How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom

Summary

Podcast Summary: Creating Confidence with Heather Monahan

Episode: How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom
Date: April 21, 2026

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Overview

In this uplifting and insightful episode, Heather Monahan sits down with repeat guest Jess Ekstrom—entrepreneur, bestselling author, and an advocate for women’s voices—to dig deep into what it really means to “make it” without losing yourself along the way. Together, they explore the dangers of delaying happiness until after achieving ambitious goals, how to embrace joy in the process, and the importance of re-examining our definitions of success. Jess shares powerful strategies from her new book Making It Without Losing It, and both women share personal stories about period of change, chasing purpose, and finding fulfillment both in business and at home.

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Key Discussion Points & Insights

Building Social Capital and Asking for Help

• Lead with Generosity:
  Jess and Heather discuss the importance of helping others and leading with generosity when building relationships, rather than only reaching out when you need something.

  • Memorable Quote (03:03, Jess):
    "You don't talk the talk, you walk the walk. A lot of people are quick to give encouragement, and not a lot are quick to give opportunity. You're so willing and generous with giving opportunity."

• Do Your Homework When Asking:
  Jess emphasizes the importance of showing you've done your research before asking for favors or introductions, making it a partnership rather than a transaction.

  • Notable Practice (09:24, Heather):
    “Before you ask someone for something, do the homework. ...I'll write up three different options of potential [endorsement] just to make it easy for them.”

Transforming Ambition & Scaling Up

• Chasing Purpose over Titles:
  Jess shares her journey from founding Headbands of Hope in college—donating millions of headbands to children with illnesses—to launching Mic Drop Workshop, supporting women to become professional speakers.

  • Story Highlight (17:34, Jess):
    “Headbands of Hope went on to get acquired during the pandemic... I didn't realize how emotional that was for me. Saying goodbye to something you built.”

• The Post-Achievement Letdown:
  Both discuss how achieving long-held goals brings a relief, but often not the permanent happiness expected. Jess calls this the “post achievement letdown” and explains its prevalence—even among Olympians (32:34).

Redefining Success & Enjoying the Journey

• Personalizing Your Success 'Fingerprint':
  Jess introduces the concept of a "success fingerprint": realizing success is individually defined and evolves with life’s seasons.

  • Memorable Exercise (22:13, Jess):
    “Success is redefined by each person in each season. ... Audit what you’re chasing. Would you still want it if no one knew it was you? If yes, it’s in your fingerprint.”

• Avoiding the Delay of Joy:
  Both speakers challenge the idea that happiness comes only after a goal is reached, emphasizing the need to enjoy the process.

  • Quote from Jess (12:01; repeated at 49:19):
    “Don’t try to achieve things, to have zero problems. Do things that have problems you’re excited to solve.”

Practical Strategies for the Process

• Making Asks into Offers:
  Instead of asking “Can I speak at your event?” say “Would my session on [X] be helpful for your audience?”—framing your approach as adding value.

• Zooming Out for Perspective:
  Jess shares a visualization exercise from a silent retreat: viewing your daily life from above to ask, “Do I like the dots I’m painting on the canvas?” (41:15) This helps realign daily actions with your deeper values.

Handling Life’s Uncertainties

• Embracing Uncertainty:
  Heather and Jess discuss the challenge and necessity of being at peace with not knowing when (or if) key personal and professional milestones will occur.

  • Relatable Moment (30:36, Heather):
    “I could enjoy it more if I knew the when... But the not knowing is what kills me.”

• Presence in Parenting, Work, and Relationships:
  They reflect on being told to “enjoy the moment” in tough times—an oft-resented cliché—acknowledging it’s both hard and fleeting, and reframing the narrative to accept multiple truths at once.

Connecting Work to Meaning

• Infusing Purpose into Any Role:
  Any job can become meaningful when intentionally connected to serving others. Jess encourages listeners to make this connection consciously, even if the work isn’t their “passion” (54:09).

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Notable Quotes & Memorable Moments

• On social capital:
  “I'm putting my social capital on the line for you. ...If someone does the homework, that is something I can consider.” — Jess, 05:09

• On letting go of needing universal approval:
  “The minute you let go of that outcome—because it's none of our business how others feel—it's just so much easier mentally.” — Heather, 48:09

• On the myth of a finish line:
  “I was kind of putting this making-it label on things I thought would solve problems... There are not these thresholds that launch you into a zero inbox, no problems.” — Jess, 49:19

• On the success fingerprint:
  “Today my version of success is to do enough at work so I have the flexibility outside of it.” — Jess, 22:13

• On meaningful work:
  “Any work can be meaningful work if you take the time to connect it to a human... It takes an extra effort but is worth it in the long run.” — Jess, 54:09

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Timestamps for Important Segments

• [03:03] Building true social capital and leading with generosity
• [09:24] Tips for making “asks” easier and more thoughtful
• [17:34] Jess’s entrepreneurial journey: founding, scaling, and selling Headbands of Hope
• [22:13] Creating a personal “success fingerprint” and auditing your ambitions
• [30:36] Navigating uncertainty and the “delay” of happiness
• [41:15] Gaining perspective through stepping outside routine and visualization
• [49:19] Shifting from singular finish lines to ongoing, meaningful problems to solve
• [54:09] Finding meaning in any kind of work

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Who Should Listen/Read This Book?

Jess’s Making It Without Losing It is aimed at anyone (not just women) who feels caught between the yearning for future achievement and finding joy in the present. If you struggle with balancing ambition, fulfillment, and well-being, these insights and exercises are designed for you.

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Resources Mentioned

• Success Fingerprint GPT (Available for pre-orders at JessEkstrom.com/makingit; pre-orders also receive the audiobook free before May 5)
• Making It Without Losing It by Jess Ekstrom

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Final Thoughts

Both Heather and Jess model a candid, authentic conversation about ambition, setbacks, personal evolution, and purpose. Their advice is actionable and compassionate, focusing on creating joy while in pursuit of success—not just after you arrive. You’ll walk away with practical mindset shifts and reflections for enjoying your own journey, no matter where you are on the “path to making it.”

Transcript

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[Jess Extrom]

Don't try to achieve things, to have zero problems. Do things that have problems you're excited to solve. And once I realized that like, oh, there are not these like thresholds that launch you into like a zero inbox. No problems. It's all about like, do you like the problems you're solving? Do you like the people that you're with? Do you like the lifestyle that it affords? And it just changed from these like singular finish line outcomes to a more evolving process that just makes it more fun and also more scalable.

[Heather]

Come on this journey with me each week when you join me. We are going to chase down our goals, overcome adversity and set you up

[Jess Extrom]

for a better tomorrow.

[Heather]

I'm ready for my closeup. Hi and welcome back. I'm so glad you're back here with me this week. Okay, this week we have a repeat guest on because she's unbelievable and you're going to love her because you might not have heard her. It's been a minute she's since she's been on the show. Jess Extrom. She's the founder of Headbands of Hope and Mic Drop Workshop, investor in Women, bestselling author, Forbes top rated speaker, and she's a mom. Her first brush with success was selling all of her toys on ebay when she was 12. Since then, Jess and her companies have been featured on the Today Show, Good Morning America, and more. More importantly, her companies have helped millions of women and girls around the world this is true. She's the bestselling author of Chasing the Bright side, that's When I Met you and Making It Without Losing It. Her hobbies include writing, hiking, board games with her husband, playing hide and seek with our kids. You're hilarious. And searching for the best breakfast burrito in America. Jess, thank you so much for being here. Oh, my God.

[Jess Extrom]

Thanks for having me. Before we get started, I have to share something with your listeners about you. Can I do that?

[Podcast Sponsor/Announcer]

Of course.

[Jess Extrom]

So I just have to say that a lot of people talk about, like, oh, women supporting women, and, you know, blah, blah, blah, which, of course, you know that I stand for. But I just have to say how. You don't talk the talk, you walk the walk. As soon as I mentioned that I had a book coming out, you were like, here, let's get you on my show. Boom, boom, boom, boom, boom. And I think a lot of people are quick to give, like, encouragement, and not a lot of people are quick to give opportunity. And you are so willing and generous with giving opportunity. I mean, you've made introductions for me for speaking. You're like, just. So you walk the walk. And I just really appreciate it. And yeah, I just really appreciate you.

[Heather]

Oh, my gosh, I appreciate you. You're the exact same. You're always making introductions, asking how you can help. And what's funny is, in contrast, as you and I were just talking, I was speaking at a conference in Costa Rica for the last five days. I was gone. And while I was there, I got a text from someone. This person will be unnamed because I don't like naming people when it's negative. But this person, who is not a woman, sent me a message. I hadn't spoken this person in months. And it's someone in our arena. You know, we're all like, when we can help each other out, we want to. And not everyone always feels the same way. And I understand that. But this person sent me a note and just said, hey, need this intro. And dropped a name into a chat to me, which is like, stop. It was interesting because. And this is super valuable, I hope, for everyone, because we all need to remind ourselves of this. If you want someone to do something for you, especially a big ask, right? Because if yeah. Has a coveted name or someone, nobody wants me giving it, nor you giving out all their information and saying, yeah, yeah, let me go ahead and connect you. That's. That's annoying, right? And so when you want someone to do something for you, lead first with how you can help other people. And like, that truly how you lead. And it was just disheartening for me. Or disappointing, I guess is a better word to see this person show up and just kind of like command an intro to somebody. That was like, it was mind blowing.

[Jess Extrom]

That is wild behavior. But I also see it all the time where it is one. We all have that person where their name comes up on our phone and we know that before we even click on the text or the email, they are asking you for something, a favor. This, I need this. Can I pick your brain? And I think it's just like such a good reminder that it's like, how are you building your, like, social capital? And I like to. And. And I have to be kind of be careful with this because I know that I do have a tendency to be transactional in nature. I think just when you're running a business and you're. Or not even just running a business, you're just in life and you're constantly valuing, like, time, relationships and things like that, you are always maybe questioning, am I getting out of this, what I'm putting into it? And so I think that there's a healthy amount of transactional nature of relationships. But sometimes I can maybe be a little bit too much, like, making sure, you know, that things are even on both sides. But when it is asking for relationships and introductions, it's like, I'm putting my social capital on the line for you. Like, I did this the other day with my friend Damon West. Do you know Damon? I do okay. Great guy. And him and I have been really great with helping each other, like, make introductions to speaking or whatever it might be. And he was just on Jefferson's Fisher. Jefferson Fisher's the Next Conversation podcast, which I really love. And as a public speaking expert, like, I really want to get on that show. And so I wasn't just like, hey, can you introduce me to Jefferson? I was like, here is basically a. Like, I'm submitting a. What's it called when you, like, get your PhD a dissertation as to why Jefferson's show is like, perfect fit for me. Like, I'm not just copy paste spam. And so if someone does that where it's like, man, you really put in the time to did the homework, then again, that is like, something I can consider. But, yeah, I get that a lot. And I know that you do too.

[Heather]

Yeah. And for everyone listening, you know, it's not just in the speaking business. It's not just in the podcasting world. It's in life.

[Podcast Sponsor/Announcer]

Right.

[Heather]

Like you're going to want to from somebody once in a while. You know, people oftentimes get nervous to ask. And here's the thing, and I know we both feel like this, if someone asks us for a favor that's easy for us to do and we like people, they're nice people, it makes me happy to do it right. Don't let asking hold you back. Just know to ask in the proper way, like by putting yourself in the other person's shoes, being thoughtful about what you can do to help them, you know, hey, I realize this is a big ask. Hey, I know that your social capital is massive and this is going to take a hit for you. What I do for you, because I don't want this relationship even just saying something as simplistic as that.

[Jess Extrom]

Do the work for them. Like, I, you know, of course with this book you're like, okay, I. And I get really kind of self conscious about when a book comes out because I know that I feel start feeling like I'm asking people for favors, whether that's an endorsement podcast, like what we're doing now, or buy the book or something. And I know I have to get out of my head. And I tell my speakers this at mic drop all the time. You're not asking for a favor if you believe what you're doing is valuable. But I also like when it came to asking for endorsements or things like that, I did took some time to figure out what they were working on. Oh, you have a book coming out this time. You have a foundation that you're raising money for. And so instead of just saying, can you do this? It's like, here are some ways that I would love to return the favor, contribute to you based on, like, what they're doing. And I felt like that went such a long way. Even if they didn't take me up on it, they just saw that I did the homework, which I think is, you know, age that where everything is so quick. Just taking the little bit of time to do show that you did your research or do the homework is. Goes a long way.

[Heather]

Oh my gosh. First of all, 90% of people do not do their homework. 90% of people are just coming in, thinking about it through the lens of themselves. So great point, great example for anyone that before you ask someone for something, do the homework. Another thing that I do that I think that I find helpful when I ask people for, whether it be a testimonial or an endorsement for a book, I'll write up three different options of Potential just to make it easy for them. Right? Because again, not saying it, but saying, hey, if you're struggling with what you would say, here's a couple of ideas I came up with. I don't. I'm not trying to put words into your mouth, but thought this could be helpful for you because I know you're busy. Every single time I do that for endorsements, someone will just pick one of the options because then they can have it off their plate. Be happy to help. And it took them, you know, less than 30 seconds.

[Jess Extrom]

Oh, my gosh, it goes such a long way to make it easy for them. The other thing that I found, and I think this is really great conversation because you and I have had a lot of no's, but we've had a lot of yeses. And the. It's certain, like, you know, showing your playbook of how to get the S, I think can be really important, especially for women. And one of the things that I started doing, you know, is to make any ask an offer. So what I mean by that is when I talk about this at Mic Drop Workshop, I say, like, don't say, can I speak at your event? That's an ask. Make it an offer. I see that you are hosting, like, a women's leadership summit, and I offer, you know, professional development services for women. That takes blah, blah, blah. Would that be helpful to you or would that be helpful for your event? And so it's not saying, can I do this or can I have a speaking spot? And now that we're hosting our own conference in May and I'm getting all the speaker inquiries, I am seeing, like, how many people just say, like, do you have. Are you still accepting speakers? Can I speak at your event? Instead of, I see you're hosting an event. I see it's for women. I see it's for women who are interested in speaking. I do. I'm a body language expert. Would that be helpful for you? It's like, wow, just taking the time to make an ask an offer is like. It lands so differently. It. It changes from, like a exchange of power to a partnership. Because now you're saying, does this work for you? Does this work for me? Instead of like, please can I speak at your event? Or can I be on your podcast? I used to do that. It didn't work.

[Heather]

That is such a great example. Just to show your own worth, too. Just the way you teed it up, there's very little worth in someone saying, hey, can I speak at your event? Right. There's it doesn't seem like any like I'd be doing you a favor allowing you to speak at my event versus when you're addressing how you could add value to that audience, how you could add value to that individual. Now you're coming from a place of worth and people are going to see you differently. When you see yourself as worthy, when you see yourself as valuable, other people will as well. Meet a different guest each week.

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[Heather]

I asked you to try to find your passion. Your business has changed immensely and if you could talk a little bit about that transformation, I think it's super helpful. So many of my listeners are going through transformational windows of time and I know you didn't, you know, when I first met you, when you were chasing the bright side, right? Like think things were so different for you. So at a high level, if you could just talk us through some of these transition you've gone through.

[Jess Extrom]

I think when we first met I was living in our RV and now I'm in a house. So that. So times have changed. We have a working toilet. Heather, this is awesome. Living the dream over here. But yeah, I mean it started for me when I was in college. I interned at Make a Wish. Saw a lot of kids losing their hair to chemotherapy, being offered wigs or hats, and a lot of them wanted to wear headbands. And I call it the dumbest, smartest moment of my life. Being like 17, 18 years old and just purely moving in. Problem solution, not thinking about how many businesses fail. How will this scale? What's my five year plan? I was like, I'm just gonna find a way to give headbands to kids with illnesses. So I started a company called Headbands of Hope. For every headband sold, we donate one to a child with an illness. Which is what I talk about a lot in Chasing the Bright side. And it was not fired right out of the gate. It wasn't this like overnight success. But it eventually went on to donate millions and millions of headbands. Do headbands for the NBA, the WNBA teams. And the way that I was able to really scale that company was through public speaking. I didn't know anything about marketing. Advertising couldn't even spell entrepreneur. But I knew how to tell the story. I could say I discovered this need. Here's what I did about it. And now here's what you can do, too, which is how to start something that matters, how to look for problems in your own, you know, organization or community. And then I remember the first time I got an email from Marshall University saying, what's your fee to speak to our students? I don't. Do you remember, like, the first time you got paid to speak?

[Heather]

Yeah. That it's crazy because, like anything, we have no knowledge. Walking into it when you're.

[Jess Extrom]

No knowledge. I was like, wait, people pay you to do this? This is insane. And I did exactly what I teach my Mic Drop Workshop students not to do was I negotiated against myself. And I said I would. It would be an honor. Just take me to dinner, you know, I would love it. And then I just realized, like, this could be a way to power Headbands of Hope. So I would speak. The money that I would make through speaking, I'd reinvest it into the business. People in the audience would then know about Headbands of Hope. They'd go buy it. Eventually. Headbands of Hope went on to get acquired during the pandemic, which was a whole other identity crisis, which I talk about in the book. It was funny. I was, like, recording the audiobook a few weeks ago, and I thought I knew when I would cry, you know, during the audio. Like, I talk about, you know, I thought it was going to be during the birth of my daughter. Postpartum depression or, you know, my family went through this, like, really prolific scandal when I was in high school. And just like, all this stuff that I thought I was going to cry, none of those. I did it was talking about the sale of my company, and it was just such. I didn't realize, like, how emotional that was for me. Saying goodbye to something that you built and, like, handing over the keys. So that was really interesting. But, you know, Headbands up got acquired, and then I started Mic Drop Workshop, where I realized there's not a lot of women out there speaking, getting paid, landing, like, the big keynote stages, TED talks, things like that. And so I started my Drop Workshop, where we help women become paid public speakers. So I think throughout all of this, though, Heather, like, I think you can tell I also had a complicated relationship to, like, ambition and success where there, I thought, like, selling Headbands of Hope. I mean, and that moment was going to be this. Catapult me into a universe of no problems, because, you know, I did it. And then it was like life went on the next day. Put my pants on one leg at a time, refreshed my inbox, and Things kept moving. And so the inspiration for making it without losing it came from this trend that I see in myself and a lot of high achieving people where when you have ambition towards something you want to accomplish in the future, it always feels like you're at a deficit in the present because you're not there yet. You're like, well, I really want to get this amount of downloads on my podcast, or I really want to make this amount of money. I really want to live in this neighborhood. So the answer is not to like vilify the dream, but it's to become friends with the process of getting there. So it sounds kind of cheesy, but it's like, yeah, there's always going to be another dream, there's always going to be another goal. That's not the problem. Keep having them. But when you make that arrival point, be the reason when you can finally start enjoying yourself or finally start feeling successful. That's when things get tricky because then you're just in a constant cycle of delaying joy, which I've been there, hence making it without losing it.

[Heather]

So what are some of the strategies that you share that people can implement in their life to not hold themselves back from quote, unquote, enjoying the journey? Because, I mean, I am right there with you on there. Seven years ago, I was sitting in Gary Vee's office interviewing him for my show and I remember him saying, like, the most important advice I can give you because I was just starting as an entrepreneur, he said, most important advice I can give you is you need to enjoy the journey. And I didn't say at the time, but after I left there, I was laughing.

[Jess Extrom]

That's bullshit.

[Heather]

Yeah, easy for you to. Here's my opinion. Once you've made it easy for you to say, and P.S. i've made it back in corporate America. So I can say that with like firsthand experience. I remember they'll come up from salesperson to sales manager to EVP to, you know, chief revenue officer. And once I made it to the top, yeah, then I was enjoying the freaking journey because I'm like hitting the, you know, I had the money, I had the title, I had the clout, the expertise. So it's so much easier once, like certain levels of success are achieved. How do you do it? Because I know it's been super hard for me as an entrepreneur. And then with COVID and that like whole window of like, you know, the marketplace changed so drastically that you were reinvented again in those moments of like the come up. How do you ensure that you can find the joy because that's when it's most elusive.

[Jess Extrom]

Yeah, it's so true. And I've had the same reaction. It's like when a really rich person tells you it's not about the money, and it's like, well, it's really easy for you to say that it's not about the money when you have a lot of money. And it's really easy for like, I get this with parenting too. And this is no hate to people giving me this advice. I have a one and a two year old, actually. She, she just turned three. So life is crazy. I told Heather before we started recording, I'm like, schools are closed today. They might come in. I can't control it. And people are like, well, just enjoy it. It goes by so fast. And I'm like, I hear you. Like, your kids wipe their em, but they, you know, go to school. Like they get in the car without you having to do it. And I hear you. Like, I know I'm nostalgic for the present moment. I see how quickly it's going. But sometimes when people are in positions of like, on the other side and they're telling you, it's just like, just enjoy it. It's. It's really like, I, I don't need to hear that. But what I will say is a couple things that were helpful for me. Like, even when I was negative $10,000 in the whole of my first business where I sent money to a fraudulent manufacturer is I always felt like people had a secret they weren't telling me. Like, everyone who was successful had a secret that they weren't telling me. And I just needed to find that secret. I needed to find what they did or what time they woke up or what they had for breakfast that day. And then when you realize that, like the first thing to realize is that no one knows what they're doing. There is no one size fits all. Then you can start figuring out, well, what does it look like for me? And one of the things that we talk about making it without losing it is a success fingerprint. Because everyone has a different version of success. You are going to have a different version than success. And my version of success ten years ago was like being so famous that people would know my name on the streets and that I, I wanted to have a NETFLIX special. I think I even talk about it in my last book. And now I could not think of anything worse than like a camera crew following me around. Today I'm like, absolutely not. And today My version of success is to like do enough at work so I have the flexibility outside of it. And that might mean like I try to be done at three every day so I can play with my kids. Like that means we have a lake house that we like to go to over the summer where I can kind of work at half capacity. And so the kind of fingerprint for my success change. And we actually have a cool pre order incentive going on right now where if you pre order making it without losing it, you get the Success Fingerprint GPT. So you can go in before you read the book and it's going to prompt you with like these questions and it comes up with your success fingerprint before you read the book. It's actually really cool. So figuring out what you want your success fingerprint to be and then realizing that, audit what you're chasing. So it's called the Purpose test. And we can actually do it on this podcast right now. For anyone listening, take the thing that you're chasing, whatever it is, like that goal that you have in mind that you're like, I just gotta get this. Imagine that you got it, it's yours. You got the email, you got the notification, you got the phone call. Someone's like, congratulations, you know it's you. But the kicker is no one knew it was you. You had to remain anonymous. You couldn't post on LinkedIn. I'm pleased to announce that you couldn't tell your spouse, you couldn't tell anyone. Ask yourself, would you still do it? Is this something you would still pursue? And if it is a part of your Success fingerprint, you're probably going to say yes. Because it's not as much of how. It doesn't matter much how it looks. Instead, it's more based on how it feels. And if you know that it matters. And then if you tell yourself, I wouldn't pursue it if I wasn't named, then it might be time to just audit some of the things that you're chasing and decide, is it still something that is important to me? And it might be not auditing the thing that you're chasing, but just how you're going about it, how you think of it. So those are a couple things that I wish early on in my career when I didn't have the success was like, no one knows what they're doing. Success is redefined by each person in each season. And then audit the things that you're chasing and why you're doing it. Because so many times I've chased something cause I'm like, I saw you post. Oh, I should do what Heather's doing. I should do with this. And then it's like, oh, no, she has a different success fingerprint than me. Like, that's okay.

[Heather]

Yeah, that. That's such a great exercise. And for anyone that's listening right now, that's like, oh, my gosh, I need to pre order this. I want to take this test. What's a site that they need to go to in order to get their fingerprint?

[Jess Extrom]

Yeah. Jessextrom.com making it.

[Heather]

I mean, guys, you're going to need to check this out. And you're listening before the May 5 live launch, then you can get this bonus, which is so worth it.

[Jess Extrom]

And you also get the audiobook for free. If you're listening before May 5, you get the audiobook for free when you pre order. Yeah.

[Heather]

That is incredible because that's no joke. That's a lot.

[Jess Extrom]

I know. I had to work with my publisher. I'm like, please. Yeah, so you get the audiobook for free.

[Heather]

Oh my gosh, I love that you did that for everyone, Jess. Okay, so when you were talking about the kids and how people will say to you, enjoy it. I remember people would say that to me when my son was little and I wanted to light them on fire because it's so annoying. Again, back to. You're through that window of time. You know, you got teenagers, kids in college, whatever. You can't relate. And people also look back through a lens that's a rose colored glass. You know, when it's many years later, like, oh, they were so incredible back then. The funny thing is when we're far away from something, either before it's happened or after it's happened, it's distorted. It's typically only when you're in it that you're kind of like, oh, no, this is act like there was a nice moment. But there were also a lot of really hard ones too. Right. Like, you see more clearly when you're in it.

[Jess Extrom]

Yeah. I mean, it's like when you get out of a relationship and you're like, but they look at what they did for my birthday and iPhone brings me these memories of all these good times. And it's like, no, you don't remember all of it or the reason why you left. And I'm not saying that parenthood is just like that, but both things can be true. Like, this can be hard right now and it can also be fleeting. And so I think I'm trying to like, and that's the same in our career. Like, yeah, not every day is going to be like butterflies and sunshine at work. And it can also be the thing that keeps pushing us forward and the thing that we know that we need to keep pursuing. And so, yeah, the whole I am now, I'm very conscious about when I see like someone with a newborn or something. Like, I just am like, how are you? Like, I'm not telling you anything to do or don't miss it, like, or to tell myself. Like, people were like, sleep when the baby sleeps. I'm like, okay, yeah, we're not, we're not doing this right now. Okay.

[Heather]

So I have a different angle and I'm super interested to hear what you think about this. My situation now is that I'm single and people will say to me, oh, enjoy, enjoy. That you shouldn't be rushing to meet someone so quickly. Enjoy this time. You're going to be married someday and you're gonna look back on this and wish you had enjoyed it more. So equally it feels as frustrating. But you know what the funny thing is that I noticed with myself and I wonder if you notice this or if you have a hack around it. In my mind, I'm like, I can grasp that. And listen, let's be honest, people, I have a lot of fun in my life, right? So I do enjoy a lot about my life. I have a great life. However, when there's something that you feel like is missing that you really want, you think about those things. Like that target that, you know, you want to essentially achieve, that person you want to meet. So when I do that, what I find myself doing, which I think is funny, is I'm like, I could enjoy it more if I knew the, when the thing was gonna. If I knew when I was gonna meet the guy. And I don't know why I'm like this, and maybe it's my fear of uncertainty, my fear of unknown, or whatever it is. I'm like, oh, if I knew it was in three months, three days, whatever, whatever the number is, then I'm fine. But the not knowing is the what kills me.

[Jess Extrom]

Yeah, I remember when my husband, he like left his job and had a new job lined up and there was like a one month window where he was unemployed but had his like next job in a month. And I was literally like, life will never be this good again. Like, you know, you have nothing to do now, but. And you know when, like, you have the stability of when, like, enjoy it. But I could totally see how the limbo can drive you Crazy. So how are you managing that? Like, what do you. Does it make you, like, want to frantically find someone, or are you taking the time?

[Heather]

Both can be true, as you just said. Right? So, like, there was windows of time where I was frantically like, I'm gonna go on a date with everybody. And then it turned into charity dating. And this was not headbands of hope. I'm like, no, we gotta fire this concept. Like, that is not gonna work out, people. Right? And then, no, please do not apply. You are not welcome. So I got away from that, and I'm like, that's ridiculous. And then I kept reminding myself, come back to the present moment. Because this is always. This happens when I get way ahead. Like, you know, oh, my gosh, what if I'm still single four months from now, five months from now? So I have to bring myself back to the present moment. I practice what I'm grateful for right now, and then I remind myself of times in my life. Like, I'll go back to, like, all different past relationships. And like, every time, it's like, the next one is a better fit for me and a better fit. And so I'm like, oh, my gosh, Heather. Just this time is passing right now because that person's going through something or you're developing into someone that can be at that next level in a relationship. So I try to turn it into. It's a positive, but it's just like anything. It's a lot of work. And like you said, whether it be parenting, relationships, or your business, there's all these windows of uncertainty, and you thinking this one thing is the right thing that you need to go after. And once you achieve it, you finally made it. And just so often it might be great for a moment in time until you shift gears to that next thing. I mean, is that kind of what you've seen with your. Your own.

[Jess Extrom]

I mean, it's literally, if we're going off of the dating thing, you know, there's literally the term the honeymoon phase. I mean, you're in this period where it's like, oh, this is so great. And then it's, you know, supposed to fizzle. And I think that that is a completely normal reaction to, like, any kind of achievement relationship. Any kind of good is not going to last forever. And that's why things are good. If it was anything that's constant becomes white noise. And so the reason why there's ebbs and flows is, like, because we're not supposed to, like, live life at a volume 10. All the time, or else it wouldn't feel that way. But I think that, like, when it comes to that, like, letdown, it's actually. There's science behind it. It's called the post achievement letdown. And they studied this with Olympic athletes, like, after the Olympics, just this huge, like, emotional crash. I mean, Michael Phelps has been forthcoming about it. Simone Biles has been forthcoming about it. And it's when we put so much weight on one thing, like, Olympics, a wedding, this presentation, and then it's done or it's gone, or it didn't play the way that we thought it would, and it's like. But we played this so many times in our head. And so that's why it's just these. I think it's just. Just being cautious about having so much weight in a singular moment or a singular outcome. There's this, like, painting technique, and I promise I have a point where I'm going to tie this in called pointillism. And it's where, like, the artist puts a bunch of dots on a canvas, and when you're looking at it, you're like, what are you doing? You're just putting a bunch of dots on a canvas. And then when you zoom out, all of the dots create some sort of painting, some sort of, like, picture of something. A tree, a landscape, a person. It's really cool if you look up pointillism. And I like to think about all of the moments in my life are just a dot on my canvas. Like, I'm not living and dying by this one dot. My life isn't, like, make or break by this, like, one dot. Did I get the speaking engagement or did I not? Did I hit the New York Times or did I not? Was I the perfect parent today or not? But when you take a second to, like, step and look back at what's coming together, you can ask yourself, like, well, do I like where the collective dots are heading? Because in the end, that's all that matters, is not, like, one moment, but a collection of them. And so a lot of times, we think about making it as, like, what I was talking about at the beginning of this podcast, like, this acquisition or this one thing, this one moment, when really it's a collection of a bunch of them. And then you. We have these moments in time if we choose to take it where we take a step back, look, and ask ourselves, do I like the direction this is heading? Do I like the painting that all of these dots are putting together? If you don't, then have the courage to change it. And say, well, what's my next one going to be? Because sometimes I have looked at it and been like, you know, I don't really like what I'm doing right now or why I'm doing it or how I think about myself or treat other people along the way. And if it wasn't for like those moments where I look back, then all of a sudden you just like years go by and you're like, holy, I've painted this thing that I just don't even like.

[Heather]

Meet a different guest each week.

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[Heather]

I asked you to try to find your passion. That was my whole experience in corporate America. And at the eventually, at the end, you know, after being in a negative environment for a long time and not even noticing it after a while because it's your job and you just show up and do the job and then you're on the hamster wheel. And I wasn't self reflecting. So I find that super helpful that you point that out. So everyone listening right now. Challenge everyone to take a step back and look if those collective dots are leading you somewhere you want to go. And it's interesting, as I mentioned, I was in Costa Rica for this speaking engagement. However, they had me stay extra days because they wanted to do some workshop work, which typically I don't do. So it was like a spending more time around people I didn't know, spending more time in an environment that was a little uncomfortable to me because a lot of energy. Yeah, you're getting a lot of energy. It's not the people I'm normally like, it's totally different environment. Right? Everything was different. And on the flight, on the way home, Instagram, you know, listening to me talk serves me this really interesting thing which was all about how when you travel, most people will make bigger changes or significant changes to their life when they get back home because they're seeing a completely different vantage point. They're immersing themselves in complete uncertainty. New food, new people, new environment, new area. And so then you get contrast to where your collective dots are, which is back at your normal home, your normal routine. And I took a moment, I was thinking about that and I was like, this is so interesting. So I thought to myself, for me is something I can take from where I was the last five days and apply that back to my routine collective. All these points being brought together and I started thinking like I can make different health choices because this was a very health and wellness conference. And I can have more green in my home because the hotel was like, green every. Like, there was just all these things that I could think of, yeah, this. I could take these little moments and add them back to my regular life to make my regular life better. But it's not something I would typically think of because I'm just running to get home and get through customs and like, jump in the Uber and find out where my kid is. And dude, we get instacart and, you know, you just get in that rut or routine of trying to rush so that you can just, just, you know, be at peace again instead of saying, wait a minute, how can I zoom out? Like you were saying before, how can I zoom out of this? And then say, what's some of the good that you know, could impact me and, and could help me evolve from all of this?

[Jess Extrom]

That's such a good point. And it's so true. Like, I feel like most of my revelations come when I'm on an airplane and I'm like, I should do this or why haven't I been doing that? And you're right. It's like when you get plucked out of your routine, it gives you the opportunity to say, like, I'm looking at it from over here, not in it. And I went like a few years ago on this silent retreat. I am not someone to do this. I'm a professional speaker. I don't sitting in silence. But that's why I needed it. I was like, I just really need to get out of my head. And one of the things that was done at the end of it, which was like one of the most like, transformative moments of my life. During this meditation, he, the guide said, just like, imagine you waking up in your bed at home, like, and you're kind of a bird, like, looking down. Literally play out your whole day in your head. Watch yourself, like, brush your teeth, go make your coffee, all these things. And it was like he asked us a series of questions like, what are you proud of? But I was like, oh, watching myself, like, from afar. And I know this sounds like really woo woo and Hakuna matata right now, but I was like, it just gave me the chance to ask myself, like, do I like the dots I'm putting on the canvas? And an overwhelming amount was like, no. Because I realized that the amount of time that I am not present with my family or the people and I'm on my phone or I'm thinking about work or something. Like, I could almost see myself, like, doing bath time with my kids, sitting there scrolling something. And I just wanted to, like, say, like, what the fuck are you doing? Like, this is like, be right here. And so that was when I really made. I mean, and it's been a work in progress, but like a big change on the boundaries that I have with my phone because I took a second to, like, step outside of myself and ask, like, do I, like, where all of these daily decision and these dots are heading in this, like, one department of presence with my family, with my kids, with the people in my life. I was like, I feel like I could be better at that. But it literally took me, like, visualizing myself in my routine in order to do that, which is kind of crazy. I hope it doesn't have to be that extreme for anyone listening. But that was what did it for me.

[Heather]

That's so interesting because I've never heard of that exercise before, but it makes so much sense. And when you were sitting there talking, explaining it, I was going through in my own mind. And that's one of the things I'm grateful for, for this random, you know, event in Costa Rica, because it was so polar and we were cold, plunging, like, the crazy things we're doing that I've never done in my life, riding horses. Like, all these things about trying to get you out of your head, right, and. And into your body for health and all this different stuff. But when you just had me think through what you were going through, I

[Jess Extrom]

started, yeah, what came up for you?

[Heather]

I was thinking about my day now, being back in my home office, not being around people all day, being on Zoom. That was the first thing that came to you. I don't like that. Right. But, like, it's interesting until you really, like, pump the brakes for a minute. There's plenty of good about being at home and being on Zoom because it makes things easy for you. And I can be home to make my son dinner tonight. There's plenty of wins from it. But then when you kind of step back and say, there are plenty of wins, but at the same time, I prefer to be in person with real people. And it's just interesting because our dynamic as a society has changed so drastically because of technology. So much for efficiency and good, but so much that really isolates you. And I often forget it until I'm speaking at an event and around so many people. And I don't know if you have that same thing. Like, yes, it can be exhausting and draining being around so Many people and giving them all your energy, but at the same time, it can be so rewarding versus being at home a lot or for you at home and then also with little kids, which isn't riveting in regards to the conversations you're gonna have, right?

[Jess Extrom]

Yeah. Do you ever experience the, like, when you get home from a trip, like, the speaking, like that post achievement letdown that I'm talking about?

[Heather]

Yeah, a hundred for every single time I do. Every single time.

[Jess Extrom]

And it's like, it's funny because you go from this, like, adoring. I'm on a stage in front of people that are, you know, asking me to sign something or, like, and then all of a sudden to just being back to reality, which part of it is like, I love, like, coming home and. And everything. And then there's another part of me that is asks myself, like, how much of my energy and just like, daily tally of what I have in the bank goes to, like, impressing strangers versus, you know, at home. And I get that. Again, that's like a privilege to think about it that way. But I do think a lot about, like, am I giving it all to a room full of people and then coming back on E to the people that matter most? And I think one of the ways that I've been able to help with that, like, that phone thing in the kind of walking through your day really helped me see this was I don't necessarily have to go up there in front of people and have this super energetic talk show personality after having kids. It actually helped me put some of those moments, those speaking moments into perspective. Because for me, before having kids, it was like, this is the most important thing I'll ever do. And I agree that it's really important. But my life will go on if someone doesn't laugh at my joke. Like, my life will go on if Bill didn't think my talk was valuable, you know, like, whereas before, that would have broken me. And so I almost feel like I have become a better speaker in a lower energy given by just caring a little bit less. And I don't mean caring less about the people. I don't mean caring less about the purpose, but I mean caring less about how I'm perceived while doing it. And I think that that has helped me protect my energy in meetings, in. On stage. It's just like, I'm gonna figure out what they need. I'm gonna see how I can help, but I'm not gonna try to make them love me, because that is just draining. And Uncontrollable.

[Heather]

It's so good and so true. And I. That used to consume me. That woman that I used to work with in corporate America couldn't stand me. And it drove me crazy. I wanted, I. We want people to love us, right?

[Jess Extrom]

Of course.

[Heather]

The minute you let go of that and let go of that outcome, because it's none of our business how others feel like, it's just so much easier mentally. Stop draining yourself. Get your energy back, Take your power back. One of the things that I know when I gave my TEDx talk, which you've done a couple of them, I put so much pressure on myself, which was so unnecessary. It's the most important talk of my life. And I still think it's so funny that I thought that. But at the time I did, what I having to do because I had so much pressure on me was to say, Heather, literally I talked to myself in a third person like this. Heather, if you help one person as a result of this talk, you've done your job and let it go. Just lower the expectation, lower the pressure. Because the more you lower that pressure on yourself, the better you're going to perform. The more you you're actually going to be, which means the more you're actually going to connect with people. So let's get back to the book here. What does making it mean to you that you were trying to convey to the listener? Or is it really about the steps in showing them how not to lose it? Which is it. Is it about how, how you can make it, or is it more about how you can keep it together while you're on your way to finding out what making it actually is?

[Jess Extrom]

I'll tell you a quick story from the book where I had just gotten like, bad news from. I can't remember if it was like an agent or an editor for. From a previous book that they didn't like it. I got like terrible edits and. Or at least I thought they were terrible edits. It was probably just edits. And the. I was talking to, I have a business coach, Aaron Foley, who's awesome. And I was talking to her about it and she was like, what kind of problems do you think a New York Times bestselling author has? And I was like, probably, you know, I don't know, like social media, getting edits, doing this. Then she's like, exactly. Don't try to achieve things, to have zero problems. Do things that have problems you're excited to solve. And so I was kind of putting this, like, making it label on things that I thought would solve problems. Like if I just got this status, this much, this thing, and everything was always outside of me. It was always like, I want to sell this amount. Be it never. It was never internal. And once I realized that, like, oh, there are not these, like, thresholds that launch you into like a zero inbox. No problems. It's all about like, do you like the problems you're solving? Do you like the people that you're with? Do you like the lifestyle that it affords? And it just kinds of. It just changed from these, like, singular finish line outcomes to a more evolving process that just makes it more fun and also more scalable. There was research around companies who had a singular outcome that they were going after and how it dropped. Motivation dropped at the company, like an IPO or acquisition or a big product launch. And then they looked at companies that did those things but then had sustained motivation. Like, their numbers didn't drop. And like, what did they do differently? They looked at Google and instead of Google's mission being like, create the world's, like, leading search engine, they said, we organize the world's ideas. And so it wasn't a finish line, it was a mission. It was like, there's always going to be more ideas that need, that need Google. And so the fact that they were able to switch from like, we're not creating the search engine, it's like, we organize the world's information that's going to change. That was like a game changer for me in this book in making it without losing it is like, how do you create goals, have a mission that aren't this singular focus, but even outlive you? Like, I think about what I'm doing today and yes, I want it to be great for me, but I want it to be like something my great grandkids one day might experience of like, hey, there's a lot of women on stages and I can say I was a small part in that. So sometimes it's just not about achieving your goals. It's about being a part of things that might even outlive you, which I think is really a cool way to think about it.

[Heather]

Yeah, being a part of things that matter to you is everything. It's so funny. I was driving the other day and randomly saw a sign about a charity helping children. And I had been on charity called city year for 10 years. I was on the board. And then as I became an entrepreneur, I didn't have as much free time on nights and weekends as I did when I was in corporate. So I had pulled back from the charity. And when I saw that sign, immediately I was like, purpose calling. Like I could just, I could feel it, physically feel it. And here's the thing, sometimes the work you're doing is meaningful and important and you're helping people and feel good about it. But you're also like, I feel like I'm missing something. You can sometimes add something else into the mix. You don't have to completely walk away for something.

[Jess Extrom]

Oh, for sure, for sure. I like to think about it. Did you read what's it called? Marie Kondo, Spark Joy during the pandemic, when everyone was reading it and decluttering their homes. So I think about it when it comes to work. One of the things that like she would do is say like, take an item, hold it close to your chest. Does it spark joy? If yes, keep it. If no, toss it. But then there was this part of the book where it's like, well, what happens when you get to like a stapler or a hammer? It's like, this doesn't necessarily spark joy, but like, what if I need to staple something and what if I need to hammer in a nail? And she talked about, remind yourself what that thing does that gives you joy. So this stapler helped me like hang up my kids artwork or in their room, or this hammer helped me build a like bird shed, you know, for like all the birds in my yard.

[Heather]

And.

[Jess Extrom]

And it's the same thing with our job. We don't have to, I think like sometimes just follow your passion and do what you love is so overused. But I think that any work can be meaningful work if you take the time to connect it to a human. Like the thing that you're doing might not be exciting or enticing, or you might not love every task, but I guarantee you can connect a task to a greater outcome for someone else. Someone else you probably won't even meet. But it's there. And so I think that meaningful work isn't something that's like assigned at a job or you have to leave to find it. It's something that's created by you in your role that takes an extra effort but is worth it in the long run.

[Heather]

It's so worth it because it will give you that intrinsic joy that we're all wanting to find.

[Jess Extrom]

For sure. I mean, there are people who have the same job, same roles, Someone thinks it's the best thing they've ever done that's so meaningful to them. I mean, I'm speaking at the YMCA this week for employees and been like doing some research and some case studies. And you know, it's like there are people there that. And I see, I'm a member of the Y, that their job is to clean the equipment, but they're also like counting people's reps and encouraging people on the treadmill. And then you have other people that are just like not at the Y but at other gyms that are just like, like, when do I sign out? I've cleaned the bathrooms, where do I go? So it's like, well, what's the difference between the people who truly think that their job is meaningful and the ones that aren't? It's usually not the role. It's usually how you think about it and how you connect it to people behind it.

[Heather]

Oh my gosh, that is so true. And we can all see that everywhere. It was making me think of the hotel I just stayed in and some of the employees were so invested in you having a great experience and what they magical and different and you could see, see the joy in their eyes. And you are just drawn to those people. Right? So it's like you become more interesting, more beautiful, more exceptional when you actually care about what you're doing. So tell us, who did you write the book Making It Without Losing it for?

[Jess Extrom]

Making It Without Losing it is for anyone who maybe is struggling with like ambition towards the future, with feeling like grounded, happy, prideful in the present. So I love speaking to women, but it's not just for women. It's for men too. And anyone who doesn't want to sacrifice like productivity and peace, I want to do both at the same time. You can grab a copy wherever books are sold very soon. You can grab it now, but it comes out May 5th. Yeah.

[Heather]

Okay. And for the pre order, they're gonna. If they, if you pre order it now, you are going to get the audiobook for free.

[Jess Extrom]

You'll get the audiobook for free. And the Success Fingerprint GPT so you can go to Jesse.com making it Jess,

[Heather]

thank you so much for all you're doing to bring so much good forward to share these incredible learning teachings and help so many people. I so appreciate you, Heather.

[Jess Extrom]

You're the best. Thank you so much for having me.

[Heather]

Guys, go get the book. Don't miss out. You're getting a free audiobook. You have no idea how many hours that takes to create. I am so impressed by this. I never heard of anyone give their audiobook away. Go get this book. Go to our site. I will link it in the show notes until next week. Keep creating your confidence. You know I will be. I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone.

[Jess Extrom]

You don't stop and look around once in a while. You could miss it.

[Heather]

Come on this journey with me.