There’s a particular kind of stress that lives in the background of modern life. It’s not the dramatic, headline-grabbing sort. It’s the quiet hum of unfinished business: the passwords you never wrote down, the documents you can’t quite find, the family conversations you keep meaning to have “one day.”
Most of us know we should do some future planning. We’ve read the articles, ‘admin nights’ are becoming a trend currently! We’ve seen friends scramble when something changes unexpectedly. We’ve told ourselves we’ll get around to it after the next busy week.
And yet we don’t. Not because we’re careless. Not because we’re in denial. We don’t do it because the practical side is rarely the real barrier. The real barrier is emotional.
When people say, “I just can’t deal with that right now,” what they often mean is, “I don’t know how to talk about this without upsetting someone … or being upset myself.”
Why we avoid these conversations (and why that makes sense)
If you’ve ever tried to raise a topic like “Who would you call first if something happened?” or “Have you thought about what you’d want if you were unwell for a while?” you’ll know the emotional undertow it can create.
We worry about being seen as morbid. We worry we’ll jinx something by naming it. We worry the conversation will explode into conflict, especially if siblings have different views, or if family history is complicated. Sometimes we worry the other person will interpret planning as control: “Are you trying to make decisions for me?” And often, we fear the awkwardness itself, how it will feel to sit there in the silence after you say the thing you’ve been avoiding.
Underneath it all is a very human instinct: to protect the relationship. Our brains are wired to avoid friction and preserve connection. So we postpone. We soften. We change the subject. We convince ourselves it can wait.
The trouble is, postponing doesn’t remove the emotional weight, it just spreads it out over time. What would have been a short, thoughtful conversation becomes months or years of low-grade stress, and then, too often, a rushed conversation under pressure.
If you want a more honest definition of planning, it might be this: planning is a way of caring for your people before they have to carry your admin. And that’s not morbid. That’s generous.
The trick is not to make it “The Big Talk”
Most people approach these topics as if they require a single, monumental conversation where everything is decided and everyone feels calm and mature and grateful. That expectation alone is enough to stop anyone from starting.
A better approach is to treat it like any other caring conversation in a family: you start small, you ask permission, you focus on one thing, and you leave with one next step.
When you lower the stakes, you lower the resistance. It becomes less like “We need to talk about the end of life” and more like “Let’s make life a little easier for each other.”
A simple way to start gently
One of the most effective moves is also the simplest: begin by asking permission rather than making an announcement.
Try something like, “Can I run something past you?” or “Is now a good time for a quick chat, ten minutes?” The permission step matters because it gives the other person control. It signals that you’re not about to corner them with a heavy topic, and you’re not demanding a full emotional performance.
Once you have a yes (or even a “not right now”), you can name your purpose in a warm, human way. This is where many people go wrong. They lead with paperwork. They talk about forms. They reach for logic, hoping it will make the feelings disappear.
Instead, lead with care: “I’m not trying to be heavy. I just want us to feel more organised,” or “I’ve seen families get stuck in confusion because no one knew what someone wanted. I’d love us to make it a bit easier.”
Purpose softens the conversation. It turns it from a threat into a gift.
Then comes the most important piece: choose one topic only. Not everything. Not a full plan. One decision or one piece of information. You might choose who to contact first in an emergency, where key documents are kept, who should speak on someone’s behalf if they couldn’t, or what matters most if someone needed extra support for a while.
When you choose one topic, you make the conversation achievable. You also make it safer. People can handle ten minutes. They struggle with the feeling that they’re being asked to rewrite their entire life on the spot.
Finally, you end with one next step. This is how you prevent the conversation from becoming yet another “We should do this sometime” moment. Your next step might be, “Could we write down the three things you’d want us to know?” or “Can we put your insurer contact and policy number in one place?” or “Let’s set a reminder to revisit this in a month.”
That’s the framework: permission, purpose, one topic, one next step. It’s gentle. It’s human. And it works.
What to say (without sounding dramatic)
If you’re talking with your partner, you can keep it light and practical: “Can we do a ten-minute life admin check-in this week? Nothing intense, just enough so we know where the important stuff is and who we’d call first if something unexpected happened.”
With a parent, it can help to frame it as “help me help you.” Parents often resist planning conversations because they fear losing independence. But many will respond to the idea of removing guesswork for the people they love: “I realised that if anything changed quickly, I wouldn’t know where to start. Would you be open to telling me where the key documents are and who you’d want contacted first? We can keep it simple.”
With an adult child, the tone can be reassuring: “I don’t want you to ever have to scramble for information if I’m unavailable. Can I show you where the essentials are kept? This is about making life easier, not worrying.”
With a sibling, you can name the reality without making it accusatory: “If we ever had to make decisions quickly, I’d rather we weren’t trying to work it out in the moment. Can we agree on a few basics now so it’s calmer later?”
And sometimes, the right script is the one that protects the relationship when the other person isn’t ready. If you meet resistance, your job is not to win. Your job is to keep the door open: “That’s okay, I don’t want to push you. I’m going to start with my own plan so it’s easier for everyone if I’m ever unavailable. If you ever feel ready, we can revisit it later.”
That sentence does something powerful. It honours their boundaries while still protecting your future.
The two kinds of readiness most families need
In practice, families usually need two things: emotional readiness and practical readiness.
Emotional readiness is the ability to have the conversation without turning it into a battleground. It’s choosing a calm time. It’s being willing to hear “not yet.” It’s keeping it to one topic. It’s prioritising connection over being “right.”
Practical readiness is having a simple system so information is findable and shareable. It’s knowing the top essentials, having them in one place, and making sure the right person can access the right information when needed, without oversharing everything.
When one of these is missing, planning stalls. If you have the documents but no conversations, family members still end up guessing. If you have the conversations but no system, you still end up searching.
You need both. Not all at once. Just over time.
The small action that makes everything feel easier
If you want to feel a measurable sense of relief today, do one small thing: choose one “high-impact” item and put it somewhere safe and findable.
That might be your insurance policy number and insurer contact. It might be a current medication list and your pharmacy contact. It might be a photo of your Medicare card and emergency contacts. It might be the name of your chosen decision-maker and how to reach them. It might be your primary email and a secure plan for device access.
Then add one sentence of context: “If something happened, the person who would need this is ___.”
That’s it.
It’s not a full plan. It’s not a dramatic statement about the future. It’s a simple act of care that reduces mental clutter immediately. It turns planning from an abstract, emotional mountain into a concrete, manageable step.
And once you’ve done one step, you’ve done the most important thing of all: you’ve started.
Planning is a love language
At its core, planning is not about being grim or overly organised. It’s about giving your people the ability to focus on what matters—each other—rather than paperwork and guesswork.
It’s also a way of caring for yourself. There’s a particular peace that comes from knowing you’ve captured what matters, that your preferences are clear, and that your family won’t be left trying to interpret your life in the middle of an emotionally difficult moment.
So if you’ve been putting it off, take the pressure off. Don’t aim for a perfect conversation. Aim for a gentle one. Ask permission. Share the purpose. Choose one topic. Take one next step.
You don’t need to make it weird.
You just need to make it kind.
Rechelle Leahy is a UN delegate and founder of iDecide, she uses lived experience to drive impact. Her leadership has earned national recognition, including being named one of the AFR’s 100 Women of Influence.