How to Start a Money Date Practice That Creates Possibility Instead of Overwhelm

Money Files

There is a moment most people know well, the one where you have a general sense that something is off with your money but you do not want to look closely enough to find out what it actually is. You tell yourself you probably overspent, you are not sure by how much, and because you do not know the number you cannot do anything about it. So you wait, and the week passes, and the record keeps skipping.

That is what financial avoidance actually looks like, and it is not a discipline problem or a math problem. It is a possibility problem. When you do not have the truth about your numbers you are working with a story, and the story is usually some version of you are not good with money and nothing is going to change. A money date breaks that cycle not because it magically fixes your finances but because it connects you to the truth, and the truth is something you can actually work with.

In this episode I want to talk about what a money date actually creates inside your mind and your body, not just what you do on one. Because the real gift of looking at your numbers every week is not the information itself, it is the direction that information gives you. Right now without a money date you have avoidance, overwhelm, and no next step. After one you have a number, a pattern, and something you can actually decide to do about it.

In this episode you’ll learn…

[00:04:20] Why resistance to money dates almost always comes from the belief that looking at the numbers is not going to make any difference, and what actually happens in your mind when you finally connect with the truth about your spending

[00:08:45] How a money date creates possibility even when what you find out is not good news, and why knowing you overspent by $200 is always more useful than not knowing at all

[00:13:15] What Keina does with her own clients on a weekly money date, including a real example of a client who found a $21 charge coming out of her account that she did not recognize and what that kind of regular attention to your numbers actually builds over time

[00:18:30] Why tracking expenses is not the same thing as budgeting, and how the practice of comparing what you said would happen to what actually happened is where real financial awareness gets built

[00:22:45] The four step money date you can start this week regardless of whether you have a perfect budget or any budget at all, including how to predict your own unplanned spending once you start noticing your own patterns

[00:27:10] Why putting a money date on your calendar for the next four weeks straight is going to teach you more about how you actually manage money than anything else you could do with your finances right now


Tune in to this episode of Money Files to learn what a money date actually creates for you and how starting a four week money date practice can break the cycle of financial avoidance and give you the direction and possibility you have been missing.



Are you ready to start asking for help with your finances? Apply to work with me, and let’s start working towards your financial goals.



If you loved this episode on money dates and breaking the cycle of financial avoidance, check out Episode 216: Why Your Budget Keeps Breaking (And How To Fix It) 


Transcript for “How to Start a Money Date Practice That Creates Possibility Instead of Overwhelm

Intro: Hi, and welcome to Money Files. I’m Keina Newell from Wealth Over Now. I work everyday with professional women and solopreneurs to help them get out of financial overwhelm and shame so they can experience more flexibility and ease with their finances. Are you ready to gain confidence and learn to manage your finances intentionally? Tune in and grab financial tips that will help you master the way you think about and manage your finances. 

Keina: Hello, and welcome back to another episode of Money Files. So one of the things that you may or may not know about me is I walk a lot. And I had actually started recording this episode outside, but my AirPods are far too good. And there were cars, there were birds. I live in Washington, D.C. So there was like all the cars honking. There probably was some ambulances as well, like emergency vehicles. So I hope this still captures my raw thoughts. But on my walk, I was just thinking about money dates. And if you’ve been following me for a while, or maybe you’re new here, you may or may not have heard me talk about money dates. And I want to touch on money dates, but I don’t really want to touch on what do you need to do on a money date. I want to more so talk about what a money date actually creates inside your body and in your mind. 

One of the best gifts that I have given myself is coaching. And I’ve participated in life coaching, business coaching, a blend of the two. But I feel like when I was in education, I’m a very logical and linear person. So I never really thought about what’s happening in my body? What’s happening in my mind? What am I thinking? How am I feeling? But those things are so important for us to stop and pause because our mind and our bodies, they let us in on how we’re actually feeling. And if you’ve never actually had someone illuminate what happens in your body or what happens in your mind, then you don’t know how your body and your mind are controlling what you are willing to do and what you’re not willing to do. 

So when I think about a lot of my clients, I feel like they have resistance to doing money dates. And I think that the resistance comes from a belief that it’s not going to make any difference and that they don’t really know what they’re looking for. And they just feel frozen and they feel overwhelmed. It feels like no matter what they do, the numbers aren’t going to get better. And when I think about myself, when I have fallen off of doing my money dates, because just newsflash here, I am not perfect by any means. There are weeks that I’m not looking at my money. There’s even been months where I haven’t looked at my money. And it’s more rare that, that happens but when it does happen, I have been able to observe what I’m thinking about and how I’m feeling about my money. And what I can see myself like not wanting to look at the numbers because like, oh, I don’t want to see how much I’ve actually overspent and I don’t want to know what promises I’ve actually broken to myself if I’ve had financial goals. I told myself that I would do this and not that. 

So this morning I was just thinking about, with money dates specifically, what does a money date do besides just tell you where your money is going? And I really believe a money date gives you a sense of possibility. Even if what you find out is like, dang, I really did spend $1,000 on my credit card or I overspent because I was outside living my life and I was feeling really rich. Whatever that looks like for you, the reason a money date creates possibility is because you get to be connected to the truth. And the truth is something that you can actually work with. I’m going to say that again. The power of having the money date is because you connect with possibility. And when you’re connected to this possibility, it creates truth. 

Right now you don’t have any truth. You’re going off of, I think I’ve overspent. Oh my goodness, I don’t know what the numbers look like. I can’t do anything. You basically have this record on repeat and you haven’t stopped it. In my head right now, I have an image of a record player and think about it like skipping. And if you don’t actually go in, I don’t know too much about record players. But I do know that it’s like people had to move the needle in order for it to get off of that space where it was repeating. So when I think about a money date and what it creates for you, it creates possibility because you get to be connected to the truth and you’re no longer telling yourself this broken narrative. 

Maybe you did actually overspend, but now I actually know how much I overspent by. Or maybe I was a little bit too happy and I thought I had a lot more money than I did. But now that I know I can decide what I want to do with this truth. So your money date is going to provide you possibility. And that truth is something that you can work with. Because right now, when you don’t have the truth, like I just said, you’re working with this broken record that you’re not good with money. Here you go again, you’ve messed up. You’re never going to be good with money. And when you’re thinking that way, it is defeating. But when you actually look at your numbers, you can gain this sense of possibility. And most importantly, you get to gain direction.

Maybe you find out that it isn’t as bad as it seemed. Or maybe you find out you did overspend, but it’s by $200. But now that gives you direction. Maybe this money date tells you how much overtime you actually want to pick up. Or maybe it gives you insight on what you actually want to do with your next check. Your money date is going to give you a next step. Right now, without the money date, you don’t have a next step. You just have avoidance, you have overwhelm, and you are frozen. You are like a block of ice. And one day you may or may not melt. And I don’t want you to stay in that position. That can just feel paralyzing. And I want you to have some mobility. I don’t want you to be paralyzed. 

So no matter what your goal is, maybe you’re focused on saving money. Maybe you want to pay down debt. Maybe you just want to be able to put all your bills on auto pay. That would feel really good to do by the end of the year. I want to tell you that it starts with a money date. And when I talk about money dates, I think that there can be different variations of a money date. And when I say variations, like the beginner level money date versus like I’m married with kids money date. I don’t want you to not do a money date because you think that you have to do it in a certain way. You can have a money date, regardless of whether or not you have a perfect budget. So if you’re sitting there thinking like, Keina, I just found your podcast. I don’t even have a budget that works. 

I would simply say, okay, your money date, it sounds like you’re going to look at your bank account. You want to look at how your money actually moved this week or where did it go? What was planned? What wasn’t planned? If you have a more detailed budget, you have a more detailed system, maybe you’re one of my clients and you’re listening to this, then you’re going to have a money date, like the money date that I’ve taught you to have that is going to be beneficial for you. But no matter where you are on this spectrum, I want you to start and just open the door of possibility for what can happen when you actually have truth behind your numbers. So the questions that I ask you are good questions to ask yourself every week. So what’s actually going on in my bank account? How did money actually move this week? Where did it go? Was it planned? Was it not planned? 

Those are really good questions to start with, even if you don’t have that perfect spreadsheet, because you are going to notice patterns. And you know your girl loves some patterns. Because when you start to notice patterns, then those patterns are going to help tell you the truth. I actually, as a part of my five month coaching partnership, we go through, I don’t know if you realize this or not, but I literally, my clients, they share their bank account screen with me. I walk them through a money date. And one of my clients, it had been a week since we met. So we have a cadence of basically meeting every week. So it had been a week since we met.

The last week we had talked about the bills that she felt like were going to come out. And we’re pretty new in setting up her budget. So I’m listening to her. I’m gathering information. So she told me about the bills. I invited her to think about, okay, what else are you going to be doing this weekend? She has kids. So what are you doing with the kids? Are you going out to eat? Do you need to go grocery shopping? Some of the things that you don’t actually think of as bills. So then this past week, after talking through her expenses and then looking at her account almost a week later, we were looking for what actually, so there was the money in your account. There’s the things that you said would happen. Now let’s look at what actually happened. And that’s what so many people miss when they are tracking their expenses. We don’t want to track.

We want to budget. We want to decide what did we say versus what happened. And we want to do that with regularity. But it was interesting because I knew the things that she said were going to happen. And then I was looking at her expenses to see what actually happened. But what we found was like, oh, we forgot a bill. Oh, I actually, I was really surprised at how much I ate out, even though I didn’t really have intentions of eating out. And she had awareness about us talking about that. She even noticed something that came out of her account. She was like, Keina, I don’t even know what that $21 is. She’s like, but I called about it and they’re refunding it to me. 

But like, if we didn’t have this set up system to look at her numbers, like that $21 expense, who knows how long that’s been coming out of her account. And maybe it’s not that $21 expense, but it’s another $21 expense, but it can be something. So then this week we’ll meet again in another week. But like, we looked at her expenses. We talked about, okay, this is how we expect money to move. Like, what’s the plan for that? And then in a week from now, we’ll see what was unplanned. So this is what I’m doing with my clients. It’s on a little bit more of a detailed level because I’m there helping them make decisions about things that are popping up and they feel like they need to plan for and they make sure everything fits. 

But the point is that if we’re not looking at the numbers, we’re not creating possibility. If we’re not looking at the numbers, we can’t identify the patterns. And you might be someone, like I said, who’s telling yourself, oh, I don’t spend that much on eating out. And then when you look at your bank account, week after week, and you’re actually looking at what was planned versus what was unplanned, you might find that you’re right, or you might find that you spend more than you actually think you do. Or you might find out that you are spending $50 a week on lunch. And you’re like, oh wow, I wasn’t even thinking about that as eating out because when I think about eating out, I’m thinking of like a sit down restaurant, but I’m grabbing Chipotle here. I’m grabbing another Chipotle or something there. 

And so I’m spending $200 a month on like lunches, but I haven’t actually factored that into how I spend my money. So then you get to have a conversation with yourself about like, do I actually want to continue spending money in this way? Is this something that I like or that I don’t like? Or do I want to tell myself to bring my lunch to work. But you get to be in control of those decisions because you can see what’s actually going on. But you don’t get to be in control of that decision or have that conversation with yourself if you’re not actually having the money dates because what you don’t actually measure, you can’t change. And what you avoid, you can’t change.

So just to recap, here’s how I walk you through a money date. So first thing, look at what your money did. Was it planned or unplanned? Just see where you are. Number two, ask yourself, what didn’t work? What didn’t work for me this week about my spending? Maybe something on your car broke or maybe something in the house came up and you weren’t prepared. Maybe there was a bill that you didn’t realize was coming out. So just categorize that. Number three, decide what you want to change. And this is completely up to you, not anyone else. From everything that was planned, unplanned, or just how you moved throughout the week, is there anything that you would want to change about your spending? 

And number four, think ahead. What is coming up this week? Where might there be unplanned spending? You can actually try to predict your own unplanned spending because you’ll notice your own patterns. You’ll be like, oh, dang, usually on Thursday nights, I get kind of tired and I don’t want to cook. So you might order out. That could be unplanned. What’s your planned spending? What are the things that you absolutely know are going to happen? And then I want you to also think about what’s coming up in the next 30, 40 days that might not be on your radar because it’s not a regular bill. So look at your calendar, think about what time of year it is, and then also capture what’s on autopay and has it actually come out of your account yet? That’s a tricky one because sometimes people have things on autopay and they think it’s automatically covered because it’s on autopay. And girl, just because it’s on autopay doesn’t mean it’s automatically covered. So make sure you’re paying attention to that. 

But by sitting down and getting curious with your money, you are going to build more awareness about your finances and that awareness is going to create possibility. So I would invite you, like for the next 30 days, the next four weeks, put a money date on your calendar. Keep a notebook. I love telling my clients, like keep a notebook and answer these questions. Write them out. You’re going to have four weeks of information and you are going to be learning about yourself over those four weeks. And I guarantee you, after four weeks of looking at your money, you’re going to be like, oh my goodness, I’ve learned so much about myself. You’re going to start playing a different record. You’re going to start having different thoughts about how you manage money. 

And if you’re listening to this and you’re like, Kiena girl, it has been, oh, I know, I know, I know, I know, I know, I need to work with you. I would invite you to apply to work with me. So if you apply to work with me right now, the five month coaching partnership, we will start in August. Because at the time I’m recording this, this is July. So get on my calendar before the end of July and we will put a start date in August. So that means August, September, October, November, December are going to be the five months that we get to work together. Each of those five months, we have three coaching calls. They’re 45 minutes each. And we’re going to be going through your money. We’re going to set up a budget. We’re going to set up the three money bucket system, make sure that you know how much you’re going to bill, spending and saving. And then we’re going to look at like, what are your goals? How much debt are you trying to pay off? 

How much money are you trying to save? Are you looking to earn more money? And how much more money do you need to earn? And how can we increase what you’re putting into retirement? Like those are all the things that we are going to do in the five months, but that five months is going to be completely tailored to you and what you need. So we are going to do life together for five months, but you’re going to go into 2027, not needing to get finances together on your goals. You’re not going to need to scramble to file your taxes. You’re not going to need to scramble to pay for the holidays. All of those things are going to be things that we do together while you see your savings increase and your debt go down. So go to the link in my show notes or you can go to wealthovernow.com and apply to work with me. Thank you so much for tuning in. Until next week, have a great week.

Outro: Thank you so much for listening to Money Files. If you’re ready to take the next step to reach your financial goals, head to www.wealthovernow.com/appointment and let’s get started.

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