In short
How to pursue big goals without delaying happiness; redefining success, managing “post-achievement letdown,” and making social asks without being transactional.
Guest
Jess Ekstrom, founder of Headbands of Hope and Mic Drop Workshop; investor in women; best-selling author (Chasing the Bright Side, Making It Without Losing It); Forbes top-rated speaker; mom. Early success: sold toys on eBay at age 12. Headbands of Hope: inspired by Make-A-Wish; donated one headband per sale to kids with illnesses; later donated millions and partnered with NBA/WNBA teams; acquired during the pandemic. She later launched Mic Drop Workshop to help women become paid public speakers.
Key claims
There’s no “zero-problems” threshold—choose problems and people you’re excited about. Success is a “fingerprint” that changes by season; audit what you’re chasing using a “purpose test” (would you still pursue it if anonymous?). For asks, lead with how you can help, do homework, offer options, and “make it an offer” instead of requesting a favor.
Notable examples
negotiating speaking fees to fund Headbands of Hope; using a “dissertation-level” intro for a podcast; phone/social boundaries after visualizing daily life as “dots” (pointillism) and noticing phone distraction.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Shift in Perspective on Happiness
1:12 to 2:56
Understand how to shift focus from achieving goals to enjoying the process.
“Don't try to achieve things to have zero problems, do things that have problems you're excited to solve.”
Women Supporting Women: A Personal Anecdote
2:56 to 3:46
Hear a heartfelt discussion on the importance of support and opportunity among women.
“Before we get started, I have to share something with your listeners about you.”
Building Social Capital: A Two-Way Street
3:46 to 6:08
Learn strategies for building social capital and the importance of reciprocity.
“You're always making introductions, asking how you can help.”
Making Asks: The Importance of Value
6:08 to 8:04
Discover how to effectively ask for favors while providing value.
“But sometimes I can maybe be a little bit too much like making sure, you know, that things are even on both sides.”
Turning Asks into Offers
8:04 to 9:24
Learn the value of framing requests as offers to create partnerships.
“Even just saying something as simplistic as that.”
Jess Ekstrom's Business Transformation
15:20 to 17:48
Jess Ekstrom discusses her journey from living in an RV to founding Headbands of Hope.
“And if you could talk a little bit about that transformation, I think it's super helpful.”
The Emotional Journey of Business Success
17:48 to 20:47
Jess shares the emotional highs and lows of selling her company and the complexities of ambition.
“So I would speak the money that I would make through speaking.”
Finding Joy in the Journey
20:47 to 26:52
Discussing the importance of enjoying the process while pursuing goals, despite challenges.
“Because I know it's been super hard for me as an entrepreneur.”
Auditing Your Goals and Success
26:52 to 28:00
Jess introduces the concept of a success fingerprint and how to assess personal goals.
“Yeah, that that's such a great exercise.”
Navigating Moments of Hardship and Joy
28:00 to 29:20
Explore the duality of parenting and career challenges amidst fleeting joys.
“You know, when it's many years later, they're like, oh, they were so incredible back then.”
Show all 22 chapters
The Dilemma of Enjoying the Present
29:20 to 31:38
Discuss the struggle of enjoying life while pursuing significant goals.
“So I have a different angle and I'm super interested to hear what you think about this.”
Understanding Post-Achievement Letdown
31:38 to 33:59
Learn about the concept of post-achievement letdown and its psychological effects.
“I practice what I'm grateful for right now.”
The Art of Life's Collective Moments
33:59 to 36:08
Discover how to view life as a collection of moments rather than isolated achievements.
“Like I'm not living and dying by this one dot.”
Finding Clarity Through Self-Reflection
38:56 to 42:01
Engage in the importance of taking a step back to evaluate life's direction.
“That was my whole experience in corporate America.”
Visualizing Daily Presence
42:01 to 43:42
Discover the power of visualizing your daily routine to enhance presence and connection with loved ones.
“like and you're kind of a bird, like looking down.”
Balancing Work and Family Life
43:43 to 45:28
Explore the challenges of maintaining work-life balance, especially in a digital age.
“That's so interesting because I've never heard of that exercise before, but it makes so much sense.”
The Energy Exchange of Public Speaking
45:29 to 47:40
Understand the emotional dynamics of public speaking and the energy drain it can cause.
“And I get that, again, that's like a privilege to think about it that way.”
Redefining Success and Pressure
47:41 to 49:18
Learn how to redefine what success means and reduce self-imposed pressure in performance contexts.
“It's just like, I'm going to figure out what they need.”
Finding Meaning in Your Work
49:19 to 51:56
Examine how to derive meaning from work and connect it to broader goals beyond mere achievement.
“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.”
Creating Connections in Work
51:57 to 54:36
Discover the importance of connecting tasks to human outcomes to enhance job satisfaction.
“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.”
Understanding 'Making It Without Losing It'
56:01 to 56:39
Jess Ekstrom discusses her book and its audience, emphasizing balance in ambition and happiness.
“So it's like you become more interesting, more beautiful, more exceptional when you actually care about what you're doing.”
Appreciation and Encouragement from Heather
56:53 to 57:26
Heather expresses gratitude towards Jess and encourages listeners to purchase her book.
“jessextrom.com making it jess 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.”
Transcript
Automatic transcript. May contain errors.0:00Heather Monahan:It's free to sign up and posting a job is easy. Visit Upwork.com right now and post your job for free. That is Upwork.com to connect with top talent ready to help your business grow. That's U-P-W-O-R-K.com. Upwork.com. Whether you need help covering payroll, managing cash flow, or investing in growth, you deserve better. That's why I recommend the small business marketplace Fundera, powered by NerdWallet. It's free, easy-to-use platform that lets you compare real financing offers from trusted lenders all in one place. Go to nerdwallet.com slash confidence to find the funding you deserve. Refresh your spring wardrobe with Quince.
0:43Heather Monahan:Go to quince.com slash confidence for free shipping and 365 day returns. Go to quince.com slash confidence for free shipping and 365 day returns. quince.com slash confidence. On Whatnot, you go live and sell directly to people in real time. You go live, show off products and turn what you love into real income. Visit whatnot.com slash sell to start selling. 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?
1:33Do 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.
1:51Heather Monahan:I'm 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 for a better tomorrow. I'm ready for my close up. 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 since she's been on the show. Jess Ekstrom, she's the founder of Headbands of Hope and Mic Drop Workshop, investor in women, best-selling 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.
2:29Heather Monahan: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 best-selling 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 her kids, you're hilarious, and searching for the best breakfast burrito in America. Jess, thank you so much for being here. Oh my god, thanks for having me. Before we get started, I have to share something with your listeners about you.
3:01Can I do that? Of course. 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.
3:39You're like, just so you walk the walk and I just really appreciate it. And yeah, I just really appreciate you.
3:48Heather Monahan: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 to 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.
4:21Heather Monahan: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, 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 someone has a coveted name or someone, nobody wants me giving it, nor you giving out all their information and saying, oh 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 is 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 it was like it was mind-blowing 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.
5:20And we know that before we even click on the text or the email, they are asking you for something, a favor of 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 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?
6:05And 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. 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.
6:52And 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 uh what's it called when you like get your PhD a dissertation as to why Jefferson's show is like the 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. Yeah.
7:30Heather Monahan: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, right? Like you're going to want to give up 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.
8:00Heather Monahan: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 can I do for you? Because I don't want this relationship. Even just saying something as simplistic as that. 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.
8:51Oh, 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 an age that where everything is so quick, just taking a little bit of time to do show that you did your research or do the homework is goes a long way.
9:24Heather Monahan: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.
9:57Heather Monahan: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 to do. 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 a great conversation because you and I have had a lot of no's, but we've had a lot of yeses. And it's certain, like, you know, showing your playbook of how to get the yes, I think can be really important, especially for women.
10:31And 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?
11:21Can 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.
11:57Heather Monahan:That is such a great example, just to show your own worth to 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 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 work 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.
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15:26Heather Monahan: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 things were so different for you. So at a high level, if you could just talk us through some of these transitions you've gone through. 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.
16:01I 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 going to 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.
16:35And 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 WMDA 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.
17:10And 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?
17:21Heather Monahan:Yeah, that it's crazy. Cause like anything, we have no knowledge walking into it when you're starting. Their 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.
17:55They'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 audio book 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 I 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.
18:32And 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.
19:28And then it was like life went on the next day, put my pants on one leg at a time, refresh 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. and you're like, well, I really want to get this amount of downloads on my podcast. 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.
20:16So 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.
20:47Heather Monahan: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'll i mean i am right there with you i'll never know seven years ago i was sitting in gary b'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 that's bullshit yeah easy for you here 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 i can say that with like firsthand experience i remember the 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 cloud expertise so it's so much easier once like certain levels of success are achieved.
21:49Heather Monahan: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. 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.
22:24And this is no hate to people giving me this advice. I have a one and a two-year-old. Actually, 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 own butt 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 hole in 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.
23:27Like 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 10 years ago was like being so famous that that people would like know my name on the streets and that I, uh, I wanted to have a Netflix special.
24:13I think I even talked 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 GBT.
24:56So 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.
25:33Someone'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 of 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?
Read the full transcript
26:21And 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. It 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 because I'm like, I saw you post it. Oh, I should do what Heather's doing. I should do what this. And then it's like, oh, no, that she has a different success fingerprint than me.
26:52Like, that's OK.
26:54Heather Monahan: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 preorder this. I want to take this test. What's a site that they need to go to in order to get their finger? Yeah, just extra dot com slash making it. I mean, guys, you're going to need to check this out and you're listening before the May 5th live launch, then you can get this bonus, which is so worth it. And you also get the audio book for free. If you're listening before May 5th, you get the audio book for free when you pre-order. Yeah. That is incredible because that's no joke.
27:27That's a lot. I know. I had to work with my publisher. I'm like, please. Yeah. So you get the audio book for free.
27:32Heather Monahan: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've 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, they're 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.
28:09Heather Monahan:It's typically only when you're in it that you're kind of like, oh no, this is like, there was a nice moment today, but there were also a lot of really hard ones too, right? Like you see more clearly when you're in it. Yeah, I mean, it's like when you get out of a relationship and you're like, but 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.
28:40And 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 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.
29:19Okay.
29:20Heather Monahan: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 going to look back on this and wish you had enjoyed it more. So equally it's feel 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?
29:50Heather Monahan: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 or 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 be 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 that I'm fine But the not knowing is what kills me.
30:28Yeah. 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 are you does it make you like want to frantically find someone or are you taking the time both can
31:09Heather Monahan:be true as you just said before 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 dirty 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? No, no, 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?
31:37Heather Monahan: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 kind of 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.
32:14Heather Monahan: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 own? 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.
32:52If 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 uh 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 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.
34:29Like 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 this 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.
35:17And 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? And 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 shit, I've painted this thing that I just don't even like.
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37:24Heather Monahan:Visit whatnot.com slash sell to start selling. That's W-H-A-T-N-O-T dot com slash sell. WhatNot dot com slash sell. I've been doing a little spring reset with my closet lately, focusing more on quality over quantity, just building a wardrobe of pieces that are well-made, versatile, and easy to reach for every day. That's why I keep coming back to Quince. The fabrics feel elevated, the fits are thoughtful, and the pricing actually makes sense. Quince makes beautiful everyday pieces using premium materials like 100 % European linen, organic cotton, and super soft denim with styles starting around$50.
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38:42Heather Monahan:Now available in Canada too. Go to quince.com slash confidence for free shipping and 365-day returns. Quince.com slash confidence. I ask you to try to find your passion. That was my whole experience in corporate America. And 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.
39:23Heather Monahan: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. And 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. You're getting a lot of energy. It's not the people I'm normally about. Like it's a 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.
40:08Heather Monahan: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, And 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 in the last five days and apply that back to my routine collective, all these points being brought together. And I started thinking, I can make different health choices because this was a very health and wellness conference.
40:37Heather Monahan:And I can have more green in my home because the hotel was green. There were just all these things that I could think of. Yeah, 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, 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 could help me evolve from all of this.
41:15That'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.
42:08Literally 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 akuna 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.
42:55And 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? And 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 and my routine in order to do that, which is kind of crazy.
43:38I hope it It doesn't have to be that extreme for anyone listening, but that was what did it for me.
43:43Heather Monahan: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 and 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 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 into your body for health and all this different stuff. But when you just had me think through what you were going through, I started - Yeah, what came up for you?
44:14Heather Monahan: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 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. Like 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 like, 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.
44:54Heather Monahan: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 going to have. Right. 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? Yeah. A hundred for every single time I do.
45:32yeah and it's like um 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?
46:27and 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.
47:18And so I almost feel like I have become a better speaker and 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 and on stage. It's just like, I'm going to figure out what they need. I'm going to see how I can help, but I'm not going to try to make them love me. Cause that is just draining and uncontrollable.
47:57Heather Monahan:It's so good. It's 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, we want people to love us, right? Of course. The minute you let go of that and let go of that outcome, cause 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 you know build it's the most important talk of my life and I still think it's so funny that I thought that but I at the time I did what I having to do because I had so much pressure on me was to say Heather and literally I talked to myself and 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.
48:47Heather Monahan: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 you can make it? Or is it more about how you can keep it together while you're on your way to finding out making it actually is? 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.
49:30I 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.
50:16Like 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. 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 kind 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 to the company, like an IPO or acquisition or a big product launch.
51:15And then they looked at companies that did those things, but then had sustained motivation, like their numbers didn't drop. And I'm 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 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.
51:54That was like a game changer for me in this book and 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.
52:36Heather Monahan: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.
53:07Heather Monahan: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. Oh, for sure. For sure. I like to think about it. Did you read, what's it called? Marie Kondo's 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?
53:43It'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 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.
54:35Someone 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 where 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.
54:51Heather Monahan:It's so worth it because it will give you that intrinsic joy that we're all wanting. Yeah, 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 why, 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 why, but at other gyms that are just like, when do I sign out?
55:32I'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.
55:46Heather Monahan: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 vested in you having a great experience and what they can just get magical and different. And you could see the joy in their eyes and you were 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? 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 um 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 uh may 5th yeah okay and for the pre-order they're gonna if they if you pre-order it now you are going to get the audio book for free you'll get the audio book for free and the success fingerprint gpt so uh you can go to jessextrom.com making it jess 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.
57:09Heather Monahan:I so appreciate you. Heather, you're the best. Thank you so much for having me. Guys, go get the book. Don't miss out. You're getting a free audio book. You have no idea how many hours that takes to create. I am so impressed by this. I've never heard of anyone give their audio book away. Go get this book. Go to her site. I will link it in the show notes. Until next week, keep creating your confidence. You know I will be.
57:36Heather Monahan:I couldn't be more excited for what you're going to hear. Start learning and growing. Inevitably, something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. I'm on this journey with me.
From the publisher
What if “making it” doesn’t solve your problems, it just gives you new ones? In this episode, I sit down with Jess Ekstrom, the founder of Headbands of Hope and Mic Drop Workshop, to break down the belief that once you “make it,” everything will finally feel easier, happier, and complete. We talk about the pressure of constantly chasing the next goal, the illusion that success will solve your problems, and how to stop tying your happiness to future outcomes. Jess also shares the idea of choosing problems you actually want to solve, defining your own success fingerprint, and shifting from achievement-based thinking to mission-driven living. Get ready to rethink what success means and start creating a life that feels good now, not “someday.”
In This Episode You Will Learn
How to STOP chasing outcomes that promise a problem-free life.
The PURPOSE TEST to evaluate if your goals are aligned with you.
How to define your SUCCESS FINGERPRINT based on your values.
How to shift from singular goals to a MISSION that keeps you motivated.
Why attaching your happiness to a FINISH LINE keeps you stuck in a cycle of delay.
How to ZOOM OUT and evaluate if your daily actions align with your life.
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Resources + Links
Pre-Order Jess Ekstrom’s new book Making It Without Losing It and get the FREE audiobook + BONUSES: https://jessekstrom.com/makingit/
Check out Headbands of Hope and support their mission: headbandsofhope.com
Learn how to become a paid speaker with Mic Drop Workshop: micdropworkshop.com
Call my digital clone at 201-897-2553!
Visit heathermonahan.com
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