Last month, my boyfriend and I took a weekend trip to Seattle to celebrate our anniversary. We got a great deal on a hotel using a discount app. We’d stayed at this hotel before, and the view was gorgeous. The price was also reasonable and the room was clean. We checked in, unloaded our bags and pulled back the curtains, preparing to take in Seattle’s beautiful skyline, which we’d flown a thousand miles to see.
Lo and behold, the parking lot. A man getting into his car looked up at us, startled.
“Eh,” I said. “We didn’t come here to hang out at the hotel.”
“Yeah, but I want a view,” Brian said, drawing the curtains. “The parking lot? C’mon.”
He vowed to talk to someone at the front desk and see how much it would cost to get a better room. We were surprised when the hotel receptionist said it would be no problem to upgrade us free of charge. There was no hesitation. It was the easiest upgrade I’ve ever gotten. We went up to our new room, opened the curtains and took in a nice nighttime view of the Space Needle.
This experience reminded me of just how effective speaking up can be. I’ve always struggled with speaking up for myself. But the more I see how speaking up can get you discounts, upgrades, necessary help, jobs, etc., the more I’m trying to master it.
Why speaking up was hard for me

Embarrassment
I grew up learning to be very independent and self-sufficient, and it took me a while to understand the cliché: the squeaky wheel gets the grease.
That cliche began to make the most sense when I entered the working world. My outspoken co-workers would get the projects I wanted just because they made sure it was known that they wanted those projects. Luckily, my boss was nurturing. She recognized my meekness and encouraged me to speak up when I wanted something. I realized I was embarrassed to ask for things. I felt like if I had the guts to ask for a project, it meant I was full of myself, and that was embarrassing to me. (Weird, I know. I guess I had an odd cultural upbringing.) When I had to ask for help in school, I always felt it meant I wasn’t smart and couldn’t handle things on my own. As an adult, that embarrassment turned into feeling like I was just being a nuisance.
Lack of confidence
It took me a while to ask for a raise or promotion on my own. I felt like, if I deserved something, it would just come to me. Silly, right? Another example: When I was a financial mess, I got into problems with overdraft fees. It was totally my fault, but the bank definitely preyed on my financial irresponsibility, charging me $35 per transaction, and sneakily posting withdrawals before deposits that were made early that same day. A friend told me I could call and have the fees removed, but I resigned myself to the belief that I deserved to pay them because, y’know, bank fees are all about personal conviction and morals and stuff.
Laziness
It hurts to confess this, but when I was a financial mess, I also stupidly fell for a free credit score scam. The company charged my card an unauthorized $14.99 fee. After researching the scam online, I knew if I called my credit card company and told them the issue, the fee would most likely be removed. But at the time, I told myself, “Eh, it’s just 15 bucks.” Then I asked my lazy self, “If someone paid you $15 to have a five-minute phone call right now, would you do it?” I answered yes, and I picked up the phone.
Speaking up in action
It’s still hard sometimes, but I’ve learned to speak up for myself a lot more these days. And it’s been really effective in saving me money, or even helping me to earn more money. The other day, I randomly called my cell phone provider about lowering my bill. I saw a better, cheaper plan online. The only catch — there was some crazy $150 fee for activating this plan. It would take seven months before I would even start seeing savings. So I called and half-jokingly asked, “I don’t have to pay that, right?”
The customer service rep said, “Sure, we can waive that.”
Well, that was easy! By just asking, I was able to lower my phone bill by $15 a month.
“Just asking” is one of the simplest but most effective money hacks I’ve come across. And the more I see how effective it can be, the less shy I become about speaking up. But, of course, there are a few things to keep in mind for better results:
Be nice
Pretty simple. I think people are more apt to offer help when someone is kind. Sure, customers who raise hell might get what they want, and being too nice can certainly work against you. But I’ve been nasty to customer service reps, and then I’ve been patient and kind to them. I’ve learned that, most of the time, nice usually trumps nasty. Since making it a point to be nicer and more understanding, I’ve found that my customer service calls are quicker and more effective.
Get personal
I’ve found that it usually helps, when asking for something, to remind people that you’re human. When arguing for a raise, I reminded my boss that my financial situation was suffering due to inflation — rent increases and the like. When calling my Internet company about their price hikes, I reminded them that I don’t have the money to pay for such a huge increase. “Times are tough,” I told the rep.
She sighed, “Yeah, I understand.”
It took some work, but I was able to get an even better deal on my Internet because of some special promo or whatever they had going on.
Be persistent
Sometimes, however, it ain’t easy. While I wouldn’t be annoyingly persistent in asking for something like a free room upgrade, I was annoyingly persistent with those aforementioned bank fees (especially when they once were at $300). When I finally decided to call, I asked to talk to a manager, and it took nearly an hour of my time and a lot of headache in arguing my case for waiving the fees, but in the end, “just asking” won.
Of course, there’s a difference between asking for something appropriate and then asking for a handout. And this is kind of what I struggle with. Blatantly asking for a free flight upgrade, for example, seems so embarrassing, yet I still want to try it, because others have said it works. And then I’ve met people who aren’t afraid to “just ask” for damn near everything, to the point that their irreverence borders on cheapskate. When I’m asking for help or for a discount or something, I try to imagine how the other party feels when I’m speaking up — will they feel put out or taken advantage of? If so, then I think twice about asking.
But I’m not quite sure where to draw that line, so what do you think? Speaking up works, but where’s the boundary between being outspoken and just being cheap?