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4 Habits to Eliminate Second-Guessing About Money

This morning, I spent a silly amount of time asking myself how I should spend my time. On writing days like today, I like to ride my Onewheel down to the coffee shop near my house. It’s only about a ten or fifteen-minute ride, and I always enjoy it. Maybe it was because it was just a little rainy or because the kids were extra cranky, but I just couldn’t decide if it was worth the time to leave home this morning. 

It wasn’t until I planned out my day in a time-blocking app that I realized I had plenty of time to travel to and from the coffee shop and also get my work done. In fact, the decision was easy, I just didn’t have the information I needed. So instead, I actually did waste 20 minutes second-guessing. I sure wish I had that time back!

Is it worth it?

We ask this question all the time about all sorts of things. I asked whether it was worth the time to go out this morning. You might ask if it’s worth the energy to plan a lunch date with a friend this week. Or maybe you’re pondering whether it’s worth the calories to enjoy a slice of mediocre sheet cake at an office party.

The question of 'is it worth it?' often comes up when we’re dealing with a finite resource, but we ask it about money more than anything else. 

For me, not knowing how to answer that question about money is one of the worst feelings in the world. I hate uncertainty around spending, because the way we spend money is one of the most important things in our lives, just as important as decisions about our health and about our relationships. 

Money is important because it is the product of all your time and effort. It’s our creativity, focus, and energy quantified. It’s an extension of you.

So knowing how you want to spend that money feels crucial. And not knowing? Constantly second-guessing all your spending decisions? That’s just the worst. Because what you’re really wondering when you ask if you’re wasting your money is if you’re wasting your creativity, focus, and energy. 

What if I told you there is a way to know your spending is worth it, every single time?

Second-guessing comes in all shapes and sizes

I’m not just talking about second-guessing big ticket expenses. Deciding how much to save for retirement, how big your mortgage should be, whether you should pay for all of your kids' college—we all expect those kinds of decisions to be tough. But second-guessing extends to whether you should go out to eat tonight or cook, whether you should buy a new dress, whether you should say yes when your cute kid gives you puppy eyes and asks to go out for ice cream. 

We’re all shoulding all over ourselves with every little purchase. It’s pernicious. It’s exhausting. Constant second-guessing is the root cause of money stress. 

And the worst part is no one seems to be imagining a better way. I look at the personal finance blogosphere, a million memes on the internet, and just what my friends say every day. And the message I get is everyone looks at money as this big bummer. I’ll never be able to spend worry-free (unless I win the lottery), I’ll never be able to take joy in a purchase (without feeling guilty), I’ll never be able to see money as anything more than a chore to manage. So I can either distance myself from my money and ignore how I spend it or, at best, I can exert some white-knuckle control over it in the name of “being responsible.”

There's a better way

Can you imagine the relief of knowing your spending was worth it? Can you imagine never second-guessing even the smallest of purchases… ever? What if you can recognize the importance of money while also not stressing over it? What if you could spend freely and with joy all day, every day?

You can. We all can. All it takes is replacing old habits that are no longer serving us with a new set of habits that turn money on its head, that will help you see opportunities instead of problems. All it takes is planning before spending, thoughtful anticipation of the future, making some space between when you earn and spend, and being willing to adjust your plan when circumstances or priorities change, all with your eyes wide open. 

Let’s go over those habits one by one and I’ll explain how they eliminate second-guessing. 

Habit One: Give Every Dollar a Job

Every time you get paid, decide how you want to spend it by allocating all the new money into spending and saving categories. It’s such a simple habit, but it makes all the difference, because you can make all the decisions at once, when you have all the information you need in front of you and when you’re in a good frame of mind. This simple habit is absolutely life changing. It means you can unveil your highest priorities and make sure your money flows toward the things you value, not toward the things you don’t. 

And it gives you permission to spend. You know the feeling you get when someone gives you a gift card to your favorite store? It’s the best, because they’ve removed the second-guessing about that money. You have to spend it on something you enjoy. Imagine if you could get that feeling for all of your money. It’s magic.

Habit Two: Embrace Your True Expenses

Habit two is all about anticipating the future, but acting now. Prepare for all the expensive, surprise expenses that don’t happen every month by setting aside a little for them regularly. Embracing your true expenses helps you acknowledge the things you truly value. You may not like it when you have to pay for a big car repair, but you do it because you value a working car pretty highly. Acknowledge those values every single month by setting money aside for them. 

Then watch the daily second-guessing start to fade as you gain more and more security and a greater sense of well-being. When I go out to eat at a restaurant, I don’t have to wonder if I'm actually eating my car. I don’t have to wonder if all these little expenses will add up to put me into trouble when something unexpected happens, all because I’ve acknowledged those things in my plan already.

Habit Three: Roll With the Punches

Habit three, my personal favorite, acknowledges that you can’t see everything coming. Anytime you want, you can change your spending plan. We really mean it when we say roll with the punches

When you make a plan, you can hold it loosely knowing that when circumstances or my priorities change, it’s okay to change my plan. In fact, it’s the smart thing to do. You are the best person in the world to know whether a change needs to happen. 

Now wait a minute? Isn’t this just second-guessing? Maybe, but the difference is you’ll know exactly what you’re giving up in order to change your plan. Because of habit one, you now have a framework for making a trade-off so you can see that making a change is perfectly fine. Or maybe the trade-off is not worth it and you decide to stick to your original plan. Now you know! You can relax. It’s changing your mind (or not!), without all the dread.

Habit Four: Age Your Money

Habit four says when you’re giving every dollar a job, consider expenses this month, but also expenses next month. Once this month is all set, start setting money aside for all your priorities in the next month. The more you intentionally set money aside in the future, the more that will snowball until you can live on last month’s income. 

Imagine getting paid and saying “I don’t even need that paycheck for 30 days.” How much peace would that give you? How much more space will you have to make intentional decisions about your spending rather than constantly second-guessing every single time you pull out your credit card. 

When you break the constant earn-spend cycle, you’ll break the constant second-guessing too because your decisions will become more intentional and better reflect who you are.

That’s the YNAB Method—a different way, a better way to live. It’s just four habits that will get you thinking differently about money than everyone else. These habits are simple, easy to understand, and we’re here to help you make them a part of your life. And the beauty is, anyone can do it. Will you? 

Start practicing these four powerful money habits in your life and eliminate second-guessing for good. It all starts with a YNAB trial—it’s free for 34 days!

YNAB IRL: From constant fear to freedom to travel

Meet Meagan, a Behavioral Health Technician from Mississippi and dedicated YNABer! She overcame second-guessing her spending by flexing four healthy money habits.

I started using YNAB consistently in 2021. Back then, my poor spending decisions meant that my husband and I were frequently left with a low account balance. My net worth was at the lowest in my career.

Still, I kept using YNAB's four rules. Eventually, my financial situation became much more predictable and comfortable. My husband and I have been able to stay on top of our bills, take a few vacations, save for Christmas each year, pay off a credit card, create an emergency fund, give to charitable causes, and keep our finances in perspective. We have enough money in our checking account to not live in constant fear of overdrafts, and so much stress regarding money has been lifted from my mind.

Now, my husband and I like to save for travel and trips. I am also saving some money to obtain my Master's degree and become a professional counselor.

Thanks YNAB for changing our lives for the better! No more mental gymnastics, no more checking my balance before making every single purchase, so much less worry, and feeling proud that I am doing a good job.
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4 Habits to Eliminate Second-Guessing About Money