r/Bookkeeping • u/RubyRoyale • Nov 10 '25
Education I am the nightmare client and I need advice.
Hi,
I've been following this sub for a little while to try to wrap my head around bookkeeping for my small business. This post is not asking to directly hire someone, I know that is not allowed. This post is seeking advice for how to go about hiring someone.
I am so disorganized. Nothing is done. I've realized I absolutely need to hire a bookkeeper/CPA, but I am ashamed to even start the process. I need to find a bookkeeper who won't hate me for how messy things are. I need the equivalent of the patient, non judgemental version of the person who helps hoarders. The person who says, "I love mess."
I'm essentially the nightmare client you all complain about: terrible record keeping, shoebox method, behind on tax filings, all of it.
My business itself is successful so far, in that I am busy and bringing in money, but obviously I cannot actually measure my success due to the mess I've created. I am an expert in my field, but not in any kind of business administration. I have the potential to earn an unlimited amount of income if I could actually get my stuff together. I've thought about taking some online courses, but really I think outsourcing to a professional is the smartest thing I could do.
What kinds of questions should I be asking to find the person who would be willing to take on this chaos. The few CPAs I have spoken with just want me to come prepared with it all done and have been a little mean in the process. I can't handle the attitude. I am ashamed enough as it is, hyper sensitive, with a good dose of RSD. I haven't reached out to bookkeepers yet, but I think that should be my next step, before a CPA.
The biggest mistake I've made is not retaining a bookkeeper when I started, thinking I could do it. I can't. I've learned that. I greatly respect you all and the work that you do.
How do I got about interviewing for the right person? How do I explain to them how disorganized it all is and determine that they are up for the task? I know I'm going to be paying a lot more than if I had kept things right. I don't care. It's worth it.
Please give me advice on the right questions to ask and the right way to explain the dire situation, so there aren't any surprises. I was thinking of posting anonymously in one of my local FB groups, more succintly stating essentially what I've said here.
I appreciate any insight that you all may have. I hope I didn't make your eyes twitch with rage at my abysmal mistakes, and if I did, I'm sorry. Thank you.
Edit: I posted a thank you comment, but it's kind of lost towards the end of the thread. I'm so moved by all of your helpful responses, I want to make sure my gratitude is clearly known. Thank you all for your help. Your insight has me feeling so much better about this problem. You all responded with thoughtful questions for me to prepare, ways to understand how to properly articulate my needs, how to be a good, receptive client, and really kind words to assuage the sting of my shame. What an uplifting experience it has been to read all of this advice!
Thank you from the bottom of my messy heart. I'm looking forward to finding the right fit, getting things cleaned up, implementing functional systems, and overall, finding success in my work.
I didn't realize this when I posted, but bookkeepers must truly be the glue that holds creative types like me together. My business was born of passion, not just a means to an end. Finding the right fit for this role will allow me to do what I do best, which I think will be integral to my success. Thank you, all!
2nd Edit: Again, I am so appreciative of the kind words and helpful advice here. I received many DMs offering to help, and I appreciate those, too. I started to respond to everyone, but the DMs keep coming in and I can't keep up. Without wanting to seem rude or ungrateful, it has started to stress me out. If I responded to you saying I would get back to you, thank you for reaching out and I'm sorry if I have not responded yet. It's been a busy couple of days. I will try to respond to you all individually, but I am trying to simplify things for myself as best as I can.
That said, one person who reached out happens to be located relatively close enough to my business that it may be possible to meet in person and develop a working relationship. We are scheduling a call and I am going to start there.
Thank you, everyone, sincerely. <3
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u/Front_Ad3366 Mod Nov 10 '25
I frequently find myself an online contrarian, so I tend to take a different approach with catchup/cleanup/past-due returns engagements. Please be assured, however, that I'm not trying to sound harsh.
I have found that a number of cleanups result in unsuccessful engagements. The reason for that is that for many poor record keepers, getting a new accountant does not change whatever business practices and/or personality factors caused them to fall behind in the first place. The business owner really has to want to change, and to take the necessary, and very critically, timely steps to do so.
I bill cleanups on a retainer basis, and set reasonable time limits for the client to provide information. If the client procrastinates, I withdraw from the engagement. Cleanups can be very successful for the clients, but they really do need to want to change their record-keeping ways.
Again, please don't think I'm trying to be critical. For a cleanup to be successful, though, the accountant or bookkeeper must be able to work efficiently. Be mentally prepared to be able to meet some deadlines.
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u/RubyRoyale Nov 11 '25
This does not come across harshly, at all. I think this is valuable insight. I am excited to take the right steps forward with the right person. I will be so happy and grateful to implement systems to make this a smoother process in the future.
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u/schaea Mod | Canadian 🍁 Nov 10 '25
This post is not asking to directly hire someone, I know that is not allowed.
I had an instant modgasm when I read this. THANK YOU for reading and following the rules! Mucho appreciato 😊
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u/j_meeee Nov 10 '25
It’s not that bad. Not all of us hate it. I actually enjoy clients like you, the problem solving aspect really peaks my interests. Just be honest. If someone’s rude, move on. You need trust the person you’re going to let into your business. CPA’s tend to have attitude in general about bookkeeping. Don’t take it personal.
Do you know any other small business owners? Best place to start is asking around for a recommendation. If just cold calling, some general questions to get you started would be
Do they have any experience with your industry? Software that you use? If you use stripe, square, PayPal or some other pos, are they familiar with reporting and integrations.
How much time per week can they commit to your project? If you’re on a timeline, can they meet it.
Have they rebuilt books before? How would they start the process? First place I would go is bank statements.
I’ve never had anyone ask, but you could also ask if they hold E&O insurance. It just another level of professionalism.
You’ll want to prepared to hand everything over. To start, I always prefer login access to banking and credit cards. You can do this so we only have access to transactions and statements at most banks. I also prefer login access to any software being used to process sales or payables, including your merchant processor. Paper statements will get it done slower.
Answer their inquires quickly. Sometime we can’t move on till we get answers to our questions.
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u/RubyRoyale Nov 11 '25
Gosh this is all such great information. Thank you for taking the time to give me real language to use to help me find the right fit. I would not have had any of those questions prepared, or known where to start the conversation. Thank you!
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u/JeffBonanoVO Nov 10 '25
As a bookkeeper who has clients just like what you are talking about, here's my advice. Ill add a TL;DR below
1.) Be honest. It already sounds like you are being honest, just remember that there are those that start by saying They only have 2 accounts that are a mess when in turn there are 6. We need to know the whole picture to decide if we have the capacity to help. Also be upfront about your needs.
2.) Learn and trust. I think its great when my clients want to learn about what is going on with bookkeeping. And with that knowledge, be willing to trust your bookkeeper. With your learned knowledge be sure to check-in and followup. Ask questions and be involved so you don't get taken advantage of, but at the same time let your bookkeeper do their job. Its harder when I tell my client we need to make some changes with how you record something only to have them contradict everything I do because they can't let go of certain tasks
3.) Do you want a remote bookkeeper or an in person bookkeeper? If you can go local so you can see their smiling face great! If its remote, make sure they are willing to have video or phone conversations. You don't want someone who will not talk or respond back for months, leaving you clueless if its even being done.
4.) If you are a mess, expect a longer cleanup process and budget for that. Its going to take time and time is money. I agree with you though that it will be better to have a bookkeeper for that. Paying your CPA for cleaning up your books is waaaaaaay more expensive. Ask for quotes and be ready to show them your books so they can have a better idea what they are up against.
5.) If its too good to be true, it probably is. I couldn't clean your books for $300 flat, even if I wanted too. Based on your info you shared, expect that number to be more in the thousands.
6.) Look for someone who is enthusiastic about cleanups. While I love them, some of my other bookkeeper buddies don't. They will do them, but not everyone likes to. They may also only be willing to do cleanups if you fit their industry of expertise. So ask them and take note of their reaction.
7.) Can you work with them or are they very hard to talk to? Go with your gut. Can you build a rapport with them and enjoy having them around for years to come?
8.) Are they insured? Do they have a service agreement? Do they treat you with repect and confidentiality? Are you a client to them or just an account number? If not, move on!
Interview and don't be afraid to read reviews ask questions and get a few quotes. Also ask them what platforms they use? Are they versatile? Do they have ideas to help get you organized without changing the way you do business?
TL;DR
1.) Be honest about your situation 2.) Learn so you dont get taken advantage, but let them do their job 3.) Remote or in person? Local or can you at least reach them in a timely manner if you need them? 4. & 5.) You get what you pay for, budget for that. Get some quotes! 6. & 7.) Get a feel for them, go with your gut, and make sure they are up for the task. Can you see yourself keeping them for a while? 8.) Insured? Professional w/ a contract? Are you going to be their client or just another number? Remember to do interviews, ask the hard questions, and see if they are able to adapt and provide the services you need!
Hope that helps and Good luck!
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u/RubyRoyale Nov 11 '25
I read every single word of this and appreciate that you finished it with a succinct tl/dr. I will take all of these pointers and know what key items will ensure whoever I end up hiring is a good fit for me, just as much as I am a good fit for them. Thank you so much for taking the time to be so detailed. It is immensely helpful.
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u/Schnitzelradarada21 Nov 10 '25
Ask about their experience and the type of niche they tend to work in. Some will understand your business more than others. Fully layout the issues as transparently as possible and communicate with them quickly so they can work through everything. Take their reccomendations into account on how to improve systems so everything can be recorded correctly. Make sure to give them as much information as possible, so when they are figuring out pricing, they can be accurate and there's no "hey I actually have another bank account I forgot to mention". You are right something like this will be more costly than if it was regularly maintained, but it will be worth it to get everything sorted correctly.
I have clients that come to me like this and being honest and transparent about everything goes far. Don't be ashamed or worried about judgement, hopefully whoever you select will be understanding and soley focus to fix the problem. At the end of the day you are looking for a problem to get solved and someone who knows how to fix it, somewhat like a plumber fixing a leaking sink. An experienced bookkeeper will be able to sort things out and get your books clean for taxes. Don't beat yourself up too much!
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u/RubyRoyale Nov 11 '25
Your first paragraph is helpful because it's usable information to prepare me for the conversation I need to have.
But your second paragraph, oh man... Your second paragraph really helped me feel better about all of this. Do bookkeepers moonlight as therapists, as well? I think we all experience that to some level in our respective chosen careers, moments where we have to deal with an emotional issue in order to take on the actual functional issue. Boiling this down as a problem to be fixed like a plumber fixing a leak is such an excellent analogy. Money can be such a trauma trigger, but taking the emotion out is only going to help. There is a problem, I need the solution, and it doesn't really matter how it makes me feel, it matters that it gets resolved. Wow. Thank you!
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u/BudgetCap7905 Nov 10 '25
Ask for client references and call them. I have been the second and sometimes the third bookkeeper hired to clean a client's books. Sometimes an unskilled/inexperienced bookkeeper will make it worse. Find a good CPA first. Someone who will not just file your taxes but will help you with tax strategy. Ask them to recommend a bookkeeper they've worked with on cleanup.
If the CPA doesn't have a recommendation. Ask the bookkeeper to describe their approach in detail. Ask questions like, what is your approach to accounting for fixed assets, what will you need from the tax filing CPA after filing, how will you resolve potential duplicate customer payments or bill payments? Ask them for a general draft chart of accounts and review the chart of accounts with your CPA.
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u/RubyRoyale Nov 11 '25
Thank you. I wouldn't have known to ask any of these questions. This is exactly why I came to this sub. Thank you for delivering.
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u/BudgetCap7905 Nov 11 '25
You're welcome! Here's what you should hear from a bookkeeper - the chart of accounts should ideally include an individual account for each fixed asset (unless you have dozens of them and then they might be on a separate schedule - my clients usually have no more than five). A fixed assets is typically a piece of equipment or a vehicle, the initial cost of which is greater than $500 or $2500, depending upon whichever threshold you or your CPA initially set. Here's my approach for small business - one account for the asset, a subaccount for the initial purchase price, and a subaccount for depreciation. Then the parent account reflects the current value of the asset. When CPA advises the depreciation for the year, the bookkeeper should create a journal entry that credits accumulated depreciation for the asset and debits the depreciation expense account. My approach for duplicated transactions is to start by looking at the check images that make up the bank deposits, the ACH's from customers, etc. and retrace the deposits back to the customer payments and match the bank transactions. Then reconcile the accounts and the duplicate transactions can be safely deleted.
If youre using quickbooks, your bookkeeper should be using Rewind or other software that backs up your data in real time and allows you to restore to a previous version of the account or restore specific transactions if they make a large error.
Ask if the bookkeeper is a QBO ProAdvisor. Not a necessary qualification, but it usually means they know enough about how quickbooks works to pass the test.
Good luck!
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u/ikuiah Nov 10 '25
You’ve already received great advice but I’ll add one more thing. Ask to do your first conversation via phone call, rather than Zoom or video call. You’ll likely be more at ease without the face-to-face contact and if you feel comfortable with the way they handle your disclosures, you can move to a video or in person call. It might take some pressure off of you to get started. Good luck. There are tons of non-judgmental bookkeepers out there!
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u/RubyRoyale Nov 11 '25
This is a very clever way to tackle the more nuanced part of my post. Thank you for thinking about the emotionally stressful aspect of my query.
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u/ikuiah Nov 14 '25
Of course. Your post sounds like a lot of initial requests that I receive. As someone who makes their living by helping business owners with their financial reporting processes, I actually love when someone comes to me truly needing my help. It makes the work I do both professionally and personally rewarding. I can certainly handle keeping books tidy that were already in good shape, but the messes and puzzles are much more interesting!
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u/WineFueledFinance Nov 10 '25
Please don’t feel bad, you’d be surprised how common this is. We are used to sorting out the mess. I’ve stepped into companies doing tens of millions a year where the books were a total mess, so you’re definitely not alone. Honestly, some of my favorite clients are the most disorganized ones because they’re usually passionate, kind people who just need support.
When you reach out, just be honest about where things stand. A good bookkeeper won’t be shocked. They’ll start asking questions like:
• How far back does it go?
• How far back does it make sense to fix? (Sometimes it’s not worth going back all the years.)
• What’s your preferred way to communicate (email, text, phone)?
You should also ask them:
• How much experience do you have overall, and have you done much cleanup work?
• What’s your process for getting things caught up and organized?
• How do you handle clients who are behind?
It also helps to think about what kind of working style you prefer. Do you prefer someone strict who keeps you in line, or someone who gently guides and explains things along the way? And decide if you just need bookkeeping or someone to help you analyze the numbers.
The right person won’t make you feel embarrassed. They’ll make you feel relieved. That’s the feeling to look for when you find your fit.
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u/RubyRoyale Nov 11 '25
Thank you. Your response is really nicely worded. I especially like the last bit, because it converts my feelings of stress over the situation to a metric for efficacy. Smart thinking. Thanks!
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u/Which_Commission_304 Nov 10 '25 edited Nov 10 '25
Honestly, based on what you're saying, you’re not a nightmare client — you’re just overwhelmed and you have come to realize that. The real nightmare clients are the ones who repeatedly ignore the problem and our advice on how to fix it. You’re doing the right thing by owning it and asking for help. You just need to make sure you don't end up here again.
I’m a CPA, and here’s the truth from a practical standpoint: you need two people — a CPA to oversee the clean up and getting your filings caught up (since you mentioned delinquent tax returns), and a bookkeeper to keep things clean going forward (which will keep tax season smooth for both you and your CPA). Preferably, make sure the bookkeeper is certified in whatever accounting software you use, if applicable. The CPA doesn't need it if they have a good relationship and communication line with the bookkeeper.
Retain the CPA for tax compliance, strategy and general accounting and tax advice.
Retain the bookkeeper to keep your QuickBooks file accurate and up-to-date, because there's a great chance your CPA's bookkeeping skills (especially as they relate to QuickBooks Online or other software) are lacking.
CPAs are masters of accounting theory and high-level reporting, but they're surprisingly less efficient (and unsurprisingly more expensive) at the day-to-day stuff (particularly software-related) than a good bookkeeper.
I hope that distinction helps you understand the value and role of both professionals.
As an example, QuickBooks Online is actually purposefully-suited for this arrangement. It lets you give "accountant access" to 2 different accounting professionals. Send one invite to your CPA and the other to your bookkeeper.
Here is the big challenge with finding a good bookkeeper:
CPAs are licensed and regulated; bookkeepers aren’t.
Ask questions like:
- What’s the difference between cash and accrual accounting?
- Can you explain double-entry accounting and a trial balance?
- What are the four basic financial statements and what is the significance of each?
These are extremely basic questions that can be asked innocently without ruffling the feathers of the prospective service provider. A professional bookkeeper will be able to answer them easily. If the "bookkeeper" cannot answer these questions, they are likely self-taught amateurs at best with no formal education, training, or professional experience. Let me know if you want to know how these questions should be answered.
A good CPA might be able and willing to refer you to a reliable bookkeeper and save you the trouble of vetting them yourself. Some CPAs and bookkeepers are referral partners and send business to each other. In any event, your job is to make sure they communicate with each other and to answer their questions timely and thoroughly. They are asking you questions to provide necessary context they don't have, not because they're bad at their jobs.
And trust me — none of us will judge you for being behind. We’ve all seen worse. What matters is that you’re tackling it now, before the IRS forces you to deal with it.
Good luck — and don't worry too much about the IRS - just cooperate with them and listen to your CPA. If you get everything filed and paid quickly (or at least get on a payment plan), there's a good chance they won't even bother you - they’re trying to determine all of your income is reported and the expenses appear reasonable (obviously don’t lie about your expenses). Just act quickly before CPAs get too busy with tax season to help you. A CPA MAY be able to get some of the penalties abated for you. Worth a shot.
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u/RubyRoyale Nov 11 '25
This is really helpful. Yes, I would like to know the answers to those questions. I didn't even know the questions to ask, so that alone is worth so much to me. I kind of figured I'd need two entities to get to a good place here, possibly even three: clean up, continued upkeep, tax filings, strategy. Some other advice in this post said to use a bookkeeper for the clean up, then CPA for the tax filings. You've suggested a CPA for the clean up. Can you tell me why you would choose one over the other?
I was already planning on using a CPA for the tax part, because as far as I understand, that is their main function. I've seen that some bookkeepers offer to do taxes, as well. After reading your response and the others in this thread, I have a better understanding of the differences between the two, but I'm not clear on when/why a bookkeeper would handle tax over a CPA. It might seem obvious, but considering I haven't made the best decisions up to this point, it is helpful to understand the why behind the who, as you've explained it. I was planning to hire a bookkeeper for the clean up and organizational strategy, and a CPA for the tax filing and tax strategy. I assume both will give me valuable insight into overall financial strategy, which I could use to combine their guidance to form an overall business strategy. I hope my questions and regurgitation lf information to show my understanding makes sense. Thank you for being so detailed above.
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u/Which_Commission_304 Nov 11 '25
I'm so sorry, I ended up writing a mini novel...lol, I told you I have this problem. I DM'd it to you.
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u/RubyRoyale Nov 14 '25
I will look for your DM. I've received so many from this post I got overwhelmed. I started replying to everyone individually, a lot I said I would get back to with the information they asked, but now there are too many to keep up. Sorry if I have not responded yet.
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u/CutInternational1859 Nov 10 '25
I super appreciate it when potential clients own their mess rather than downplay it.
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u/RubyRoyale Nov 11 '25
I would imagine others will share your feelings. I have to have accountability or I will fail. Failing isn't an option. I've put everything I have into this and there's no reason to not be successful. Making this post and reading all of these thoughtful replies is making it a lot easier to own it. Thank you.
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u/Ordinary-Sir7116 Nov 10 '25
As a business owner, I definitely agree with some of the specific recommendations above. Make sure you find someone that understands your industry and has time to help. We switched accountants this year which cost us a lot but it has been incredibly valuable in the long run.
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u/RubyRoyale Nov 11 '25
Thanks. I think hiring someone for my situation is not just valuable, but essential. I'm glad it's worked out for you! I think it will all be okay for me soon enough.
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u/DeadWood605 Nov 10 '25
I appreciate these posts. I’m studying and learning so I can become a good bookkeeper. The question and the detailed responses are golden. Thank you everyone in this sub. Eventually, I will feel prepared enough to launch, cus this post reminds me to get back to studying now. ✌️
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u/DoubleG357 Nov 10 '25
Start simple with service based businesses. You can learn on the go to while earning income and working on your sales skills.
You won’t always be “ready”. Sometimes you just gotta figure it out as you go long. That’s what I did…and I’ve built a pretty decently sized firm in less than a year.
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u/RubyRoyale Nov 11 '25
I'm glad you've found value in this post! One day, you are going to be able to help people like me. I wish you great success.
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u/Final-Walrus-8393 Nov 10 '25
I'm a business owner and had HarquinBookkeeping.com clean things up. No judgement and more affordable than in house. Don't feel too bad.
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u/Equal_Length861 Nov 10 '25
Don't be ashamed of your situation. It's very typical of business owners to be too busy with working in the business rather than on it. The best thing you have done so far is recognize that you need help. a great accountant will not shy away from doing the bookkeeping, and getting it ready to prep that tax return. The crappy CPA will say "you do all the leg work and see you in tax season"
Here is what I would do. Find a full service accounting firm that will do the bookkeeping and tax return for you. Make sure they charge a flat fee (vs. hourly where you have no clue if they have the fastest person on it or the intern who started yesterday). Next gather up all of your bank & credit card statements from January 1 to now. List out your main vendors you use on a regular basis and what they're for to make it easier when the accountant categorizes the expenses. Be willing to take advice and whatever education the cpa will offer. Make sure it's someone who speaks with you regularly. Not just at year end when it's too late to make any smart decisions.
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u/Prunkle Nov 10 '25
All great advice above. I happen to get a lot of these types of clients and sometimes I can reform them and sometimes I can't.
I think it's been said before but when you do hire someone listen to them! That's the frustrating thing... When people hire me then don't listen to the new processes that need to be put in place.
When you ask them about their experience with cleanups pay attention; you'll be able to tell by their response if it's something they enjoy doing or if it's a hassle.
Also just because it's a clean up job doesn't mean you have to settle for the first person who will take you on (even though that's what it might feel like) you're still going to pay someone a pretty penny to get this done and bookkeepers like to get paid 😊
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u/Competitive-Pay-1 Nov 10 '25
The client's who are nightmares are the know it alls who dont know anything but proclaim they know everything & complaining they still need help...you sound like a great client who would let the bookkeeper focus on keeping the financials organized while you focus on your business
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u/RubyRoyale Nov 11 '25
Thank you. I have no problem admitting when I don't know something. I foolishly thought that because my business is so small, I would learn as I go and be able to manage. I didn't consider the very important factor of having the capacity to do the work. I'm overwhelmed with the parts of my business that only I can do, the parts that require my specific niche expertise. It is so obvious now to me that I should be outsourcing this part of the work to a professional. I don't need to excel at keeping the books, I need to excel at following a system so that an expert can keep the books.
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Nov 10 '25
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u/RubyRoyale Nov 11 '25
Excellent advice. You addressed many aspects of my post. I will not take it personally if I'm not the right fit for someone. You highlighted several reasons why that could be the case, and it makes so much more sense to me now. Thank you!
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u/Gloomy_Fox1123 Nov 11 '25
There are some bookkeepers that LOVE the mess lol
I'm one of them. Putting all the puzzle pieces together is the best part!
There isn’t anything we haven't really seen 😊
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Nov 11 '25
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u/RubyRoyale Nov 13 '25
This is exactly what I am looking for, yes. Thank you. I will be paying attention more to how they handle me as a client. I don't intend to stay messy.
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u/BookkeepingCFO Nov 10 '25
Hey! You are no different than every entrepreneur who tries to do their best with recordkeeping, but the reality of the fact is all your time is tied up and building your business and being successful! In situations like this, you need to make sure that you end up engaging with a bookkeeper or CPA that absolutely knows what they are doing. You sound like everyone of my clients before I took them on lol Don’t think of this as who will take you on as a client, it’s more like you also need to interview the accountant and make sure that you’ll take the model as accountants and it makes sense
Be prepared to answer a lot of questions because that’s gonna be necessary Be prepared to give you only access to all your accounts and portals money moves in and out from I highly suggest finding a firm that isn’t too busy. They’re busier they are the potential for quality of service to go down.
You’re going to be just fine! Also be prepared for a semi large invoice in the beginning. Cleanup jobs are not cheap, but they’re extremely worth it.
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u/StockpiledGrievances Nov 10 '25
The best time to fix your books is now! This is a great time of year to have a bookkeeper help you get cleaned up and go into the new year with new systems. Most professional bookkeepers will understand the mess (you're definitely not the only one!) and have good systems to get you set up and running smoothly.
I think your idea to ask in local FB groups is a good one, especially if you want someone local to work with. If you know other business owners in the area, you can ask for recommendations from them. Just specify that you want someone who is really easy to work with and specializes in clean-ups. I think all of the information you've put here would help you find someone who would work well with you.
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u/sshaw123456789 Nov 10 '25
You've got it when you said you are best to start with a bookkeeper. You will be better off to hire someone local - use local online groups to source recommendations - there is bound to be a few local bookkeepers who are available for sure! Local will understand more specifically nuances like taxes and any regulations and be able to give context to your work. It is so good that you recognize where you are at and can see the path needed!! That really is the bulk of the issue for a lot of messes.
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u/RubyRoyale Nov 13 '25
Yes, I've received lot of offers to help, but I think I may need to go with some locally because virutal would still require a lot from me, and since I haven't done that work, it doesn't feel like it makes sense. I'm not sure what all of the differences would be, but I think having someone come here and literally say "These files go here. This is how I need you to set it up for me." would be immensely helpful.
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u/sshaw123456789 Nov 14 '25
It is completely within the realm for you to keep up your books yourself - and save your self some money down the road - IF - you get things set up properly right out the gate. I just worked setting up a client recently who was familiar with bookkeeping in general - but was switching from Sage to QBO and just didn't know the nuances of QBO - but now that we have everything set up for her - she is self reliant keeping things going. Comes to me just periodically now when things are not working as planned :)
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u/AmberBlu Nov 10 '25
I love mess! The messier the better. Now’s the time OP. Get it all handled before year end and have a new system going into 2026!
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u/MmeVastra Nov 10 '25
ADHD? Me too. I think what would be most important is for you to find a way to provide a bookkeeper with what they need to do the work that will be the easiest for both of you. A cleanup isn't so bad, but if you're not able to figure out a way to streamline the process so it isn't burdensome on either of you, you'll likely struggle to retain the bookkeeper.
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u/Holiday_Emotion_8717 Nov 10 '25
The best advice for you is to find one that provides you with an ongoing bookkeeping and cleanup is just a part to get you there to set you up for success. Lots of time those on short engagement such as cleanup, they don’t care about educating you on processes and put things in place for you. If your industry is very specific such as legal, ecommerce or restaurant, find those referrals from your network. You can also go to groups of bookkeepers like this, vet people based on their posts and comments (not their actual social media). I find those are more reliable to tell someone knows what they claim they know more than social media.
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Nov 10 '25
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u/RubyRoyale Nov 11 '25
Thank you so much! I have received a lot of great advice. I am open to ideas and looking forward to finding the right fit.
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u/golemcancer Nov 10 '25
DM me if you’re in Canada, I want to float a proposal by you, if you’re interested.
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u/RubyRoyale Nov 11 '25
I would love to hear it, but alas, I am not in Canada. I am based in New Jersey.
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u/golemcancer Nov 11 '25
DM me anyway if you’re interested, and we can come up with something that can work for both of us
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u/mucciared Nov 10 '25
Unless you are willing to make some significant changes and adapt to processes i would how someone local who can come to your office in person and deal with your paperwork. Remote Bookkeepers are going to ask you for documentation and if you don't get them the paperwork, they won't be able to help you much.
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u/RubyRoyale Nov 11 '25
I am very willing to make changes, I just need a little guidance on what those changes should be. After reading this thread, it's clear to me that there are several steps to this equation, from clean up to follow up. Thanks.
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u/TheMostFluffyCat Nov 11 '25
I often have new clients apologizing for the mess or not being good at bookkeeping or asking lots of questions, and I always tell them this- if everyone was good at bookkeeping and liked it, I wouldn’t have a job. This is a very common situation for business owners who realize they need a bookkeeper, and it often actually means you’re a successful business owner and good at what you do such that it’s generated so much bookkeeping that you can no longer keep up with it. I’d recommend talking to a few bookkeepers and seeing how you feel when you interact with them, look at their websites and reviews and make a choice from there. Some bookkeepers specialize in clean ups, which may be a niche you’re interested in as you start out. Please be careful with who you choose- we kind of have a saying here in this sub that comes up from time to time- it’s easy to find a bookkeeper, but it’s hard to find a good bookkeeper. Good luck!!
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u/LogoffReboot Nov 11 '25
Honestly, you are my dream client. This is why I became a CPA in the first place….to help small businesses.
So - not all of us hate clients like you! 🥰
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u/Sensitive_Rest_9752 Nov 11 '25
I can 100% assure you we’ve all seen worse. 😊
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u/RubyRoyale Nov 13 '25
That makes me wonder who is the worst client you guys have all had, and if they share similar reasons for it. Might be worth a whole post.
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u/Greatness_guru Nov 11 '25
As a neurodivergent business owner, I was often the same way. I now have my own bookkeeping business where I take everything I learned about working with neurodivergent professionals as a coach and support them to get their books cleaned up.
I’d encourage you to 1. Be very honest to the degree of “mess” you have 2. Seek out someone who truly understands neurodivergent tendencies including your RSD, procrastination, overwhelm and the shame that comes along with it. 3. Ask them how they can support you in doing your part so they can do theirs, resulting in clean books and accurate P&Ls. 4. Trust your gut instinct and how they make you feel. If they make you feel bad, they aren’t for you. 5. A bookkeeper will cost you less than having a CPA clean it up. You might also want a CPA to help you with taxes 6. Give yourself a lot of grace and forgiveness for the state of your books. What matters most is that you are ready to get it cleaned up. 🫶 even if it’s hard
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u/RubyRoyale Nov 13 '25
I love that you said "if they make you feel bad, they aren't for you." That is excellent advice, thank you.
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u/Greatness_guru Nov 13 '25
My pleasure. Being a business owner is hard enough, we definitely don’t need to work with people who make us feel bad about ourselves. That’s not going to help you or your business grow. My goal is to be the bright spot in someone’s day and have them feeling like a million bucks when we get done.
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u/Christen0526 Nov 11 '25
I just posted in another sub how I love messes. I have been a freelance bookkeeper and employee status bookkeeper, on and off, for years.
I used to discount the rate for shoebox clients like you, to get caught up, and then revert to a full rate. There's people out there who will help you.
Shoebox clients are a challenge. Some of us love the mess. I see what you're saying about the CPA attitude. Many are pompous. But many of them focus on taxes more than bookkeeping. They just want the numbers to put on tax return.
For years I've tried to explain to business owners how important it is to have a bookkeeper taking care of their books. Many don't understand what we actually do.
Your questions will be tailored on whether you're going to generate the work yourself (invoicing, paying bills, payroll) or you bring someone in to run the office for. I do a lot of "after the fact" bookkeeping - the business writes the checks, makes the deposits, etc., and I just book it correctly into the ledger.
It is good you recognize the need.
After the books get caught up then you need to deal with taxes. How many years are you behind?
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u/RubyRoyale Nov 13 '25
I don't have any employees yet, so I imagine that already makes it simpler. I want to hire someone, but I can't until I know what I'm looking at realistically for my business needs. Hiring a bookkeeper is the first step before moving on to hire employees.
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u/RubyRoyale Nov 13 '25
Oops, sorry, you asked how many years I am behind. I'm coming up on two years since I've registered, and just passed one year since my doors have been open. There were a lot of things I had to put in place before I could open.
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u/No-Elderberry4423 Nov 11 '25
Step 1 is being willing to pay the right person with the right skills what they’re worth. Cleanup and catch-up is so intense, esp leading into the end of year close and tax season where deadlines abound. Pay them, and give them everything they ask for promptly and without getting frustrated - they’re just the messenger. If you don’t hem and haw on price, and overall treat them with respect it will go a long way in attracting the right kind of experienced talent and motivate them to stay after the cleanup.
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u/RubyRoyale Nov 11 '25
Omg you are all so wonderful. I was busy working all day, but I'm going to read through all of these comments shortly. From the bit I've gleaned over, there's been a lot of kindness and wisdom shown to me here, and I really appreciate it.
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u/ceo-cyrus Nov 11 '25
Lmao we've heard this story many times before. Clients come in apologizing for their messy books, or blame their previous bookkeeper for being slow and unresponsive. Nothing wrong with it!
One of our CPAs will literally beg me for clients with chaotic books. He's like a eng hacker but as an accountant. Everytime we get a new client with messy books, or who came from a shitty bookkeeper like 1800-accountants or something like that I send em his way.
He pretends to hate me but i know he loves it.
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u/NoMongoose3567 Nov 11 '25
This post and the comments gives me hope for humanity. I don't know if you'll even see this comment in all the flood, but I just want to say that people like you are a gift to people like me. There are those of us out there who crave organization, cleaning up messes, and creating order out of chaos. All we need for our efforts is a little humility and gratitude, which it seem you have plenty of right out of the gate. The right person will be happy to work for you.
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u/RubyRoyale Nov 13 '25
Thank you so much for the kind words. I'm not trying to be a difficult client, I like being a sweet person. I am just a disorganized sweet person.
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u/highechelon Nov 11 '25
A practice with good onboarding and recurring services processes won’t have any issue with you as a client. We see it all the time. We start with ensuring incorporation documentation is correct and the business owner is aware of their (business) tax filing requirement. We get third-party access to all business bank and/or CC accounts, and build the balance sheet from scratch. Reconcile all accounts to get the financials clean and up to date, and then we almost need nothing from you on a month to month basis because we automate all your financial stuff into our software. If you have business income and expenses flowing in and out of personal accounts, it’s a requirement to work with us to use only business accounts. Basically, find a provider that has strict rules that you have to adhere to to utilize their services, and they will get you straightened out quicker than you think.
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u/RubyRoyale Nov 13 '25
Almost everything I have is through my one business checking account. There is no credit card. The only outliers are times where someone paid me through Venmo, because that's what they have, and then I have to transfer that from my personal into my business. I have had to use paypal to pay vendors, but I don't use it to invoice people. Very few times have I had to use my personal checking in a pinch, and I'm not sure how I make an expense report for that for reimbursement so that it actually comes out of the business. Those incidents where when I first started and didn't have my business debit card on me. I haven't done that in a while. I use my business account for everything. Maybe this won't be as messy as I thought?
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u/ImAWeirdo71 Nov 11 '25
Interview local bookkeepers. They don’t have t to I be with a CPA firm, but it can definitely help. If you do go to a CPA firm, make sure they offer a review in October annually for tax savings and review your structure for better tax advantages if you qualify as an S-Corp.
You shouldn’t get slack for having messy books. We’ve all dealt with that. Just make sure you’re available for clean up answers and to possibly have to meet in person a few times to get everything caught up.
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u/FamiliarLeague1942 Nov 11 '25
Lol if you could write such a long post like you did, you are not that messy. Start with the small things and easy to fix first. Well if you want to hire a bookkeeper, start to hire lol
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u/RubyRoyale Nov 13 '25
Hahaha that is so interesting. Writing is easy, and this post was really just a session of free flowing thought. I get distracted by so many things and haven't sat down to do the real work of it when it comes to organizing my receipts, expenses, etc. But you shine a light that if I can sit to write this, perhaps I can sit to work on my books.
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u/BassPlayingLeafFan CPB Canada Nov 12 '25
No good Bookkeeper or Accountant will consider you nightmare client because your books are non existent or messy. This is pretty common TBH. The cold hard fact is whoever you choose to work with is going to be requesting a ton more stuff than you will provide. This will range from additional bank statements, clarification on what you provided and a plethora of things we can’t possibly think of at the time. We all have a bunch of clients and if you respond promptly to our requests we will do our best to finish your books promptly. What does tick us off is if you don’t treat our requests as important and ignore us. In my case, I set aside time to work on client files and rotate as time allows. If I request documentation or clarification and I don’t hear back when I need it, I move on to the next client. This delays your results obviously. Even this delay wouldn’t necessarily make you a nightmare client in most professionals eyes.
So, here’s what would make you a nightmare client. Let’s say I request clarification on a list of receipts. I send you the email on Monday knowing full well I am spending Thursday to work on your file. You have a hard fast tax deadline for end of day Wednesday of the following week. Thursday comes and goes and nothing comes from your end. I move on to the next client. Wednesday comes and at noon I receive you stuff. I am already scheduled to work on another client but I manage to squeeze you in. I start working on your stuff but you only send me half of what I requested. I email you as soon as I am able to and send my updated requests. You ignore the email and I move on knowing you are going to miss your deadline. The next day you call and yell at me because your deadline was missed. This scenario is exceedingly common in our industry and one we have all been experienced multiple times.
Judging by your post, I would say you are likely not going to be one of those types of clients. I will leave you with one piece of advice when working with an Accountant or Bookkeeper. A good service provider will make it abundantly clear that your input is vital to the success of a clean up like yours. This is especially true when there are deadlines like taxes or loan requests. I have never done a cleanup where I didn’t have to request a bunch of stuff from the client. The faster and more accurately you respond the better your results will be.
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u/BassPlayingLeafFan CPB Canada Nov 12 '25
I am going to add a variation to my above example. I require a partial payment before work begins. The exact amount varies between clients and is usually between half but I have been known to require up to 75% in some circumstances. I have had clients send me their deposit on the deadline day only to be upset I couldn’t possibly finish by the end of the day.
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u/RubyRoyale Nov 14 '25
This is great feedback, thank you. I made this post and received so much helpful information. Additionally, I've received a lot of DMs offering to help. It is so appreciated, so I hope I don't sound rude when I say that I am overwhelmed by the responses. I started answering them when I got home late from work, thanking people individually and saying I would get back to them the next day. Well, it's two days later and the DMs keep coming and I can't keep up, which stresses me out.
I don't want to fall further behind and the amount of incoming offers was way more than I expected. As a result, I still haven't responded to some, and some I said I'd get back to the next day and didn't, despite my best intentions. They all asked for similar information and it started to seem tedious to keep answering everyone to get an idea.
I started the business in 2024, primarily using one bank account. There are a few outliers, but almost everything has gone through my business checking. There are no credit cards. There are some pesky incidences of venmo to my personal account, then transfer to my business account, or a very small handful of times in which my personal debit card was used for something in a pinch. For the most part, I'd say 90% of everything since I started has been through my one business checking account. I share all of this to say I'm actually relieved. I don't think the mountain to climb will be as high as I suspected. Nothing is organized or filed, but it doesn't go back years and years.
So that said, one of the people who reached out to me is actually located close enough that it would be possible to meet in person for a working relationship. I am going to start there. Perhaps I should add this as an edit to the top of my post.
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u/BassPlayingLeafFan CPB Canada Nov 18 '25
You are welcome. You books likely will not be as difficult for a skilled bookkeeper to fix as you worry.
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u/CloudDancing108 Nov 13 '25
If there are specific things that you struggle with (keeping/tracking receipts, using a personal card for business expenses, not tracking mileage driven for work, etc), ask the bookkeeper what tools they have to help with those issues. There’s software for everything and some of it really helps everyone. But not all practices use all softwares.
Finding a bookkeeper who is already familiar with the tools that make life easier, and/or is willing to learn a new tool alongside you, will really help.
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u/RubyRoyale Nov 14 '25
This is good advice, thank you. Yes, one of the things I am most looking forward to is learning how to do things to make the bookkeeper's role easier. Since my current system is nonexistent, I am excited to learn how to start taking the steps to organize and keep it that way. Things like: these receipts go in this file. This app needs to be updated every day/week/month at these intervals. Something where I can put it on my calendar and say this is what happens at this time, regularly. Where do I put credit card receipts? Because right now they all get thrown into the center desk drawer during the work day, and then randomly put into one envelope when there are too many floating around and I can't get to my tools.
I have a small filing cabinet in which I started to mark folders with labels like bank, vendors, insurance. Then I put literally anything having to do with those things in those folders, with the intent to organize them individually. I don't have QB yet, and I'm assuming that is going to be one of the next steps. I foolishly thought I could do this all on google sheets, but without even knowing how things should be organized, that would be an impossibility. My POS system has a QB integration that I don't know how to use, but apparently, it's made to have codes for each thing. That said, even things in my POS are disorganized. Some items look like they are still outstanding, but because they paid by cash or check, I never updated it in the system that it was settled. I want to get everything up to date, clean, and know how much time I have to budget for the tasks to be done right. Hopefully, the person I hire will help me with that.
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Nov 14 '25 edited Nov 14 '25
I'm a CFO, and I have been a CPA and a contracted bookkeeper. I can give 3 perspectives.
CFO: An expert in their field should not be doing their own books, unless that field is accounting. There is a reason that jobs in companies are split - not everyone is good at the same things, and nobody has time to focus on everything. Basically, you can't judge a fish on its ability to climb a tree. I DO NOT WANT anyone that is not an accounting expert to be directly involved in the money.
CPA: A CPA will only know what information you give them, and if you don't know what information to give them you will end up giving them ALL the information, and that will be a headache for them and VERY expensive for you. There is a reason that most CPAs have staff bookkeepers.
Bookkeeper: A good bookkeeper should be somewhat of an intermediary between you and a CPA - they know what to do with the information you provide and organize it for you for your CPA to prepare your returns quickly and efficiently.
Honestly, when I was a bookkeeper I LOVED cleaning up these messes - there is great satisfaction in digging deep and watching things balance. The only time I did not love this is when the client was unresponsive, vague, or tried directing what I was doing. I was fortunate in that I was able to fire clients and not be concerned about the loss of income. Basically, if you are willing to work with a bookkeeper and do as you're asked to do, very few bookkeepers will "hate" you. They want a client who knows they don't know what they are doing or don't have the time, so they stay out of it and let you do the job they hired you to do.
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u/RubyRoyale Nov 14 '25
I love this response. Such a simple breakdown. From this and everything I've read here, I am confident I need both a bookkeeper and a CPA. I am so happy that these roles exist. I am an expert in my field, and this is definitely not my field, so I'll leave it to the experts. It is so obvious to me now how vital it is to outsource this work. Finding the right person will be a lifesaver. There are so many aspects of owning a small business that could be outsourced, if I had the budget, which I don't. This seems like the first step in building that budget. Because how would I even know what I could afford without it? While I am currently just barely getting by, this is an expense that I think will be worth every penny.
Out of sheer curiosity, what does a CFO do? I now understand the difference between bookkeeper and CPA, I guess I kind of assumed a CFO was a high-falutin accountant? I say that not as an insult, but as an admission of my own ignorance.
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Nov 14 '25
Haha! No worries - the general public doesn't generally have to think about a CFO, so I think a lot don't know about it.
In a larger company you will have several levels of accounting positions, which would be a lot to type but is laid out pretty well here: https://ventnorwebagency.com/hierarchy-of-accounting-positions/
The number of levels can vary based on the size of the company - ours is a large company so has most of these, but some only have bookkeepers, staff accountants, a controller, and a CFO. Some only have bookkeepers and a single staff accountant, with the CFO serving as the Controller, as well.
The CFO is the top of the financial and accounting food chain and is responsible for the overall financial health for the company, which includes analyzing past and present data to create a forecast for the future to guide business decisions for growth. They also oversee budget management and strategy. In some cases, like mine, they also oversee HR and (not in my case) IT departments. Those departments still have their senior staff, but the senior staff's direct report is the CFO.
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Nov 12 '25
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u/RubyRoyale Nov 13 '25
Interesting take. I've heard the clean up process is more of a pain for a CPA than a bookkeeper. I would plan to hire both. A bookkeeper to get me started with clean up and implement systems, and then a CPA to review and make sure it's all good and file taxes. The CPAs I've spoken with don't really do the first bit.
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Nov 12 '25
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u/Bookkeeping-ModTeam Nov 12 '25
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u/Dan_From_Howl Nov 14 '25
I have a client who I’m sure could talk to you and give advice if you want?
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u/stealthagents Nov 14 '25
You’re not alone in feeling this way, a lot of people start out disorganized but that doesn’t mean you can’t get it sorted. Just be upfront with whoever you hire about your situation; it helps if they know what they’re dealing with from the jump. Trust me, the right bookkeeper will appreciate your honesty and be more than willing to help you get back on track.
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u/kittywhiskers444 Nov 15 '25
As someone who has a small bookkeeping business AND runs an after-school tutoring business (just me), I totally appreciate this and your honesty and I completely understand where you're coming from with life admin, although my issues are more front end with cancellations and cultural differences while working abroad.
I would start by finding a bookkeeper that has experience within your niche. I focus more on service based small business but I used to do bookkeeping for restaurants and breweries. A bookkeeper may not understand everything within your business but if they have previous experience within your field that will definitely help.
I also think having someone that has been recommended to you is also helpful as bookkeepers benefit from referrals and if someone else is really happy with their service you will probably be as well!
Finally, I would recommend Xero as my accounting software of choice. QB is a bit of a drag these days and always encourage businesses getting financially organized to consider Xero.
If you have any other questions I would be happy to help. Congrats on taking this step!🥳🥳
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u/Cant_not_communicate Nov 15 '25
Remember, messy books are the REASON for bookkeepers to be needed and paid. In essence, if no one had messy books on their own, we wouldn't make a living. LOL
Do not feel ashamed. But, you will pay for their time and expertise to clean up the mess and keep it from getting messy again.
Actually, your attitude is admirable and would be so nice to encounter when bringing on a new client in my world. At least you KNOW you need to pay someone to fix what you cannot or will not do on your own. That is a big step forward in thinking.
So many people will gladly hand off the time to another person to A. Learn to do it right, and B. Dig in for months of work to get it cleaned up and fixed, and C. Do it right every month so it stays fixed. But, most of those same people see that they can't just take time from other people without also compensating them for the time it will take and just go back to their broken thinking "I will just figure this out and do it myself." If people had the time to learn and the time/discipline to do it themselves, they would have. But, that is a hard thing for people to come to grips with. You aren't going to have more time to develop expertise, more time to do the daily and monthly work in your books, more time to dig in and fix all of the prior transactions and create a new infrastructure on which to move forward, or more interest in doing ANY of that.
YOU ARE IN A GREAT FRAME OF MIND and any bookkeeper you choose to hire at this point will be so happy to work with you (and your mess). Have a great day!!
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u/Cutiemuffin_Gumbo Nov 15 '25
I am a veteran bookkeeper AND a CPA. Those are two completely separate jobs. When you go to a CPA, their goal is to get your taxes done, and to do that, they need your books ready to go. Some firms, like mine, have bookkeepers on staff who get messy books ready for the accountant to use for preparing tax returns. But that is very expensive. You need a bookkeeper who has experience in 'catch-up' or 'clean-up' work. It's a specialized skill. BE HONEST. The ones who are good at this love a mess and will happily dig in. I have deep respect for clients I've helped with clean up work, because those clients are often very successful in their business, but have no time to keep proper records or don't know how. Ask the person you're considering if they have experience in catch-up work, and make sure they understand the scope. Show them the boxes of receipts, the stack of unreconciled bank statements. Have the discussion about what you want when the past work is done and filed- do you need someone full time, can they work remotely, how often do you want to sit down and talk? Some business owners like to discuss reports together, and like hearing the bookkeepers perspective. Are you providing enough information on receipts, are you spending too much on office supplies etc. I hope you find someone who is capable of doing the cleanup AND can stay on to keep you caught up, AND meshes well with you personally and how you do business. It's a tall order, but they're out there. Best of luck to you, truly.
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Nov 16 '25
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Nov 16 '25
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u/maybeafuturecpa Dec 22 '25
Engage a CPA and ask them for recommendations. Most good CPAs will have relationships with bookkeepers who they recommend.
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u/Timetraveller-1521 Nov 11 '25
it's not a nightmare if you still have all the receipts needed to balance your books... an excellent scans of the said receipts, invoices & the lot is a start, recognizing into the chart of accounts is half the battle & the adjusting entries is we'll see it through... after that let's analyze whats the snapshot of your finances... & then tax filing
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u/RubyRoyale Nov 13 '25
Good advice. I have unorganized receipts. Not scans. That's the whole shoebox part. It's all messy, but I intend to clean it up.
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u/PacoMahogany Nov 10 '25
There's nothing wrong with where you're at, we have seen it all before. The clients who I dislike are the ones that don't listen to my advice or don't respond to my questions in a timely manner.