Ep 5: In conversation with my twin sister!
24 Nov 2021 · 31 min
A conversational episode in Emma Naylor’s 'You Can Have It All' podcast featuring her twin sister Jessie. Jessie recounts her path from a general management/marketing degree through an uninterested, higher-paying early career to deliberately taking a pay cut to re-enter the travel industry — where she found alignment, creative work and later greater earnings. The episode mixes practical guidance (budgeting and planning for career transitions, testing passions via side-projects) with travel anecdotes (upcoming Kenya trip, bucket-list destinations) and a brief career highlight (TTG Adventure & Touring Agent of the Year). The tone is personal, motivational and pragmatic for ambitious women considering career shifts.
Welcome to the youe can have it all podcast. Brought to you by me, Emma Naylor, life purpose, coach and mentor. This podcast is for ambitious and motivated women who are ready to take the next step in their life, to support them in turning their dreams into reality, to help them and guide them to turn their magic back on, step into their purpose and live their most authentic life.
Welcome back to the you can have it all podcast. I am so excited to be here with this week's wonderful guest, who is my twin sister, Jessie.
Hello.
I'm so excited.
I wanted to get my sister on.
The podcast for a while, but we haven't found the time. So here we are together just after a wonderful trip in New York. And I wanted to bring my wonderful sister on to share her own journey of her career, where she's been, what she's doing, and for her to sort of share a little bit of her wisdom about how she has become very, very successful in her industry. So, Jesse, I'd love if you could introduce yourself to the audience.
Yeah, of course. So, as Emma said, obviously I'm her twin sister, which is obviously one of the best things in my life. But the other one, very close to is, you know, when people used to say this, it always sounded so unrealistic and it sounded like it'd be the right thing for you to say. But honestly, my job and what I do is one of the big, big passions in my life. And you know, people always say to me, oh, you work so much, you work so many hours, you never have a break. But to me it just doesn't feel like that, especially when you love, love what you do. So I work for those of you that don't know, I work in travel, which is just my obviously favorite, favorite industry. I absolutely love traveling. We live in this beautiful, amazing planet and there's so much to see and so much to do, obviously respecting, you know, Mother Nature and all of the beings that live on the planet. But there's so much culture to see, there's so many different people to meet, so many different languages, so many amazing animals, cuisines. Just so much to see and do. That travel is just one of those never ending things. So I just fell in, fell in love with it. I think from when I was younger we always used to travel a lot as a family to all these different places with so much different, you know, the things I touched on before, culture, cuisines, different people. So. And I just wanted other people to be able to experience that as well. So, yeah, so I work and travel Now. Yeah.
And exactly as you said, Jess, like, we've always been so fortunate to be able to travel to so many cool places. Like, growing up, I kind of always. It's really interesting growing up, I always wanted to be an air hostess and I think you wanted to be a pilot. Yeah. And it's really interesting that you've kind of ended up working in travel. And obviously our dad also works sort of in that industry as well. And I think growing up with it, you kind of don't really think you can make a career out of something you really, really love. You sort of just see it as, oh, we get to go on really nice holidays and we get to kind.
Of see, you know, nice things.
So how, how did you get into travel? I'd really love to sort of share your story a little bit more of how you ended up working in travel and I guess sort of taking it back to sort of university, leaving university and how you sort of worked your way to where you are now.
Sure. So it's actually quite interesting that you said, you know, how can I make.
A career out of this?
And something I love, because that is something I did struggle with, you know, from university. At university, I did a general degree in management and marketing because I didn't know exactly what I wanted to do. I obviously wanted to learn more about businesses and the world we live in, how everything operates. So I did quite a general degree. And then after that I did actually do an internship and travel, which I loved. I absolutely loved it. But at the same time, I was always very money driven. Not in a bad way, just that for me, my results and my compensation sort of for me, measured, I guess, my success and, you know, how much I was valued at something. So I actually left that internship and went into a completely other industry and I stayed in that industry far too long. It was, it was something I did not have a passion for. All I was passionate about was the money. And to be honest, at the beginning I did think that would be enough. Okay, I don't really have to care about my industry. I just care about, you know, if I'm getting these paychecks and that's great, I'll be happy. And that wasn't realistic. And, you know, I changed different companies sort of every year and I thought, it's the company and if it's not the company, it's, you know, know my manager and if it's not this, it's that. But after sort of, you know, three, three and a half years, I realized it's not actually these companies, it's not the managers, it's me. And because, yes, I'm getting the money that I'm looking for because I don't actually love the industry or love what I'm enjoying or even love what I'm selling. There's only so far that will get me in my career. You really have to love, you know, it's. Everyone knows being a salesperson is very hard. The only way that, not that it makes it easy, but the only way to make it authentic is if you truly believe in what you're selling in. And for me, those two things weren't aligned. So there was only so far that would get me in my career. So I decided that I did want to go back into travel because that's something that I did have a massive passion for. But I knew I would have to take a big pay cut to do that. So before I quit the previous industry I was in and moved to travel, I started thinking, right, this is definitely what I want to do. How can I start making cutbacks so I can sort of compensate for not having this salary? So, you know, I started doing small things like not eating out more, not. Sorry, not eating out more, eating at home more, or, you know, not. Maybe when I go out for drinks, instead of having the top, I don't know, gin, I would order the middle. Just little things like that. So making little cutbacks, which weren't even really cutbacks, they were just things I needed to do to get in the industry I wanted to be in. So I did go and work for a travel company. I worked there for about a year. Like I said, my salary was a lot lower, but that didn't really bother me because I was learning so much about the travel industry, how it operates, how you do, you know, day to day things, the customer service side, the experiences we can provide that I was learning so much about the world that the, the money I was getting for it, it didn't really matter too much to me. It was sort of felt almost like being at university. You know, when you're at university you're learning so much and obviously you're not paid for that. So it sort of felt like that in a way. After a year at that company, I then decided I wanted to take it to the next level. I wanted to go to a smaller company where I could develop my ideas more, I could have more of an input, I could start selling a lot more, I could be more creative. So I moved to the company that I'm at now and I have been here for nearly three years, which I.
Can'T believe it's been that long. I know.
It feels like you started yesterday. I know, it really does, doesn't it? The time just goes, it goes so quickly.
But when you were in those other companies that you hated, it felt like you were there for 30 years.
It felt like I was there for 30 years and it feels like I've been at my current company for six months. So, yeah, I moved to the company that I'm at now. And it made me realize so much that I've made the right move going into travel because my company was very small when we started. So, you know, I got to see what my CEO did every day, how she makes the company run, how my head of sales operated, how our marketing team got all of our clients, you know, all these amazing adverts and campaigns and everything that they do. So I got to see so much of that side and I got to be very creative with what I was selling. So I was able to put these amazing, you know, African safaris itineraries together. I was able to sell private yachts in French Polynesia. I was able to do so many amazing creative things and I just absolutely loved it. I wanted to learn about every corner of the world. I wanted people to discover these amazing destinations. I wanted people to, you know, go to Bali and have an authentic cooking class and home day with, you know, a family who lives there. I wanted people to be able to experience all of these things, but, but also be able to do it in a luxurious but ethical way, which is a very niche market because you want people to have these authentic experiences, but they still want to go on holiday and be pampered and treated well and be in a top five star hotel. So that's a lot of what I was doing. And yeah, so I've been doing that and selling for nearly three years now. So it's been amazing. And you know, to circle back round to the whole compensation and money aspect of it. Even though at the beginning of travel I did take a massive dip, which I needed to, to learn to, you know, do the groundwork. Now I make more money than I did when I was in the other industry, which I thought would make me a lot more money because, you know, now with what I'm doing, the money just comes with how well I'm doing. But when I'm selling to people, you know, on the phone, in face to meetings, it is so authentic and I truly believe in what we're selling in and I know these are the best experiences that they can have. So it's not forced. It's very simple. And I think a lot of people can see that, and clients can see that as well. So, yeah.
I am so proud of you. And, you know, I always say that, and I'm not just saying that because you're my sister, and I constantly send you messages, random messages. Jesse will get messages on a Wednesday, being like, just to let you know, I'm really proud of you.
No, I'm like, what have I done? Thank you.
Anyway, you know, sitting from the sidelines watching you in a job that you hated, that made you feel like every day when you came home and you were coming home and sleeping for minimal amount of hours and getting to the office early and, you know, not getting the recognition and, yes, getting the pay, but all of the other things that, as you said, you didn't really think were that important were really, really missing from those roles. And every time you would move job, and, you know, I've done a lot of this as well, but every time you would move job, I would think, okay, this one's gonna be different. And I truly was so invested, or.
Not even it's gonna be different. It has to be different, because this is your third move in three years. Like, it has to be different.
You have to stick with it, but.
You don't have to.
Which is what I learned. Absolutely. No, absolutely. And it's really interesting because if any of you listened to last week's podcast, it was the fact that I had four jobs in two years. And myself and Jesse are not too dissimilar in the sense that we've all always been driven by money. And I think we both sort of went on quite a similar journey where we both chased the money when we got out rather than chasing our passions. And it's really interesting, you know, we're approaching our 30th birthday in January.
No, I'm 28. I'm 28.
It's really interesting that we're sort of approaching it and we're both really living in alignment in what we're here to do. And it's so clear because, you know, I'm not saying that every day is sunshine and rainbows. You still have those stressful days where things go wrong, and, you know, clients and people are not doing things properly and things fall out. But it's really interesting to watch that. Approaching our 30th, it's taken us, you know, we graduated at 23. It's taken us sort of seven years to really start going through all of those experiences and really kind of aligning and really chasing not just the money and not just the kind of our ego speaking, but actually chasing our passions and being able to actually understand, you know, being able to turn those into our everyday reality. Absolutely. And it's really interesting to watch you kind of grow because whenever we talk about money, you don't know how much is coming in. You're not that person anymore that obsesses over what the paycheck is or if you work a few more hours, you'll get this. And it's been great to kind of watch your relationship grow. And you know, it was a hard time when you had to take that massive pay cut. But it's interesting now because as you said, kind of, you know, making those small little changes, you know, as you said, which aren't life changing things, but making those small changes, going for less dinners, you know, making sure that you're not sort of spending as much on clothing or whatever, you're now in a position a few years later where those things are things you don't even have to worry about anymore.
No, exactly.
Because you've allowed yourself to go, actually, I'm going to take that step back for a little bit. I'm going to realign, I'm going to have a look at what it is. I'm going to take a step back, things are going to change for a bit. But it was such a short amount of time that actually realistically, you've been at your company three years and you're making more money than you've ever made because you're, you took that step back, you took that leap, you trusted yourself. There was no one telling you this is definitely going to work. You took that leap and you took that trust.
So absolutely, it's really interesting to kind.
Of watch it come full circle and I guess it would be great for you to kind of share a little bit more about if anyone's kind of in that position where, you know, they're going, I'm in my third job, I fucking hate it. Is it my boss? Is it the company? What would be your sort of suggestions and guidance for someone who sat down maybe where you were a few years ago, thinking, I need to make change, but what the hell is my first step?
I think the first, the first thing you need to think about is how am I going to get there and what is the transition going to look like from what I'm doing now to that step. So let's say you want to do Something that you know, requires you to do something at almost an internship level. And you know what I did that you're earning X in salary and you need to take a massive pay cut.
Right. Okay, let's look.
What do I spend in six months? What can I get rid of? Okay, maybe I don't have to get my hair blow dried every, you know, once every two weeks. Maybe I can do it once a month or maybe I don't need to do, you know, I don't need to go to dinner four times a week, I can do it once a week and things like that. And you'll realize, you know, you'll look at your money and think, I can actually do this. Yes, I'm taking a pay cut. However, I'm also cutting things out my life, which doesn't mean I'm not going to do them anymore. I'm not going to not get my hair blow dried. I'm not going to not go out for dinner with friends. I'm just going to do it on, I'm just going to do it on a smaller scale and know that this is temporary.
Absolutely.
You know that things are temporary, but what's not temporary is your career and your passions and you know, what, you know, your self development. That's what you're going to be doing for the rest of your life. So, okay, you may get one year, maybe two or even three years with a lower base salary. Who cares? In four years time you'll be in a job that you absolutely love and you'll be able to, you know, compensate yourself well again. So it doesn't really matter. So I would definitely make sure you have a plan. I wouldn't do something like, you know, just quit and then feel I'm going to figure out, no, because then when you do that and just say, which I'm speaking for experience, I've done this. You know, you quit a job and say, I'll figure it out, I'll find something. A month goes by, you don't find anything. Two months goes by, you don't find anything. You need to make sure that you have a plan, plan in action. And then yeah, you can definitely do it. And it is weird to think about, you know, what am I passionate about and how can I make money out of that. But you can make money out of anything.
Yeah.
I mean, my boyfriend is passionate about football and he now works in the football industry. He did something similar to me. He worked in a couple of different industries before, which again he was getting paid very well for. But but that wasn't his passion. So he's changed industry as well. Which, you know, it is weird to look at something and think, right, I love it, but how, what, you know, what, what can it do for me? But there are so many different ideas, so don't be scared to try them and it doesn't matter, you know, if you're 25, 30, 35, 40, what you're, who relies on you, where you are, as long as you make sure, you know, you've got the minimum covered. Can I still pay my rent? Can I still, you know, afford food? Can I, you know, still afford to pay for all of those that depend on me? Then, you know, the world is your oyster. And then say you're in the situation where you can't afford, you know, to take that huge, that huge step and you can't actually afford to have a salary cut, then start doing stuff in your spare time. I know you feel like you'll want to have that work life balance which is very important. However, when you're doing things in your spare time, that is something that you're working towards a future work life balance and you're working on something that is a passion. So it won't even feel like work. Now when I, you know, work until 11pm and people say, oh my God, you're working till 11pm because it doesn't feel like work and I enjoy it, it's fine. So, and I, I do have a work life life balance in the sense that one day I'll work till 11pm, but then the next day I'll start at 11, then I'll have a lunch break at, you know, 1. So you do get a work life balance and it's not a traditional 9 to 5 or 9 to 6 job. So yeah, those would be, those would be my tips.
And it's really interesting that you kind of talk about, you know, removing certain things because look, you know, we all have those luxuries. Well, most, you know, we all have those luxuries in life, you know, getting our hair blow dried or doing our nails or whatever it is. And actually it can kind of go even further than that. I remember when I was first kind of saving for my home, you know, that was a massive passion of mine, you know, and passions don't always have to be about work, they can be about lots of other things. And when I was first saving for my home, obviously with my fiance, the home that we now live in, which was such a big project, I remember having to turn down dinners. I remember Having to, you know, even change the food shop that we did, where we were doing food shopping, we would kind of have to really, really budget on that. And it was things that, you know, we'd never really had to look at before. You know, we'd always sort of had a food budget and a budget for, you know, rent and sort of that sort of stuff. But it was really the first time that we sat down and sort of went, look, where is our money going? And for a short amount of time, it was for about six months, six to nine months, we sort of sat down and we went, right, if we stop spending this much, we can do this. And therefore, it was a big thing that we wanted to do. And same when I started my coaching business, you know, there was things that I really had to rein back on. And it wasn't even the luxuries I had to rein back on. It was very, very simple things like, like food, who our electricity provider was, you know, could we get it cheaper elsewhere? Could we actually, you know, start saving on food more? Instead of, you know, going out for dinner so much once a week, could we have friends over for dinner? And it wasn't coming from a place of lack or a place of scarcity and thinking, I'm not going to make money. It was coming from a place of going, I know I need to do this for six months because I have a vision, I have a plan, I know what I'm going to do.
You need to do this for your next step.
And that's the thing. And there's a really big difference of constantly living in fear about money and going, I'm not going to make enough money, therefore I need to save or going, actually, this is a plan that I'm going to do for six to nine months. It has an expiry date. And being able to have that internal conversation with yourself and say, this isn't coming from a place of lack, it's coming from a place of planning and action. And this is the next step I need to take to get to where I need to get to.
Exactly.
Yeah, absolutely. So talk me through where you're at in your career now. You know, how, where you kind of see yourself going, you know, all of the great things.
You're going to Kenya on Thursday. So, yes, I'm actually currently waiting for my negative PCR results. I keep refreshing my phone every five minutes because I think that's the anxiety of today's travel. Oh, my God. I have to wait for my test results. That's the, you know, that's the worst bit. That when you feel, you know, you've got those results, you're going to.
To go.
But yes, I'm going to Kenya on Thursday and I am so excited. As you know, my sister, myself, my mom, my dad, all of our family, we're massive animal lovers. And I've already warned all the people I'm going with, I'll be crying the whole time.
So just.
So just ignore me and don't take any notice of me. I mean, this time in three days, I will be feeding giraffes.
Oh, my God.
I can't even.
I've told Jessie that I'm gonna block her on Instagram, so I can't actually see her stories for the two weeks that she's away because I'll just be. We were meant to go for our 30th again. Here comes our 30th. But obviously with COVID and stuff, it's just, it's too stressful. But the point in that is.
Yes, Sorry, we went off topic there.
The point in that is three years ago, before you took this job, an all expenses work trip to Kenya, doing something that was just, you know, a trip beyond your wildest dreams, if I told you three years ago that your company would be supporting you to go on this amazing trip, to have paid two weeks off without the pressure, without the manager screaming down your ear to hit your targets, would you have thought that that was your life?
I mean, absolutely not. Because, you know, before I started travel, that's exactly what I thought careers were about. You know, you have your manager screaming down your phone, you have your CEO banging at your desk asking for, you know, when's your next deal coming? And things like that. And where I am now, I'm both. I absolutely love my company because they have, they trust me and I trust them and they've. That's actually very important in a workplace, trust. And I didn't really realize that until I was in my current company. Because if you want to be able to develop your own ideas, that trust has to be there. So that's one thing. Sorry again, that's slightly off topic, but just something I thought I'd mention. But where I am in my career. So a couple months ago, actually, I won an award. Yeah.
Again, proud sister.
There is a big travel online, well, not just online, gazette called TTG and I was named the UK's TTG adventure and Touring Agent of the Year, which I'm very happy about. So, yes, that was great. And you know, it is always good to be recognized for your work as well, especially from outsiders. I'm going on this trip to Kenya and I've also started a new sort of part of the business where I am. So it is still, still of course, doing what I'm doing in terms of selling these amazing trips. But it is slightly more personalized, it's slightly more higher level and it's catering a lot towards. I'm sort of taking my old industry and my new industry and combining them together in a way because I'm taking all the contacts that I met in my previous industry and trying to sell them, you know, my products from my current industry, which is actually very interesting because when I left my old industry I thought, bye, I'll close the door, never see you all again. But that's not actually the case, so. And I always thought, oh, there's three years of my life which is completely wasted, but they're not at all. So yeah, that is where I am in my career and it is at the very, very beginning. It is taking a lot of work, you know, from myself, my head of sales, my CEO, the product team, we are all working on it together, which is fantastic. So yeah, let's see where that goes. Let's see where that goes.
It's so cool to see using those three years to actually say they weren't a waste because I remember when you left, one of the things you said to me was, I'm really scared of leaving because I feel like I've wasted three years after university. And I think a lot of people stay, you know, whether it's in jobs or relationships or friendships or whatever it.
Is, we stay in them way past.
Their sell by day because we're worried of the time that we've invested in it. We almost feel like it's wasted time. But it's so amazing when you're in such a good place to be able to turn around and go. Those three years actually weren't wasted at all because I learned discipline, I got great contacts, I can understand how to sell to these high net worth people. I understand how these big companies work, you know, and really being able to use that to our advantage. And I really invite you to think about, you know, when you start criticizing yourself and saying, I shouldn't have done this, why did I do that? That was a waste of time. Try and sit down and really take out the good from it. Think about the experiences you take away. Think about the tangible things that you've been able to take out of that experience rather than just completely writing off 2, 3, 4, 5, 10 years of your life and saying, what a fucking waste. I never want to. I. I really wish I didn't do that. Being able to actually look at those. Thank yourself for investing that time and being able to say, like, this is what I got out of it.
Yeah, complete. I mean, every day in life, we learn something. And even, you know, if it's just a day where you're sitting at home in bed watching Netflix, let's say, and you start watching a new TV show, you go, oh, I'm actually really interested in, you know, science. Great. You've learned something new. You've learned that you're interested in science. Or it could be something massive on the other end as well. You know, for one day, oh, I've learned how to drive. But every day we're learning all these experiences and lessons. So just think about how much you've learned in a year. And that's not. Also, if you've spent a year in a job, it doesn't mean your whole life has been in that job. What about the things you learn outside? What about the things you've learned from the people you met in that career? You know, all of these things. So there's no such thing as time wasted. Even if you learn a lesson, even if something, you know, sad or bad happened, you've learned a lesson from that. I love that. One final question.
What is your dream destination?
Oh, my God. This is not fair. You can't ask me this. Can I name five?
Okay, I'll allow you. Five. Five. Okay, perfect.
Well, Kenya has always. Oh, I can't even put into words.
How excited I am. I just.
If you could see my face right now, my smile is from one ear to the other. 10, yell, I want to go to Japan. Just because the culture there is just. Just seems absolutely amazing. I mean, you can go skiing. You can see the snow monkeys. You can go into the futuristic Tokyo. You can go back in time and see the geishas in Kyoto. There's just so much to do there. It's modern, but it's also got a lot of past and history about it. So that is one place that I really want to go to as well. French Polynesia.
I knew that was coming. I knew that was coming next because we always, always talk about it.
We always talk about it.
Maybe for our 40th. Oh, God. Maybe for our 40th.
I mean, the wildlife there just looks incredible. You can go swimming, you know, all ethical. We're not talking about, you know, when you go into A cage and they're captured or anything like that. But you can go swimming with sharks and manta rays in their natural environment. If you see the colors of the lagoons there, they are absolutely, absolutely beautiful. The people there are meant to be some of the happiest people on Earth, which is always amazing. And it's just a place where everything lives on water. So, yeah, that's another place. Where else, I'm trying to think, where else do I want to go? Where else is on my bucket list? So, oh, Antarctica, Antarctica. I want to see the penguins, I want to see the whales. And, you know, you go on one of these amazing, amazing ships and you go past icebergs and you can go on helicopter safaris. It just looks absolutely. It just looks absolutely beautiful. And the other one I'm going to name is South Africa because you Cape Town just looks incredible with, you know, Table Mountain. You can see the penguins and Boulders Beach. And I'm a massive wine person as well. Not in the sense that, you know, I like to drink a cheap bottle of wine a night. No, I love these, you know, complex, bold, with lots of tannin wine.
If you don't understand wine, you're probably.
Thinking what she's talking about.
But.
And I want, I want to go to all the vineyards there, which just look amazing. And especially if you like, driving the garden route is just meant to be stunning. So, yes, those, those are my places.
So we better get booking all of those.
Yeah. And if any of you want to book anything, you know where to come.
Yeah, exactly. Well, Jesse, thank you so much. I mean, obviously being my twin sister, I'm so lucky that I get to talk to you about 100 times a day and constantly. Jesse will send me trips going, I want to go here, I want to go here. So it's really interesting and amazing to see, you know, see you grow up. Literally see you grow up from the wounds now and watch you just blossom into this person who is just so aligned with what they're meant to be doing, so into their work, so passionate and so passionate about, you know, not just the sales and the money, but actually really giving people these experiences and really, really, you know, booking these honeymoons and booking these once in a lifetime trips and just being there to, you know, help your clients in the best way possible. So thank you so much for coming on. I absolutely love you. You know how much I love you as my sister, as my best friend, and, yeah, I hope that you all enjoyed this week's podcast. And yes, if you ever need to book a luxury trip.
You know where to go.
Bye.
Thank you.
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