How Curiosity Can Give Us Confidence with Female Yacht Captain Kelly Gordon

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This is a podcast episode titled, How Curiosity Can Give Us Confidence with Female Yacht Captain Kelly Gordon . The summary for this episode is: What happens when we allow ourselves to be curious? We challenge our current way of thinking and learn more about ourselves. Our curiosity drives us to step out into something we’ve never done before and just figure it out. It’s this act of figuring it out that gives us confidence. Once we start to evoke that sense of confidence in ourselves, others start to have more confidence in us. In this week’s episode, we will listen to Kelly Gordon — the captain of a 75-foot motor yacht — as she tells us the story of how she followed her curiosity and had the sheer confidence to just “figure it out.” In her conversation with Rebecca, Kelly talks about her journey of becoming one of the few female captains in the boating industry, and her success in maneuvering a yacht with a female crew. She shares her deep desire to learn, and how she had the confidence to try something new. Listen in to learn more about how Kelly had the confidence to follow her own curiosity, and the importance of searching and exploring throughout your career.
Introduction to Kelly Gordon
01:21 MIN
Curiosity can help us gain the confidence we need
00:45 MIN
We carry our experience and lessons we have learned to each place we go
00:22 MIN
Our careers are a part of our human stories
00:29 MIN
We can be more successful if we pursue careers that interest us
00:54 MIN
We can build our confidence by allowing ourselves to just "figure it out"
00:38 MIN
We can use our gifts and talents in a lot of different ways
01:06 MIN
How we talk to ourselves is the first conversation we have about anything
01:58 MIN
The best place to learn is when we are feeling uncomfortable
00:53 MIN
We have to have a strong community of support to encourage us
00:46 MIN
We are emotional and social and we bring our personal lives to work
01:14 MIN
We are not machines there to produce; we are humans there to add value and impact
01:11 MIN

Rebecca Fleetwood Hession: This is Rebecca Fleetwood Hession, host of the Badass Womens Council podcast. And I am super glad that you're here. Okay. I'm going to start with a reflection question for today. What if we stopped searching and started exploring? What if we stopped searching thinking that somebody or somewhere out there was the answer to our lives' questions, and instead, started exploring from the depths of our own heart, mind, soul, interests, curiosity? And we've talked about this on the podcast before, this idea of letting curiosity be a key aspect of your career. And today I couldn't be more excited to share this interview with you with Kelly Gordon, who exemplifies this in just big, bold, beautiful ways. And just to give you a little preview, so Kelly quit school in the ninth grade, went on to get her master's degree in chemistry as you do, and today is the captain of a 75- foot motor yacht, which is a corporate boat in Chicago. Her and her first mate, Giana, have recently made two trips from Florida to Chicago through the river systems. Now, let me just pause for a minute on that. We're talking a tedious trip that takes guts and skill. And they've done it, not just once, but twice. Twice because the word spread after they had done it the first time, that they had done this with such skill and such precision, not to damage the boat, that they were asked to do it again. And I believe that that's the example that I want this episode to set that: When we're curious and go out and do things and figure it out, it's that act of figuring it out that gives us confidence. And the more that we try things, and the more that we figure it out, the more confident we are in ourselves. And the more confident we are in ourselves, we then evoke that sense of confidence so that others can be more confident in us. But it starts with act of curiosity to jump out there and just try it. And I know this interview is going to inspire you. I don't even know if we've got time to tell all the things that you've done. But you grew up North of Indianapolis in a tiny town, and your life has had a really interesting, just what I call kind of that breadcrumb trail of discovery. You've tried a lot of things and done a lot of things, and just been curious enough to follow your interests around. Just give us a snapshot of your story.

Kelly Gordon: I think it seems like growing up as kids, it's almost kind of like you're raised to, you go to school, you graduate, you go to college, you get a job and that's it. And there's me and my sister and we have a little brother, and us three were raised by a mom that you can do anything you want to do, be anything you want to be. And when I was little, I remember one minute I said I wanted to be an astronaut, and my mom said, " Well, that's fine, but you're going to have to figure out how to get past your inaudible sickness issues." And I was like, " Okay, well I will." And then the next minute I wanted to be a firefighter, and the next minute I wanted to be the trash truck driver. So we were all three fortunate to have a mom that said, " You can be or do whatever you want to do," and fostered that curiosity. And I think from the beginning, we never really got pigeonholed into that sense of... I mean yeah, mom wanted us to go to school, go to college, and of course get a job, but I was always very curious from the beginning. And going through school, I always knew what I wanted to be. I always knew I wanted to be a veterinarian. But as I got into my ninth grade year, I got tired of school and I actually quit. And I made up for it by getting my master's degree in chemistry.

Rebecca Fleetwood Hession: Let's just pause because that's what I love about your story is it illustrates what I have been trying to share with the world as much as possible is we put so much emphasis on grades and completion and checking boxes on things that aren't necessarily an indication of future success. And your story is a perfect example of that. I can just imagine if you wouldn't have had the kind of mom that you had, that would have freaked out most parents. Oh my gosh, she's quitting school in ninth. And it had nothing to do with your intelligence or your drive or your desires, you went on to get your master's degree in chemistry for God's sakes. It's not even-

Kelly Gordon: Exactly. And I look back on it now and I say, if I look back and say, what was the smartest move my mom made with me, it was letting me drop out because the interest wasn't there, the intrigue was not there for me. So going back to that curiosity, I needed something constantly challenging me, something constantly driving me. And school wasn't doing it for me. So mom said, " All right. Well, what are you going to do?" And I said, "Well, I'm going to run the horse boarding facility." So I did.

Rebecca Fleetwood Hession: You were a freshman in high school.

Kelly Gordon: Yeah, so I did.

Rebecca Fleetwood Hession: Okay. Of course, you did.

Kelly Gordon: So I did that. And this goes to the curiosity and it goes to my mom's saying, " All right, you can do and be whatever you want." And I did that for a while and it was successful. And I welded for a while and ran the tractors on the farm for a while. And then finally, I said, " Okay. Well, maybe I should go back to college." And college challenged me and college provided me with that curiosity. And so then I said, " All right. I want to go to med school." I got into med school, I didn't go, and so this is where things took a little bit of a turn for me. And I decided to go to grad school out in North Carolina. Actually, maybe a little bit of it's my sister's fault. I didn't leave the state of Indiana, fly or see the ocean until I was 23 years old. And as I was graduating from undergrad, Brandy said to me, that's my sister, " What do you want for your graduation present?" And I said, " I want to see the ocean." Well, I was just joking, and little did I know she took me to Cancun. So I got to do everything at once. Leave Indiana, fly, and see the ocean. Well, I've always been a water bug always. And so after that, I kind of took a little bit of a detour and decided to go get my master's degree in chemistry and went to North Carolina. And so that's when I found the ocean and that's when I found motor yachts. But I did something else before I found motor yachts. So going from not really liking school, then I became a chemistry professor.

Rebecca Fleetwood Hession: Makes perfect sense.

Kelly Gordon: Makes perfect sense.

Rebecca Fleetwood Hession: But that's what I love about this story and why I think more of these types of stories need to be told is this is an okay way, this is a great way to do life. It's not that you did it wrong, you just did it different, you did it your way.

Kelly Gordon: Yeah, I did it my way and inaudible, but I mean, without inaudible, I've been successful at it. I've always been able to pay my bills, I've always been an upstanding citizen, I've always made a good wage. I don't think that's how you define happiness, which is a whole nother podcast but-

Rebecca Fleetwood Hession: Amen, sister.

Kelly Gordon: But I'm happy. And I just think so many young adults get pigeonholed into you have to pick one way, you have to go to college, you have to pick this one career, and you have to do that. And there's no one exact way of doing life. And I had such a curiosity, and I think a lot of people stifle that curiosity, or somewhere along the way, something happens and it gets snuffed out. And mine never did. And sometimes I find the opposite. I'm like, okay, inaudible a little bit. So no, you're right. There's not an exact prescription for life. And if anything, Giana, my mate, saying she's my mate, she gets a lot of questions, are you going to get your captain's license?" And she may, but I really don't think she wants to. And in fact, she's told me, she's come to me and she said, " Do I have to get my captain's license?" And I said, " No, you don't." I said, " You're at the top of your department." It's called the deck department. And I said, " You are at the top there and you can stop there." I said, " You don't have to take and follow a certain path because somebody says or the rule book says this is the way that you're supposed to go." And she's getting right now, she's 22, a lot of people are asking her, " Well, what are you going to do? If you're not going to go to the top and be a captain, what are you going to do?" And she comes to me with, I think probably my teaching background and everything like that, and she says, " Do I need to know?" And I'm like, "Hell no, you don't need to know."

Rebecca Fleetwood Hession: We have done such a disservice to our youth in the last few generations of the pressure, the anxiety that it creates for them to think they have to know what they're going to do. I watched it with my daughter who's 19. The pressure started when they're like 15. What are you going to do? What are you going to be? Where are you going to go? And it's like, my God, their brains aren't even fully developed. And at 22, why would she ever need to decide the rest of her life at 22?

Kelly Gordon: Exactly. Well, and I joke with her and I tell her and I'm like, " No, you don't need to know where you're going to go or what you're going to do." I said, "Hell, I don't even know what I'm going to be when I grow up."

Rebecca Fleetwood Hession: Same. And I'm a lot older than all of you. Same. I'm still exploring too.

Kelly Gordon: Exactly. So inaudible I think this curiosity should be fostered, and I don't think we should be pigeonholed into just one career. And so yes, yes, yes, and yes.

Rebecca Fleetwood Hession: Because you don't start over. That's the other thing that I always encourage people to recognize is... One of the things that I love about your story is you talk about how driving tractors on the farm in rural Indiana helped you to be confident and almost kind of jump into being the captain of a huge yacht. You were comfortable behind machinery. That's an example of experience that you use moving forward. There's experience that you got doing all the things that you did before you got to this place that you're using probably in some way to do what you're doing now. Just because the career is different doesn't mean you start over. We as humans have all of the built up experience and lessons that we've learned, and we carry that into the next place that we go.

Kelly Gordon: You're so right. Because yeah, that's exactly what I said when I first stepped foot on a motor yacht, was I looked at the captain at the time and in my curiosity and in my drive, I said, " I want to learn how to do this." I didn't know bow from stern, I didn't know port from starboard, and I said, " I want to know how to do this." And I looked at him and I said, " I can do this." And he goes, " You think so, huh?" And I said, " Yeah, it's just like driving a tractor." And he says, " All right. Well, come back tomorrow." And I'm going, Oh my God, what have I just gotten myself into? And it just went from there. But yeah, you take previous life experience. So I wasn't afraid of heavy equipment. It was my hand and eye coordination that I developed from stuff like that, that I could translate to that. Or take what I do now. I deal with different groups of guests from different affluence every day, all day long. But my experience standing up in a lecture hall in front of hundreds of students for three hours at a time and yapping about chemistry has what allows me to face them without any fear whatsoever and tell them when they step foot on the boat, here's where we're going to go, here's what we're going to do, here's the safety things, here's the do's and the don'ts and not be afraid of it. So you're right. So when you do change careers, so to speak, you're not really changing career, you're just taking a detour.

Rebecca Fleetwood Hession: And I think that's where we've gotten it completely wrong recently in the last couple of decades is that we believe that our career is our identity. And I believe that we are living a human story that our careers are a part of. So there may be there's the chemistry chapter in your life. There's the boat captain chapter in your life. I think our stories have chapters, but we are not our jobs. And I learned that the hard way because when I left a career that I was wildly successful in, I had a little bit of an identity crisis on my last day because I had chosen to leave to start my own business. But all of a sudden, I was like, I don't know how to introduce myself because I didn't have a title. I wasn't a part of this big international brand company. I didn't even have a business card. I had this weird... like, who am I without that? And I knew right then that I had to start stewarding this conversation that people are afraid to leave jobs that they're even not really satisfied in because of that unmoored feeling of not being attached to a career or a company or a brand. I think when we do that, we limit so much about ourselves and what we're really curious about trying.

Kelly Gordon: Oh well, and I think that's so true. And my current boss asked me, he said, I think he was trying to get an idea how long I was going to be around for, he can't blame but he said, " How long are you going to do this for, Kelly?" And I looked at him and I said, " Until it isn't fun anymore."

Rebecca Fleetwood Hession: That's always my response. That's so funny.

Kelly Gordon: Yes. And I'm like, " Until it's not fun anymore." I mean, why would you stick around for-

Rebecca Fleetwood Hession: Yeah. And I did longer stints. I did a 10- year career and then a 19- year career, but the job changed so dramatically over that 10 years doing different things and working with different clients that I stayed, it was still fun. But the minute it started to wane and wasn't fun anymore, I was like, I got to go. And people said to me, " You're leaving a career with a really great company that you've been wildly successful at making tons of money. You're leaving?" And I'm like, " Yeah, it's not fun anymore."

Kelly Gordon: Yep.

Rebecca Fleetwood Hession: I was bored. It's like, I got to go do something else.

Kelly Gordon: And I think going back to that, what defines happiness, I think so many more people would be happy if they, instead of maybe chasing the dollars, if they fostered that curiosity within themselves.

Rebecca Fleetwood Hession: And you said this, you've been successful in these various things that you've done because you're interested in it, because you want to learn it. And when we engage our brains in a way that we want to learn what we're doing, you by nature are better at it, and then you likely are going to be paid well for it because you're really invested in it and love doing it. And I think there's that... I remember there was a book in the 70s called Do What You Love and the Money Will Follow or something like that, and that phrase always sticks in my head that why would I want to live out massive numbers of years of my life doing something I didn't like or love or wasn't curious about just for a paycheck? No, thank you. I think you have the opportunity to make really good money doing really interesting work if you let yourself be curious about it.

Kelly Gordon: Oh, I agree. And if you find a job that maybe it doesn't pay exactly what you want, well, then adjust your lifestyle a little bit so that you can have the job that makes you smile a little bit bigger every day.

Rebecca Fleetwood Hession: Amen. So tell a little bit of that story about, so you said to the guy, " I want to do this," and he said, " Come back the next day," and he teaches you how?

Kelly Gordon: Well, yeah. So we leave the dock, it's just he and I on the boat, and he's an owner operator, and it's an 80- foot motor yacht. And so we leave the dock and I know nothing, and I'm nervous because I'm like, great. Now I open inaudible. And so we get underway and we go out into this big open area. It's called a turning basin and it's a big open area where container ships can come in and maneuver. And so you're not going to hit anything, the water's plenty deep, that kind of thing. And we're up on the top of the boat. And he goes to leave the helm and he leaves me up there by myself. And I'm like, " Wait a minute, where are you going?" And he says, " Well, you said you could drive the thing, so drive it." And I was like, oh my God, what am I supposed to do? So I had watched him enough the day before, so I grabbed the controls. I obviously didn't give it any juice, I didn't want it to go fast, but so I grabbed the controls and I started maneuvering it around a little bit. And he eventually came back up to the top to actually start helping me and instructing me and stuff like that. And I think he saw... Well, I know he did. We talked about it later on. He saw my curiosity and he saw my want and my drive and my eagerness to learn. And he just took me under his wing. And I tell him now, I still talk to him and tell him now, " If it hadn't been for you, I wouldn't be where I am." And he says, " No, I just gave you the tools and you used them." crosstalk.

Rebecca Fleetwood Hession: That's good.

Kelly Gordon: And just being bold and brave enough to do something, having confidence in yourself. Again, this goes back to my mom saying, " You can do whatever you want." I remember him saying to me, he says, " Why I bought the boat, I wanted to start a charter company." And I said, " Oh okay." And he says, " Well, what do you think about starting a charter company?" And I'm like, " Oh, I'll do it." And I'm like-

Rebecca Fleetwood Hession: This is the second day that you've been on a yacht, and you have now learned to drive it, and you've committed to starting a company.

Kelly Gordon: I'm like, what does a charter company do? I look back at this guy and I'm like, what the hell were you thinking? Because there is no other yacht owner on the face of this planet that would let a girl learn on their 80- foot motor yacht, and no other guy on the face of this planet that would just give her the reins to starting the charter company. So I didn't know where to start. So I was like, " Okay, well, I'll start the charter company, but do you mind helping me?" And he's like, " Well, there's a charter boat show going on in the BVI." And I was like, " Okay, well, why don't we go?" And he's like, " No, I don't want to go. You can go yourself and take care of it yourself." And I'm like, oh my God, he's sending me there by myself? So I go down there around all these massive charter yachts and these crew and these agents that know everything about the industry, and I've been trying to act like I know something, but I just learned about from stern the other day.

Rebecca Fleetwood Hession: Another aspect of this that is really, really important is confidence. When you have confidence in yourself, people feel that.

Kelly Gordon: Well, they do.

Rebecca Fleetwood Hession: And I'm sure he was like, she's confident, she'll figure it out. And that's the truth. You do figure it out.

Kelly Gordon: I was just getting ready to say that. I was just getting ready to say, you took the word dry out of my mouth, he would always say, she'll figure it out. And as time went along, he got to where he would say to other business folk or just to other people or friends or whatever, he is like, " If you want to get something done, give it to Kelly." And that's just kind of where it went. And we did. I mean, we grew the charter company, and I went past him in my yacht handling. And it's funny, we talk now-

Rebecca Fleetwood Hession: That is funny.

Kelly Gordon: I got to give him credit though. He's one hell of an ocean navigator. He sailed around the world solo. So he's got an amazing ability, but I will say, and I can say it now with, again, confidence that my ability to maneuver a motor yacht is better than his and he'll agree, but again, if it wasn't for him, I wouldn't be where I am today. And he took me under his wing and allowed me that opportunity. And so he taught me what he knew about the industry, and I ran with it. And then everybody that I ran into going back to feeling that confidence, everybody that I came in contact with was so supportive and so willing to help. I think everywhere I went, I had a great support system.

Rebecca Fleetwood Hession: I, like you, had parents who didn't mandate or dictate what I did. And I said on a podcast a couple of weeks ago, they asked me what was the, I don't know how it was phrased, secret to my success or something. I don't know, something weird like that. And I said, " One of the biggest gifts I know now is that my parents didn't saddle me with expectations. They just let me figure it out." And when I think about the number of clients that I coach, these are executives, they've got great careers, but there's still this sense of some lacking confidence. And I think when we don't allow our youth to figure stuff out, we miss out on an opportunity to build that kind of confidence in ourselves because we all have unique gifts, talents, and abilities. It's just, where am I going to choose to use those? And the more confident I am in my abilities and my ability to figure stuff out, then I'm going to be more courageous to follow some of that curiosity and try some stuff. And I think often, what holds us back from doing that is just that uncertainty and that lack of confidence in our own ability to figure stuff out.

Kelly Gordon: So where does that come from then? I mean, does it come from within? Does it come from your parents? Is it just an innate character?

Rebecca Fleetwood Hession: Yes. I think it's a mixture of all those things, right?

Kelly Gordon: Yes.

Rebecca Fleetwood Hession: And so some got more of one thing or the other, and some have... My son's a songwriter, my daughter's an artist, I'm a writer. So I think we all have something that we're good at. You obviously are good at the linear thinking of chemistry and figuring out how to put things together into formulas. We all have these things that we just think go to this one career. And I'm of the belief that you can take those gifts and talents and use them in a lot of different ways, but you have to be able to see them as gifts, talents, and abilities. When we only see our career or our title or our industry as who we are, then we've just limited all the ways that we could use that gift and talent. There's a million ways that I could use the things that I'm good at. Right now I'm using it to be an executive coach and I'm a keynote speaker and do the podcast, but I could use these gifts and talents that I have in another way, just like you've been able to do. And I don't think we've been given the permission or the expectation that that's okay because school taught us that there are right and wrong answers, and that's not true. There are a lot of right answers for most of the human challenges that we have. But we believe that there's a right way and a wrong way. And you don't want to explore the way that everybody else hasn't done because what if it doesn't work out?

Kelly Gordon: For me, if you have a characteristic about yourself that's maybe deemed as less than ideal, you're not taught how to channel that in a good direction. So I can name three people off the top of my head that are very type A and are high anxiety, and that would be myself, it'd be my sister's oldest, and it would be the guy that taught me to run boats. And I got this piece of wisdom from him because us three all run very high anxiety, but it's also being that type A personality. And I had this conversation with JC, my sister's oldest, after he had this conversation with me many years ago, was that high anxiety that people say that you need to get ahold of and is bad, no, learn how to channel it, learn how to utilize it. I told JC and I said, " You take that anxiety and you utilize that anxiety at her point in life to get those good straight A's to get where you want to go." She wants to go to veterinary school. Going in the direction that I went. I said, " So use that anxiety to make sure that you study hard and you get those good grades." Where Dan explained to me, he said, " I used that anxiety to make sure that I double checked and triple checked my navigational plan when I was sailing around the world." And he said, " That's why I made it back in one piece without any accidents." I use that same, I call it my neuroses, I use that same anxiety double checking, triple checking. inaudible will get navigational plan, waking up at two o'clock in the morning where I'm stressing and I'm like, " Okay, well, if you're going to be awake at two o'clock in the morning, go ahead and look over your charts for the fifth or sixth time." And I think that's why... That's a good segue into one of the most recent trips that I'm proud of that Dan and I just made as female crew along with Shane. We can't forget Shane inaudible.

Rebecca Fleetwood Hession: We cannot.

Kelly Gordon: I utilized that anxiety to triple check, double check, five and six times check my navigational plan to go from the bottom of the country to the top of the country through some of the nastiest rivers, the Mississippi River being one of them. And we did it as a female crew and we got a lot of looks along the way. And it wasn't that we just did it one time, we did it back to back.

Rebecca Fleetwood Hession: Twice.

Kelly Gordon: We got here, and I say here being Chicago, and we're back in the boat and then there's a guy there that John and I are looking at each other going, do we know him? And he's saying, " Hey, can you go back down and bring another boat back up?" And we're like, " Why?" And we're like, well that guy messed up and he ran a inaudible and we heard you guys made it up here successfully without having any insult to injury. And I'm like, wow. That was crosstalk.

Rebecca Fleetwood Hession: Because you were the one that was up at 5: 00 AM, 4: 00 AM checking all day.

Kelly Gordon: Yes.

Rebecca Fleetwood Hession: Yeah.

Kelly Gordon: Yeah. So take those, what some may say are negative attributes of my anxiety or whatever, channel them in a positive way. And I've learned how to do that now. And so I do. I know that my eyeballs are going to pop open at 2:00 AM every morning on the dot. They just-

Rebecca Fleetwood Hession: Oh, wow. Do you go back to sleep?

Kelly Gordon: I do, and I get my best sleep in between four and six.

Rebecca Fleetwood Hession: Okay.

Kelly Gordon: So I don't fight it anymore. I utilize it. We're actually getting ready to do that river trip again. So we've been asked for the third time now to do this river trip, the guy called me up and he's like, " Hey, I heard you guys did back to back. You did it safely without incident." He said, " I want to take my boat down." He was like, " Can you take it down with the same team?" So us girls are going back down again. So it'll be a girl boat with Shane and inaudible again. And so it was a cool trip. I mean, going into being a female captain in a male- dominated industry, and it seems like everything I've done has been in a male- dominated field, I was a welder, I was a scientist. I mean, there's not many female chemists running around. There's not many female welders running around or captains. And I've always gotten looks as a female captain, and I don't know what those looks are sometimes. I don't know if they're coming out looking to see if the female's going to bash into the dock when she's coming to the dock, or if they're looking going just, is that a girl running the boat. But inaudible coming up the river system, it was kind of cool because people started asking for pictures of us, people asking for our phone numbers, people asking, " Oh, I wonder if the captain will talk to us." And that's when I was like, wow, I got to do something with this. I don't know what I'm going to do or how I'm going to do it, but I got to share something somehow with how do I reach out to people with this confidence, this curiosity? You don't have to follow one path in life, follow your curiosity, don't be afraid, have that confidence to go after what you want. If you want to change paths three or four or five times, do it. Don't let anybody get in your way. Don't be afraid to ask. Ironically, being in a male- dominated industry, my biggest supporters have been the guys. So yeah, I think I went down a rabbit hole.

Rebecca Fleetwood Hession: No, I love it. That's exactly the message I wanted you to share today. So do you think that by being in male- dominated industries, it gives you the opportunity to go in curious and ask questions, and that people are actually more interested in helping and supporting you than people realize they're going to be? Because that's been my experience a few times where the best thing that I could be was I didn't know what I was doing. So the only option I had was to be curious and ask questions. And when you ask people for help and ask them to teach you and show you, I was surprised at how excited people got to help me.

Kelly Gordon: Yeah. I think they genuinely are. I think I've run into one butthead in my career that didn't think that women should be in this industry, but we're still friends. We laugh and we joke about it, and he openly and honestly told me that I don't think women have any place at the helm. And I was like, okay, that's fine. We'll agree to disagree. I still call him up on occasions. He lives in a different country, and when I'm in that country and I need his local knowledge, I still call him up and I'm like, " Hey, Poway, I have a question about this or that" He'll answer it, so it's not a bad thing that he does-

Rebecca Fleetwood Hession: crosstalk very cultural too. If he's from a different country, it could be-

Kelly Gordon: Well, it is. crosstalk. It is rooted deeply. And we both have an agree to disagree, but he still willingly helps me when I have a question about navigation through that area. So when I approached the guys now or when I was learning so much, they were very willing. They wanted to share what they knew. They wanted to help. You'd run into a couple of buttheads every now and again, but you know what, those are the ones that you dismiss, and those are the ones that you don't want to learn from anyways. But they were few and far between, and they probably had something going on that day anyways that-

Rebecca Fleetwood Hession: I was going to say there are buttheads in every industry and every place that you go day- to- day. Some days I'm the butthead, right?

Kelly Gordon: Exactly. And some days I'm the butthead. But that's when you run into those though, you got to keep going and you got to... There's days that you want to quit. There's days that you're afraid to ask the question and you're like, oh God, I should know the answer to this question and I'm going to feel so stupid, but I have to ask it because I don't know. And you got to get up that courage to ask and not be afraid. And I think sometimes, as women in a male- dominated industry, we're afraid because we don't want to sound stupid or I don't know what it is, but sometimes we just don't want to. And I think maybe we just don't want to sound dumb asking the question. But you just have to keep pushing, you have to keep going.

Rebecca Fleetwood Hession: What would you say to somebody that's listening that is in that situation right now where they want to try something, but there's that insecurity and uncertainty that's keeping them from making the jump? What would you tell them?

Kelly Gordon: I visualize myself blocking my nose and jumping off of the deep end of a swimming pool and just taking that plunge and going is how I do it. I'm just like, it's just like, hold your breath, block your nose and go. Just jump. Just go.

Rebecca Fleetwood Hession: Just go.

Kelly Gordon: There would be times that I wouldn't want to go ask somebody something, I wouldn't want to go talk to somebody about something on maybe a bigger boat or something like that. And I would be like, okay, just do it, just do it, just do it. Just count to three. Just go do it. And I would go do it. And I would just get up. But it was a lot of self- talk. I have a lot of conversations with myself in my head, and I think that's so important. I mean, you can't underestimate the conversations that you have to have with yourself in your head.

Rebecca Fleetwood Hession: We are our first responder. How we talk to ourselves is the first conversation we have about anything.

Kelly Gordon: Yes.

Rebecca Fleetwood Hession: So I agree wholeheartedly. It's one of the things I teach my clients most is, okay, let's first learn how to talk to yourself then we'll worry about everybody else. But how you talk to yourself matters the most.

Kelly Gordon: Yes. And I didn't fully realize that until you just confirmed what I've always said to myself. I'm like, okay, I got to talk to myself. I got to be my cheerleader. I got to have my little pep talk. I got to tell myself I can really do this. And I didn't really realize I was doing that until you just now said that. But yeah, if we tell ourselves, oh no, you can't go talk to that owner on that big boat over there, he's not going to want to talk to you, you're on a smaller boat. Why would you tell yourself something like that?

Rebecca Fleetwood Hession: Right. I have this little thing that I do. I have personified the voice in my head. So I call her the little bitch in my head. So when she says that, don't do that, you're not good enough to do that, you're going to look stupid, that's that inner voice, and I say, she can sit beside me in the passenger seat with a seatbelt and a snack, but she doesn't get to drive because we're always going to have that inner voice, but we have to be able to take control of the wheel and calm her down and say, no, this is what we're doing. That inner dialogue is to me, the difference between those that do big, bold, beautiful things and those that don't.

Kelly Gordon: You're right. You're absolutely right. If we don't get ahold... because that's the first person that talks to us. It's not the good friend, it's not your colleague, that's the first person that talks crosstalk in your head. I like that.

Rebecca Fleetwood Hession: And I've personified her because she will be with me until the day I die. So it's not like I can out career her or out smart her. She will always be there. So she's always going to be here. I just made up a little title for her and that's how she lives with me and that's how I deal with it. But the other thing, especially during COVID that I spent a lot of time talking to people about was in crisis mode, how we talk to ourselves. So I started using the first responder analogy is you know what, if you rolled up on an accident, which is kind of the trauma we were all feeling when COVID first started, you wouldn't roll up on an accident and say, is your report in on time? Do you have everything caught up? Was this your fault? You would say, are you okay? How can I help you? And I think one of the other inner dialogue things that we, especially as women need to get better at is being loving and kind to ourselves, especially in times when things aren't going as well as we'd like for them to do, because beating ourselves up only does more damage and wrecks our confidence even more. But if we can lovingly and kindly talk to ourselves like we would to that friend or that family member, what a difference that can make in our confidence and our courage too.

Kelly Gordon: I'll beat myself up all day long for making a mistake, all month long. But I had to channel those and I had to say, okay, well, I love to learn. There's no denying that, that's why I've taken crosstalk.

Rebecca Fleetwood Hession: That's obvious from your career path.

Kelly Gordon: I love to learn. And that's probably why I take so many faults in the road is because the minute that I'm not learning is like, okay, I got to do something different if I'm not learning. So if I make a mistake, I just beat myself up so bad. You don't have to say anything to me because I'm already telling myself how bad I messed up. So how I had to channel that was, well, the only way we learn and I like to learn is by messing up, by making a mistake. So if I make a mistake, the good thing out of that is I learned something new.

Rebecca Fleetwood Hession: Absolutely. And our brains actually kick in when we're uncomfortable in that space of, I messed this up, I got to fix it and figure it out. Your brain actually kicks on some extra juice there to get you out of that uncomfortable spot. So it's the best place to learn is when you're feeling really uncomfortable.

Kelly Gordon: Yes. So when you say when you've got people that are trying to get up the courage to maybe do something, to pursue an avenue or a career that they otherwise wouldn't, what piece of advice, it goes back to that... I mean, geez, all that psychobabble we've been hearing about and reading about and all these books about that relationship that you have with your inner self, I guess there is some truth to it after all. You really got to have a good relationship with yourself. But also, one of the interviews I had last month hit on one of the best pieces of advice I could give to somebody. You got to have a mentor in life. You got to have a support. I think that's important too. I mean yeah, you ultimately have to be your own cheerleader, but you need it. You need an external cheerleader.

Rebecca Fleetwood Hession: You didn't realize you did it, but you just brought this full circle because the title of this podcast is Reflection and Connection for High Achieving Women. You can't do it alone because you can only stay in your own head for so long. You've got to have connections through mentors, strong community, people that are there to walk alongside you or encourage you, or sometimes push you in the pool if you're not willing to jump yourself.

Kelly Gordon: Yes.

Rebecca Fleetwood Hession: So you've got to have reflection and connection. I agree wholeheartedly. And I had to work on the connection piece. I was raised an only child on a small farm in Southeast Indiana with my older uncles on my grandparents farm. And I was alone a lot because I was the little girl on the farm and everybody else was busy working and stuff. And so I got really comfortable being by myself. And so over time and when I became a leader and then when I became successful in sales, I learned the value of connection and I learned how important that was for my career. So I learned it through my career, but now I realize to have a high quality of life in general, we need connection. We need people in life with us for us to feel like we're truly thriving.

Kelly Gordon: People that are inherently leaders because you want to do it yourself, do it yourself, do it yourself. But in order to really, really, truly be good at your task or your career or your position, whatever you want to call it, you have to rely on other people. You have to have a team. Whenever I introduce Giana to the group that's on the boat for the day, I'm like, " She makes me look good." But there's a lot of truth in that. It's who you surround yourself with, it's your team, it's your connections that make you look good. It's I guess just kind of a fun way of saying, offer you that support and help get where you're going. Even though she's my mate and I'm the captain and I run the show, it's my leadership that allows her to do her job effectively. But it's her doing her job effectively that makes me look good. It's a team thing. It really is.

Rebecca Fleetwood Hession: It's all intertwined. It absolutely is.

Kelly Gordon: So you have to have the connections, and you have to have the mentor. I still reach out to him. Once a week I talk to him and I'm like, " I think I'm going to do this." And he'll be like, " I think that's a great idea." Or, " I think I'm going to do this." And he'll be like, " What the hell are you thinking?" And you have to have that. Or I talked to my mom the other night for an hour and a half and it was time I needed the good old hour and a half mom conversation. And so you can't do this all by yourself.

Rebecca Fleetwood Hession: And that's why I love being a coach because so many of the people I work with have tried. And when they realize that they're not meant to do this alone and they start to share with me and we start to do things together, and you just see them open up. And it's my favorite part of my life now is just watching them grow and watching them get excited about their life again because they're not in it alone. They're not ruminating in their head about ideas. They'll run it by me, and like your mentor, sometimes I'll go, " That's the craziest thing I've ever heard. Why are you going to do that?" And sometimes it's just that push in the pool, or it's just saying, " Hey, try it. I'm here if it doesn't work, and I'm here to cheerlead if it does." But when you know you're not alone, it's different.

Kelly Gordon: Well, and I think people that are in leadership positions feel like... Well, like being a captain is a lonely position sometimes because you're the captain and you're running the show and it's a boss position and it's you at the inaudible and then everybody else is running the rest of the bone. And then it's kind of a lonely position sometimes, but I foster a different kind of an environment. And I allow myself to be human. I mean, if I'm sad one day when the dog died and I was crying, they knew it. I mean, if I'm overly happy about something, they know it. I think some leaders get stuck in their head where, oh, I've got to be this almighty strong leader that I can't let anybody else in, I can't ask for any support because that somehow has become public's view of what this strong pillar of a leader it is. And it's dumb because... And then it dehumanizes what a leader is.

Rebecca Fleetwood Hession: It's why we have burnout. It's why people are struggling with their, I think mental health even at work because we're afraid to be humans.

Kelly Gordon: Yes. And I just am kind of like, I refuse to do that. I'm like, if I'm having a bad day, it's okay for you to know it. If I am happy, if I'm sad, if I don't know something, I'm going to tell you I don't know.

Rebecca Fleetwood Hession: My least favorite thing is when people say, well, don't take it personal. I'm like, that's not a thing. I am a human, I am personal. We're at work, but I'm still going to take it personal because this is my life. Or when people say, well, we shouldn't get emotional about it or bring your emotions to work. I'm like, that's like saying, don't bring your arms to work, they're inconvenient. Everybody brings their emotions to work. That's who we are. Humans are personal, emotional, and social. End of story. That's just it.

Kelly Gordon: This one kind of got me one time. I had a fellow in this industry tell me, he's like, "Well, I know you're putting a lot of emotion in this decision because you're a female and all."

Rebecca Fleetwood Hession: Oh.

Kelly Gordon: And I was like, first of all, two things here, I don't make business decisions with emotions, but second of all, I will make them as a female because newsflash, I'm a female. Am I supposed to put a penis on because I'm in a male- dominated role? No.

Rebecca Fleetwood Hession: Crazy. And by the way, people make all of their buying decisions with emotion and validate them on facts. Our human brains are wired to make decisions on emotion.

Kelly Gordon: They are.

Rebecca Fleetwood Hession: We pretend like because we're at work that... That's not true. And it's actually why women are great leaders because they have the ability to connect with that empathy and bring that humanness into the team. And people have a higher level of trust for leaders that are willing to do that.

Kelly Gordon: And suddenly, at the beginning of the season, I wanted to implement more morale days, days that we took the small boat out and we went and played on the small boat, or days that if we just wanted to lay out inaudible on the boat, which we didn't get too many days to do because we do work a lot in this industry. But I wanted to be able to connect with my crew a little bit more to know when they're burned out or when they're in a funk or when something's going on. And not that neither you or I am a woman hear me, but yeah, I do think that there is something that a woman has in a better ability to lead. I want a female captain and they're like, I don't want a male captain. I prefer a female captain. And the guy that I work for, he's like, you want to get shit done? Ask Kelly. I worked for a guy out of New York, he's like, nope, don't hire male captains. And it wasn't anything creepy. It was a matter of getting things done. The guy that I work for now, its interaction with the guests. Going back to that, keeping emotion out of it, I'm like, how do you keep emotion out of it? I'm like yeah, I know how to make a business decision, but we're human beings. How do you take emotion out of making decisions?

Rebecca Fleetwood Hession: You don't. You may fake it and pretend like you did, but it's not a thing. And so I'm passionate about bringing the personal, emotional, and social aspect back into business because when you bring it into business intentionally and use it for good, that's the way you combat burnout is you let people be humans. You give them the expectations. You give them the control measure optimize of the business, but you let them be humans. And humans are uncertain. We have good days, bad days. Like you said crosstalk.

Kelly Gordon: We're emotional beings.

Rebecca Fleetwood Hession: Yes. Yeah. We shouldn't walk into work every day thinking that we are a machine there to produce. We're a human there to add value and have impact and be relevant to the business, but we're not a machine to produce. That's not a thing. I do have to say that I think it's funny that you and Giana were captain and first mate and Shane was the chef. So I just think that's funny. So I had to get that plug in there.

Kelly Gordon: Poor guy, and he's getting stuck and doing it again.

Rebecca Fleetwood Hession: Thanks Shane for cooking the meals. And I think you do have a great message to inspire people to challenge their current way of thinking and be more curious. It's good stuff. I told you you'd been inspired. Do you not just love her and that story? So again, as I said in the beginning, I hope this inspires you to be more curious. Be more curious about your heart's desires and learning something new and stepping out into something you've never done before with just the sheer confidence that you're just going to figure it out. Just as I was hitting record on this podcast today, I remember what it felt like just trying to figure out what buttons to push to get this damn thing to record. And it was the act of just figuring it out where I got more and more confident. No, this podcast is imperfect, it's never going to be perfect, there's lots of things that I wish were better and different, but I love the feeling I get now when I go to record an episode knowing that I figured it out. And I think you'll find tons of confidence and inspiration in your own story when you just start stepping out to figure it out. All right, make it a great day. And if you haven't yet subscribed to the podcast, this would be a good time to do it and share it with all your badass friends as you do.


We need to allow ourselves to be curious. When we are curious, we challenge our current way of thinking and we can learn more about ourselves. Our curiosity drives us to step out into something we’ve never done before and just figure it out. It’s this act of figuring it out that gives us confidence. Once we start to evoke that sense of confidence in ourselves, others start to have more confidence in us.

In this week’s episode, we will listen to Kelly Gordon — the captain of a 75-foot motor yacht — as she tells us the story of how she followed her curiosity and had the sheer confidence to just “figure it out.” In her conversation with Rebecca, Kelly talks about her journey of becoming one of the few female captains in the boating industry, and her success in maneuvering a yacht with a female crew. She shares her deep desire to learn, and how she had the confidence to try something new.

Throughout her life, Kelly needed something to drive her. She needed to be curious about what she was doing or challenged by it in order to succeed. In ninth grade, Kelly quit school, but she later went on to get her master's degree in chemistry. Eventually, she discovered motor yachts and was determined to learn more about them. On her second day ever on a yacht, she figured out how to drive it and committed to starting a charter company. While she didn’t know everything at that point, Kelly had the confidence to be curious and allow herself to “figure it out.” Today, she is a successful female captain of her own 75-foot yacht. As a former chemistry professor, Kelly has changed her career multiple times, and she thinks of her career changes as “detours” rather than her starting over. She discusses with Rebecca how the experience and lessons that she learned and carry that into the next place and that next job. Our career is not our entire identity, and she believes we are living a human story that has multiple chapters, but in the end, we are not our jobs. She also tells Rebecca about how she utilized her anxiety to succeed instead of fighting it. She talks about the importance of being your own cheerleader, but also leaning on your support system when you need them. Lastly, she discusses the importance of being kind to ourselves because the way we talk to ourselves can affect our courage and confidence.

Listen in to learn more about how Kelly had the confidence to follow her own curiosity, and the importance of searching and exploring throughout your career.