The Confidence to Ask: How Negotiating Builds More Than Just Savings
“The best outcome is discovering that self-advocacy builds both savings and confidence.”
This article is part of an ongoing series exploring the Four Facets of Better Living: Physical, Personal, Professional, and Prosperity Progress. Each facet is a pillar in the Resilience for Progress framework and represents a key area of fulfillment, helping us grow stronger and more grounded in the way we live, work, and care for ourselves. This article focuses on Prosperity Progress, which centers on financial confidence and peace of mind.
Money conversations can feel uncomfortable, especially when it means asking for a better deal. But negotiating isn’t about confrontation or greed. It’s about confidence and remembering that every financial decision reflects how much you value your time and effort.
When my husband and I bought his car, the dealership wouldn’t negotiate the price due to limited inventory, but we still found room for progress. My husband chuckled with mild embarrassment as I greeted their finance specialist with a firm handshake and said, “Sir, I have one question for you: are you in the business of making dreams come true?” If you know me, you know that kind of lighthearted opener is exactly the thing I’d say to a stranger. It made my next questions feel non-threatening and set a friendly tone. I explained that we were determined to buy the car but needed a better offer, so we asked for a stronger trade-in value, which he got approved by management. I also convinced him to include a complimentary dealer service package, saving us the cost of early routine maintenance.
By negotiating around the edges of the car-buying experience, we saved money and left happy. As we walked out, my husband shook his head, smiling, and said, “And this is why I love you.” It was a reminder that “no” in one area doesn’t mean “no” everywhere.
When we added my sons’ used car to our insurance, I was surprised to learn that adding on an older, higher-mileage vehicle can reduce your overall rate even though the policy now has more vehicles. While on the call, we also found other savings: a discount for their good grades and lower annual mileage estimates for all our cars. That quick call took minutes but lowered our premium for the year.
Sometimes simply asking about available discounts or quoting a competitor’s price can lead to real savings. When I worked in cable, we had a retention team with special “save” offers for customers who said they might cancel. It turns out companies often expect these conversations more than we realize.
A few months ago, I asked my financial advisor to review his management fees. It felt like a gutsy ask, but I began by requesting an illustration of the annual costs. That opened an honest discussion about the service I was receiving for my mostly “set it and forget it” investments. Using my same playful tone, I told him, “If I’m going to stand in the grocery store and decide whether the generic shredded cheese is worth a dollar in savings, I should be thoughtful about my bigger expenses.” That one ask will save me a meaningful amount each year and reminded me that sometimes progress isn’t about earning more; it’s about keeping more of what we already have.
Negotiating can take many forms, from calling your cell phone provider to ask about loyalty discounts to reviewing subscriptions and trimming what you no longer use. If it feels intimidating, start small by choosing one expense and asking if there’s a better rate or plan available. The worst outcome is hearing “no.” The best outcome is discovering that self-advocacy builds both savings and confidence.