obvious that you were going to be my successor. And all the color of my whole body just vanished. And I look back now and it changed everything for me because sometimes you have to look beyond what you're initially walking into and see the opportunity beyond it.

11:36I wish he would have shared that with me at the time. I ended up going on to becoming a CIO at Dell and everything turned out great. But in retrospect, that would have obviously been the better career choice. It's making me think, John, I appreciate you saying that. I just gave a commencement address last Friday at my high school and I was thinking about - How cool is that? It was very cool. It was the favorite speaking opportunity I've ever had. But one of the points that I tried to make was that there are multiple winning scenarios for your career. And a lot of them you don't even know exist yet.

12:15They haven't even a role that you're going to have a whole career in. Maybe hasn't even been invented or created yet. And I think so many times we can tell ourselves there's a right and a wrong. There's the job I should have had, the job, the company I was supposed to start. And instead it's like make any decision, the right decision. Of course, being CIO, going to CEO of Red Hat would have been a great decision, but also maybe wouldn't have done this podcast. Maybe there's so many other things that wouldn't have happened. And so I used to just have so much guilt and hindsight of, well, what did it have been better if I had done this or that?

12:58And I'm like, I'm just going to make any decision. I make the right decision. And I love that. And you can't look back. Although I would have loved to have you in Raleigh. Let's just say that. I would have loved to been there. The more time I have spent in RTP, the better. I love it. And yeah, it's very cool place. And I love living in North Carolina because you got the four seasons, but you also got the mountains and you got the beach not too far away. Got a lot of college sports. Right now, the hurricanes are on a, it's going really well. It's a fun place to live. Absolutely. Well, let's talk about the book, Jess.

13:36You open up the book with this idea that smash is better than cash. Words I didn't think were going to come out of your mouth today. the important thing here is I focus a lot on this show about so many of us are focused on achievement and we realize that when we achieve the things we thought we always wanted the emotional payoff isn't what we expected and that's really what's behind this whole phrase can you go into how you came up with it yes please let me give context we can get people's minds out of the gutter my journey in this that as far as early as I can remember was a piggy bank And I think every single one of us probably had a piggy bank or are familiar with it.

14:20And I remember the thrill I would get from finding quarters in the couch or doing lemonade stands and hearing that clink into that piggy bank. And then I remember one day I tried to fit a quarter in and it wouldn't fit. And so now I say my piggy bank was ready to IPO. I was like, you're ready to smash it. And smashing the piggy bank, counting the change. I think it over a year, it got to maybe$12 and my mom let me get all my coins, put them in plastic bags. We went to the dollar store to cash out and on the way home from the dollar store and I had my things that I bought, I just kept thinking the smash was better than the cash.

15:04Doing, getting to the point was better than the outcome was better than the point. And it was just the first taste of that when I was a kid of maybe I enjoyed the process rather than more than the results. And then that just became more and more apparent as I started two multimillion dollar companies before the age I was 30. I kept thinking that, well, this next thing is going to be the thing that makes me feel successful or makes me feel fulfilled. And then a tale as old as time, we move, we extend the progress bar, we move the goal post. And so this book, Making It Without Losing It, really started from this idea of can ambition towards the future and fulfillment in the present exist at the same time?

15:54Because we usually believe that success and burnout are a package deal. Success has to be hard. You have to run yourself into the ground. You have to be a little bit burnt or crazy in order to make it work. and my answer is no, we can do both at once. But if we keep thinking that the next thing on our to-do list or achievement or milestone is going to fill some need or fill some gap, then it's this endless cycle that never stops. I love this topic because it's one that I've had now two conversations with Arthur Brooks about. And it's something that he is really fixated on because it's a trap of so many people and you call it the arrival trap.

16:43How do you define that? Because I love the concept. The arrival trap is a mindset that our success is around the corner, that we have to arrive somewhere in order to feel the thing that we want to feel. And there was this interesting study at Vanderbilt that looked at dopamine. Dopamine is honestly the feeling that we're all chasing. It's the feel good hormone, that happiness chemical that we get when we call a friend or eat a good piece of cake or something. And we're looking for that feeling. And the study at Vanderbilt thought that we got that dopamine hit at the result, when we get the raise, when we hit a certain number promotion.

17:24But this study showed that we were wrong. We actually, it studied our brains and we get that hit of dopamine in anticipation of the results, not the result itself. And so this arrival trap is this belief that we all have that I like to call it the once I, then I, we've all said that to ourselves. Well, once I can just get through this month, then I can finally relax. Once I can make this amount of money, then I'll finally feel safe. Once I can live in this neighborhood, then I fill in the blank here. And one side then I trains us to delay joy and fulfillment to the thing around the corner. And we all know that it never truly feels the way we want it to feel.

18:09And so instead of having this arrival trap, have the arrived mindset, realize that I can still be ambitious towards the future and content with where I am. The thing that I I think we all as ambitious people, which I have to believe if you're listening to PassionStruck, you're probably an ambitious person. We will always have a gap between where we're standing now and where we want to go. That's just the nature of ambition to have goals and dreams and things that we haven't accomplished yet. But the thing is that we have two different ways that we can look at that gap. That gap can be disappointing.

18:49It can be discouraging. It can be, oh, look at what I haven't accomplished yet. It can feel like an absence, a net loss between where you're at and where you want to go, which is where a lot of us live and where I lived for a while. Or the other way we can look at that ambition gap is excitement, curiosity. Just like we were talking about this endless winning scenario of maybe I work at Red Hat, maybe I work here. I wonder how the chips are going to fall. I wonder what it would look like if I did this. And it's more of a sandbox, a playground, an experimental phase. So making it without losing it, what I've been trying to do with myself is see this gap between where I'm at now and where I want to go, not as a discouraging absence, but as an exciting opportunity.

19:39One of the things I talk about, Jess, a lot, and I'm going to bridge this to what you were just talking about, is that so many people today, I think, feel something is absolutely missing in their lives. And a lot of them can't put their finger on it because they're like, I'm doing everything that I think I should be doing to feel like I belong, yet I don't. How much do you attribute that arrival trap to more and more people feeling like they don't matter? That's such a good point. And I'm really glad you said that. I think a lot of people are like, is this it? Am I where I'm at now? Am I supposed to be here?

20:25Because when you think about it, our brains were trained to know where we fall. We went to school. We know, okay, I've made it through first grade. It's good enough to go to second grade. Here's how I'm doing. The teacher gives you a score. And you go through life in these early formative years with a scale and with a knowing of I'm good enough, I can advance, and here's how I'm being graded. And then you go into a life. No one's giving you a grade. You're not sure if this is where you're supposed to be. And you're like, what's the wifi password? Everyone feels like they know what they're doing, yet I'm still here.

21:07And so I would say that this arrival trap can be one of two things, a mindset of a hamster wheel where you're chasing what's next and not realizing that you're in it right now. This is what it is. You get your dopamine in the process, not at the result. But it can also be another thing that I find a lot that I'm curious, John, you speak at a lot of companies and do a lot of speaking like me. And I find it's more of a purpose trap where people believe, this might be controversial what I'm about to say, but I think that finding your purpose is terrible advice because it makes people believe that there is something out there that is their purpose that they don't know yet.

21:57There's a secret, there's a role, a job, a company that they just haven't found yet. When instead I see so many people that have the ability to create purpose in their role or their job, whatever it is right now at this very moment. And so I think sometimes they're either, this isn't my purpose. I need to go find it instead of looking at like, how do I create it in this moment? And when I speak at companies, I go through the process of changing our mindset from I'm selling blank product to I'm serving blank person. Because when you're just focused on selling a product, it can feel very purposeless.

22:45But if you can connect, here's my job, here's my roles, here are the tasks that I do every day to a human on the other end of it, then it changes from I'm selling blank to I'm serving blank. So I think that missing feeling that we have could be the hamster wheel, but it can also be this notion of that purpose is found when truly I think purpose is built. I don't know how you feel about that. We'll be right back with more of my conversation with Jess. If today's discussion is resonating with you, I want to invite you to continue it beyond the podcast. Every episode in our flourishing series includes a companion workbook filled with reflection questions, journal prompts, and practical exercises to help you turn these conversations into meaningful change.

23:34I also publish weekly companion essays inside my substack, The Ignited Life, where we explore these ideas in even greater depth. And as many of you know, I've also been working on my next book, The Mattering Effect, which will be released this October. While Passion Struck explored intentional living, The Mattering Effect asks a deeper question. What happens when people feel invisible in their lives? Throughout this year, I'll be sharing exclusive behind-the-scenes insights, research, and early ideas from the book with the Ignited Life community. You can access this week's workbook, subscribe to the Ignited Life, and learn more about the mattering fact using the links in today's show notes.

24:15Now, a quick break for our sponsors. Thank you for supporting those who support the show.

24:31you're listening to passion struck right here on the passion struck network now let's get back to my conversation with jess ekstrom there's this interview that i did jess a number of years ago and i always refer to it because there was a moment and i was talking to this gentleman andreas Widmer. And Andreas is the head of the business school at, I think it's a Catholic university in DC. And he was 18, 19 years old, grew up in Switzerland and had no idea what to do with his life. So on a whim, he applies for the Swiss guard, doesn't think he has a chance. Before long, he's a Swiss guard at the Vatican.

25:15And before long after that, Pope John Paul II is his personal mentor. And he told me that he would be sitting there with the Pope. And even though he has all these obligations, all these commitments, he felt like the world evaporated when he was with his holiness. And it was just the two of them in presence. And he would always tell Andreas that each one of us has a set of superpowers that we're born with and our purpose in life is to figure out how do you align those superpowers with a problem that you see that the world needs solving because he said that your inherent gift to this world is using your gifts that are inherent to you to solve a problem bigger than you and so to me that's what our purpose wayfinding mission is how do you take your super abilities that only you possess and use them to serve humanity?

26:18And to me, once you do that, and you go down that path, because I think passion and purpose are two different things. It's you become so aligned with that goal, you feel so alive inside, that you're willing to pursue it with all that you have because it makes you feel truly alive inside. And that's when you reach a state of becoming passion struck is the terminology that I like to use. But if you're constantly just sitting there searching for a purpose, purpose, I think you need to go about it a different way. I think you need to figure out what is the problem that you're called to solve? How can you solve it uniquely?

27:00And then who are you supposed to be helping? And I think when those things align, that's when it comes together. It reminds me. So before I was at Make-A-Wish, I interned in Disney World and I was a PhotoPass photographer, but some of my friends were custodians. And I remember having this moment where I talked to two custodians. One of them absolutely hated their job and the other person loved it. And they had the same role, same job description, same tasks. And the one who was not happy in their job was like, I have a college degree. I am picking up trash from people. I am scraping gum off of the benches.

27:49What am I doing with my life? And then the other custodian who, again, same role, same job description, loved his job. He was like, I get to be in the moments where people are walking into the park, looking for directions. I get to tell them what my favorite rides are. I get to create magical moments and hand out a fast pass to someone who it's their first time. I get to make sure that people have the best experience by making sure the streets are clean. And so it's this notion of switching the I have to's to I get to's. And exactly what you were saying, John, about using your talents and the things that make you unique in the moment that you're at.