Negotiating Tip #16: Use It or Lose It

What do you call someone who pays more than they should for a product, service, or home?

That’s a question worth sitting with—especially in high‑value transactions.

Negotiating skills are only valuable when they are actively used. Yet many otherwise capable, intelligent people hesitate to negotiate, even when the opportunity is clear. Why? In my experience, the reason is surprisingly consistent: the fear of being labeled “cheap.”

In American culture, negotiating for a better price is often misunderstood. Rather than being seen as prudent or strategic, it is sometimes met with subtle judgment. But let’s be clear—seeking value is not the same as being cheap. In fact, the opposite is often true.

Reframing the Myth of “Cheap”

I once participated in a radio talk show focused on negotiation and securing better deals. One of the guests was Annie Korzen, a comedy writer and actress known for her appearances on Seinfeld and the author of The Bargain Junkie: Living the Good Life on the Cheap.

Despite the lighthearted title, her perspective was insightful and grounded. She offered one of the clearest definitions I’ve ever heard:

“Cheap is a rich guy who’s a lousy tipper.”

That distinction matters. Being cheap is about withholding fairness. Negotiating, on the other hand, is about ensuring alignment between value and price—especially in complex or high‑stakes situations like real estate.

The Real Cost of Not Negotiating

Here’s the uncomfortable truth:
If you consistently pay more than you should—simply to avoid discomfort or judgment—you may deserve a label. And it’s far worse than “cheap.”

Successful professionals, investors, and homeowners share one critical trait: they are willing to challenge assumptions, ignore casual criticism, and advocate for themselves. They understand that negotiation is not confrontation—it is competence.

If you ever feel a moment of hesitation before asking for better terms, a stronger position, or a meaningful concession, recognize it for what it is: a habit that can be unlearned.

Those who might quietly judge you for negotiating are often reacting from envy, not insight.

Confidence Changes the Conversation

Highly effective negotiators are not deterred by fear of labels. Their confidence, preparation, and strategy move conversations forward—often earning them more respect, not less.

Whether you are negotiating a purchase, a contract, or a home in Palos Verdes, the principle is the same:

Value is rarely given. It is negotiated.

If you’re serious about improving outcomes—and avoiding costly mistakes—this is where guidance matters. Most people never learn these skills properly, and they pay for it over time.

And that’s exactly why I continue to share these negotiating insights. The real question is whether you want access to the ones most people never ask for.

Keep negotiating. And don’t leave leverage on the table.