Why Being Midwest Nice Can Cost You Real Money

Everyone who knows me knows that I am a proud Midwesterner. I adore “Midwest Nice.” The deep-rooted politeness that extends as far as our wide open spaces.

I love that we return the shopping cart. We lift two fingers off the wheel to wave when we pass a car on the highway. That we’d rather jump in a freezing cold lake than tell a server, “no, we actually aren’t enjoying the meal because we didn’t get the right one” (hey, it’s not their fault!).

Midwest Nice is a genuinely beautiful cultural inheritance. It’s also one I get to watch play out professionally, not just personally. As a financial advisor in Sioux Falls, South Dakota, I spend my days sitting across from fellow Midwesterners: people who show up early, bring cookies to the appointment, and apologize before asking a single question about their money. I see the good of Midwest Nice up close. I also see its blind spots.

Aggressive niceness can be an expensive habit.

Let me explain. Kindness itself doesn’t cost anything. What I mean is that there are certain tendencies woven into our Midwest Nice DNA, namely, an intense aversion to seeming too demanding, that can cost significant money across a lifetime.

Think about the messages many of us have internalized: Don’t make a fuss. Don’t talk about money. Be appreciative! Don’t seem greedy!

The cost of following those rules too closely is usually invisible, which is exactly why it’s easy to miss. You don’t see the raise you didn’t ask for. You don’t see the fee you didn’t question. You just quietly have less than you could have.

Here are four places I’ve seen it show up most often, so you can recognize the pattern and push back on it when it matters. Being good to the people around you doesn’t have to come at the cost of your own financial health and wellbeing.

1. The Family Money Conversation You Keep Putting Off

There’s a particular Midwestern silence that descends when someone tries to bring up estate plans, inheritance, or a parent’s long-term care plan.

You can imagine the moment: Someone forcefully pats their legs and stands up. “Ope,” they say, “I guess we’ve got plenty of time to talk about that later, we don’t need to worry about it today.” 

It feels harmless at the moment. But that little dodge is exactly how the real trouble can start. Avoiding the conversation doesn’t make the plan disappear. It just means no one finds out the details until it’s too late to ask questions. 

I’ve sat with families in their 50s who inherited a mess simply because no one talked about the plan out loud. Even when a plan technically exists on paper, gaps like these are common: no one knows where the documents are, beneficiary designations haven’t been updated in years, and family members carry different, unspoken assumptions about who’s supposed to get what. Untangling issues like these can take months or years and can rack up significant legal fees, on top of family strain that can outlast the money. The paperwork was fine. The silence around it wasn’t.

How to Broach the Conversation About Money with Your Family

The good news is that you don’t need a formal family meeting to start. One low-pressure question is often enough to crack the door open. “Hey, if something happened to you, would I know where to find your important documents?” The goal isn’t to solve everything in one conversation. It’s to normalize having the conversation at all. You don’t need every answer right away. You just need the door to stay open, because a single honest question today can spare your family months of confusion, legal costs, and unnecessary strain later.

This is Midwest Nice at its most well-intentioned and, potentially, its most costly. Nobody wants to seem like they’re rushing a parent toward the end, or like they’re eyeing an inheritance. But that same instinct to avoid discomfort now can sometimes create more discomfort later, for the people we were trying to protect in the first place. A little awkwardness today can be a small price to pay for more clarity down the road.

2. The Raise You Didn’t Ask For

Many of us Midwesterners were raised to believe that good work speaks for itself. Pull yourself up by your bootstraps. Be grateful for what you have. Asking for more feels like bad taste. Surely your employer will see you work hard and reward it in time. 

Some employers might, but I wouldn’t count on it. They’re not necessarily villains; they just might have a budget to keep, and you’re a line item on it. If you don’t ask for more, that’s one less thing they have to account for. If you’re the type of person who has been less-than-excited to negotiate salary, you’re not alone. I say this as a recovering member of the “just happy to be here” club myself.

How Much a Single Raise Negotiation Could Be Worth Over Time

Growing your income is one of the most powerful tools for building wealth. In many cases, it’s more powerful than cutting expenses since there’s a limit on how much you can cut, but more potential to grow what you earn. We trade our life energy for money at our jobs. It only makes sense to optimize that trade.

The answer depends on your specific salary and raise, but even a modest negotiation can add up to a meaningful amount in the first year, and potentially much more over time if that extra income is invested rather than spent.

Here’s what that can look like in practice: for illustrative purposes, let’s take a 40-year-old earning $150,000. If she negotiates a 10% raise at her next promotion instead of accepting the 2% her company had planned, that single conversation is worth about $12,000 in year one alone. A nicer paycheck, great! 

But here’s where it gets interesting: if she keeps living on her old salary of $150,000 and invests the difference instead of upgrading her lifestyle, and does this at each future raise, that one negotiation can compound into more than half a million dollars by retirement.* This is actually one place where the “be grateful for what you have” mentality might work in your favor. 

How to Find Out What You’re Worth, and What to Do About It

That kind of math is a good reason to negotiate when the moment comes. But knowing your worth isn’t only about what happens inside your current job. Your employer, and even your industry, isn’t the only buyer of your time and expertise. You don’t have to leave your job to find out what you’re worth, but being willing to look is a worthwhile exercise in itself. Once you have a sense of your market value, the real question becomes what you do with it. 

None of this means you need to become a ruthless negotiator or transform into someone you’re not. It just means treating your income the way you’d treat any other financial decision: worth a conversation, not something to accept quietly out of politeness. One negotiation, invested and left alone, can compound into meaningful money over time. Being nice about your paycheck might be the most expensive kind of nice there is.

3. The Sticker Price You Just…Paid 

Cars. Houses. Phone bills. Closing costs. Contractor estimates. Medical bills (yes, really. Negotiating with hospitals is a weird hobby of mine). Almost every large number you’ve ever paid was perhaps just a starting offer. Midwest Nice tells us that negotiating is tacky and that asking questions is “too much.” 

After having both of my babies, I saved hundreds of dollars just by asking for a “paid in full” discount. I saved thousands by asking the insurance company, in writing, whether my baby was covered under my existing deductible or if his birth would trigger a new one of his own. Then I held them to their word when they later tried to restart the deductible anyway.** Yes, I filed an insurance appeal when I was a month postpartum. Like I said, it’s a weird hobby. 

Now, it may not always be worth the time to ask for a discount or haggle over everything. Your time is valuable. But the next time you’re about to pay more than, say, $1,000, try asking, “Is there any flexibility here?” You might be surprised how often the answer is yes.

You don’t need to become a skilled negotiator or turn every purchase into a back-and-forth to save money. None of this requires becoming a haggler. It just means treating a price tag as a starting point rather than a final answer. Midwest Nice tells us that asking is impolite, but a polite question, asked plainly, isn’t offensive. The worst answer you can get is the one you were already planning to accept.

**This is a very unique and personal example. It’s always worth asking how your insurance plan handles any specific situation you’re in.

4. The Professional You’re Too Nice to Question

Midwest Nice doesn’t just show up with family and coworkers. It can show up with the people we pay for expert advice like financial advisors, real estate agents, lawyers, accountants, and contractors. We assume that asking questions means we don’t trust them, so we stay quiet instead, even when something feels off.

This one is personal for me, because as a financial advisor to Midwesterners, I’m one of the people you might feel too polite to push back on.

Speaking of Midwest sensibilities, that sentence was surprisingly hard to write. It felt presumptuous to describe myself that way, like I need to soften it with a few qualifiers and apologies first. (See? The whole piece, in one sentence.)

Why It’s Sometimes Hard to Question Professionals 

Many of us assume that questioning a professional means questioning their expertise, or worse, implying we don’t trust them. The professional class can default into operating from behind a desk, using specialized language that isn’t always easy to follow. That distance can make questions feel unwelcome, even when they aren’t. I work hard not to operate that way as a financial advisor. But Midwest Nice still might tell you it would be rude to ask any of us to slow down or explain further.

Please ask anyway.

If you don’t ask questions, you can end up paying fees you don’t understand or holding products that were never right for you in the first place, sometimes for years before anyone catches it. Staying quiet doesn’t protect the relationship. It can just delay finding out if something is wrong.

I have had clients hand me statements from previous advisors showing fees they didn’t understand attached to products that weren’t appropriate for them. Even when they had a hunch something wasn’t a good fit, the reason they didn’t make a change sooner was pure Midwest Nice: “He seemed like a nice guy. I didn’t want to seem like I didn’t trust him.”

The cost of staying quiet isn’t always just financial. It can also mean staying longer than you should in a relationship that wasn’t fully serving you. A good advisor relationship should feel collaborative, where questions are welcomed and explanations are offered before you have to ask twice. Credentials matter, but so does feeling comfortable enough to speak up. Finding someone you feel genuinely comfortable with can be worth prioritizing.

Questions to Ask Any Financial Advisor or Other Professional

A few simple questions can reveal a lot about a professional, like how they’re paid, what they’d genuinely recommend, and what the drawbacks of their advice might be. A good professional, in any field, should welcome your questions and appreciate the thoughtfulness, rather than deflect them. Try asking: 

• “Can you walk me through how you’re paid?” 
• “What would you recommend if I were your family member?” 
• “What are the drawbacks of this?” 

These are the questions that can help protect your money.

What Midwest Nice Can Cost You Over Time

Being overly polite about money can cost you unasked-for raises, unnegotiated purchases, unchallenged fees, and unresolved family conversations, all of which can add up over a lifetime. Across these four everyday situations, we can see the pattern of staying quiet to avoid seeming pushy, ungrateful, or distrustful and quietly paying for it later. 

Asking these questions doesn’t mean becoming someone you’re not. You don’t have to get loud or aggressive. You don’t have to stop being the person who holds the door for way too long for the gal who’s 30 yards away. You just have to be willing to ask one or two potentially uncomfortable questions. And, trust me, speaking from experience, it gets easier with practice.

If you’d like a second set of eyes on where Midwest Nice might be showing up in your own financial life (whether you’re in Sioux Falls, the Twin Cities, or anywhere else), book a call, and let’s take a look together. I’ve let politeness drive for longer than it needed to, too. 

I believe the most generous thing you can do, for yourself and for the people counting on you, is to value your own financial wellbeing as much as you value being kind to everyone else.