How to Break the Cycle of Feeling Like You're 'Bad With Money'

Each week on Money Confidential, Real Simple's new podcast, host Stefanie O'Connell Rodriguez has a real, honest conversation about money, all in pursuit of banishing some of the guilt and shame people so often associate with their finances. On this week's episode, O'Connell Rodriguez talks to Maria, a 39-year-old mother of two who feels a lot of self-blame for her current financial situation. (Maria is an alias, to protect our caller's identity.)

Maria is in what she calls a feast or famine cycle: Every time she gets paid or receives a check, that money goes toward unpaid bills—and then she's left waiting anxiously for the next paycheck. At the same time, she wants to be able to give her kids everything they want, and feels a lot of guilt when she can't afford it. Though Maria has tried to talk to her family members about her challenging situation, she still feels a lot of shame and believes she's not smart with money—and is struggling to find emotional support to help her get out of her bad money cycle.

To help Maria both get her finances under control and find some support—and eventually erase her money guilt—Rodriguez calls on Tiffany Aliche, a money expert known as The Budgetnista. Now the author of several books about handling your money—including Get Good With Money, out March 30, 2021—Aliche has had her own money shame spiral in the past. Since she got her finances under control, Aliche has been on a mission to help others do the same.

Listen to this week's Money Confidential—"I'm tired of being 'bad with money.' Where do I even start to get my finances on track?"—to hear Aliche and Rodriguez's tips for fighting money shame, getting your paycheck-to-paycheck finances under control, and finding the emotional support you need to move forward on your money journey.

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Maria: As soon as I got credit cards, it kind of brought out my wild side, like, 'Ooh, I can spend money now.'

Laura: And so it's really hard to find a way to pay everything at the same time and still not feel like you're in so much debt.

Maria: I do feel like it's my fault and that I'm not good with money. I'm not smart with money.

Laura: 'So my question is, how do I even start?'

Stefanie O'Connell Rodriguez: This is Money Confidential, a new podcast from Real Simple about our money stories, struggles and secrets. I'm your host, Stefanie O'Connell Rodriguez, and today we're talking to a listener we're calling Maria.

Maria: I have been stuck in a cycle of feast or famine, so I'll get a really big check, but because I've been behind on my bills, I have to use all that money to pay my bills. And then I'm left with nothing. So then I'm kind of waiting. I'm stuck. Everything is stagnant. I have no money and then I'll get another big check and I'll have to use it to pay all the bills that I hadn't been paying off previously. And it just keeps happening and happening. Like I can't catch up.

Stefanie O'Connell Rodriguez: 74% of Americans are living paycheck to paycheck. But when it's just you and your bills, or you and your bank account, or you and your credit card statements, it can feel really isolating.

Like how does everyone around you seem to be making things work—staying on top of bills and even saving up for big purchases like a house or a vacation—while you feel like you're just struggling to make ends meet?

I've been talking to people about their money for the past decade, and one of the biggest things I've found, is that most of us struggle with money at some point in our lives.

But it's hard to talk about those struggles and admit the money mistakes we may have made. So we're breaking down those barriers here at Money Confidential. This is a place to get real about money, to share your money questions, struggles, and even secrets. And we'll bring in additional financial experts to offer some real, practical solutions.

Because while money is complicated and talking about it can be hard, it is not a struggle you're alone in experiencing. Which brings us back to today's listener Maria, which, for the sake of confidentiality, is not her real name.

Maria: So I live in the suburbs outside of Chicago. I am 39 years old. And my relationship with money has been rocky.

Stefanie O'Connell Rodriguez: To get some more insight into Maria's relationship with money, and how the cycle of feast or famine she's struggling with started, I asked her to take me back in time to her first memories of managing her own money.

Maria: In college, I remember walking down the breezeway at the university and some people came up to me and offered me a credit card application.

So I was like, yes, let's do this, because I remember my mom had like 20 credit cards in her wallet at all times. That's almost when things started to go south, because I started to get a credit card and then I would use it and only make the minimum payments on it sometimes. And I got a second credit card because they offered me one as well.

By the time I was married and getting ready to set up life insurance policies and stuff, I know I was already $10,000 in debt and it was embarrassing to me. My husband didn't even know how much I had on my credit cards at the time. So I felt ashamed of kind of hiding my own money patterns.

I didn't feel like a good person. I felt like I had been hiding something and I felt like I was wrong.

Stefanie O'Connell Rodriguez: But it seems like you were personalizing it. Like something was wrong with you as a person, as opposed to just the fact that you were in a situation of credit card debt, which is quite common.

Maria: Yeah. I do feel like it's personal. I feel like it's my fault and that I'm not good with money. I'm not smart with money. I'm not responsible with money. So that feels like it's a reflection of me as a person.

Stefanie O'Connell Rodriguez: Because of that feeling, are there parts of managing your money you avoid like opening bills or checking bank account statements or anything else?

Maria: I definitely avoid opening bills until I know I have the money to pay them. I have not even been looking at my calendar in terms of when I'm supposed to pay each bill, because I know I can't, and I hate getting alerts on my bank app on my phone, because I just know it's going to say you're overdrawn.

I just got to a point where the debt was so high and the influx of cash and the actual dollar amount in the bank felt so low that it got to be depressing, looking at that over and over every day.

Stefanie O'Connell Rodriguez: How long have you felt this way?

Maria: I would say definitely within the past six months, but it's been somewhat present in my life since I was divorced about five years ago.I think last year around the holidays, I just went way over budget and that's what kind of tipped the credit card debt to a place where I couldn't keep up with it anymore.

Stefanie O'Connell Rodriguez: Is there a joy in those moments to the spending of the money?

Maria: I feel good when I can provide for my children. I spend more around the holidays because I'm a generous person and I want everybody to be so happy and to get what they want. And so this Christmas, for example, I bought my son a PC, whereas I could have saved that money and used it to pay bills. What really lights me up is when I'm able to provide for my kids without always having to say no.

[Stefanie O'Connell Rodriguez:How does saying no to them feel?

Maria: It feels difficult because I always get a little bit of pushback and they've even said some things to me. Like, mom, you never have any money.

So when my kids ask me that, why don't you ever have any money? I feel guilty. And I feel like I'm not doing a good job. So the being a bad mom with money sort of ties in to just mom guilt in general.

Stefanie O'Connell Rodriguez: Beyond that conversation of them saying you never have any money, Mom. Like, have you had any conversations about money with them?

Maria: Yes, they have been asking me questions like, well, so what does it mean to be overdrawn and what are you using the money for? how much money do you have? What kind of bills do you pay? How much is the mortgage? They've been definitely getting more interested in money, which I think is good. It's just I wish I was setting a good example.

Stefanie O'Connell Rodriguez: Do you feel like when you tell them the answers to those questions that it registers for them, that they understand what it means?

Maria: I do, especially when explaining what it means to be overdrawn and how even if I get this money, I basically have to pay the bank back first. And so then I'm left with no money and they kind of think it stinks, but they understand it.

Stefanie O'Connell Rodriguez: Have you talked to anyone about these financial challenges with your family, uh, with your partner, anyone?

Maria: My partner knows what's going on. He's trying to help me as much as he can. And in addition, I did tell my family a couple of weekends ago because it just all sort of came out. It was a bad night. I was upset about a lot of things. And so they know I'm in a difficult position, but they're not really in a position to help me either or they don't want to.

Stefanie O'Connell Rodriguez: Have they been helpful emotionally?

Maria: No, that discussion that we had came up and then it was just like it never even happened. We haven't spoken of it since.

Stefanie O'Connell Rodriguez: Since you don't feel supported by your family, have you sought out other sources of support?

Maria: I have very recently joined a few financially focused Facebook groups, so I'm trying to get more involved in those so that I can learn from them as well as share my small wins. Joining these groups virtually feels very safe, almost because they can't see me face to face per se. And so there is sort of a certain amount of anonymity to it that makes me feel comfortable.

Stefanie O'Connell Rodriguez: How do you imagine your life would change if you felt more control over your money?

Maria: I would feel better. I would feel like I sleep better at night. I'm not suppressing the worry and anxiety that I have about it, which is basically what I'm doing now. And I would feel free.

Stefanie O'Connell Rodriguez: And what would you do with that freedom?

Maria: I would infuse it back into what I love, which is my business and my kids, my family. I'm a very generous person when I can be. And that's just been stifled in this time of feast or famine.

Stefanie O'Connell Rodriguez: Do you feel like there are other parts of you that have been stifled because of this?

Maria: I think so. I think definitely my creativity, because again, that feels like it's tied to freedom. And so if I don't feel free, I also don't feel like I'm very creative and it's just a sense of maybe low self-esteem, low self-confidence that probably pervades all areas of my life.

Stefanie O'Connell Rodriguez: I think you're kind of identifying things that you value about yourself, that you're feeling like you have to suppress because money is a roadblock.

Maria: Definitely.

Stefanie O'Connell Rodriguez: Talking to Maria was a reminder of how money is about so much more than numbers on a page. It's about the promise of what that money might afford you—the peace of mind to sleep better at night, the freedom to be creative, the ability to be generous and the confidence to live in alignment with your values and potential.

Our conversation was also a reminder of how painful it can be when money becomes a constant, seemingly impenetrable roadblock to achieving those things. And how, in the absence of a network of social support for managing the real challenges of things like credit card debt or not having enough cash to cover all the bills, we start to internalize our financial circumstances, and see them as a reflection of who we are as people, rather than the just situation we happen to be in.

' I'm not good with money. I'm not smart with money. I'm not responsible with money.'

These are things I've heard over and over again, not just in my conversation with Maria, but with people across all levels of income, across all levels of education, and across all levels of success.

When we come back we will be joined by an expert who has literally written the book on getting good with money.

Tiffany Aliche: Hey, Hey, Hey. My name is Tiffany Aliche, better known as the "Budgetnista." I am a financial educator and author and at the end of the day, I'm a teacher.

Stefanie O'Connell Rodriguez: Tiffany's new book is called Get Good With Money: 10 Simple Tips to Becoming Financially Whole. So I asked her about Maria's situation—how much Maria had internalized this idea that she was somehow bad with money and how Maria might change that.

Tiffany Aliche: So Stefanie, what it sounds like that Maria is experiencing that I have been through. And so many of us have been through is that she's feeling financial shame. But the thing about shame, it's really destructive because shame is a liar. Shame doesn't say that there's a mistake that's being made. Shame says you are a mistake. You feel bad about you, versus focusing on maybe an action that you have control over that you could do something different.

You know, not, 'Oh man, you know, I used my credit card.' It's 'Oh man, I'm so bad. Why did I do this? I'm really dumb. I'm always doing this.' That's what shame does.

Meaning that in order to shake that shame, Maria is going to have to share with someone that she trusts, whether it's a financial advisor, financial planner, her bestie, whomever, she's going to have to give voice to the thing that she's ashamed about because in that safe environment, they are going to reassure her.

I remember the first time I told someone like what I thought was my biggest darkest financial fear was. It was my best friend, Linda. It was after the great recession. It was like 2010. And I was ashamed to say I had lost my job. I was a teacher for 10 years. I was ashamed to say I didn't have an income and that I couldn't afford my mortgage.

I couldn't afford my bills. So I told no one and shame thrives on aloneness. Right? Shame thrives on you keeping quiet, shame thrives on you not telling anyone anything. And so I was keeping all that stuff to myself for like a year. And I honestly stopped hanging out with my friends until one day, my best friend, Linda, after kind of like harassing me via phone calls was like, 'Tiffany, what is going on?' I broke down and started crying and I told her, I lost my job. She's like, like everybody else? It was like, what? It was like, I can't afford my bills. She's like, again, like everybody else? I was like, wait, what?

And what Linda effectively did is that she debunked what I had told myself I'm bad because I've made these mistakes. Instead she allowed me to see that there are some mistakes that I made, but it wasn't a condemnation of my character.

It was instead, these are mistakes that you made, other people have made those mistakes, too. And so that's what I'm wanting from Maria to give voice to her shame so she can shake it off.

So once I was like, okay, I'm not going to beat myself up anymore because I am one of many other people who are also struggling. So let's now actually look at what is it that I'm struggling with, and let me just write down my full situation. This is who I owe. This is how much I owe, this is the status. I'm late, I'm on time or whatever. So I literally just wrote down my financial situation on a piece of paper, so I could start to see what did I need to prioritize and put my energy toward to start working my way out of the hole that I found myself in.

Now this part is definitely, is really important. Cause I didn't do this and I wished that I had, that I did too much. It's like, you know, everyone in the beginning of the year: I'm going to work out every day, I'm going to run three miles. And if you have never run before, and all of a sudden you go to pushing yourself to run three miles after a while, you know, maybe a week, maybe you'll make it maybe two, but it's too much.

It's okay to ask yourself for less until you get warmed up. And so that's the next step is to ask yourself. Okay. Well, what can I do in the next 24, 48, 72 hours? Instead of saying, I'm going to pay everyone, I'm going to drain my bank account. I'm going to withdraw all my money from my 401k and get this right.

No, you know what? I'm going to call the debt collectors that I've been kind of avoiding and ask to see if there...a hardship program. Hmm, you know, so super simple, like, you know, asking yourself for less. It's just going line by line by line and being okay that not everyone is going to get paid at the same time.

That was hard for me to understand too, because I certainly would, everybody has to get paid now, even if it means I'm homeless and hungry and cold. It's like, no, no, no, no. They haven't gotten paid all this time. It's okay to say, well, hey, cell phone company, or hey, credit card company, I'm going to need a minute because this rent really has to get paid, so I have someplace to stay.

Stefanie O'Connell Rodriguez: How do you know what expenses to tackle first?

Tiffany Aliche: So first and foremost, I wish somebody would have told me that you want to look at your health and safety expenses first. So these are the expenses that you need to maintain your health and maintain your safety. So your rent and your mortgage might be a health and safety bill, you know? I have childhood asthma, so it's like, okay. You know, sometimes I need my inhaler. So that's a health and safety bill. Food. That's a health and safety expense you know, they say on the plane ride that you put your mask on first because if you put your baby's mask on first and they're fussy and then you lose consciousness. So now you are not protected, but neither is your child because you're not there.

So bill collectors can't get paid if you are not in a good spot. So take care of your health and safety expenses first, and then you can get to them.

Stefanie O'Connell Rodriguez: This is a theme that I think is really also valuable when we're talking about being a mother too. The thing that Maria identified as kind of tipping her credit card debt to the point where she felt she couldn't keep up with it anymore was the holidays.

It's emotional. It's like a way for me to say, I love you. It's a way for me to provide it's a way for me to be a good mom, especially during the pandemic where there are so, so few ways for kids to get the things they want and need.

And so I'm wondering how that how that personal work compounds with the guilt, the mom guilt and that need to provide. And, you know, I think for parents, it's just—we might know, in theory, we need to take care of ourselves first. How do we make that happen?

Tiffany Aliche: So I'm a step mom but this is what I remember distinctly when my mom lost her job right before Christmas, she was a nurse and you know, I'm one of five girls, so we have a big family. Five kids, Christmas is coming. No job for mom. What do we do? But one thing that my parents did that still struck me to this day is they sat down and they told us in a way that was matter of fact, not scary.

I had to have been, I want to say maybe like 13 or something like that. And it was like, hey guys, you know mom lost her job. And we were like, yeah. I said like, but the good thing is, you know, she's going on interviews. She should have a new job soon. And we were like, okay. And she was—my dad was like, but you know, Christmas is coming.

And I remember feeling dread like, 'Oh no.' And he said, but the good thing is, we're pretty sure that mom will find a new job in January or February because by then it was November. So we're going to keep our tree up until then, and put presents underneath when she gets her new job. And we were like, okay! You know, so for us, it wasn't, you're not getting presents.

You're not getting this. You're not getting that. It was, this is what's happening, but this is what we're going to do about it. So transparency in a way that's age appropriate for kids, I think is a way to help navigate.

Here's the thing. If you have like a little one and they slip and they fall and they look at you like, should I cry? Is this bad? They are looking to you to see how should I react based upon your reaction to what's happening.

So if you freak out with your finances, they're like, oh, this is a freak out moment. So my dad, I was at 13, I was trying to gauge, is this bad? Is this good? And it was like, oh, no biggie, because look at that, he seems calm. Meanwhile, inside he might have been like, ah! But he seems super calm. So I was like, well, I'm calm.

I guess we'll have Christmas in February. And we did.

Stefanie O'Connell Rodriguez: I think for a lot of parents, the idea of transparency around money when money is tight, just means saying no, and that's not something they want to do. But what you're showing in your story is transparency around money can look like a lot of different things.

It can be reframing the no's into these lessons. And I think this is another thing Maria shared is like, she's had a little bit of this conversation with her kids, but I think what's being reflected back to her in her kids' questions about money are the insecurities she has for herself.

And you know, this, this idea of I'm bad at money while her kids are saying, mom, why don't you have any money? And I think she's kind of internalizing that as a judgment of herself, rather than maybe a reflection of the conversations that she's been having.

Is there a way you recommend approaching that conversation with other people so that it doesn't kind of reflect back that shame and judgment?

Tiffany Aliche: So finding your Linda, just someone that you can share, honestly, what you're struggling with in your finances in a way that you're not looking for them to provide solutions, just the listening ear, because you want someone to help normalize what's happening because once you realize that you are not alone in a thing, then you can stop the, well, it must be something that specifically I'm doing because of who I am.

The fact is that if you don't get past the emotional component, you will find yourself back there repeating the same mistakes and then passing on that same lesson and energy to your children. And so you want to unlearn some of those things to teach yourself like, okay. You know, one, it's not just me. Two, it's not about my character. And three, there is a way out.

Stefanie O'Connell Rodriguez: Tiffany created a Facebook group she calls Dreamcatchers to provide a safe space for women to ask and answer financial questions, encourage and support one another and hold each other accountable for their dreams and money goals.

Tiffany Aliche: I can remember there was a woman similar to Maria. It was like two years ago. She said, I don't know what I'm going to do.

I've got two children. Christmas is coming. I'm struggling. I want to buy them presents. I know I shouldn't, but it's like the only thing that I feel like can make their lives feel a little bit normal. I feel ashamed that I don't have it.

And before I could say anything, a woman, two kids, who had struggled last year was like, hey girl, this is what I did. Another woman hey, girl. This is what I did. And I thought to myself, well, that's what I love about finding these groups is because to have another mom with similar-aged kids, similar situation and background, saying, that was me, this is how I solved that problem, was so potent.

Stefanie O'Connell Rodriguez: While the anxiety and stuckness Maria is feeling around her money is connected to so many of these things, there's also just the reality of having more month left than money, which led my conversation with Tiffany to the b- word.

Tiffany Aliche: It starts with a budget and a simple, simple budget is just money in, money out. And ideally money in, in a month's time, money out in a months time, just listing everything you spend money on, how much do those things cost you a month on average? How much are you making in a month?

And then if the numbers are not what you're wanting them to be, okay, well, what's on my money out list, what are some things I can change? Is there enough money coming in on my money in list, what are some things I can change? So at its bare bone basics, you start with a budget.

Stefanie O'Connell Rodriguez: I think budgeting gets a bad rap and it kind of comes back to this emotional side of it. Like, it feels like it's restrictive. It feels like it's telling me what I can't do. And so how does somebody maintain that momentum when they feel like, again, it's like, all I hear is 'no', when I think budget.

Tiffany Aliche: Honestly, Stefanie, I look at my budget as my say yes plan. Can I go on vacation? Yes. When you saved this amount of money. Budget, can I buy this car? Yes, if you make, you know, ask your boss for that raise. And so switching how you think about a budget that your budget truly is there to make those things that you want happen, but to do so in a way that's not going to harm the rest of your financial life.

Stefanie O'Connell Rodriguez: And how does that stay top of mind when you are actually going about your day, how do you stay accountable to that budget that you maybe set at the beginning of the month, but then, you know, it's easy to get lost along the way.

Tiffany Aliche: Well, I believe that automation is the new discipline. Automation doesn't get an attitude. Doesn't get hungry. Sassy. Automation's not tired. So I set my automation up beforehand. So my husband is like, he used to call me the Budgetnista bully. I was like okay, how could I be nicer about it? I realized that I'm the spreadsheet girl. I love it. You know, but he's totally not. So I said, okay, let's see if we could do budget without budgeting. So I told him, go to HR, go to your, um, you know, whoever does your payroll and how many times can you split your paycheck?

He's fortunate that he could split it up to four times. So now he doesn't get all his money in one account, like before, they put some in our joint long-term savings account. And they put some in his personal savings, they put some in our joint checking account for bills and they put some in his personal spending.

So now when money comes in, I'm not like, did you transfer money to the bills account? Did you transfer money to the savings account? He split it before he get it. So you can literally create a just bare bones, simple budget by...if your job allows to have your money come in and split it before you get it.

Or you could do it yourself, have it land in one account and have that account make the transfers for you after it lands. But that is a way to keep on top of things and automating that system is just really going to help. Like I automate everything so those bills get paid. I don't have to worry about it. My job is just to make sure every month, is there enough money? I know how much our bills are. I'm like, is there enough money in that account for the bills? Yes, there is. My savings is saved automatically. So automation is a new discipline.

If you set up the automation that you could check on it about once a month, just to make sure that it's running smoothly, but you don't have to have like all the discipline and doing all the tweaking yourself.

Stefanie O'Connell Rodriguez: Well, and it feels like that system also helps just generate a little bit more momentum too. And I think what you're talking about here is just seeing all of those additional opportunities for getting wins.

Tiffany Aliche: Yes, exactly.

SStefanie O'Connell Rodriguez: And why is this acknowledgement of what's working important?

Tiffany Aliche: It's super important because if you don't acknowledge the wins, it just always feels like you're either working toward digging your way out of a hole or running from. There are going to be financial responsibilities forever. And so if it's always coming from a place of fear, from a place of lack, from a place of just like, you know, just this, this, this dark cloud over you, then it's going to be like that for a very long time.

And so even me, sometimes I can certainly feel overwhelmed, especially when I was digging my way out, but it was like, like I remember I was, for example, someone said to me, 'Tiffany, you know, my car broke down and I just finished saving, you know, $400. I was so proud of myself and it cost $400 to pay off, you know, like to fix my car.'

And I was like, sounds like a win to me. And she's like, why? I'm like you just said, for the first time you saved $400 in your emergency fund, and then you had an emergency and you had the funds.

That's a, that's a win because what would you have done before then? She's like, 'use my credit card.' So, you know, so it's, it's, it's the same thing, but looking at it differently, like, what are you leaning in toward versus running away from?

Stefanie O'Connell Rodriguez: So what do you when, like Maria, you're tired of being bad with money?

Well, you can start by taking stock. Where is your money actually going—where does it need to go and where do you want it to go?

Go through bills and expenses line by line, prioritizing your own health and safety needs first.

Reframe your spending, not around what you're trying to get out of, but what you're trying to move toward. A plan that isn't built around 'saying no' but serves as a guide for saying 'yes' to more of what you want.

Automate where you can—automatic bill pay, automatic savings, automatic debt payments. Take advantage of these systems that set you up for long-term financial success while letting you spend more freely with whatever's leftover.

Look for communities where money isn't taboo, where you can safely share your money mistakes, fears, and questions, and let go of the shame that comes from isolation.

And finally, celebrate your financial successes and work on building upon those instead of focusing exclusively on what's not working in your financial life.

Being 'bad with money' is not an identity. And money mistakes are not a reflection of who you are. They don't dictate your value, nor do they dictate your potential. Money mistakes are simply moments in time. And every moment offers a new opportunity for 'getting better.'

This has been Money Confidential from Real Simple. If you know how Maria feels and want to share your experience send me an email at money dot confidential at real simple dot com. You can also leave us a voicemail at ‪(929) 352-4106‬.

Money Confidential is produced by Mickey O'Connor, Heather Morgan Shott, me, Stefanie O'Connell Rodriguez. Thanks to our production team at Pod People: Rachael King, Matt Sav, Danielle Roth, Chris Browning and Trae Budde.

If you like what you hear, please consider leaving us a review on Apple Podcasts, or telling your friends about Money Confidential. Real Simple is based in New York City. You can find us online at realsimple.com, and subscribe to our print publication by searching for Real Simple at www.magazine.store.

Thank you for joining us and we'll see you next week.