What to Do if You Suck at Numbers, Receipts and Invoicing (Cheat Sheets Included) - Christine Kane

Did you tell yourself it’d be different this year?  Did you have big plans for keeping up with your books each and every month?  Like, did you write the word “FINANCES” into your Google calendar every other week in a moment of bravado?

Now that it’s September, here’s a question …

How’s that working out for you?

You got a little behind again, didn’t you? And by “a little,” you mean, “a lot.”  (Like, starting in February.)

That’s okay. I’m not one of those people who will tell you to work against your style and get better at being organized, or worse, learn how to do your numbers!  I’m not here to add to your pain. I’m here to relieve it.

ideal bookkeeper

  Your typical “passionate” start up business owner!

So, I’m betting you didn’t start your business because of your financial prowess. (As evidenced by the receipts jammed in your purse, the mileage log you forgot to keep, and those six invoices you never sent to clients.)

You started your business because of your ideas and your passion.

Problem is, as things get more successful, things also get more complex.  Which means invoices, receipts, P&L’s, Quickbooks, tracking and metrics.

And even if they aren’t that complex yet, you still don’t do this one thing you know you should do.

Well, here’s what you’re going to do to free up your energy, creativity and focus.

You’re going to hire a bookkeeper.

Here’s why.

A bookkeeper will not only relieve you of this energy-sucking duty, but a bookkeeper will remove this pattern of convincing yourself that you can save a few bucks by doing your own numbers. (And the illusion that it doesn’t take all that much of your time.)

Ideal bookkeeper

The common pattern among business owners: constant stress created by continually trying to do the things they simply stink at doing!


TRUTH:  You can spend your time learning a lot of organizing, track-your-numbers information. (Which takes time away from, you know, MAKING the money you’re trying to manage!)  Or you can get hands-on help.

Remember, you can’t scale your business unless you off-load the stuff that doesn’t create income.

So let’s make this simple.  Here are 5 non-negotiable steps to hire bookkeeper for your business.  (Please don’t glaze over and say “yeah yeah yeah.”  These guidelines (and cheat sheet!) will truly make this easy on you.)

Step #1: Require Experience with Solo Business Owners

This is non-negotiable.

As a solo-entrepreneur (artist, designer, coach or consultant), you’re a different breed. You run your own business. That means there are two critical factors you need from a bookkeeper:

  1. – Experience with solo businesses
  2. – The ability to explain financial concepts in everyday language.




Step 2: Get Clear on Technical Skills

Note: You, the owner, should not have to take a class or online training just so you can work with your new bookkeeper. 

The very reason you’re hiring this bookkeeper is because you want to avoid having to learn a new skillset and all the new software therein.  So, ask which programs s/he uses, and see if s/he can teach you how to use them as well.




Step 3: Require Trustworthiness

The most common question I get from clients when they’re considering a bookkeeper is about trust.  “How do I know this person isn’t a thief, or manipulative, or won’t share all my secrets with others?”

Well, start by taking a strategic approach in your vetting process:

✔️ Get at least 3 references (and call them!).

✔️ Get a list of the kinds of businesses they’ve served.

✔️ Get detailed information about their process of working with clients.*

*In other words, make sure they take their business seriously enough to have trustworthy systems. For example, if you ask how s/he receives payment, and s/he says something like, “Just pay me whenever,” that’s a red flag. You need a professional who uses systems, not someone who’s making it up as they go! (That’s what you do, remember? And you don’t want that same kind of chaos from someone who is trying to help you be more orderly.)


Step 4: Desired Personality Traits

Don’t hire a jerk.

Don’t hire someone who talks down to you or judges you.

And don’t hire someone who is too much like you. (No offense. But you suck at this stuff.)

Personality is the most important aspect of your bookkeeper so use the cheat sheet questions and look for red flags.




Step 5: Get Clear On their Services

A great bookkeeper doesn’t just keep your books. They can give you guidance and be kind of a financial coach as well.

Ask your bookkeeper:

  • Will s/he provide you with articles, books, or materials to help you learn?
  • What kind of coaching s/he does to help you understand your own finances?
  • Is she willing to check in on a more frequent basis at first so that you can get regular feedback or ask questions?

Okay my friend – you’re ready.  This will get you started. Now, go make this happen. You’ll thank me next year!

But for now, let’s have a bit of fun…

Share one embarrassing moment in your financial history that really proves just how bad you are at this job of tracking, systematizing and keeping up with your financials…

  • Thando


  • Monique Lusse

    Hey Christine, Love this article! Thanks for laying it out there clearly and in a straight-forward manner!

  • Annice Brown

    Love love love this article. I am a small business consultant and I hear this all the time. With your permission, I’d love to send my clients your article with total credit to you. In fact, I’d like to save it to share often.

    In return, I’d like to share a book ( I dind’t write it) I recommend o my young entrepreneurs regarding finance. It’s a book that resonated with me years ago and they keep updating. Don’t get turned off by the cheesy title: On My Two Feet (a modern girl’s guide to personal fiance). My clients love it.

  • Marilyn Watson

    One year ( MANY years ago ) I didn’t file my income tax because I thought
    ” I don’t owe them anything, so it’s all good”
    Boy friend at the time, a small business owner, said, “Oh great! I get to visit my new
    girlfriend in prison.”
    Never did that againLOL

  • Laura Rothenburg

    Well after having an amazing accountant way before starting my business, then when he retired although he recommended someone very good I never seem to really think of it being important keeping the books. I did speak to the lady but due to my laziness and not controlling my own finances i never got back to her. Anyhow, I do have all receipts from any adventures I take up, usually putting them into yearly envelops then forgetting about them until now that I have actually started a business although slow due to my lack of knowledge on marketing but learning and trying to get my head around it all. So embarrassing probably now is I am having to declare everything to HMRC but did get a friend to put a lot of stuff onto excel for me and although it is slow on my account as doing it my self but I am learning lots. So as I am with BNI I will use the accountant we have in the chapter making an appointment with her next week.
    So my question is, there are lots of packages on the market like Zero, Quick books by having a book keeper does this cut out using them even if I am putting everything down myself. Little confused to say the least or do I need everything trying to cut corners and cash going out.
    Have to say I really enjoy your topics you talk about even if I am in England.

  • Kimberly Stritz

    I tried to do my own taxes last year with my current business and boy was that a mess. I couldn’t find anything and I wasn’t clear on what I needed to do this. I just managed through it praying I got everything correct. Will probably use my new bookkeeper as soon as I hire them to get me straight on everything. I also didn’t track mileage and this caused me to not be able write off mileage and that sucks since my current business relies on me traveling to my clients homes for parties.

  • Michele Barard

    Embarrassing moment – I’d agreed to create and host a website for one of my authors, which was the beginning of me experimenting with creating sources of recurring revenue. The problem was I kept forgetting to invoice him because I didn’t have an automatic billing system set up. So I’d wait months and realize I hadn’t invoiced him and I had go back months to see when was the last time I’d ivoiced him and how much he owed. It was ridiculous and took me twice as long as it did to finally set up the automatic annual invoicing.

    • Christine Kane

      Michele – Yes, I have heard similar tales from so many entrepreneurs! Consider that time you spent, and add up the hours and what kind of income you could’ve created in that same period of time if you were doing the thing that makes you money – and suddenly a bookkeeper becomes a no-brainer!

  • Selma Harwell

    Taking a whole course for weeks …videos, assignments, exercises to set things up and learning how to do it and then never doing it again once the class is done. By the next time I look at it- I’ve forgotten all of it😲

    • Christine Kane

      Selma – That’s called being a quickstart. And it’s not unusual for creatives and entrepreneurs. 🙂

  • Mary

    Thanks for making me think about this a little bit more, Christine.
    So, for the embarrassing moments, I’ve had a few. I have a great guy that does my taxes but I’ve always believed I couldn’t afford to hire him to be my actual book keeper. I think he would love it because it would make his job a lot easier. The truth is I’m actually a bit embarrassed about the way I manage my money over all and I’m not sure I really want him to know that much. I’d rather just give him them the totals at the end of the year. But you’re right, it’s not really working for me.
    As to the embarrassing incident that comes to mind it is happening now. After ending last month thinking, “Hey, I’ve got $1000 extra to stash into the security fund”, I discovered that the electric bill for my business , which has a threshold of $700 on the auto pay ( so I can control my finances lol) went over $700 two months in a row. ( don’t you just love California?) Somehow, I missed all the emails telling me that I needed to pay the electric bill and suddenly I have an $1800 electric bill that more than swallows up that extra stash.
    I’m not sure if a bookkeeper would solve this problem but clearly I need a better system. You have motivated me to talk to my guy about what he would charge to be my bookkeeper.

    • Christine Kane

      What a great awareness to have, Mary! And yes! Talk to him and be open about feeling embarrassed. This is why each of us is SUPPOSED to have a superpower. Yours isn’t details, tracking or finances. So what? Your “guy” can’t do all the amazing other shit that you rock at!

  • Jodi

    I’ve found a CPA who helped me work out a system that now takes me 2-3 hours every Friday. I’ve offloaded to her the categorizing of expenses for the LLC rental properties and to balance out the accounts each quarter. Yay! That was so yucky and took me hours to do just one month. One of these days I’d like to delegate the things I do those few hours on Friday, but I can’t let go yet!

  • Christi

    As a CPA who works with lots of solo-preneurs I have finally figured out a system they can use…. and love….. print – color – scan. Done. Christine is right….the entrepreneur is not like any other creature and they need a super simple system to support their success! http://Www.ChristiBenderCPA.com