We are taught that in order to be brave, we must be fearless. But what if fear is actually the one thing that will push us to be our best, most successful self?
In this kickoff episode of Dare to Interrupt, host Courtney Stanley speaks with Judi Holler, author of the best-selling book Fear Is My Homeboy and CEO of HOLLA! Productions, shares how leaning in to fear can bring you to levels of achievement that you only dream of. Listen now!
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Courtney Stanley: Hi everybody, this is Courtney Stanley and welcome to the very first episode of Dare to Interrupt, a listening experience where you have the opportunity to be a fly on the wall and sit in on honest, unfiltered conversations with women who are considered to be the most influential and inspiring leaders in the world of events, hospitality, tourism and beyond.
Throughout their careers, these women have dared to interrupt conversations, their own comfort zones, and societal norms to hustle toward the greatest levels of success. I could not be more thrilled that the very first guest on Dare to Interrupt is someone that I have watched chase her dreams and hustle to make them a reality and to truly build her own empire.
Without further ado, I introduce you to Judi Holler, CEO of HOLLA! Productions. Hi, Judi.
Judi Holler: Hi, Courtney. And what an introduction, if I had a mic besides the one that I’m using right now I would drop it. I don’t know if I want to drop this mic, but well done, what an introduction. And I’m so proud to be on this podcast and just so nice to be here with you.
Courtney: Well, it is my pleasure. You are somebody that I think anybody who has met you or has seen your Instagram or has seen you speak before knows that you are the real deal here, a woman that has a serious, amazing brand, and you’re somebody that we all look up to. It’s my honor to have you here today.
Judi: Thank you so much. I receive that and I’m so grateful and can’t wait to jam.
Courtney: Awesome. You have been killing it over the past however many years, but I feel like this last year, or maybe even two years, you have just completely climbed to the top of the ladder, and you published your first book. Is that right?
Judi: I did. My first book called Fear Is My Homeboy, came out May 28th, 2019. So it’s been, oh my gosh, we’re recording this in January 2020, so it’s been about eight months. It’s certainly been a whirlwind, no doubt about it. (Judi Holler, pictured)
Courtney: Yeah, I bet. Tell the audience, I’m sure we have some fans that are listening in that have read the book before, but tell our audience a little bit about Fear Is My Homeboy. What is it about and what inspired you to write it?
Judi: I love this question. I think we should back into it a little bit and reverse engineer it because before I began writing and before I became a creative entrepreneur, and before I became a podcast, host and speaker, I was a meeting professional. I started in the hospitality industry when I was 13 years old. I mean, I’ve bussed tables. Yeah, I’ve washed dishes. I’ve ran bars. I mean, I’ve done it all.
And I was a bartender working for Hard Rock Cafe at the time in St. Louis and my manager’s wife was on the board of MPI St. Louis, Meeting Professionals International, the St. Louis area chapter. This is a cool story.
So, I was looking for work. I had just graduated college, I was a communications major with a radio television minor and 9/11 had happened when I was graduating in 2001. And the world just sort of stopped. And I was really hungry to get out of the restaurant industry and out from behind a bar and really into something more stable, but you couldn’t find a job in radio or television to save your life.
And if you did, you were getting like $15,000 a year and you had to move to like Omaha, Nebraska and I just wasn’t in a position to do that. It was just really hard to find work and just work in general in that goofy time. And so, she said to me, “You’re coming to this meeting with me,” and I go “What are you talking about?” She goes, “You’re coming to this MPI meeting with me,” and she kind of explained what it was.
I knew she had this really cool job in catering sales for the Marriott in downtown St. Louis. And I had no idea. I mean, I just thought hotels were like sleeping rooms and a front desk. I had no idea there was this whole other world of live events and meetings, and why all that mattered, and why it still matters even more than it did back then and why meetings mean business, right? I had no idea.
So, I go to this meeting. I have these nerdy business cards, resumes printed up—back when you actually used paper resumes—and I literally talked to everyone. I was like little Bambi—more like a golden retriever—just super excited, trying to meet everyone and long story short, I ended up meeting—there’s a woman standing in the corner and I tell this story in my book. Her name is Heather Allison Smith, she’s now with Marriott and opening the Marquee, or not Marquee, but going to work for the Marquee, not opening the Marquee in New York, but Marriott and Ritz-Carlton for a long time, but she was standing by herself, had just moved to St. Louis. I go over and say hello. And the rest is history.
She gave me my first job in the business. And MPI really walked me through what was the beginning of my career and really was with me as I was building my career when I moved into Chicago. So, I share that story because I didn't start out thinking I was ever going to write a book or become an entrepreneur or create things for a living. I started as a meeting professional, and it really holds my heart to this day. And even because I don’t open hotels anymore.
I went on to build a career in the hotel industry and worked for Omni and Starwood and Marriott, and all the big hotel companies, and even though I’m not doing that so much anymore, I’m still in the live events business.
I mean, I speak on 50-60 stages a year. I participate in those live events, and it’s just such a powerful, powerful tool, you know, meetings and coming together face-to-face. So, I am an event prof. I’m proud of that. I come from the meetings world, I do believe so much in the power that they have. And it’s just really shaped my story in so many ways.
Courtney: Yeah. Yeah. It’s an incredible industry. I feel really fortunate and super blessed to be a part of it. And I do think that being asked at such a young age to join a community and to get involved, I think that’s such a great opportunity to first and foremost, just say, yes. Start opening those doors and saying yes to those opportunities. (Courtney Stanley, pictured)
But secondly, I think it really points to the importance of actually diving in and what you put in is what you’re going to get out. It sounds like that’s what you did, starting very, very young. And you just kept engaging and putting in the work and showing up and it served you so, so well.
Judi: Oh, yeah. I mean, my volunteer work and certainly getting involved with an association at a young age was one of the smartest things that I did for my career because it taught me so many things outside of my paycheck. And outside of my paid job.
I really found it, before I started studying improv because I ultimately moved to Chicago and started studying improv, which was really another flashpoint in my career. But MPI was my first and getting involved in the industry was my first because it gave me an opportunity to play, and to go create things and figure things out, and meet new people and manage other people and figure out what works and what doesn't work.
It just really allowed me in a non-corporate environment to go play and to try things out into work to leave things a little bit better than than I found them and, and I went on to be president of the Chicago area chapter which was awesome.
And it taught me so many things and expanded my network and brought some of my best friends and best mentors into my life. It’s really where I met so many business owners and it really got me even hungry to that idea.
So, when I was ready to start the website, I mean I’ll never forget Dalia being like “Dalia, D, I got it. I need a website, and I have no idea where to start.” She's like, “I know some people.” So, I bought her sandwiches at Panera. I think I bought her and Ken—I think I bought them sandwiches and soup at Panera Bread, and they helped me figure out the website.
So again, it was starting to transcend what we were doing in the chapter. It was really bleeding into my life in so many ways. And it just allowed me to level up on all fronts. I was leveling up my brand in the industry, but I was leveling up my business skills and I think I mean, that is a gift.
You can really find opportunities inside any association that's relative to your industry, to boss up for yourself, to get uncomfortable, to try new things on and to meet new people. And that’s what I did. I listened, sometimes I failed, and I got it wrong. I might have made some mistakes. I might have ticked a few people off.
But there were times we got it right. And we tried some new things. And it really worked. It was all about allowing ourselves to fail, fail often and fail with love and courage, because this is how we were able to keep going and pivot and make it better the next time.
Courtney: Yeah, I think that totally makes sense. Judi, have you always been comfortable with facing fear or getting back up if you failed? Or was there a turning point where you decided that you were going to look at life a little bit differently and just start living your life a little bit differently?
Judi: Yeah, I love that question. You know, I’m scared most days. I always joke that I’m a big old fraidy cat. The difference between me and other fraidy cats is that I keep going. I don't let the fear stop me and, in our community, we come to build this beautiful community around the ideas in the book Fear Is My Homeboy, and we call ourselves “fear bosses”.
And in this community, we have chosen to be the boss of our fear. It doesn’t mean we’re not afraid. It means we’re brave. And I really challenge this notion of fearless. I mean, the world is telling us all to go be fearless, right? Fearless t-shirts and jewelry, bumper stickers, all this stuff. And I think that’s why we’re confused. I don’t believe that we should be fearless.
I think it’s an unrealistic notion. I mean, if you were really fearless, think about it. You would do all kinds of crazy stuff. You would never pay your taxes. You would never go to a doctor; you would get on elevators at three in the morning with crazy people. You’d walk down dark alleys alone at night by yourself. And there’s this book called Big Magic by Elizabeth Gilbert. If you’re listening and you haven’t read that book, and want to think differently about your fear, specifically if you’re creative, run and get it.
But in that book, Elizabeth Gilbert writes, “The only fearless people I know are five-year-olds and sociopaths.” And I don’t think we want to be either one of those, right? So, the goal should never be fearless. It should be brave. It should be figuring out how to fear our less.
[2018 Year in Review: #MeetingsToo]
And the big flashpoint for me, where this really landed for me, was when I started studying and performing improv at Second City in Chicago. So, by day, I’m like hotel sales, national sales manager, you know, doing all my MPI stuff, slaying my career, and by night, I’m taking improv and I’m becoming a student of that theater. And it was the first time I started to see failure celebrated, and mistakes became our core curriculum for success.
See in my corporate environment, that was very different. Things felt very stiff and rigid, and we had to stay in the lines and don't be yourself too much, but be yourself—but not too much. And it was a little risk at first, but in the improv theater, we were being encouraged to lean into discomfort, to dance with discomfort and to do it daily and this bled over into my sales career, into my MPI career, my industry career.
And it really blew me away because it allowed me to get uncomfortable on purpose, regularly, which grew my brave muscle, and I do believe courage is a muscle. In order to strengthen it, in order to get any good at anything you want to do inside and outside of this industry, you have got to have the strong muscles that will hold you up, so that no matter what happens, you know, you got this.
So there’s self-love and confidence and trust and all that’s involved. But the core—the core of the work in the improv theatre and really, in my work on fears, is the idea of experimenting with our fear every day on purpose, because I believe this is what can make you very, very brave.
Courtney: Yeah, I think that’s fantastic advice. And something that I actually think that a lot of professionals within the meetings and events community would say is that it’s so ironic, Judi, because I think a lot of people are afraid of being uncomfortable and stepping out of their circle or their network of people, once they establish, you know, ‘I have my friends here, I know who’s going to be at this event.’
But it’s ironic because this industry is so focused on the meaningful relationships that we build, and really continuing to grow our circle and to ask what we want and to find mentors that embrace our passions and that grow us. But I think that a lot of professionals actually do struggle with really stepping outside their comfort zone and meeting new people, whether it's at a networking event or a conference or even the new person that shows up at the office.
How would you encourage people to get out of their comfort zone and to really get to know new people and to ask for what they actually deserve and want?
Judi: I love this so much. Let’s break this down a little bit. Here’s my advice: I’m going to advise everyone, introvert or extrovert—because I’m an ambivert, I kind of live in the middle of the spectrum—I get my energy through my quiet creative spaces, but I love to be with people. I kind of am in the middle of the spectrum there.
So, whether you’re an introvert an ambivert, or an extrovert, this will apply. I’m going to challenge everyone listening to become a fear scientist. And this means that you will begin to experiment with your fear, and you’re going to start small. So, fear experiments can look like just making it a game.
Just sit in the front row of every meeting you attend, making it a game with yourself to raise your hand first in the meeting or to speak up first on the conference call to say, ‘Yeah, I’m going to lead the sales meeting or I’m going to take a selfie in public to get better at not caring what other people think about me. Yeah, I’m going to start the Instagram account. Or maybe I take a different drive home from work or I swapped my coffee for tea or maybe tomorrow I’m going to take a cold shower.’ You see what I’m saying?
You don’t need to jump out of a plane or climb Mount Everest to be brave. You can do small everyday things to really work your brave muscles. So, that’s number one—start small, start experimenting with your fear. Start doing things a little bit differently than you’re used to doing them.
For example, today, if you see my Instagram stories, I’ve been doing no filter all day on Instagram. I’m like, no filter. Well, you know what I mean? And it’s silly that is even a discomfort in our day and age, but it is most people are filtering their face on anything that they’re putting online—43 is a fear experiment.
It’s a small thing, but it packs a big punch because it strengthens my brave muscle. But then fear experiments can also be really big things. They could be things like, ‘You know what? Today, I’m going to finally stand up for myself. I’m going to say no. I’m going to say yes. I’m going to leave the toxic relationship. I’m going toquit smoking. I’m going to take the job promotion. I’m going to sign up for the race. I’m going to start the business. I’m going to—whatever that looks like for you, so fear experiments can be big and small things that get you outside of your comfort zone.
As this idea relates to networking, specifically, Courtney, the question you asked me, how can someone kind of boss up for themselves when they’re out at these industry events? I’m going to propose an idea, a fear experiment. And I write about this in my book. And I don’t know if you’ve read this part, but it’s the part about conversation sparkers. Do you ever remember me talking about this, Courtney?
Courtney: I do, I sure do.
Judi: So, we’ll brief the audience, we’ll give you guys the scoop here. But this is an experiment, a fear experiment that you can try out today, tomorrow, at your next event at your next dinner party, the next time you’re sitting around a table with a bunch of strangers, to boss up for yourself and to stand out and to make a brave move for yourself. I believe a lot of us aren’t remembered at these events, we always get upset. We’re like, ‘Oh, so-and-so senior leader doesn’t remember me. She’s so stuck up or he never remembers my name. And he’s just a big jerk.’
You know what, I think we have to own it. I think we have to become someone who is memorable. It is not my job to remember you. It is your job to make sure I don’t have a chance to forget you. And the reason we’re getting lost in the shuffle, the reason sales people aren’t standing out and they’re coming home from these big trade shows with no leads is because they’re asking these boring, safe questions that we always ask because we’re afraid to try anything new and most of us feel really awkward in networking events.
So, I think having a social script is a powerful way to be brave in a networking event. In my book, I write about conversation sparkers, questions we can ask to flip the script from these boring, safe questions we always ask and lean into more big talk questions.
If you want a bigger life, if you want a bigger paycheck, if you want bigger connections, we have to ask bigger questions. So, this may look like instead of saying, ‘So, what do you do? Or so where are you from? Or so, how are you?’ These are boring, safe questions, and nine times out of 10, you’re gonna get the same response, which is going to be ‘Oh, I’m good. I am crazy busy. Things are just so crazy.’ I am crazy busy. Tell me something I don’t know. Right. So, could we flip the script?
Some of my favorites are, ‘So, what was the highlight of your day?’ I love that question. The other one I love, ‘So, are you working on anything exciting lately? Or, how did you get into the industry?’ You know, so you can open up conversations with questions like that. Now oh, by the way, there is science behind words like “highlight” and “exciting.” They literally trigger dopamine and the other human beings’ brain, and you will watch them light up, they will get excited because you are triggering that emotion. And the bonus side effect is you become the memorable one.
So, Courtney, when you ask me what I’m working on, that’s exciting. When you asked me what the highlight of my day was, A, who doesn’t like talking about themselves, but B, you get me excited about the stuff that revs me up, which gives us a powerful, powerful conversation. C, it makes me remember you and D, you learn all kinds of things about me you would have never learned if you just asked me how I was. Because I’d probably lie and say I’m good or busy, and we just move on to something really random.
But when we ask these powerful conversation sparking questions, we can really have some big, bold, memorable, brave conversations that pack a big punch. So, my fear experiments, to everybody listening, go try one of these out and let us know how it goes.
Courtney: I love that, I really do. And I think something that you said early on is you talked a little bit about how it’s not the other person’s job to remember you. It’s your job to make yourself memorable. And I think that’s such an important point to make. Because I think it’s so natural for people for human beings to feel a little bit hurt if they’re not remembered, like maybe I wasn't important enough, or maybe I wasn’t good enough.
And I think that’s actually where those fear experiments start is really understanding and believing in yourself and knowing your value and knowing that you deserve to be memorable, but taking responsibility for how you show up and for the perception that you deliver the audience that you’re speaking with.
So, I think that’s such a good point. And I really I’m so curious, Judi, because you are somebody that I truly believe has evolved and your life has evolved in your career where you have grown from different sectors of the industry to where you are now and even as a person, it’s clear that you’ve done the work to really evolve into become some somebody that you’re actually really proud to be. And I think that’s so admirable.
[More from Courtney: Dare to Interrupt: First Meetings Industry Podcast Built by Women for Women]
But I also know that realistically that comes with growing pains and that comes with tough times and challenges. So, what are some of the things you have overcome or some tough times you’ve had to go through and had to face and really to embrace that fear to grow?
Judi: Hmm, such a good question. Yeah, I think it’s so easy to look at someone on the outside and to think oh my God, he’s crushing it or oh my God, she’s slaying it or you know, she came out of nowhere overnight success, you know, year all this stuff in the industry and beyond all the time, but I think in order to really transcend you know, an industry and just sometimes, listen, I’m in competition with myself, period. It’s an infinite game.
You know, it’s not, I’m in competition with myself and this, so I think we’re where I’m trying to go here is, I think the thing that has surprised me the most about walking into this new path of creative entrepreneurship and running a business and running a creative company and you know, traveling for a living and all of that. It’s managing the mind that has become I think the thing that I’ve had to work on the most, and the thing I guess I didn’t see coming.
I work harder on myself and my mental health than I do at my job. And you see me, I work hard because I know you do to your boss, right? So, I work my tail off, I could work every day. That’s how much I love what I do. And sometimes I do but you know, at least I love what I do, but it is—sometimes I gotta check myself before I wreck myself, but I work hard is what I’m trying to say. But I work harder on my mental stamina because I believe that none of this can work if I don’t work, and none of it will work if you don’t work.
No matter what industry, you’re in, what role you play in life, and a lot of people listening to this have busy careers and they have busy personal lives. They’re going to go to work every morning. And then they’re going to clock in at their second job when they get home after work and take care of their kids and their family. And maybe they’ve got a volunteer association and they’ve got a church and a neighborhood and friends and family. And it’s intense. And we will never be able to manage this if we’re not taking good care of who we are.
I think for me, really taking care of myself mentally, physically and emotionally, it’s been a really big deal as I’ve sort of stepped into this role as a business owner, but at the end of the day, you don’t need to own a business to remember that you are a CEO, you’re running a business every single day. And that’s the business of you. And if that doesn’t work, nothing works.
I think the long answer to your really powerful question is just that for me, I think that’s the thing that has surprised me the most, how much I struggle with my own inner demons and managing self-doubt and getting out of my own way and not feeling like an imposter. And then doing the work to really stay focused on the task at hand, the job the community, and the mission that we have inside the work I’m doing every day.
So, I don’t know. Hopefully, that gives you an answer. But I think we’ve got to really work harder on ourselves than we do at our jobs. And I think that’s what will sustain you over the long term.
Courtney: I think that’s absolutely right. And I think there are a lot of people regardless of industry, but there are a lot of people in our own community that just struggle with stress and anxiety and panic attacks. And I think there are more people that struggle with that than are actually talking about it.
And we, right, like this is a serious thing. And I personally have struggled with anxiety. I’ve had panic attacks that came out of what I thought was nowhere but not understanding that stress actually builds, and it doesn’t dissipate unless you really focus on getting rid of it. So, I love that you talk about the importance of investing in yourself and your own mental health and your own mental awareness.
And that’s really the place that you start and then not actually looking toward the people on Instagram or the people even sitting next to you and seeing them as nothing but success because behind that success is their own struggle. And they overcame a lot of different things and their stories and their experiences that you can’t see.
So, I love that you went there, and I think that’s so important for anybody who is listening to hear that because we all hustle, we all grind, but we also have our own stuff that we’re going through.
Judi: Oh my gosh, no doubt about it. And, you know, I think there is so much power and just owning it, too. And I think that’s gotten easier for me as I’ve gotten a little bit older. But, you know, now I kind of own it. But you’re right. It’s reverse engineering it. If it’s showing up, I write about my struggle with an ongoing panic disorder in my book, and it’s something I manage all the time, but it’s understanding, okay, well, why do I feel this way?
And if I’ve got this going on, that means that there’s something larger probably underneath some of these layers. So, if we’re not looking at that, if we’re not pulling up the hood and putting oil in the car or gas in the tank, it’s not going to last very long. So, yeah, I mean, there’s no shame in it. It’s just a part of life and I think there are more people struggling then we can even imagine.
And I think the way we’re connected, and the way we’ve got so much coming at us, and the world is changing at the speed of light, and we’ve got the media and the news and everything in the world breathing down our necks, I think we have to just keep our eyes on our own paper, come back to self-love, come back to self-trust.
[Courtney was featured in the Meetings Today October 2018 issue.]
And one thing I always like to remember, too, I think we get so worried, especially as we try to make moves in the industry, we try to go for a new job or try something new out or ask for a raise or lead a sales meeting or run the breakout or get published in the industry magazine, I think we get worried about what other people are going to think.
And I think what holds us back is other people’s opinions of us, and embarrassing ourselves and failing, but certainly judgment. And I struggled with that for a long time and what helped me get out of my own way, there was this fact and it’s this: we’re so worried that other people are going to judge us and make fun of us and talk about us and all this stuff.
But the hard truth is this: people are already talking about you, people already don’t like you. And people are already making fun of you. And I hate to say that, but it’s the truth. So, the reality is who are you living your life for? You or everybody else, you know?
So, I think that just really allowed me to sort of step in my power, step into my power, be authentically who I am and do things that make me come alive because that’s what this world needs more of—brave human beings who are out there doing things that bring them joy, because let me tell you, that is contagious.
Courtney: Yes, I could not agree more. And for those of you listening that can’t actually see what I’m doing right now, I am nodding my head vigorously in agreement with what Judi is saying. Because that is the whole truth, to live your life for yourself to not—just stop caring about what other people think, and to really just be proud of who you are at the end of the day.
So, thank you so much, Judi. It has been a true honor and privilege having you on today’s, the very first, episode of Dare to Interrupt, and thank you so much for sharing all of your wisdom and your secrets to success. I truly think that the people listening are going to be inspired and motivated and ready to get a little bit uncomfortable and try some of their own fear experiments.
Judi: Oh my gosh, that’s amazing. And if you want more of that juicy stuff, of course, you can learn more I’m sure we’ll link up everything in the show notes but, oh my gosh, hang out with me on Instagram. Come to my website, JudiHoller.com, all kinds of free resources there. You can learn more about me my work, my books, all that good stuff. We’ve got a podcast as well.
So, just would love to stay connected. And Courtney, what fun is this? Our first—I want to make a point here—this is the first episode of a brand-new podcast, and I want to remind everybody listening I think so many of us stop and don't do things because we're afraid that it's gonna—you know, of the unknown or oh my God, what if and I don’t have a script?
And what if it’s not perfect? And what are we doing? Courtney and I had no script today. We knew we were going to be two women who love this industry, who love you, the listener, women in this industry, men in this industry. And we knew we had some value we could provide to you and I think sometimes trusting ourselves enough to show up is all we need. It doesn’t have to be perfect. We must continue to fail forward. Because if we're not trying, we'll never know. And we all start at zero.
There’s always an episode one, Courtney, is what I’m trying to say. So, I’m proud to be you know, there's always a first date, a first kiss, first episode, the first blog post the first job, the first client, so I’m proud to be your first guest on this podcast. So hopefully, it’s well received by all the event bosses that’ll be listening in but just so cool to be jamming with you here and I’m cheering you on.
Courtney: Well, thank you so much, Judi. And thank you all for listening. And don’t forget to tune in to hear the next episode of Dare to Interrupt. See you all soon.
Want to hear more from Courtney Stanley? We thought so. Here you go.
Dare to Interrupt, Episode 1 Resources:
About our guest Judi Holler:
Judi Holler owns a creative company that is on a mission to help people live braver lives and EMPOWER leaders to lead braver teams. Her work takes the experimental principles of the improv theatre and helps you apply them to the unscripted stage of everyday life. Judi is a professionally trained improviser and alumni of Second City’s Conservatory in Chicago and she uses her training every day to smash self-doubt and experiment with fear. Judi’s book, Fear Is My Homeboy, became an instant bestseller on Amazon, is currently being translated into two languages and was endorsed by the inspiring Mel Robbins. Additionally, Judi is the creator of the Fear Boss Community, a community of brave humans dedicated to experimenting with fear, and she has a brand new podcast called, The #FearBoss Show which is now available wherever you listen to your favorite podcasts!