Rory D’Agostino, a Senior Financial Adviser at Navigate Advisory, is someone who truly walks the talk when it comes to living a great life.
What does it mean to you to live a great life? How do you live a great life?
“For me, a great life is all about balance. Finding the balance between spending time with family, friends, new adventures and experiences, and doing all the stuff that really puts a smile on your face. As a new dad, the balance is a bit out of whack at the moment as I just want to spend time with my son and watch him grow and learn new skills.”
That balance, for Rory, comes with a healthy dose of adrenaline. His eyes light up as he describes spending time outdoors, “whether that’s ocean swims, surfing at least a couple of times a week, or snowboarding overseas.”
Recently, he challenged himself to complete an 82 km bike ride for charity – a challenge that pushed him well outside his comfort zone being twice as far as previously ridden. “The ride was about putting your mind to something and actually working towards an end goal,” he reflects. “Being able to raise over $40,000 for MS, which is the most common neurological disease in young adults, was incredible.”
Between adventures, Rory is adamant about always having something to look forward to. “There’s no week that goes by where I don’t have something planned,” he shares. “whether it’s a weekend down the Coast, up the Coast, or planning the next overseas adventure there’s always something in the diary and plans bubbling away.”

You mention that one of the best parts of your job is “opening clients’ eyes to possibilities they’d never considered.” Can you share a memorable story where you helped transform a client’s relationship with both their money and their life goals?
“One particular one that comes to mind is a young family who was really concerned about taking that next step in the property ladder, moving from their second home to their forever home.”
He explains how this transition represents more than just a property purchase. “That’s quite a big jump, both in terms of how much you have to take out in terms of debt, the cash flow, the risk, the job, the career, all that stuff.” His role was to help them see beyond the numbers to the possibility of their dream becoming reality.
“Recently, after a 6 month process, this dream has become reality” he says proudly. “They’ve bought that place close to the water, close to their kids’ school, a place that suits their lifestyle. They’ve said to me that’s where they’re going to live for the next 30 years. For me, that’s probably the most rewarding part of what I do – helping couples and families make these life milestones happen.”
Over your decade in financial services, how has your understanding of what makes a “great life” evolved?
When I first joined this industry just over 10 years ago, I honestly thought it was all about the numbers. But in reality, it’s rarely about the numbers.”
“It’s all about people wanting to spend time with their family, making sure that they’re healthy, making sure that everyone’s looked after. And if you can show clients that money is just an enabler to get to that point, then I think that will generally make a great life for everyone.”
“As a new dad, this feels more real to me than ever.”
This evolution in thinking has shaped his approach to client conversations. “We go through a defined process to really understand what makes a great life for people” he explains. “A lot of couples that I deal with have never really had these conversations together and so it is rewarding being a part of that.”
He sees his role as more than just a financial adviser. “For me, it’s all about working through trade-offs because for every decision that you make, there’s always going to be a trade-off as part of that. It’s really about what’s the most important thing to you, what’s going to add the most value to your life. That value is never about the dollars. It is so much more than that.”
When working with high-achieving professionals, what’s often the biggest mental shift they need to make to move from just accumulating wealth to creating their version of a great life?
“I find when couples first come into our office, they’re often not on the same page about money. They haven’t really had the chance to talk about their goals because they’re so busy dealing with everyday life. Usually, they have different ideas about what a great life looks like and what money means to them – often because of their different upbringings and experiences with money.
He sees his role as a bridge between these perspectives. “A big part of my job is to actually bring that together and then work with them and go, ‘What’s important for both of you and what is the best way to get there?’ Rather than just trying to scrimp and save, it’s about using what you’ve already built and using that to build a great life.”

Rory D’Agostino is a Senior Financial Adviser at Navigate Advisory, specialising in helping aspirational families grow and protect their wealth.