You raised your kids. They’ve finished school, maybe even uni. They’re ambitious twenty-somethings. Some of your music tastes have rubbed off on them, and yes, that does make you feel a little smug. They’re working hard, chipping away at student debt, and trying to break into a housing market that makes *The Hunger Games* look like a stroll in the park. Oh! and they’re still occupying a bedroom in the family home. Not just for the Wi-Fi.

Meanwhile, your parents are entering their final chapters with increasing needs. Mobility issues, medical appointments, loneliness, or dwindling savings as the cost of living outpaces their retirement plans. And you? You’re right in the middle of it all.

Welcome to the Sandwich Generation 2.0.

This Isn’t the Life We Planned (But It’s the One We’ve Got)

Coined in the 1980s to describe women juggling kids and ageing parents, the “sandwich generation” label now belongs to many of us (men, women, couples) doing our best to care for both ends of the generational stick while trying to avoid snapping in half ourselves.

But here’s the good news: midlife doesn’t have to be a purely logistical mess of calendars, meal prep, and late-night pharmacy runs. With the right mindset, it can be a stage of meaning, growth, and intentional redesign.

Helping Your Kids Without Hurting Your Future

First, let’s dispense with the guilt. It’s OK to help your adult children. They’re facing headwinds we never knew. The average Sydney house price in 2000 was around \$233,000; now it’s nudging $1.4 million. According to Australian Property Update, today’s 25-year-olds need 14 years to save a deposit. When we were 25? Just six years. And interest rates? Try 18% in 1990, yes sure, but on a house worth less than your car is today. It’s not the same race.

A 2025 Forbes report found nearly 60% of parents with adult children provide ongoing financial support. So, you’re not alone. But support doesn’t mean sacrifice. Maybe, instead let’s start with this question: “What can I afford to give without compromising my own financial security?” If you drain your super now, who’ll be bailing out whom in 20 years?

From that foundation, we might then ask: “How do I help them build independence?” Open financial conversations are key. Share your own money mistakes. Talk about budgets. Even if you’re still paying their phone bill, encourage them to co-pay on rent or utilities. Teach them to plan.

If you need a primer, revisit this article (insert link here) on financial literacy, it covers practical steps like helping your kids set savings goals, invest early, and avoid Instagram-fuelled spending habits.

Your Parents Are Teaching You (Whether You Notice or Not)

At the other end, your parents are slowing down. You may be managing medications, transportation, downsizing, even navigating in-home care. Pay attention. Their experience is your future in preview.

• Have they run out of money?
• Are they isolated or engaged?
• Are you having conversations they avoided?

Let their journey inform yours. Make your will. Organise enduring power of attorney. Write down your healthcare wishes. Talk to your family. It’s not morbid, it’s a gift. According to the AIHW, almost one in five older Australians now live alone, often due to poor planning or fractured relationships. Don’t let that be your story.

Breaking the Cycle

So how do we care for others *and* protect our own future? Start here:

1. Secure your own oxygen mask first: Protect your retirement. You’re not selfish. You’re ensuring your kids won’t be paying your rent in 2045.

2. Raise financially literate adults: Set expectations. Tie support to behaviour. Teach them the value of compounding interest and cooking their own meals.

3. Invest in health and connection Physical health, mental agility, and friendships all buffer against the slow fade. Book the check-up. Take the walk. Say yes to the book club. Even the one with wine.

Designing the Life You Want (Before Someone Else Does It For You)

Agency is a fancy word that sounds like something out of a social sciences textbook, but it really means making choices now, and that starts by asking a simple question: Who’s writing your story?

We grew up believing in work, duty, sacrifice. But what if the point of midlife wasn’t just more of the same? A recent Straits Times article put it beautifully: “It’s not just about living longer. It’s about having a say in how we live later. And that begins in our 50s, not in our 80s.”

That’s the takeaway. Don’t wait for retirement to start planning your life. Do it now, while you still know where your glasses are.

A Final Word of Encouragement

Feeling stretched thin? That doesn’t mean you’re failing. This is a hard season. But it’s not a dead end. You can care without collapse. Support without surrender. And shape a future where your kids aren’t trapped in the same cycle. This is what real agency looks like: not control, but “authorship”, of our own story, and of theirs.

Turns out paying it forward might be the smartest retirement plan of all.

There’s a reason the podcast Don’t Let the Old Man In resonates with thousands of men in their 50s. It speaks to the quiet war many fight against obsolescence, irrelevance, and a determination to navigate life’s crossroads with clarity and confidence. And likewise, if you’re reading this, you haven’t given up. You’re still curious. Maya Angelou once said, “If you’re always trying to be normal, you will never know how amazing you can be.” Midlife career change isn’t about being extraordinary. It’s about being aligned—with yourself.

Stephen Keys is the Producer of the Don’t Let the Old Man In podcast. Listen on YouTube, Apple, Spotify or wherever you tune in. Find more thoughts on living gracefully (and disgracefully) in the second half of life at The Wisdom Vault, on LinkedIn, Substack and even (!) Instagram.