Should you hire a bookkeeper or DIY? My best stories + advice.

written by Bari Tessler June 28, 2018

So there you are, trucking along with your new, un-shaming, conscious and compassionate money practice, when — bam! — you hit a big, nasty snag.

(Or maybe it feels like a bog of muddy confusion, to you. Or an impossible riddle, which you have to solve before you can move forward — except you can’t solve it.)

To hire a bookkeeper … or not to hire a bookkeeper?

It might sound like a detail, but let me tell you: this is one of the most common quicksand traps I find people getting stuck in, towards the beginning of a money practice.

This question can even arise years into your conscious money practice, as you’re thinking about how things have shifted for you and whether expanding or shifting your financial support team is a good move for you, right now.

This question can feel confusing. For sure. But you can find your own answer to it.

Please know: this is an incredibly personal decision. There is no One Right Answer!

There’s a lot to take into account, here: how much money you have coming in and out, how complex your financial situation is, what phase of life you’re in, what your goals are, if you want to take care of your own books or not, and on and on.

Like all things money-related, the the very best decision is the one YOU feel most comfortable with.

So in this guide, you won’t find me preaching hard ‘n fast rules. Instead, you’ll find a ton of great support to help YOU make the best decision for YOU. But first …

Remember: this decision has an emotional side, too.

Did you forget this, in your rush to deal with the practical side and making “the right decision” and all there is to learn and do?

If so, that’s so understandable. Most of us were never taught to deal with our emotions around money — or even to acknowledge that money is emotional, too!

But ignoring our emotions rarely works. (In money matters … or anywhere else in life!)

While you’re caught up in the externals and mental chatter and nuts ‘n bolts of this decision, meanwhile within you, there might be a whole maelstrom of emotions and money stories and fear and feelings, getting triggered or surreptitiously running the show or making you feel numb or stuck.

You might have some feelings that need to be felt, here. Maybe a 5-minute journaling sesh is in order. Or, it might be even simpler than that.

Simply reminding yourself of this emotional context can help it relax.

My fave tool for situations like this? The Body Check-In. It only has to take a minute — and it can be such a trusty ally for moving through emotional muck.

So. Deep breath. Light a candle and whip out the dark chocolate, if you need ‘em. Now … onwards!

Confession: I used to be a Die Hard DIY-er.

Back in the day, I was on a mission to make sure everyone did their own bookkeeping. I’m a little embarrassed to admit this now, but back then, I never suggested people work with a bookkeeper.

I was convinced that everyone needed to empower themselves by getting honest, facing their numbers directly, learning the language and systems of money … and that this needed to include doing their own bookkeeping.

(With chocolate and shoulder shimmies and dance breaks, of course.)

While I’ve definitely softened my approach now, it’s understandable why I used to feel this way. After all: learning to do my own bookkeeping (and making it a conscious, compassionate practice) was massively healing and important in my own money journey.

See, up ‘til my late 20’s, I thought money was far too boring and mundane for a full-on creative, African dancer, authentic movement, psychotherapist-in-training gal like me.

I’d get bank statements in the mail and toss them, unopened, in the recycling. (“What does one do with such a thing???” I thought.)

This was the perfect metaphor for my relationship with money, back then. And my utter lack of consciousness and respect for it.

Money and I didn’t have a bad relationship, back then. We didn’t have a relationship, at all.

Plus, my old story of “I’m not good at math” somehow convinced me I couldn’t be good at money … and all this (along with money baggage from my middle class upbringing and lineage and on and on) kept my head buried firmly in the sand, when it came to money.

One fateful day, a dear soul taught me Quicken and QuickBooks.

(The gold standard bookkeeping software.)

It felt like the heavens parted … and lo and behold, that other side of my brain — the one in charge of money and numbers and spreadsheets — was there and worked!

“Excited” would be an understatement. I was shocked and delighted. For the first time in my life, I felt empowered and confident with a money system. What??

Quickly, I could sense there was more going on here than simple number crunching. As a creative-sensitive gal, I could FEEL it. The power money might have, not just as an external, material thing, but as a tentative bridge: between heaven and earth, sacredness and groundedness, deep meaning and action-in-the-world.

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 in somatic psychology … but I knew I was onto something essential. I trusted my heart and trusted I was on a stepping stone to my real work.

I jumped tracks in my career. I learned everything I could about bookkeeping and tracking systems. And I hung up my shingle as a bookkeeper.

Here’s what fascinated me most, at first. When prospective clients found me, they rarely even asked to see my credentials or qualifications. They skipped straight to, “OMG HERE TAKE MY BOOKS AND DO THEM PLLLLLLEASE I DON’T WANT ANYTHING TO DO WITH THIS!” They were desperate and grateful to hand off that hot-hot potato and never have to look at it ever ever again, EVAR.

For the next few years, I did bookkeeping for people and learned a ton. I honed my practical skills around bookkeeping and empowered myself with the language and systems of money. But I also learned about just how emotional and loaded this money stuff is, for all of us.

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 finally learned:

Hiring a bookkeeping can actually be a huge leap of courage!

That’s right: even if you’re not doing all of your bookkeeping yourself.

Working with a bookkeeper isn’t always about avoidance. For many people, hiring a bookkeeping IS a way of attending to their money and becoming conscious of their numbers more than ever before. When done intentionally, this collaboration can be a huge opening into financial awareness and healing.

For me? I did my own bookkeeping (on QuickBooks) for 12 years. I learned all the ins and outs of inputting in transactions, reconciling, pulling financial reports, and on and on. This was an invaluable education for me in so many ways.

Finally, a few years ago, it was time. My business had grown, my finances were complex enough, and I had so many other priorities … so I handed everything over to a great bookkeeper. (Her name is Jess Salzman, and she is amazing! You can find her here.)

So, take it from me. Both sides of this coin — doing your own books and entrusting them to a financial pro — can teach you tons.

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

So should you hire a bookkeeper or DIY? Here’s help deciding.

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

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

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 a story I hear all the time:

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 another story from our community:

I’m a creative, therapist type guy. I did some great foundational work in The Art of Money, and got turned on to Mint, 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. However, I do recommend doing your own bookkeeping, if only for a short 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. When you take the time to create this foundational intimacy with your money first, you’ll feel far more empowered (and less in the dark) if you do hand your books over to a pro.

Does doing your own bookkeeping give you the chills? Here are 3 helpful reframes.

If doing your own bookkeeping seems scary to you, you’re not alone: it does to many of us, at first! Here are three helpful reframes:

1.  It’s OK that you don’t already know how to do this.
Please, please un-shame yourself for not somehow, already, automagically knowing how to do your bookkeeping and use tracking software without anyone ever teaching you. That sounds crazy, right? But so many of us think this way!

It usually takes 6 – 12 months to feel totally comfortable using a bookkeeping system. There’s a learning curve, here, and it can feel steep. But that’s OK! Plus: you can consider hiring a bookkeeping trainer for some additional support. (Just make sure to find someone who’s not just a good bookkeeper, but also a good teacher — which is a skill unto itself.)

2. Make it meaningful adventure.
This really is possible! Bring in bright markers or rich incense or anything that helps this feel creative + playful, meaningful + fun — to you.

3. Remember; it’s not a lifelong sentence!
It’s just a short period of time to learn, experiment, and feel things out.

After you do your own bookkeeping for a while, you might choose to pass that puppy on over to a pro.

You’ll know you’re ready to pass your books off to a bookkeeper once you can:

  • Enter your income and expenses and comfortably navigate your software
  • Feel comfortable with basic bookkeeping language. For example: what a Chart of Accounts is and what the 5 main categories are (assets, liabilities, equity, income, and expenses); and what the names of your categories are.
  • Find and understand basic financial reports. For example: P&L (Profit & Loss), monthly income and expenses, this month vs. last year at this time.
  • Understand some patterns in your earning, spending, and cashflow

Once you grok these things, you’ll have the language and skills to check in with your bookkeeper regularly. You’ll be able to see (and really understand) for yourself when you’re on-track and off-track.

Plus, seeing (and really tracking) your cashflow patterns will also give you a solid foundation for making excellent money decisions in the short, medium, and long-term. While some people call this “budgeting,” I like to call it Money Mapping, because there’s so much that goes into this art. (More here.)

Quite simply, doing your own bookkeeping for a few months will give you the kind of intimacy with your numbers that, truly, nothing else can.

… Or you might surprise yourself and decide to keep doing your own bookkeeping!

You may fall in LOVE with tracking, like I did. This was a total surprise to me! But you may continue your tracking practice for years and years to come, happily ever after. Truly: it might shock you how many times I’ve heard folks in The Art of Money say things like, “Bari, OMG, I’m in LOVE with YNAB {or Mint or some other tracking tool}.”

Whether you choose to keep doing your own books for years or eventually pass them off to a bookkeeper, taking a few months to dive in and do them yourself will help you see clearly what it’s all about and whether you truly want to do it or not. (Plus, you’ll see that you actually CAN do it, which is incredibly empowering — even if you don’t keep doing it!)

At the end of the day, you have 3 choices:

1. Stay unconscious and keep your head shoved firmly in the sand around your finances. (Please don’t do that, dear friend, it’s so painful.)

2. Do your own bookkeeping, at least for a while. Learn. Start with beginner’s mind (which is super challenging as an adult, but also so rewarding). Remember: you can get a bookkeeping trainer to teach you and hold your hand! Doing it yourself doesn’t have to mean doing it alone.

3. Hire a bookkeeper to do most of it for you … but stay engaged in the essential parts, like end-of-month reviews.

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 of bookkeeping? The systems and skills of a tracking tool?
  • Can you imagine this being empowering?
  • Do you have the feeling that, if you did your own bookkeeping for awhile, you might become more aware in significant, important ways?
  • How does all of this feel? In your body and your heart?
  • Are you starting to kick and scream as you read this? Are you feeling hopeful and ready to take this on?

One more thing:

Life is a long time. (Hopefully). Your money relationship is a long-term commitment, and will follow you and grow and evolve right alongside you.

But your only lifelong commitment, here? Is to the practice. To staying engaged with the ups and downs and twists. You’re not committing to doing your own books forever (or to NOT doing them forever).

You will go through different life phases and transitions and career changes and family changes — so much that affects your money relationship and how to best nurture it.

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

When in doubt? Do a Body Check-In. (Ahhh.)

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.

That’s right: you’re allowed to ask questions before hiring a bookkeeper! And you don’t have to go with the first one you find. Hearing a potential bookkeeper’s answers to these questions will help you understand if you truly want to work with them — and it will give you clarity on exactly what 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 finances?
  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. Feel in.

If you can feel yourself beginning to get overwhelmed or contracted or checked-out — please remember your trusty Body Check-In!

It is so simple — yet so profoundly supportive. In fact, here’s a quick story from a student of mine about using Body Check-Ins when hiring a bookkeeper:

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 didn’t 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 money.

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

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.

You money decisions are practical, emotional, and even spiritual. Let yourself fall in love with the process, itself, of working with your money relationship.

Ask for support when you need it. Celebrate baby steps. Love yourself when you get stuck (especially when you get stuck). Add in dance breaks and deep breaths and beauty and homeopathic doses of dark chocolate as needed.

There is no perfect. There is only the process. Stay present to your process and you can’t go wrong.

Resources to go even deeper

~ If you want to work with my wonderful bookkeeper, Jess Salzman, you can find her here.
~ 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.
~ How do you make this feel fun + meaningful + creative? Here’s how to take yourself on a Money Date.
~ Want help deciding between a bookkeeper, bookkeeping trainer, accountant, and other members of your financial support team? Bookkeepers and Accountants and Money Coaches, Oh My!

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