Bills, Renewals & Subscriptions

What's coming, and what's about to renew.

The monthly scan tells you what hit last month. This lesson is about what's coming. Bills due in the next month, subscriptions about to auto-renew, contracts that quietly renew if you don't say something, annual things you forgot are annual. Cowork pulls the list from your Money Reference and the most recent scan, sorts by date, and tells you which ones need a decision before they fire.

One way to ask:

Sample — what's coming up

Pull together everything coming due in the next 30 days — bills, subscriptions, auto-renewals, annual charges. Use my Money Reference and the most recent monthly scan. List in date order with: what it is, rough amount, whether it's auto-pay or needs me to do something, and whether it's a "renews automatically unless I cancel" type that I should think about before the date.

Cowork returns the list. Anything you didn't realize was renewing — that's where the next screen comes in.

Keep, cancel, or negotiate — the four questions.

When something's about to renew (or showed up on the monthly scan as "still paying for this?"), four questions usually get you to a clean decision. You can think them through yourself, or hand them to Cowork.

The four questions

Have I actively used this in the last 30 days? If no, that's data.
Does it earn what I'm paying for it monthly or annually? Compared to the value, not just the dollar amount.
If I canceled tomorrow, would I miss it in a week? The honest version of "do I want to keep this."
Is there a free or cheaper option I'd actually switch to? Sometimes there is and you've just never moved.

One way to have Cowork walk you through:

Sample — think it through with Cowork

Help me think through whether to keep [subscription name]. Ask me the four questions one at a time — usage in the past month, value relative to cost, whether I'd miss it, and alternatives. Then summarize where my answers land and recommend keep / cancel / look for cheaper, with a one-sentence reason.

This is one of those moments where you might want Cowork to push back if you're rationalizing. The push-back habit from earlier in the course applies here too — "don't just agree with what I said, tell me if my answers actually justify keeping it." Cowork will be honest if you ask it to be.

Drafting the actually-hard ones.

Most cancellations are two clicks online. The cases that need help are the ones designed to make leaving painful, and the cases where you're disputing a charge that shouldn't have happened.

When the service makes cancellation hard.

Gym memberships, some insurance products, "call to cancel" services. Cowork drafts the email or letter that gets it done.

Sample — cancellation request

Draft a cancellation request to [service]. I want my account closed and any auto-renewal stopped, effective [date]. Include my account identifier (use the last 4 digits of my card from Money Reference, account holder name, and signup email). Specify that I want written confirmation of the cancellation. Tone: polite but firm — don't apologize, don't open the door to retention offers. Save the draft in this Project's folder, and if email works for this service, save it as a Gmail draft I can review and send.

When a charge is wrong — the dispute letter.

Different from cancellation. The dispute is to your bank or card issuer, asking them to reverse or investigate a charge.

Sample — dispute letter

Draft a dispute letter to [bank or card issuer] for a charge from [merchant] on [date] for [amount]. The dispute reason is [unauthorized / wrong amount / service not received / duplicate charge / etc.]. Include any relevant detail about what happened, but don't speculate or add anything I haven't told you. Match the formal tone banks expect for disputes — calm, factual, no emotion. Save it as a Word doc I can send (or as a Gmail draft if my card issuer accepts disputes via email).

One thing to know about disputes.

Card issuers have specific time windows for disputes — typically 60 days from the statement date for credit cards, less for debit. If a dispute is months old, Cowork should flag that in the draft. Don't delay — once it's flagged on the monthly scan, handle it that week.

A few patterns worth using.

The "renews on a specific date" reminder.

Some subscriptions you do want to keep, but only if you remember to look at them before they auto-renew. Tell Cowork:

Set up renewal reminders

Look at my Money Reference. For any subscription that auto-renews annually, set up a scheduled task that reminds me 10 days before the renewal date. The reminder should tell me what's renewing, the cost, and ask whether to keep it. That gives me time to cancel if I want to without scrambling.

The annual "what am I paying for this year" summary.

Once a year (typically when doing taxes or year-end planning), ask Cowork to produce a full subscription and recurring-cost summary:

Annual recurring-cost summary

Walk through every subscription, recurring bill, and annual charge from my Money Reference and the past year of monthly scans. Show me what each one cost me in total over the year. Sort by annual cost, biggest first. Flag anything where the annual cost surprised me (because monthly looked small but adds up).

Next: Sunday Money Reset.

Last lesson of the module. Same pattern as the Sunday Household Reset, applied to money — a short weekly look at where things stand. Money modules are about staying ahead; this is the lightweight weekly habit that keeps you there.

Continue to Sunday Money Reset →