Ep. 24 – Is It Worth It to Pay for ChatGPT?

ByMaestro

Curious Reader!

Welcome to this week’s Curious Companion newsletter.

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In this episode I break down whether it’s actually worth paying for ChatGPT or sticking with the free tier. I walk through the concrete differences between free and Plus, talk honestly about what matters and what doesn’t, and explain why “worth it” is always subjective. This episode is less about convincing you and more about giving you enough clarity to decide for yourself.

“Worth it.”

So, this is a topic that I’ve kinda avoided making a specific episode about for some time now, mainly because I ain’t no big-AI schill.

Like, we know that some of the worst folks are in leading these companies, namely Sam Altman. Dude is fucking weird, and no, I do not for one second think that he has humanity’s best interest at heart.

I think for many folks when they think about paying for an AI model it starts to be an internal ethical debate, which I get. So after having yet another discussion with a good friend of mine during which she asked if I honestly thought it was worth it to pay for Chat, I figured I’d make this episode.

Worth noting, I started paying for ChatGPT in very early 2024; I honestly don’t remember what it was like before then. Point being I can’t speak from my own personal before and after experience as it relates to being “worth it”. I can only say with full certainty that right now at this moment in time it is absolutely worth it for me to pay for it. This note matters because “worth it” will always be subjective, and wholly dependent on what matters to you.

Free vs Plus vs Immediately Fucking No

To keep things as objective as possible, let me outline the differences between the tiers.

There’s the free tier, obviously free. Then there’s Plus at $20 a month. Then there’s Pro at $200 a month.

Immediately fucking no to that $200/month tier.

My friend Khe tried Pro for a bit, and I absolutely was not convinced it was worth it. I don’t think he was either. So for the purposes of this episode, we’re only talking about free versus Plus.

Free tier gets you

  • Limited access to reasoning
  • Limited messages and uploads
  • Limited and slower image generation
  • Limited deep research
  • Limited memory and context
  • Projects

Plus, $20 tier gets you everything in free and:

  • Advanced reasoning with GPT-5.2 Thinking
  • Expanded messaging and uploads
  • Expanded and faster image creation
  • Expanded deep research and agent mode
  • Expanded memory and context
  • Projects, tasks and custom GPTs
  • Limited access to Sora 1 video generation
  • Codex agent

What Actually Matters for You

Here’s what I think will from that list will actually matter for you:

  • Access to better model: Especially helpful for more complex or research-oriented queries.
  • Expanded messaging and uploads: Throttle me not! According to my ChatGPT year in review (did you look at yours?) I am a top 1% user – this alone makes it well worth the $20/month for me. I’m not sure what the Plus limit is because even as a top 1% user, I’ve yet to hit it. A friend, Beth, reached out and said she got throttled not too long ago, but that was for image generation. Aside from that I have not heard from anyone on the Plus tier reaching a usage limit.
  • Expanded Memory + Context: Expanded memory and context are a big deal. Memory on the paid tier is stronger and deeper. It keeps more context for longer and uses a broader set of saved details to influence answers. The responses feel more personalized and more consistent across sessions.
  • Projects, Tasks, and CustomGPTs
    • Projects are available on the free tier, but you’re limited to 5 file uploads and you don’t have as strong of memory. On the Plus tier you have better memory and can upload up to 25 files per Project which can absolutely improve the quality and complexity of the Project.
    • Tasks are only available on the Plus tier. A task is where you can have ChatGPT execute actions for you on a schedule. I’ve used it to look for Nest Cam sales, DeWalt battery sales, and SSD sales. You define the task, ChatGPT runs independently on whatever schedule you set, and then it sends you an email.
    • Custom GPTs are another big perk of the Plus tier, and I’m a huge fan of them. Custom GPTs are basically a dope way to clone yourself and give other folks access to the computer version of you.

So…Is It Worth It?

So when we look at those categories:

  • Access to a better model
  • Basically unlimited messaging
  • Better memory
  • Access to Projects, tasks, and custom GPTs

…it is eleventy billion percent worth it for me to pay.

The question is do you care about any of those things?

If you don’t, then it’s not worth it for you to pay.

If you’re a super casual user asking it for a dinner recipe every now and then, or a health question every now and then, it’s probably not worth it.

If you’re reading this Companion episode (…like…you’re reading a newsletter about ChatGPT), honestly, it’s probably worth it.

I actually asked in one of the very early episodes to let me know if you paid for ChatGPT, and I think maybe one or two people got back to me. Shoutout to you Kate and Ali! I remain genuinely curious: Are you paying for ChatGPT?

No Pressure, No FOMO

I can think of two people off the top of my head who I know listen to this podcast who have recently started paying, and both have told me that it’s been worth it for them.

For both of them, I was actually really surprised to hear they weren’t paying before, mainly because of how I know they use it. IMO they would have benefitted from better memory, better Projects, and basically unlimited chats.

But they were making it work, and again, I’m not here to tell anyone that they should be paying for ChatGPT. Immediately no.

If you’re using it and it’s serving you well, keep on keeping on.

I’ve never really had a lot of FOMO or wondered if I’m missing something. But if that’s you, and you’re wondering, “Am I missing something?”, my answer is simple: Spend the $20 and see for yourself. If you don’t notice a difference, downgrade.

A Quick Bigger-Picture Note

The majority of users are on the free tier, and honestly, I don’t know what OpenAI is going to do about that long-term.

They’re not making money from most users, and I’m not sure how long they’ll be able to play the “we have the most users” card while continuing to get the funding they’re getting.

But, I don’t want this to become an economics episode, so Imma just say this: A few weeks ago, following the release of Gemini 3, Sam Altman declared a code red, which is basically short for “Oh shit, they’ve caught up, we gotta do something!” His instruction to the company was to focus on memory and personalization.

So maybe hang onto that free tier and see what gets thrown your way with the updates and rollouts. We’re already on version 5.2 (GPT-5 was rolled out on August 7th), and there are new features showing up in the personalization section.

How I Used ChatGPT This Week

Each episode I include a section where I briefly discuss how I used ChatGPT that week.

I’m currently using chat BIG TIME to learn about computer science and coding (I actually built a website for my brother last week. Whether or not he actually uses is another story, but I needed the practice.) and I cannot express how truly amazing I think ChatGPT (and LLMs in general) are for learning.

They never get annoyed with you!

Ask them as many questions as you want, ask them to explain things as many times as you want, and they will…if you are on the paid tier so you don’t hit those usage limits 😉

Da Wrap-up

So, there you have it. Paying for ChatGPT is eleventy billion percent worth it for me, but whether or not it will be worth it for you will be fully dependent on how you use it and what matters to you.

As always, endlessly appreciative for you and your curiosity.

Catch you next Thursday.

Maestro out.

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AI Disclaimer: In the spirit of transparency (if only we could get that from these tech companies), this email was generated with a very solid alley-oop from ChatGPT. I write super detailed outlines for every podcast episode (proof here), and then use ChatGPT to turn those into succinct, readable recaps that I lightly edit to produce these Curious Companions. Could I “write” it all by hand? Sure. Do I want to? Absolutely not. So instead, I let the robot do the work, so I can focus on the stuff that I actually enjoy doing and you get the content delivered to your digital doorstep, no Airpods required. High fives all around.

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