The challenges and joys of balancing freelancing (and motherhood) in Southern Italy

Lecce: A City That Moves With Ease

Here in Lecce, people live the Baroque capital’s heritage as if it were a living entity: noble, enterprising families who owned businesses and employed locals, and whose acquired wealth was passed on from one generation to another, giving fruit even to its current descendants. This mindset can be felt on a daily basis: people are well-dressed, boutiques offer haute Italian fashion, apartments are grand, villas still stand in the city center, and daily life is easy to navigate. Time is a luxury. For an outsider, it’s quite contagious. However, if you want to live here, you need to balance this laid-back lifestyle with the demands of a freelancer’s obligations because Lecce does not have the vibe of a city. Co-working spaces are not a thing here, neither is settling into a cafe seat for hours on end, which is why home has become the office while the outside world is the place for client meetings. 

Essentially, Lecce today is where Milan was 30 years ago. And as one friend put it recently, Puglia today is where Israel was in the 1980s. You can imagine how much potential there is for growth. But the question is.. do they want that?

Understanding Where You Are

Initial Expectations

So when I first got here, I was eager to get started and explore a variety of beautiful locations from which I could work and Zoom with colleagues, friends, and family. There were so many young companies and new boutiques popping up, I was also eager to contribute and help them get their voice heard among the luxury traveler sector that was quickly picking up pace here. There has to be a way to communicate better. 

My first project started in 2019 when I decided to launch the very first, all-English travel and lifestyle magazine in Puglia, VIA Magazine. This platform was my way of showcasing the broad talents and ideas that were coming to life here in Puglia, from hospitality and gourmet food to olive oil production and sustainable fashion. There’s a lot going on if you take the time to study. This project opened a lot of doors for me, particularly in getting to know more people, making friends, understanding local culture, and the prospects for the region’s future in the coming five years. 

Regional Differences

Comparing Lecce (and Puglia) to the north, you can already see the gaps in lifestyle, investment, and technological progress. Differences bring about opportunities and challenges, however. The relaxed, traditional vibe of Lecce hints at the way locals tend to approach the work environment, and the field of marketing in particular. 

Seeing the level of websites, presentations, social media profiles, and communication strategies, I was quite sure that projects would be easy to on-board here. After all, I come with a lot of experience, international background, I speak multiple languages and am very good at adapting and navigating among different work environments and cultures.

One of the first things I learned is the power of ‘apparenza’ – which means appearance or facade – specifically that the way things look is often more important than the actual essence. Examples? From a work perspective, it doesn’t really matter if the website isn’t perfect, or the English is incorrect, or the reading material is outdated. People generally trust that if they do a good job, people will know about it by word of mouth – and Instagram. I often overhear people say “it’s good enough for now” and “it costs too much for results that will take a long time to see, if at all”. This is in sharp contrast to the calculated, fast-paced, strategic, tech-oriented environment of other cities like Milan, London, Tel Aviv, and Paris. Here, you either accept it or get frustrated by it.

Within this ‘apparenza’ is also a bit of laziness, I must confess; moving forward and doing things better requires time, money, human resources, and often times a new mindset. Who has time for all that? It’s lunch time now, the summer is around the corner, it’s almost Christmas already, the production is already done and needs to go out, finding the right talent is hard, and the way we’ve done it until now is fine enough to move forward.

What about technology? Local attitudes toward technology is still somewhat backward. Consider that there are no tech companies or a so-called tech valley around here, mostly manufacturers in stone, food, energy, and what remains of family-owned textile producers. I’ve often wondered why their communications platforms are so outdated but I suppose that between tending to the fields or mines, sorting products, taking orders, and shipping them out, digital communication is last on their list.

Where there are tech companies of various kinds, I’ve found that they tend to be very closed off to new ideas from foreigners and hiring them; they often cultivate a ‘locals first’ approach and even then, they are not always enthusiastic to partner amongst themselves. They tend to be apprehensive and wary of people’s intentions. People like to do their own thing and on their own. Don’t get me wrong; they will open doors to their homes, serve you like a king or queen at dinner, and help out whenever possible. However, looking from a freelancer’s perspective, things look different from this field of vision.

If you want to go fast, go alone. If you want to go far, go together.  Cory Booker

For example, you don’t know when the bus will arrive because there’s no digital screen telling you in how many minutes the next bus will make its appearance. What if the bus is stuck behind a tractor carrying hay or fresh vegetables from the field to the grocery? You simply have to wait. By the way, places like Lecce, Monopoli and Bari are real treats because in towns like Ostuni and Fasano there is no way to walk from the station to the town; you either wait for the bus, pray for a taxi, or risk it walking on the grass alongside the shoulder-less road. On the plus side, that makes time a real luxury here. There is simply no rush. Another example: many people still use payment machines for parking instead of a mobile app that lets you set the time and pay in under 60 seconds. Just the other day I caught sight of four people standing around such a machine in Monopoli, trying to understand how to put the money, insert the license plate, and activate the meter. Their were squinting their eyes, playing with change and talking amongst themselves; all this instead of opening the app on the phone already in their hand, swirling the timer, and marching off to explore the city.

Innovation is another challenge and not just in technology, but everyday life, too; as a new mother, I am constantly on the lookout for Gymborees and play spaces for my child. The only two places that I found are almost always empty – how can that be? There are babies born every day, waiting lists for nurseries, and kids pouring out of schools across town – where are all these people in the afternoons and on weekend mornings? After asking around, I discovered that locals are not open to the idea of ‘baby parking’, ‘baby sitting’ and similar concepts. They leave kids with the grandparents, family members, or take them along every place they go if needed. 

I’ve pondered this idea for two years now and while it’s always at the back of my mind, I am reluctant to make such a significant investment and have the only members there be my own child and some fiends. The idea is to create impact and offer services for families that improve quality of life (at affordable prices), allow parents to get back to work, time for mamas to enjoy an afternoon manicure after work, make weekends easier for everyone, and give children the freedom they need to roam, explore, play and practice with their sense of independence. I still wonder if this could work in other cities in Puglia, and my gut says yes but that requires partnership. It’s not something that can be done alone because looking at the current businesses I’ve seen, they are not sustainable. The point being, it’s not easy to build partnerships here but it’s not impossible either.

Speaking of which, I recently partnered with a great friend of ours, York Zucchi, who co-founded The 1583 Society that sells training courses to communities across the globe. We recently toyed with the idea of an interactive guide to Lecce for families because many people have asked ‘where can we take the kids?’; here is the result.

Become the asset. Arlan Hamilton

Observing Opportunities

Identifying Gaps:

Looking around, you can see there is so much potential and much to do to bring this region up to pace. If you have PR skills, negotiation skills, language skills, writing skills, sales skills and even labor skills (locals long abandoned that), you can find many opportunities to be part of something great and create impact in Puglia. 

Freelancing here has taught me that you need to be extra open-minded and creative in Puglia; sure you can take your clients with you from your hometown, but you also want the chance to collaborate with locals. Do be ready to knock on many doors before you get a ‘yes’, and learn to speak some Italian because most people do not speak English. Try to find projects that you hold close to heart and offer special collaboration fees so they can get to know you and your skills. 

If that doesn’t work, don’t fret. Keep the business going and remain open; the outlook is overall positive as things continue to change here. Each year more couples and families are choosing to relocate and start their lives in the ‘mezzogiorno’, the actual Mediterranean outpost. The real work is in the mindset and looking around, the high school graduates are the architects of the city’s future.

For me in particular, the state of digital presence leaves much to be desired. The average website, particularly in the hospitality sector, seems to be a copy-paste of a standard template just with different colours. Popular agencies do this unapologetically. In all honesty, I haven’t seen one great website. If you hop over to the respective Instagram profiles, things are even more worrying because it seems that literally anyone can be a digital manager nowadays. There are lots of content errors, distracting navigation experiences, and expressions written incorrectly.

It is my opinion that Puglia must be well prepared for the future and the region’s growth, opening minds to higher standards that support the development of industry, technology and tourism, and to establish basic best practices for the communication sector in particular. 

It’s hard not to want to change this broken mechanism and tap into the power creativity – this is not rocket science. Speaking of which, I’m on a mission to do some good chances and looking for clients who are open to change. 

Know someone who could benefit from this in 2025? Have them get in touch as I’m offering an exceptional offer to the first 3 clients who get in touch by 31 November 2024. Referrals get a commission – sharing is caring.

For the sake of avoiding spam, please get in touch with me via LinkedIn; I’m online every day and check my messages there.

Is there something I didn’t cover here that you’d like to hear more about? I’d love to provide insight. Get in touch!