How to save 5% to 50% on everything

Most people treat the price tag as a rule of thumb. That’s not the case. In most cases, that number is just a suggestion—a “starting point” for discussion.

If you don’t negotiate your recurring bills, your big-ticket purchases, even your medical expenses, you’re essentially leaving a lot of money by the wayside.

I’ve spent years struggling with everything from hotel rooms to hospital bills, and I can tell you: “asking” works more often than not.

In fact, a 2025 survey found that nearly 60% of people who reached out to negotiate their medical bills got a lower price, and more than 90% were at least partially successful. That’s more than a coin’s chance of saving hundreds, if not thousands, of dollars.

Here are the golden rules for keeping that money in your pocket when it belongs to you.

What costs can you negotiate?

Short answer: almost anything where one has the power to change numbers.

1. Medical Bills: This is the big one. Between “coding” and simple human error, medical bills are notorious. Don’t just pay them. Ask for the specified bill first to spot errors such as duplicate charges. (See Master These 10 Negotiating Steps to Lower Your Medical Debt)

2. Monthly subscription: Your cable, Internet, and wireless providers are eager to save you. The cost of acquiring a new customer is much higher than the cost of giving you a $20 monthly discount. (See 7 Ways to Negotiate a Better Cable Package)

3. Major Purchases: When you buy electronics, furniture, or a car, the sticker price is just a dream. Even at retail stores, low-end models or low-scratch items are the targets for a 10% to 20% discount. (See Confessions of a Serial Haggler)

4. Credit Card Interest: If you’ve been a loyal customer and your credit score is decent, call your issuer and ask for a lower APR. They will usually waive it to prevent you from transferring your balance elsewhere.

5. Hotels: I can’t remember walking into a hotel and not asking for a better deal, on price or a free upgrade.

Negotiate more than just price

Sometimes the person on the other end of the line really can’t shake a dollar amount. That’s right. Don’t go yet. There is a whole world of “value” that is not reflected in the basic value.

1. Time and Delivery: If you’re buying furniture or a large appliance, ask them to throw in a free delivery or towing service for your old unit. That’s a “hidden savings” of $50 to $150.

2. Payment Terms: Can’t lower the price? Ask for an interest-free payment plan. Or, flip the text: offer to pay the full amount in cash now for a “quick payment” discount. Most medical providers will shave 10% to 20% off the total amount if you pay the bill right away.

3. Additions and Improvements: When booking a hotel, ask for a free room upgrade or late check-out at the front desk. The worst they can say is no, and in their off hours, they’re often happy to accommodate you to be nice.

What is the best time to strike?

Timing is everything in the covenant world. You want to negotiate when the seller is most vulnerable—or most motivated.

1. End of the Month: Many retailers have assignments. If two dice are short of a bonus on the 30th of the month, they will be more flexible than they were on the 1st.

2. The “Slow” Season: Try buying a lawn mower in October or a lawn mower in April. The lower the demand, the higher your potential.

3. Before Buying: For medical procedures, ask for an “insured price” or cost estimate before service. Once the service has been rendered, you are the debtor; before it is delivered, you are the customer. Customers always have more power.

The secret sauce: How to make a speech

You don’t have to be a “shark” to win. In fact, being a jerk is the fastest way to get “no”.

First, do your homework. Know what competitors are charging. If the dry cleaner down the street charges $2 for a shirt and yours costs $3, ask them to match it.

Second, find the right person. The teenager behind the fast food counter can’t change the prices. You need a manager or someone in the “inventory” (accounts) department who actually has the authority to click the “discount” button.

Finally, he accepted peace. Make your donation, then close. Let someone else fill in the awkward void. More often than not, they will come back with a counter offer that is better than the original price.

It may feel strange when you first do it. Get over it. That “weird” feeling is just the sound of money landing in your bank account.