Bookkeeping Without the Burnout

Feeling burned out after tax season and rethinking how (and who) you work with? Paul Rosenblum is right there with you—trading high-stress clients and tangled accounts for quality work with people who actually pay (and say thank you). He shares real-world stories, hard-earned boundaries, and bookkeeping wisdom that helps you work smarter, not just harder—because sometimes the only thing messier than mixed finances is your client’s idea of “organized.”

Transcript

Episode 57

I have been trying to get used to a regular life after the end of tax season 2025, and have planned and booked our vacation, saw a movie in a movie theater recently, and getting back to better sleep.  It takes a while for me after the energy, stress, and frankly, the amount of work that tax season entails for me to get back to normal. I’m almost there. So, I’m (almost) Paul Rosenblum.

By the way, check out the YouTube channel for some video shorts and leave a text message or email me and let me know what you’d like me to talk about here in future episodes.  Are you a business owner?  Do you have medical practice?  I’d love to speak to you if you are looking for a bookkeeper.  I love doing bookkeeping for medical practices! 

Today, I will be talking about 2 different clients who I will be working on or finishing this summer to bring them totally up to date. I’ll be talking about them from a bookkeeping standpoint. 

However, before I get into the bookkeeping aspect of today’s episode, (and I know I have spoken about this before), but I am at a point where I have made a general plan for my own business future.  I am cutting down stressful clients, clients who can’t afford higher prices, slow payers and even cutting out working with bad or lazy accountants. I am getting my “mojo” back that I had begun to lose the last year or so and didn’t really know why.  It’s not that I don’t enjoy bookkeeping -- I do! Really!  It ended up being the stress dealing with all types of personalities, client businesses that weren’t making a profit, and me trying to help them fix it, and just the quantity of work that I had to do. I used to have infinite patience for tough personalities, late payers, and even people who have businesses who shouldn’t. But my patience level is not as high as it used to be, and it also seems that people don’t like to take suggestions anymore from others, especially bookkeepers. 

 There are many accountants who go through tax season just filing extensions for more than half of their clients with the plan of finishing them during the summer and be ready to file the final tax return by September or October 15th. I have always prided myself on being able to do the bookkeeping for every client well before the deadlines that accountants made to me to have the books ready for the tax return or extension.  For years, I was able to finish all the books. But as I got older and I started to work a bit slower, that started to change.  There are always clients who WANT to be on extension, but I always loved to be able to get them finished anyway and ready to go by late Feb/early March for the corporations, and late March for everyone else.  

I realized that I can’t do that anymore, as I want to and should start cutting down and enjoy my senior discounts that I get these days. So, I am cutting down the number of clients, and as I do that, I realize that since I am slowing down, there is less stress, and when there’s less stress, the quality of work goes up. So, my mojo is back.  All good.  At least for now, until I have to re-evaluate again, eventually. 

The 2025 tax season is over, and I have 4 projects to finish by the end of August, along with the monthly bookkeeping.  Today, I want to talk about 2 of them from a bookkeeping viewpoint, not only for bookkeepers, but for business owners as well to try and understand why the process takes much longer than they thought it would and why it costs more money than they thought it would. 

1. A project that I have had on my plate for about 3 years, that started with 2019-2022 not filed (and now 2023 and 2024 also not filed). I’ve spoken about this project before -- several different credit cards and bank accounts, expenses and income all mixed between 3 LLC’s and personal expenses, and because they are all mixed, everything is carefully entered in one database although if the accounts were all dedicated to the individual businesses, we would have 3 different databases. I just finished 2022 and we are putting the finishing touches on that before tax filing.  2023 and 2024 will hopefully be done by the end of August. In Canada, I’m told, this is a gigantic no-no, as personal expenses and business expenses cannot be shared on the same bank account or credit card. 
2. Another client with the years of 2022-2024 not entered or filed yet.  The client has a similar scenario – 2 different LLC’s, (and a third one started in 2025), 5 different credit cards, 3 different banks accounts all mixed together—including some of the credit cards being paid by the personal bank account which I am not tracking, except for the credit card payments made. The first year was the toughest, because every entry had to be scrutinized … was it a personal expense, a business expense for business #1 or business #2?  The second year of 2022 is much easier, since I can follow the pattern from the previous year. 

Since these are very similar scenarios, let’s get into some of the nitty gritty and how to set up the bookkeeping.  In the first case, when I first started, I was told that the client had one company, 2 properties (both separate LLCs in separate states), and personal expenses all mixed in together. 

 Several bank accounts, even investment accounts that they were using to pay expenses and lots of transfers from the investment accounts into regular business checking accounts and personal checking accounts.  The client is in the clothing business, and they have a family with young children. So, how am I to tell if they go to a clothing store, what they buy for clothing samples for the business, or clothing for the kids or them to wear?  Each entry has to be put in an ASK account for them to tell me what they are- to be correct.  The same with meals.   Personal meals vs business meals.  Gas or electric charging for the car – business expense or personal expense?   I have an ‘Other expense’ ASK account for each bank account and each credit card account and when each month is entered, I will export and send them a spreadsheet for them to go through and reclassify. I did that for the first 2 years, until I saw a pattern.  Then I followed the pattern with the understanding that we will all get together to go through every entry and move specific transactions to where they belong. 

The business expenses are on the profit and loss. The expenses for each of the two pieces of properties are on the balance sheet as ‘Equity’.  If there were separate bank accounts for each entity, then we would have separate databases, to match what the tax preparer will do with Schedule C forms, but in this case, everything is all mixed together,  I have both properties set up, each with subaccounts in the equity section, so mortgages, property taxes, and maintenance and construction are all separate for each property. 

 As I was putting together the books, I found out that there was another business which I didn’t even know existed.  So, what I had booked as income were actually loans from the other business.  I now have access to that business and will start that sometime this year (they have someone currently keeping that database up, for now). 

So, the trick is to get as much information from the client as possible if you are a bookkeeper, and if you are the client, to tell your bookkeeper everything that they need to know to put your books together properly. 

And all of these hours and hours of work are all for a company that is not making a profit, but the books still need to be done properly and filed.  One of the pieces of property will be sold sometime this year and I think a new business will be starting.  I am trying to push the client to have separate credit cards for each entity, but their credit rating isn’t great, so they might not have a choice. At least for now. I really like the client, and this is all part of my thinking for the future.  Walk away from smaller clients and do the bookkeeping for multi-entity clients who I know will pay me in a reasonable amount of time.  Work, but less stress, and working with people who I like.  Isn’t that the idea of being an independent bookkeeper business owner?  I am now 70+ years old, and I am still learning lessons. Which is one reason why this podcast exists.

If I can learn new lessons, so can you!  

The other client is a similar situation, but no property. Two businesses, 5 credit cards, all mixed in together, along with a personal bank account being used for both businesses.  What do I do when there is a credit card that is being paid by the personal account and not by either business?  I entered that payment as a journal entry debiting the credit card account and crediting ‘additional capital’ under Equity.  I don’t want to track the entire personal bank account of this particular client. And this client is another good one – pays me on time and even says thank you with the payment. And for all of you business owners, yes, bookkeepers need that thank you occasionally. We really do. We do need to be recognized for our hard work, and not just hearing complaints about how long it takes to get done, or how much we charge, or how many questions we ask the client and the scrutiny that we give our own work.  Yes, bookkeepers are real live people too. 

So, I have a busy summer in store, but hopefully not a stressful one. 

 I was thinking about hiring other people to do some of this work, and I have spoken to others, but that would actually slow things down, since there is a learning curve for each specific situation, and I also have come to admit, it’s a hard thing for me to let go of the control—especially when people are working remotely. Busy, but not necessarily stressful. At least not in the office.  But as family members get older, there are other things to deal with which interfere with my bookkeeping! 

Personally, I have always been rather consumed with bookkeeping since I ‘bumped into it’ 30+ years ago. Something about it is just fascinating to me.  It’s like a giant jigsaw puzzle that you know that all the pieces have to fit together.  The only potential difficulty is that there is more than one way to fit the pieces together, depending on the knowledge of the bookkeeper and tax preparer.

  For example, if a corporation owner is on payroll, and also takes distributions throughout the year, that’s fine with the IRS.  However, the tax preparer could convert the distributions into payroll to lower the profit of the taxable income for the corporation.  Or even the other way around sometime during the third or fourth quarter to adjust payroll and distribution amounts for a lower liability with the IRS.  So, pieces of the puzzle fit together sometimes in more than one way.

Bookkeeping is very close to film editing, which my father did for 40 years and had a real talent for it. So, not only do I get the bookkeeping gene from my father’s mother, I get the film editing gene from my father directly.  They truly are quite similar. The teaching gene, which is just as dominant, comes from my mother, by the way. This is why I work so much and am passionate about bookkeeping and this podcast equally.  This is why I need more than 24 hours a day and be able to sleep less hours and not stop for meals and even save time teleporting to work and to vacation spots.  

Actually, I’m taking the day off, setting up a new computer so that I don’t lose any regular working hours.  

I’m almost myself again ----  Paul Rosenblum