When I got deeper into building my SaaS app, I upgraded from Claude Pro to Max - a jump of $17/mo to $100/mo. Steep, I know. But at the time I was in 4-hour sprints squashing bugs and feverishly adding features and polishing up the UI.

I kept hitting rate limits and decided I was losing value by waiting for my tokens to reset. Felt totally worth it for that period.

But then that period passed…

…And I totally forgot I made that pricey upgrade.

I also previously set up a Squarespace that was live but largely unused for about 9 months. A little over $300 in waste. It hurts to type that.

THE FRICTION

I depended on memory and discipline to:

And so you just might understand why this $400 slipped away so easily.

This is what I think of as the Subscription Tax - the cost of subscriptions continuing by default unless you actively intervene.

It’s not always a big, dramatic expense. It’s usually quiet leakage. A few dollars here, a few dollars there - money leaving your account without a deliberate yes. And it adds up.

In fact, did you know most of us waste between $200 and $600 a year on "vampire" renewals and forgotten free trials?1

Not to mention the tech stack for business owners. One entrepreneur I talked to has over 23 tools in his stack. Many of them he thought were poor quality but paid anyway because he forgot.

And yet the real cost isn’t just financial.

There’s also the background mental load of maintaining things you’re no longer using. The friction of knowing you should clean it up, but not having a clear trigger or owner to do so.

Subscriptions are just one place we pay what I think of as a Maintenance Tax - the ongoing cost of keeping too many small systems alive without a clear owner, reminder, or boundary. Tools, tasks, inboxes, ideas, half-built systems.

The solution isn’t to be more disciplined or remember better.
It’s to stop relying on memory at all. Here are two simple systems that make subscription decisions explicit instead of passive.

1) Set up a regular check-in with yourself / partner / roommate / interested parties at a cadence that feels doable. Quarterly is probably sufficient, monthly if you’re watching your spend a bit more closely due to personal budget or business performance fluctuation.

Look through emails or credit card statements:

Does it feel justified? This could be measured by utility (e.g. Stripe needed for business payments) or simply, joy!

My husband and I try to maintain only 1 streaming service at a time. And when there is a new season of Slow Horses, it’s an absolute must that we have Apple TV that month. If you’ve watched the show you know that Jackson Lamb’s retorts are worth it.

2) Set up a flow that automatically creates renewal reminders ahead of when subscription charges will hit so you won’t be caught off guard.

Set it and forget it!

Which leads us to…

WHAT I BUILT
A Zap that monitors my Gmail for subscription receipts, extracts the renewal date and price using AI, and drops a bright red "CANCEL" reminder on my Google Calendar three days before I get charged. I gave it examples (Google Play, Apple, Disney+, New York magazine) so it could handle variations.

No spreadsheet to maintain. No mental overhead. Just a calendar event on January 12 that’s titled: "CANCEL SQUARESPACE $36 1/15"

Then I can decide if I still need it - with time to actually cancel before the charge hits.

📋 Recipe:
Free Zapier template

⚙️ Ingredients:
Zapier + Gmail + Google Calendar

👩🏻‍🍳 Cook time:
If you already have a Zapier account —> 5 minutes to connect the Google integrations

👷🏻‍♀️ DIY version:
If you want to build this yourself, I’d recommend using Zapier’s Copilot feature and the following prompt as your starting point.

Feel free to customize to your liking (different email provider, earlier reminder window, title formatting, etc.)

Build me a Zap that creates Google Calendar renewal reminders for subscription receipts.

Trigger: Gmail - New Email in INBOX

Step 2 - Filter: Only continue if email subject OR body contains: "receipt", "subscription", "renewal", "invoice", or "billing"

Step 3 - AI by Zapier (OpenAI GPT-4o-mini): Extract from the email body:

Output JSON: { "calendar_title": "CANCEL [PRODUCT NAME ALL CAPS] $[ROUNDED PRICE] [RENEWAL DATE]", "reminder_date": "YYYY-MM-DD" }

Date format in title: M/D if same year as event, M/D/YY if different year.

Step 4 - Google Calendar: Create all-day event

Filter keywords: receipt, subscription, renewal, invoice, billing

Systems » willpower

Will this work every single time? Maybe not. Some companies don't include renewal dates in their emails. But this flow should catch most of them - and that's a vast improvement over "hope I remember" for all your subscriptions across streaming, music, and business tech stack.

If nothing else, the check-ins will introduce a habit of being more aware of these expenses and forcing you to reckon with what’s really driving value - or joy - and whether that’s worth the cost.

If you try the Zap, hit reply and let me know if it helped you avoid my $400 mistake 😉