The Squiggly Career: Five Women on Choosing a Different Path and Redefining Success

There was a time when careers followed a predictable path: choose a profession, stick with it and retire decades later. But for many women, working life now looks far more fluid, shaped by creativity, caring responsibilities and the desire to build something that better fits their lives.

The idea of the ‘squiggly career’ has become increasingly familiar, with more people changing direction multiple times throughout their working lives. Sometimes that shift is sparked by burnout or family life. Sometimes it’s driven by curiosity or simply the feeling that there might be something more.

We asked five inspiring women to share how their career paths evolved, from mental health nursing to media, finance to fiction, teaching to surfing, accountancy to travel and corporate life to fine art. Their stories are very different, but all offer a reminder that careers don’t always have to follow a straight line.

 

 

Tracey Thomson

Tracey is Co-Founder of The List and Author of multiple children's books. With career chapters spanning mental health nursing, finance and community work, she is passionate about writing and embracing new opportunities at every stage of life.

Tracey believes some of the best opportunities come from changing direction. 

“My professional life has taken quite a few twists and turns, leading me to where I am now as Co-Founder of The List. Even now, that’s only part of what I do. I write children’s books, I’m currently writing a novel and I’ve been involved with local mental health and children’s panels for many years, only recently stepping back from the latter after almost a decade.  

I’ve always admired people who seem to know exactly what they want to do from a young age. I was never one of those people. Even in my fifties, I still feel like I’m figuring things out and enjoying the journey as I go.

I dropped out of university in my second year because I simply wasn’t enjoying it and couldn’t see the path ahead clearly. Instead, I trained as a mental health nurse, which many people thought was reckless at the time, but I loved it. I worked in healthcare in Scotland, Germany and Guernsey, and those years shaped who I am today. The work could be incredibly challenging, but it gave me perspective, resilience and lifelong friendships.

Later, I made another big career shift into finance. Guernsey offered opportunities and I had a strong academic foundation and a willingness to learn. I started at the bottom and worked my way up to Board level while also raising a family. One of the best parts of that chapter was having a supportive boss who recognised my work ethic and gave me the flexibility to work part-time. 

Eventually, changing family circumstances and caring responsibilities led me to step away from finance and rethink what I wanted work and life to look like. That period also made me reflect on my identity and purpose, drawing me towards children’s and mental health panel work and reigniting my love of writing and books, which is how I met my co-founder Stef. Over a walk and a glass of wine, The List was born.

My advice? Don’t worry if your career path doesn’t look straightforward. Some of the best opportunities come from being willing to take a chance and say yes to something unexpected.”

 

Image credit: Paul Chambers

Ruth Thomason

Ruth Thomason writes historical fiction under the pen name RJ Verity. After more than two decades working in financial services across Asia, she rediscovered a passion for creativity and is now author of The Poole Legacy series, as well as an organiser for the Guernsey Literary Festival.

Ruth’s advice? Start messy and keep going. 

“For over twenty years, I worked in financial services across Asia - a career that kept my left brain very busy. While I enjoyed reading fiction in my spare time, creative writing wasn't on my radar at all. Then I attended a leadership course where we explored art and literature as a way to unlock our creative minds, and something shifted. I started writing purely for pleasure, with no expectations.

Around the same time, I became increasingly drawn to questions of ancestry, memory and identity – who we are and what shaped us. That curiosity, combined with the discovery of fragments of my own family history, became the seed of my first historical novel, Poole of Light.

The first draft was pretty awful. But rather than give up, I invested in creative writing courses, joined a writing group, and learned the craft properly. I now write as RJ Verity, and my debut series, The Poole Legacy, is out now.  I’m also an organiser for the Guernsey Literary Festival, which means I can combine some of my business skills with my love of all things writerly - it’s the best of both worlds.

My advice: If something you've always loved keeps nudging at you, take it seriously. Start messy, find your people, and keep going. Don't wait for the "right moment" – it rarely arrives.”

 

 

Christina Stagg 

Christina Stagg is a Guernsey-based artist whose career has spanned both corporate finance and fine art. She now paints full-time using traditional old master techniques and materials. View her work at The Immortal Divine Exhibition.

Christina encourages you to embrace your passions and seize opportunities.

“I’ve always believed that life happens in epochs. Twenty years, twenty years, twenty years.

As a young person, I dreamed of following an arts career, but at the time I simply didn’t have the resources to fund such a precarious and uncertain path. Even so, I never gave up on the idea. I always felt that one day I would return to it, even if I had to wait until my 50s.

After graduating from Exeter University with two law degrees, I spent a gap year in Tokyo, where I studied painting part-time at a Japanese art academy. Back in London, I self-funded a foundation course at Wimbledon School of Art, where I won the drawing prize. I then studied Renaissance painting techniques under artist David Cranswick while also working for Bonhams in Bond Street as an assistant fine art valuer.

At 27, I moved to Guernsey and began what became a 30-year career in corporate finance, specialising in legal, compliance and regulation roles with firms including Generali and BDO. I genuinely enjoyed the intellectual challenge of navigating the legal and regulatory landscape, particularly the complexities of financial crime.

After the Moneyval evaluation at the end of 2024, I decided to leave the finance industry on a career high and finally pursue my second career full-time. I was also offered a position as a NED on the board of the Guernsey Arts Commission, which introduced me even further to the island’s flourishing arts scene.

Today, my painting practice is rooted in old master methods and techniques, drawing on medieval materials such as egg tempera on gesso panels.

My advice? Life takes unexpected twists and turns. Be brave, embrace your passions and seize the day.”

 

Fiona Sarre

Fiona Sarre is a travel consultant and franchise owner with Travel Counsellors. After years working in accountancy, she finally took the leap into travel, building a flexible business that fits around family life and her love of exploring the world.

For Fiona, the biggest risk is waiting too long to make the change.

“When I left school, I trained to be an accountant because, honestly, I didn’t really know what I wanted to do. I just knew I wanted a qualification and a decent salary. Four years later I qualified, worked in London for a year, and then headed off travelling with plans to find an accounting job in Sydney.

That plan quickly changed when I got offered a job at a hostel in Byron Bay and, as it turned out, I barely used my accounting qualifications during the 19 months I was away.

Back in Guernsey, I slipped back into accountancy, working for various companies. But deep down, I can’t honestly say I ever really enjoyed any of those jobs. There was always something missing. I’d always been drawn to travel, but once my husband and I bought a house and started a family, financial security became really important, especially while he was building his own business.

The idea of working in travel never quite went away though. I spent most of my spare time researching holidays and eventually decided to train with Travel Counsellors and start my own business. Five months later, Covid hit. I had to return to accountancy while trying to keep the travel business alive at the same time, which at times felt soul destroying.

By the end of 2021, I finally took the leap and became a full-time travel consultant. I work far more hours now than I ever did in finance, and the income isn’t always predictable, but the flexibility and freedom make it worth it. I love being there for my children and building something that’s mine.

My advice? If you’re thinking about a career change, do it sooner rather than later. My only regret is not making the move earlier.”

 

Rebekah Kellow

Rebekah Kellow spent more than thirty years working in education before taking a sabbatical that completely changed the direction of her life. Now based largely in Sri Lanka, she runs businesses including Wanderlust Surf Camp while continuing to call Guernsey home.

Rebekah believes life can change when you’re brave enough to take the first step. 

“When I was fourteen, I knew I wanted to be a teacher. I went on to teach science, biology and psychology in a large comprehensive school in the UK, before later moving into pastoral leadership, which I loved because it felt like such a meaningful way to support young people.

When my son was four, we came to Guernsey on a simple camping holiday with a tiny tent. One day I asked him, ‘Would you like to live here?’ and he immediately said yes. That was enough for me. I set the intention to find a job on the island and the following year we moved to Guernsey, which quickly became home.

I eventually joined The Grammar School and Sixth Form Centre in a newly created SENCO role and stayed there for 22 years. But although I loved teaching and working with students, it was also an incredibly demanding profession. Over time I found myself sitting at my desk after long days, staring out of the window and wondering if this was how the next twenty years would look. 

A volunteering placement in Rwanda reignited something in me. I went on to volunteer in Guyana, Sierra Leone and Tanzania, and those experiences reminded me how much I loved challenge, travel and learning. So I set another intention: to take a sabbatical and do something completely outside my comfort zone.

That eventually led me to Sri Lanka at 54 to train as a surf instructor, despite barely being able to stand on a surfboard when I started. Today, I run businesses there, including Wanderlust Surf Camp in Arugam Bay.

Sometimes in life we reach a moment where we find ourselves thinking, ‘Is this it?’ If that happens, my advice is simple: listen to that voice. You don’t always need to know exactly how things will happen. Sometimes you just need to be brave enough to take the first step.”

 

The Common Thread

Whatever stage of life you are at, there’s no single route to success - and success itself can look very different from one person to the next.

As these women's stories show, careers don't have to follow a perfectly straight line. In fact, it's becoming less common, and sometimes the most rewarding opportunities come from being willing to change direction and staying open to what might come next.