The Women in Travel Awards are back for 2026! In this piece we spoke to reigning entrepreneur of the year and CEO/Founder of Crooked Compass Lisa Pagotto. You can enter here.
When it comes to life, Lisa Pagotto is someone who clearly ticked the box for wanting adventure. Not only does her travel company, Crooked Compass, take travellers to some of the world’s most off-the-beaten-track destinations, but throughout her career she has consistently chosen the harder path, including pitching her business on Shark Tank.
In both travel and business, Pagotto has had to face the unknown, make big decisions on the fly and navigate uncertainty. So are the muscles required to manage the unknown in adventure the same ones needed to run a business?
Well, sort of, she explains.
“I would say it’s a similar muscle,” she says. “I would say that they complement each other, but I wouldn’t say that it’s exactly the same… I’d say it’s two muscles sitting next to each other that provides support to the joint.”
The difference, she says, comes down to mindset and setting.
“If you’re looking at it from a travel perspective, a lot of it is to do with your surroundings, in terms of how you’re interpreting things. You’ve got to act on the fly,” she says.
“Whereas when you’re in an office or a business capacity, you’re operating because there is an end goal… you’ve got a goal that you’re achieving, a sales target, a problem that you’re solving.”
Travel, by contrast, is driven by something less transactional.
“You’re not going over there to achieve a $5 million target, for example,” she says. “You’re going there for personal satisfaction, or for supporting another community, depending on what your reason for travel is, whereas business, it’s about the consumer, the client, and the team.”
Control what you can control
That distinction doesn’t mean the pressure is any less real when a crisis hits – and for Crooked Compass, that pressure has been tested directly.
When conflict escalated in the Middle East earlier this year, Pagotto says her instinct was to strip the problem back to basics.
“The first thing was always, what can we control? That’s always the first thing,” she says.
“There’s so much noise, whether it’s a family member who’s panicking because they don’t know where someone is that’s on a tour with us, or a travel agent that has got communications and they’re trying to get through to us… The first thing is always, what can we control, and we start from that.”
Some things, she says, are simply beyond her reach.
“Things that we have absolutely no control over, like rockets flying in the sky across the Middle East and across Dubai, we cannot do anything about that. Flights being cancelled, so far beyond our control, we cannot control that, but we can control, can you get on another airline?”
Pagotto says the same process applies whatever the emergency.
“It’s the same process, whether it’s an act of God, like an earthquake or a war, or whether it’s a change in a destination that we might have a touring operation in, through to, you know, last week we were doing a medivac of someone with a dislocated shoulder from Kazakhstan. It’s the same process.”
Despite the scale of the disruption, Crooked Compass came through largely unscathed when it came to cancellations.
“We’ve been impacted significantly, not in terms of cancellations from the Middle East, we were really lucky. We had one passenger cancel, and that was it,” she says.
The bigger impact, she says, has been on the pipeline.
“Up until mid July there was nothing new coming in the pipeline, and so new enquiry level has been incredibly low… since March, and that impacts our forward cash flow forecasting”.
Transparency as a leadership style
Running a small business, Pagotto says, has shaped how openly she communicates with her team – even when the news isn’t good.
“I’m very transparent with my team to the point where I will say to them, you know, we’re pausing our marketing costs for the next three months because of the impact of the Middle East. This is why.”
That transparency extends to her own mistakes.
“Everything we do is about transparency, just being completely honest, and if you mess up, put your hand up, let’s talk about it. Figure out the way forward as a team,” she says.
“If I make a massive error or do something stupid, I don’t try and cover it up. I tell the team… because I want them to know that I’m not perfect, and I make mistakes, and if I’m talking about them, I want them to feel comfortable to do the same.”
Recognising the edge before you fall off it
Pagotto is candid about the cost of pushing through instead of stopping – a lesson she says she has learned “the hard way multiple times.”
“Usually it’s my health that lets go,” she says.
These days, she pays closer attention to the warning signs.
“Things like if I start to feel that kind of burning in my chest, or the lump in my throat, or the butterflies in my stomach that aren’t normally there… When I start to feel that, I have to be the circuit breaker myself.”
Her advice for anyone starting out in the industry is to treat downtime as essential, not optional.
“Resilience is not about just continuing to push through, that is just insanity, and it will come at a cost, whether it’s your health or a relationship or something like that,” she says.
“I would say to use rest as a requirement, not as a reward. Don’t think once I get to the end of this, then I can take a break. No, that’s never going to work.”
For Pagotto, the real skill isn’t learning how to recover from burnout – it’s recognising the warning signs before reaching breaking point.
“It’s about recognising the edge before you fall off it.”
The Women in Travel Awards are back in a big way, with early entries and nominations running higher than ever.
This year’s theme, ‘Never Too Much’, is a call for women to embrace ambition, authenticity and the confidence to recognise their own impact.
The awards are open to women at every stage in their career and entry is completely free.
We’ve also introduced a shiny new nomination feature so that you can encourage an exceptional woman deserving of recognition. Those who have been nominated will still need to complete an application.
Enter/nominate here.
