What r/Bookkeeping keeps coming back to
Complaints raised here by more than one person. One-off posts are not included.
51 recurring problems · 128 threads read · read since September 2026 · Reddit
Raised more than once here
Most people first.
- 47how do I get my first client?“I do wish more CPA firms would be willing to mentor and hire bookkeepers. I’m stuck in the “not enough experience” to get hired at a place, but educated enough to do basic level AR/AP, reconciling and general recording. If I can’t find someone to work for, I’ll just start working at low level, doing low cost services anyway. I like bookkeeping a lot. I just don’t have enough experience and firms don’t “want to train”. It’s frustrating.”
- 43How to find a cheaper CRM when HubSpot gets too expensive“I have taken on a small construction company that performs home models and builds homes from scratch. Keeping books for the construction industry is where I got my start, so I understand how it so different than any other type of bookkeeping, my problem is the software.”
- 40Why are teachers expected to be available 24/7?“I have a bookkeeping business outside of my FT job & i find it hard to do any work after work and when i do work on the weekends i feel like i get nothing accomplished”
- 39Why does every software update make things slower and harder to find?“It's getting to the point where it's adding time to the docket with the amount of reloading pages/regenerating reports I have to do.”
- 33Doing higher-level work without a pay raise“had a gig last year that wanted me to also run their social media because "numbers and marketing are basically the same thing"”
- 30Why is accounting software like QuickBooks so bad?“I mean QBO is dogshit and so are its reports but everything else is fine.”
- 30How to clean up months of messy client expense records“Now I get to spend hours going through bank statements and receipts trying to figure out what all these transactions actually were.”
- 29How to figure out how much to charge for freelance work“And then monthly I was going to charge a range of 700-1100 for basic bookkeeping. But she wants to do the bookkeeping and have me check it. That would be a lot more work than doing it myself. I know I need to charge more for having her do it and me review it, but I'm not sure how to do that.”
- 28How to handle clients who demand refunds and bully you“She has a few clients who just ask way too much of her and she can't seem to say no.”
- 28How to get first paying customers without an audience“Tried lead-gen services early on and got mostly tire-kickers who never converted.”
- 25How to understand a confusing legacy software system you inherited“You’ll double-enter revenue. You’ll double-enter expenses. You’ll “match” things that aren’t matches. And you’ll feel like you’re bad at bookkeeping.”
- 19Why is this community full of sales pitches and spam?“I'm on a call right now. It is my third call this week from someone in my networking group who wants to "help" me become a life insurance agent.”
- 18How to respond when a client says your rates are too high“She said to me "you're the most expensive bookkeeper" they've ever worked with”
- 17How to handle expense reports without being good at math“Running a small finance team at a Series A startup and trying to cut down on the back-and-forth with expenses. Right now recipets come in through email, photos, Slack messges, you name it.”
- 14How to handle running a business completely by yourself“Would anyone be interested in a mastermind type group? Maybe get together to discuss pain points in our businesses once a week? Share things we've done to over come them ect?”
- 14How do you know HubSpot and QuickBooks are still in sync?“Have a client that switched to adp workforce mid year. It's a nightmare to use.”
- 13Simple offline accounting software without monthly subscriptions“Ideally I'd like something that runs as a portal, CRM and also lets me do the accounting from the platform.”
- 13Is it normal to have no training or supervision on a new job?“The part that is making me reconsider it is the training situation. The woman I would be replacing finishes next Friday. From what I understand, after she leaves I would essentially be responsible for the bookkeeping function myself.”
- 11How to handle constant scope creep in project management“1M revenue one year bookkeeping cleanup. removed duplicate sales, imputed over 300 missing expenses, fix miscategorized sales, fixed product mapping, sorted through 100’s of paper invoices and receipts to categorize, traveled to client to retrieve documents. how much should i charge for this?”
- 11How to learn accounting software without any training“Principles are clear but not being able to learn quickbooks or just get too lost in it,any suggestion to make it a bit easy?”
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How much more often a topic shows up here than across every forum we read.
open-source118.3×learning curve118.3×b2b SaaS118.3×difficult clients118.3×