Creating Confidence with Heather Monahan
How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom
21 Apr 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What does it mean to stop chasing a problem-free life?
Don't try to achieve things to have zero problems. Do things that have problems you're excited to solve. And once I realized that like, oh, there are not these like thresholds that launch you into like a zero inbox, no problems. It's all about like, do you like the problems you're solving? Do you like the people that you're with? Do you like the lifestyle that it affords?
And it just changed from these like singular finish line outcomes to a more evolving process that just makes it more fun and also more scalable.
Come on this journey with me. Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. I'm ready for my close-up.
Chapter 2: How can you evaluate if your goals align with your values?
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 and women bestselling author, Forbes top rated speaker.
and she's a mom her first brush with success was selling all of her toys on ebay when she was 12. since then jess and her companies have been featured on the today show good morning america and more more importantly her companies have helped millions of women and girls around the world this is true she's the 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 our kids you're hilarious and searching for the best
Breakfast Burrito in America. Jess, thank you so much for being here.
Oh my God, thanks for having me. Before we get started, I have to share something with your listeners about you.
Chapter 3: What is a success fingerprint and how do you define yours?
Can 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.
Chapter 4: How do you shift from singular goals to a mission-driven approach?
You're like, just so... you walk the walk and I just really appreciate it. And yeah, I just really appreciate you.
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.
Chapter 5: Why is tying happiness to a finish line detrimental?
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. And I understand that. But this person sent me a note and just said, hey, need this intro and dropped a name into a chat to me, which is like, stop.
It was interesting because, and this is super valuable, I hope for everyone, because we all need to remind ourselves of this. If you want someone to do something for you, especially a big ask, right? Because if someone has a coveted name or someone... Nobody wants me giving it, nor are you giving out all their information and saying, oh, yeah, let me go ahead and connect you.
Chapter 6: How can you zoom out to align daily actions with long-term goals?
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. 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 and we know that before we even click on the text or the email, they are asking you for something, a favor, a this. I need this. Can I pick your brain? And I think it's just like such a good reminder that it's like, okay,
Chapter 7: What strategies can you implement to enjoy the journey?
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? And so I think that there's a healthy amount of transactional nature of relationships. But sometimes I can maybe be a little bit too...
much like uh 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 um damon west do you know damon I do.
Chapter 8: How can meaningful work impact your overall happiness?
Great guy. And him and I have been really great with helping each other, like make introductions to speaking or whatever it might be. And he was just on Jefferson's Fisher. Jefferson Fisher's The Next Conversation podcast, which I really love. And as a public speaking expert, like I really want to get on that show. And so I wasn't just like, hey, can you introduce me to Jefferson?
I was like, here is basically a like I'm submitting a what's it called when you get your Ph.D., a dissertation as to why Jefferson's show is like. perfect fit for me like I'm not just copy paste spam and so if someone does that where it's like man you really put in the time to did the homework then again that is like something I can consider but yeah I get that a lot and I know that you do too.
Yeah. And for everyone listening, you know, it's not just in the speaking business. It's not just in the podcasting world. It's in life, right? Like you're going to want a favor from somebody once in a while, you know, people oftentimes get nervous to ask. And here's the thing. And I know we both feel like this. If someone asks us for a favor, that's
easy for us to do and we like people they're nice people it makes me happy to do it right don't let asking hold you back just know to ask in the proper way like by putting yourself in the other person's shoes being thoughtful about what you can do to help them you know hey i realize this is a big ass hey i know that your social capital is massive and this is going to take a hit for you what i do for you because i don't want this relationship even just saying something as simplistic as that
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. Cause I know that I feel, start feeling like I'm asking people for favors, whether that's an endorsement podcast, like what we're doing now or buy the book or something. And I know I have to
get out of my head and I tell my speakers this at Mic Drop all the time, you're not asking for a favor if you believe what you're doing is valuable. But I also like when it came to asking for endorsements or things like that, I did took some time to figure out what they were working on. oh, you have a book coming out this time. You have a foundation that you're raising money for.
And so instead of just saying, can you do this? It's like, here are some ways that I would love to return the favor, contribute to you based on like what they're doing. And I felt like that went such a long way. Even if they didn't take me up on it, they just saw that I did the homework, which I think is an age that where everything is so quick and
Just taking a little bit of time to do show that you did your research or do the homework is goes a long way.
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.
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