Building a Successful Website

52: Being the Most Confident Woman in Any Room with Jen Brown

Public speaking, whether you’re in front of one or 1000, can be insanely intimidating. Throw in the need to have an impromptu conversation — or maybe you’re an introvert — and watch how quickly your once confident mindset can run for the nearest exit.

Today we’re talking about being the most confident woman in the room, and I have an amazing, amazing guest, Jen Brown, to help me out with that. So Jen is an accidental entrepreneur, which is insane in its own. After recognizing the need for her co-workers at the Guggenheim Museum in New York City to spice up their educational tours, she started her company The Engaging Educator as a side hustle while working off Broadway. But The Engaging Educator quickly became a full-time gig.

She’s worked with — be ready for it — over 50,000 students, including the Food Network, New York Times, Saks Fifth Avenue, Uber, and CBS (just to name a few). And not to mention she’s given several Ted talks. She and her team are all about empowering women to find their best, most unapologetic and confident voice, which is why she couldn’t be a more perfect guest.

Jen, welcome to The Gutsy Podcast.

accidental entrepreneur

Laura: So you’ve done some phenomenal things in your career. I was looking at your website and researching your your social media accounts and you’ve just done some incredible things. I’m excited to have a conversation with you today with our guests.

So talk to me about becoming an accidental entrepreneur because I feel like entrepreneurism is typically one of those things you’re seeking, but this kind of fell into your lap. So take me on that journey,

Jen: I like to say that I’m an accidental entrepreneur and I really do believe it. Like people will say, Oh, don’t like downgrade your self. And when I was just thinking it was gonna be a side hustle, this idea of teaching improv to museum educators, to colleagues, to friends, I was like, I’ll just do this and then I’ll work full-time at a museum. Totally cool.

And this is after I quit acting. This is when I went back to school to get my degree in art history. So I was like on a path that I thought was my path. And after I think it was like way too many 2 a.m. e mails that I was sending for my quote-unquote business or side hustle at the time that I was like, I can’t do those. I can’t keep worrying about people checking the time stamp on email and either thinking I’m crazy or me just not sleeping enough. So I have to actually do it or don’t.

And I ended up just doing it. So I love it. I’m learning every day, but I think I’m like a poster child of you don’t need to go to business school. Like we know that, but I think in our heads were like I don’t know anything about business. I can’t business. It’s like no, no, no. You can learn it all. You can pick it up and everyone is gonna screw up. You included.

Laura: 100%. I often compare entrepreneurialism to parenting because you could read every book, you could go to every class, and you’re still gonna flub up something. And then you’re gonna nail something else. In every step, every part of the journey, you’re learning something new.

from side hustle to full-time gig

Laura: I think you hit on something that a lot of people in the beginning stages of their entrepreneurial journey experience, that you were sending like a bazillion emails at 2 a.m. And you are at that fork in the road where you have to decide to take it all or not. So what was kind of your deciding factor on quitting your full-time job and transferring into The Engaging Educator full-time?

Jen: Well, it’s interesting because that journey was weird as well. I was pulling both off poorly for a while. And then I was on a business trip down to North Carolina and I really fell in love with the state. Which is weird after living in Brooklyn being like, Oh, North Carolina’s amazing.

So I’m double-dipping in New York. I’m in North Carolina. I’m in love with the state. And on my very last stop I meet this is Dude and I’m like, Oh, man, like I like this state. I like this guy. We’ll see what happens. And then I was sitting at a Latin diner that I absolutely love in New York that I still go to every single time I’m back, and it was like a late March snow storm, and it just broke me.

I was like, I can’t do this anymore. I can’t deal with late March snow. I can’t deal with schlepping. I’m so tired. I’m not dedicating any time to my business. I’m still dating this guy long distance. So maybe I’ll move to North Carolina. And not for him, I’m gonna get my own place, which I did, and I’m just gonna do EE full-time because I couldn’t afford to do that living in New York. It wasn’t a possibility, unless I don’t know, many, many things changed.

So when I moved down to NC, I got a townhouse, was super excited, cost of living is so much better, and then I started looking for a job and I’m like, What are you doing? You’re spending all this time looking for a job because you’re scared. The amount of time I spent looking for a job because I was too scared to do my business full-time, if I would have applied that to do my business full-time — I would be able to live off my business full-time.

That moment of realizing that I was just trying to pick something else up, like one of the reasons for me leaving was to do this still, And when I stopped looking for a job and stopped being ridiculous — cause that’s what it was, me being ridiculous — and put that amount of time into my work, I was able to be like, Oh, this is something that can sustain me full-time. And I can still have people working in New York teaching classes and I can still grow my brand and I don’t have to get a job.


Laura: So confidence is something we all have, but it often gets masked by other things. Fear, worry, concern, opinions. So you’re working with women to find their confidence and really resonate with that. Talk to me a little bit about some of the first steps that you take, about your business, and how you’re working with these amazing women?

Jen: Absolutely. So I think the biggest thing when I talk about this is this idea that confidence looks different on every single person. That confidence for me is gonna look very different than confidence for you, than confidence for one of our students, from one of our teachers. Because we’re all different people. There are some things that everyone may do that looks kind of similar when they feel confident, but when it comes down to it we all express it in very different ways.

A lot of times how we’re feeling about ourselves and our own self-confidence comes out in our communication. So if we’re constantly apologizing, if we’re not being assertive, if we’re going through our head and going Man, I wish I would have said that in that meeting, or I could have sent this or I should have done that. And that’s really what we’re helping people with in the end, being able to express their own brands of confidence through their communications style.

So we’re tapping into that with improv, which to some people is terrifying. It’s like one of those trigger words. I tell people like don’t tell them it’s improv. Just just tell them it’s communication skills or tell them it’s practice or public speaking (which is scary in a different way). But I think that what it does with improv it’s like you’re tapping into reality.

So you’re able to go into those situations where you wanted to say something in a meeting, you wanted to speak up for yourself or someone else. You can do that in an improv conversation and try it on for size in a very safe environment. So that’s really how we’re tapping into that. And it’s just amazing to watch some people and women grow through classes and really come back to us.

It doesn’t happen immediately, but they come back in a couple weeks, a couple months, and they’re like, Hey, remember this? Like this happened and it’s amazing. And I’m like, Oh, my heart is so warm right now. Please tell me more.

don’t feed the birds

Laura: Yeah, confidence is like a muscle. You don’t just go to the gym once and all of a sudden you have a six-pack. You have to go time and time and time again to really build that. I feel like confidence is the same way.

So talk to me about one of the very first steps. Because if you’re shy or timid or you feel like my voice doesn’t matter, that’s a huge thing for women. What are some common things that you see in women and why we’re not expressing ourselves in the get-go?

Jen: I think we have a lot of opinions on how we should be seen and how we want to be seen by other people. And I think one of the first things I ask everyone to do is just tap into that. What does confidence look like on you? Is it being happy? Is it being able to speak your mind? Is it being able to speak up? Is it just saying something? Is it taking up space with your body? Like, what does that look like when you feel confident?

When you identify that, then start going, Okay, well, what makes me feel this way? Is it when you nail a sales goal? Is it when you really talk to a client in a way that feels really connected with that client? Is it when you get on Instagram Live and talk about your business or talk about what you’re doing? Really identify it and be really specific with what that’s making you confident now.

And if it’s a tiny little thing like, you know what, I feel super confident when I’m wearing a really good outfit. Great. You tap into that.

On the flip side, what makes you feel not confident? What makes you start to feel nervous and feel like you’re not being the best version of yourself? Don’t attack everything at once, but what are some shifts you can do in your body, in your voice, in your communication that gets you more towards that confident version of yourself? A little step by step.

So when you’re wearing a great outfit. A client recently told me, “I feel super because when I wear a great outfit, I feel confident.” I’m like, “That’s awesome. What does your body do when you’re feeling that?” And she’s like, “Well, I know my shoulders are better. I’m not slouched. I’m walking with some urgency behind my pace.” I’m like, “Cool. When you start to feel not confident, start doing some of those body emotions. Start positioning yourself in that way. Or when you know you’ve got something that’s making you nervous, wear that bomb outfit.”

I think women don’t necessarily always tap into it because we’re so worried about people saying, Oh, she’s bragging or oh, she’s not humble or oh, she’s being too assertive or too direct. And it’s like someone is always going to dislike you, no matter what you do,

Laura: You lead exactly into my next question. I think oftentimes confidence is mistaken with arrogance or the infamous Oh, she thinks she’s all that what a bitch. So how do you help women over come and balance?

Jen: Someone’s gonna think you’re arrogant no matter what. Someone’s gonna think you’re not enough. Someone’s gonna think you’re too much. It becomes like, really, what does their opinion matter? And why are you letting that affect you so much? Because the thing is, if you’re gonna be too much for someone and if you’re gonna be not enough for someone else, when do you say enough is enough and you’re enough for yourself?

One of my friends always tells me “There’s always gonna be birds.” There’s always gonna be people chirping and not contributing and just being there and being loud and noisy. It’s up to you if you feed the birds and they stay or if you just don’t feed the birds and they go somewhere else.”

Laura: Don’t feed the birds. You don’t get a snack. You don’t get bread crumbs. You don’t get bird seed. You could spend your entire life catering to the people that think you’re too much. So you’re dimming your light into the people that don’t think you’re enough, trying to over exert yourself, and then you end up just kind of in this gray area of your life where you just don’t feel like you’ve moved the needle. You don’t feel accomplished. And it’s exhausting. Like every person was born with some talent or gift that the world needs, and all of that is just noise to get you away from that.

focus on the right people

Laura: When you’re worried about people that are thinking this way of you and then the other people that are thinking completely offset, like you said, why does it matter? Why is that a driving force and how have we gotten so far away from being centralized within ourselves and what we want in the first place?

Jen: If you’re thinking in your head I want to be liked, I want to be accepted. Well, what kind of people do you want liking you? This is a very real want for some people, they want to be cared about.

I did this adventure partner with an organization out in San Francisco. So I help other entrepreneurs basically find community and it’s such a cool mission to focus on finding people that you can talk to and connect with. But one of the sessions we went to when I was in training for this is don’t focus on the people that are meh with you. Focus on the people that like or love you. Cultivate that because trying to convince someone that doesn’t like you or someone that’s kind of like whatever, that is such a hard task. And it’s probably not gonna work out.

But if you focus on the people that already like you and the people that already love you and just build there and them and what they’re wanting from you as an entrepreneur, you’re gonna get such a better payback. Because those people already like you and you don’t have to contort yourself in all these weird positions to be the person they want you to be.

Laura: It’s so true and like-minded grows like-minded. So when you’re in a space doing what you’re called to do, you’re just shining in your area of awesome with people that are already supporting you. Then that tribe can grow. That encouragement can grow. That support can grow. And I think eventually that meh shit just kind of falls off the edge, right?

Like darkness can’t out stand light. I think the important thing to remember is sometimes that stuff gets louder right before you really break through something. So if you’re getting pushed back and you’re getting a lot of, like you mentioned earlier, the chirping of the birds, you have to really just stay hyper-focused on what you’re working towards, why you’re doing it in the first place, and who you’re doing it with because eventually it’s just gonna fall off. It can’t withstand it.

track your days

Laura: Some of the courses and things you’re teaching women, how do you use some of those tactics to overcome those moments where you want to quit? Because I think that’s one of the highest pressure areas of running a business.

Jen: Always have those reflective moments of, Okay, I feel this way. Why do I feel this way? What’s going on? And most of the time it’s not because I should quit, I’m terrible, I don’t know what I’m doing, or I’m just messing everything up — which is how I feel in the moment. It’s because I haven’t slept or I haven’t eaten well or I haven’t been taking my vitamins or sitting in front of my happy light or any of that stuff.

We tell people when you’re thinking about confidence and you’re thinking about communication, especially, to really narrow it down to four things: 1. Who you are and what’s your relationship to the people you’re talking to. 2. Where you are both in life and physically. 3. What you want. 4. How you feel.

And we think with business sometimes that we don’t have to pay attention to those feelings, but they’re super important — especially when you’re feeling super high or super low. Because if you’re feeling super high, you might need to be like, Okay, how can I remember this? How can I take this back when I’m feeling really low again? And then if you’re feeling super low, it’s like, Okay, well, what else is going on? What’s going on in my relationship? What’s going on with what I want? Am I standing in my own way? Am I doing the same thing expecting a different result?

It’s okay if you don’t reflect in the moment, but like I have a little journal that I write down or a color code each day, how it was. Because I’m also like on the high side of getting out of severe depression, so it’s been like remission, and then I think I’m officially out, but are you ever really out is one of those questions that I ask. So I tracked my days and log my days, and if I noticed that I’ve had a lot of tired days in a row and suddenly I’m super anxious, it’s not the stuff that happened that day that made me anxious. It’s the three days of no sleep leading up to that day that has made me anxious.

So I tell people to do the same thing. Take the big step back and look at your life much like a coach would. And don’t just get lost amongst the trees. Take the 40,000 square foot look on what actually is going on. And then you can see things a lot clearer if you start reflecting.

the power in pausing

Laura: Sometimes you just have to, like, pause. So how do you pause?

Jen: When I pause, I close my computer. I put away my phone. I pull out a book. Like I recently got my hobbies back, which has been been life-changing and game-changing. I pull out a mystery thriller, and I take time with that. I’ll make some food because I actually really enjoy cooking now that my kitchen isn’t the size of a postage. I have a lot of plants, so I really like taking care my plants, checking them out, and looking at new plants.

I’ve made so many poor decisions without pausing that I’m like no, no, any decision I make or any work I do right now is going to be trash. So I have to pause in order to do the work I’m doing again.

Laura: I love it. It’s kind of getting back to the why because if you can’t have hobbies, if you can’t have just complete solitude and downtime, if you can’t exercise, if you can’t cook, then why are we doing this to begin with?

Jen: Exactly. And when people say, Oh, I’m an entrepreneur because I have more freedom [laughter] I’m like Uh-huh, sure. But it’s and take. So I’m 37 now, and I see people in their early twenties and I watch them and I’m like, I know where you’re at. And I know you think you need to burnout in order to get this done. Just learn the Banksy quote: Learn to rest, not to quit.

It’s so important because we think we have to push ourselves so hard because we’re gonna lose this client, we’re not gonna be able to do it. And it’s like you don’t do good work. You’re not the best version of yourself if you’re pushing yourself to a limit where you’re not showing up for people.

I was coaching a woman last night and she was chatting with me about how she has to network with like 30 to 40 people every single event she has. But by the end, she’s not listening to people. And I said, “Well, why is it 30 to 40? Like, why does that matter?” And she’s like “Well that’s what I have to do.” I was like, “Okay, cool, but if you do 20 that are quality and 10 that are garbage, why does that 10 matter?” And she was like, “I never thought of it that way.”

You have to consider when you push yourself too far, you’re not doing good work.

know your limits

Laura: I think that when we’re talking about confidence also is when you are exerting yourself and when you’re not taking care of yourself or you’re pushing yourself to one limit or the next, it’s hard to feel confident when you’re stretched. I know preparing for a meeting, for instance, if I’m rushed, if I don’t have everything that I need, if I’m not really taking the time for myself to plan and get prepared for that meeting, I don’t feel confident. So I think a lot of it comes down to having the space and capacity be able to do the thing you came here to do in the first place.

Jen: And if you think about confidence, you feel confident when you’re feeling the best version of yourself. You’re not feeling the best version of yourself if you’re burnt out before a meeting and you’re rushing to get everything together and then you beat yourself up because you’re like Oh, I screwed that up and now what do I do?

It wasn’t because you’re not capable. It was because you didn’t sleep or because you didn’t think you needed to take care of yourself. And I think we all know our limits. And again, we’re gonna have to push ourselves sometimes.

I was a horrible person to be around when I was writing my book — awful — just like catastrophically awful. And I was talking to someone else and she was like, “Well, what would have changed? How could you have made that better?” And I’m like, “I don’t know, not write a book?” [laughter] It’s a stressful situation at the time. I made sure, though, that I wasn’t traveling a lot while I was doing it. I knew that I could control certain elements and how much stress I was putting on myself. And I’m like, I can’t do more than X, like I have to stop at some point.

Laura: I think that that’s a really important takeaway is knowing your limits. It’s really hard to be confident when you’re just kind of half-assing everything just to get it done. And at the end of the day, you sit at home and you’re like, Well, I did a lot today. But don’t really feel like I accomplished anything. Still have a laundry list and I don’t feel awesome. So another day in the books.

That kind of mentality will weigh you down so quickly.

implementing your true confidence

Laura: So I feel like a lot of the quote-unquote lack of confidence comes from the things that are happening inside of our heads. So we absorb a lot of information. we see lots of things, we internalize it, it goes into this bank of I’m going to over-analyze everything, and then what comes out is a diluted version of ourselves because we’ve got so caught up in our heads.

What are some recommendations that you have about getting out of your head and actually implementing your true confidence?

Jen: I think again it goes back to knowing what that true confidence is and identifying when it is not coming out. How do you want people to see you? How do you see yourself?

A lot of times when you’re stuck in your head, I think it’s really smart if you’re a written person or a verbal person, like word vomit that out. Write it out, talk out, record it, re-read it. Listen to it. Because then when you see it, when it’s not just existing in this like tornado that is our thoughts, you start to realize That’s kind of ridiculous right now. I really don’t care about that. Why am I overthinking?

Laura: It’s a really solid reminder to give yourself space to really feel yourself because it gets, again, diluted. There are so many things happening around us. We’re running a business. We’re running a family. We’re a leader here. We’re doing this. And we as humans just end up unintentionally getting diluted.

So I think one of the things I’m taking away most from our conversation today is just really allowing yourself a space to get back to who you are. Talk to yourself, feel your emotions, ask yourself what you want. Why am I doing this? Why do I want to pursue this? Why is this calling me?

Just really giving yourself a chance to be you again.

What Does Gutsy Mean to You?

Jen: Gutsy means going for it. And it really ties into my favorite quote of all times: Do it now or forever wish you had.

connect with jen

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