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I'm the type of person who takes advantage of free trials and then forgets to cancel them. Then, with every new charge, I try to figure out how to cancel them and then wonder if I should keep them. It's a vicious cycle that I'm not proud of — most of all, it's a waste of money.If you're like me, you know that between streaming services, cloud storage plans, AI subscriptions, fitness apps and a slew of digital memberships, it's surprisingly easy to lose track of what you're paying for each month.I recently decided to audit my own subscriptions and instead of manually sorting through everything, I used ChatGPT as a personal financial assistant. It was much faster than I anticipated and I finally got a better picture of every subscription. When I added everything together, I discovered I was spending nearly $166 per month on subscriptions, or almost $2,000 per year.Here's exactly how I used ChatGPT to do it.Step 1: Gather all of your subscriptionsIf you're like me, you have subscriptions connected to Amazon such as Amazon Music and Audible, as well as Amazon subscriptions like automatic reorder. At the same time, I also have subscriptions tied to Apple such as LinkedIn, Apple+, other streaming services and app subscriptions. Plus, we can't forget about other memberships and subscriptions through Google or that are completely seperate. Pulling together all your subscriptions from multiple places is a challenge in itself. I have an iPhone so I started by going to: iPhone: Settings > Apple ID > Subscriptions. From there I checked Google Play subscriptions, Amazon memberships and digital services, credit card statements, PayPal recurring payments and even bank statements.I had almost no extra time to gather all these screenshots — which may explain why I'd let these subscriptions continue for so long. By collecting the screenshots over several days and saving them in ChatGPT Projects until I was ready to act, the process felt much more manageable.For every subscription, take screenshots. Mine included: Apple One, Amazon Prime, Audible, Kindle Unlimited, Peacock (just upgraded for the World Cup), Google One, ChatGPT Plus, Claude Pro and Meta.Step 2: Paste everything into ChatGPTOnce you have a complete list, use a prompt like this: "I want to reduce my monthly subscription spending. Here is a list of all my subscriptions and their monthly costs: [paste list here]. Calculate my monthly and annual spending by identifying any overlapping services, flag subscriptions I may not be fully using, categorize each as Keep, Investigate or Cancel, estimate how much I could save annually and explain your reasoning for each recommendation"ChatGPT will quickly organize everything into a readable audit. And, if you have Memory enabled, Dreaming will actually help put the pieces together to determine if those are subscriptions you truly need.Step 3: Look for overlapsThis is where the biggest savings often hide. For example, paying for both Apple One and Google One storage or subscribing to Audible plus Kindle Unlimited. Multiple streaming services that aren't being fully utilized or having several AI subscriptions serving similar purposes will all be flagged.Get instant access to breaking news, the hottest reviews, great deals and helpful tips.In my case, ChatGPT immediately flagged a few subscriptions worth investigating because they provided similar benefits.That doesn't automatically mean cancel them, but it does reveal where you're possibly paying twice for convenience.Step 4: Ask ChatGPT tough questions
