Introduction
Mindset can make or break your success in property development. In this episode, we’re diving into what it really takes to stay grounded, focused, and solution-oriented when the pressure hits.
From Bob’s $1 million court battle to student stories of procrastination and analysis paralysis, we talk openly about what can derail your journey—and how to stay mentally strong through the ups and downs. We also share practical tools to build resilience and confidence, so you can keep momentum when things don’t go to plan.
Episode Highlights
[00:39] Bob’s $300 fishing fail and why maintenance matters
[03:45] Why development is like a highway—fast stretches and speed bumps
[06:30] Bob’s early days in corporate and managing imposter feelings
[08:15] Taking on a 67-storey project with no prior corporate experience
[10:20] Mentorship and mindset shifts that kept Bob on track
[14:20] Stick to the plan, but allow for smart flexibility
[17:45] A costly retirement village appeal and how Bob kept going
[21:30] Five years of inaction can cost millions—why regret is a poor plan
[24:30] Overcoming paralysis by analysis and micro-managing tendencies
[27:40] Managing fear by breaking tasks into wins
[30:00] Where confidence comes from—and why trial-and-error won’t cut it
[32:50] Hilary’s practical tools to build a resilient mindset
[38:20] Traits of successful developers: positivity, discipline, self-investment
[39:59] The power of starting, even when things aren’t perfectly lined up
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The Episode In Brief
Episode 211 dives into the mindset needed to navigate the highs and lows of property development—how to stay focused, adapt when plans go off track, and build resilience that carries you through.
Hilary: “We all hit detours and delays. It’s how you think through them that makes the difference.”
Bob: “Without the right mindset, you won’t make it through your first serious challenge.”
Taking On More Than You Think You Can
Bob: “I wanted to get experience in a big development company doing big projects.”
Bob shares how, at just 30 years old, he stepped into a senior corporate role—overseeing a 67-storey CBD tower—well ahead of his peers.
“It was after I got the role that I started to think, my God, am I up to this?”
Even with decades of development experience behind him now, this moment tested his belief in himself. Fortunately, he had a mentor who guided him and recognised his entrepreneurial instincts.
Projects That Test Your Grit
Bob: “A million dollars later, it still hadn’t been approved, but it was close.”
This court appeal over a retirement village approval dragged on for more than a year, pushing Bob mentally and financially.
“That took over a year. That really tests you mentally… writing out a check for $25,000 every Friday afternoon.”
His ability to manage stress came down to focusing on small steps.
“Just try and get little wins along the way rather than just concentrate on the big win or the big loss.”
Stuck in Planning? Start Anyway
Bob: “Five years on, still in a job they don’t like, still haven’t taken that step.”
Many aspiring developers delay for years. They wait for the “right” time—but often miss years of opportunity.
Hilary: “Don’t wait for all the little ducks to line up in a nice straight line.”
Her message is clear: clarity comes after action, not before.
Building Confidence (and Why You Can’t Fake It)
Bob: “Confidence comes from learning and understanding what it is you have to do.”
It’s not about fake positivity or trial-and-error.
Hilary: “If you don’t have the knowledge, you can’t solve the issue—or see it coming.”
Education, support, and process build the foundation that confidence grows from.
Resilience Is Built, Not Born
Hilary: “They have an expectation that they will do well and they’re prepared to invest in themselves.”
Successful developers carry a mindset that’s optimistic, but not naive.
Bob: “Development’s like a highway—you’ve got speed bumps and detours.”
Those who succeed expect challenges—but they keep driving anyway.
Real-World Lessons from Bob & Hilary
“Stick to your plan. You have to be a little bit flexible with property development as well.” – Bob
“Paralysis by analysis… we see all of those things from time to time.” – Bob
“Know why you want to do it. Don’t procrastinate.” – Hilary
“Clarity follows action.” – Hilary
Final Thoughts
Mindset underpins everything in property development. Whether it’s managing risk, handling setbacks, or facing big opportunities, how you think will shape what you achieve. Start with learning, get the right support, and trust the process—because as Bob puts it, “Confidence comes from competence.”