How You Respond to Money Mistakes

One of the things I love to do at night to unwind is turn on a TV show. It could be a mindless reality show, the nightly news, or something on Bravo or HGTV. It’s funny because cable is a nonnegotiable item in our budget. More than once Winston has said to me, “Can’t we just be normal millennials and stream everything?” But I just can’t. For me, the DVR is a must for the shows I miss, plus it lets me fast-forward through commercials. Cable gives me options.

The other thing I love—and most people cringe at this—is politics. I love the job I have now, obviously. But if there was an alternate universe, I’d be living in Manhattan, working as a political correspondent for a news channel and making frequent trips to Washington, DC, for special reports. (PS: That will never happen, so don’t worry, Winston!) I love election season and watch all the coverage. I’m probably the only person in the world who enjoys campaign commercials. I watch every debate, and then stay up into the wee hours of the night watching voting results come in. I find it thrilling.

My friends know about my twin passions for cable and politics, so recently a friend recommended that I watch a documentary on Anthony Weiner, a former congressman from New York who faced a huge scandal. A few years later, he ran for mayor of New York City. My friend said the documentary followed him through his mayoral run and through all the ins and outs of his campaign. This camera crew had insider access throughout the campaign, and during filming mid-campaign, another scandal broke out. This was some terrible stuff, but for some reason, Weiner continued to let the cameras roll. So the documentary shows the scandal breaking in real time and what he, his wife, and his team were doing to try to downplay and fix it. My friend promised this was drama on an epic scale.

So one afternoon while my girls were napping, I decided to find the documentary and watch it. It was available on demand through our cable provider. Renting it cost $19.99—a pretty hefty fee for a rental. But my heart was set on seeing it! I figured we’d pay that much to see it in a theater, and this way, we didn’t even need to pay a babysitter. I bit the bullet and mentally put that $19.99 in the “Rachel” line item of our budget. Needless to say, I watched it and it was fantastic! I didn’t think much about it again until a few weeks later.

One night I came home from work, and Winston was already there. He was in the kitchen on his phone looking very frustrated. I heard him say, “No. We are not paying for that. You guys do this to us almost every month, adding extra fees or jacking up your prices . . . so, no.”

There was a pause, so I whispered to him, “Who are you talking to?”

He looked at me, rolling his eyes. “The cable company,” he whispered.

Oh, I knew this conversation well. Winston and the cable company go at it at least three times a year about our bill. He kept shaking his head in frustration and then blurted out, “No! We did not rent a video called Weiner!”

Oh, the horror! I looked at Winston with wide eyes and started panicking. I began nodding my head wildly. “Yes! Yes, I did! I rented that! That title sounds awful, but it was about politics! An election!”

Winston paused to take in my unexpected confession and then sheepishly replied to the customer service rep, “I’m sorry. My mistake. My wife actually rented Weiner.”

Just hearing him say it out loud was embarrassing and hysterical all at the same time! I started shouting so the person on the other end of the phone could hear: “It’s a documentary about a former congressman running for mayor of New York City!”

Winston quickly ended the call and started laughing. “Babe, why didn’t you tell me?” he asked.

I told him I’d honestly forgotten. Plus—shout out to my free spirits here!—who looks over a cable bill that closely anyway? (I’m so not the detailed one in our marriage.)

As you can imagine, we had a really good laugh about the whole thing.

Why did I share that? Because Winston and I have been managing our money together for over a decade, and we still mess up. Things go wrong. We forget to communicate about a purchase. Life doesn’t always work out the way we plan. Thankfully, because we’re intentional, when we make mistakes they’re usually not that costly, emotionally or otherwise. We’re proactive and regularly work together on our money. But life still happens, and it affects our money and relationships.

This is true for all of us. Every single one of us makes mistakes with our money. Some are small, like forgetting to sign a check or misplacing cash or forgetting to pay a bill on time. Some are larger, more expensive mistakes like overspending on Christmas gifts or buying a car you really can’t afford. And some happen to you—like when someone charges you incorrectly on a bill. Each mistake requires a response, but most people don’t stop to think about how they respond or how it affects them. Instead, most people respond automatically or because it’s what they feel like they should do. And while not all money mistakes will cost you a lot of money, you can pay a tremendous price in your relationships—both with yourself and with others. So in addition to your childhood, reflecting on your childhood money classroom, identifying your unique money tendencies, and overcoming your money fears, it’s important that you understand how you respond to money mistakes—because no one is perfect and mistakes are going to happen.

The Grace Scale

Think about the last time you faced a money mistake, whether it was your own mistake or a mistake someone else made that impacted you. How did you react? Did you write it off as something that couldn’t be helped? Did you roll your eyes, annoyed by it? Did you obsess over it for days and weeks?

When facing money mistakes, we can sometimes respond either by giving too much grace or by not giving enough grace. When we extend too much grace, forgiveness and compassion flow freely, but the injured party still gets hurt and no one learns a better way. When we extend too little grace, there’s tough love and by-the-book living but little heart or humility. So where are you? Keep in mind, depending on the situation, you can flip-flop between sides.

The Grace Scale

When You Give Too Much Grace

We all like to be the recipient of grace—to have a soft place to land when we fall. Those who respond gracefully are those we love to run to when we’ve made a mistake. They are generous, kind, and forgiving. There’s a lot of empathy and compassion. But it can go too far when we’re talking about money.

As we talk about giving too much grace in response to money mistakes, remember we’re not talking about too much grace when it comes to sin. As a Christian, I can hear some of my fellow brothers and sisters out there saying, “Rachel, there is an endless amount of grace!” And that is true—thank you, Jesus—when we’re talking about salvation. But when we’re talking about our response to money mistakes, it’s possible to extend so much grace that we end up hurting the people involved.

So how can too much grace hurt people? I’m going to illustrate this by using the extremes of the grace scale. Obviously, not everyone is going to fall in one of the extremes, but I would encourage you to read these descriptions carefully. The tricky thing is most people have no idea that how they respond to money mistakes can actually do more harm than good. So read closely and take an honest look at your behavior. You may discover you’re unintentionally hurting the people you love the most.

The extreme of giving too much grace is . . . enabling. I know, it’s a hard word to swallow. An enabler is someone who “enables another to persist in self-destructive habits by providing excuses or by making it possible to avoid the consequences of such behavior.”¹⁴ Enablers extend grace upon grace and chance after chance to the people in their lives. There is no end to their belief that the person they’re helping is trying and will do better the next time. They have the best of intentions to really help people and love people well. If you see an overweight dog, you can probably bet its owner is an enabler. They have a hard time saying no even to their pets!

When a bill is paid late and a late fee is tacked on the next month, they say, “Oh, well.” And when the late fees start to stack up and they don’t have enough money for groceries, out comes the credit card with an easy tug. “It happens!” they say, believing next month will go better. The allowances are unending and there’s no course correction for the problem.

Enablers make lots of room for money mistakes, but unfortunately, it’s often to their own detriment. They don’t usually have boundaries and rarely take a stand. Their great fear is being mean, which makes it easy for others to take advantage of them. They can also feel so badly about something from the past that they overcompensate for it in the present.

It’s so important for enablers to recognize when their help has stopped helping and is now harming—and it’s often very hard for them to see. But in an enabling situation, more help is like letting an alcoholic have a drink. The enabler is actually encouraging and prolonging the disease. It can be easy to spot an enabling situation between other people, but we need to first address that some of us enable ourselves. And when it comes to money, it really comes down to excuses.

Here are some excuses I hear from people trying to justify their mistakes:

•“I overspend because I’m just not good at planning.”

•“I ran up my credit card debt because I hate my job and I needed that vacation.”

•“I hid another purchase from my husband because I don’t want to stress him out.”

•“I can’t follow your advice on buying a home because I live in California. Real estate prices are just too high.”

•“With my schedule, I can’t drive for a delivery service in the evenings, so a part-time job just doesn’t work for me.”

•“I’m so stressed out that there’s no way I can cook dinner tonight. I don’t care that it’s not in my budget—I’m getting takeout on the way home.”

Listen, none of these excuses make mistakes go away. Nor do they excuse the bad behaviors. I’m not going to be mean to you if you’re making excuses, but saying “Oh, it’s okay! Mistakes happen!” over and over in these circumstances isn’t going to help you or your budget. Excusing bad behavior will stop you dead in your tracks from building wealth and living the life you want.

If any of this sounds familiar, there’s probably a reason why. If you’ve been giving yourself too much grace, I want you to hear me say that no one here is the exception to the rule. Not me and not you. If you want to win with money, you have to manage it wisely. The longer you enable your own bad behaviors, the bigger your financial mess will be and the longer it will take to clean up. So stop giving yourself a get-out-of-jail-free card. Even if you get a big financial break at some point, if you haven’t already learned wise money habits, you’ll blow through that big break only to keep repeating the past. So either way, it’s in your best interest to face your behavior head on. It’s time to face your mess, friend. You won’t be alone. We’ve got a huge community of people who will support you and cheer you along, and we have a ton of resources that will coach you—but you’ve got to do the work. No one else can do it for you.

Enabling Others

“He’s really trying.”

A sweet lady said this to me about her son. Her son lived with her, and she supported him financially. That situation in and of itself isn’t always bad. But then she went into more detail and red flags started flying. Her son wasn’t a 4-year-old kid; he was a 34-year-old man who dropped out of school a decade before. He’d been living with her ever since, unable to hold down a job. This grown man should have been living an independent financial life but was using his mother’s bank account as his personal ATM.

My heart broke as this woman shared her distress. She couldn’t see the real issue. She didn’t realize she was the problem. She’d extended way too much grace. She’d never allowed her son to experience full independence and be accountable for his own decisions, financial or otherwise. While physically he was a grown man, really, he was a little boy whose mom always cleaned up the mess he left behind. He’d never felt the pain of his choices or learned a better way.

As a mom, I totally understand the struggle this woman felt! The love you have for your child is unlike any other relationship in your life. They literally depend on you for their life! Especially us mama bears out there—we want to protect our children no matter their age. But think about it from a different perspective. Pediatrician and author Dr. Meg Meeker said:

We’re setting our kids up for failure when we teach them that what they really need is more of us and less of themselves. A great parent finds ways to allow children to fail so that they can teach that child one of the most important lessons in life: “You can fail, but Mom and Dad will never stop loving you. We’ll show you how to stand back up on your feet and try again.” If you really want to teach a child how to succeed, you have to teach them how to plow through failure.¹⁵

Meeker wrote this for a parent of a young child, but man, I think it applies to parents of grown children too. We all need to make mistakes and experience consequences so we can grow into resourceful, mature adults. When we enable another person, we short-circuit their learning curve and end up hurting them.

Enabling doesn’t stop with parents and kids either. It can happen between anyone, including extended family and friends. It’s really easy to see a need and want to help, but suddenly, you look up and realize you’ve been helping for far too long. My friend Lauren told me she’d had a friend, a single guy in her friend group, who was struggling financially. He lost his job and couldn’t pay his rent one month, so she covered it for him. The next month, the same thing happened again. She was genuinely happy to do it for him while he got back on his feet. Then, in month three of paying his rent, a mutual friend shared with her that this same guy had asked her for help too. The helping turned unhealthy because the struggling guy wasn’t learning how to help himself. He was blowing the extra cash on stuff he didn’t need. So be on the lookout for these types of situations. Extending grace when it comes to money mistakes is good, but extending it too far causes damage.

When it comes to where I fall on the grace scale, I’m definitely on this side. I usually assume everyone is trying their best, and I can be flexible and go with the twists and turns of life. I don’t get freaked out when rules are broken or people make mistakes. I assume they will learn from what happened and move on and not make that mistake again. As I’ve gotten older though, I tend to get impatient with people when the same mistake is made over and over again. So over the years, I’ve moved closer to the middle of the scale, but I still can give too much grace when something goes wrong.

Third-Party Enablers

There’s one other category of enabling we need to talk about before moving on: when someone you love is an enabler. This happens to a lot of people, and it can be really tricky to navigate. Maybe your parents are enabling your adult sibling. Or your sibling could be enabling their own child. It’s so dang hard to watch someone you love being taken advantage of. And a lot of times your loved one doesn’t even realize it’s happening.

I have a friend whose mom has been bailing out her son (my friend’s half brother) for years. Because her mom divorced her first husband when she was fairly young, she’d spent years feeling guilty about how it affected her son. So now my friend’s brother is in his midforties and keeps asking their mom—who doesn’t have a lot of money—for more and more help. It’s been going on for years, and my sweet friend is understandably upset at her brother. But what I wanted her to realize is that it’s not all her brother’s fault. The fault is also her mom’s. That can actually be a pretty tough realization to have. So what is she to do?

Offering advice on this topic is tricky because these situations are complex. So many factors come into play. There are times when it’s completely inappropriate for you to say anything at all. And there are other times when your guidance and direction as an outsider can bring truly helpful insight. But before you go speaking your mind, you need to be really clear on one thing: You cannot change other people. Let that sink in for a moment. As much as that might frustrate you, other people’s behavior is not your responsibility. You do not and should not have control over other people’s lives. That’s out of your hands. This may feel maddening at first, but it’s actually really freeing.

Once you’re really clear that you can’t change anyone, you realize all you can do is offer some feedback. If you’re absolutely determined to speak your mind with the lovable enabler in your life, remind yourself to create reasonable expectations for the outcome. The old saying is true: You can lead a horse to water, but you can’t make him drink. Just because you offer some truth doesn’t mean the situation will change. It might, but it might not. And if it doesn’t, take heart: It’s not your problem to solve. So let yourself off the hook. Double down on your own efforts to win with money and determine to be a good example. Pray for them. And if you’re holding on to anger or fear about the situation, focus on working through that and letting it go. If you don’t know how, seek the help of a professional counselor. It’s totally possible for you to win with money personally and live free of anger and fear over how other people are handling their money.

Whether you’re enabling yourself or someone else, you have the power to stop making excuses and take steps to find balance on the grace scale. Let’s look at those steps.

First Steps to Finding Balance

If you’ve extended too much grace to yourself or someone else when it comes to money mistakes, the first step is to recognize it’s an issue. This is probably the hardest step. When you’re neck-deep into enabling, it’s hard to recognize that your actions are the problem. You have to own this. If you don’t know if you’re enabling yourself or someone else, ask the trustworthy people around you. Someone has probably already told you the truth. If no one has said anything, ask a trusted friend who will tell you the truth. Now, don’t go asking your sister who’s still enabling her own daughter. Find someone with a solid track record of living wisely. Once you know you’re enabling someone, then you have to decide to do something different.

If you’re in an enabling situation, the second step is to set a boundary and stick to it. If you’ve been giving money to a family member for far too long or your adult child has moved back in with you and there’s no hope in sight that they’re moving out, you need to determine and communicate boundaries. Set limits on what you’re willing to do. Set a time limit on the duration of your help and what you expect in return. And be clear about what will happen if those expectations aren’t met. The conversation may be awkward and difficult, but it’s absolutely necessary—not just for your own sanity, but for the good of the other person. You want to give them the dignity of standing on their own two feet, and you can’t do that if you’re a constant safety net.

If you’ve been enabling yourself, write down the mistake you keep making and what triggers you to make that mistake. Then create a plan for what you’ll do differently when that trigger happens again. For example, if you’re triggered to shop online after a hard day, find a friend you can call to get coffee with instead. Then choose someone to hold you accountable to the new behavior.

We’ll walk through more specifics of healthy boundaries in chapter 9. For now I want to remind you that we’re talking about extreme cases here. If your son or daughter just graduated and needs to move back in for three months before their apartment lease begins, I’m all for it. You’ve got some natural boundaries in place in that scenario, and it’s not a chronic problem. Change will be necessary, though, when you’re enabling bad and ongoing financial behaviors.

When You Don’t Extend Enough Grace

On the opposite side of the grace scale are those who respond to money mistakes without enough grace. Again, for simplicity, I’m going to talk about this side of the scale using its extreme. In this case, the extreme of withholding grace is legalism. If enablers are the rule breakers, the legalists are the rule keepers. They love the rules. For them it’s all about right and wrong and black and white.

The other day a friend of mine ordered lunch at a drive-through restaurant for her big family. When she got home, she unpacked the order and realized they’d shorted her four side items. She combed through the receipt, and sure enough, she’d paid for every item she’d ordered, including those missing sides. My friend got so upset. She was mad at herself for not checking the order before she drove off and mad at the restaurant for making a mistake in the first place. Her family didn’t mind—they were happy with what she brought home—but my friend couldn’t eat. Instead, after she poured over the receipt, she called the restaurant to complain, then drove back to collect her eight-­dollar refund. She was anything but happy as she waited for the manager to fix the mistake.

The next day, as she thought through the incident, she had to shake her head at herself. She had totally overreacted and she knew it. Had a money mistake happened? Yes. Was it costly? Financially, not really—but she hurt herself by getting so upset about the situation. Would it have been better to offer grace in this circumstance? For sure. And experience tells me she might have gotten both her refund and a free meal out of it if she’d been more gracious.

When you tend toward withholding grace, you care deeply about integrity and doing things right. This is admirable and important, but legalists can take these things too far. They end up sacrificing people and relationships in their pursuit of being right. In the drive-through mishap, my friend was way too hard on herself and way too hard on the teenagers scrambling to put together her order during the dinner rush. Legalists can sometimes forget that efficiency isn’t our highest good—love is.

Now clearly, we need principles and rules. Without them our world would be anarchy. But being principled is not the same thing as being legalistic. You can have very strong principles without being legalistic. For example, I believe wholeheartedly in the Baby Steps. Winston and I live them every day. That’s being principled. Legalism is being unwilling to show compassion for a mistake or misunderstanding. It creeps in when there are rules without any love, discussion, or understanding.

If you lean toward the legalist side of the scale, it’s hard to extend grace because being right feels more important to you than being in relationship, even with yourself. A counselor I know once said, “You can be right, or you can be married.” It’s the same idea here. You can take principles so seriously that you can’t let yourself (or others) off the hook because you “know better.” Believing strongly in principles doesn’t make you a legalist. But favoring rightness over relationships, obedience over love, and rigidness over compassion does.

One of the heartbreaking things about refusing grace is that it causes people to be really, really hard on themselves. I have some dear friends who put themselves on this side of the scale, and they talk regularly about how brutally harsh their inner critic is. If they fail to live up to their impossibly high standards—which is going to happen—their world comes crashing down and their inner critic goes into hyperdrive. When they make a money mistake, they beat themselves up again and again, thinking, I am so stupid. Why did I do that?

That’s why it’s important that we stop and say this again: Nobody is perfect. Not even you. Money mistakes will happen. You will not get it right 100 percent of the time. It simply cannot be done. If you’re a legalist when it comes to money mistakes, this is so important for you to fully take in. You need to understand it both in your head and your heart. It will be a long, hard life if you keep replaying your mistakes.

We’re all going to fail—but that doesn’t mean we’re failures. Like we talked about in chapter 6, that’s a huge difference. Every one of us can say, “I failed.” But “I’m a failure” is a lie meant to stop us in our tracks. If you understand that mistakes will happen, that they don’t make you bad or a failure, you respond differently to them. You see them for what they are, and you get back up, dust yourself off, and try again.

Legalism toward Others

I remember a lady coming up to me after one of my events, and she looked so sad. She began to tell me how her husband had committed financial infidelity. He’d hidden purchases from her, and she’d just found out the night before. My heart began to break for this woman.

I began to imagine late payment notices and bankruptcy proceedings, and well, I kind of went to the worst-case scenario. When situations like this happen, the unsuspecting spouse feels deeply betrayed. Trust is broken. Communication breaks down even more. It’s such a hard situation! So I had a lot of compassion for her.

I asked a few follow-up questions to help me give her guidance, and she told me, “Yes, he went to Chick-fil-A three times last week and didn’t tell me.”

I looked at her like, You have got to be kidding me. Number one: It’s Jesus chicken. And number two: He probably forgot! His whopping total was probably $25, and she was talking like she was about to separate from the poor guy.

Those who have legalistic tendencies are as hard on others as they are on themselves, and they often have a hard time gaining perspective. If a rule is broken, it’s broken—whether it’s $25 or $25,000. Again, the intention is admirable. I have a lot of respect for this because integrity and doing the right thing are for sure important. If this is you, though, I need you to hear something: Living with you can be tough.

If you’ve ever been close to someone who’s legalistic, you have some idea of how exhausting it can be. You feel like you’ll never measure up, no matter how hard you work to earn their approval. It’s like the bar to keep them happy is always just a few inches out of reach. The crushing reality is that legalists can end up breaking the spirit of those they love the most.

Those who lean toward legalism tend to give love conditionally. For these people, love and affection are given only in return for good behavior if the other person is performing their duties properly. If someone doesn’t measure up to their impossible standards, they can disengage and remove their affection. This mentality is fundamentally flawed because literally no one is perfect. I once heard a young man in his early twenties say, “If someone hurts me, I cut them out of my life. No exceptions.” This guy had obviously been hurt deeply in the past, but if he follows through with that statement, he will be alone for the rest of his life. None of us can live up to his standard—not even him.

Another area where legalists can struggle is with judging others. They often make snap decisions without knowing the full story. A lot of enthusiastic Ramsey Solutions fans can probably relate to this. If you see someone driving a new car, you may automatically think, Oh, I bet they took out a loan for that car. What a shame. Or you see a friend posting beautiful pictures on social media from their European vacation and your next thought is, That’s extravagant. They probably put all of that on a credit card! But you don’t know the details of that person’s life. When I was a teenager and judging other people’s actions, my parents would tell me: “Rachel, you have a full-time job taking care of yourself. Quit worrying about what other people are doing.” The truth is, even if you’re right, even if someone used debt to make those purchases, it’s not your job to worry about it—because it’s none of your business!

Moving toward Grace

You may immediately know if you struggle with not extending enough grace for money mistakes. But if you’re not sure, ask someone you trust what they’ve seen in your life. Doing this can make you feel vulnerable—and you have to be okay getting honest feedback—but it will be incredibly helpful to learn how others perceive you.

Also, when you get that feedback, I encourage you to spend some time reflecting on what causes you to respond that way. As a person of faith, when I go to this extreme, those are the areas and the times when I’ve stopped trusting God. In those times, I’ve put too much pressure on myself to fix (or control) a situation. Reflecting on where you are on this scale can help you see the difference between what is yours to control and what is God’s to control.

Then, when money mistakes happen—especially minor ones—remind yourself it’s going to be okay. Living with a super black-and-white perspective is not good for anybody. It’s too limiting. It limits your relationships, and it limits the grace you give yourself and others. What’s critical is that you learn to move on and not let money mistakes define you or your relationships. Learning to relax a little will bring more lightheartedness and even happiness into your life.

If you lean toward legalism, practice giving grace even when you don’t think the person deserves it. There are lots of ways to do this. Choose a relationship in your life where you’ve been strict and back off, allowing room for mistakes. If you’re married, you’ll probably want to choose your spouse. Usually one spouse (ahem, nerds) is all about the budget and the money rules—period. But if your free spirit spouse makes a mistake here or there, instead of harping on it, just say the simple words, “It’s okay. There’s grace for that.” Then let go of any offense you feel. If the mistake keeps happening, have a conversation about it, but just offering forgiveness for the mistake is a great place to start.

Another way to practice extending grace is to ask yourself if what just happened is going to matter in five years. If my child takes a Sharpie to my brand-new chair, I may be sad or frustrated—but it’s just a chair. Your spouse overspending on groceries the first few months you’re learning to budget isn’t the end of the world. Forgetting to pay a bill on time isn’t ideal, but you won’t remember it happening in five years. Even bigger mistakes, like buying a car you can’t afford, can be overcome in less than five years. So practice extending grace and letting go of past mistakes. Living in a grace-filled, forgiving environment leads to a far more enjoyable life.

Now that we’ve explored what it looks like to respond to money mistakes with too much grace and not enough grace, I want us to talk about how to find a healthy balance between the two.