An American Problem?

I need to talk to you about an endemic problem afflicting many Americans…. the problem associated with tracking money. No, I am not talking about tracking money that finances terrorism or organized crime. I am talking about the need to track your money.

When I first published this article back in 2017, I cited an April 2014 Business Insider article that reported 61% of US adults did not track their money. That was only six years after the financial meltdown of 2008. At the time I thought that was pretty damning, but not surprising. Fast forward to 2025, after the post-COVID cost of living crisis, and those numbers reversed. A May 2025 report from Secure Data Recovery showed that 59% of Americans tracked their spending and 49% tracked savings. That’s a healthy turnaround, but it came with a kicker. Apparently 70% of the people who tracked their spending said it caused them stress.

As someone who has tracked their money religiously for the past 26 years, I can attest it takes time and discipline, which in and of itself can be stressful. I can also attest that sometimes the results don’t show what you want, which again may prove stress inducing. But that’s no reason for not partaking in the effort, though. I say that because I firmly believe that the insight gained from tracking your money is like a personal finance superpower.

Tracking Turned into Power

Tracking your money can force you into better spending habits. It also enables numerous retirement planning activities. For example, my money tracking efforts turned me into a relatively good saver, even if I did not know what I was saving for. It was also the mechanism by which I broke Mrs. Grumpus of her profligate pre-marriage spending ways, which in turn made us a family of savers.

By the way, don’t tell her I said that. It’s true but I do not want to antagonize her too much or she will shut my blogging down!

All joking aside, it would have been impossible for me to contemplate subjects like retirement or FI without knowing how much we spent and saved. When it came time to build my retirement plan in 2017, my previous 18 years of work paid off too. I was easily able to bring up average spending in most of life’s major categories and use those numbers in my retirement calculations. That level of detail allowed me to narrow down my level of uncertainty as I planned for my family’s future. It gave me a greater amount of confidence in my calculations.

Does that sound like too much work? That is OK because you don’t need 18 years’ worth of data before building a financial or retirement plan. Ideally, I would recommend that you track your expenses for two years before conducting long-term financial planning, but you could easily get away with just one quarter and some smart extrapolating. In other words, just three months. That sounds much easier, doesn’t it?

What Will It Take to Convince You?

Are you still not convinced? Well, let me ask a few questions:

• How can you estimate total retirement living expenses if you are not tracking your current spending for life’s major categories?
• How can you determine savings and investment goals to achieve Financial Independence if you do not know how much money comes in and goes out over a year?
• How do you identify and pay down debt?
• How do you calculate your savings rate?

It’s difficult if not impossible to do any of these things, and a myriad more, without tracking your money.

Demoralized yet?  Don’t be, because the good news is that there are now plenty of good-to-great tools out there to help you track your money, many of which are free or close to free. There is no longer a need to lock yourself away in your man/woman cave for nights on end like I used to do either. Many of the tools automate a lot of the work for you. Often just finding the right tool to fit your personality and lifestyle is half the battle.

I’ve used several software systems over the years and experimented around with a few spreadsheets too. I discuss all of these below. However, nothing is stopping you right now from simply cracking out a pencil and a piece of paper and tracking your money manually. If that suits you best, do it. My point is not to sell you on any one piece of technology or computer program, but to compel you to start tracking your money now.

With that said, the below sections represent the extent of my personal history and knowledge on the current money tracking options available to you:

Microsoft Money

I started using Microsoft Money (MMoney) in late 1999 when it came loaded on a computer I bought. Until then I tracked my accounts by hand so I immediately fell in love with this software platform because it saved me so much time. The ease with which you could import your bank, credit card, and brokerage data; manipulate it; and display it was without rival. Unfortunately, by the late 2000s Microsoft stopped supporting the active import functions, and then “sun downed” MMoney completely.

Possibly due to the cult-like following that had built up amongst it die hard users, Microsoft decided to offer the software for free online. It remains available today. None of the automated features work, but you can still manually import data (in Quicken formats no less) from your bank and brokerage; manipulate it, and display it just like the days of old. If I was a computer programmer, I would have ripped the code apart, figured out how to re-engineer the automated functions, and make them work again. Alas, I am not, so I eventually had to transition to software whose automated features worked in order to save some of my precious time. This led me to Quicken …

Quicken

I transitioned to Quicken 2016 at the end of 2015 because I missed the automated features on MMoney, and Quicken allowed me to transfer my entire MMoney history into Quicken format (with a lot of work). Quicken is by far the most powerful tracking, budgeting, and visual display tool out there today. It allows you to store all your data locally if you like, keeping it safe on your own system. Once I got the hang of its reporting system, I learned to break out my spending, saving, and investment performance; and visually display it. It had several great features, but none of them I considered indispensable.

While a good tool, I never fell in love like I did with MMoney. The ultimate deal killer for me was the Quicken interface, which is obtuse at the best of times. Whereas MMoney was forgiving if you made a mistake (like accidentally deleting a transaction), Quicken was not. Along with the price tag for the high-powered version and its inability to track accounts in multiple currencies, it ultimately just proved too problematic for me to stick with once we moved to New Zealand. You can find the latest that Quicken has to offer here.

Pocketsmith

In 2017, around the time I started this blog, I began to experiment with Mint. While my wife liked it and kept at it, I did not and (begrudgingly) kept using Quicken. I was still using Quicken, and my wife was still using Mint when we transitioned to Pocketsmith in 2023. Oddly enough, Mint disappeared as a software app in 2024, and its user were encouraged to transition to Credit Karma. A testament to how little people were using by that point.

Much like Quicken, Pocketsmith is not perfect, nor is it particularly cheap. Among its drawbacks are its lack of investment tracking beyond total values and its limited reporting capabilities. It is far more of a budgeting tool than a holistic piece of financial tracking and reporting software like Quicken. However, once you get past its moderate learning curve, it is definitely easier to use daily than Quicken. This review of Pocketsmith from Moneywise accurately sums up my feelings on its strengths and weaknesses.

That said, Pocketsmith offers one thing many other top-quality money-tracking programs do not: it allows the (almost) seamless automated downloading and tracking of totals and transactions across internationally denominated accounts. This feature is particularly beneficial for my wife and I as it saves a significant amount of time and effort in manually tracking and converting the values of our accounts in different currencies. It also takes those various denominated accounts and automatically calculates their value into the base currency of choice for your Pocketsmith dashboard. Thus, your net worth is always on display, accurate, and in your preferred currency.

Banks

Many banks these days offer online money tracking software as part of your membership. It is typically found after you log into your account. Several of my banks allow me to add accounts from other banks and credit cards. During my transition period to Mint, I experimented with using USAA’s online feature. Since I kept my investments with their online brokerage for a time, it seemed like an easy win. I added all my other bank accounts and credit cards to their online software and started to update transactions. It was all fairly straightforward. However, its lack of an in-depth display or visualization tool made me give up. Being able to view my cash flow across all accounts for a month, a quarter or a year is important to me. If it is not a big deal for you, then maybe simply using your bank’s software is the way to go.

Other Software Programs

There are other platforms out there on the interwebs that you can use to track your money. While I have not used them, do not let my lack of experimentation stop you from exploring to find your perfect fit. One platform you might want to consider is Personal Capital. The Mad Fientist, a blogger who I have mentioned previously and have a lot of respect for, is apparently a big fan, and his article/advertisement makes a compelling argument if you are someone with a lot of investments. On the other end of the spectrum, if you are simply in need of a money tracking and budgeting tool, you may want to consider YNAB – You Need a Budget. My brother, Grumpus Brotherus, has used YNAB for years and this is what he had to say about it.

Spreadsheets

Finally, there are dozens of spreadsheets online with built-in calculations able to assist you in tracking your money. One spreadsheet I highly recommend is located at the Optimal Living Daily podcast site. Justin Malik, the creator of the podcast, created a spreadsheet to help himself get out of debt. It changed his life so maybe it will change yours. All you do is sign up to his email distribution list. If that is too much of a commitment, Mad Fientist also has a spreadsheet that I have experimented with. It not only helps you track your money but will also help you calculate your time remaining to FI.

Ironically, this article was originally published in 2017 before artificial intelligence (AI) was thing. However, like many people in 2025, I guide a lot of my internet research through an AI program (Microsoft Copilot in my case). As a time saver, it cannot be beat! Thus, when I asked it for some of the best spreadsheets used to track money within the FI community currently, it conveniently spat out the chart (below) of five different options, which I include with links to their websites. That said, maybe the most useful resource that Copilot provided was this link to a Well Kept Wallet article which highlights 10 different spreadsheets that can help you track your money.

Spreadsheet	Best For	Key Features	Cost
Financial Independence Spreadsheet	FI progress tracking	Net worth, SWR, savings rate, visualizations	Free
Reddit FIRE Spreadsheet	Community-driven customization	Dashboard, dark mode, detailed FIRE analysis	Free
Tiller Net Worth Template	Automation lovers	Bank sync, flexible templates	$79/year (30-day free trial)
Johnny Africa FIRE Spreadsheet	FIRE planning	Net worth + budgeting + FIRE milestones	Free
Poorer Than You Tools	Beginners	Simple, adaptable spreadsheets	Free

Speaking of AI

I think that the money tracking software business would be a great use case where the power of AI could truly make a positive difference for the customer. It would not only prove incredibly useful as a time saver for labeling transactions but also provide analytical insights that we mere mortals might otherwise miss. Alas, kneeling down in acceptance to our new robot overlords is far off topic of this post, but determining if Sky Net can help you track your money easier (and unlock your financial superpower) may be worth a future article for the blog. What do you think?

Conclusion

So that is my pitch on the need to start tracking your money. Congratulations on making it this far in the post. Notice how I did not try to sell you on the need to budget or create a spending plan? “Why” might you ask? Well, I believe that once you start tracking your money routinely, you will naturally start to budget as a result. Maybe not formally, but at least loosely. Once you see the amount of money you spend drinking at the pub on weekends, on coffee in the morning, or on clothing; you will start to question the need. Don’t believe me? Start tracking your money and prove me wrong…