Postcards From Positano

First of all, tell us a bit about yourself, what you do and how you got to where you are now?

I’m Caitlin, co-founder of lady-brains: a platform and top-rated podcast dedicated to helping early-stage female founders and their businesses grow, so they can live more fulfilling, meaningful and sustainable lives. 

I love helping people find the intersection between purpose and profit and we have recently started investing in early-stage start-ups and will soon be delivering entrepreneurship programs to high school girls in Australia.

My background is in marketing, media, and positive psychology, and in my mid 20’s I started a brand consulting and coaching business helping people in the workplace wellbeing and leadership space build successful businesses. 

I recently moved to Sydney from Melbourne, and you’ll find me sneaking in ocean swims whenever I can, watching the whales migrate up and down the coast, seeing the latest musical (huge musical theatre fan!), and checking out all the best bars and restaurants this city has to offer. 

We hear your recent travels were somewhat last minute. Tell us, how did this come about?

They were indeed! I booked a flight to Italy on a Friday afternoon and flew out the following Monday, giving myself just over 48 hours to pack!

Italy is a country I’ve been longing to visit (I’d previously only spent one night in Milan), and I had a small window of opportunity with planned time off from work, so I decided to spend almost three weeks there.

It was intense, magical and a great reminder to live in the moment.

How did you find the world and people's attitudes as it re-emerged post-lockdown?

Italy suffered significant loss because of the pandemic, and it was hard to watch that unfold from our corner of the world. I felt very fortunate to be visiting post-lockdown and to receive a warm welcome from the local people while sharing meals and conversations in their homes about what we all faced over the last couple of years. It was a poignant and cathartic moment for me.

While I was in Naples, I stumbled across a concert in a piazza that had been rescheduled due to the pandemic. Witnessing everyone singing together in unison and hugging and celebrating brought me to tears. It felt like a revival. They’ve been through so much and it was beautiful to watch.

So, tell us about your travels; where did you go? What did you do? Who did you meet?

I flew into Rome and spent four days exploring the city by foot, touring all the important historical sites, and catching up with family friends and meeting new ones. 

After Rome I made my way to Positano, via a quick stop in Naples. In Positano I celebrated the Italian national holiday Ferragosto. I just so happened to be in the right place to watch the fireworks show out on the water that night!

From Positano I headed down to Palermo, Sicily where I met up with friends and we cruised around the island for a week, staying at various towns including Trapani, Ragusa, Agrigento, Syracuse and finally making our way to beautiful Taormina for a few nights.

I capped the trip off with one final night in Rome, wandering the streets, visiting local artisans, and buying antiques and collectables for my trip home! Any unforgettable memories? 

The wonderful thing about taking a spontaneous trip with very little planned is you leave a lot up to chance. 

As well as stumbling across the concert in Naples, a few other unforgettable moments were learning how to cook Amatriciana from a Roman and sharing the meal overlooking Rome; watching the ballet at one of the world’s oldest open air theatres in Taormina; cruising around Taormina at night on the back of a red Vespa while watching a wild thunderstorm out at sea; sharing traditional dishes and local wines with new and old friends; watching the firework show in Positano, and finding the perfect cannoli just before I left Sicily which I indulged in on the plane back to Rome.

Every day I experienced awe and wonder, something that’s easy to cultivate when you’re coming from a place of gratitude (especially when you’re in Italy!).

Must see/do/eat recommendations

Eat: If you find yourself in Sicily you must try Couscous alla Trapanese – one of Sicily’s most famous dishes, and the local cuisine of Trapani – a beach town on the western coastline. This couscous dish is full of flavour and topped with seafood, and it did not disappoint. I am still dreaming about it. It pays to ask the locals what the area is well known for! 

See: Everyone knows the Trevi Fountain, and don’t get me wrong, it is beautiful, but it’s also very busy! On my last day in Rome, I stumbled across another beautiful Fountain called Fontana dell’Acqua Paola, it’s just across the river, and has fabulous views of the entire city.

Do: Hire a car and drive around Sicily hunting down the best beaches and swim spots! I particularly loved San Vito Lo Capo in Trapani and Tonnara di Scopello just west of Palermo. The Italians really know how to enjoy the beach life.

What were your must-have wardrobe essentials for an Italian summer?

Italian summer must-haves included lots of comfy and breathable pieces. I was on the go a fair bit and it was extremely hot when I was there, so I lived in oversized linen shirts, skirts, and a few cute dresses for the night-time.  

My INTACT pieces obviously came with me, and I loved wearing the long sleeve on the plane to keep me warm and my crop with linen pants in the evening. 

And of course, I kept some room in my luggage so I could bring a few special vintage pieces back from Italy, as well as shoes, I always manage to collect shoes when I’m overseas!

And now that you're back, what's planned for the rest of the year?

The next few months are full but exciting. I’ve recently been accepted into the Startmate First Believer’s program, which is a 14-week immersive program to learn all about early-stage angel investing. At lady-brains we’ve recently made our first investment in a founder duo, they’ve been long-time podcast listeners and lady-brains mentor program participants. I’m excited to learn more about this space with other angel investors.

At lady-brains we’re also developing an entrepreneurial program for year 10 girls to cultivate the entrepreneurial mindset and help them turn their idea for a product or service into a business. We’ll be delivering the pilot program early next year and I couldn’t be more exited to encourage and nurture our future founders and leaders.

I have a couple of weddings and small trips before the end of year which will be fun so bring on the longer days and warmer nights! 

Finally, how do you like to keep it INTACT?

I keep it intact by prioritising my wellbeing and creating healthy habits. I like to look at how I can distribute my time and energy across various life domains such as friends, family, work, health, and play. Depending on where I am at in my life or what needs attention will determine my activities, but I try to ensure I keep all the domains, or buckets, somewhat full! 

Every day I aim to savour moments that bring me joy and pleasure, and it’s often as simple as getting out into nature and soaking in the sun, swimming in the ocean, sipping tea while I work, lighting a candle, practicing yoga, or cleaning a space.

Caitlin Judd wears the Merino wool Signature Singlet in black.