rewards-optimizer

Rewards Optimizer

Reward programs are designed to be confusing so most value goes unclaimed. This cuts through it: given the cards and programs you actually have, it tells you the best one to use for a specific purchase or builds a simple by-category cheat-sheet for everyday spending — while keeping the golden rule front and center: rewards are only worth it if you pay in full and don't spend more to earn them.

What This Skill Produces

• The best route for this spend — which of your cards/programs earns most for the specific purchase or category
• An everyday cheat-sheet — a simple "use card X for groceries, Y for dining, Z for everything else" map
• Redemption tips — how to get the most value when cashing in (transfer partners, statement credit vs travel, avoiding devaluation)
• Guardrails — pay-in-full always, don't chase sign-ups into debt, keep it simple enough to actually follow
• A "worth it?" check — when an annual fee or a new card does or doesn't pay off for your spending

Required Inputs

Ask for these if not provided:

• Your cards/programs — what you have (issuers, categories, any annual fees)
• The question — a specific purchase/category, or optimizing everyday spending
• Your spending shape — rough monthly by category (groceries, dining, travel, gas, bills)
• Redemption goal — cashback, travel, or points flexibility
• Complexity tolerance — max value vs. keep-it-simple

Framework: Value First, Never Into Debt

1. Match the card to the category. Use whichever card earns the highest rate for that specific spend — bonus categories are where the value is.
2. Keep the everyday map simple. A two-or-three-card routine most people can actually remember beats a 10-card optimization nobody follows.
3. Redeem smartly. Points aren't all worth the same — flag high-value redemptions and watch for devaluation; sometimes plain cashback wins.
4. Judge fees honestly. An annual fee only pays off if your spending in its categories clears the fee in rewards — do that math.
5. Guardrail hard. Rewards are worthless if you carry a balance or overspend to earn them — pay in full, don't chase. Say this plainly.

Output Format

Rewards: [specific spend / everyday] · cards: [yours]

For this purchase: use [card] — earns [rate/value] because [category bonus].

Everyday cheat-sheet

| Category | Best card | Why |

|---|---|---|

| Groceries | [card] | [rate] |

| Dining | [card] | [rate] |

| Everything else | [card] | [base rate] |

Redeem for max value: [best redemption path + watch-outs].

Fee check: [card] fee pays off if you spend ~[x] in [category].

> Not financial advice. Only worth it if you pay the balance in full every month and don't spend more to earn rewards.

Quality Checks

• [ ] Recommends the highest-earning card for the actual category
• [ ] Everyday cheat-sheet is simple enough to follow
• [ ] Includes redemption-value guidance, not just earning
• [ ] Does honest annual-fee math
• [ ] Leads with pay-in-full / don't-overspend guardrails
• [ ] Uses only the cards/programs the person has

Anti-Patterns

• Optimizing into complexity nobody will follow.
• Ignoring the pay-in-full rule — interest erases all rewards.
• Encouraging spend to hit bonuses.
• Treating all points as equal value.
• Recommending a fee card without the break-even math.

Example Trigger Phrases

• "Which card should I use for booking a flight?"
• "Help me maximize my cashback across my cards."
• "Best card for groceries and dining from what I have?"
• "Is this card's annual fee worth it for my spending?"
• "Set me up a simple system for which card to use where."