Bookkeeping Off-Season Planning That Pays Off

Summer’s quiet—Paul’s workload isn’t. While others slow down, our resident Bookkeeping Mensch, Paul Rosenblum speeds up. Come along as he shares how the summer months become his most productive time. It's perfect for him to tackle complex client projects, catch up on multi-year financials, and prepare for the busy season ahead. You’ll see how strategic bookkeeping during quieter months builds a foundation for smoother, more accurate reporting when business picks up. The episode delivers a clear message: by investing effort when things are quiet, you buy yourself control, confidence, and breathing room when it’s sheer chaos. Whether you’re a bookkeeper managing big projects or a business owner trying to stay ahead, this episode is a masterclass in planning with purpose.

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Transcript

Episode #60

It’s Father’s Day as I write this episode and I just got back from vacation yesterday.  But don’t worry – this is not a vacation episode like last year.  Nothing to report on financially with this vacation. We were pleasantly surprised to get what we expected.  However, when I get back from vacation in June (most of the time), it goes into a period of time that this year will start on June 16th and go right through the summer, although I will take some time off in July and in August.  But when I’m in the office, I will get as much done as efficiently as possible, so that I can go into Labor Day in good shape.

 For you bookkeepers listening to this episode, I am sharing the way I work in the summer.  For you small business owners, I am talking about how accessible I am to my clients over the summer even though clients and many tax preparers take much time away from their offices in the summer months.  I use the quieter time for some serious work as well as enjoying the summer the best I can.  So, this episode is about the summer projects in addition to my monthly bookkeeping work and the goal is get it all done by Labor Day, when everything gets a little faster.  It’s almost like Double A baseball in the minor leagues and then getting promoted to Triple A where everything is faster, and then tax season is the major leagues.  Yes, it’s JUNE, and I’m talking about tax season already. Don’t forget, take a look at the You Tube channel and if you want to contribute to the pod, check out the link in the notes here. Oh, yes, and I’m still Paul Rosenblum.  

Aside from my monthly bookkeeping duties, I have books to finish from business owners who wanted to be on extension in March and April. I also have a total of 4 projects to finish by the end of August or early September.  This is why the summer is as busy or busier than most other times of the year for me.  

Project #1: I have 2 more years to input for a client who I have spoken about before.  2 Credit Card and 4 bank accounts, and a tax return was just filed for about 3 years ago with a new accountant. After everything was input, the new CPA had only a handful of adjustments and changes that I had to make to the books. I have already inputted about half of what needs to be done to catch the client up to June of 2025.  I hope to get all of that done this summer, hopefully sometime in August. I will follow the same pattern as in previous years, knowing that the client will go through the entire Profit and Loss in detail with me and let me know what to make changes to.  Mostly personal meals vs Business meals (same restaurant), and travel destinations that included bringing the family. 

 Some expenses are business, others are personal – so we separate them appropriately.  Business meals on the Profit and Loss, personal meals on the Balance Sheet in the Equity section.  In this case, there are mortgages being paid not only from business accounts but from personal accounts that I don’t track since they would be 90-95% personal expenses.  So, when everything is done, I have to check to see to make sure that there are 12 payments made for two mortgages. If there aren’t, then I have to check them against the end of year statements.  Even if they are paid from the personal account that I am not tracking, that transaction has to be entered in the Equity section of the books, which, in this case, represents the incoming rent and the expenses for each property that the couple owns under a different LLC’s.

  As I have mentioned in other episodes, there should be 3 separate sets of books – one for each property, and one for the business that I am tracking and the main purpose of the set of books that I am creating.

 I also check to see if there are 12 payments from tenants of the properties for the year and if there are not, then the funds could have been put into a personal account that I don’t track.  The moral of this is: Separate bank accounts, and credit cards for each business that you have, if you have multiple businesses.  And separate your personal expenses from your business expenses. 

Project #2: A smaller project of a business that just started up and made their first sale this year.  I can probably do this one in two days, but it’s slow, careful work because the business is being run from an investment account which has so many ‘different’ kind of transactions in it that it has nothing to do with the business. So, this will be a lot of questions back and forth. There is not much more to say about this one. All I can say is that there are some people who have businesses who really shouldn’t. 

Project #3: This one I have spoken about before as well.  The company started in 2018, and they know the books have been very bad ever since. The tax service that they were using putting together books in a minimal way and filing tax returns.  I will be spending a lot of time this summer on this project. The company does their taxes in Accrual accounting, and I must still figure out how to deal with that in the books.  Once everything is entered, I can always go back to the tax returns and match up numbers by making journal entries in the books. This project will be very similar to what my father did for many years --- nothing to do with bookkeeping, by the way).  He was a film editor.  Some bookkeeping has a lot of similar editing components. Yes, there is a right way and a wrong way, but in some cases, there’s more than one right way of getting the numbers correctly.  I am going to start this project with QuickBooks Desktop, and we can always convert to the online version if we wanted or needed to. 

Project #4: I have spoken about this one before as well, but another 3 years to do to get the client up to date.  Similar to Project #1, with several credit cards and bank accounts, and since one company is now closed, so we are combining a small amount of income from that company in the company that I am putting together a set of books for.  I have about 50% entered so far, and again, I’ll follow the same pattern to get them up to date to June of 2025. And then we will go over all the categories together.  

I also have a client who is very late getting me what I need to put their books together properly.  It’s a hair salon.  The owner hasn’t gotten back to me with lots of questions that I have (although everything is input through April 2025) – and they haven’t gotten back to me with Petty Cash expenses from Jan of 2025.  So, I have catch-up on work there. And I just have to say that retail operations are very difficult, bookkeeping wise. There are lots of cash sales that might not be recorded in the Point-of-Sale system, but that cash is being spent on expenses for the company.  The bottom line is that they are getting deductions for the expenses but not counting the income.  

So, I push and push clients like that to get them to admit that particular cash sales did not get counted as income, but the cash was spent on deductible expenses. Can’t do that. The money that is spent, has to come from either revenue or sales, OR investment money from the business owner or from someone else. So, this project is 12 months a year, not only in the summer months.  I also read recently in Facebook posts in a bookkeeper’s message base that several people complained that they can never reconcile the bank account to the Square account (Square is a POS system, by the way). The cash issue is one reason. The other reason is usually how the client originally set up Square POS categories and items.  At the end of the year, I adjust the books to the total sales that Square says happened if they are higher than I am showing in the books. You could do that monthly as well if you’d like.  (And some people think bookkeeping is only about categories and data entry).  Nope.  It’s a lot more than that. It’s careful, sometime tedious work.

  And I will digress a little bit here -- when a large project is being done and I feel like I have control of it and I have a game plan to move forward, my initial anxiety about it goes down from what was originally an 8 on a scale of 1-10, to a 2 on that same scale.  So, when I feel like I have control of these projects, it’s almost like a ‘Moment of Zen’, like John Stewart ends his Monday evening show with.   

I am also going to include a client who is expanding the business to a second location, but because the owner is in the medical field, the second location has to be the same LLC because of the certifications that can’t be transferred or added to another company even with the same owner.  The bank statements are 25 pages long now – they might be 40 or 45 pages long. And I enter that data manually in QuickBooks Desktop. 

So, yes, the pool is waiting for me this summer and I’ll be there.  However, when I’m in the office, I’ll be working fast and hard to get everything that I have on my plate done before Labor Day.  I have talked about walking away from clients, which I have done, so the amount of monthly bookkeeping has gotten a bit smaller, which allows me to take on interesting projects to do over the summer months.   

So, that’s my summer ahead bookkeeping-wise, except for a death in the family and many things that have to be done that aren’t local.  But I’ll be bringing work with me when I am dealing with that out of state because I still want to finish things by the end of August so that I can start September on solid footing.  Be in your podcast devices soon--   I’m Paul Rosenblum.