Breaking the Cycle of Repeated Financial Mistakes

Human beings are creatures of habit. Most of the time, those habits are a good thing – they ensure that our basic needs are met pretty efficiently and we get the core things done that we need to get done in a day.

Sometimes, however, those habits work against us. They can continually keep us in a bad financial position, even when we consciously recognize the habitual mistake we’re making.

It even happens to me.

My worst financial habit is buying Kindle books and, occasionally, boardgames without looking at my “hobby/entertainment” budget for the month. Rather than actually looking at how much I have left in that budget category, I’ll just estimate quickly in my head that I have enough left over and then I go ahead and make that purchase. Sometimes, that takes me over my spending limit, which means that I “borrow” from next month’s budget, which is where the cycle of repeated financial mistakes gets started. That’s because next month, I don’t reflect on the fact that my budget is a little smaller because of my overspending from the previous month, so I overspend that month, too.

I am extremely glad that this relatively minor thing is currently my worst repeated financial mistake. The truth is that, not too long ago, my life was riddled with similar repeated mistakes.

I used to go to a coffee shop every day and pay for it on my credit card. I didn’t order anything that I couldn’t make from home there and I didn’t bother to really keep track of the spending, either. It was just my normal habit.

I used to go to the bookstore after work twice a week and walk out with two or three books in hand each time. Again, I didn’t buy anything I couldn’t already get from the library and it was rare that the books were actually reference books or books that I would repeatedly read. I didn’t bother to really keep track of the spending there, either. It was just my normal habit.

Every day, after work, I used to walk across the parking lot from my apartment to a convenience store, chat with the person behind the counter that I had come to know pretty well, and buy a Gatorade and sometimes a slice of pizza. I really didn’t need that pizza (or the Gatorade, to be honest, though I could have bought that in bulk elsewhere for about a quarter of the price). I just did it out of routine, and, as with the other routines, I didn’t really think about keeping track of my spending. It was just my normal habit.

I used to maintain subscriptions to about six different online role playing games, even when I wasn’t actively playing them. When I saw a new MMO that looked interesting or that my friends were playing, I’d jump in and subscribe and then just leave the subscription running. I didn’t really think about the cost of it all. It was just my normal habit.

Whenever I went grocery shopping, I would just go there with an idea in mind that I had to plan for three or so meals. I’d wander through the aisles, grab a bunch of things that theoretically fit together as meals, and usually throw several unnecessary items in the cart to boot. This was just my normal meal planning and food buying strategy.

These habits and routines were part of the normal bedrock of my life. I simply settled into them during the early days of my professional life, back when I felt absolutely flush with money due to the fact that I was now working at my first “real” job with a “real” paycheck. I was much more concerned with establishing an “adult” life with lots of the little pleasures and treats that came with it than I was about the dollars and cents.

By the time I realized what I was doing to my financial future, I was already very entrenched in these routines. Those routines were my sense of “normal,” and the thought of disrupting even one or two of them seemed terrible. I focused deeply on the negative aspects of disrupting my routines.

Even worse, I often didn’t even see these financial mistakes. They were so embedded in my normal routine that they didn’t even show up on my radar as a financial mis-step. I looked instead at the things I did irregularly and focused on changing those things instead, which helped a little but didn’t bring about the profound change that I wanted. I became obsessed with things like optimizing the cost of visiting my parents, which was something that happened a few times a year, while initially ignoring some of my daily habits.

Even when I started to really notice the negative financial impact of those habits, I often just continued to do them anyway without even thinking of the negative impact in the moment. I’d go to the coffee shop in the morning and not even think about the negative financial impact, even though I was aware of it. I wouldn’t even think about another choice.

Over time, I managed to break all of these bad habits and repeated financial missteps. I don’t drink coffee hardly at all any more, though I don’t feel guilty in the least if I drink a cold afternoon coffee (my preferred way of drinking it these days). I get many of my books from the library (though I still do buy a Kindle book or two, as I mentioned at the start). I use a much smarter meal planning routine, and I rarely go to any convenience stores any more.

The financial benefits were enormous, to say the least.

I was able to change those poor financial routines by adopting a few smart strategies for breaking those kinds of habits. Here are the ones that really do the trick.

Identify overlooked habits by using data

Sit down with your credit card statements and your bank statements and look for transactions that repeat regularly, especially ones that repeat multiple times per week. What are those transactions? Chances are those transactions are a sure sign of a bad financial habit.

Go through each one of those repeated transactions and identify what it is that you’re doing over and over again. Maybe it’s a regular stop at a store of some kind. Maybe it’s a regular online purchase.

Whatever that routine is, ask yourself whether or not you really need to continue it, or whether there’s a way to change it to cause you to spend less money, or whether there’s a way to adopt a different routine that achieves a similar effect in your life.

If you need some inspiration, add up how much this routine is costing you each week or each month. What you find from that simple arithmetic will probably surprise you. Take my previously mentioned coffee shop routine, where I spent a seemingly minor $7 each morning on a coffee and a bagel. Over the course of a typical month, that added up to over $150.

It’s those repeated purchases that indicate routines that we’re probably not thinking about in terms of their long term financial consequences.

Set up short-term “challenges” for breaking habits

One of the best tools I’ve ever discovered for establishing a new habit is the “30 day challenge.” It’s simple: for the next thirty days, you simply challenge yourself to focus on and adopt a new habit of some kind or eliminate a habit of some kind.

You might challenge yourself to avoid alcohol for thirty days or eat only at home (and brown bagging when necessary) for thirty days or not going to the coffee shop for thirty days or replacing bookstore visits with library visits for thirty days. It can be whatever you’d like it to be, but a good goal for eliminating bad financial routines is to either use a thirty day challenge to completely halt that habit in its tracks or completely substitute a new habit for the old one.

The key is to constantly remind yourself of this thirty day challenge. Do whatever you need to do to make sure that the challenge is front and center in your life.

I use two strategies. First, I use a “daily checklist” (something I may cover in a future post) that I follow each day and if I’m establishing a new habit that habit goes on the checklist. Second, my phone reminds me of the new habit I’m trying to establish several times throughout the day by sending me “reminders.”

Together, those things ensure that the new habit remains center of mind throughout the day.

Look for triggers for those bad habits and modify or eliminate those triggers

Why do we choose to continue those bad habits? What triggers us to continue them? Figuring out our triggers for our bad financial habits can be vital in fixing them.

For example, I came to realize that my ordinary routine of getting home and quickly feeling thirsty usually led me to walk over to the convenience store. So, what I started doing was keeping a really tasty beverage in the fridge. I started preparing some citrus water (something I really like – basically just citrus fruits and a bunch of honey left sitting in water all day) in the morning, and the process of doing so reminded me of that water during the day. When I got home, I’d grab that citrus water bottle and my thirst would be quenched, wiping out the main trigger for going to the convenience store. (It was also a lot healthier.)

My biggest triggers for stopping at the coffee shop and the bookstore came from my commute, so I spent some time devising a parallel route home, one that actually turned out to be a minute or so shorter than my previous route as it took me down a road with a few less stoplights. Simply not driving by the bookstore each morning went a long way toward quelling my desire to stop and buy books, and the same thing turned out to be true about the coffee shop.

Just look for the exact moment you make the decision to engage in a bad financial habit, then ask yourself what you can change about your routine to reduce the chances of that trigger happening. Often, by changing something completely unexpected, you can completely wipe out that bad habit trigger and suddenly find yourself saving a lot of money.

Replace the habit you’re trying to break with a new one

Almost every bad financial habit you have can be directly replaced by something better. It just takes a conscious effort to switch your “default” behavior to the new behavior.

Take grocery shopping, for example. My old routine of simply going into the store and grabbing things for a few meals (and a lot of other unnecessary items) was an expensive one. What I simply tried instead was figuring out the meals at home and making a grocery list based on those meals.

At first, this seemed rough. I felt like making this list was going to cause my time spent on the task of “getting groceries” much longer than before because I was sitting at home making a list instead of actually shopping. What I learned pretty quickly, though, was that I saved so much time in the store by having a list that I recovered even more time than I spent writing the list. I also saved a lot of money and actually had good items at home for meals. (I now have a full routine for this that involves looking at grocery store flyers as a basis for planning the meals so that I “automatically” buy on-sale items at the store.)

I directly replaced my bookstore stops with stops at the library. However, instead of going to the bookstore twice or three times a week (as I noted above, I killed this off by changing my commute), I went to the library once every two weeks or so and checked out several books at once.

I directly replaced the stop at the coffee shop by drinking a beverage immediately after getting to work. At first, I drank coffee, but before long I switched to drinking water in the mornings (coffee made me feel jittery in the morning).

How can you make a substitution for some of your financially costly routines? Look for ways to maintain what you really value from a routine but without the expense and then focus on really hammering home that routine change until it feels natural.

Use positive talk; if you need to self-criticize, always include a “but”

When you think about your life, particularly when you’re thinking about recent changes that you know are positive, try to avoid using “negative” talk to describe that change. Use “positive” talk to describe it. In other words, focus on the good things that this change is bringing into your life.

It’s hard to always police one’s thoughts like that, of course. Sometimes we all think negatively about things. If you find yourself doing that, tack a “but” on the end of that negative thought and bookend it with a positive ramification of your change.

It’s simple: if you think more positively than negatively about a change in your life, you’re likely to stick with it. If you look at the benefits above the challenges and drawbacks, you’ll want to keep doing it. That change will feel good.

So don’t dwell on the aspects you’ve lost. Focus instead on what you’ve gained and if you ever find yourself considering the pieces you’ve lost, remind yourself immediately of the positives as well.

Visualize your life without this bad routine or with a better one

Another great strategy is to simply spend time visualizing the part of your day where your routine has changed. Mentally walk through your morning routine or your commute or what you do when you decide to go grocery shopping or when you might pick up a drink and visualize yourself actually adopting the new routine you’ve decided on.

I find that such visualizations are a great thing to do while driving. I’m constantly thinking about my life while driving and looking for ways to improve what I’m doing. Simply imagining a part of my life where I’m engaging in a more positive routine really helps me actually implement that routine in my life.

For me, repetition of the visualization seems to help, as does adding as much detail as possible to the visualization. Try to make the visualization seem as realistic as possible, even with some of your normal foibles in the visualization. The more real it seems, the more your brain will buy into it.

Surround yourself with people who don’t include this bad habit – or similar ones – in their lives

If you find yourself constantly buying books, hang out with people who instead use the library all the time. If you find yourself stopping at the coffee shop all the time, hang out with people who don’t drink coffee or who just drink it at work.

The idea is that if you hang out primarily with people who don’t treat the habit you’re trying to break as a norm, then it becomes easier to break that routine. They won’t bring up that routine in conversation. They won’t practice it themselves. They won’t encourage you to practice it, either.

It’s also a lot easier to adopt new positive routines if you’re in a community or social circle that practices those routines. If many of the friends you hang out with have a regular exercise routine, it’s much easier to adopt such a routine for yourself, for example.

Accept that you will fail occasionally, but recognize that it’s not a reason to give up

You are going to sometimes fail. You’re going to slip back into a familiar routine, almost completely without thinking about it, and then you’re going to cringe at your own silly mistake when you realize your mistake. It’s going to happen.

First, don’t beat yourself up over it. Everyone makes mis-steps, especially when they’re learning a new life routine. It’s part of the process of changing a normal routine.

Second, consider why you made that mistake, but don’t dwell on it. What triggered the mistake? What can you do to eliminate that trigger in your life? Maybe it was a personal relationship that did it, in which case you can spend less time with that person. Maybe it was your commute. Maybe it was an elevated stress level. Whatever it is, look for a way to alter it so it doesn’t set the stage for more mistakes.

Finally, remember that taking one step back isn’t the end of the world if it’s paired with ten steps forward. You haven’t lost all of your progress because of one misstep. You’re still in a better place than you were at the start and you can keep pressing forward from here.

Final Thoughts

Breaking a repeated cycle of mistakes can be very difficult, but it’s also one of the most financially rewarding things you can do. It enables you to get a much firmer grip on your money. It also goes a long way toward restoring the joy of some of the things you now find routine – for example, I love going to the coffee shop as a rare treat, but when it was a routine, it was very ordinary and forgettable. Plus, doing it this way is far cheaper.

Good luck to you on whatever bad financial routines you’re trying to crack!

Trent Hamm

Founder of The Simple Dollar

Trent Hamm founded The Simple Dollar in 2006 after developing innovative financial strategies to get out of debt. Since then, he’s written three books (published by Simon & Schuster and Financial Times Press), contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.