Ep. 204: How this remote travel and non-fiction writer helps badass women connect to their personal power with Kelly Lewis.
In this episode, I speak with Kelly Lewis who is an inspirational non-fiction writer and a women’s travel industry maven.
She’s the author of Tell Her She Can’t, the founder of Go! Girl Guides, which publishes the world’s first series of travel guidebooks for women. And the founder of the Women’s Travel Fest, an annually sold-out conference for women who travel, and Damesly, a women’s tour company.
Listen on to find out how Kelly has been able to lead a community of badass women who refuse to believe that anything is off-limits.
Hey everyone. Thank you so much for being here. I am really excited to be with my guest today, Kelly.
Hey Kelly how are you?
Hey, good. How are you?
I’m wonderful. Can you tell us about you and why you live an offbeat life?
Totally. So I am an entrepreneur in the women’s travel space and it took me quite a bit of time to get the confidence enough to leave my job which at the time was bartending. So I was making like a ton of cash.
But the offbeat life really appealed to me because I wanted more freedom and control over my day-to-day life and over my income potential.
That is definitely something that is a lot of a struggle with when we have a day job that pays so hot and you take that. It feels like a really huge risk, and it is, to leave that and do something completely different and you’re unsure if you’re going to make as much especially when you don’t know what’s going to happen.
How did you make that transition and prepare yourself for it?
Yeah. I have to be honest, it took me years to get up the courage to do that. I was bartending and managing a bar in the Lower East Side in Manhattan. Working in the service industry affords a creative personality a lot of flexibility. So I was able to take time off at my leisure.
I kind of always adjust to working around travel which is what I was really focused on and building businesses in. It was so comfortable for so long and I think, while I was financing my business, it was bartending that was doing that, and then at some point, I realized that bartending was starting to pull me back instead of pushing me forward.
And I just thought to myself, “If I don’t make the leap then I’m never going to know if my businesses can be complete businesses or if they will always be hobbies.” So I really just had to trust that I could do it and know, even if I failed, that I could go back to the service industry.
And I think the huge part of it is like the fear that what if you can’t return? But I think the reality is you can sort of always go back to what you’re doing. Maybe not the exact same job at the same sort of type of work.
So for me, it became like, “Well, I have no I have no other choice but to really try.” But it felt kind of like swinging from the monkey bars for a long time and it’s like I was dangling from one bar with one hand for a really long time knowing that I had to reach the other bar. But that swing is so scary that it took me years.
And I do remember thinking like, “I’m never going to make as much money. There’s no way that I’ll ever be able to replace the amount of money that I’m making each week.” And that was a lie.
That was something I told myself a really long time but now, being able to have total control over my schedule, making easily what I was making in a day, in two hours. It’s the best decision I ever made.
Also, another thing is that we are really fearful of, and you talked about fear a lot, is, first, the first step. The first step that you’re going to take in order to actually either leave that job or start that business and then the second thing is a fear of what is the worst thing that’s going to happen?
And for most of us, the worst thing that’s going to happen is we have to find another job or go back to our regular nine-to-five. So honestly, it’s not really the worst thing. You have a ton of skills and if you have to you just go back to it and that’s really what’s going to happen.
So I think we kind of make it scarier than it is and then that’s what stops us from actually going for it.
It’s so true.
Working in service is just really humbling. I was bartending for 10 years before I ever took my business seriously. That is an excessively long time but I like the work and when you’re serving customers you really learn more about people.
And for me, that was the draw. Like I love hearing people’s stories, I love getting to know them, I love creating that connection. And I’ve carried that kind of the same questioning of people, that same sort of like a friendship into the business. It’s like for me it’s always about people, it’s always about getting to know them and figuring out how to tell stories the best way that I can.
And I really am thankful for the service industry for giving me that opportunity. And I also feel like everyone should work in the service industry for at least six months in their life. Like that should be a requirement because you learn how people are treated, how so often service industry members are treated as they’re less than for some reason.
You learn how people should be treated, you just learn so much about yourself and your boundaries. Everything gets kind of tested in the course of doing that work and I think that everyone should have to do it if they haven’t already.
Yeah. It’s really something that you can’t take for granted once you learn all of those things and you remember that and that’s how you treat other people.
I actually tried waitressing for like a few weeks when I was like 16 or 17 and I don’t know how they do it. I was like, “Oh my God. This is crazy. People are nuts.
I am a terrible waitress but I am a hell of a bartender – that’s the thing. Also working in New York City, you’re working until like 4 or 5 in the morning. That schedule started to get too rigorous for me to get up and then work for myself all day and then turn it around. And I just got tired of pouring shots of fireballs at 21-year-olds.
It just became like, “Okay, I’m ready for more than this.” And by this point, I started my initial business Go! Girl Guides in 2010. So I worked for a long time building that business while also bartending. And then I got to the point where it was like and this is kind of a pivotal moment that I think every entrepreneur has words.
It’s sort of a make it or break it and for me, that came during the Obama Administration and I was invited to the White House as one of the top 100 travel bloggers in the world summit. And we were there to talk about the importance of studying abroad.
Seeing the invitation to the White House in my email inbox as I was behind the bar, like opening the bar, it’s New York so there are mice running around behind me and I got that email, and I swear, it was like how Cinderella must’ve felt right before the ball. And I was like, “Okay. This is it. this is. I’m on the path.”
And when I was at the White House with people that I had only ever met online, that I really looked up to, with all of my peers. It really gave me a boost of confidence like, “My career has potential. There’s so much more I could be doing and I need to just keep going down that course.” And even after that, It was still like two years before I quit but I held on to that memory.
And I do remember coming back like taking the bus back from DC, back to New York, putting my bar rag back to my back pocket, and going to work. And I work in this tiny basement dive bar with hardly any natural light and it just felt so deflated. I was like, “Uh! It was all a dream. So magical.”
But I really held on to that and that was one of the turning points for me that was like, “There’s more for you here just keep following this and don’t let money persuade you from that.”
It’s amazing once things start to happen because a lot of times when you’re in the middle of everything you actually don’t think that you’re going to succeed or maybe there’s a lot of obstacles that are coming your way.
Because as an entrepreneur, honestly, for me at least in my experience, like every day there’s always something that is happening. And you don’t actually see a lot of the progress until something happens like with you, Kelly, when the freaking White House contacted you.
I know and I remember, I wrote this as part of the book that I’m writing right now, this memory so specifically and I have this awesome Pizza Chef. So I work in this dining bar that also serves free pizza with every drink.
So I had this pizza chef that I loved and I remember running to him and being like, “Rico, I’m going to the White House.” And I remember us jumping up and down and him being like, “What if you get to meet Obama?” Me, just being like, “Oh my God. What if I get to meet Obama?” I didn’t.
It was just such a moment and it was sort of like a sign from the universe. It’s like everybody that you work with supports this dream. Like, keep chasing it and don’t let yourself be distracted from it.
When you were looking into the type of business that you wanted to get into, to really have more freedom with your life, because, honestly, that’s what most of us really try to achieve when we want to be location independent – we want to have a business, how did you figure out that starting your blog and this business were the right thing for you?
So I have an interesting story as an entrepreneur. My first business actually came to me as a dream in the middle of the night like literally a dream.
So I was traveling a lot of times. I was traveling by myself. This was pre-2010 so pre-smartphone. And I remember meeting up with my girlfriends around the world and they would tell me things. Like, insider, grapevine traveler tips: “Oh, this bus station is kind of dangerous at night…”
Just like things that I couldn’t really find in my guidebook. So this is in my subconscious. And then I was working as a journalist actually and I had a dream in the middle of the night that I was staring at a guidebook for women and I can see like the name, the colors of the book, everything.
And in my dream, I was going, “Oh my gosh. This is totally your calling. You have to do it. Now, Somebody else did it.” And I was kind of like kicking myself in my dream and I completely forgot about that dream until halfway through my workday the next day.
And I worked for this trade publication and I was an editor there. I hated the work, I hated the office. I was like fluorescent lights and a mean owner of a company who would stomp up down the halls.
I just kept thinking like, “Something has to be better than this.” And I remembered the dream midway through that day and it was like, “This is it.” So I started Googling travel guide book for women and I was like, “Surely, it’s 2010, this is definitely something that’s already been done.”
And I realized, in that Google search, that nothing was done in that space. There wasn’t even a woman’s travel space. And I started thinking about all the things that my friends would tell me that my guidebooks weren’t telling me. And I just thought, “This is ridiculous. Women and men travel differently. I travel differently and I need resources.”
And so right then and there I decided I was going to quit that job and literally, 3 months later, I was in Thailand writing our very first guidebook. A lot of this was like learning as you go. There were no women’s travel guide books, there was no women’s travel space. So I had to kind of define: what do I want to include?
I had zero experience in writing a guidebook, zero experience in publishing, and I sort of just had to decide. Like, “Okay, if I’m starting from scratch what would I want? What would I tell my girlfriend? What kind of information? So in every other model out the window., what would I want my thing to look like? And that’s how Go! Girl Guides started.
So we started as a publishing company. We published seven different guide books for women specifically in different destinations. And then my career really grew from there.
So by becoming the first series of guidebooks for women, I was getting a lot of press pretty organically and then I went on this big book tour talking to women around the world about traveling and they loved this conversation.
And they wanted me to stay for hours and pick my brain. There was a kind of energy that came from swapping travel stories. And so I said, “Alright, once I moved to New York after this book tour, I’m going to do this in a bigger way.” And so that’s how I started The Women’s Travel Fest which was the world’s first travel event for women of that scale.
And so my career has really been of my own making. It’s like, “Hey, why don’t I try this out?” It takes a lot of conquering fear to do all these things. But for me, it’s like the FOMO that I would get from chickening out on my own idea is greater than the fear of creating something and totally sucking at it.
I think you definitely hit it on the nail on that one. The worst thing is not having to go back to your day job. The worst thing is knowing that you could have done something great or done something that you really loved and you didn’t do it because of yourself and because of fear.
And at the end of the day, that nine-to-five job, that job that makes money will always be there. There’s always going to be new companies, there’s always going to be other opportunities. But sometimes the things that you have, that you can create may not be there anymore and it could be lost.
So I think that’s even greater. That’s why we really have to go for it even if there’s a huge fear that’s stopping us.
Yeah, I totally agree. And I will also say like there is a big financial component to this and sometimes people want to know what that looks like. And for me, it was maxing out a lot of credit cards. It wasn’t necessarily the best strategy for starting a business but I needed access to money and that’s how I did it in those early days.
And so it’s like I think people get hung up on the financial bit of it thinking they have to get investors or they have to grow super slowly. And I think for me it was more just like, “I have to do this now.”
And so that urgency pushed me forward. It’s a blast through any financial concern or barrier that I had. And that continued for a really long time and I won’t lie and say it like, “We immediately made money.” We didn’t.
We carried a loss for quite a while and The Women’s Travel Fest is an expensive conference. Conferences are expensive. And so I learned a lot through the course and starting these things but that lesson and like those things that I learned are also valuable.
And creating these different businesses that didn’t exist previously, in a space that didn’t exist previously, put me on a different trajectory when it comes to my career. And it gave me confidence because of the response that it was getting.
Like, I could just keep creating and so what if something doesn’t take as much as the others take? I can just keep creating and that is forever my motto like I want to just keep creating things.
And doing what you love which is just amazing when you could do that every single day.
Yeah. And then, after The Women’s Travel Fest, I started the women’s tour company because it was like, “Hey, I have all these women, we’re selling out every year, we’re talking about traveling.” You have to come sometime, it’s such an amazing conference and community. Then it was like, “Why aren’t we traveling?”
So then I started the women’s tour company called Damesly and that continues to grow without knowing it. When I had that dream in 2010 without knowing what my path forward would be and even with the bartending and all the things that I had to do. The many times that I felt like, “This isn’t going to work. I should just give it up and get a regular job.”
Without knowing what my career could be, I had to keep taking those blind steps forward. And I’m so thankful that I did because who knows what I would be doing now? I would forever kick myself not knowing the full length of that path and it is still unfolding.
That’s the most exciting thing I think about being an entrepreneur. It’s like there’s no end to that journey.
We all have a “what now” moment after we take that leap to do what we really want or maybe even leave our 9-to-5. What was that like for you, Kelly? What did it look like to you and how did you kind of manage that?
Oh, it was terrible. It was honestly terrible.
There’s this saying that I have read in books that happens sometimes when you leave the safe to go to the unknown. My whole life exploded. My boyfriend and I had a devastating breakup, my grandmother passed, this all happened within like two days. I was homeless, running low on money, had no place to live or go.
It was so scary and I just had to figure it out and everything just blew up. And I really think that that happens too often when you make a big jump and it’s like the universe is like, “Do you really want this? Will you really fight for this? How invested are you?”
And I did a lot of things. I stayed with my aunt for a couple of weeks. I figured it out, I healed. It took me like a few months to heal my heart from the devastation of all that but I never quit working on my business.
And little by little I started to see like, “Hey, I made rent this month. Hey, I’m okay. I’m doing it.” And that gave me the confidence that like I was actually on to something and it wasn’t stupid to quit my job and I could turn this into a full business.
It’s like you have to jump and then it appears, right?
I wasn’t making as much money when I quit bartending but afterward. I’ve been able to hit multiple six figures in revenue and that’s crazy to me. I don’t know if it’s that I just invested and said, “Hey, I’m going to do this now,” and the universe was like, “Okay, this is the plan,” or if it’s that I can give my businesses more of me and more of my time and focus.
But whatever it was, I’m thankful because it showed me that I can actually do it. But there were certainly 6 months or so where I was like, “Am I going to make it? Am I not?” And it really forced me to recommit over and over and over to that idea.
You know what’s funny to me, Kelly? Is that when we just do the work, when we focus on something things start to happen, right?
But it’s also really interesting how we’re always so surprised when things start to actually come together. If you really think about it and sit down, “Yeah it makes sense because I did so much work for this and I put so much effort in it that it eventually works out,” or you’d learn to pivot when it’s not going a certain way.
So it’s just a matter of putting enough time and energy into it and also learning when you need to pivot or make changes with your business. And it really comes from experience and a lot of blood, sweat, and tears. There’s no easy way into it.
But every month that I made rent and was living pretty comfortably, I was like, “Oh, I guess I can afford this.” And it did take me probably another few months to get comfortable with that and then I really started doubling down.
I hired a business coach to change the game for me and I do remember that investment was so terrifying. Like, I didn’t know how I was going to afford to pay her and it really turned my business completely on its head in the best way.
Having another set of eyes to look at things to be like, “Why are you doing it this way when you could do it this way?” It’s just something so simple that you can’t see ’cause you’re too in it.
So I will say the progression of my path was like: come up with the idea, work really hard at it, and then also at something else just to stay afloat. Finally, let go of that and keep working on your business then double down and invest in mentoring.
And that’s that was a game-changer.
Yeah. And that’s really something that is hard for us to see like you said because we’re so into the game that we can’t see it from an outside perspective. And having, not just a mentor or coach, but the right one can definitely change everything for you.
So, for you, Kelly, when you were first starting out, I know you talked a little bit about this, how much did you actually save to set off and start your business and become location independent? And how are you able to budget those savings to make it last?
I think when I quit bartending and full into my business, I had $2000. I mean, really not much but I just knew that I could do it. And I knew I had a stream of revenue coming in and I had a stream of passive revenue coming in. So it just became like, “Okay, my goal is to focus on the passive revenue and build that up so that it becomes like a main source of revenue.”
I did have a path forward but I really didn’t have much when I let go and I just figured, “Alright, I’ll give it a solid year, see how it goes. If I can’t do it, I’ll go back to bartending.”
And thank goodness you made that decision, right?
I know it’s so hard at that moment but then you think back and you’re like, “Oh my gosh, thank God I made that decision. It was so right.”
It’s so true.
It was so funny because it’s like I kept doing things thinking that was the way things had to be. So, for example, Women’s Travel Fest is a three-day conference, normally set in New York City, one of the most expensive cities in the US, and I was charging like $250 for tickets including, meals, including parties.
And I remember my coach was like, “What are you doing? I just paid $600 to go to a conference in New York last week.” And I was like, “What am I doing?” I just, for some reason, had it in my head that my community wouldn’t pay more.
So when I raise my prices to &397 and I sold out faster than ever. It was like a lightbulb moment. That was like, “Just because I’m struggling financially or I have struggled financially doesn’t mean the rest of the world does.”
And like raising your price point energetically does big things, I think, just for you, for your community, for the legitimacy of what you’re doing. And I do wish that I had done that sooner. It could have made a difference.
So yeah, when you’re starting to do things, you have this frequency of notions ’cause you think that you are your customer. And then you realize like, “Wait a minute, where I am right now is not my ideal customer.
And so you move forward based on like where you’re going and business and I think the pricing is a big part of that. If you’re listening to this and you’re struggling with how to price, get a professional opinion. Like, get a coach, hire someone who can tell you what things could cost by looking at your business from an outside perspective.
So let’s talk about you taking your business on the road. Obviously, your company is based on travel and you help women do that and you also have a conference and it’s all about that. Now, with this whole year and everything that’s going on, how has that affected your business, and how we’re you able to learn how to pivot?
Yeah. It’s been a brutal year for the travel industry for sure.
We were actually able to hold Women’s Travel Fest in 2020 and the show was from March 6th to the 8th in New York City. We know now that US borders closed on the 12th or the 13th. And so that was pretty terrifying, looking at it a week or week after the show because I didn’t realize how close we were.
And when we held the show the advice is very much still like: cover your sneezes, use hand sanitizer. I just didn’t know the extent of the virus. I am lucky financially that I was able to host the show because that would have been a huge hit that I probably could never recover from.
For a frame of reference, the show costs about $60000 to $75000 to run. So I am I’m lucky that we were able to host a show and in hindsight, it was kind of the last fun weekend for me and my community ‘cause we didn’t know what was coming.
But everything else that I had planned for 2020: I was going to do 20 tours in 2020, I had a whole roster of places that we were going to go with Damesly and clients, I booked trips – and everything changed. And I really want to tell you that I was able to like very quickly pivot but the truth of it is I was under the covers for like a solid two weeks. Like, I was terrified.
And feeling the ground collapsed beneath me, having gone through the progression of being an entrepreneur, I suddenly realized I was left with a ton of skills that really I could never do in this coronavirus environment.
Can’t bartend, can’t host live events, can’t travel. So it was like a triple Whammy and it really made me like, “What am I going to do?” But the gift of that is time.
And so I finally had time to not just decompress from this go go go train that I was on but to say, “Okay, now that I have space and time, what other creative interest can I bring back into my life?” And for me, I had wanted to write a book for like 2 years and I just never could find the time to do it.
I threw myself into a new project which was writing this book and it really gave me life. I mean, I could have never imagined how things would turn so quickly and it’s not over. Like, I don’t know when we can get back to normal.
I’m hopeful that I’ll be able to host travel fast later in 2021. And hopefully, we’ll be able to run 2 tours later in 20 21. But in the meantime, I’m welcoming the opportunity to explore what my life looks like as an author.
I’m checking out different kinds of mediums for storytelling and that’s so fun and so rewarding.
It has definitely turned many of our lives upside down especially with you and the travel industry. It is crazy. But we can only hope for the best but then in the meantime, it really gives us a lot of tests with what we can do with ourselves and how we change our business and still crate income and obviously feed ourselves.
And if we have employees, it’s an added stress or burden on you. But I think it’s also great because then you know how to manage things and also really pivot your business.
Yes. And also like having grown up in the way that I did, having to be really scrappy, fight for myself, know how to live on a really lean budget, and in building my businesses many many times that I got down to the last can of tuna fish – I know how to do that.
So it wasn’t super hard for me to go back to living leaner on a budget. But the hard part that I continue to wrestle with is like, “What is the future of this industry and where are we going?” There’s no end to that. There’s no single person that can tell me that.
So in the meantime, I just have to focus on what I can control. And what I can control is how I choose to create in the world and what I choose to put out in the world in the meantime. And that’s the only thing that really makes me feel good.
And I want to say to you like, “Oh, I was able to pivot. I rotated my business because I’ve seen a lot of my colleagues and peers able to do that much faster than I have”. And I have a little bit of guilt about that but everybody reacts to trauma differently.
For me, it was like, “Uh! Hide.” I didn’t want to just reinvent the wheel here. I just wanted to kind of hide from the world a little bit and writing a book gives you the chance to do that.
So it was like another outlet to pour that energy because I just thought, “Well, rather than trying to completely change my businesses, let’s just give it a pause, see how the world works out in the meantime, focus on other things that I’ve always wanted to do.
So, Kelly, let’s fast-forward to 30, to 40 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for?
I want to be remembered as one of the pioneers of the women’s travel industry for sure. I’m super proud of my work there. But I also want to be remembered as someone who encouraged women specifically to fight for their dreams and fight for their stories and not be persuaded by anyone who tries to tell them that they can’t do something.
I had a pretty traumatic childhood. I was constantly told that I wasn’t going to amount to anything, that I couldn’t do it, that I was x y and z names.
I go back to that kind of space and I want to be remembered and inspire other women to say like, “No! I get to choose what my life looks like, you get to choose what your life looks like. I have power in my decisions and in the trajectory of my life.” That is kind of the message that I want to impart.
And I think for a long time, I resonated so much with travel because travel was a really great way for me to tap into my own personal power. So it showed me my limitations: how strong I am, how capable I am. I can get to the world in other languages and I can successfully survive and do all the things I want to do with all these amazing people around the world.
And like showing myself that I was capable of that showed me how I was capable in other areas and that’s sort of where I stayed for a long time. Within this sort of travel space and encouraging women to do the same thing.
And now it’s like I think that travel can be a great way to connect your personal power. I want to explore what the others are. I want to stay connected to that energy of like, “You can do it. You can do it no matter what.” And that’s where I’m headed.
So, do you have anything right now that you are currently working on that you’re really excited about?
Yeah. So I’m working on a book called Tell Her She Can’t and it features stories from my life and stories from the lives of 50 different women who have overcome a ton of different forms of adversity and struggle.
And all of these women, at some point, somebody tried to tell them that they can’t and every single woman responded back with, “Just watch me.” I think that’s really exciting.
I’m also releasing a podcast myself and that’s been kind of fun – to explore a new medium. But really, it’s Tell Her She Can’t and it is giving me life.
Yeah. I’m really excited to read all of the different stories in that book and share them with everyone once it’s out.
Now, if our listeners want to know more about you, where can they find you?
I’m online pretty much everywhere at @gokellylewis and that’s probably the easiest way to find me or through any of my businesses.
Perfect. Thank you so much, Kelly, for speaking with us today. We really appreciate all of the stories that you gave us, some tips. And we really appreciate you sharing your journey with us as well.
Yey! Thank you. It was so much fun.
Audio Engineer: Ben Smith