I just got the inc 500 nice email, founder.
Exactly my reaction cool.
Five minutes later i was like well, that didn't solve all my problems.
Here we go to the next thing not to say that like those things shouldn't be like celebrated applauded, and not to say that you shouldn't want those things, but if they are like your primary driving force, then it's probably knowledge to receive that you're going after things based on how they look instead of how they feel.
If you still would go after it with no one knowing, then it's a really good indicator that your compass is well calibrated.
Go for it.
You're not where you want to be yet.
And somewhere in the back of your head there's a voice that says once I get there, I'll finally be OK.
But what if that voice is actually the problem?
Jess Ekstrom built two companies, wrote two books and learned the hard way that none of it feels the way that you think it will until you change the goal.
She built her first company, Headbands of Hope, from 0 to millions in revenue, and her new book, Making It Without Losing It, is the roadmap she wishes she had at the start.
Here's what we'll get into today.
The false summit trap.
Why the goal you're chasing will almost certainly reveal a bigger one behind it.
Why your problems right now are actually proof that you're in the game, not proof that you're behind.
And how to build a definition of success that is actually yours, not the one that you borrowed from someone else's highlight reel.
If you're still in the climb and you want to enjoy the journey without losing your drive, this episode was made for you.
Let's jump in.
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Even though you have made it, you still have such a deep level of ambition.
So what is it that pushes you?
Because that's one of the key themes of the book. right?
The importance of ambition and balancing at the same time.
But by most objective metrics, all reasonable objective metrics, you've made it.
You and your husband, you're good, you're doing well, but still pushing for more.
So tell me about your personal relationship with that ambition that is within you that drives you forward.
I remember the day it started.
I was in middle school.
My parents signed me up for a program called Outward Bound.
And it's like where they throw you in the woods and call it leadership.
So I was like, Mom, Dad, I'm more of an inward bound kind of girl.
I don't really want to do this.
They were like, no, you're going.
And so our instructor took us on this hike one day and said when you get to the top of this mountain, everyone in the group is going to get MMs.
I was like, now you're talking.
And so we're going up this mountain, super steep.
I see the other kids in my group in front of me making it to this peak.
But they're not celebrating and they're not eating M&Ms.
And so I'm like, what am I missing here?
And then that's when I got to the peak.
Or so I thought I got to that peak, only to see when I got there that there was a whole other peak that we had yet to climb.
And that was obstructing our view, the one that we were climbing.
So our instructor sits us down on this first peak and we're all just like tired frustrated, Eminem-less and looking at like, oh shit, we still have like so much more to go.
And he said he specifically took us on the hike to teach us something.
I was like, okay, Tony Robbins, I don't need a lesson.
I just want my And he's like, look, this is what's called a false summit.
A false summit is the belief that you're about to make it.
But then when you do, you realize that there's more left to go.
And it happens all the time.
I mean it happens when you hit a revenue number that you thought was going to launch you into this whole other like orbit of business ownership.
It happens when you move into a new house that you thought was going to solve all your problems.
It happens in you know, like if I can get my kid into this school or if I can hire this person, then I can finally be happy, feel fulfilled, be successful, once I can pay myself this amount of money.
And then the goalpost keeps moving.
The progress bar keeps extending.
And that was the moment that I realized what that was, was a false summit.
But it took me years into building my businesses Headbands of Hope, Mic Drop Workshop, growing them to millions of dollars to realize how that actually I hate using the word manifest, but how that manifests into disappointment all the time.
And in some cases, even becoming a parent, like depression.
Oh, there was this thing that I really wanted.
And now why am I not happy?
Because we put so much stake in the summit.
Like, I just want to get there.
But there was this really interesting study.
It was around dopamine and it was at Vanderbilt University.
And for so long we thought that we got that hit of dopamine, that like happiness chemical that we want, at the result, like in the payout, at the ribbon cutting, whatever it might be.
But the study showed that we actually don't get dopamine at the results.
We get it in anticipation of the result.
We get it in the process or we get it in the build.
And so making it without losing it in this book is really just this idea of like do we have to keep trading future ambition for present joy.
And the answer is no.
But it takes a lot of effort and a lot of rewiring to have them exist at once, which is what I'm working on and what this book is on.
This is great.
This is great because I think so many people can relate to this.
First of all, we can relate to our parents telling us to do something that makes no sense at the time.
Exactly.
You want me to go where?
Do what?
Yeah.
But then being annoyed at how profound the realization was like, oh, man, that's really helpful.
And I think about the mountains, too.
It's it's true.
We try to climb these mountains only to find another mountain.
Or look up and see somebody else on a different, bigger mountain and we say, oh my gosh.
And I think one of the things that I was trying to do I've started to do better is look back at my previous notes and things that I used to say in the past.
And I try to look at my life, not through my own present eyes, but I say to myself there's a version of myself that would be deeply grateful for the problems I'm experiencing right now.
And I remember going back and seeing one of my journal notes from 2016 when I started the business.
And I was like, man, last month I made $1,200.
And if I keep on going, I think I can do this.
I think I can make $2,000.
I'm like, that's.
Adorable.
Right.
And so I think about the things that make me panic today and make me concerned.
Like those are the things those are the problems I wish I would have had.
That's a good point.
It made me.
It makes me think about sometimes we make changes and in our mind we make changes to have zero problems, when we're really actually making changes to have new ones.
Yes, and for me, that was selling my first company, headbands of hope, which was, you know, your first business.
It's like a your first love.
I mean, it's just so ingrained in you.
It was who I thought I was.
I deeply associated my self-worth with that company, which is a slippery slope.
But when you know it was kind of it was such a do good business that it was conflicting to feel like I wanted to do something else because I'm like wait, but this business is so great.
But the way I was finally able to kind of wrap my head around it is when you are like reading a really good book.
And all the pages you already read you know are in your left hand and you only have so many more pages left to read in your right hand and you want to savor it, but you know that the book is ending.
And that's how it felt at my business, where I was like look at all this stuff that I've done in my left hand, all the pages that have been written.
I don't have many more pages here.
I don't feel like I'm the one to keep doing this, because when I thought about the problems That Headbands of Hope had,
Which was very normal problems for a consumer business.
It was supply chain.
It was fulfillment.
It was trends of hair accessories.
Things like that.
Those were not problems I was excited to solve.
But then...
With Mic Drop Workshop, which was what I really wanted to leave and go do, which was helping women get paid speaking engagements.
Those problems of equal pay, of how do I get information delivered in a way that people can absorb that makes sense.
How can I start a referral community of women speakers?
Those were problems i was excited to solve and so sometimes, like when we think about uh, a big change or a solve or moving or whatever it might be, realize like very rarely is there a change or a solution that brings zero problems.
It's going to bring new ones.
So are the new problems ones that you're excited to solve?
Because that's at the end of it is all this is.
All work is is problem solving, whether it's a new client, whether it's making more money, whether it's getting a better satisfaction rating, it's all problem solving.
So how do we make it so the problems that we have to solve are ones we're excited to solve?
That is so good.
That's so good.
You're absolutely right.
It's It's trading old problems for better problems, essentially.
And I remember one time I was chatting with Simone, our producer here, and he said that every solution comes with a problem attached.
And I think it's such a spot on.
It's such a great metaphor for life.
And then going back to what you said about the study from Vanderbilt, it's again.
Earlier you said oh, I hate saying manifest because it's kind of overplayed.
Well, I hate saying it's about the journey because it's overplayed, but it is an inescapable truth.
Because that study just shows scientifically that it is truly about the journey.
The dopamine is there in anticipation.
Then once you get it, the dopamine ends.
And so we have to find ways to find pleasure and enjoyment and purpose in the process.
I think back to Viktor Frankl, who wrote Man's Search for Meaning.
He was a Jewish psychologist living in Nazi Germany.
And so going through at Auschwitz.
So he's seen the worst of the worst.
And he said that when...
When he would see people start to fade and die, he said he could tell the moment when they broke.
And it was because they lost purpose.
You have to have a reason.
I forget the exact phrasing, but it's like if you know your why, you can survive any what or something to that effect.
And I think, when it comes to the difficulties that we all experience in life, if we can find meaning in our suffering, as he would describe, and find pleasure in the journey, which is what we always say then that's the path to sustainable ambition.
But if we feel like we are not okay until we achieve the certain thing, that's when it becomes very unsustainable, very toxic.
And for you, as you went through this, How were you able to make this shift?
Because, like you said, with Headbands of Hope, we can't just pass over this like this is some little you know nothing business.
This was big.
This was substantial.
And it was very tied to meaning, but also your identity.
How were you able to find wellness in that transition?
I'm not going to lie.
I lost my mind a little bit.
I distinctly remember getting the paperwork for the acquisition and just like laying on my bed and crying.
And it's funny because when I was reading the audio book for Making It Without Losing It you know narrating it there was tons of moments where I thought that I might get emotional.
I might get emotional, you know, talking about postpartum.
Or I might get emotional talking about, like a friend, that I lost work.
You know this scandal that my family went through.
But I got emotional talking about this acquisition of Headbands of Hope because it was such a not only was it tied to my self worth, it was also something that I singularly was focused on for a long time.
Was that like?
This was a finish line that I wanted to cross?
There's something called the post-achievement letdown.
Have you ever heard of it?
When you realize it exists, a lot of things start to make sense.
Michael Phelps and Simone Biles have talked about this in the Olympics, where it's like you train so much for one moment, one day, like one thing.
And then it feels, when it's gone, the kind of what you were saying, that kind of like purposeless, directionless.
Okay, that was something that I was so focused on for a long time.
It happens with weddings, it happens with like graduation or Stuff where you're like this is the day or this is the moment where my life is going to begin.
Retirement.
There's a lot of studies and research around depression and retirement.
And Because, once you get the thing that you've been yearning for or longing for, it rarely meets up to the vision that we had in our head.
And that can be really disappointing.
And so with Headbands of Hope and it getting like acquired or with anything that I feel like I had a one day, a calendar date in mind of once I get the Right.
Now it's our conference that's happening in two weeks where I'm really trying to get this verbiage out of my head that says once the conference happens, then everything's going to just magically be better.
Or we've had... Once our kids... We were talking about this before we started recording.
Five is the magic number with age.
Once my kid's in school, then I'm going to have no problems.
And I get that things change and they get better.
But when, like I call it, in the, in making it without losing it, like this arrival fallacy where we have this idea that there's going to be a moment, a person, a place or a thing that's going to tell us that we've arrived.
Because that's how we've been trained our whole life.
We were in school.
Oh, you're in first grade.
You did well enough.
Guess what?
You get to go to second grade.
Oh, you did so well that you get to go to college and now you get a job.
And here's, you know, in school, here's your report card.
Here's how well you're doing.
And so we've been conditioned in our most formative years to believe that we're going to know.
We're going to know if we're good enough.
We're going to know if we can go to the next level.
And we're going to know how we're doing from someone that's smarter than us.
But that's not how life works.
It's just on us.
And so things become more nuanced.
Like, am I doing a good job?
Am I where I should be in this life?
Do I have enough friends?
Do I have enough money?
And so all of this, like self-reporting, can be really confusing when you put it on a specific date or a specific time or a specific moment.
Because in that moment, it's going to come and go and it's not going to be what you imagined.
And so again, hate to go to what we're saying of like manifestation and the journey, but it really is about do I like myself in this process?
Do I like what I'm aiming or working towards?
Not the moment, but what I'm working towards.
There's this painting technique that i reference sometimes in my keynotes called pointillism.
I'm not like crafty or artsy at all, but i think it's interesting where it's a technique where people just put dots on a canvas.
It's just a bunch of different dots And when you're looking at it up close you're like this is just a bunch of dots.
But then after a while, when you zoom out, you realize that the dots actually create some sort of image like a face, a landscape or something like that.
But it was just the process of a lot of little dots.
And so I think of like Everything in our life, every decision that we make, every moment, everything we don't live and die by one of it.
Everything is just a dot on the canvas.
And so every once in a while, we can take a step back and ask ourselves do I like where this is heading?
Do I like where it's going?
Do I want to change shape?
Do I need to swap out my brush and try something else?
But when we put so much weight in like one single dot, we're missing the whole picture.
You're so right.
This is brilliant.
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What I'm going through.
Right now, as you're saying this, I think it's just entrepreneurship in general.
It's just really tough.
It's just really heavy.
And just recognizing that you have the capacity to handle what it is that is put in front of you.
If you just handle what's in front of you, if we widen our aperture too much and we think about the whole picture, then it feels really heavy.
So, for instance, if you just look at your whole career and then you say oh my gosh, this speech could make or break my career,
Everything is riding on this, because if this doesn't happen, then that doesn't happen, then that doesn't.
And so then the moment feels heavy.
But then if you just focus on this micro moment, this one dot in the picture, then you could say OK, my job today is just to make the best dot possible.
I don't need to worry about I can have an idea of what the big picture is.
But once I get clear on what my dot needs to be, my focus needs to be on that dot.
And and what's really tough though, is that our emotions change will cause us to focus on things that are maybe urgent but not important.
It can shift our perspective in a way that's detrimental to us.
And what's interesting is I was talking to my son about this is that there are some people who are so smart that they're actually dumb.
He's like, what does this even mean?
And I said, there's a difference between being smart and intelligent.
An intelligent person understands the goal, the destination, and they do whatever it takes to get there within ethics, within the ethical bounds, of course.
But a smart person is known for thinking.
And then they think thinking is the destination, when it's just one of the many tools that you use to get there.
And so sometimes you get into this, This pattern of just thinking and then thinking, about thinking, then thinking about the consequences of those thoughts.
And then it just becomes incredibly overwhelming.
And then you blend that with the fact that, even if you're a high achiever, we become a high achiever early in our life, by understanding the game, playing by the rules, winning the game.
According to what some arbiter of truth has told us that success is.
Then, once you get out into the real world especially again in entrepreneurship, where you start to blaze your own trail, it's like who is the adult that's supposed to tell me what to do?
That's me.
Is this good enough?
Then you start looking at other people to see if you're good enough.
And then you start trying to compare yourself to them and win on their terms, not your own.
And then it gets really messy really quickly.
There's like it's so true, and there's something called um.
I talk about the success fingerprint because it is so easy to say well, kwame has like a top one percent podcast.
That should be me, like that's what i should do, or so-and-so is launching a you know mastermind, this like then clearly I should do that.
And very rarely do we think of success as like individualized, because we live in a world where it's like trophied everywhere on display.
And so we think that we need to match what's out there.
And so in the book I go through, like all the steps to make your own success fingerprint, like what's important to you.
Where do you want to spend your time?
What are like these life buckets that you're contributing to in this season?
Because that's another thing is that there's a seasonality to it.
Like you and I both have kids and sometimes in different phases.
Right now, you know, I have a one and a three year old.
So success looks like how do I make more time?
Maybe not how do I make more money?
But how do I make more time?
But five years ago, it was, yeah, sure, I'll go on a plane for whatever and stay for three days.
And now I'm just like, how do I get the first flight in, first flight out, and be back to my family?
And so I think, going back to like pointillism in the canvas, very rarely do we audit our life without disaster.
Usually it's, a diagnosis there's a something that you know maybe there you get laid off maybe there's um you know something like grief that happens and you kind of take a step back and you're like hold on well i'm you have this kind of jolt of like what am i living the way that i want to live because you realize either how life is short or that the rules don't always work.
And you could just kind of wait for something bad to happen to wonder and realize if you're doing what you want to do.
But what if we didn't need that?
You know what, if we didn't need to wait to like for everything to crash and in order to think am I building what I want to build?
Am I doing it in a way that feels good to me?
And have I...
I also don't like using the word balance because I think sometimes that's just like a load of shit.
But am I giving the attention to the things that I want to give attention to?
And that's really what I think a lot of this is with success is taking the time to audit without the crisis and yeah, knowing like, oh yeah, this is, this is working for me or this isn't working for me and what do i need to change.
But having the awareness to audit without the crisis is like a learned skill.
Yes, and i, and again, it takes time and one of the things that I've recognized Jess, is that once you get to a point where your needs, your base needs, are met, that gives you the opportunity to ponder these types of things.
Because we didn't have the luxury of being able to think like this When we were just constantly grinding.
It's like I got to put food on the table.
I don't have time to ponder about philosophy here.
But now we have the privilege of being able to do that, which creates another challenge.
It creates these micro existential crises within our life where we're like, who am I?
What do I want to do?
And I think, when it comes to happiness and success, One of the main things we have to do is give ourselves permission to adjust and adapt.
Because, like you said, with those audits, if we start to recognize, hold up.
I change and evolve every time there's a crisis.
Why don't I just do that all the time as necessary based on the circumstances?
Then I can kind of steer the ship and make these micro adjustments.
So maybe I start to avoid some of these crises. before they happen.
And one thing that I've been doing recently to kind of help me understand this a little bit better is thinking about it through the lens of character, but not character in the kind of moral sense, but character in the I'm watching a movie.
This is my favorite character type of sense.
So it's like okay, if i'm watching the movie of kwame and and i'm, i am the main character.
Everybody else is the main character of their life.
We want to respect that, but i'm watching my own movie.
What do i want my my character to do?
Wow,
Hey, my character right now has potato chips on his chest looking through Instagram when there's work to be done.
This movie stinks.
Okay.
I need it.
I love that.
Do something, you know?
Or this, whoa, what do I want my character to be like?
His kid just came in the room and he brushed him aside because he had more work to do.
Is that the movie I want to see?
No, and then recognizing oh this, my character will shift from time to time and, like a real good character, has depth and nuance and the ability to adjust.
So there will be a season for everything.
So there might be a grind season, but we've seen entrepreneurs, we've seen friends where the grind becomes their identity.
It's like do you, is this even who you want to be?
And I think that's a question we don't even ask ourselves, because so many times in life our decisions are dictated completely by circumstance.
So some fire happens.
I guess I'm a firefighter today.
And we put out fires so much that we think that's who we are at our core, but we don't take the time to analyze who we want to be and what changes we could make to put ourselves on the path to find our.
As somebody said, what is it?
The fingerprint of success or success fingerprint.
Understanding that your character, your success fingerprint will look different than other people.
Do you want a really morbid way to do this?
Ooh, delightful.
Yes.
Write your obituary.
True.
Like, what do you want people to say about you after you go?
And I know like in our culture we don't really talk about death, but I think it's if we want to talk about life, then we got to talk about death.
And so much of like success is, and how we talk about it today, as if this is all there is, you know, as if like nothing else matters.
But we all have a clock that we don't know the time.
And so if, you want to wonder how do I want to live?
Well, what do you want people to say about you when you die?
And so I think about that a lot, like a lot, a lot.
I actually went on a retreat, like um, before Ellie was born.
I'm not like a meditation person, but I had been curious about going on a silent retreat, like what would it be like to just not talk for four days, and so I signed up for one.
And I don't even know, have we talked about this?
No oh okay, yeah.
So I went to a silent retreat And when I got there,
I kid you not.
I just signed up.
I'm not a fine.
Like look at the detail.
Or a fine print person.
And it bit me in the ass.
Because I got there.
And the theme was.
It was a silent retreat.
But the theme was on death and dying.
And I was like.
I'm just going to get my car and leave because this is not where I want to be.
Uh, made me super uncomfortable, but Kwame, it was what I didn't know that I needed.
Like I needed to look death straight in the eyes and and know that it exists for myself, for my parents, for everyone.
And we think that it, and of course it's sad, and of course it can be morbid.
But it can also be like really, oh, does this really matter?
Like this, that I, you know, used too many exclamation points in this email, or whatever we want to say.
But yeah, it taught me a lot about how I want to be remembered and also what I'm building to last beyond me.
In the book, you know, I talk about, I don't want to just achieve goals.
I want to outlive them.
So what is it that I'm creating today that's going to impact my daughter and her kids, or my son's kids, after I'm gone?
And for me, that's equality in women's pay.
That's women getting the chance to speak.
That's women getting thought leadership opportunities.
That can live beyond me.
So it's an interesting thing to like think about, like how, what is my obituary and what are goals I'm working on right now that will outlive me?
And that ties back to purpose.
Right.
And and the thing is, everybody has a purpose.
I was talking to.
I was speaking in San Diego and I was talking to the bartender and he was saying it was a really cool philosophical discussion we were having.
And he's like, I'm sorry for talking your ear off.
I just I was like, this is I love talking to people.
So this is great.
And and he says, yeah, these ideas, I don't think people want to hear it.
I said, I'm I'm here.
I'm hearing it.
That's good.
And so he's because he said, I just keep to myself.
I said well, you know the things that you believe, the things that you have inside of you.
It's important to you.
There's it's possible that there's another you out there who just doesn't know that you exist.
And even if it's one person, that is meaningful.
And so I think a lot of times we get caught up and we think that a purpose needs to be something like massive.
Your purpose, your legacy, it is what it is.
Whatever you want it to be, it can be.
And as long as it's meaningful for you, that's what matters.
And you have a big why.
And the thing is that that legacy will live through your children too, because they're going to be watching you.
Because you're not just fighting for women's equality and helping more women get paid not just paid, but paid what they deserve when it comes to speaking, so their message could be heard.
They're also seeing you do that.
So you shining and being successful in your way is going to be really powerful.
But, at the same time, doing it from a position of wellness.
I think that's one of the things that is going to be a part of your legacy that people would really admire.
Okay.
Let's talk about purpose for a second, because I think we could have a hot take on this, or at least I have a hot take that I've been recently is, I think like, find your purpose is kind of a load of shit because it is gives people this idea that they have to like stop what they're doing and find a job or create something that is inherently like live laugh, love.
And i think that there are a ton of people that haven't found purpose but have created it in a job that maybe isn't inherently seen as purposeful.
Yes, so i mean like i just the there's a guy at my gym who cleans the equipment, but when i'm there and he's cleaning the equipment, he's also counting my reps.
Like he sees, if my water bottle is low, he's gonna go fill it up and i go to the ymca i'm not going to like soul cycle or something like fancy and He has created purpose in his job.
That's cleaning equipment.
And so I meet a lot of people that are directionless, feel purposeless, that think the answer is a change of job.
And don't get me wrong.
Sometimes it is.
Sometimes you do need to change a job.
But I do think that there is a, like, a fallacy around that.
Because I've rarely met someone that's like, well, I changed and so much better.
Usually they're sitting in the same position that they were before.
What do you think about that?
No, 100%.
I think about.
That's the same way I describe like People who say finding yourself, you have to find yourself.
You have to create yourself.
You are built.
Purpose in the same way is built.
And so it has to be within your, again, authentic self.
So a lot of times what people recognize is they're living an inauthentic life.
So then they have to change.
But then some people think that change is going to bring them the purpose that they want.
But then they don't realize that it is a perspective shift that needs to change, not necessarily something tangible within their life, you know.
And so when it comes to purpose, I agree.
You have to create it and it's going to look different for different folks, too.
Yeah, I just interviewed my mom on my podcast, which was really, really cool.
But she did not, you know, I wouldn't call her someone who had a career.
And I didn't realize that that was something she felt a little like insecure about or self-conscious about.
Until I got an email from her one day years ago when I had just started Headbands of Hope and it was the first time we had gotten on like the local news and they did a segment about a hospital delivery that we did.
And she sent me this email like two in the morning.
It was like you know.
For a while I wondered what my purpose was like, why I was here and what I was doing, and if I was doing enough.
And she was like.
Now I realize my purpose was to create two kids that are going and doing the big things that I didn't do.
And she, we just talked about this on the podcast.
Cause she's like, it was like this light bulb of, it wasn't something I had to go find.
It was something that I, you know, created through, in her case motherhood, but there's so many different scenarios or like people that I see.
I mean, For example, I worked in Disney World before I started Headbands of Hope.
That's where I got the idea. but uh you know you have to show up to disney this was through the disney college program and they give you your role um and you don't know like what it's going to be you just have to commit and they're like you're working in this ride at this attraction in the magic kingdom and um so there was a lot of excitement and a lot of disappointment from people And there was two people that I knew that both had custodian roles.
And one of them, she was like, I hate this.
I'm literally picking gum off of benches and picking up trash off the streets.
This is disgusting.
This is gross.
And then the other guy who had the exact same job was like, I get to be outside.
I'm the person in the streets that people get to ask, what ride should I do next?
Where should I go?
Can you take my picture?
This is the coolest job ever.
And so it was kind of the first time I saw up close two people who had the same job, with completely different experiences and how they look at it.
And one found purpose or one created purpose and the other was looking for it.
Yes.
So yeah, I just think the purpose discussion is so interesting because I see a lot of people Almost like waiting to flip over a rock, when sometimes it's just created around where you already are.
I agree.
I heard a story similarly with a custodian at a school.
And in his mind he's like I'm creating an environment where kids can learn.
If it's messy, they can't focus as much.
So I'm an integral part of the education process.
That is so true.
My friend, Megan Riley, I don't know if you know her.
Um, she would also be awesome to have on the show, but she was on shark tank.
Um created this awesome company, but she played basketball in college and she um quit the team because she wasn't getting any playing time.
Like she wasn't good enough, but she was on the team, but she wasn't getting any playing time.
And it took her years to realize like her spot on the team was the encourager, not the player.
Like she was an integral part of the team because she was so encouraging to the people that were playing.
But she got caught up in saying like, well, I'm not out there.
I'm not getting any playing time.
So why am I spending all this time at practice?
And so she quit until she realized like, well, that wasn't my role.
My role was encouraging the people that were playing.
And so it's just such an interesting way of like how we can all find some I like to call it and making it without losing it.
And when you're extrinsically motivated, you do a lot of box checking like I'm doing this, I'm doing that, I'm playing, I'm that.
And when you're intrinsically motivated, you're connecting the dots.
You're recognizing what I do is connected to that which is connected to that which is helping this person.
And so when you go about your day or you look at kind of your role and how you think about your work, is it box tracking or are you connecting the dots?
Because those are like two different types of motivation that we pull from.
You know, I wonder, because this is I agree with what you're saying.
Um, i'll tell a quick story and then bring it back.
So i'm a, i love tennis.
Tennis was my my favorite sport growing up.
Um yeah yeah, it's.
Uh, did you play recreationally?
I'm not arena Williams over here.
But yeah, but I love tennis.
And I remember one time I was watching a match and it was a very it was the pros playing and it was a really close match.
And one of the players got what he thought was a bad call.
Crucial point.
Final set of the match.
And he just lost it.
Just lost it and was yelling at the ref for like minutes.
Not just like, hey, I disagree, but minutes.
And one of the commentators said something really interesting.
He's like, he's going to lose this match because I think he's looking for an excuse.
And I wonder, when it comes to these conversations about purpose and it being created, not discovered, if this is a scary message for people because they want an excuse.
Because the reason I feel unsatisfied, the reason I feel unhappy and unfulfilled, is because of the circumstances.
I've been looking for purpose, but I have yet to find it.
But if we now know that we have the power to create purpose in whatever circumstance we're in, then who can we blame for feeling purposeless?
Yeah, that is profound.
And I will say, you know, sometimes And circumstance can play a role, I think when you're talking about risk,
You talked about this before.
When I started Headbands of Hope, I had a net to fall into.
I was never worried about if this doesn't work, what's going to happen?
Am I going to have to – where am I going to eat?
Where am I going to sleep?
That was never – crossing my mind, and so therefore, i could take big leaps, i could make big swings, because the aftermath wasn't detrimental, but then there are times in our life where it's like there's.
We point to lack of resources, when it's really lack of being resourceful.
And I feel like the further along I get in my career, it's almost like you think that collecting more data is going to make you more resourceful, when really sometimes it highlights what you don't have.
You know cause you have so much more.
Well, they have a whole studio that they record their podcasts in.
Like I should do that.
When I was first starting out, it's like, I was just looking at what I had.
Oh, I have, they do a free domain over here.
Like, let's do that.
And and And so sometimes it gets harder.
The more you, the further you go to be kind of that scrappy and, like resourcefulness, that underdog, because you think you need to be the champion.
There was actually a this example I give when I speak, do you know do you follow world chess Kwame?
Oh, yeah.
You're talking about... I told you I play chess, but I don't follow the competition.
Wait, do you really?
I didn't know that.
I'm learning about tennis.
Are you for real?
I'm learning about chess.
Yeah.
Yes.
It's honestly an addiction that I need to work on.
I played on chess.com over 26,000 games.
I got up to the 99th percentile.
You're probably going to talk about Magnus Carlsen and stuff.
Magnus carlson yes, love chess.
Okay, you might be the only, and there's like a netflix documentary coming out about him, which it used to be this name whenever i would say it.
People wouldn't know, but you know.
You know his story.
You could probably say it better than i could, but he was the reigning chess champion for what?
Like 11 straight years global champion, and He was like one year.
He's like I'm not doing this again, not coming back.
I'm not competing.
And when they asked why he was like, I have done it.
I don't have anything left to gain.
So you have someone like Magnus Carlsen who just absolutely demolishes to the point where he's uninterested.
And then you have someone like Lindsey Vonn, with the Winter Olympics this year, who had no reason to come back.
She's been super successful but was just curious about her own abilities.
And so... it's like, well, what's the difference between a Magnus and a Lindsey Vonn?
Someone who leaves when they're at the top versus someone who keeps coming back and trying.
And I think that when we are like an underdog, when no one's expecting anything of us, it's easy to make the scrappy decisions and be annoying because no one's watching.
And underdogs ask, well, how do I make it?
Like, how do I make it there?
But then, when you start to become a champion like Magnus or Lindsay, it becomes not how do I make it, but how do I maintain it.
And so you go from playing to win like an underdog to playing not to lose like a champion, which is like two different kinds of motivation that we're pulling from.
And so it's not like how can our ambition get us to success, is can our ambition survive success?
Because surviving success and still being interested is a whole other game.
When I was in high school, I won the state title for discus.
I was like, no, that's cool.
We are learning a lot about each other, even though we've known each other for years.
I still hold the school record to this day.
And that was my junior year.
And I did exactly what you said.
I made an excuse and I didn't come back my senior year because I was like I don't want to.
I don't know how to play not to lose.
It was easy for me to play to win because no one expected anything of me.
Now that I have expectations which now I'm laughing because I'm like the expectations of the high school track and field women's throwing like everyone's watching.
I was too scared of what would happen if I lost.
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Well, I feel like when you're on top that's scarier, because at least when you're like the scrappy underdog you could lose and everybody's like oh, good job trying.
Or, more likely, nobody says anything because nobody saw you lose.
But for me, saw the 20 discus i threw and hit a car.
Yeah exactly, and think about this for me like i was thinking for a long time.
You get to the higher levels and then i just look down.
I'm like man, this fall is going to hurt.
Yeah, you know, if you're not on the, if you're not on a high level, then you take risks, and Yes, it can be risky in terms of But have you fallen though?
And does it hurt as bad as you thought it was?
Never does.
Never does.
And that's the thing.
I have to keep on reminding myself like hey listen okay, that thing that you're afraid of happening worse have happened.
And you survived all of those.
And so you'll if that happens, you'll survive that, too.
And it's but this is the thing.
It's like a constant.
It's like a constant thing, because I think that's one of the things that we have to.
That I'm learning now is that we have to relearn and reinforce this almost daily.
You know, just because the fear will come back.
Those voices in your head can be loud.
And I think especially for high achievers, the the big question is, am I enough?
Have I accomplished enough?
What is enough for you?
What does that look like?
Have you have you struggled with that feeling, that concept?
I, we all want, what did someone call it one time?
Cognitive clarity, which means like and this is you know, you and I have talked a lot about politics.
It's a lot of the like science behind politics of like, I'm liberal or I'm conservative.
We don't want to live in nuance.
We want to be able to say I'm this or that.
And I think, like we want to be able to say that with our job is like I have made it or I'm still on the way.
When I think the more comfortable I can get in recognizing that there is no finish line.
There is like no confetti cannon that I'm going to get.
There is no like email that's going to change everything for me.
You know how sometimes you look in your spam folder to be like is there a life changing opportunity in here that I just didn't get?
And once I could just get out of this like singular outcome mindset and get really excitedly curious about what I'm solving and make it fun and I get that.
That's a privilege to make it fun.
Then it becomes just the outcomes are better for it.
You know, right now we just like got off of a like two hour planning for all this stuff at And it's all about just being really curious about, like where you know how events are making speaking decisions, what they're getting paid, what the women in our community are doing to apply.
And it was just like all really interesting, excitedly curious, asking good questions um having goals but not attaching to them.
So i think for me, like one of the questions i ask on my podcast uh, when I interview people, is like, what does making it look like for you now?
And how is that different than how you would answer that like five or 10 years ago?
I'll answer it.
And I want you to answer it for me.
Um.
For me, making it now is more around um, Not how far I can reach, but how far I'm helping other women reach.
So it used to be really set on like how many stages am I on?
How many books am I writing?
How many TED Talks?
How much money am I making?
And now I'm like, I want to create a system that teaches other women how to do that.
And so my success is more fun and more scalable when it's not around my own bandwidth.
Five years ago, it was a just show.
It was like, how much can I do?
How much can I get?
And that was the right time for it to be that way.
Because I had to get that in order for people to be able to listen to me, to trust me to do this.
But that was a shift that I made in my definition of making it, and also just becoming a parent shifted that too.
It'll always shift when parenting comes into the role.
That's going to be big.
And I think for me, I've worked hard in the last few months to accept that I have made it.
And I've gotten to that feeling of enough.
And I think for me, the next horizon would be...
Time.
Mastery of time.
That's the thing.
Because I'm content with the impact, because I know the compound interest of just the content machine that we've created, with daily podcast episodes, posting and everything.
I'm really happy with the impact that I've had.
And now I want to focus on having more of an impact on my kids, my sons, Kai and Dominic, and spending time with Whitney and focusing on that legacy.
And right now, with the way that things are going, I'm on the road a lot, a lot more than I'd like.
And when I am home, I've got a ton of podcasts to do, batching to keep up.
So the next step of making it will be the feeling of not feeling alone, hurried all the time, the ability to comfortably say no to opportunities.
That's the next, that's the next level.
Um, but I'm.
I'm content, and it took me a long time, a lot of journaling, to get to it, because I started to say okay well, if you haven't made it in that yet, what does that mean?
What does it even mean?
You know, because if you ask the younger version of yourself they, he would say for sure, you've made it.
And even if you present all these problems, you're like that.
You're not going to you're not going to lose your house.
You know, everything's fine.
You know, so I think it's just acceptance of of I'm in a good spot.
I trust my strategy is going to keep on moving forward.
But time mastery and the ability to to invest more time comfortably with family is going to be big.
There was this fitness influencer that I follow.
And I'm probably saying this to the wrong person, because you're super jacked and you go to the gym a lot.
But he was like the people who are 0 body fat, these crazy jacked bodies um, who are like just do 20 squats in this routine.
You don't see the sacrifices that they're making in their lifestyle to stay at that body type.
And so and he was like most of the time, like you don't want to live a life that requires those kinds of sacrifices.
Right.
And I was like yeah, I don't need that like rock solid bod, because like I, like you know the chips and salsa at a Mexican restaurant with a margarita salt rim.
Same thing with my business where I'm like, I see, I mean, you've been on Mel Robbins podcast.
You've seen like, Holy shit, this is like they have just made it.
If we knew what it took to do that, it might not be the decision that we make to do it.
Yes.
So I really like where I'm at right now in my business.
I'm not Mel Robbins.
I'm not Brene Brown.
But I like that I am able to support my family in doing this and the lifestyle that it affords me.
And for me, that's enough right now.
Yes.
Well, I'll add something right here too.
I was doing an event with John Maxwell.
And he would say...
A lot of people ask.
How do I do what you do?
And he responds.
If you want to do what I do.
Are you willing to do what I did?
And it is like.
Oh shit.
And when I look at what I have done to get to where i am today whether that was starting headbands of hope or all like the free speaking i had to do to get the reps in, i'm not sure if i would do it again like if someone presented it.
You know, starting over, i love where i'm at now but damn, that was a lot harder than i thought it was going to be.
It always says yeah, It's so true.
It's so true.
And I've got a funny story for you.
Because I remember one time Kai was watching TV and he saw The Rock.
And we all know what The Rock looks like.
It looks like a science experiment.
Of course.
And he's like, Daddy, I want you to get a six pack.
And it was like five, six at the time.
So I.
Walked up to him.
I kneeled down and looked him in the eye, put my hand on my shoulder and I said Kai, I want to be really clear about something.
Your daddy will never have a six-pack.
And he said, why not?
I said, because I am simply not willing to do what it takes to get that.
Yes.
And the reality is, no, I don't need it.
I'm married.
I'm good.
I'm done.
And I think I am enough in that regard.
And then also, I recognize the path.
It's not just an undesirable lifestyle for me.
It's an undesirable lifestyle for the people around you.
A hundred percent.
Anytime my husband's like, I'm doing low carb this week or no carb, I'm like, damn it.
Because it's just...
I'm like, well, then what are we going to fight about?
Because this is how it's going to go.
That's it, right?
And I think it's so important to come to that conclusion sometimes.
It's like, okay, there is some goal.
That looks good.
What will it take?
No, no, not for that.
And then just coming to terms with that.
And I think a big part of that is avoiding what the philosopher Rene Girard would call mimetic desire.
So humans will look at other people, monkey see, monkey do.
It's through mimicry.
Oh, I see a person doing that or having these things.
So I want to do that mainly because I see that.
And then we play the status game with people who don't even know exist.
And then we feel bad because we're grading ourselves on their terms, not ours.
And we don't know what they've had to go through.
We all know with social media it's just a snippet.
We're seeing a fraction of a fraction of 1 of their life and it is heavily curated and everything like that.
And the thing is you just I feel like it's so important to have your blinders on, So you start to just continue to focus on the things that are most important to you, so you can really harness that authenticity and not get distracted by so many other things.
Because it's really hard to go through that introspection to understand what you really want and why, and create that purpose and own it.
But it becomes harder when we're distracted by all of the things we can see in the media that can lead us astray.
So there's a thing that I call the purpose test in making it without losing it.
And it kind of applies to what we're doing right now.
And anyone...
You can do it right now.
So I tell people, whatever the thing is that you're chasing whether it's a you know money goal, whether it's something an award related to your job, maybe it's a six pack that we're talking about get like one thing in your head.
You can pause the show while you do that.
Okay, you got it.
So what I want you to do now is imagine that you got it, whatever that thing is.
You got the email, you got the notification, you got the phone call.
But the kicker is no one knows that it's.
You can't tell anyone, you can't share it, you can't tell your spouse, you can't tell your parents, you can't tell your colleagues, you can't post on linkedin.
I'm pleased to announce that you have to remain anonymous.
Is the thing that you're chasing?
Would you still do it if no one knew about it?
What is your answer?
Kwame, that's so funny.
I feel.
I feel like the uh, now i want to know what you're chasing.
That was funny, it's.
Yeah, i mean, i realized that that's really funny.
So things like I like having the impact.
Podcasting, all that stuff is great.
I like knowing that I can help to change people's lives.
I do that.
I do that for free, like mentorship, all that stuff.
I love it.
That's why I'm not on my sales calls anymore.
FYI.
Because I'm like, I don't care about the price.
Let's go.
Let's do it.
Yeah.
I can negotiate well with anything else.
But if it's like, hey, you're negotiating fun for me.
Okay.
Yes, please.
But then I think about the awards.
And I think, being an entrepreneur being uh, raised in law school, you know there's a lot of status and it's a lot of the awards.
Like i have a i used to have like a schedule of achievement, but i do recognize that i have like this metric for myself where I need to have a certain type of accomplishment within a certain timeframe, where I don't feel good.
And then it's like, I don't even care about these things.
Yeah.
Just want to be able to know that.
Yeah.
Yeah.
Wow.
Like I just got the, uh, what's it even called?
The Inc 500.
Nice.
Founder.
Yeah.
Um, Exactly my reaction.
Cool.
Five minutes later, I was like, Well, that didn't solve all my problems.
To the next thing.
And not to say that, like those things shouldn't be like celebrated applauded, and not to say that you shouldn't want those things.
But if they are like your primary driving force, then it's probably knowledge to receive that you're you're going after things based on how they look instead of how they feel if you still would go after it with no one knowing then it's a really good indicator that like Your like compass is well calibrated.
Go for it.
And sometimes it doesn't mean that we shouldn't go after it, but it might mean that we should change the way we think about it.
Yes.
So I'll give a more tangible example, too, because last weekend we did a spring break.
And we went to Hawking Hills, which is a beautiful part of Ohio where it's really cool.
So like a glacier a long time ago melted there.
And so there's very interesting unique topography caves and like many mountains and things like that.
And it's a great place for astro tourism.
You can see the stars perfectly because there's no light pollution.
So we rented a cabin out there, had this nice property with a pond and everything.
No screens ever, just completely disconnected.
And we had so much fun.
And I said to myself why is it that I always want to do these international trips, like these international luxury trips with the family?
And I feel so pressed to do that.
And I had to be honest with myself because the depth of happiness and connection we had here was so much deeper.
And I was like, man, I have to be honest with myself.
It is two reasons.
The pictures look better.
And also I see other successful entrepreneurs doing these like very epic, expensive trips.
That's why I want to do it.
But if the goal is happiness and connection, I got this right here.
Right here.
You know, and so I intentionally didn't post anything about it.
I was like I want this to be its own thing, encapsulated thing, just for me and my family.
You know something real.
And so just recognizing oh wait, a second those allow.
A substantial amount of my goals are ego driven, like they used to be.
They used to be for a specific purpose when you're young, especially as a young thought leader in negotiation.
I started all of this at age 27, you know there's no, there wasn't a such thing as a young negotiation expert.
So i needed a lot of that uh, that external validation to show people that i was legit and i actually knew what i was talking about.
But at this point I had to recognize a lot of it is just vanity and ego.
When does it stop?
Yeah, yeah.
It's so interesting.
And I love that you shared that.
I've had many moments where I'm like, yeah, well, I didn't document it.
I didn't take a picture.
How will people know that we did this thing?
It's like, well, what if they don't have to?
Interesting you say that about the young thing, too.
I started young as well.
And I think that I was really looking for proof to show people that I was qualified to be here.
And and then that just didn't doesn't stop, you know.
And as I think about like the book comes out today and as I think about it, you know, of course, with books there's a lot of pressure for lists and you know whatever.
New York Times, USA Today.
I think about my daughter when the books came to the house and you know you open it up for the first time and she's like mama, you wrote a book.
She wasn't like, Is it a New York Times bestseller?
It was just like, whoa, you wrote a book.
She did come at me, though, because she opened it.
She's like, where are the pictures?
What's the problem?
Don't give me this trash uh, but it i do.
You know you, you have to kind of see it sometimes through the eyes of like young you or your kids.
It's like yeah, you're in the game, like you're doing it.
I remember talking to when i was writing my first book.
I got like really bad edits back from an editor.
It was like, oh my gosh, this is like terrible, i'm gonna have to start over.
And i was talking to my business coach about it and she's like well, what are you making this mean?
Like it means i'm a shitty writer, that i'm not like shouldn't be doing this.
And she goes a new york times bestseller and what do you think the problems they're having are?
And I was like, probably, you know, book sales and getting edits back on their book.
She was like, yeah, this problem isn't reflection that you shouldn't be here.
This problem is a reflection that you are participating in the game.
So I think a lot of times like we think of our problems in business and work, or whatever it might be, as reflections of our abilities, when really it's just evidence of the process.
It's like yeah, someone who is not doing anything, not going to have, like you know, a lot of repercussions, of risks that they didn't take.
But when you have big problems, it's probably means that you're doing big things.
And so kind of giving yourself some kudos for that.
Oh, that's good.
That is good.
And this is the perfect time to bring in Simone, because I could talk to you all day about this, Jess.
I know that because we have.
We have.
We do a lot.
So, Simone, what's on your mind?
Back in the day, you were not using your Netflix account and you were friends with Mark Raddolf.
You had the money to have your own subscription, right?
So why did you decide to use your sister's Netflix account?
You know, once a younger, annoying sister, always a younger, annoying sister.
I think...
Even when I was a kid and I was like really into eBay, I sold all my American Girl doll stuff.
And then I went and sold my sister's American Girl doll stuff because I saw how much you could make from it.
And so I no longer use her Netflix account, but I would ride that train as long as it took me.
Well, and Simone, here's the thing.
Tell me if I'm wrong, Jess.
But probably the reason you don't use it anymore is because they cut down on the ability to do that.
A thousand percent.
I don't understand why all of these streaming services are now not letting us use other people's passwords.
Come on.
Now it's just more expensive than cable.
I was talking to Whitney about that the other day.
I was like, you know, we were just led like sheep to the slaughter.
Oh my gosh, it is so cheap.
I'm going to quit everything.
Forget cable.
This is the future.
Yeah.
The future of value extraction.
Yeah.
And I did get an email the other day from Netflix about a price increase.
I was like, Always, always, always coming for more.
But Netflix and Hulu, if you need a keynote speaker for your next event.
Yeah.
Or if you want to advertise on Negotiate Anything.
That's right.
That's right.
We need sponsors.
We love you.
Yeah.
Hire us.
Yes.
Oh, this is good.
Well, Jess, delightful as always.
I appreciate you coming on the show.
Before you go, I want to make sure the listeners know where they can get in touch.
What's the best way to connect?
Tell them about the programs.
Of course, let's land the plane with making it without losing it too.
Y'all I'm not hard to find.
I am on Instagram at Jess Eckstrom.
I will say I'm cooler on LinkedIn than I am Instagram.
So find me there.
I also send out a hype text every Monday, something that I'm like thinking about, a quote, a question.
Send it every Monday, 11 a.m.
Eastern.
So you can text me the word hype to 704-228-9495 and you can get that.
And then you can buy Making It Without Losing It out today.
Anywhere books are sold.
I'm a sucker for local.
So if you can find your local bookstore and ask if they have it or ask if they can order it, that would be great.
Amazing.
Jess, thank you so much for joining us again.
Really appreciate it.
Thanks Kwame.
Thanks Simone.
