The scariest decision I ever made
Jul 03, 2026
Last month I went back to Milan.
I was there to meet some of my clients. I've been lucky enough to work with some fantastic people based in Milan, including a few who have secured brilliant new roles since we've worked together.
It was such a joy to finally meet in person. We shared coffees, glasses of wine, and celebrated everything they've achieved.
But what made the trip special wasn't just seeing my clients.
It was being back in the city that changed my life.
Milan changed everything
In 2003, when I was 21 years old, I moved to Milan to study at Bocconi University for my final semester abroad.
A semester abroad was something I'd always wanted to do. But when the time came, I was terrified.
I didn't speak Italian. I didn't know anyone. I was on the other side of the world from my family. I was living on a student budget and had absolutely no idea what life in Milan was going to be like.
I have never been so far outside my comfort zone.
Everything about it felt scary.
And yet, it turned out to be one of the best decisions I've ever made.
Growth lives on the other side of fear
Those six months changed me.
I learnt how to be resourceful. How to make close friends from scratch. How to navigate uncertainty. How to build a life in a place where everything felt unfamiliar.
But more importantly, I learnt that I could do hard things.
And once you've done something really hard, everything afterwards feels a little easier.
When I moved to London in 2005, it didn't feel nearly as daunting.
Compared to moving to Milan, London felt easy. English-speaking. Family nearby. Plenty of Kiwis already living there.
Because Milan had stretched me so much, I approached future challenges with a completely different level of confidence.
I knew I'd figure it out.
The lesson most people miss
Most people avoid the things that scare them.
They stay where it's comfortable because they're worried about what might happen if they take the leap.
But the hard things are often the things that create the biggest growth. You don't build confidence before you do the scary thing. You build confidence by doing it.
A full circle moment
As I walked around Milan last month, I couldn't help but smile.
If you'd told my 21-year-old self, sitting in a classroom at Bocconi, that one day she'd be back in Milan meeting clients of her own business, I never would have believed you.
Life has a funny way of rewarding us for the risks we take.
So if there's something you're scared of right now, a move you want to make, an opportunity you're considering, or a challenge you've been avoiding, my advice is simple:
Do the hard thing.
Because you never know where it might lead.
And one day, you might find yourself having your own full circle moment.
If you're facing a big career decision right now - whether that's changing jobs, moving industries, relocating to a new city, or finally going after the role you've been thinking about for years - and would like support navigating this move, the Creative Career Level Up might be the right fit for you.
I help people in the Marketing and Creative and Tech Industries to find their next perfect role.
If you are looking to level-up your career, use the link below to schedule some time to chat about whether the programme might be right for you.