Just Pick One: Choosing a Bookkeeping System

written by Bari Tessler August 3, 2023

Dear Money Adventurer,

So, you’re working through your deeper “money stories”, gaining clarity all over the place, and then. . . Boom. Stopped in your tracks around this question:

“Which system should I use to keep track of my money??”

This is a big, huge hang up for so many people journeying on the path of financial transformation. In this article I’m going to do my darndest to help you move through this piece once and for all, my friends.

Indecision can look different for different people:

Some of us just feel paralyzed and don’t track at all.

Some of us feel we need to try every single option. We want to taste ‘em all. We sign up for everything, wrack our brains with pros & cons, and can’t seem to commit to any of them.

Some of us had a great system working for a long time and then a big life event happened (ie: baby, health scare, change of job, move, etc) and you stopped using your fabulous tracking system and are now trying to figure out if you should go back to your old system or start over with a new bookkeeping system.

The emotional content that comes up is often around . . .

  • Wanting to do it “right” and to find the “perfect” system
  • Wanting to know everything, or feeling confused about what we don’t know
  • Wanting to understand all the options, fully & completely
  • Thinking it’s way more complex than it really is, or needs to be
  • Consciously or subconsciously avoiding choosing because then we’d have to look at our numbers and we know this can feel scary
  • Thinking that once we choose, we’ll never be able to change our minds
  • Still doing the numbers in our head and not sure of how/why to put it into a separate system
  • Had a great system in the past but suddenly stopped during a transition
  • Having tried systems in the past that did not work.

Here are a few invitations, and a bit of information to help you move through these pieces . . .

1. Let’s get super duper clear on what an accounting system actually is. (It’s simpler than you think!)

There are three important components to any accounting system – tracking + reviewing + budgeting.

An accounting system is the tool you use to keep track of your income, expenses, assets and liabilities. It can help you review how the income is coming in and where you are spending your money. And it can be a budgeting tool to help you project your financial intentions, adjust your spending and learn from your numbers.

That’s it, folks! That’s it.

2. There is no perfect system. Repeat: There is NO perfect system.

Research is good. Educated choices are good. Knowing your options is really good!

However, there comes a point where we simply need to choose. There comes a point where the weighing of pros and cons becomes unproductive. It can be a loop, which always comes back to the same conclusion: there is no perfect system!

When we get to this place, we simply need to get clear on which features are most important to us, and choose the system that is closest to our needs.

It’s actually less important which tracking system you choose, and more important that you choose and USE it.

We never really, truly know until we’re in there, living and breathing our system, anyway.

3. It’s not a lifetime commitment.

Although it’s important to really commit and dive in, it’s also good to know that you’re not signing your name in blood forever.

You can always pick one system, and then a year later, or 5 years later, switch to another. Life is a long time. Our needs change, our businesses change.

Choose a system that can support you now, and trust that you will make changes when or if you need to.

4. Yes, it’s uncomfortable. Stay.

For some of us, once we finally get into a new system, it’s smooth sailing, easy peasy. If that’s you, go forth, and yay!

For MANY of us, it’s soooooo uncomfortable! It feels sticky. You get in there and don’t even know what questions to ask, what to look at, where to start, how to get it all set up. You have tech glitches. It doesn’t have features that you wanted, and didn’t even know you wanted!

There is discomfort in the learning curve. Always.

Here’s the thing: we should have been taught this in grade school in small increments! We weren’t. So here we are as adults trying to catch up on the learning here, and it’s uncomfortable.

One of my students said to me recently, about getting into her tracking system: “It feels like I’m looking up at a 14-er”

Yep. Exactly. It is! Knowing that, what kind of supplies do you need for the journey? Do you need to hire a trainer to hold your hand? (I did.) Do you need to schedule time for this? Do you need to bring chocolate? Do you need dance breaks?

Stay with it. Feel that discomfort. And keep going. (Needless to say, this invitation applies to just about ANY growth of any kind . . .)

5. Implementing a bookkeeping system is emotional work, too.

This is so easy to forget! We think it’s all about figuring it out, setting it up, and doing it right.

Meanwhile, behind the scenes all of our money stories, money hurts, money fears, and money feelings are going crazy!

Simply reminding yourself of this emotional context helps it relax. Remember, body check-ins are your most trusty tool for moving through the emotional muck.

A few pros and cons about the main players:

Let’s dip into the nuts and bolts for a moment. Here are a few choices, and a few key distinctions.

(Note: These are just a few of the many systems out there. And, there are SO many more features, and this comparison is not complete. Also, “user-friendly” is relative and so personal. Get in there and find what works for you. )

Mint.com: Mint is for personal finances. Pros: It’s simple online, free and syncs up with your iphone and ipad. It downloads all of your transactions for you, automatically. Could-be-cons: Not all banks or credit unions sync up. Plus, the main expense categories are set – you can’t alter them or customize them, but you can add your own additional and sub-categories. Also, there are ads that pop up. It’s a very simple tracking system that shows your income and expenses at a quick glance. And, it’s a good first option to get you going. Learn more about Mint.com here.

Quicken: Quicken was also created for personal finances. However, it has more robust features than Mint – you can customize all your categories and budgets. You can run more customized reports. You can choose to download your transactions (like Mint) or enter them by hand. You can have a few different bookkeeping systems each in its own file. (ie: one for personal, one for joint). PC or Mac versions are available. Learn more about Quicken here.

YNAB: I added this one to the list because my Art of Money community is going crazy about it. It’s their new top favorite. One of our AOM students said: “Quicken was a tool, YNAB is a lifestyle”. It’s a personal bookkeeping and budgeting software. I hear their tutorials and training are top-notch. Plus their customer support is outstanding. And, the level of awareness and empowerment it is bringing to my community makes my heart-glow! Learn more here: YNAB.

Quickbooks: This is a bookkeeper’s favorite system for tracking business finances. Quickbooks has special features that are especially created for businesses, like Invoicing, Databases, Reporting and Payroll. It has a great chart of accounts that I love. You can customize like crazy and even add values-based names. It’s pricey. I have been using it for years for my business and I love the clarity + reporting that I get. PC or Mac versions are available, although the PC versions are much better. You can have a separate file/separate bookkeeping system for your personal. If you want to learn and use one system, you can do this. Your personal system would simply not use the more robust business features. Learn more here.

Money Grit: This bookkeeping system is created by our dear friend and colleague, Karen McCall, Founder of Financial Recovery Institute which she created in 1988. There are both personal and business bookkeeping options. This is the only system created by a Money Coach so she really understands what’s needed for our tracking systems. Learn more here.

TillerHQ: If you love spreadsheets, like my husband does, you’ll love this option. This is an excellent option for personal finances. It includes many different spreadsheet templates to track your income and spending, to pay off debt, to make a spending plan or to track net worth. People find it very flexible and easy to use even if you are not a spreadsheet whiz to start with. Also, there are no ads with this one (like there is with Mint) which is good. Learn more here.

Xero: An international option for small businesses. Learn more here.

Allo: This is a simple app that brings in a mindfulness practice. We just heard about Allo, and we’re excited to explore it! Learn more here.

Here’s how I’ve done it.

When I started out, I needed hand-holding. I hired someone to train me, step-by-step, how to use Quickbooks. For about six years, I used Quickbooks for both business and personal. Business was in one file, and personal was in another file – all within Quickbooks.

Then, when my hubby and I joined finances, I kept my Business in Quickbooks and moved our personal finances to Quicken (simply because he had already been using it). At the time, Forest had a very simple freelance business, and we also tracked that in a separate file in Quicken. We did this for about 4 years.
One day, my Quicken froze. After this tech glitch (hey, it happens), Forest took over our personal finances and set us up on Mint.com and then more recently moved us over to TillerHQ, which has fabulous spreadsheets that he loves.

My business finances have stayed on Quickbooks for 22 years but now I have a bookkeeper, Jess Salzman from Heart Based Bookkeeping, who does all of my Art of Money business bookkeeping. I happily handed it over to them in 2014 and they have been handling my bookkeeping since.

It’s a windy road, folks. Your job is to find the system that works for you right now.


Just pick one and go for it, trusting you will learn more along the way and have more clarity and questions as you go.

You choose:

  • Learn the system on your own. Get in there and figure it out.
  • Get additional online training online. Some systems have great video tutorials and community support.
  • Hire a bookkeeping trainer to hold your hand every step of the way.
  • p.s. A bookkeeper trainer can also help you choose the best system(s) for you.

Remember, we can always begin again, and ask for a new start with a clean slate.

Choose one.
Begin today.

We are rooting for you!

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