Episode 61: The Joy of Curiosity: How Questioning Assumptions Changes What You See
Jul 22, 2026What if the biggest thing holding you back isn't a lack of resources—but a belief you've never stopped to question?
In this solo episode, I'm sharing one of the biggest insights that came out of a recent retreat with the incredible women in The Connect, my coaching community. A simple phrase kept surfacing: "We don't do that." Inspired by corporate anthropologist Dr. Andi Simon, I explore how those four words can quietly limit our leadership, our businesses, our relationships, and our ability to see new possibilities.
I also share one of the most personal examples from my own life—how choosing curiosity instead of following the expected script completely changed the way I approached my divorce. That decision led to a healthier co-parenting relationship and, years later, my sons thanked me for making a different choice than many people expected.
Whether you're leading a business, growing a team, or navigating change in your personal life, I want to challenge you to stop assuming you already know the answer. The most powerful breakthroughs often begin with a simple question.
This episode is my invitation to trade certainty for curiosity—because I've found that joy often begins where our assumptions end.
๐ Key Takeaways:
Curiosity Opens Doors That Assumptions Keep Closed
One of the most dangerous phrases in leadership and life is, "We don't do that." Dr. Andi Simon encourages leaders to notice these automatic responses and replace them with curiosity that uncovers new possibilities.
Audience follow-up → Where have you automatically dismissed an idea because "that's not how it's done"?
Community Interrupts "Stinkin' Thinkin'"
Lori reflects on hosting women from The Connect at a Hudson Valley retreat and shares why meaningful connection matters. Isolation often reinforces limiting beliefs, while community provides perspective, encouragement, and new ideas.
Audience follow-up → Who are the people helping you challenge your thinking instead of simply agreeing with it?
Your Story Isn't Fixed
Lori vulnerably shares her divorce journey and how she intentionally chose collaboration over conflict. Rather than following the expected script, she became curious about what would create the healthiest future for everyone involved—including her children.
Years later, her sons thanked her for making that choice.
Audience follow-up → What story have you accepted as "the only way" that may deserve a second look?
Your Customers Will Tell You What They Need—If You Listen
Businesses often believe they understand how customers use their products or services. Lori explains that curiosity—not certainty—is what leads to innovation and stronger customer relationships.
The best insights don't come from assumptions—they come from asking better questions.
Audience follow-up → When was the last time you asked your customers what they actually value instead of assuming you already knew?
Joy Is a Leadership Strategy
Choosing joy doesn't mean avoiding difficult conversations—it means approaching challenges with openness, curiosity, and a willingness to learn. Leaders who remain curious create stronger relationships, healthier teams, and better decisions.
Audience follow-up → What would change if you approached your next challenge with curiosity instead of certainty?
๐ Mentioned in the Episode:
- Dr. Andi Simon – Corporate anthropologist and keynote speaker who challenges organizations to rethink assumptions and embrace curiosity.
- The Connect – Lori's coaching community for ambitious women committed to leading with greater purpose, joy, and connection.
- Hudson Valley Retreat – A community retreat focused on meaningful connection, personal growth, and leadership development.
- "We Don't Do That" Mindset – The limiting belief that often prevents innovation, creativity, and personal transformation.
- Customer Curiosity – Using feedback, observation, and questions to better understand how people truly experience your products or services.
โจ Reflection Prompts:
- Where in your life are you saying, "We don't do that" without questioning why?
- What assumptions have you made about your customers, your team, or yourself?
- Who helps you challenge your thinking instead of reinforcing it?
- What would become possible if curiosity replaced certainty this week?
- How can choosing joy help you become a more effective leader?
๐ง Who This Episode Is For:
- Leaders looking to create more innovative, adaptable teams
- Business owners who want to better understand their customers
- High-achieving women ready to question limiting beliefs
- Professionals navigating change or major life transitions
- Anyone who wants to replace fear, assumptions, and certainty with curiosity, growth, and joy
๐ฉ Want to Go Deeper?
Follow Lori on LinkedIn to continue the conversation
- Book a Leadership Strategy Call with Lori: loripine.com
Learn more about Andi Simon on https://www.linkedin.com/in/andisimon/ or her website: https://www.andisimon.com/
๐ง Subscribe to The Joy CEO Podcast
โญ๏ธ Leave a review to help other heart-centered leaders find the show
๐ฒ Share this episode with someone who’s navigating pressure and wants to do it with more grace
Transcript
Hello, and welcome to the Joy CEO Podcast. I'm your host, Lori Pine, and I am so pleased to have you here with me today. This is a podcast about leadership, about growing your career, and using joy as a leadership strategy. Not a bunch of fluff. We are going to jump in today. I have some exciting things to share with you.
If you are new here today, welcome. So glad you are joining, and if you have been with me for a while, thank you for coming back. You know that I adore you and so appreciate the fact that you listen in. My mission is just to impact one person at a time, and if that is you today, really, it is my honor. So it's been a little bit busy over here in my world.
I hosted a retreat last week where 10 women who are part of my small group coaching community called The Connect [00:01:00] flew in from all over the country and spent two and a half days with me here in the beautiful Hudson Valley of New York. And it was one of those experiences where I felt like it just really brought out the best in me.
I was able to host them, entertain them, shower them with gifts, and, you know, gifts is kind of my love language. Generosity is one of my core values. And really get to do what is my superpower, which is bringing amazing, brilliant, vibrant, superstar women together for the sole purpose of connecting them.
And when the tide rises, all the ships rise. Every single woman is better as a [00:02:00] result of having invested that time and energy with one another. I will literally die on the sword for this belief. We are all better when we are together. It is in the isolation, it is in the stinkin' thinkin' where we get into trouble because we start to think that it's only us, and that we are chronically and perpetually unique, when in fact, so much of what is happening to you and to me is happening to s- so many other women.
And the more we open up and the more we share about it, the more connected we become, the more empathy we have for one another, the deeper that empathy can grow for ourselves, and the more we can remove the rocks and [00:03:00] actually get after our biggest, boldest, brightest dreams. And that, my friends, is joyful living At the retreat, I brought back Dr.
Andi Simon. She was on the podcast in episode 26, so if you haven't listened to that, go back because sh- she is just this walking encyclopedia of wisdom. Everything she says, you just wanna hang on to. It's like she's a prophet, and you just wanna listen to her. So Andi has really become a, just a dear friend and a mentor to me.
I feel so privileged to have her in my very tight circle of board of directors. So it was very obvious to me when I was putting this retreat together and [00:04:00] planning the agenda, that I would include Andi and ask her if she would be willing to be the keynote speaker on Friday morning, and of course she was.
What unfolded was this really powerful conversation about curiosity. If you didn't listen to episode 26, let me just give you a little overview of Andi. She's a trained anthropologist, a PhD in anthropology, and she was able to apply those principles to business. She, for the past 20 years, has run a consulting company and has coined herself a corporate anthropologist.
She goes into businesses, and she basically uncovers what is happening Asks a lot of questions, gets really curious, considers herself an explorer, [00:05:00] and uncovers and discovers what is happening inside of businesses. And it has made her incredibly effective because she's willing to operate in the gray.
She's willing to be in the change where humans, by nature, are incredibly uncomfortable. So Andi was able to come be with our group in this cozy little setting that I set up, and she was able to really talk to us about the power of curiosity and how often are you or somebody on your team saying, "We don't do that.
That isn't something our company offers. That isn't in our business model," or [00:06:00] on a personal note, "We don't do that in our marriage. We don't do that in our family." And what if you were able to get curious about that? Would that open up an opportunity for you? And Andi posed that question to my 10 retreat guests, and we really were able to open up about what would it look like, what could change, what would have to be true in order for our thinking to even allow an opportunity for the space to begin to process could something else be true.
And Andi gave several examples of clients she's worked with, clients who thought that their product was used for one thing, but when she [00:07:00] started interviewing actual distributors, actual consumers, she found out the product was being used for something entirely different. And then that gave her an opportunity to work with the founder of the business to say, "Do you see what's happening here?
You think it's X when in fact the end user is using it for Y. What could happen if your product was actually marketed for Y?" And light bulbs go off You know, something similar happened to me in my personal life about 20 years ago. When I was getting divorced, I had two little boys, and anybody I knew at that time who was getting divorced seemed to do it in a very cookie cutter way.
[00:08:00] It was every other weekend, share the kids Make sure the custody is split, and have a quiet ongoing war. Don't really be nice to each other, don't like each other, say some under your breath horrible things about the other person, and put the kids in the middle. And I was observing this, and I didn't want to be part of that.
The unspoken rule seemed to be we don't do it any other way. These are the rules for getting divorced. This is the protocol for how you act, and consequently, this is how your children will be impacted. And for me, that didn't seem like an option, so I didn't do that. Instead, I did the opposite. I made sure that even though I had every [00:09:00] reason to be angry or self-righteous or indignant, I wasn't.
I kept coming back to the fact that my boys were half him and half me, and I continuously told them, "We only gave you the best parts of us. We kept all the bad for ourselves." And I reinforced time and time and time again that everything good about their dad went into them, and everything good about their mom also went into them.
And so therefore, they were pure and good and full of love. And even though we didn't work out, we could still be friends. We could still be a little family, and it could be okay. And so I included my ex in everything, in birthdays, [00:10:00] in holidays, in family parties, in the schedules, in all of their sporting events, in school events when my son was in a play.
I didn't gatekeep anything, and as a result, he was a part of, and they have a childhood that includes both of us, not just one of us, not just the other. They have Christmas memories where my ex-husband slept in the guest room and was here when they opened their tree. And why would I do that? Not for me.
That didn't make my life easier. For them And because I was able to get curious about what could be, what was the possibility, what was the possibility for me and the mother I wanted to be, [00:11:00] the divorced mother, the single mother, what was I able to live with? And I wasn't able to live with a version of myself who was nasty and ugly and constantly fighting.
In fact, when I was in the judge's quarters finalizing my divorce, I had to fly back to Little Rock, Arkansas, and I had waived any rights to child support or a- any financial support. The judge really questioned me, and I just said to him, "I don't want to spend the next 18 years fighting with somebody over money or something I'm not sure he can ever uphold.
I don't wanna see him thrown in jail over it. And so I want to trust that there is enough in this universe, that there's enough in [00:12:00] this world that I will be taken care of and so will he, but most importantly, that my boys will be." And you know, I look back and that was the right decision for me because we were all taken care of and it worked out for everybody.
So my boys are now 22 and 24, and they've thanked me separately on different occasions, really unprompted for being good to their dad and that really says something. So when you get curious, what happens for you? If you are facing something, whether it's personal or professional, and there isn't a framework, there isn't something to tell you how to do it differently, [00:13:00] could you trust your intuition?
Could you trust that somewhere inside of you there are guiding principles, guiding lights like a runway on a airport that will lead you to where you're meant to be led It's the same no matter what we're doing. This applies to your business, too. Where are the nuggets that you currently can't see? I was on a panel with one of the marketing experts from Duolingo, and she said all of the nuggets are in the consumer comments.
She said, "That's where we go for all of our innovation. That's where we go for our next marketing plans. That's... Those, those comments from consumers in our social feeds dictate where we [00:14:00] go next." So mining that consumer information is so powerful. Are you doing that for your business in the position that you're in?
Whether you're calling on customers, for that customer, do you know what is being said about your product for your customer If you're an, a business owner, do you really know how your customers are using your product? And is there this white space of opportunity that you're not even paying attention to?
So instead of, you know, insisting that this is how it's done or we don't do that, what if? What if? And what would that possibility, it look like? So in closing, ask yourself where the we don't do that is living in your life. [00:15:00] Is it showing up at work? Is it showing up with your customers? Is it showing up in how you lead?
Is it showing up in your personal life? And when you say, "We don't do that," is it a principle thing? Is it a fear-based thing? Is it a scarcity thing? And other than something that's, like, really dangerous or goes against your values, what if you did do something? What if you took the vacation? What if you played hooky on a Friday afternoon in the summer and everybody went to the beach?
What if you could lighten up a little and not take yourself and your work and what's going on in the world quite so seriously? Could you find room for a little bit more joy? Because that's the real [00:16:00] key. Joy lives within you, and you can choose it in any moment. It can coexist with other emotions, but it lives within.
And when you're choosing joy, you're operating at a higher vibration. And so it's really hard to be joyful and angry. So my friends, get curious. Look around. See what it is there is to see. Start asking questions. Ask your customers, ask your employees, ask people, "What is happening? How do you use this? How do you use us?
Where's this product? What, what, what could it be?" And uncover u- untapped potential and just watch what could happen if you get curious. I'm Lori Pine, the Joy CEO, and I'm so glad to be doing it with you. Have an amazing week [00:17:00] Please be sure to sign up for my newsletter where I give you so many tricks, tips, hacks on how to find more joy in your leadership, and be sure to share this episode with a friend.
Glad to be doing it with you. See you next week. Thanks for listening to The Joy CEO. I hope today's conversation left you feeling seen, stretched, and a little more grounded in your own joy. If something resonated, be sure to hit Subscribe, leave a five-star review, and share this episode with someone walking a similar path.
And if you're ready to take this work deeper, connect with me on LinkedIn or Instagram, @loripyne, or head over to my website, loripyne.com, to learn more about coaching, retreats, and how we can work together. Because joy isn't just personal, it's powerful, and when you lead with joy, you don't just rise, you bring others with you.
Until next time, keep leading with heart, and don't forget to claim your [00:18:00] joy