How I Use ChatGPT as a Buy, Don’t Buy or Wishlist Assistant

I do not usually struggle with obviously reckless purchases.

My problem is the grey area.

It is the attractive item that I can afford, might enjoy and do not strictly need.

It might be:

• another version of something I already own
• a limited-edition record
• a useful-looking subscription
• a piece of technology that promises to simplify something
• a hobby item I can imagine using
• an interesting object that would be nice to have

None of these purchases would necessarily cause serious financial damage.

But repeatedly buying things that are merely “quite nice” still costs money, takes up space and creates more possessions to manage.

A normal wishlist did not completely solve this for me. It gave me somewhere to save items, but it did not help me decide whether they deserved to stay there.

So I started using ChatGPT as a purchase decision assistant.

I give it the details of the item, explain why I want it and ask it to place the purchase into one of three categories:

• Buy
• Don’t buy
• Wishlist for later

The purpose is not to let AI control my spending.

It is to slow the decision down, challenge my reasoning and expose whether I want the item itself or simply enjoy the idea of owning it.

Why a wishlist was not enough

My original wishlist was just an Apple Note containing product names and links.

That was better than buying everything immediately, but it had a weakness: items could sit there indefinitely without being properly evaluated.

A wishlist can easily become a waiting room for purchases that have already been emotionally approved.

Instead of asking whether I should buy the item, I would gradually shift toward asking when I should buy it.

The list also did not record:

• why I wanted the item
• what problem it would solve
• whether I already owned an alternative
• how often I expected to use it
• what made me hesitate
• whether I had reconsidered it before

ChatGPT helps turn the wishlist from a storage list into a decision process.

The three possible outcomes

I keep the system deliberately simple.

Buy

The purchase solves a genuine current problem, offers reasonable value and is likely to be used.

“Buy” does not mean the item is essential. Enjoyment can be a valid reason to spend money.

It means that, considering my circumstances, there is a strong enough case to proceed.

Don’t buy

The item is too redundant, too expensive for its likely use, driven mainly by impulse or unlikely to add enough value.

This category is useful because it creates a clear decision.

Without it, I can waste mental energy reconsidering the same item every few weeks.

Wishlist for later

The item has legitimate appeal, but there is not enough reason to buy it now.

That might be because:

• the price is too high
• I am uncertain how often I would use it
• I already own something similar
• I want to see whether the interest lasts
• I am waiting for a particular occasion
• the purchase would make more sense after another change
• there may be a sale or better version later

“Wishlist” should not mean “I want this, so I will probably buy it eventually.”

It should mean there is a specific reason to reconsider the purchase later.

What I tell ChatGPT

The result is only useful when I provide enough context.

Simply asking:

Should I buy this?

usually produces a generic response.

Instead, I include:

• what the item is
• the price
• why it appeals to me
• what I already own
• what problem it would solve
• how often I expect to use it
• whether it has ongoing costs
• whether storage or maintenance is involved
• any emotional or sentimental value
• my main reason for hesitating

For example:

I am considering a small folding magnetic chess set. I already own a full-size wooden chess set and a ChessUp electronic board. The smaller set appeals to me because it looks attractive and could be used for travel, but I do not currently travel with a chess set and would probably still play most games online or on ChessUp. It costs approximately $150. I like the idea of owning it, but I am unsure how much I would actually use it.

That gives ChatGPT something meaningful to assess.

The prompt I use

Here is the full prompt:

Help me decide whether this purchase belongs in one of three categories:

- Buy
- Don’t buy
- Wishlist for later

Please consider:

- whether it solves a real current problem
- what I already own that serves the same purpose
- how often I am realistically likely to use it
- its price relative to the value it would add
- whether I want the item itself or mainly enjoy the idea of owning it
- storage, maintenance or ongoing subscription costs
- whether there is any urgency to purchase it
- whether waiting would improve the decision
- any genuine enjoyment, sentimental value or quality-of-life benefit

Challenge my reasoning rather than simply agreeing with me.

Please give me:

1. Your recommended category.
2. The strongest argument for buying it.
3. The strongest argument against buying it.
4. Any assumptions I may be making.
5. A clear condition under which I should reconsider the decision.

Here are the details:

[DESCRIBE THE ITEM, PRICE, EXISTING ALTERNATIVES AND WHY YOU WANT IT]

The line that matters most is:

Challenge my reasoning rather than simply agreeing with me.

Without that instruction, ChatGPT can become overly supportive. It may simply repeat my own justification back to me in more polished language.

I want it to test the decision, not validate it automatically.

Example one: the folding magnetic chess set

One item I considered was a small, high-quality folding magnetic chess set.

It looked beautiful and seemed like the kind of object I would enjoy owning.

However, I already had:

• a full-size wooden chess set
• a ChessUp electronic chessboard
• access to online chess on my phone and computer

The smaller set offered portability, but I did not have an established habit of taking a chess set when travelling.

The strongest argument for buying it was that it was a well-made hobby item that could add enjoyment and be convenient for travel.

The strongest argument against it was that I was buying for an imagined future use rather than an existing need.

ChatGPT helped make the duplication obvious.

The most accurate category was:

Wishlist for later—or don’t buy unless a real travel use emerges.

A sensible reconsideration condition was:

Revisit the purchase after an upcoming trip only if I genuinely wished I had taken a physical chess set.

That is more useful than leaving it indefinitely on a vague wishlist.

Example two: upgrading iCloud storage

Another purchase looked less exciting: paying a small monthly fee for additional iCloud storage.

I had remained on the free storage tier, but it had become full. That was affecting services I actually relied on, including Apple Notes syncing.

My hesitation came from not wanting another recurring subscription.

However, the decision looked different when assessed against the real problem.

The upgrade:

• solved an existing issue
• restored useful syncing
• cost relatively little
• required no storage or maintenance
• supported tools I used regularly
• removed time spent repeatedly trying to stay under the free limit

This belonged in the Buy category.

The relevant comparison was not:

Free versus paid storage.

It was:

A small monthly payment versus ongoing inconvenience and unreliable syncing.

ChatGPT did not reveal anything magical here. It simply helped frame the decision around the actual value rather than my general dislike of subscriptions.

Example three: limited-edition vinyl

Collectibles are more complicated because utility is not the only source of value.

I considered buying limited vinyl pressings of albums I already owned on CD.

Two records could appear similar on paper:

• both were albums I already owned
• neither solved a practical problem
• both were discretionary purchases
• both involved some degree of nostalgia

But they did not have equal personal value.

One album was enjoyable and nostalgic, but I was unlikely to play it often. The limited colour pressing and low production number created much of the urgency.

The other was one of my favourite albums and something I could genuinely imagine playing on vinyl.

ChatGPT helped separate:

• wanting a specific album in a format I would enjoy
• wanting a scarce object because it might disappear

The first item leaned toward Don’t buy or Wishlist.

The second had a stronger case for Buy, provided it fit within my discretionary spending.

The lesson was not that collectibles are wasteful.

It was that two emotionally appealing purchases can still deserve different decisions.

The questions that reveal the most

The basic prompt works well, but a few follow-up questions are particularly useful.

“What problem does this solve that is not already solved?”

This exposes duplication.

If I already own something that performs the same function, the new purchase needs to offer a meaningful improvement.

“Different” is not necessarily “better”.

“Am I buying for my current life or an imagined version of myself?”

This catches aspirational purchases.

Common examples include:

• equipment for a hobby I plan to start
• travel products for trips I rarely take
• kitchen equipment for meals I do not currently cook
• productivity tools for routines I have not established
• exercise equipment for a program I have not begun

The imagined use may eventually become real, but buying the object does not create the habit.

“Would I still want this if it were not discounted or limited?”

This helps identify artificial urgency.

A sale can make a purchase cheaper, but it does not make an unnecessary product useful.

Likewise, limited availability can intensify desire without changing how much value the item would add.

“What would make this an obvious yes?”

Sometimes the answer reveals that the item belongs on the wishlist.

For example:

• a lower price
• an upcoming trip
• replacing something that breaks
• reaching a savings goal
• proving that I will use the underlying habit
• freeing suitable storage space

A clear condition is more useful than a vague promise to “think about it”.

“What am I giving up by buying this?”

The opportunity cost is not always another product.

It may be:

• savings
• physical space
• mental clutter
• another subscription to monitor
• time spent setting it up
• attention diverted from what I already own

A $50 purchase may be financially minor while still adding another object that needs to be stored and eventually decluttered.

ChatGPT is especially useful when I am emotionally invested

The less I care about an item, the easier the decision usually is.

The difficult purchases are often connected to:

• nostalgia
• identity
• collecting
• hobbies
• self-improvement
• imagined future experiences
• fear of missing out

These do not make the purchase irrational.

But they make it easier to build a convincing argument around something I already want.

ChatGPT creates a small amount of distance between the feeling and the decision.

It can say, in effect:

You clearly like this, but most of your reasoning is about scarcity and imagined use rather than the value it would add now.

I may still choose to buy it.

The difference is that I am doing so consciously.

Where ChatGPT can get the decision wrong

ChatGPT is not a financial adviser, and it does not understand my life unless I explain it.

Its recommendation may be poor if I omit:

• debt or savings priorities
• upcoming expenses
• how much disposable income I have
• existing possessions
• the emotional importance of the item
• household constraints
• how often I genuinely use similar products

It can also overvalue practicality.

A purely utilitarian analysis might conclude that art, music, collectibles or hobby items are unnecessary because they do not solve a functional problem.

That misses the fact that enjoyment has value.

The better question is not always:

Do I need this?

It may be:

Is the enjoyment this provides worth the price, space and trade-offs?

That is why I tell ChatGPT to consider genuine enjoyment and sentimental value rather than evaluating every purchase like a business case.

I do not give ChatGPT final authority

The output is advice, not permission.

I might disagree with the recommendation because:

• it underestimates personal meaning
• it does not understand my finances
• it assumes a cheaper substitute is equivalent
• it gives too much weight to efficiency
• I am comfortable paying for something simply because I like it

That is fine.

The system has still done its job if it helps me understand why I am making the decision.

My waiting rules

For purchases that land in the wishlist category, I use a waiting condition rather than an arbitrary delay wherever possible.

Examples include:

• reconsider after the next trip
• reconsider if the current item breaks
• reconsider after 30 days
• reconsider when the price falls below a set amount
• reconsider after using the related hobby consistently
• reconsider for a birthday or Christmas
• reconsider after clearing suitable storage space

This makes the wishlist more useful.

An item can be removed when the condition is met and the interest has disappeared.

It can also be purchased confidently when the condition is met and the case still holds.

What I record in my wishlist

Instead of keeping only the product name and link, I now prefer to record:

• Item
• Price
• Why I want it
• Recommended category
• Reason for waiting
• Review condition or date
• Link

For example:

Item: Folding magnetic chess set
Price: Approximately $150
Why I want it: Attractive, portable and connected to a hobby I enjoy
Decision: Wishlist
Reason for waiting: Duplicates existing chess sets and travel use is hypothetical
Review condition: Reconsider after a trip where I genuinely wished I had one
Link: [Product URL]

This stops me from reopening the same decision without remembering why I previously chose to wait.

A shorter prompt for quick decisions

For less expensive purchases, I use a simpler version:

Help me decide whether this is a Buy, Don’t Buy or Wishlist purchase.

Challenge my reasoning and consider:

- what problem it solves
- what I already own
- likely frequency of use
- price
- ongoing cost or clutter
- whether urgency is genuine
- whether I want the item or the idea of owning it

Give me a clear recommendation and one condition that would justify reconsidering it.

Purchase details:

[PASTE DETAILS HERE]

This is often enough for a quick decision.

The real benefit is reducing repeated decisions

The most useful result is not always saving money.

It is closing the mental loop.

Without a clear decision, I may:

• leave the browser tab open
• revisit the product repeatedly
• watch reviews
• compare prices
• check whether stock is running out
• keep debating a relatively minor purchase

That attention has a cost.

A well-reasoned Don’t buy lets me stop thinking about it.

A clear Wishlist gives me permission to defer it.

A justified Buy lets me proceed without unnecessary guilt.

Final thoughts

ChatGPT does not make my purchasing decisions for me.

It helps expose the reasoning underneath them.

Sometimes that confirms that a purchase is worthwhile.

Sometimes it makes the duplication obvious.

Sometimes it reveals that I am responding more to scarcity, novelty or an imagined future use than to the item’s actual value.

And sometimes the honest answer is simply:

I like this. I do not need it, but I would enjoy owning it, and I am comfortable with the trade-off.

That can still be a valid decision.

The aim is not to remove enjoyment from spending.

It is to make sure the things I buy deserve the money, space and attention they require.