Jess Ekstrom (3:42)

The problem?

Nicole Kahlil (3:43)

We live in a world where we are never done. There is always another milestone, another launch, another quarter, another metric, a moving goalpost, another next level. And if we're not actively climbing towards something, we start to feel behind or lazy or irrelevant. So we chase what's next instead of experiencing what's now. And I hate that. For us, somewhere along the way, ambition got tangled up with anxiety. Productivity started getting confused with purpose. And we told ourselves we'd feel good enough when we accomplished, then we would rest, then we'd be enough. We tied our worth to our achievements and then never let ourselves experience them. We didn't celebrate. No. We refused to sit with any achievement for longer than three seconds before we were on to the next one. And we're standing here wondering why motivation feels so hard to access. Meanwhile, I have to imagine motivation is looking at us saying, I show up, I help you build, and it's never enough for you. So maybe the problem isn't that we lack motivation. Maybe we've misunderstood it. And that's exactly what today's guest is here to help us untangle. Jess Ekstrom is the founder of Headbands of Hope and Mic Drop Workshop, an investor in women, two time bestselling author,

Podcast Host 1 (5:05)

Forbes top rated speaker, and a mom.

Nicole Kahlil (5:08)

Her newest book, Making It Without Losing how to Stay Motivated in a World Where We Are Never Done challenges hustle culture and introduces the arrived mindset, the radical idea that you are already enough right now. Through her work, she's helped millions of women and girls while building businesses that prove ambition and inner peace can coexist. Jess, welcome to the show. Clearly, I have a deep and complicated relationship with motivation, so I'd like to start there. Your subtitle is how to stay motivated in a world where we are never done. So, yeah, how do we actually do that?

Jess Ekstrom (5:47)

Can I first just say I wish I knew you when. Because I'm like, that. You should have written the forward for my book. Everything you were saying, I was like, damn, I should have put that in there. That was a really good line. And so I am so just thrilled to be here as someone who is a fellow, maybe an anxious achiever, who is always like, kind of going after what's next, but the progress bar just keeps extending. It is. I think we write and we teach the things that we learned the hard way. And this is definitely something that I learned the hard way. I kind of felt like ever since, I'll just. I'll just jump right into it. My family, we had a pretty traumatic event happen when I was in high school. My mom's uncle is Bernie Madoff. We had. We lost our money, but was also in a very just public scandal. And being how old was I? Like, 15, 16 years old, I felt like I kind of just went on this quest to right a wrong. I just wanted to be something so big and wonderful that it covered up this pretty intense shit that happened with my family. And then, you know, I just kept thinking, well, I'm gonna start this. I'm gonna do that. And this is going to be the thing that. That solves everyone's problems. That makes me feel like I have made it. And it's like you keep dumping buckets of water into a barrel that you realize has, like, a leaky bottom, and then it's just this hamster wheel that you can't get off of. So it's something that I've struggled with deeply and through writing, making it without losing it. There are certain things that I have found that can be very helpful in feeling like we don't have to choose between ambition towards the future and fulfillment in the present. And one of those things is just recognizing that the finish lines, the confetti cannons, the gold stars really exist there. There's. They're not here. And I think school and how we kind of grew up makes that hard because we had clear finish lines. We had. You're in first grade now, you're in second grade. You've graduated, you got an A. And so it made us feel like, oh, we'll know. We'll know if we're doing a good job. We'll know if we're ready for what's next. We'll know when we're good enough. Because we were Used to getting those metrics and those really clear lines of progress. And then when you're an adult you're

Nicole Kahlil (8:33)

like, hold on, where's my summer?

Jess Ekstrom (8:35)

Is this like exactly? Exactly. So this is as much of a self exploration book as it is for the reader as it is for me.

Nicole Kahlil (8:45)

Yeah. So, okay. Lots of interesting things in what you said. First, the barrel with a leaky bottom. That's exactly how it feels. It doesn't matter how much gets filled, it's never enough because it's always leaking out the side. I think that's a really great visual. It really jives with the way I felt. I'm curious. It's interesting. I wonder how many of us do this because I have a not same story, but similar in that I think I tried to prove myself and maybe still do in relationship to where I came from or you know, my dad's family is. Has a very difficult. And I always wanted to separate myself and prove myself. I'm. I'm curious. I mean, obviously you didn't do it. You're 15 years old, you have no responsibility whatsoever and it still fueled you.

Podcast Host 1 (9:40)

Helpful, hurtful combination.

Nicole Kahlil (9:42)

What do you think about attaching yourself to somebody else's misdeeds and using that as fuel for yourself?

Jess Ekstrom (9:49)

It was a really intense revelation that that's where my ambition was coming from. And something I talk about in making it without losing it is called like your success fingerprint. And it's really helping you uncover how you're defining your success in this reason in this season of your life and gets into these childhood questions of like, when did you first learn what success was? Was it when you watched your parents move into a dream house? Was it a teacher who told you what you could or couldn't be? And all of a sudden you kind of start to realize that you've been maybe painting a picture of success that is either outdated or not your own. But it's hard to discover that. And so discovering that like this ambition of mine was coming from a place of anxiety, feeling behind it wasn't necessarily I didn't like what I was doing. It was I didn't like why I was doing it. So I like to differentiate. And you guys, anyone listening can do this right now. I call it the purpose test. And when you take the thing that you're so desperately want that you're chasing, Maybe it's a 1% top rated podcast, maybe it's a title at work or a project that you want to be on, imagine that thing that you're chasing that you got it. It was yours. But you had to remain anonymous. No one knew it was. You couldn't talk about it, you couldn't post it on LinkedIn. You couldn't do any of those things. Would it be something that you still pursue? It's a good gut check to help us recognize, like, are we doing something for approval or perception, versus are we doing something based off of interest or impact for ourselves where we don't need to be recognized. And so it's a good shift in one that I do quite frequently. And I also understand, you know, most of the time I speak at, like, companies who are like, okay, Jess Kuna, Matata. But we have to, like, get, you know, awards and external and money. That's all helpful. And I'm not saying that that's not something we shouldn't pursue, but when we confuse those with finish lines, that's where it gets slippery. Yeah.

Nicole Kahlil (12:11)

And I'll just circle back on if that's why we're doing it. If our metrics and our results are the predominant reason that we're doing something, we may have to question our motivations, whether or not sustainable. As you were talking, it's really speaking to, you know, I have a default that I get stuck in my numbers. It's really crazy how I can, even though I'm very aware that I do it, can so quickly go to, you know, at the end of the year, we were pretty close to 2 million downloads for the year, and that felt like a huge achievement. But it's just an arbitrary number. But I turned myself inside out. I ruined my New Year's Eve because I thought we were gonna fall 200 downloads short. I was focused on the 200, not the 1,000,999, 800, whatever, like, and in full transparency. I don't know how I would answer that question if I did it and had to remain anonymous. That's a good one to sit with.

Jess Ekstrom (13:07)

And it's. It's really. I mean, you bring up such a good point where, you know, our brain is wired to focus on the negative because survival, it kept us safe. Like when we focused on threats or we focused on things that didn't go well. But now it's like, man, that's super shitty that you had so many downloads. That is amazing. And you're like, oh, we didn't meet, you know, this 200 short. But one kind of like, reframe, if I can give you one, Nicole, because it's something I do as well, is I think a lot of times when we have something we want to hit that's in our future that is, like, something we haven't made yet. It's really easy to feel like we're at a deficit because, oh, it's in front of me. I'm not there, so therefore I'm less, therefore I'm behind. When really, I mean, you look at, like, some of these people who I. I like to, like, look at athletes. You have, like, Caitlin Clark or Serena Williams, or. It's like, they don't really have something that they haven't accomplished yet. Like, they have, but they truly love the game and it keeps going. So if you love podcasting, or if you find a way to truly connect and love what you're doing, then the ambition becomes more inspired. Ambition versus anxious ambition. Anxious ambition happens when we're working from a place of feeling behind or feeling less inspired. Ambition works from a place of progress and interest and impact. So it's not a, we know we're whole, but this is fun to do. But when it comes to a job, you know, sometimes when you're at work, it's funny. I was giving this talk at Kraft Heinz, and this woman was like, this is great, but sometimes I'm like, this is just ketchup. You know, like, how do I love ketchup? Like, I'm not saving the world. I was like, this is such a good point. Did you ever read the book Marie Kondo Spark Joy? Know where it was, like, decluttering, but

Nicole Kahlil (15:16)

of course I've heard.

Jess Ekstrom (15:17)

Yeah, but it was like a whole 2020 phenomenon when we're all stuck inside. So in that book, you know, she talks about, like, taking your items like, I'm holding my water bottle. Does it spark joy? And if it doesn't, then you get rid of it. But with the asterisk of. There are some things in our life, like a hammer or stapler, where it's not sexy, it's not exciting, but it. You need it. You know, they don't necessarily spark joy. And so she talks about taking the hammer or taking the stapler and thinking about, like, what does this help me do? Like, the stapler itself isn't exciting, but, oh, my gosh, this is how I stapled the papers that. That sent to my lawyer to where I sold my first company. Or this hammer helped me put together my daughter's dollhouse. That was really exciting. And so in this woman's scenario, yeah, maybe the ketchup isn't exciting, but think about the people sitting around the table having dinner with their kids, squirting ketchup on their plate, eating French fries, like, that's exciting. So I know sometimes it's hard when you're thinking, well, I'm just at a job. I'm just doing this. But there are ways to connect the quote, mundane or ordinary, with the extraordinary outcomes, even if you're not present to see it.

Nicole Kahlil (16:40)

So to that woman, at least in our household, she is saving lives. Because my husband is obsessed with ketchup. It is a problem. And then secondly, too, I think, yes, everything you said. And sometimes our work isn't always about the product. It might be the people you interact with or the way you can be a leader or the impact you can make on a coworker. I do think we get so focused on the outcome that we forget the people, the process, all of those things, all of it.

Jess Ekstrom (17:13)

Even innovation, you know, it's like, all of the things that I done or started, whether that's writing a book or starting Mic Drop Workshop or Headbands of Hope, started with something bad. You know, it was, oh, like kids aren't feeling good about themselves after losing their hair to chemotherapy. I'm gonna start having an oh. There is very few women represented on stages in these speaking spots. I'm gonna start my Drop workshop or, oh, I'm really struggling with this topic. I'm gonna write Making it without losing it. And so I think it's important to remember that sometimes motivation, inspiration, all these things that are kind of fluffy and good, start in the hard, and so pay attention to it. I call it inspiration from frustration. Like, most of my best ideas were times where I was like this. Like, this is just, why isn't. Why aren't there more women on these stages? Like, women have great things to say or why aren't they getting paid what men are getting paid? And that's how Mic Drop Workshop was created. And so I think that hard times give us a choice. They can be the excuse as to why we do less, or they can be the reason as to why we do more. And so we have to pay attention to those times instead of waiting for, like, the bright, fluffy aha moment.

Podcast Host 1 (18:34)

Like most moms, there's one role in my household that I definitely didn't apply for and would not be at all upset if I got fired from. And that's director of all information in the known universe. Like, what time is practice? Who's driving? What time will you be home? What's for dinner? Did we run out of pickles? I mean, the question game feels endless. Until now. Because now Our Skylight calendar is sitting on our mudroom counter where everyone can see it all the time. Which means I am no longer the human calendar reminder app or information keeper. It syncs with Google, Apple, Outlook, all of it, and puts everything the answers to oh so many questions in one place so everyone knows what's going on without having to ask me. And for that reason alone, I am obsessed. Because all families are better when they're working together. And right now, Skylight is offering our listeners $30 off their 15 inch calendars by going to myskylight.com womanswork go to myskylight.com womANSwork for $30 off your 15 inch calendar. That's my s k y l I g-h t.com/womanswork

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Nicole Kahlil (19:57)

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Nicole Kahlil (20:08)

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Nicole Kahlil (21:17)

I feel like sometimes we believe that success means we feel happy, content, secure all of the time. And I have yet to meet any person with any measure of success that has experienced anything even close to that. It's more. What you said is the heart is still there. It's just, you do something with it.

Jess Ekstrom (21:41)

You.

Nicole Kahlil (21:42)

You allow it to motivate you, and that doesn't make it suck any less. Like, I know that failure fuels confidence. I know this.

Jess Ekstrom (21:50)

Yeah.

Nicole Kahlil (21:50)

And so in our version, or resistance, our avoidance of all of the hard things, sometimes we're missing our key motivators.

Podcast Host 1 (21:59)

Okay, so if we don't have the

Nicole Kahlil (22:01)

most healthy relationship, or I'll just say, if I don't have the most healthy relationship with motivation and success, talk to us about how we build a healthier relationship. What does that mean? What are. What does that look like?

Jess Ekstrom (22:14)

So, first, recognizing that success is an individualized feeling. Success is not what it looks like to others. It's what it feels like to you. And so I think noticing the times where you feel successful, that might not be a certain bank account number or a certain outcome. It could be when you were, like, working with a team and it was really fun, or it could be when you were just in a coffee shop planning all the episodes for your podcast. It could be when you created enough flexibility to be able to pick up your kids from school. And so success is just an individualized approach. But it's really hard to know that when we're constantly surrounded by these tiny squares of the Internet telling us, well, success looks like a free trip from Tarte Cosmetics to, like, Maui or whatever. And you're like, oh, should I be, like, on a free trip to Maui? And. And so recognizing, like, what does success look like, feel like to you? Which, again, the book can help you with that. But we also have. It's called a Success Fingerprint Coach, and it's a custom, like, AI Coach that can walk you through it and put together a snapshot at the end. So you get that when you get the book. But I think also realizing that it is a constant effort that is revisited seasonally. And so you can't just be like, well, this is what my success is. Two years ago, I was looking back in some old journals or something I was doing, and it was like, I'm gonna have a Netflix show that, you know, does this. And I'm like, I could not think of anything less that I want today than a camera crew in my home. And. But I was gung ho about that two years ago, and I'm like, absolutely not. So I also refer to this artist method called pointillism. I'm not crafty at all, so bear with me. But pointillism is this painting technique where they put a bunch of dots on a canvas and when you're up close, like, you're like, why are there just a bunch of dots on this canvas? But as you zoom out, you realize that the dots actually make a painting. And so I like to think of my life and my success as all these individual dots on the canvas. I'm not living and dying by one accomplishment or one failure. It's all the collective. And so every once in a while we have a moment. Maybe that moment is right now where you can just look at all the dots on your canvas and ask yourself, do I like the picture that it's painting? Like it's not about the dot that happened three days ago or like, you know, getting laid off from your job or even a positive, like getting a bestseller or something like that. It's what it's all painting at the end of your life. Do you like where that painting is heading? And so I think it's just like taking time to be like, okay, what is my, what is that looking like right now on my canvas? I'm asking myself that a lot now. Becoming a mom. I have a one year old and a three year old and like my canvas is looking a lot different than it was four years ago, I'll tell you that. Nicole.

Nicole Kahlil (25:34)

Yeah, yeah, no doubt.

Jess Ekstrom (25:36)

Yeah.

Nicole Kahlil (25:38)

Okay. I want to circle back on that, but before I do, I love this concept of zooming out and that each dot, I think sometimes we think each dot matters so much more than it

Jess Ekstrom (25:49)

does so much weight and it doesn't. Yeah, yeah.

Nicole Kahlil (25:52)

So my question is around how important or is it important to celebrate and acknowledge when we zoom out? I think so often we're focused on the next dot that, yes, we zoom out. Okay, first of all, none of us are doing that. We're not zooming out. We're not looking at the bigger picture. So step one for sure. And I, I get to do that myself too. But when we do it, how important is it to acknowledge, to celebrate, to notice what's beautiful and, and if it is important. Any tips on how to do that?

Jess Ekstrom (26:25)

I think I'm gonna give you an example of last night. My husband was building a compartment for our shoes. Cuz our living room is just like a dsw. There's just shoes everywhere. And you know, my three year old really wanted to help him. And of course, having a three year old with heavy tools and a task that could have taken an hour is now like Three hours. Because she's like, let me help you screw this in. And I could tell, you know, he really wanted to get it done, but he was letting Ellie help. And when he was done, I remember before we even had kids, I remember, like, we were talking about what kind of parents we want to be and him saying that he really wants to, like, have kids, like, be involved in anything that he's doing. He wants it to just be, yeah, come with me to, like, you know, paint the door. And even if it takes longer. Like, I remember him telling me that before we had kids, and so after they were done, and I could just see, like, the stress on his face of, like, how long that took. I was like, I just want you to realize that you just did what you said four years ago that you wanted to do as a dad. And he was like, oh, my God. Like, you're right. And so I think sometimes it's doing that for ourselves, but also seeing that in other people, which is one of the things I'm trying to work on. This year. Our team is growing at Mic Drop Workshop, and I'm trying to figure out, like, what's my role as a leader if I'm not the executor, you know? And I think that my role is, like, helping people realize how far they're coming or what they're doing. And I find that those moments, when I do that for others, it also allows me to do it for myself. You kind of turn that part of your brain on, so I almost wonder if it's helpful for anyone listening. It's like, recognize someone else in their canvas and how far they're coming and then see if that also gives you permission to do that for you.

Nicole Kahlil (28:28)

Yeah, I love it. It's like building the habit in a little bit of an easier way. I think we are better at seeing and acknowledging the accomplishments and the people we love and. But if we're building the habit, I don't know why this triggered the thought. I often do when I'm making a hard decision or things feel murky or scary. I often ask myself, what would I tell jj, my daughter, if she was in this situation? Or what would I want J.J. to do? And it helps me think of what is the best, boldest, best, you know, most courageous thing that. Because that's what I would want for her. And I wonder if even the flip side of, like, what would I say to JJ in this moment when she creates success in this way or puts that dot on the picture? I often think about it in the when I'm in a tough situation. But I wonder if I thought about it in the positive, like, if she achieved this or if she got to this moment, or if she was experiencing this thing, what would I want for her? And then do that myself. Okay. We hear a lot about success and sacrifice as if they're coexisting, one's necessary for the other. And I wouldn't go so far as to argue that sacrifice isn't part of achievement or success. But your title is making it without losing it. So making it without having to sacrifice everything. And then you mentioned, you know, being a mom, I think for a lot of us, it. We often feel the trade off is either personal success at the sacrifice of professional or vice versa. So long winded way of asking, how do we make it without losing it?

Jess Ekstrom (30:16)

Great question. Do you have three hours? I'm just joking, but I know this is a shorter podcast, but I think it's one understanding that we don't always have to trade productivity for peace. I did something like when we were trying to think of, like, how do we say who this book is for? And my team, we came up with these, like, things that we know that I do, that go getters do. Or it's like if you've ever raced against the microwave to like complete a task, or if you've ever tried to carry all your grocery bags at once just to like, prove that you can. And there's all these like kind of almost little competitions that we have with ourself. And so I think that I always had this concern of, if I'm not anxious, does that mean my ambition goes away? If I'm happy with myself, does that mean that I'm not reaching towards a future? And I went on this retreat one time. There's a lot of answers to this, but I'll. I'll give you this one that I think was interesting. And there was like this facility. It was a silent meditation retreat, which I've learned I am not a silent person. But it was really, it was really helpful.

Podcast Host 1 (31:33)

Yeah.

Jess Ekstrom (31:33)

And the other kicker to it was I didn't read the fine print. And I got there and the theme was death and dying, which I talked about in the book because it was like one of the first times I ever thought about death, you know, in a weird, weird way that we really avoid it in, like, our culture. But anyways, so I asked this question to this. His name was David Shirkanov. And he said, do you ever see an acorn and think, well, that's not an oak tree. He's like, no, you think you see an acorn and say, like, that's a great acorn, but you don't see it as less than what it could be, which is an oak tree. It just needs the right causes and conditions to get there. And so if you see yourself as the perfect acorn, you have all of this untapped potential to be an oak tree. But that doesn't mean you're not a good acorn. You just need the causes and conditions to get there. And so I think of. I know this is very, like, Buddhist, or maybe not as hard hitting as what the podcast typically is, but seeing yourself as exactly where you need to be and exactly who you need to be, that doesn't mean that you don't have more in you and more for your future, but it doesn't mean that you need to feel less. Like wanting more doesn't mean that you're less. And so I've actually, like, really enjoyed building, almost like I'm a kid in a sandbox instead of like a banker on Wall street, you know, it's like, oh, I wonder what this, like, could look like and wonder what, how this could feel if I build it this way. And I also understand that there's privilege that comes with being, finding work that you enjoy because there's work that just has to be done. But I do think that there's ways to infuse a groundedness and contentness, no matter if we love our job or not. I know that was a really long answer.

Nicole Kahlil (33:47)

Yeah, no, it was a great answer. And the acorn analogy, I think sometimes too we forget that an acorn doesn't become a full grown oak tree from one day to the next. There is evolution and growth and time and. And I think often we are very binary. It's either we're the acorn or the oak tree, and we're just pissed in the in between, as opposed to acknowledging that all of those things take time and growth and. Okay, so my last question though, is especially for women, I think we fall under the comparison and competition trap for sure. Let's just add social media into the mix. It's really hard to be like, yeah, okay, great, I'm an acorn, but somebody else is a better acorn, or they're a little further along or they're bigger, whatever. Any tips for unraveling your own individual definition of success and healthy motivation from everyone else?

Jess Ekstrom (34:49)

Yep. Something I struggle with a lot. And I've had a love hate relationship to social media because of it. Couple things that I would say. One, recognize you're never seeing the full story, period. Two, I think I used to see people, like, doing things that I thought I wanted or could do and I would almost resent them for it. Or I'm like, well, I want to have a, that speaking gig or I want to have a best selling book. And. And instead of being happy for them, I was resentful and felt less, maybe unfollowed them or something, you know, super immature. And now I see people doing things, especially women, that maybe I could see for my future. And I think, oh, that's so great because that means it's possible for me. And so instead of thinking of comparison as what you haven't done, think about it as proof and evidence that it could be there for you. And I found that the more I step into a place of genuinely cheering for people, not the fake, like, you got this, mama. Like, it has helped me have a better relationship to comparison when I truly believe that I want to see other women win. Because I also think it as just, I can say this on this podcast, like, points on the scoreboard for women. Like, let's just keep gathering points that we can do this, that. And so I just think like, oh, good, I'm so glad that maybe a young girl like, you know, the Winter Olympics were this year. Like, I had my daughter, you know, watch all the women's hockey team. Lindsey Vaughn, even though it didn't end the way she wanted to, I, I'm like, oh, just let's watch women do good things and big things because it's points on the board for us.

Nicole Kahlil (36:50)

Yeah. And that reminder that we're not always ever going to be the ones scoring. And so when we are cheering or passing or being a good teammate or whatever our role is at any given time, it allows for all of us to play a bigger game. Couldn't agree more. And I for one appreciate that you're out there accumulating points for us and cheering us all on. For you, the listener, a reminder. Jess's book is called Making It Without Losing It. Go order it right now on Amazon or go to your local bookstore. Let's keep them in business. You can also find more about Jess and her work, including her Mic drop workshop on JesseXtrom.com. also follow her on LinkedIn. She is cool on LinkedIn, which sounds like an oxymoron, but it is in fact the truth. So, Jess, thank you for your incredible work and for being here today.

Jess Ekstrom (37:46)

Such a great conversation. Thanks, Nicole.

Nicole Kahlil (37:48)

My absolute pleasure. All right friend. If we are never done, if we are constantly growing, learning and evolving until we take our last breath then we have to stop waiting until we are done to feel worthy. We don't get to keep tying our value to the next milestone and then acting surprised when peace never shows up. We don't get to demand motivation while refusing to acknowledge everything it's already helped us build. Maybe making it has nothing to do with reaching for some imaginary finish line. Maybe it's about noticing that you're already standing on ground that you once prayed for. Ambition is not the enemy but anxious. Ambition will run you straight into the ground if you let it. So build, grow, chase what matters but never light yourself on fire just to keep everyone else warm. You are allowed to succeed and feel good at the same time. Fuck the moving goalpost and feeling worthy before the finish line. That is woman's work.