Creativity Under Pressure with Lisa Pagotto

Creativity through the lens of the founder of Crooked Compass & Key Note Speaker

"Creativity means when things just flow naturally."

Lisa Pagotto is the founder of Crooked Compass, an immersive travel company built around depth, cultural respect, and meaningful experiences. She grew the business into a multi-seven-figure venture featured on Shark Tank Australia. When global travel came to a standstill, Lisa rebuilt and expanded in unconventional ways — including earning clearance to land a light aircraft at Sydney Airport while commercial flights were grounded. Her work is shaped by firsthand experience navigating uncertainty, risk, and reinvention.

• LinkedIn: https://www.linkedin.com/in/lisa-pagotto/
• X: https://x.com/crookedcompass
• Instagram: https://www.instagram.com/lisapagotto_/
• Facebook: https://www.facebook.com/Crookedcompasstravel/
• YouTube: https://www.youtube.com/@CrookedCompass
• Website: https://www.crooked-compass.com/

Transcript

Mari 0:22

Welcome to the Sustaining Creativity Podcast. I'm your host, Mari Reesberg. Over the past several years, I've combined my degrees in acting and somatic psychology to share my sustaining creativity techniques with performers. And now I've decided to share it with a bigger audience that includes you. I believe we are all creative, and this podcast is all about that. I'll be interviewing people from all backgrounds, ages, and creativity experiences to share just how creative we all are. Today I'll be chatting with Lisa Pagato, founder of Crooked Compass and Keynote Speaker. Please enjoy Lisa Pogato. Welcome to the Sustaining Creativity Podcast. Today I'm chatting with Lisa Pogato, founder of Crooked Compass. Welcome to the podcast.

SPEAKER_01 1:15

Hi Mari, how are you? Thank you for having me.

Mari 1:18

I am well. Thank you so much for joining me. I am super excited to chat about creativity. And as I blazed through my introduction, I realized I totally forgot that you are also a keynote speaker, as well as the founder of a company and business. So wanted to make sure I got that. Before we jump into our creativity conversation, why don't you share a little bit more about who you are and what it is you do?

SPEAKER_01 1:48

Sure. So I work in the travel and tourism industry. I have two touring brands that I have developed and created. One of them is called Crooked Compass, and that is your small group tours and private tours, really focusing on your more emerging, sometimes stigmatized, sometimes a little bit controversial destinations, sometimes quite frontier in terms of lack of infrastructure, places where you definitely need creativity and all on all sorts of levels. But very much for people who are very well traveled, looking for that. What's new, what's next, very curious-minded, very highly educated, and they're looking for that, that stimulus and that education to come from their travel experiences. So I've been running that business for 12 years. And then during the pandemic, when that business couldn't trade because our borders were closed, I launched a second business which was called, well, which is called Crooked Compass by Air. And that is predominantly Americans coming to Australia, exploring our amazing country by private plane and helicopter to reach the most remote reaches, uh, remote and exclusive cattle stays, uh, cattle station stays, luxury lodges, those sorts of things. So I have those two, and then on top of that, I do um a fair bit of speaking, focusing mostly on leadership and entrepreneurship, about you know, backing yourself when there is no proof. Um, the evolution that comes with who you are is not who you are at the end of the journey, and all of the hurdles that come in between, they always come back to alignment and integrity.

Mari 3:21

My goodness, you sound very busy. Unbusy though. And it sounds like you love this work and it's such a calling for you. How did you get into the luxury tourism and travel pieces as well as kind of the more remote I maybe extreme isn't the correct term for it, but they sound more extreme than the luxury pieces.

SPEAKER_01 3:51

Yes, yes. So um I I've been in the travel industry since I left school. I I went to a private travel college and after that was straight into the workforce. And so 24 years I've been in the travel and tourism sector, and I've had my business for 12 of those years. And in terms of how it came about, there was just this opportunity. So for me, when I was in my early 20s and I did the gap year overseas and went traveling, I just wasn't interested in what everybody else was doing. I wasn't interested in drinking my way through the UK and through Germany. I had grown up with the most incredible grandmother, and she taught English in North Africa, and I wanted to see where she taught. I wanted to meet the families who she taught their children English. And so I went to Tunisia in North Africa, and that was my first glimpse of wow, there is a whole nother world out there that is not Western Europe. Um, that is just so fascinating. And if this tiny little country can deliver this, what else is out there? And so I've always been drawn to the lesser known, going to places where the mass market are not, and always just had this craving and this curiosity for what is next? Now that I've spent two months in Africa, what is next? Now that I've spent a month in India, what is next? And I've just always kept searching and searching. And it got to a point in my career where there was nobody in the Australian market that delivered travel the way that I wanted to, unless you were a backpacker. And I was past that point and I wanted to do it more comfortably. And it was a bit of a blue ocean. So I started with six small group tours and now we have over 100.

Mari 5:34

Oh my goodness. Wow. Wow. I I can appreciate I too grew up traveling in I feel similar ways. It was always kind of steeped in the culture of the location that we were going. We were not staying in the big hotels or things like that. It was very much uh trying to immerse ourselves into the community uh that we were visiting and learning about as I traveled as a child and as an adult. So I really appreciate that. When you think of creativity, what does it mean to you to be creative?

SPEAKER_01 6:13

So for me, in terms of what it means, it's when things just flow naturally. That's probably it in its most simplistic terms. And as you said at the beginning of our chat, that my world is very busy. And so for me, creativity, I have to carve the time to allow it. It can't happen when I'm being pulled in every direction and I'm doing all of the things. But when I, for example, jump on a plane and no one can contact me and I am completely offline, my brain, my creativity just goes. And so for me, creativity is about making the time to allow things just to happen and to flow. They are things that for me deliver a response of excitement, um, of achievement in some sense, but also opportunity. Um, and they don't necessarily have to make sense. It might just be me writing down a few words of things that are just coming to my head, and at some point they'll all come together to create something. Um, but it will look different for everybody. For me, with what we create in different countries, creativity is finding experiences that are outside the box, creating things that don't exist and seeing how we can build them. Um, and then personally, for me, a lot of my creativity is done through reflective writing.

Mari 7:34

Nice. Yeah, the kind of the contrast of the action part of creativity and generating and creating an actual thing versus not that reflective writing isn't creating a thing, but has more of a uh it feels a little quieter to me when you're talking about it. What are some of the creative pieces that you've had to employ with the traveling? If infrastructure isn't available, how how do you go about navigating that?

SPEAKER_01 8:09

Yeah, I mean, there's so many different layers to answering that question. If infrastructure's not there, it might be something as simple as we might need to camp for a few nights and making sure we then come back to that creature comfort that our guests are expecting. But if you want to go and see this remote tribe that are five days away from civilization, that's what we have to do. And on the other hand, with creativity where we operate, getting creative when things go wrong. Um, that's a big part of it too, because nothing follows a textbook when you're in the middle of nowhere. Uh, you have to be able to think on the fly and you have to be able to think under pressure, and you have to use every corner of your brain and the team that are with you to be able to find the best possible solution. And sometimes it's really random ones, like putting someone with a dislocated shoulder on the back of a reindeer to get to the nearest medical place because you can't get a helicopter in because the range isn't long enough, type of thing. So there's always innovation and creativity every single day in the business, even you know, at the desk, coming up with better processes that are more engaging for our guests, that are more beautiful for our guests. Um, yeah, every every touch point of our business has its own different style of creativity.

Mari 9:22

Absolutely. It sounds like you're speaking from experience, putting someone on a reindeer.

SPEAKER_01 9:28

Traveling. Like all sorts of creative evacuation stories. There are many.

Mari 9:34

I can only imagine, yes. And I guess I have curiosity for your own travel. What are some of the ways that you had to get really creative to navigate challenges or unexpected things when they pop up?

SPEAKER_01 9:51

Yeah, well, it's interesting. You mentioned earlier extreme travel. And whilst we don't do extreme travel within my business, I personally do extreme travel outside of my business. That's my thing. The pictures on the wall behind me here are from some of the most extreme destinations that I've been to. Um, and that's places like Yemen, Lebanon, South Sudan, those sorts of countries. Um, in terms of getting creative in those places, yes, that is a whole nother level. Um, and that is not for anybody to just go and, you know, some people would say I'm crazy for going to those destinations. Um, but you end up getting a bit of an edge about how to deal with things when things go very, very wrong. And in a lot of those destinations, there have been some quite serious situations where sometimes there is literally nothing you can do except be calm. Um, and that is creative in itself because it has to be forced. When you are on a bus and someone comes on with a gun, and you just have to be calm and you know that there's someone on the bus that's going to act like a fool because of the pressure. And you have to play your part and you have to choose how you behave in that situation. Or I've had another situation where I was trying to leave a country and they said to me, literally, as I'm being stamped out through immigration, your visa's not valid. And I said, Well, I've I've been here for 10 days, you stamped me in on this visa, look at the dates on it. No, no, it's not valid. I knew what they wanted. I've been around long enough to know that they want money. Um, my passport was taken off me. I was taken into a room, I was put in a room with a very intimidating man. I've, you know, for a first-time traveler to these destinations, absolutely terrifying. But when I actively choose to travel to these places, you become conditioned and you understand that people generally want money or power. And um, for me, I knew straight away this situation was money and I was not going to give it over. I I went into this room, he threatened, he said his things, he left me there for an hour. I was like, I'm gonna miss my flight. He came back, he got nowhere, my passport was thrown at my face, and I was sent through and I got on the plane. Um there's yeah, that there's so many different things where you have to be able to switch between different levels of creativity, and it means different things to different people. Like creativity is not just about being able to paint or being able to make a candle. Um, it is about being able to adapt, it is about being able to think on your feet, and it can be taken in so many different forms depending on you know your world and and and what you need to be able to be creative in. And um yeah, it's it's just something I I find it truly fascinating. Creativity is just one of those things where immediate thought is pretty things, but then there's the extreme side, and creativity under pressure is a whole nother level of being creative.

Mari 12:50

Absolutely. I can appreciate you bringing the just the levels of creativity and how each of them requires very different versions of it and creativity under pressure, how we react or respond to situations that we find ourselves in. I think I'm equating this also to like being on stage and having something go horribly wrong, and we have to get out of the situation with an audience as well. But yeah, some real life and death situations that you're talking about, and how creativity can really support you in those moments if you're willing to tap into it. Because I think oftentimes we go into that fight or flight space, and it creativity doesn't often happen in fight or flight.

SPEAKER_01 13:48

So no, no, it doesn't. And and I think that that that's one of the big skills of learning when you are in fight or flight, recognizing which one you're in, um, and then working out what can I control, how do how do I bring that nervous system down? Because me being in either of those is not going to be helpful.

Mari 14:10

Exactly, exactly. So really getting that nervous system safety back on board to be able to make a different choice or respond in a different way. Yeah. Well, you I mean, the amount of traveling you have done, the extreme traveling that you choose to do. I'm so curious in your life today, who or what inspires you?

SPEAKER_01 14:35

Oh I yeah, in terms of who inspires me, I guess it depends on which which part of my brain you're talking to. If it's if it's from like a business sense, there's the people that inspire me are like an Oprah, for example, someone who just pushes through, doesn't give a shit, and just makes things happen. There's that side. Then, you know, here within Australia, there's one of our politicians who was completely thrown under the bus during the pandemic, but she was an incredible leader and she just did not budge on what she truly believed in. And so I, you know, I love seeing that. But then I look at people who are more in that exploration space, who do like these hardcore expeditions from the geographical North Pole to the South Pole by kayak and bicycle and foot, and I'm like, wow, this is incredible. So depending on which layer of my world we're talking to, that there's different people sitting in each of those areas. But generally, people that the common thread is people who just back themselves.

Mari 15:41

Yeah. And what is it about people who back themselves that generates inspiration for you? People that back themselves, they they're not crippled with excuses.

SPEAKER_01 15:54

They just make the thing happen. And you know, that that's a big thing that I often talk about is encouraging people to believe that they can do the thing that they think that they can't. And the people that I aspire to or that are inspiring to me have done that. They've backed themselves, they don't listen to the other voices, they just truly believe in what they do. They have this incredible passion, which is what drives them. And they just stick with this integrity and this alignment. And if it doesn't fit within how I want to feel and how I want to progress, then there's no space for it. And that discipline is, yeah, it's something that's so incredibly powerful and something that's very difficult to train into yourself. I was just about to say that.

Mari 16:38

Powerful and very difficult to those who master it are the ones that truly succeed. Absolutely. When you know, when those voices, the other voices show up for you, how do you kind of clear the path to keep yourself to keep you moving forward in that backing yourself experience?

SPEAKER_01 17:04

Yeah, well, this is where a lot of my writing comes in. When I get those voices, I write. I'm like, I need to stop because this is happening and I'm not liking what I'm hearing. It's kind of trying to derail me, it's making me confused. Now I'm not sure if I'm making the right call. I need to stop it. Um, and we all know what it's like when you have that monkey brain and you just get caught and you keep going in circles and circles and circles. For me to break that cycle, I have to write it down. And I have to just leave it. The sleep test is another thing, just leave it and come back and review it the next day with a fresh brain, with fresh eyes. Um, or depending on what it is, bring in another perspective. Um, that that is my way of trying to break that cycle of being stuck and swamped by those external voices because we all have them, no matter no matter how much work you do or how much you sort of condition yourself to be able to squash those, they are always still there. And there's always something that someone will say, even if you're the type of person that really isn't swayed by what people think, there will still always be something that gets in. And yeah, it takes a reset to be able to um squash it, get back on top of it, and just go, hang on a minute. No, this was a jealous reaction from somebody, or hang on, they don't truly understand my business. That's a very logical answer, which doesn't fit with where I'm going with this. And you just need that time. And for me, writing, doing the sleep test, and then coming back is is my way of working through that.

Mari 18:33

Nice. It sounds like you've you use it and successfully use that in the in eventually we get there.

SPEAKER_01 18:41

Not all the time, it's not not as quick in black and white every single time. Sometimes it is. Um but yeah, it's it's a process and depends on how heavy or how big the thing is. If it's like a staffing problem, obviously that's a longer period to process something. If it's something really short, like you got an abusive email from an unhappy client, that's very different.

Mari 19:02

Right. So, yeah. To discern which piece or part you're actually needing to navigate. Yeah, and yeah.

SPEAKER_01 19:11

And also, how much time do you want to spend on this? How much energy do you want it to suck from you? Is this something that you want to drag on for a week? If not, okay, we need to we need to work through this.

Mari 19:23

Yeah. So as I mean, it it sounds like if you're running a hundred trips a year or a year, I'm assuming a year, the number of people that involves and personalities and navigating all of that together, how how does creativity show up when you're crafting these trips and getting the people together to lead them or you know, the support staff and all of that?

SPEAKER_01 19:54

Yeah, well, I guess there's there's two sides to it. There's the the building process and the execution process are the pretty creative sides, the fun bits where you're pulling it all together and then obviously having it executed and delivered on the ground with your guests. That's the beautiful creative side where you know we are delivering what we've been promoting and bringing it to life for our guests with a lot of storytelling from our guests, uh, from our guides. That's something that we push very, very heavily is storytelling, which brings, you know, we don't want someone regurgitating a textbook to our clients. We want them to talk about what life was like for them under the Soviet Union, for example, what they experienced when they had to go and live in a sanatorium for 15 years. We want those stories to bring it to life, and that's the creativity on the client-facing side. On the internal side, um, it's probably not so much creativity, but a structured process um around expectations. And it is literally it's process, it's it's not pretty, it's not um fluid, it is black and white. So there's the two sides.

Mari 20:58

Yeah. I have so many questions about the tour guides who are spending 15 years in a sanatorium and under Soviet rule and all of that, but I feel like that's another podcast for you in your kind of travels and your own creative experience of the world and creative expression. What are some of the things that you are dreaming about, are wanting to have more of in your own life? And how do you what are those steps that you take to achieve that?

SPEAKER_01 21:36

Yeah, sure. So for me, I'm just forever curious. I'm always looking for that what's new and what's next, just like our clients, but probably at a more extreme level because I want to be able to find and create and deliver something truly special for them and also for myself. Because of course, you know, every time we we operate one of our tours and we know that it's something that's perspective shifting or life alternative. Or something for our guests. Like that's an incredible feeling to know that we have created something that nobody else is offering. So for me personally, it's that constant hunger, that constant curiosity searching. For me, one of my big passions is using travel as a way to support fading cultures and diminishing tribes. So I am constantly searching for those groups and understanding what support we can provide that is not going to be negative to them from a tourism perspective, but that can only help them in terms of retaining their culture, preserving that culture, as opposed to it's too difficult to be a hunter-gatherer that lives in the mountains, everybody's slowly making their way to live in the cities. Like we really want to find our part to play to preserve that. And that's my favorite thing about what we do when we build our tours is finding those little pieces and knowing that we make a difference. So I can give you a couple of examples to put that context into practice. So in um Mongolia, which is one of our destinations, there is a fading culture and diminishing tribe that only has 200 people left in it in the very north of the country. These are the guys with the reindeers that I mentioned earlier. Um and they are very different to the rest of Mongolia. They are nomadic, but they don't live in ghers like what you commonly think of. They live in teepees. Um, and they travel with their reindeers. Their reindeers are their mode of transport. Their reindeers provide milk for them to make cream and yogurts and those sorts of things. But what they live off is they forage. So they live off berries and nuts and tubers that they find in the forest. And so the number one thing that is um killing this tribe is septicemia from gum infections, from cracking nuts and cracking branches and things like that. And so we work very closely with the Australian Dental Association to send over outside of our Turing product, but to send over 12 dentists every year to provide proper medication, to provide um hygiene education, which is very difficult when you don't have access to, you know, running water. They've got river water or melting glaciers. Um, but just to be able to play our part in knowing that we are trying to make a difference in the number one thing that is causing this tribe to shrink. Um, and that's one of the reasons that we have the permit access to be able to visit them. Um, and same thing, when our groups go there, from a consumer or a guest perspective, you're not allowed to bring in lollies and plastic and things like that for the toy, for the children. You bring in second-hand clothes and shoes and things like that that will make a difference so that they don't have to come into the city, they can stay out in the middle of absolutely nowhere. You know, these guys are five days by road from civilization. Um, and there are no roads to reach them. Like you trailblaze through nothing and then jump on horseback because the cars can't go through the forest. So that that's one example where when I was constructing that tour, so that was probably 10 years ago that I built our first tour out there, that creativity project was just incredibly rewarding as each piece slowly fell into place. It was very hard. There was a lot of red tape, but that's kind of the basis of what we try and look for in everything that we operate.

Mari 25:20

Yeah. How long does it take for a tour like that to actually go from inception to participation?

SPEAKER_01 25:31

So something like that with that level of um complexity, two and a half years to build, something that's much more simple that doesn't involve fragile cultures that might be in a little bit like going to northern Peru, for example. Um two months.

Mari 25:50

Okay. Yeah. So just like understanding the time and how much creativity goes into two months versus two years.

SPEAKER_02 26:03

Yes, exactly.

SPEAKER_01 26:04

And the the two years is generally to do with red tape and permits and process, and there's a lot of waiting where nothing's happening. Um but yeah, we I would say maybe 25% of our tours sit in that category, that extreme build. Um, and they're probably our best sellers if I was to look at it that way, because people want to know that they're making a difference. Sure. Um, and we do share that story of we haven't just thrown this together with Chat GPT, here's a pretty itinerary. Like that there is a real story behind this, and there is a real intent as to why we have built this. And people respond to that because everybody loves to feel like that they're making making a difference and they're making a conscious choice um for the positive.

Mari 26:52

Absolutely. Well, for individuals who are looking to I I I guess this is a two-part question. Individuals looking to get into the tourism and travel industry, what are some things that you would uh advise them to do if if someone just were beginning this journey?

SPEAKER_01 27:14

Um travel and tourism is definitely a passion industry. It is not, you're not going to become filthy rich by working in travel and tourism, but you can make a difference. So if you see the travel industry and go, I want free travel and I want to get paid to travel, don't join it. Go and try and become an influencer or something because that's not what it is. It used to be that, but it's not that anymore. Things have evolved so much, especially with AI and with influencers. It's it's just and and budgets have changed since the pandemic and now that the current situation that we're in, the travel industry does not have the cash that it used to. Um, and so for people who are joining the industry, you have to be truly passionate about travel. You have to be truly passionate about education, but beyond it just being for yourself, it has to be a passion for you wanting to use travel as a force for good to educate other people who would be your clients and showing them that there is something that is so fragile and so precious that's out there beyond just big Western five-star resorts. I mean, it really depends what your interest is in travel. If you love luxury, sure, you can go and be a luxury travel agent and you can sell all the beautiful lodges and all the luxury boutique hotels and that's fine. That's very easy. It's quite transactional. But if it's more of a um deeper personal, I want to feel like I'm shifting something for somebody else, then that's where you move into the deeper side of the product scope of the industry, where you can create product, where you can't, you're not just selling out of a brochure, you are literally building it for your client.

Mari 28:57

Absolutely. And then for individuals who are just dipping their toes into being a guest in a travel industry space such as yours, what advice do you have for them looking at the tours you offer or and how to pick pick something?

SPEAKER_01 29:16

How to pick, yes. I mean, it really comes down to value and what value means to the client. If they're about price, they certainly won't come across us. If they are about wanting to do things that are truly immersive and that are off truly off the beaten track, not cliche off the beaten track, then it's really about analyzing. You know, you'll come up with a couple of different companies and find those tours that may be to the same destination, but the itineraries will have their own nuances and really picking them apart and asking the questions. One of the big things that we see with our product is that it is so high touch. We don't get people that just go, yep, 10th of June book. They don't do that, they ask a lot of questions beforehand because they're researching and they're wanting to make a considered choice. So it's about getting that nitty-gritty detail on a surface level. If you just kind of skim a website or flip through a brochure, you'll see a certain level. But if you are really wanting a certain type of experience, I would encourage people to speak to that operator and to ask the questions to make sure that what they're going to put their money down towards is really going to deliver what their outcome is that they want to achieve as a traveler.

Mari 30:25

Absolutely. Those are great, great pieces of advice for anyone traveling. Doesn't matter which what version of it, but important to ask all those questions. Absolutely. Yeah. Well, Lisa, this has been such a treat getting to chat with you. I have one last question. What does it feel like in your body to be creative?

SPEAKER_01 30:48

Oh, it feels light. And it feels just happy and just it's like there's no wait. When you're being creative, and well, for me, when I'm in that creative zone, there is no, oh my god, this has got to happen. I've got to process payroll, I've got to get this deadline done, I've got to be at school pickup. None of that is there. When when I am in my creative zone, there are no distractions. The phone is on flight mode, the notifications on the laptop are off, or my sound is on mute. And I am just in that creative zone because I need that flow. And so not having the distractions for me, that's elating. If I could not have a mobile phone, that would be incredible. Um, but for me, it's just that lightness and that freedom of letting things come and scribbling things down and then seeing how they'll piece together and what could this become? It's a it's that curiosity. For me, everything always comes down to curiosity, but just having that space to allow it is is very uplifting.

Mari 31:51

Yeah, it's beautiful. I, as you're talking, can feel the lightness and the weight, like no weight of what you're saying and recognize that as well. Well, thank you so much for joining me today. If people want to learn more about the work you do, the tours you offer, all of the things you have out in the world, how could they go about doing that?

SPEAKER_01 32:11

Yeah, of course. So for our crooked compass, so that's our international travel product, the ones that are to your more emerging destinations. That is um www.crookedompass.com. Um, for anybody who's keen to explore Australia by private air, that's crookedcompassbyair.com. And if anybody's looking for a speaker around any of what we've spoken about, it's LisaPagotto.com.

Mari 32:37

Perfect. Well, I will put links in show notes so people have very easy access. And thank you so much for taking the time to join me. This has been such an eye-opening and wonderful conversation. Thanks for having me. Thanks for listening to the Sustaining Creativity Podcast. We'd love to keep in touch, so follow us on Facebook and Instagram. We are at Sustaining Creativity. Make sure to subscribe to the podcast wherever you listen to podcasts. Tag your friends and family so they can listen too. We'd love to hear from you, so leave your reviews, comments, and questions. Check out our website, sustainingcreativity.com, for upcoming offerings and creativity coaching. Tune in Tuesdays for our next episode. And remember, with creativity, anything is possible.