Where’s My Money? Season 4, Episode 9
Season Four of Where’s My Money?, now a multi-award-winning podcast, has arrived and we will share all the insights covered across the episodes by host Reagan White and his guests.
enable.me partners with rova to bring this podcast to life and stimulate the conversation about finances with everyday Kiwis. Where’s My Money? follows the story of Reagan – a man chasing the Kiwi Dream but feeling stuck living month-to-month – and his discussions with the experts about what he may be doing wrong and how to fix it.
One man. One million dollars of debt. One podcast to find a way out.
In this Money Month edition of Where’s My Money?, host Reagan White takes three Kiwi women with very different financial styles and puts them through a bold two-week experiment – tracking every dollar they spend.
Meet Grace, Caitlin, and Sam as they rate their existing financial capability:
- Grace rates herself an 7.5-8/10. She’s got a house nearly settled (in December), a savings system she sticks to, and a couple of side hustles.
- Caitlin gives herself 5.5/10. She’s debt-free now, but still building the habits to prepare for future life goals like kids and a bigger family car.
- Sam calls herself a 3/10 but accepts she could be a 4/10. She’s organised on paper but admits discipline isn’t her strong suit – and any money that goes into her “spend in an emergency” savings always ends up getting spent.
With the help of enable.me coaches, the trio’s spending will be tracked over two weeks to reveal hidden habits, red flags, and easy wins that could make a big difference to their financial resilience.
Why tracking matters
Reagan points out that the core of Money Month is building resilience – having the habits, buffers, and structure to handle life’s curveballs. That starts with understanding the basics: money in, money out.
Karen Beckham, a financial coach at enable.me, explains what she looks for when analysing a client’s spending:
- Priorities and values – people’s spending habits reflect what they value most.
- Savings behaviour – whether they save regularly, occasionally, or not at all.
- Debt profile – e.g. short-term debts, buy-now-pay-later services, and liabilities.
- Psychology – the “why” behind spending decisions.
For many people, she says, the biggest problem is simply not looking: “80 per cent of the time – some people have no idea knowing where their money goes.”
Busting common money myths
Karen also challenges some of the small-ticket “sins” we’re told to avoid. Daily coffees and the occasional smashed avocado aren’t what’s stopping most people from getting ahead – unless they’re part of a bigger pattern of unchecked spending.
What worries her more is what’s missing:
No insurance – leaving people financially exposed to accidents, illness, or unexpected events.
No emergency buffer – ideally everyone should have three months’ worth of expenses saved.
No plan – relying on hope instead of strategy to buy a home, pay off debt, or take a holiday.
The starting point
Before the experiment begins, the women share their current situations and concerns:
Grace wants to keep enjoying life after her mortgage starts, so she’s been “practising” her repayments to make sure she can still afford holidays and social events. Her worry? Losing the freedom to do the things she loves.
Caitlin has worked hard to clear her debt and buy into a home, but she knows she still needs to put stronger habits in place. Her biggest challenge? Setting herself up financially before starting a family.
Sam splits her pay into rent, savings, spending, and a “could spend if needed” fund – which always gets spent. She struggles with discipline and admits she’s generous to a fault, often picking up the tab for others. Her stress? Owing money to (or being owed money by) her twin sister after shared outings.
None of the three have more than two months’ worth of expenses set aside – short of the three-month buffer Karen recommends.
The experiment begins
Over the next fortnight, every purchase – from morning coffees to last-minute takeaways – will be tracked via the moneyfit.me Tracker linked to their bank accounts.
Reagan says he hopes the exercise will:
- Reveal blind spots in their spending.
- Show how small changes can free up significant money.
- Model what’s possible in one, five, or ten years with stronger habits.
Karen finishes off the discussion with a practical tip; even small changes in everyday spending can stretch your budget – like choosing takeaway options that last two meals instead of one.
Next time on Where’s My Money?
In the following episode, Reagan and Karen will go through the numbers with Grace, Caitlin, and Sam to see whose habits are better than they thought – and who needs a serious financial tune-up. Listen to the episode below to follow their journey from the start.
Disclaimer: The Where’s My Money? podcast and the information shared by host Reagan White and his guests does not constitute individual financial advice. If you’re interested in receiving financial advice, you can book a consultation with an enable.me coach. Costs apply.
