Today we’re going to have some fun. There’s a trend on TikTok right now called “Coffee with My Younger Self”, where people sit across from an imagined version of their younger self and compare what they thought was important with what actually mattered as they got older. It’s a mix of nostalgia, reflection, and the kind of wisdom that only time can bring. The trend originally started with a poem by Jennae Cecelia, though most people recreating it don’t realise that.
And it got me thinking.

What if we flipped it?
What if instead of meeting our younger selves for coffee, we met our older, retired selves and got advice (and maybe a well-earned kick up the bum)? What if future us sat across the table, stirring their coffee, watching us go through life with all our current assumptions, optimism, and blind spots? Would they be nodding in approval? Raising an eyebrow? Struggling not to choke on their flat white?

Here’s what I imagine future me (or maybe future you) might be thinking. What do you think yours would say? Drop your thoughts in the comments.

1. “You’ve got less time than you think – sort it out now.”
A lot of people in their 50s and 60s assume they’ve got plenty of time to figure things out—retirement planning, super, debt, lifestyle choices. But ask any retiree, and they’ll tell you the years go faster than you expect. Future you would probably say, “Stop waiting. Make some moves now. Get your house in order. Make some plans. Start to dream, save and budget.” Whether that’s finally checking your super balance, working out how much you really need to retire, or deciding what you want this next phase of life to look like—it’s time.

2. “You should have tested retirement before going all in.”
Retirement isn’t a switch you flip—it’s a transition. A lot of people assume they’ll just work full-time one day and be fully retired the next, but that can feel like hitting a brick wall. Future you might suggest a test run—scaling back work, trying a part-time role, or taking a long break or sabbatical to see what retirement actually feels like before making any big decisions. You don’t know what you don’t know, and testing things out could save you from diving into a lifestyle that doesn’t actually suit you.

3. “You worried too much about your money—and not enough about your health.”
Most people in their 50s and 60s stress about whether they have enough money to retire, but future you might say, “Mate, you should have looked after yourself first.” Because what’s the point of having financial security if you’re too unfit, unwell, or exhausted to enjoy it? Investing in your healthspan—staying strong, mobile, and healthy—is just as important as investing in your wealthspan.

4. “You should have spent more on experiences, less on stuff.”
It’s easy to get caught up in buying things—home renovations, new cars, expensive furniture and fancy jeans—but future you might roll their eyes and say, “That new kitchen didn’t change your life, but the trip to Italy did.” Research shows we get more long-term happiness from experiences than from things. So maybe it’s time to rethink what’s actually worth spending on.

5. “You should have spent more on experiences, less on stuff.”
A lot of people picture retirement as either endless leisure or financial doom, but in reality, it’s neither. Future you might say, “Why did you assume you had to follow the old script?” You don’t have to stop working completely at 65 if you don’t want to. You also don’t have to stay in a job you hate just to hit some magic number. More and more people are shaping retirement in their own way—part-time work, passion projects, sabbaticals, reinvention. You get to decide what this phase of life looks like.

So, what would future you say?

Let’s call it “Coffee with my older self” and let’s do it in the comments. But here’s the thing—most of us already know what future us would say. The real question is, what are we going to do about it now?

If future you sat down for coffee with you today, what advice would they give? And are you ready to listen?