Day 3: The Art of Planning (sort of)...

3/365

Why is coming up with a plan so tricky at times? It’s so easy to picture your dream life — the 5, 10, 15-year “future me is thriving” montage. But the second someone says, “Okay… but how are you getting there?” the brain just flatlines.

So, how do we combat this?

Firstly, if this is something you struggle with, having some context around planning as a skill might help you feel better about it. Planning is a core executive function (which sounds very serious and adult, but basically means you need it to function as a human).

When you’re an infant, the extent of your planning might look something like this: you see a toy car across the room, you want the toy car, you start crawling toward said car, pick it up with one hand, and straight into your mouth it goes. As you grow, the complexity of planning increases to match your pursuits.

But what happens when you reach an age where there’s no longer a clear blueprint to follow? No curriculum telling you what to learn, no coach yelling from the side lines to pass the ball, and no parents in your ear about studying after school. One day, the training wheels are just gone — and suddenly you’re left to navigate the traffic on your own.

So, here’s what you can do:

1. Write out what the end goal is — but make it SMART.

For example: I want to save $30,000 in the next 15 months to put toward a house deposit.

2. Break the goal down even further (before it breaks you).

Saving $30,000 in 15 months means $2,000 every month or $500 every week.

3. Identify what actions you need to repeat or automate. Set up an automatic transfer each week, fortnight, or month (depending on your pay cycle) into your savings account.

4. Identify any potential barriers or hindrances — and how you can avoid them.

If your partner’s birthday is coming up in two months and you’ll need to buy a present and plan a dinner, you could reduce your usual spending on leisure and outings in the lead-up to avoid disrupting your savings transfers.

5. Set reminders to monitor your progress.

At the end of each month, review whether you’ve hit your savings target.

6. Identify what’s working well and what isn’t — then adjust accordingly.

If you’re constantly tempted by food delivery apps, unlink your debit card to prevent impulse spending.

7. Keep going and repeat steps 3–6 for as long as the goal is relevant.

I know setting financial goals might seem relatively straightforward (for some people), but there are other situations where planning feels much more gruelling — and anxiety-inducing. So, here’s a personal example that might feel more relatable. (Disclaimer: there’s still a money theme ahead.)

Recently, I was trying to decide whether to invest in property. It sounds like a no-brainer if you have the money. Everyone says it’s better to have your money working for you than just sitting in a basic 3% interest savings account.

But here’s what changes things: I’m a woman in my 30s, single (with no promising dating prospects in sight), and the biological clock isn’t exactly whispering. So, the other option I’ve been considering is whether I should freeze my eggs. Having a family has always been one of my biggest goals. So where do I invest my money?

After going back and forth for quite some time, here’s the plan I came up with:

1. Set aside money for a comprehensive health check-up, including an AMH test, to identify any underlying fertility concerns.

2. Based on the results, decide whether egg freezing is necessary within the next two years.

3. Continue meeting new people — through dating apps and new experiences — to stay open to possibilities.

4. Stick to the financial plan I already have in place and review my situation in 12 months.

   
   

I know this plan isn't as specific at the seven-step plan I have above about saving money— but that’s the nature of some situations. You can plan up to a certain point, and then you need to reassess.

Keeping that in mind can help ease some of the nervousness and confusion that comes with planning. Accept that it’s a skill that requires upkeep — and that things will inevitably change. That’s not to say planning is pointless.

Think of a plan like a tree: the trunk is your main goal, while the branches represent your sub-plans, detours, and course corrections. You might sway, bend, or even grow in unexpected directions, but ultimately, you’ll still get where you want to go.

So, keep your goals in sight, break them down, identify your actions and barriers, review your progress, and keep going.