The Ultimate Guide to Working with a Bookkeeper (Or Not!)

One of the most common snags I see people hit when they begin their money practice is around the question: should I hire a bookkeeper or not?

First of all: this is a highly personal decision — just like everything else related to money! Ultimately, the very best decision for you is the one you feel most comfortable with.

AND I have a ton of great information, resources, and processes for you as you face this question. Here it all is, in one place. (Well, a lot of it, anyway!). But first …

Remember: This decision is emotional work, too.

This is so easy to forget!

It’s easy to get caught up in the mental chatter and nuts ‘n bolts, here. We think it’s about making “the right decision,” finding the best bookkeeper, setting everything up, troubleshooting our own systems — all that exterior, technical stuff. Meanwhile, within ourselves, 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.

So. Deep breath. Light a candle. Whip out the dark chocolate. Insert body-check-ins galore. You can do this.

True Story from my “Die Hard DIY” Days

Back in the day, I was on a mission to make sure everyone did their own bookkeeping. I never suggested people work with a bookkeeper, because I was convinced everyone needed to empower themselves by looking at their numbers and getting real about their relationship to money. (With chocolate, of course!)

You see, up until my late 20’s, I was a full-on creative, African dancer, authentic movement, psychotherapist-in-training kind of gal. Anyone who lived with me during graduate school for psychotherapy knew that I would simply throw away my bank statements. (“What does one do with such a thing???” I thought.)

This was the perfect metaphor for my relationship with money and my lack of consciousness, understanding and respect. Back then, money & I had an estranged relationship, in a big way. Plus, my “I’m not good at math” story somehow got blended into my relationship with money + bookkeeping, so my head stayed firmly in the sand when it came to money.

Then one fateful day, someone turned me on to Excel and Quicken. Holy moly! It felt like the heavens parted. Lo and behold, there was another side of my brain — and it worked! How exciting! I felt empowered and confident with a system — a money system. I was shocked and delighted.

It quickly became clear to me that there was more going on here then just regular old bookkeeping + number crunching. As a creative-sensitive gal, I could FEEL it: a tentative bridge between heaven and earth, between sacredness and groundedness, creativity and money.

As strange as it seemed at the time, I knew this “bookkeeping stuff” was going to help me with everything: my life, my work, and my relationships. And I heard the intuitive whisper that I was not alone in my need for this work. That one day I would craft this into a process for my entire community.

Everyone around me probably thought I was taking a seriously odd detour away from my life’s work. But thankfully, I knew I was onto something essential, and trusted my intuition.

So, I jumped tracks in my career. I learned everything I could about bookkeeping and tracking systems. I trusted I was on a stepping stone to my real work. And I hung up my shingle as a bookkeeper.

Here’s what fascinated me most, at first. When prospective clients found me, they barely ever asked about my credentials, skills, or qualifications. Instead, they said, “HERE, take my books away from me. Do them for me. Pllllllease. I JUST DON’T WANT TO HAVE ANYTHING TO DO WITH THIS!”

For a few years, I did bookkeeping for people. I learned a lot, and am so grateful to have harnessed these skills.

Looking back now, it’s easier to connect the dots. Psychology & healing work —> bookkeeping & numbers & systems —> now: an integrated framework bringing together these two seemingly distant worlds, at the heart of The Art of Money program.

Often, what we resist most holds the biggest rewards.

Learning to do my own bookkeeping was massively healing and empowering for me. And I presumed the same would be true for many of the people who wanted nothing to do with their numbers. But here’s another surprising thing I learned:

The simple act of hiring a bookkeeping can be a huge leap of courage!

Yes, even if you’re not doing all your bookkeeping, yourself. For many people, attending to their numbers in this way brings more awareness and healing than ever before.

For me? I did my own bookkeeping (on QuickBooks) for 12 years. I learned all the in’s and out’s of doing it myself, reading reports, etc. Finally, last year, it was time: I handed everything over to a great bookkeeper. (Her name is Jess Salzman, and she is amazing! You can find her here.)

I’ve learned so much from both sides of this: doing my own books AND entrusting them to a financial pro.

Like every money decision, very personal things are at play here. And your answers will evolve over time.

So. Is hiring a bookkeeper the very, very best thing for you, for now? Maybe! Let’s dig in and get some clarity here.

Should I Hire a Bookkeeper or Do It Myself?

Already KNOW you want to hire a bookkeeper? Hop straight to the 16 questions you should ask before hiring one.

In my years as a bookkeeper, and years since as a financial therapist, I’ve heard a lot of bookkeeping love stories, and bookkeeping heartbreaks.
Here’s one I’ve heard a lot:

“I gave over my bookkeeping to a bookkeeper, and then {insert disempowerment or disaster experience}, so I started doing it myself, learned the system and finally felt so empowered around my finances. Then, I decided to hand it back over to a new bookkeeper, with a completely different perspective, and it’s such a better experience.”

Here’s one more:

“I’m a creative, therapist type guy. I did some great foundational work in The Art of Money, and got turned on to Mint.com, a free online tracking system. But I still needed a more robust stacking system for my business. I made myself crazy trying to find the perfect one. For a solid year. Finally, I got someone to teach me QuickBooks. And it’s been so good: it’s helping me grow my income, and I’m feeling mega-empowered with this new knowledge.”

There are so many ways to forge a conscious money path. It’s about finding the right one for you, my friend.

I’m not quite as die hard as I used to be about do-it-all-yourself bookkeeping + chocolate. However, I do recommend doing bookkeeping your own bookkeeping, even just for a period of time (3 months, 6 months, a year?) before hiring a bookkeeper.

I cheerlead my Art of Money students to get in there, learn the language, learn a tracking tool, and understand their money patterns in a very hands-on way.

Getting the heebie-jeebies? You’re not alone.

If doing your own bookkeeping seems scary to you (and it does to many of us at first), see how can you re-frame it. Remember: this is not a lifelong sentence. It’s just a short period of time to experiment and check things out.

After you do your own bookkeeping for awhile, a few different things might happen:

#1: Perhaps you will pass that puppy right along to a bookkeeper.
You’ll know it’s time to do this if you have learned:

• the language of numbers, money, and bookkeeping
• how to navigate around a bookkeeping system
• how to read your income and expense reports and review your numbers.

Even if you choose to hire a bookkeeper after learning these things, you have the language and skills to check in regularly and review where you’re sailing and where you’re off-track. This is so important and helpful!

#2: Perhaps you’ll decide you want to hold onto it!
You may happen to fall in LOVE with tracking, like I did. This may totally surprise you (as it did me), and you may continue your tracking practice for years to come, happily ever after.

Either way, taking time to dive right in clarifies what is so.

At the end of the day, you have 4 choices:

1. Stay unconscious and ignore this essential aspect of life. (Please don’t do that, dear friend, it’s so painful.)
2. Do it for yourself for a while. Learn. Start with beginner’s mind (which is super challenging as an adult, but also so rewarding).
3. Get a bookkeeper trainer to teach you and hold your hand. You can do it yourself without doing it alone.
4. Hand it over to a bookkeeper to do most of it for you, although still participate in some parts, especially the end-of-month review.

Flustered and confused? There’s help out there. If you want to work with my wonderful bookkeeper, you can find her here.

Your turn. Deep breath. Ask yourself:

• What is the right path for you, right now? Really and truly?
• Would it be helpful to learn this language, the systems, and a tracking tool?
• Do you imagine this being empowering?
• Can you sense that if you do your bookkeeping on your own for a period of time, that your awareness will increase in a significant and important way?
• Are you starting to kick and scream as you read this? How does it feel in your body, in your heart?
• Are you feeling hopeful, ready to take this on?

One more thing:

Life is a long time. (Hopefully). Your money relationship is a long-term commitment, and things are always evolving. We go through life changes, family changes, career changes — and so much that affects our money relationship. Your only lifelong commitment is to the practice (just like your self-care practice, or your spiritual practice, or anything else).

Remember: you can always change your mind. You can always shift, and try something new. Just head in the direction of clarity, peace, and empowerment — and you’ll do just fine.

Friendly reminder: Do a body check-in.

OK, I Want to Hire a Bookkeeper. Now What?

Oooooh, do I have a resource for you!

If you decide hiring a bookkeeper’s the way to go, here is a list of solid questions to bring with you. Hearing their answers will help clarify who you want to work with, and what exactly they will do for you.

16 Interview Questions for Bookkeepers:

1. Do you have advice/suggestions to give someone to help them decide if they are ready to hire a bookkeeper or do it themselves?
2. How long have you been doing this bookkeeping thing?
3. How did you start and what is your training?
4. What do you love about bookkeeping so much?
5. Do you prefer to do all of the bookkeeping for me? Or do you want me to jump in for parts?
6. Are you open to teaching me as well?
7. Are you good at explaining concepts that seem complex to me?
8. Do you think we’re a good match? What kind of clients do you like to work with?
9. Do you work with the creative community? Do you know how to speak our language?
10. Or do you work with attorneys, or …(name your particular field), as there are specific nuances to my accounting that are essential for you to know?
11. Do you offer bookkeeping for personal and business?
12. Do you offer virtual bookkeeping or at my home?
13. If you offer virtual bookkeeping, how do you get my info?
14. What are you favorite accounting programs? For personal finances? Biz finances?
15. Can you help me choose the best bookkeeping system for my needs?
16. What types of questions do you ask to help me choose the best system? (e.g. what features am I looking for? needs? preferences? etc)

Pause. Zoom Out.

If you can feel yourself beginning to contract or spin or check out out — please do not forget our trusty Body Check Ins! They’re so simple, yet so profoundly supportive.

Here’s a quick story from a student of mine who learned first hand how essential this piece is:

“When people are interviewing a bookkeeper they would benefit by doing a body check-in during the interview. The first bookkeeper I interviewed came very highly recommended. At the interview, I noticed something did not feel right. I reacted strongly to her way of speaking to me. I left the interview feeling anxious and agitated and unsettled. I over-rode my intuition and STILL offered her the work! Thankfully, she disappeared into thin air before we even got started. She never returned any of my phone calls after the interview. It was a blessing! Because I ended up with a fantastic bookkeeper. When I interviewed the 2nd bookkeeper, it felt right from the first moment. She “gets” me & my business, has a positive attitude, and was willing to educate me about Quicken and banking. This was my first lesson in following my intuition in my business decisions. You have to be able to work with the person….it’s an intimate business relationship and it has to be the right fit.”

Remember, there is no One Right Way to do your money relationship. There are many, many ways to forge a conscious money relationship. What’s important here is making a choice rooted in awareness and self-love. The goal is NOT to make “the perfect choice,” because there is no such thing.

You may make different bookkeeping choices for your personal, couple, or business finances — and you may choose to shift them down the line. All of this is good. The point is to stay awake as your money relationship evolves.

Every money decision you make reflects a whole world within you.

Fall in love with the process of working with your money healing, money practices, and money maps. Ask for support when you need it. Celebrate baby steps and love yourself whenever you get stuck. Add chocolate and beauty and shoulders shimmies as needed.

Related Resources
~ Is all this just too much to handle? What to do when you’re too terrified to even *peek* at your numbers.
~ Want to DIY your bookkeeping, but confused about what system to use? Here’s how to just pick one.
~ Want to do a (belated) End of Year Money Ritual? Here’s a guide, in two parts: Looking Back and Looking Forward.