Introduction
What does a genuine midlife career change look like when it comes not from crisis, but from a clear-eyed decision to stop trading time for the wrong outcomes? In this episode of Don’t Let The Old Man In, host Pod O’Sullivan sits down with two executive coaches — Allan Tillack and Andy Sheats — who each walked away from the top of significant corporate careers to design lives built around purpose, adventure, and the kind of leadership that actually lights them up. Their stories speak directly to the men in our audience navigating their own career reinvention at 50, wrestling with questions of identity, executive coaching, and what midlife reinvention really costs — and delivers.
Why this conversation matters
Most conversations about career change focus on people who had no choice. Allan and Andy had every choice. Allan spent over 35 years building a stellar career in multinational pharmaceutical companies, ultimately serving as CEO and General Manager across Australia, New Zealand and beyond. Andy built his career across Silicon Valley and Australia — as a founder, CTO, CEO, and growth leader — before co-founding health.com.au, Australia’s first new health insurer in nearly 40 years.
Both men were high-performing, financially secure, and externally successful. And both of them decided it wasn’t enough. What makes this conversation so valuable for our audience is the honesty about what was actually happening beneath the surface — the quiet burnout, the identity questions, and
What we discuss
- Why high-achieving men leave successful careers — and what’s really going on beneath the surface
- The role of executive coaching in uncovering what you’ve been hiding from yourself
- How to navigate the identity shift when the title disappears and you have to start again
- The “perfect average day” exercise that helped Andy crystallise his next chapter in two minutes
- Why designing a life transition takes years, not months — and why starting now matters
- The surprising parallels between a pharma CEO and a Silicon Valley tech founder reinventing themselves at midlife
- Self-awareness as the starting point for any real leadership or life change
- How relationships — particularly with partners — shape, ground, and sometimes catalyse reinvention
- Why male loneliness after 50 is real, and what both guests are deliberately doing about it
- What the 75-year-old version of you would ask of you today
Why midlife men should listen
If you’re somewhere in your forties or fifties and you’re sitting with the quiet sense that something needs to change — but you’re not sure whether that’s courage talking or just restlessness — this episode is for you. Allan and Andy don’t offer neat answers or tidy formulas. What they offer is something rarer: two honest accounts of what it actually feels like to walk away from the familiar, sit in the discomfort of not knowing who you are without the title, and build something genuinely new.
They’re also both working executive coaches who now help other leaders navigate exactly the transitions they went through themselves. That dual perspective — lived experience plus professional insight — makes for a conversation that’s grounded, practical, and deeply human. Whether you’re thinking about a career change at 50, exploring what executive coaching might do for you, or simply wondering what a well-designed second half of life could look like, you’ll find plenty here to sit with.
Liked what you heard in this episode, but not quite sure what to do with the insights?
We have you covered.
We are releasing a short, 10-minute bonus episode that covers two things:
- What exactly should you do next, and
- Why this is guaranteed to work.
Perfect insights. No excuses.
All you have to do is execute!
Listen or watch on:
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Guest info
Allan Tillack
Allan Tillack is a Sydney-based executive and team coach with more than 35 years of senior leadership experience in the global pharmaceutical industry. After serving as CEO and General Manager of Abbott Nutrition ANZ and Sandoz Australia (a Novartis company) — where he delivered record revenue growth, profit improvement, and multiple industry awards — Allan stepped away from the corporate world in 2018 to complete a Master of Business Coaching at Sydney Business School (Macquarie University). He also holds an MBA from Macquarie Graduate School of Management and has completed senior executive programmes at Kellogg (Northwestern), Tuck (Dartmouth), HKUST, and INSEAD.
Since founding Allan Tillack Consulting, he has coached senior executives across Australia, New Zealand, Asia, Africa, Europe, and the Middle East, helping leaders move beyond intellectual performance into the deeper personal and behavioural shifts that drive lasting change.
Connect with Allan
Andy Sheats
Andy Sheats is a Melbourne-based executive coach specialising in CTOs and CIOs, with a 30-year career spanning founder, CEO, CTO, strategy leader, investor, Non-Executive Director, and Chair. Born in California and raised in Hawaii, Andy began his career in Silicon Valley before relocating to Australia in 2000. His roles include Head of Strategy and M&A at REA Group — where he led global expansion across a dozen countries and saw shareholder value increase tenfold — and Co-Founder and CEO of health.com.au, Australia’s first new health insurer since 1977, which raised $85 million and grew to $120 million revenue within three years.
Andy was named Growth CEO of the Year by AVCAL and is the founding Chair of the Amy Gillett Foundation. He now coaches technology leaders through his practice, CTO Coach, drawing on the Leadership Circle Profile as a “Leadership MRI” to build self-awareness and executive impact.
