318. Life: The Real Reason You’re Questioning Everything Right Now, with Laura Gassner Otting

You’ve checked the boxes. You’ve followed the rules. And still, something feels… off. If you’re standing in the middle of success and wondering, “Now what?”, this episode is for you.

Laura Gassner Otting - bestselling author, keynote speaker, and all-around truth-teller - joins Megan to talk about identity shifts, outgrowing your former self, and the surprising power of trusting your intuition.

This conversation is for the high achievers who are secretly exhausted. For the people-pleasers who are learning to say “no.” For the women who are ready to stop playing small.

Because what got you here won’t get you there, and Laura’s here to help you figure out what comes next.

What You’ll Learn in This Episode:
✅ What to do when you’ve built success that no longer fits you
✅ How to know when it’s time to walk away from a job, business, or relationship
✅ Why we cling to old versions of ourselves - and how to gently unravel them
✅ The subtle difference between imposter syndrome and growth
✅ Why comparison is the root of mediocrity
✅ How to use facts, not fear, to make bold decisions
✅ The importance of protecting your energy and curating your inner circle
✅ Laura’s “F you, pay me” mantra—and how to claim your worth without apology
-----

About Laura Gassner Otting (LGO):

• Website: https://lauragassnerotting.com/
• Books (Wonderhell and Limitless): https://lauragassnerotting.com/resources/#books
• Instagram: https://www.instagram.com/heylgo/

---

00:03:24 – From the White House to TEDx: Laura’s beautifully messy origin story
00:07:55 – Identity crisis: What it really looks like and why it’s so common
00:10:00 – Why the people who “know you best” might be holding you back
00:13:53 – Changing the voice in your head from a limitation to an invitation
00:18:28 – When to know you’ve stayed too long—and why success can lead to sabotage
00:22:59 – The myth of being “for everyone” and the gift of letting go
00:24:31 – Confidence through facts, not fluff
00:27:23 – You’re not out of your league—you’re just out of your lexicon
00:30:59 – Comparison vs. becoming a category of one
00:34:46 – How to train your brain to see opportunities (not just obstacles)
00:36:39 – Why too much advice might mean you already know the answer
00:39:11 – “F*ck you, pay me”: The mantra you didn’t know you needed

Today's episode is brought to you by The Planner's Vault—your go-to resource for wedding pros who want to grow, connect, and thrive. If you're looking for expert education, a supportive community, and real-talk guidance to elevate your business, come join us inside The Vault. We’d love to have you!

For Real on Social Media:

Instagram: @forrealwithmeg

Facebook: https://www.facebook.com/ForRealPodcast

Hosted by Megan Gillikin, For Real is presented by The Planner's Vault, and is produced by Walk West.

Creators and Guests

Host

Megan Gillikin

Wedding Industry Coach + Founder of The Planner's Vault

Producer

Jason Gillikin

CEO and Executive Producer at Earfluence

What is For Real: Life, Leadership, & Unlearning?

For Real is a top 1% podcast for high-achievers who look successful on paper but feel like they’re one group text away from burning it all down. Hosted by Megan Gillikin - serial entrepreneur, business coach, keynote speaker, and recovering people pleaser - this show explores burnout, boundaries, identity shifts, and the brave act of unlearning who you thought you had to be.

With unfiltered conversations, “I thought it was just me” moments, and just enough humor to keep it from feeling like group therapy, For Real is your permission slip to evolve.

Formerly Weddings for Real - and glow-ups look good on us.

00:00:00 - Megan Gillikin
Hey friends, and welcome to For Real. I'm your host Megan Gilligan, and whether you're brand new to the show or you've been listening for years leading up to our recent rebrand, I'm so glad you're here. And if you haven't heard yet, the show recently got a glow up, including a new name and an expanded focus. But the heart of what I want to bring to this podcast is still the same and that's honest conversations for high achieving humans who are ready for more. This rebrand has been a long time coming and it's rooted in the conversations and topics that you and I both have been craving more of. We'll be diving into the messy middle the shifts that you want to make in your career, the quiet unraveling of who you thought you had to be, and the bold moves you have to make to step into who you're becoming. In today's episode, it hits all of it right. Life, leadership and unlearning in such a powerful way. I truly loved this episode. You're listening to For Real, the podcast where we get honest about life, leadership and unlearning all the outdated beliefs that are holding you back. I'm your host, Megan Gilliken. I'm a serial entrepreneur, speaker, business coach, recovering people pleaser, and your unfiltered guide through the messy middle of growth. The part that nobody posts about on social media. Inside each episode we dive into the habits, mindset shifts and hard earned lessons that help you build a life and a career you actually want while letting go of everything that no longer serves you. Around here, we ditch perfection. We talk boundaries, burnout, breakthroughs, and we call out the BS that keeps you playing small. So if you're craving deeper conversations, much needed relatability, and full permission to evolve into your next level, you're in the right place. And my guest today is Laura Gassner Otting and she's a best selling author, keynote speaker, executive coach, and former White House staffer. But more than that, she's someone who tells the truth about ambition, identity, and the real cost of outgrowing your former self. And the topics that Laura and I discuss in today's episode are going to challenge you, fire you up, and honestly, they're going to make you laugh. At the same time, we talk about tuning out the noise, trusting your intuition, battling imposter syndrome, and how to stop making yourself smaller just to make other people more comfortable. There are mic drop moments, laugh out loud moments, and so many reminders that you're not alone. If you're in the middle of figuring it all out. This episode is a powerful reminder that you already have the answers if you're brave enough to listen. And before we dive in, if this show resonates with you, I would love it if you would take a moment and follow the show on whatever platform you listen to so you don't miss any of our upcoming episodes. It would also mean the world if you would take a moment and leave a review or send this episode to a friend who you think needs to hear it. It's one of the best ways to help for real, reach more people, bring on great guests, and it means so, so much to me. All right, let's get into it. To start, Laura shares her unconventional path to getting to where she is today.

00:03:24 - Laura Gassner Otting
So I could share the story one of two ways. I could either tell you about all the incredible success that I've had and make it sound like it was all on purpose and on plan, or I could tell you the truth, which is that I basically fumbled my way to where I am now completely by accident, without any strategy, really, mostly just following one particular idea, which is do interesting things with interesting people and interesting opportunities arise. And that started with me doing some interesting things with the world's worst boyfriend, who had exquisite taste in precisely two things, the first being unknown presidential hopefuls from tiny Southern states and obviously the second being girlfriends. And he wanted to stop by this guy's campaign office who was running for president. And I was like, governor. Who? From where? Arkansas? Like, not a chance. George W. Bush had just H.W. bush had just won Desert Storm. He had a 91% approval rating. The Democrats put a sacrificial lamb up, and I was like, not a chance. And then I walked into this campaign office in Gainesville, Florida, and there was a tiny black and white TV in the corner with then Governor Bill Clinton talking about service in exchange for college tuition. And I was like, oh, my God, that needs to happen. What a great idea. So. So I dropped out of law school. I broke up with a boyfriend. I started volunteering on the campaign, and one thing led to another. I ended up doing Political advance, which are the people that go out to towns and cities and gather all the volunteers and put together these giant rallies a few days before the principals arrive. And then he got to the White House. So I got to the White House. And really, my career has been a series of things like that where the next job was then sitting down with somebody, trying to figure out what I was going to do after politics and I was like, your job's in Boston. The guy I'm dating now, who isn't the world's worst boyfriend, is about to move to Boston. Maybe I should come work for you. And he's like, you should come work for me. What do you do? And that's how I became a headhunter. And then I had this moment of rage, five years into it, where I was like, I can do things better and smarter faster than this dude. Why don't I chunk this myself? I, like, walked into his office, and I was like, hey, man, there's a better way. And he's like, hey, lady, there's the door, right? I mean, it was like a Jerry Maguire moment. So I started my own firm, and then I ran that and eventually sold it to the women who helped me build it. I didn't know what I was going to do next. I had the sort of crisis of identity. I started a blog. That blog got noticed. I got offered an opportunity to speak on a TEDx stage. I said, no fucking way. That's terrifying. Who wants to speak? A public? And my kids dared me into it. And I got up on that stage and I spoke. And then that talk got some attention, that I got offered $1,500 to fly to Boise, Idaho, to give a speech. And at the end of the speech, they gave me a check, and I was like, wait. I just talk and you pay me. Tell me more about this job. So I became a speaker. And the next thing I noticed, all the people making real money had books. So I was like, I should get me one of them. So I wrote a book, and then that got some attention. And so here I am now as an author and a keynote speaker and an executive coach, having not had a single strategy other than, like, just keep doing interesting things with interesting people and interesting opportunities arise.

00:06:30 - Megan Gillikin
I mean, it's an incredible story. And as soon as you presented the opportunity of all the accolades or the real version, I was like, yes, please tell the real version. That is exactly why I wanted to have you on the show. I mean, one of the many reasons. And your journey of choosing to lean into doing things with interesting people and finding your way, like, along the path along the way. I think that speaks to so many of our listeners who are these high achievers, Creators, Go getters. Figuring out what comes next. And you mentioned something that I jotted down as you said it, which is a crisis of identity. And I find, yeah, I'd love to kind of start there, because I think, as I think about someone that's listening to this and they're hearing your journey and they're relating to it, or they're like, man, I wish I, you know, I hadn't been so precious about every step that I had taken and had gone with the flow a little bit more. I'd love to talk about the idea of a crisis of identity when to women and what that might look like because I find myself in a place where who I was in my 20s and 30s is not at all who I am now in my 40s. And I've had so many conversations with women as well that maybe started their career doing one thing or had a passion for one thing and then found themselves in what you call that crisis of identity. What happens if you get stuck in that crisis of identity?

00:07:55 - Laura Gassner Otting
Yeah, well, I have so many things to say on this topic, so I, I, I, I will start by saying I' be 54 years old in a couple of weeks. So probably by the time this is out, I'm already 54 years old. And that means I was raised by the first wave feminist in the 70s and the supermodels of the 80s and 90s, right? So a very weird marriage of input there, right? You gotta be like, tough and you have to be skinny and pretty, right? And so there wasn't a lot of wiggle room to explore who, who I was as a person.

00:08:30 - Laura Gassner Otting
I had to fit into these boxes that were like, you had to be tough and you also had to be small, right? How do you, how do you do that and make everybody else happy? So I look at young women who are growing up today. I have two sons, but I look at all of their peers. Both of my sons are in college and they have so many more options. They have so many more megaphones, they have so many more inputs that are giving them body positivity and confidence in their voice. They're also getting a lot of like social media mental health garbage also. So it's not, you know, all raise and happiness, but the, the, the array of options that are available to them is not the same that it was available to us.

00:09:09 - Laura Gassner Otting
And so what that had created for me was this. You can be a insert noun here, right? You can be a doctor, you can be a lawyer, you can be an accountant, you can be a wife, you can be a teacher, you can be a nurse. Like, you can, there were like, it was nouns, but nobody ever said, you can be curious, you can be entrepreneurial, you can be adventurous. Like there wasn't a lot of room for fucking up. There wasn't a lot of room for not having it figured out perfectly.

00:09:38 - Laura Gassner Otting
Either you were the A plus student who everybody believed was going to be able to do big things, or you were a loser. Like, there just. There wasn't a lot of gray area. And the problem is that whenever we try to figure out who we want to become, that who we want to become is filled with gray area and filled with potential loss and failure and ridicule and embarrassment.

00:10:00 - Laura Gassner Otting
And so we go to the people who we think know us best, and those usually tend to be our parents or our siblings or like the friends we've known since high school. And we ask them what they think, and they're like, oh, no, you can't do that. You might fail. And the problem is, is that they don't actually know us. They love us, they don't always see us get hurt, but they don't actually know us like, what we're capable of and what we can do. I didn't run my first mile until I turned 40 years old. And I'm in a month about to go run my eighth marathon. My. My sixth. Of all the. My parents, they. They think I'm insane because they don't remember me as an athlete.

00:10:34 - Laura Gassner Otting
But as women, we have all these on ramps and off ramps of life that we are all like all these multiple layers. And so the problem is when we go back to people who don't know us, but who love us, they want to protect us, and then we don't learn to flex our wings.

00:10:48 - Laura Gassner Otting
Or maybe we talk to the people who are our peers right now. We think they're our peers, but we're really asking for permission from our competitors, right? And we're like, should I do this? And like, oh, I don't know, maybe not sure, right? They're like smiles in the front and knives in the back. Or they say, like, you can't do that. That's too scary. But the way around me is, I can't do that.

00:11:06 - Laura Gassner Otting
I'm too scared. And so what I try to do right now is I try to be just like, absolutely ruthless about the people who I keep around me and the people from whom I take advice. You know, there's. There's just a lot of, how do we get out of that box? I think some of it is just, we should look at who constructed the box for us to start and decide whether or not their voices really matter to us and stop taking votes from people whose voices just don't count.

00:11:32 - Megan Gillikin
Gosh, that's such a great point about the people that you would call in your inner circle, the people that know you and have known you the longest. The reality is, like, they know perhaps former versions of you and are not aligned with who you are now and where you're trying to go. So by just listening to those people, it would be so easy to hold yourself back 100%.

00:11:57 - Laura Gassner Otting
I mean, before we started recording, you were telling me about how you're changing the name of this podcast and you're expanding your audience because you started off in one area and you realized, wait, there's actually a bigger audience. Wait, I'm actually, I have bigger ideas. Like, there's more that's out there. And what if you just stayed in that one place forever? Right. I was talking to one of my kids the other day, and he was saying how he, you know, he's really stressed about trying things that are new because he's afraid he's going to fail. And I said, God, if I stopped growing when I was 20 years old like you, what a boring next 70 years that would be. Right? Like, how exciting. And, you know, I spent a lot of time talking to high achievers, trying to figure out how they're able to do what they're able to do. And every single one of them, I mean, whether they're starting their second billion dollar company or they're at the top of a gold medal run, literally with the gold medal in their pocket, about to go on the next gold medal run or filled with this imposter syndrome, like, this is the time they figure it out. This is time that they realize I'm a fraud. This is the time that I fail. And every one of them changes the voice inside their head from a limitation into an invitation by doing really, what is the simplest hack ever? This mindset shift that's almost. It's embarrassing to tell you it's so simple, but they literally change the words from I haven't done this before to I haven't done this before. And they go from seeing it as this box, this trap, these chains filled with uncertainty and doubt and failure and embarrassment. I haven't done this before. Oh, no. To what an adventure. I get to learn, I get to discover, I get to explore, I get to be curious. Right that, that just simple shift right there changes this limitation into an invitation for everything that it could possibly become. And I, for one, hope that we all live in the space of invitation all the time, because it's so much more fun than the space of limitation that I feel like anchors us all down.

00:13:53 - Megan Gillikin
Yeah, Laura, I will tell you, I think I've spent two years talking about changing the name of the podcast, but sitting in the fear of getting it right. And I hear that a lot from other conversations with high achievers as well. It's like, I built this and this is successful. So to step into what's next, Like, I don't know. And the fear of not getting it right really ties back to what you said about the way we were raised.

00:14:17 - Laura Gassner Otting
Right.

00:14:17 - Megan Gillikin
Like, you were either you were either nailing it or you were failing, and there was no real in between. It makes me think. I don't know if you're a Brene Brown fan, but it makes me think about the concept she talks about of the midlife unraveling, where we are carrying these beliefs and these habits and this view of ourselves until we reach a point where we're like, oh, this is not serving me anymore. And to unravel it, it's like what you might call a midlife crisis. But it's the unraveling of the old beliefs, the old habits, sometimes some old relationships and things that you have to release to be able to step into what comes next. But so many women, it's the fear of not knowing what comes next that holds them back.

00:15:04 - Laura Gassner Otting
Absolutely. So that my. My favorite Eleanor Roosevelt quote is, you'd worry much less about what other people thought about you if you realized how seldomly they did. It turns out no one's paying attention. You could have renamed the podcast five times in the last two years. Maybe, like a handful of super loyal listeners would have noticed, but it's still just going to get automatically downloaded because they subscribe on their phone and they won't even notice. It's different. Like, they. They won't have everyone so wrapped up in their own selves. Like, nobody. Like, all the time that we spend worrying about what other people think about, it's this time that we're not actually worrying about what anyone else is doing. So, like, if we can't pay attention to them, they're sort of not paying attention to us. Right. Like, so we'd worry much less about what other people thought about us. So we realized how settling. They did, number one. Number two, I'm glad you told me that I could curse on the show because Vernee calls it the Great unraveling. My mother called it fuck you. 40s. I'm in my 40s. I hope I'm gonna get a little better. I hope I'm not gonna get that much worse. But I'm probably. This is probably who I am as a human. And like, if you like me, awesome. And if you don't, you, that's fine, you can find someone else, right? Like, it's okay. We don't. You don't have to be for everyone, my friend Aaron King likes to say. Or her grandmother always said something like, it's better to be someone shot of whiskey than everyone's cup of tea. And I think that's such a great quote because they're like, when we're growing up, we're told you have to get an A in science and an A in civics and an A in physical education and an A in English and an A in math. And it turns out that as grown ups, we do have affinities towards certain subjects. Our brains do work in certain ways. Like science tells us there's left brains and right brains. And yes, we should all know how to, you know, add a column of numbers and write a sentence. But like, I am not going to do string theory, physics. I can write the hell out of a book, but I can't. Like you asked me to do long division and like things start to get a little shaky. Like, are you smarter than a fifth grader? No. Like definitely not. For math is considering. So why should we be? For why should everybody love us? And why should we love everybody, Right? I saw some meme the other day that said something like, you know, don't worry if everybody doesn't love you. You don't love everybody either. It was like, it's so true, right? Like it's so true. And I kind of learned at this point, honestly, that goodbye is a gift. Like being able to say goodbye to somebody, being able to release them from pretending to like you. It's a gift to them. It's a gift to you. It's a gift. It's all right. You can have people in your life for certain seasons and certain reasons and you people's lives for certain seasons and certain reasons. But we don't have to like, you don't have to be best friends forever and ever with that high school friend who doesn't serve you anymore. And, and by serve you, I don't mean like wait on you. I mean like who doesn't bring out the best version of you.

00:17:44 - Megan Gillikin
Yeah. So what do you think, Laura, when it comes to finding yourself in a place where you know that where you are right now, whether it's a job, a relationship, a friendship, the business that you've built, how do you know? Like, when have you gone too far? And I Guess I would ask this question of your own experience. Like, you've, you followed the curiosity of doing fun things with fun people. But have you ever missed it where, like, you keep going a little bit too long, find yourself in a place of. I know something that you've talked about in your books is burnout, right? So you've never found yourself in a place of like, oof, I've, I've hung on too long here. And now to make this move, it's going to require a little bit more effort.

00:18:28 - Laura Gassner Otting
Yeah, the Whitney Johnson talks about this a lot. She has this thing called the S curve, which if you imagine a sideways S at the bottom, you're like, I don't know what I'm doing. And everything is steep and it's really hard. And then you start climbing up the S and you're like, oh, okay, I'm, I'm starting to figure it out. I'm, I'm, I'm getting there. I'm, I'm, I'm getting a few wins under my belt. My confidence is growing.

00:18:47 - Laura Gassner Otting
And then you get to the top of the S and you're on cloud nine. You're like, on top of the world. Everything is working. You're like, this is awesome. I could just do this forever. And what she says is that when you get to the top of the S curve, the S runs out, right? And if you don't leap to the next S curve, the next adventure, the next hard thing, you start to self sabotage.

00:19:04 - Laura Gassner Otting
And I was like, that's nonsense. Like, who would ever self sabotage? They're at the top of their game. So she asked me to tell her a story about a time when, like, things didn't go so well when I was running my company and I, I thought for a moment, and I remember there was this time when I got called in to do the head of a family foundation for a major hedge fund founder.

00:19:24 - Laura Gassner Otting
And I walked into his office having done very little homework. I mean, I had been doing this for 15 years at that point. It wasn't that I was sick of pitching, I was sick of winning. I was bored. Like, it was just easy. Like, I would just, I would pitch and I would get it and great. Awesome. So I got a little arrogant, I got a little complacent, and I really didn't do any research.

00:19:43 - Laura Gassner Otting
And I'm in the elevator on the way up and I'm like looking up the dude and I can't find anything else about it. This story doesn't make me look very good by the Way I can't find out anything of one, it's relatable except two things. Number one, he's like an Internet ghost. Like, it's hard to, I mean, he's a super, like, famous hedge fund dude, but he, I can't find anything about him except that he has outdoor ice skating rinks at all of his homes all around the world, like, including the one in the Caribbean.

00:20:06 - Laura Gassner Otting
Right. Like, he's really dedicated to his kids hockey. And I, I get to his office and he like, barely looks at me because it's the middle of the trading day. So he's like, staring at the screens and there's like 15 lawyers sitting around this enormous conference table. And he's like, yeah, yeah. He's like, so, yeah, good, good to see you. I, I need somebod give some money to hospitals because my wife and are getting older and the kids are getting a little older. So we need somebody who give somebody to hospital to colleges so that they can get into a good college.

00:20:32 - Laura Gassner Otting
So can you do that? And I literally, like, that was all he said. And I stood up and I stuck my hand out across the table, and I was like, sir, it's been great to meet you, but you've got like 15 lawyers here that can write those checks. And he immediately, like, turns to me, like, away from the trading debt, like, turns to me and he's like, what would you do? And all the lawyers stop breathing and they climb underneath the table. And I said, well, sir, in our extensive research about you, it appears that you are very private. So I don't think you want your name on the side of a building, but also that you care deeply about your kids sports.

00:20:57 - Laura Gassner Otting
So what if we created the world's foremost partnership between hospitals and colleges about childhood sports concussion issues. And he was like, yes, go do that. And I'm like, how? And so all the lawyers, like, come up from under the table, they start breathing again, call a return to their face. And I said, what if we found you somebody who would spend more than 17 minutes helping you come up with a philanthropic strategy? And he's like, great, paper it signed me the contract.

00:21:20 - Laura Gassner Otting
And I was like, okay. I walk out of the office, I get in the elevator, go downstairs, and I text my business partner, I think I need an exit strategy. And I had stayed too long. I, I, I was no longer excited about the win. I no longer tasted blood. I was no longer challenged by it. I knew how to do it. I knew how to do the fancy dancing and to, you know, get the client Accepted.

00:21:42 - Laura Gassner Otting
I knew how to do the things. And it just. It's not that. To do the jigsaw puzzle over and over and over and over. It gets a little boring. Like, you figure it out after a while. And so for me, the true sign is like, when things are going well, it doesn't excite me to grow and to learn and to continue to innovate. Like, some people love running things, I love creating things.

00:22:05 - Megan Gillikin
Yeah, yeah. What a powerful thing to acknowledge too, because I think I've felt that too in my own career. And you feel this belief that, like, I created it, I need to, I need to continue to evolve it and to pour into it, but it might be that, like, it's time to build something else.

00:22:22 - Laura Gassner Otting
I think a lot of times we don't leave. We get stuck where we are because we're so worried as women that we need to take care of every single person, we forget to care about ourselves.

00:22:34 - Megan Gillikin
Yeah. Oh, man. It makes me think of the idea of. I joke sometimes when I was speaking on stage about being a recovering people pleaser. Right. It's like letting go of. Letting go of the people pleasing tendencies and then stepping into, like, advocating for yourself. And then you're like, wait, am I a bitch now? Like, I don't know, like, you're questioning the boundaries that you're setting and the new ways that you're showing up in your friendships and marriage and all the things.

00:22:59 - Laura Gassner Otting
Yes. You know, a fundamental mindset shift moment for me when I was running that last company was I worked with an executive coach and he said, listen, Laura, at any given time, a third of your staff are going to love you and a third of your staff are going to hate you, and a third of your staff are not going to give a shit either way. And it's your job to know which third is where and to decide which ones of those you actually care about moving.

00:23:25 - Megan Gillikin
Yeah, yeah, yeah.

00:23:26 - Laura Gassner Otting
But that last part, to decide which ones you actually care about moving, is the most important piece because, you know, we had somebody on our team who, who hated me. She, she worked for me. I paid her. She hated me because she never quite felt like I was paying her enough. She, she, she was a great salesperson. She was a squeaky wheel. She delivered absolutely. But she was toxic in our culture. And she never quite felt appreciated enough, even though she was appreciated financially way more than everybody else, sometimes even more than me, but she never felt appreciated enough and she did not like me. And I didn't care because it didn't matter if she Left it, it'd be fine.

00:24:00 - Megan Gillikin
Yeah. And that's one of those, like, growth moments, right? You have to be able to let go of that. Something that I know you talk about in, I think it's wonder hell is the idea of each level, as you're leveling up, has this new devil. Can you tell me a little bit about, like, something specifically for you as you. Because you have this confidence, you have this just like, I will figure it out. I've. I've. I have navigated changes and continued growth. But is there something that, like, you keep running into as you level up?

00:24:31 - Laura Gassner Otting
You know, it's funny, people say to me all the time that I seem like I have a lot of confidence and. And I don't actually know that I do in the traditional way. We think of it like, we think about confidence as faith. I just had faith. Things are going to work out. Like, I'm awesome. Things are going to be great. I actually don't have that. I'm like a giant baggage of insecurities. I'm. I'm like a spastic bag of moxic energy or mox of moxie and sebastic energy. And I'm just like, I'll figure it out. It's not that I believe always that things are going to work out. I don't have faith in that way. What I have are facts. I have facts. I can look back and I can say, in everything I've done up until this point, I've been able to solve the problem. I've been able to figure out the puzzle. My favorite quote from, from Quincy Jones is, I don't have problems. I have puzzles. Which I think is a great shift there. I don't have problems. I have puzzles. So when I think about the puzzles that I've solved, how have I done it? I've asked questions, I've created the right networks, I've built the right skills, right? So if I've done those things up until this point, then it's not that I have faith that I can do it again. I literally have a track record that I can lean on that gives me confidence that if I have been able to do the things that help me solve problems and puzzles, then whatever problems and puzzles arise, I can solve them again because it's the same skill set. So even though I'm in white space doing things like I'd never spoken on stage before, I'd never written books before, but, like, how did I learn how to do anything I'd never done before? By asking questions by learning, by watching role models, by, you know, observing what other people do and then figuring out how to put my own stamp on that. So, like, we've all done all the things that we're going to do next. We've just done them in other iterations. Somebody said to me when I. When I sold my company and I was thinking about, I kind of wanted to get into the venture capital as the next thing. So I was like, I've spent 20 years sizing people up and being an entrepreneur and, like, anybody who run a business plan, but, like, who's going to be able to, like, actually make it work? Like, I can figure out those people. And I talked to a whole lot of venture capitalists, and I realized that I thought venture capital was really interesting, but I didn't want to work for any of the venture capitalist dudes, so I didn't go into it. But as I was thinking about it, I was a little bit, in the beginning, overwhelmed by just everything people were saying in these interviews, in these meetings. And I talked to a friend of mine, and I'm like, dude, I'm so out of my league. I'm so, like, out of my comfort zone. And he's like, you're not out of your league. You're just out of your lexicon. And that was so interesting to me because he was like, people just using different language, but it's the same stuff. They're still trying to figure out the value of the deal and whether or not somebody has the skill set. They just use different language. And so the language itself, the lexicon, seems foreign, but the way that they think is the same. You're not out of your comfort zone. You're out of your lexicon.

00:27:23 - Megan Gillikin
Right? Yeah. And you know what? That speaks to me so much because I think, again, something that I can see as maybe a mindset shift over the years is it used to be like, oh, everybody else has it figured out but me. It ties back to that inner critic and that imposter syndrome of, like, it seems like this one person has. Has everything figured out. This person has this down, and I'm still learning. And then as you progress, you realize, just as you said, I mean, you do, you do emanate confidence to me. But the reality is, like, you're still figuring things out, and you're still using facts to inform what your decisions look like moving forward, but you still have those questioning moments. And something that helped me process imposter syndrome and that inner critic is even those people, those people like you, the people that have created success. And outwardly we could read your bio and it would be like, holy shit, she's amazing. She's made it, she's made it. But there really is no spot where you've made it. And you don't question things moving forward and decisions that you've made in the past.

00:28:30 - Laura Gassner Otting
There's no spot. And you know, when I first started speaking, I sat down with Allison Levine. And Allison Levine was the captain of the former first all Women's American expedition up Everest. So pretty impressive human. And she was like, Laura, she's like, you should be repped by a speaking bureau. And I was like, allison, I'm not good enough to be repped by a speaking bureau. I'm not impressive enough. I didn't climb Mount Everest. And she said, laura, when I first walked into a speaking bureau, they said, oh, you climb Mount Everest, but did you saw off your arm in order to get back down? Because we already got that guy. Somebody's always going to have a bigger story, a better story or whatever it is. There's always somebody. Like my, my father grew up not with a lot of privilege and he grew up in, in Brooklyn. He used to walk down every day to, to Brighton beach and he'd look out over the, the bay off of Long island and he would see these big boats and he was like, one day, one day I'm going to have one of those big boats. And so, you know, he became a doctor, he made plenty of money, he bought himself a big boat. And he took that boat from Miami where he grew up, all the way up the Intercoastal Waterway, all the way up to the New York City harbor. And he pulls the boat into the slip and he sits down the back of his boat and he's feeling so proud of himself. And it was like a 56 foot boat, just, you know, not a small boat, right? 56 foot boat. And he's sitting on the back of the boat and he's having his gin and tonic and he's so proud of himself. And all of a sudden the guy in the next slip parks a 60 foot boat and it's like somebody's always going to have a bigger boat. So I grew up with this, like someone's always going to have a bigger boat. And like the 60 foot guy, somebody pulls a 75 foot in yacht next to him, like, yeah, you know, if you play that game where all you're doing is comparing yourself to someone else, not only do I think that comparison is the root of all unhappiness But I actually think comparison is the root of all mediocrity, too. So when we spend this time thinking, like, when you're. When you're Hudson and Futon about, like, should I rename the podcast? And what if people don't like it and what are other people doing? You probably spend a lot of time staring at other podcasts at other people and saying, well, what are they doing? And is that working? And how is that? And if you're went to what everybody else is doing, we end up meaning towards the middle. Right? We, like, go to the average because we're doing what everyone else is doing, and that steals away all of what makes you special and all of what makes you unique. And I think rather than comparing ourselves to everyone else so that we can just be like everyone, like, somebody already said, this is good. I should be like that. We should really strive to become a category of one. What do I do that's new and creative? Because it's not that I'm confident.

00:30:59 - Megan Gillikin
I'm just.

00:31:00 - Laura Gassner Otting
I'm just okay standing tall being me. Confidence would be, I'm standing tall being me, and I know you're gonna like me. I'm just standing tall being me. And I'm actually okay if you don't, because I've had enough people not like me at this point that I know I've survived, and it'll be all right. Like, there's enough success to go around. Yeah, the fuck you 40. There's like, I don't need to get every deal. I don't need to get every keynote. I don't need to sell every book. Like, there's enough success to go around. All of us can jump into the success pool. Like, there's plenty of it there. So I don't have to hoard and I don't have to hide, and I don't have to pretend that, like, I'm just, like, you don't worry. Like, I can be over here and, like, some people will like me and some people won't. And if you're an entrepreneur or if you're running your own business or if you're a senior executive, like, you know that you. You will not make change unless you actually make change. So we should all be okay making change.

00:31:48 - Megan Gillikin
Yeah. And there's two things. One, as you're talking about, like, stepping into. We've.

00:31:54 - Laura Gassner Otting
We've.

00:31:54 - Megan Gillikin
We've sort of talked about the idea of stepping into what's next and the fear that comes along with that. And I find comfort in you speaking to what you use to make these decisions are the facts. Like, okay, I'm ready for a career change, or I'm ready for a relationship change, or I'm ready for starting that business and walking away from my corporate job that I've had. It's using the facts, right, of what you've done before, what you've accomplished, what you know, you've been able to overcome, to lean into taking those next steps, even though you're kind of afraid.

00:32:27 - Laura Gassner Otting
And it's not always worked out. And I've survived that too. So because I. I talk a lot about entrepreneurship, I end up speaking at a lot of entrepreneurship conferences. And during Q and A, there's always somebody who's like, excuse me, like, what would you do if you failed when you started this company or that company or this whatever? And I turn it back on them. And I'm like, well, you're here at an entrepreneurship conference. You're an entrepreneur, right? Well, yeah. And I'm like, what will you do if your thing fails? And they're like, oh, well, I mean, I guess I'd like, go get a job in some cubicle somewhere and then write another business plan and save up money and then let it go. Start that. And I'm like, okay, great. What will you do if you succeed? And I've been asking this question for. Been speaking on for eight. For eight years, and I've never gotten an answer. What will you do if you succeed? And they are flummoxed. It's like crickets. Because we spend so much time worrying, like, what will I do if I fail? That we never actually spend time thinking about succeeding. And when I was writing Wonder Hell, I started thinking about manifesting, and I was like, manifesting some bullshit. Like, what is this manifest? You put something on your. On your vision board and suddenly it comes true. Like you put your sale to Japan and suddenly like, you want to go to Tokyo and suddenly there's a sale of Japan. Like, that's nonsense. And then I started reading about the science, and what I learned is that your brain takes in 11 million bits of data every single minute. But it. 11 million bits of information come at you. How do you like, how warm is it? How bright is it? What does it smell like? Like, of the proprioception. Like, how do I feel in my body? Like there's so many different senses. There's like 53 senses, not just like the five that we think about. And. And if you're. All of your senses are picking up all this data, it has to pick and choose which gifty to take. So if you write on your vision board, I want to go to Tokyo, then all of a sudden your brain is like, oh, look, there's a sale to Tokyo on that bus. You didn't manifest the bus or the sale to Tokyo, but you told your brain of the 11 million bits of data that I'm getting, please pick these 50. If you happen to see something about Japan, pick it out. And so, as we are starting to think about who we are and where we're going and what we want to achieve, this idea of who we want to become is super important. Like, how do we see ourselves in that way and. And put that out into the world? Because once we start doing it, that's when all those opportunities start coming our way.

00:34:46 - Megan Gillikin
Wow, that's so powerful. I want to be like you when I'm 54.

00:34:50 - Laura Gassner Otting
Look, when you were renaming your podcast, you probably spent a lot of time thinking, like, oh, what if nobody. What if people don't see it? What if they don't like it? But you probably didn't spend a ton of time, like, really exploring, well, what if it's successful? Where could it go? What markets could I be in? How big could it be? Because if we spend time focusing on that, then as those opportunities arise, we can actually jump into them. Like, we can actually get luckier with them. So I spend a lot of time thinking like, okay, this is where I want to go. This is what it will look like if I succeed. So if I want to be. If I'm in New York and I want to be in la, you can start, you know, driving. What is that? Southwest. And if you're like a couple degrees off, it's like, not a big deal if you're only going to, like Philadelphia. But I actually don't know if Philadelphia, Southwest, and New York, don't at me if that's wrong either.

00:35:41 - Megan Gillikin
Yeah, but.

00:35:42 - Laura Gassner Otting
But you get the point, right? Like, if you're a couple degrees off, you're not going that far. It's not a big deal. But suddenly it becomes a bigger deal if you're going all the way to la. So I spent a lot of time saying, like, okay, what's my big, hairy, scary goal? When do I want to get there? One year, two years, five years? And then what are the touch points in between? Like, will I know that I'm on or off track at three months, at six months, at nine months, at 12 months, in terms of the investments that I'm making, the time that I'm spending Anytime anybody tries to sell me, like, we'll manage your social media and get you a bajillion followers in a year. I'm like, okay, how many followers am I going to have in nine months and six months and three months? And they're like, well, what do you mean? I'm like, well, you can't tell me a bajillion in a year and then not tell me what the. Right. So I spend a lot of time thinking about, like, what's the big, hairy, scary goal? What are the short term metrics I have to meet in between? And then what's my plan B if I'm not meeting them? And once you've thought about all of that, then the change becomes far less scary because you don't. It's not this unknown.

00:36:36 - Megan Gillikin
You.

00:36:36 - Laura Gassner Otting
You have a plan no matter what happens.

00:36:39 - Megan Gillikin
Yeah, I love that. And it makes me think about something that we talked about at the beginning of this recording. We talked about the people that are in your circle, the people that you lean on when you're thinking about making big decisions and how you may want to question that process. And it made me think about. For me, when I start reaching out and seeking opinions from too many people, that's sort of my sign. That's my sign that I have the answer. But I'm avoiding listening to it because I'm seeking someone else to tell me what to do instead. Similarly with the podcast, I think I spent two years being like, what do you think about this name? What do you think about this direction? What do you think I should do here? And then I realized someone would say, oh, I don't really like that. So then I would go back to the drawing board. And finally I got to the point where I was like, man, I just need to sit with it and make it what I want to make it. I need to stop seeking approval from others and find that intuition that oftentimes, truly, for me, it is a red flag when I am asking and pulling too many people about anything that I'm avoiding getting quiet and listening to myself for sure.

00:37:44 - Laura Gassner Otting
I mean, your intuition knows the reason that we exist today is because our ancestors weren't fast enough to outrun the Triceratops is because their intuition told them the Triceratops was coming. Right? So, like, millions of years of DNA is given us very, very good intuition. That's actually the other thing about comparison. When. When Limitless first came out in 2017, 20, 2019, I saw all these other authors that were posting, like, here are two different book cover options what do you think? And they were asking all their followers to vote. And I put up book options and I asked my followers to vote and I looked at the numbers and I really thought that it should be the yellow cover and the orange cover was winning. And I didn't understand why that was. And had I picked what everybody thought was the right thing, it would have been the worst cover ever because I saw everybody else doing it. So I thought that was the way to do it. And then I stopped and I was like, you know, who are the people who like the orange cover? And what I realized is that the people who like the orange cover were like a bunch of dude bros who were very like traditional jobs. And the orange cover was very like Harvard Business Review corporate. And the yellow cover was very like, empowering and you can do it and Right. Had a little femininity to it. And. And I realized that when I was comparing myself to other people and doing the things other people were doing, I was literally not listening to my own intuition and I would have made the wrong choice.

00:39:11 - Megan Gillikin
Oh, so good. Okay, Laura, I know you have a train to hop on this afternoon. I'd love to one. Before I ask you a final question, I'd love for you to share where our listene can connect with you.

00:39:24 - Laura Gassner Otting
Your.

00:39:25 - Megan Gillikin
I know you have a few books, but is there one that you're like, this is the. This is where you start. If you're starting with me, read this one.

00:39:32 - Laura Gassner Otting
Well, I think if you're starting with me, you should read Limitless. And Limitless is all about how to define success for yourself. So if you are somebody who has gotten to a certain point in your life and you're like, you know, I'm successful, but I feel like I've been filling in everyone else's checkboxes to everyone else's definition. It's. It is my way of to trying. With 20 years of experience in executive search, telling you what I learned actually creates both success and happiness. So that's limitless. Wonderhell is if you really know who you are and you're pursuing something you actually care about and you're working really hard and you're successful, but it's just getting harder and you don't understand why, then Wonderhell is, you know, it's amazing, it's exciting, it's wonderful. But I'm also filled with anxiety and uncertainty and imposter syndrome and stress and burnout, then Wonderhell is the book for you. My name is Laura Gassner Otting. All my friends call me lgo. So you can find me all over the socials at hey lgo.

00:40:21 - Megan Gillikin
I love it so much. Well, Laura, final question is, we covered so much amazing nuggets of goodness with you, but if there's one thing that you want to leave women listening to this, if there's one thing you want to leave listeners with, what piece of advice would that be?

00:40:36 - Laura Gassner Otting
I have entered in 2025 my fuck you, pay me era. And what I mean by that it is I am done giving freebies to people who don't appreciate me. I'm done negotiating my price with people who don't see my value, and I'm done apologizing for taking up space any longer. And I would encourage every woman listening to this as they walk into any negotiation with anybody, to think, what would a mediocre white dude do? Fuck you pay me. I'm worthy.

00:41:09 - Megan Gillikin
That one was packed with nuggets, right? From unlearning the old roles you've clung to, to leading yourself with evidence instead of fear, to navigating those identity shifts that come with growing and evolving, Laura brought the clarity, the wisdom, and the fire. Two things she said that are still echoing in my head. Stop taking votes from people whose voices don't count. And you don't need everyone to like you. You just need to be fully for you. And if this episode stirred something in you, if it made you think, if it made you feel a little more seen, I'd love for you to share it. You can tag us on Instagram or Real with Meg, you can send me a dm, or you can share this episode with a friend who needs to hear it. And don't forget to follow the show wherever you're tuning in from so you don't miss what's coming next. Thank you so much for being here, and I can't wait to share a new episode with you real soon.