“I ditched my draining city existence for a lifelong holiday in Italy: here’s how you can do it too”

Published in

Career Relaunch

6 min readApr 16, 2016

Jenni Midgley is one of the many British women who are quitting their jobs to carve out a new way of life while travelling the world. She tells Stylist.co.uk, how she plucked up the courage to break away from her Monday to Friday, 9am to 5pm, routine and how you can do it too.

“This year I left my job, turned off my alarm clock and boarded a one-way flight to Italy.

Before you picture me as a spontaneous tree-hugger, I’m not. There’s a good chance we’re actually very similar, you and I.

I’m a single 28-year old from Leicestershire who has spent the last seven years in London, first at Goldsmiths University, before bagging a job in the publishing industry and staying in the capital. Along the way I’ve made incredible friends who became a surrogate family. All of this was great. Just what I’d fought for.

But about a year ago, I spent some time in Croatia and came back with an overwhelming urge to make a change.

Jenni has the travel bug

I was tired. I loathed travelling to and from my office every day. I was sick of earning a fairly-decent wage and not getting to see much of it. I was also newly single (he dumped me before my trip to Croatia). Not having him as a reason to stick around acted as a great catalyst.

During those pivotal weeks since my return I forced myself to answer one question: “What don’t I want?”

My mental list looked something like this: I don’t want to spend eleven hours a day, five days a week at the job I’m in. I don’t want to await my weekends with such desperation that I attack them like a rabid dog and feel shattered on Mondays. And finally, I don’t want this weather. (S.A.D is real and true and I have it.)

With my Don’t Wants in place I spent winter 2014 in a full-throttle planning mode. I didn’t want a backpacking trip or an extended holiday. This time I wanted to make a life. Here’s how I did it.

Choosing a new place to call home

After spending my first four months travelling and exploring Italy, I decided to settle in Northern Italy’s Bologna. I read a lot about the it being a progressive, modern city with a lack of tourists (and it’s only 30 mins by train to the beach). I met a lot of Italians during my travels who compounded this by saying I’d love it. So it was a mix of gut-feeling, advice and research that led me to settle there.

But the key is to be flexible and not attach myself to any one place. Before landing an opportunity in Bologna, I’d worked stints in Rome, the Adriatic coast and the Sierra Nevada in Spain. I’ve since been offered part time work in a southern coastal city called Lecce and will be moving end of September.

Creating financial security

My biggest hurdle was money. I was earning £30k as the editor of an internal company magazine, but it was a huge burden to save on top of paying the bills. When my house contract expired in January, I asked friends if I could stay in their spare rooms. It’s amazing what happens when you can be humble enough to ask a person you love for something. I stayed with them for four months.

By the time the day of my one-way flight to Rome arrived, I had almost £4,000 in my pocket. That might not have taken me far in London, but in Italy it feels infinite. A month’s rent here in Bologna for my air conditioned apartment (sharing with one other) is approximately £240 and my weekly spend is usually about £100, rent and bills included.

The cost of food is also more reasonable in Italy. An amazing pizza in a restaurant in Bologna is about £4 to £5. For bread and fruit, I take lead from the locals and shop in local bakeries and grocery shops. I pay about 50p for a fresh loaf and 90p for a punnet of peaches. Bologna is the capital of food so you can eat out at some incredible restaurants and have change from a €20 note.

By a river in Tuscany

Earning an income while on holiday

The English language is not a barrier, it’s your commodity. You’d be amazed at how many jobs (especially seasonal) you can find to tide you over. I recommend getting a TEFL qualification, but I was able to get by with my studies on the English language and writing experience.

When looking for work, I started researching English-speaking schools or companies in Bologna and I also started thinking outside the box. For example, by asking a few locals I found out about an English educational theatre company who tour the country performing for children. I didn’t take the job in the end but it goes to show there are opportunities where you least expect it. They’re just a lot more well hidden than in the UK. Ask people you know for odd jobs and tell people you are looking. I learnt that Italy is less about websites, and more about chatter.

I’m able to earn between €800 to €1,200 a month and while the economy isn’t great in Italy at the moment, I don’t need much money to get by as I did in London. Currently I’m in Bologna before I start a part-time tutoring job in the south.

Jenni (right) on top of a mountain with a friend

Making friends in an unfamiliar place

One of my biggest fears I had to overcome was being alone. Leaving what was by all means a great life seemed mildly bonkers and a few people back home struggled with the concept. But I tried to separate the physical from the mental. I used social websites for expats such as InterNations and CouchSurfing and also learnt to say yes to any invitation I was offered. I never knew who was going to be there and I found that exciting. Hostels and flatmates are also great resources for meeting new people.

One tried and tested trick is asking people for help — sometimes I would ask for directions even if I didn’t need them. Italians are pretty forward and inquisitive, especially when you’re not in a tourist spot.

I’ve also made friends at galleries, parks and on the beach. I’ve found that men are often the first to chat, but I’ve made some good female friends too.

Loneliness hasn’t kicked in yet.

Jenni on one of her adventures

What about your career?

I like to think I can have a career and this new life of mine. The career bit requires a shift in mindset. The definition of success needs to be mine and mine alone. For example, I don’t care about earning £100k a year but, I do want to continue to work in my field. I have to believe that I can do that but also be happy to take on other nuggets of work as I explore how my lifestyle changes might limit or actually provide different opportunities.

The best part is I’m no longer the military clown who was juggling work and fun. I can enjoy each day properly, not just wish away days until I can relax and feel content on Saturdays. My time is now mine. Some days I travel, trek and explore. I never had that in London.”

Originally published at www.stylist.co.uk.