The Spending Autopsy: Find the Money Leaks You Can't See

You are a meticulous forensic accountant reviewing my personal spending. I've uploaded [NUMBER] months of my bank and credit card statements.

Your job: categorise every transaction and give me an honest picture of where my money actually goes.

Steps:
1. Read every transaction across all files. If any are ambiguous (unclear merchant names, transfers between my own accounts, etc.), list them separately as "Needs my input" rather than guessing.
2. Sort all spending into clear categories: Housing, Groceries, Eating out & delivery, Transport, Subscriptions, Shopping, Health, Entertainment, Fees & interest, and anything else you find. Create sensible sub-categories where it helps.
3. Produce a summary table showing, per category: total spent, monthly average, and % of total spending.
4. Tell me my total spend, my average monthly spend, and (if income is visible) my average monthly surplus or shortfall.
5. Call out the 5 biggest single categories and the 5 biggest individual merchants by total dollars.

Rules: Use Australian dollars. Be precise with numbers — show your working if a figure looks surprising. Do not flatter me or soften anything; I want the real picture. Flag anything you're genuinely unsure about rather than inventing a number.

Start by telling me how many transactions you found and the total across all files, then give me the full breakdown.

Now switch roles: you're a sharp, money-savvy friend who's brilliant at spotting waste — the kind who looks at a statement and goes "wait, why are you paying for THAT?"

Using the same statements, find my money leaks. A leak = spending that's recurring, forgettable, easily reduced, or delivering little value for the dollars. Specifically hunt for:

1. Subscriptions and recurring charges — list every one you can find, the amount, the frequency, and the annual cost. Flag any that look duplicated, forgotten, or rarely used.
2. "Death by a thousand cuts" spending — small, frequent purchases (coffees, delivery fees, convenience-store top-ups, in-app charges) that add up to a large annual total. Show me the annual total for each pattern.
3. Fees, interest, and avoidable charges — account fees, late fees, ATM fees, foreign transaction fees, overdraft interest.
4. Lifestyle creep — anything where spending has clearly climbed over the months.

For each leak, give me: what it is, the monthly cost, the ANNUAL cost, and a one-line note on how hard it'd be to cut. Rank them by annual dollar impact, biggest first.

Be brutally honest but never preachy — I want to feel informed, not lectured.

Based on everything you've found, give me my Top 3 Fixes — the three changes that would save me the most money for the least pain.

For each fix, give me:
- The change, in one plain sentence
- What it saves me per month and per year (real numbers from my data)
- A "pain level" of Easy / Medium / Hard, and why
- The exact first step I'd take this week to do it

Then add up the three annual savings and tell me the total — and reframe that total as something tangible (e.g. "that's X" — a trip, a debt cleared, a savings buffer).

Rules: Prioritise realistic, sustainable changes over extreme ones — I want fixes I'll actually stick to, not a crash diet. Don't suggest I cut things that clearly bring me joy or value; target genuine waste. If you need to ask me up to 3 questions to make the recommendations sharper (e.g. whether I still use something), ask them first.

I set the priorities here — you're just showing me where the easy wins are.

Help me turn this into a monthly money check-in I can repeat.

Write me a short, reusable prompt I can save and paste into a Claude Project each month, along with my latest statement. It should: categorise the new month, compare it against the averages you calculated today, flag any leak that's crept back in or any new recurring charge, and give me one thing to watch next month.

Keep the saved prompt tight and copy-paste ready.

I want to interrogate my [CATEGORY, e.g. food delivery / rideshare / online shopping] spending specifically.

Using my statements, show me: the total over the period, the monthly trend, my most frequent merchants, and the single most expensive month. Then ask me 2–3 sharp questions to help me decide what this spending is really buying me — convenience, time, comfort, avoidance — so I can judge whether it's worth it. Don't tell me the answer; help me think it through.