Hustle + Gather

Hosted ByDana Kadwell & Courtney Hopper

Sister entrepreneurs Dana Kadwell and Courtney Hopper talk about the ups and downs of the hustle, and the reward at the end of the journey. Life starts at the edge of our comfort zone, and that’s what running a business is about - it’s completely uncomfortable and yet thrilling at the same time. Hear Dana and Courtney talk about the hard parts of entrepreneurship with other business owners going through the struggle as well.

Build someone else’s dream or build your own, with Rachel Sheerin

Five years ago, Rachel Sheerin was crushing it in the hospitality industry. She built a team, was making a lot of money, and should have been happy. But she wasn’t. In fact, she resented the boss, the money, the team, and the laptops she threw on the floor.  All because she was building someone else’s dream and not her own.

Rachel Sheerin Hustle + Gather Podcast


Dana: Welcome to Hustle & Gather, a podcast about inspiring the everyday entrepreneur to take the leap. I’m Dana.

Courtney: And I’m Courtney.

Dana: And we’re two sisters who love business. On this show, we talk about the ups and downs of the hustle and the reward at the end of the journey.

Courtney: And we know all of the challenges that come with starting a business, between operating our wedding venue, doing speaking and consulting and starting our luxury wedding planning company. We wake up and hustle every day.

Dana: But we love what we do, and today we’re talking with Rachel Sheeran about taking the leap and knowing your angle. Rachel is a motivational speaker, burnout expert, executive trainer, Ted talk giver podcast, future author. She does so much we’re friends with her and we can’t even keep up with Rachel. Rachel welcome to Hustle & Gather.

Courtney: Yes. Welcome.

Rachel: Thank you so much, ladies. I feel like I’m running down the walkway on The Price is Right, right now being like “duh nuh duh nuh” and just high-fiving all my friends right now. It is an honor to be here, Bob. I am so pumped. I’ve seriously been looking forward to talking with y’all for forever.

Since you shared the idea of the podcast with me.

Courtney: Yeah, I think you were one of the first people we spoke to.

Dana: Yeah. We were like, we want to start it with Rachel. She’s the hype girl.

Rachel: Honored, honored. Well, in what y’all do talking about throughout this entire podcast series, I feel like it’s so needed, but also too one of those things where we only start talking about our journeys, , when someone’s in crisis, you know, and I don’t want to wait for a time where we’re in crisis to talk about the things where we talk about, uh, you know, entrepreneurship and dreams and goals and how that blends into your personal life. So I’m already a fan.

Dana: Thank you.

Courtney: All right. Well jumping right in. So, we know a little bit about your backstory, but everybody else doesn’t, but we know that you started working for yourself almost five years ago after being in the hospitality industry for eight years. And that’s a hard shift for a lot of people.

So how did you know that it was time? Like what’s the kind of two second version how’d, you know, it was time to go out on your own and do something different.

Rachel: Yeah, I think some of the early indicators were probably when I was crying on the way to work and then crying when I left work, that was probably an early one, another indicator might’ve been when I started to resent the giant team I had built and all the clients that paid us money.

Another indicator might’ve been when I threw a bunch of laptops and said F it I’m out.  Those were probably some early indicators but I got it. Oh, yeah. Yeah. All things point to “this maybe isn’t what makes your soul glow right now”. But I will say like, it felt like it was out of fricking left field because I loved what I did and I loved who I did it with and to go from one end of the spectrum, to the other, I always thought like, well, it’s because I’m tired. It’s because I’m stressed. It’s because of this, this and this. But there were a few things and I have to credit social media in a way. I remember one of the days I was getting really frustrated. And, I saw this Instagram post and it said that you’re going to be busy building somebody else’s dream, or you could be busy building your own.

And I remember I was crying per usual in that season of life, I was crying because I knew it was true, and I also didn’t have a dream. And that I think was for the first time, it really scared me because I just, I had always been an ideas person, a creative person, and yet, what do you do when your tank is totally empty? And, you know you don’t want to stay where you are.

So I think I did what I don’t advise. Most people that I talk to do, and I quit cold Turkey with no savings or net to catch me or anything like that. And I just said, I’m going to trust you. I said, I’m going to figure it out. And about six months later, the words I want to be a professional motivational speaker came out of my mouth and then in the next breath, I was like, damn it. I don’t want to do that. And I was embarrassed. I think it’s all the conjuring of motivational speakers and cheesiness and stuff like that. And also, to who would want to listen to me. And I also had a trope above, you know, a lot of speakers are white men who are very fluent and I am white.  But I’m not a man. And I, I, at the time was not as fluent as I thought I should have been.

Courtney: Now you’re a less affluent. You just quit your job.

Rachel: Yeah. Now I’m A- affluent with the lower-case a, but it’s one of those things where, I loved what I did and I wanted to get that love back and I just knew I couldn’t stay where I was.

Dana: So how did you figure out that speaking was your dream? That was the route you wanted to take.

Courtney: Yeah, like take us to those six months between F this I’m done with that. And by the way, now I’m going to be a motivational speaker.

Rachel: So y’all, I did everything in those six months between w first of all, I started going to therapy and to anybody who, you know I was raised Catholic and so when we have feelings, we just need to eat, or we need to sleep, or we need to pray about it. And some of those things worked for a while, but they didn’t always work. And I went to therapy. One of the things I want to say out loud is I went to therapy every week for $10 a week. And I went to a master’s, program of marriage and family therapy at a local college around me.

So, if you’re listening to this right now, and either you or someone in your life wants therapy and you want it in person, check and see if there are counseling programs or therapy programs around you, because they do a sliding scale. And so, $10 a week, I would go, I was doing everything to keep the lights on in my house. My husband had just started a new job and, I was the breadwinner in our family until I decided to quit.  So I was, you know, hosting yard sales. I was doing Uber. I was a photo shoot assistant for Belk’s department store. And here’s the thing – I like having a million jobs. I think I learn from them, it’s interesting. And as I started to do all these different jobs and try and get back to really focusing on myself, one of the things my therapist asked was, you know, what brings me joy and she defined joy as what you truly loved without influence of anyone around you, like without the reactions of anyone around you, it was just.

Right. It was just for me. And I mean, ladies, I know you all are parents. When’s the last time, the words “just for me” came up in your thought process, you know, typically not, especially in events and hospitality, where we’re thinking of the others, and we’re thinking of the team and the guests, and we’re thinking about the bogeys, you know, the people at like weddings or events that either shouldn’t be there, or we’re definitely overserved or whatever, but long story short is when I thought about joy, I was blank. I was like frighteningly blank for weeks. And I started to think about a band I loved growing up and the way the singer, yes, I liked the music, but it was what the singer said between songs that I loved. It was about believing in yourself and being yourself against the odds. And, there was a line in one of the songs I was resonated and it said, “reasons, not rules make you strong.” And I thought, yes, because I came from a world of rules and I was searching for all the reasons for these. Anyway, once I had that epiphany, then I said, you know, you immediately go into when, when something you really desire happens, you start at least I do. I start coming up with all the reasons why I can’t, Oh, I’m too old. I don’t have musical talent, like all this kind of stuff. But when I started to become very sad at that, I realized, no, no, no, this person’s a front person of a band, but they’re a motivational speaker on stage. And what I started to do was take the idea from what I had done. I started doing some sales consulting for women, creative businesses and in one of the exercises, isn’t it funny that we teach what we really need to know?

In one of the exercises, I have them draw a Venn diagram of three circles overlapping. In one circle are all the skills that you have, tangible skills, and this would be like marketable skills, like selling or training, team building. Then you have your dream circle, like your passion circle. This is like, I just, I love this. And you suspend all these ideas of what you think is marketable. Forget about it. I mean, the Kardashians make millions and billions of dollars a year. Anything is possible. Full-stop. And then you look at the third circle, which is how do you want the world to be different? And to me, one of the things that that allowed me to do was to look at, I loved always presenting. I love training. You know, every job I went to, I was inspiring people, making people laugh, helping people be confident and emboldened. I mean, you know, like these things were not by chance. They were by me. And I started to really own that. And then when I thought about the world I wanted, I was really angry for a long time at the owners of the catering company I’d left because what I thought and what I blamed him for a long time was he took something I loved and took it from me, that he didn’t support me enough that I could love it. And when I think back now, and this Venn diagram helped a lot. I didn’t want anyone to have to rely on someone else to save them from burnout, especially entrepreneurs that put their all into what they do. And that’s how I felt as an employee. I was in the executive leadership and I treated that business like my own

And here’s a real fact. That’s so hard for me even today to accept, but work will never love me, like I love work and I’m okay with it. Now I go in eyes wide open, but that’s how I made the leap.

Dana: There’s so many nuggets. I have like a whole page of things that are amazing, but I think what is so resounding in me. Is that what you said. Like what you truly love is you love it when those that who aren’t around you essentially like you, and I feel like in a world where we are so visual and our whole world is on display and there’s a lot of times you make decisions because you’re like, how is that going to look to the outside world?

How is that going to look on my Instagram feed on my Facebook feed or whatever, or, and you’re afraid to say, well, I’ve had this dream because you’re afraid of the critic that’s going to come after you. And so, you squash that love and you squash that dream and you squash it because you’re like, well, I just, maybe it isn’t real because everyone around me is going to judge me. That’s an amazing thing to realize and to come to.

Courtney: I think too, I really resonate with that as well. Like the therapy, what you truly love when you’re not influenced by others? And I think when you’re in such like a burnout and beat down state of just survival. It’s hard to even put words to that. I’ve been through lots of couples counseling. And I remember one time at a particular low point, the therapist asked, what would this relationship look like when you knew it was going well, right? Like when you knew that things were going the way that you wanted them to go. And I sat there and I stared at her and I was like, I have no idea.

Like literally, I have no idea. I’ve just been putting one foot in front of the other and I haven’t thought about what good looks like. I just thought about what now looks like and survival you get in that point of survival and you stop looking forward.

How did you deal with or get over like that imposter syndrome feeling like from going to being a catering professional, two, six months later, moving into, I’m going to be a motivational speaker? You have to really get over yourself to be able to do that. And what are some tips you want to give some of our listeners?

Rachel: Yeah, I would say one thing I did very early on was I culled my friend group and I kicked out a lot of folks. Here’s the thing, nobody turns into this podcast. It’s like, what should I do? Fire my friends! But I’m here to tell you right now, there’s so sane in the South – friends are there for a reason, a season or a lifetime. And I had to acknowledge that a lot of the people I would consider friends because all of my friends typically were through work, were there for a season. Or they were there for a reason. They were there for a reason because I had hired them and paid them to be there. That’s that hurts in a way, but that’s the real, I mean, that’s a real deal. I think the other side of it was I realized that to do really great things that scared me I couldn’t allow other people’s fear to be around me. For a long time, I didn’t tell my mom about my work.  Part of it was, it’s not because she’s not a wonderful person, so hi mom, if you’re listening, it wasn’t that it was that my mom has I’m the same work for 30 years. She she’s a loyal, steady person that does not take risks. She’s risk averse, and I am a risk enthusiast. And while she believed in me, her fears and nerves, weren’t helpful for me so early in a delicate journey, you know?

So, I, I looked around and I said, every single person that believes in me and that says nice things, isn’t doing it to stroke my ego. What if I really thought the compliments people gave me were the truth. And the second I thought, what if people say things because they’re true, not because they’re being nice, changed everything, because I think as women specifically, we’re taught to shrug off like, Oh, I love your jacket. Oh, it’s just from sale at target. Like no big deal. Why can’t we just take the damn compliment? Why can’t we just believe that people are going to say things because they need it. Why, especially in the events industry, especially in hospitality, especially in servant hearted leadership, do we think that every time we get a compliment, we need to then give something back to the other person.

Why are we coaching people? The fact is that if I don’t believe in myself, then why the hell would anyone else believe in me? If I don’t think I’m the expert, why should you? And I think that, that almost said, okay, well, what do I need to do to feel like the expert? And there’s a phrase that says, competence builds confidence.

I challenge everybody. If you don’t feel like you’re the expert in whatever you do, find a mentor, find education, go out and read the books, go to YouTube university. You don’t have to spend a dime, like really get information and build your confidence. And then on the other side is prove it with the sale, the first sale, the first keynote speech I was ever paid for, I got to speak at the Fairmont in San Jose, California. I rode in the middle seat, basic economy, last row of the airplane. I was so nervous. The stewardess, I’ll never forget her. Janet on American airlines. She gave me all these bottles of Woodford reserve, which is really nice, you know, because I was so nervous and I get very motion sick. So, I was feeling, you know, the back of the plane is not the place, but you know what I could pay for the ticket and I want to shout out Kevin Dennis from Silicon Valley NACE, he was the first person to ever pay me. He paid me $250 plus travel to get on that plane. And y’all the second I got that money was the second approved that I was, what I, what I’d always dreamed to be like what I was going after. And if someone would pay me two 50, that means that pay me 2,500, and that means that pay me 25,000 too. It was just a matter of when I got there.

Dana: That’s amazing. I feel that you kind of hit the nail on the head about it’s all about your environment too. It’s about what we decide to bring into our lives when we decided to believe about ourselves, is really what we emanate. I am a huge fan of culling friend groups. I am a chameleon, so I can be nice to everybody and anybody, but there are very few people who actually know me, like fully know my fears, my desires, and know truly who I am, because I don’t trust that with everybody. And I don’t trust my dreams. And my wants my desires with just a random…

Rachel: Not everybody deserves your story, your honesty.

Dana: That’s such great advice. Cause I feel like too, like my friends, they are the ones that are my hype people like my best friend from college. Like she sends me so much business. Cause she’s like, you’re the best wedding planner. I was like, I didn’t even plan your wedding. You don’t know anything about my business, but she’s like, but you’re doing it, so you’re amazing. And I see all, I see what you’re doing.

Rachel: And what she really means is you’re the best because Dana, if you became a realtor, you’d be the best. And that’s something that’s aimed you. That’s not something you do.

Dana: It’s so true. Going to therapy today.

Courtney:  Deep stuff.

Rachel: Yes. And you know, do you know when you talk about like the friend that encourages you? I think sometimes it’s tough because some people don’t understand what we do. Like everyone, like what does an actuary do? I have no clue, but, but they work hard, but it really is about the person you are while doing it. And what people feed, like entrepreneurship at its core, it can be a dream come true, or it can be a nightmare.

Or it can be both. I mean, really honestly, it’s both sometimes, but I don’t need other people’s nightmares coming in. I hang out with people who have dreams, and whether or not, you know, I have a friend of mine. They want to move to Costa Rica. They want to have a coffee, bean farm. They want to tell the government nothing. You know, like you go, you go and hoard all those coffee beans or do whatever you want to do. Like, I might not understand that fully, but I love that for them. It’s that kind of stuff that when I hear people undercutting their dreams, I think that’s one thing entrepreneurs are at risk at is am I going for something that’s too big?

And I think that’s the wrong question to ask. The real question you should be asking is, is what I’m going after, what I really want. And am I going to love the journey too? Because I think it’s possible to be blissfully challenged. This past year I’ve been blissfully challenged because I, at first thought I was hating everything, you know, being, uh, being at home, not having stages. I mean, so many cancellations y’all were in the same boat here, but then I started to realize I’m not here to be up on stage, I’m here to talk to people about burnout and loving their work and being massively successful. I could do that if I had a transistor radio. And so, this idea of like, are you going to be blissfully challenged? Are you going to look at the challenges that you have? I think that’s a big. I didn’t realize when I started my business, but that has really made a lot of the difference in how much fun I’m having along the way.

Courtney: I just had this image of you and like some post-apocalyptic world where you’re on some transistor radio. Like, do you have your hacksaw ready for today? You’ve got this! Zombies are coming, but you are prepared! It is in you!

Rachel: Totally. If anyone out there is currently scripting for a comedic spoof on The Walking Dead, I am happy to be that. Yes. I’m dramatic and I’m creative and I live in a fantasy world occasionally for creativity.

And I do think about like, God, if, if the odds were so stacked against us, like who would I be? And it, it reminds me of a phrase my mom used to say about people who won the lottery. She would say that money doesn’t change you. It just enhances what’s already there. And I think that’s one of the things about entrepreneurship that it applies to. Because entrepreneurship feels like Mad Max mixed with Jurassic Park mixed with like the Wolf of Wall Street mixed with the Titanic. You’re like falling in love, and then all of a sudden, out of nowhere, there’s a damn iceberg that you didn’t even like that wasn’t even your responsibility, but now you’ve got to deal with it. You know?

Courtney: You were just standing on the bow of the ship, like live up in life with your arms open, not two hours earlier.

Rachel: I was the queen of the world. I know. It’s ridiculous. It is. It’s fun. It’s, it’s mostly a dream and it’s sometimes a nightmare.

Dana: Yeah.  I really resonate that a lot, but for me, I am such a goal-oriented person.  I, for the longest time I made one-year plans, five-year plans, 10-year plans, and I quit doing that. Cause it would just frustrate the hell out of me cause I never. It never happened, but I think one of the biggest things I hear people talk about entrepreneurship is the fear of like, they have a goal in mind, either never getting to it or it changing so drastically. And for me, I feel like I’ve always had an end goal. Like my end goal is to stop planning weddings and just be a support system. I want to hop in on some fun ones. I want to give some feedback, I want to like, just be in that, that role and same thing with like the Bradford. Like, I would love to just be a manager, a high-end manager. I don’t have to talk to you every single day.

Courtney: She’s saying like COO.

Dana: Yeah. So, like, but that end goal was supposed to be 2020, right? That was supposed to be it. And, I mean, I think it was the middle of the year – we’re still taking out the trash, but maybe this isn’t what our end goal is. Like, maybe that has to change, like maybe it’s different now based on you know, where we are, but I don’t know. I feel like that’s one of the things I hear a lot of people talk about with entrepreneurship is it’s like this ever-moving target, like where you’re just like, okay, I’m just going to shoot here, shoot here, shoot here. And then maybe something will stick.

But did you feel like when you stopped working, he had that six months, you’re like, I’m going to be this, what was your end goal dream? And is that very different from where you are right now?

Rachel: You know, this sounds trite, but it’s the truth. My goal was to be happy. It had been such a long time since I had been really happy without anything in my day that I wasn’t dreading the thing is, and, and I would challenge you, and Dana, I think that’s where you are, and Courtney, you were last year as well. Is this idea of yes – The goals matter. Cause I love goal setting. I love crushing goals. I mean, y’all, you know, I’m getting that private jet. Like this is not if it’s when, but when it comes to goals like yes, set the goals for sure, but also too, set a serious goal and intention for who you’re going to be on the way to getting there, because that, to me, it sets you up for success, no matter how you slice it, because here’s the thing, the person you are taking out, the trash is still the person you are as COO.

Like you still are somebody who will do anything for your team. You’ll. You’re somebody who is profit focused because it’s important. And it’s part of your goals, but also to, you’re a humble leader, you’re a servant leader. You’re somebody who shows up these kinds of things. You know, that’s why to me, I set goals in four ways.

I say what’s my personal goal, my professional goal, my health goal, and my relationship goals, because y’all some years, some years professionally is going to suck. I’ve friends in the speaker world that are multimillion dollar a year folks, and they’ve thought 2020 was the worst year that’s ever happened to them.

And to be quite honest, they missed the part where they were, you know, spend more time with their family. Which I loved, personally, last year was one of the best years professionally. It wasn’t so about either, you know, and I’m, I’m thankful for that. Health wise, it was my best healthier of all time. And you know why?

When I set four goals, when I have four ways that I can measure success, if I get 80% of the way to two, and fail at the other two. Great. That’s a win.

Dana: Well, what was your biggest, would you say your biggest like, Oh, shit moment.

Courtney: Like in the speaking career?

Dana: Yeah., in your career, and you were just like, I don’t know if I’m actually cut out for this and you kind of hit that really low and you had to pull yourself out of it.

Rachel: One of the speeches that I was giving, I am from the Northeast, and so I say, hey guys, I’ve been working on saying, Hey, y’all a lot more to be more inclusive. And I was giving a presentation to a major university and I said, Hey guys. And I remember the coordinator called me from the university afterwards.

She was like, we loved it all.  But. Your language was not inclusive. Like just as a heads up, you said, hey guys, and I will tell you working with young adults and education and booking through my agent on the education market has been a real eye-opener for those kinds of things and the idea of micro aggressions and what I was speaking on.

And being anti-racist is definitely. At the top of my mind being inclusionary, getting more women, persons of colors on stage have always been a core driver for me, but y’all when she said, hey, you know, and, and I think there’s a chance that if it made people feel singled out or in a uninclusive that got me, it was, I think in September, October of 2020, it got me on such a deep level because I had betrayed who I was.

If you meet me, you see me, right. You all know me that that’s – I am an inclusive person. You can tell me anything and I will accept you and, and be curious about you and support you. But to know that I had done something that had been the exact opposite of what I was there to do, instead of motivate I alienated, instead of included, I excluded like th those kinds of things that I, I had a serious, long cry, and I thought, am I the person to carry the weight?

Like, am I somebody that should be listened to if I could be so flippant, so careless? I understand what happened. The client was totally fine. Like it’s not about that. It’s about looking at myself and saying, am I worthy and seriousness serious enough about the gravitas that I have? I was the first time, I think in a long time I had realized how much, what I said was getting listened to.

And I took my influence. I think even more seriously. When I think about the person that I am and the legacy I’d like to leave behind, it made me really stop and reassess, not just what I was saying, but what I was thinking, what I was reading what’s on my website, the way I speak on social media, because I thought if I could, so casually have said one thing that I was aware of, but to be honest, if you’d asked me before that speech, if you throw a Hey guys in there, is it a big deal? I would have said no. But it’s because I’m not listening to myself with the gravitas that other people are. And, and that’s really an honor, I think when you’re an entrepreneur at least that I get along with the most are people who really take seriously and love and take with pride, the impact they have, not just on themselves, you know, but their team, their clients, the world.

And I, I think if we were all mindful about that, just a little bit more of the world might be a little different.

Dana: We just actually had evolve last weekend and they talked a lot about inclusion and whatnot. And, I think the one thing she said, like, you can’t be afraid to make mistakes, but stay persistent.

And that really spoke a lot to me because I’m terrified of making mistakes because very much like you, I know my heart and like, I want to be inclusionary. I don’t want to offend anybody. I don’t wanna upset anyone. I don’t want anyone to think… And part of it is truthfully. I don’t even think negatively of me.

I don’t want them to have this opinion because living in the South, you are automatically characterized as one way just off the bat. And it’s terrifying. Yeah, I’m so afraid. Like every single post I make, every single thing I’m like editing it, making sure I’m hitting all these markers, but I feel like a lot of times too, is it silences me more because I’m too afraid of offending everybody, as opposed to just saying like my truth in a way that I know my heart is pure and true, that makes sense. But that’s intense. I mean, I think that’s an intense thing to go through and to question who you are based on a hey guys, it’s something that I think is amazing. I think we all should reflect our own speech in that way and like, How’d that same way with how we talk to people.

Courtney: But I think with great influence comes great responsibility, and I think as your influence grows, so does your responsibility to those that you are influencing, and it sounds like, kind of like one of those moments, like, Oh, okay, let me realize that. Well, this isn’t my intention, this isn’t how I meant to sound. This is how it came across as somebody else that you’re trying to influence in a positive way.

And you don’t want your message to be lost by just some colloquialism from Pittsburgh or Pennsylvania, because we’re the same way. I’m like a guys, everything’s Coke to me, even if it’s Pepsi, you know, like those kinds of things, like it doesn’t mean anything. It’s just how I learned growing up.

Rachel: To that point, it’s like, I think entrepreneurs to everyone listening out there. I think the fact is is that you don’t have to be in my line of work to have influence. You don’t have to be leader in the title to be a leader. You don’t have to think yourself worthy of following to have people that follow you. I mean, parents – parenting seems like one of the hardest things ever. And while they’re adorable and smelly and wild and all, all other kinds of things, what they really are for a long time are carbon copies of you and what you say and what you think and I think that’s one of the, I think, both cool, and to your point Courtney, it’s both a very heavy responsibility and also a very exciting one. The idea that, like, how would you present yourself differently? How would you speak differently if you knew people would emulate you? And to me, I think that’s where we speak with kindness and love and encouragement and empowerment.

You know, I don’t think that people wake up in the morning being like, I can’t wait to dash someone’s dreams today. Be super rude to them, scar them for life, you know? No, nobody does that, but that happens through microaggressions and passive aggressiveness and sometimes straight-out aggressiveness.

Dana: But what I, what I love, and I think this is a great, just takeaway point is you have to be okay to make the mistake and let someone come back and tell you that maybe you messed up because that’s the only way you’re going to grow is to own the way you’re going to learn. And at the end of the day, I say this all the time to my people, my employees, they’re going to know your heart, like your actions, your words, how you treat people, they’re going to know who you are more than what you say. And if what you say is not right, don’t be afraid when someone says, Hey, like that offended me for you to say, I’m so sorry. How should I have said that? I, for the longest time, I didn’t know is it appropriate to say African-American is appropriate to say Black? Now I’d ask a friend of mine. I was like, what is it? What’s right. Like, I don’t, I don’t want to say the wrong thing. And I was felt like I was just, not being appropriate in the conversations I was having and being open to having that dialogue with somebody and having that feedback.

Rachel: Curiosity. For sure. My dad, he used to say, an important phrase for me. It’s aren’t you glad you found out now and that after like some serious reflection on it, I thought like, yeah, I am glad I found out now because, you know, 3000 people is a very large stage to me, but 30,000 people we’ll be in my future, and I’m so glad to be more aware of that. You know, I will say quickly, the other thing that was pretty brutal was I almost, I almost went down in a plane crash on the way to my first national convention I ever spoke at. That was the other thing I did think on, but that may be is for another episode.

Courtney: Oh my gosh, you leave us on a cliffhanger.

Rachel: Yeah, that, that was a real moment. That was great. I arrived too in the conference. Didn’t have any AV for me. It was, Kismet, it was great. And you know what? That was one of the scariest days of my life.

And I will say out loud, it was by far one of the best because it, it really solidified that I loved what I was doing. And I think, to end this episode, I would say, remember the days where you love what you were doing, what was it about it? Was it the clients who were working with, was it the, actually what you were doing? Was it the season? Was it the place? Was it the, you know, the relationships you had in your life at the time? Was it this combination of everything either is my goal every single day to have not the best day ever, but to have my dream life and the life I’m living be the exact same life.

And I used to think it was going to be in some like mansion or something like that. Heck no I’m saving pennies for, yeah. All right. I’ll live in a brick ranch house all over the world, but it’s this kind of idea of what is around you as you do it, that’s going to be, if, you know, getting some feedback and having me really reassess was one of the more challenging ones.

I think almost dying was another one and it just made me solidify like, yep, that’s what I’m doing. And I’m so glad that I did it before I didn’t have any time left.

Dana: It has been so wonderful talking to you. I feel like you always just, I have like just pages of like nuggets, just to think on and so much inspiration and just really tangible ways to think about like your life.

Rachel: I will just like to say that if you enjoyed this episode, this is what, you know, making sure your friend circle is supportive and looks like, this is how I walk away from speaking with you, both thinking about so much. And we pull so much from each other. I think that’s where, it is that like, I think about like people who climb cliffs, which is definitely not me, but I always think about like the person that like grips onto your wrist and pulls you up. It’s like, there’s that security, but the person who’s getting pulled up is really doing most of the work there, but that’s what great friendships are like. And I’m really grateful. I think that’s what we have.

Courtney: Thanks everyone for gathering with us today to talk about the hustle. To check out Rachel, visit Listen to her podcast, F this S or follow her on Instagram at rachel.sheeran

Dana: And to learn more about our hustles, visit or or follow us on Instagram at canddvents and at hustleandgather. And if you like the show, be sure to subscribe and leave us a rating and a review.

Courtney: This podcast is a production of Earfluence. I’m Courtney.

Dana: And I’m Dana.

Courtney: And we’ll talk with you next time on hustle and gather.

Full Episode Transcript

Rachel Sheerin is a motivational speaker, burnout expert, Ted Talker, future author, podcaster (go listen to F This S, it’s amazing), and all around badass.

If you’re drinking along with us today, that means you have a Jalapeño Mezcal Margarita!
Hustle and Gather is hosted by Courtney Hopper and Dana Kadwell, and is produced by Earfluence.  Courtney and Dana’s hustles include C&D Events, Hustle and Gather, and The Bradford Wedding Venue.

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