Where Bookkeeping Meets Immortality

When the year ends, reflection begins. In this unusually personal episode, our favorite Bookkeeping Mensch, Paul Rosenblum, takes a pause and looks back at a year filled with loss, change, and a few big reminders that even bookkeepers have limits. He talks openly about grief, shifting energy, evolving client relationships, and what it feels like to age in a profession that runs on precision and stamina. As he looks ahead to 2026, Paul starts sorting through which clients, tax preparers, and workloads actually support his well-being and which ones might need to be gently shown the door. He also digs into the business side of letting go, the emotional weight of being the person everyone relies on, and the very real questions around semi-retirement, succession, and where bookkeeping fits in an AI-shaped future.

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Transcript

Season 6 Episode 7

It’s that time of the year again, and it’s time for us bookkeepers to adjust and get ready for next year. Aside from all the new laws going into effect on Jan 1st, and not knowing 100% yet what 1099 NEC’s we’re doing, as compared to Venmo and PayPal I am more anxious than I usually am. So, it’s as good a time as any for me to reflect on the past year before we start the next one. And don’t forget, go to the website and leave a voicemail with your question – the season of Q&A is coming very soon!  I’m Paul Rosenblum. 

On a personal note, this has been a tough year for me. In Feb., a friend from college had a heart attack and passed away quickly, and 24 hours later, my favorite CPA who I worked with had exactly the same fate. In June, my 98-year-old mother passed away (which was, unfortunately, expected), and I took very little time off from the office.  10 months later, I am still processing from Feb., and 5 months later still processing my mother’s passing. And like so many families, a mother or a father passing away breaks up the rest of the family, as did it my sister and I.  I am also dealing with my own mortality, and the need to walk away from clients in an organized manner and figure out how to move forward and trim down to clients who I like personally, who pay on time, and who respond when I ask for something, and realizing that we are on the same team.  I also must think about which tax preparers I want to work with in 2026. The knife is out, being sharpened and almost ready to cut. 

There are many accounting firms that just take the bottom 10% of lower paying clients and cut them. No emotion involved. But, as you probably know, when I let a client go, I do have emotion.  The business side of running a business is the toughest part for me.  It’s easy for me to work with struggling or small businesses to improve certain situations for them (and my suggestions have usually worked over the years) but giving myself advice and actually following through it is the hardest part for me, personally.

When I was younger and I was just starting out, I had lots of energy, wanted to learn, and thought that I could handle the bookkeeping for all businesses of NYC. That was looked at as ambition. (But if you are older and you have that attitude, it’s called a ‘God Complex’).   Now, I have less energy, I don’t really want to learn new things in bookkeeping much anymore and just want to do the bookkeeping for people who appreciate my efforts, email me what I ask for (or what they think I need even if I don’t ask for it) or if I don’t or can’t have access to particular statements that I need. In other words, lower my stress level.  As I have mentioned before, bookkeepers, many times, are the human punching bags of some clients and even of some tax preparers. And since it has been years of being on the receiving end for me, along with the personal losses for me this year, I have to try and change only what I can control.  And in reality, I can control the amount of clients I have, the quality of clients that I have, and the companies and kinds of companies that I do bookkeeping for. I can raise prices, trim clients off of my list, not work with certain tax preparers who are difficult, and even change the hours that I work. I forget sometimes that I’m the boss of me. Not my department manager or the owner of the business.  *I* am the owner of my business here. 

So, in December, I have always reflected about the year coming to an end. But I feel that in 2025 I am doing more reflecting and planning for the future than I ever have.  My patience is not as high with clients as it was for years, my concentration and work stamina is not what it was when I was working 12 hours a day, every day, during tax season, and my age isn’t what it was 5 or 10 years ago (obviously).

And now, for this week’s “Quick Tax Tip”. The ‘Checklist that your tax preparer emails you to prepare for taxes being filed in 2026 should NOT be thrown away. Don’t ignore it. Go through that list and gather any paperwork that applies to your situation and get everything to your tax preparer now or when it comes in the mail in Jan. 2026.  And now back to the episode. 

I have a whole new set of things that I am now being forced to think about. I’m not quite ready for semi-retirement yet, and I have to plan for my financial future and my life semi out of bookkeeping. Medial insurance is still taken care of since my wife is still working full time, and I’m covered on her policy. (I pay the rent, she pays for health insurance) (Yup, you heard that right!)  Should I move to a smaller office space on the same floor in my building? And as I get older, do I ever want to sell the business or the client list? And if something happens to me and I can’t work for a while, who is going to call all the clients and let them know and get them all of their files if they are not online with their accounting?  And if I can’t work, what am *I* going to do?  

This is the first episode that I have gotten this personal about myself. And yes, it does feel very strange. And surprisingly, it is difficult to write about and hear myself saying all of this into a microphone. However, this happens to all of us, in whatever business you are in, and I know there are lots of bookkeepers listening to me right now. A bookkeeping business is somewhat unique (as many service-based businesses are) because it’s very hard to announce that one will retire in 3 months after tax season, for one example. In my case, 85 businesses will be scrambling for new bookkeepers and that trust that they have had in me will have to start all over again with someone new.  So many of my clients, even when they have moved from NYC to another state (or even all the way to California), told me that they would like to keep me as their bookkeeper because of the relationship that they have with me and since I work so well with their tax preparer. 

Being a child who got tons of bad attention from both parents, and very little ‘good’ attention, and even if that was tainted, this is where the relationships with my clients come into play.  We all like to be liked and we all need the pat on the back sometimes, but I admit, I need it more than most. (By the way, Leave me fan mail, it really makes me smile – or leave me a voicemail at the website). 

So, cutting clients, if I have a not so good relationship with them – is difficult since it brings back memories from childhood, and cutting clients who I have a great relationship with will be really difficult when I get to that point.  

Right now, in 2025 (and in the past year), I have cut several clients who can’t afford to pay me regular bookkeeping rates. I am cutting clients who are slow payers (people who pay me in 3 or 4 months, even after I send them invoices every month and get no response). And I am in the process of cutting one particular tax preparer out of my life because of his moodiness, border line abuse, and unpredictability in his behavior.  

I need to start to think about what I want the next chapter of my life to be.  I want to do bookkeeping until my body can’t do it anymore since I do really enjoy it, but I also have to pick people who understand what I am trying to do for them and pick the kind of companies that really interest me bookkeeping wise.

So, it’s the end of 2025, and I reflect. I reflect on the business, the past year, the next year, and my life in general. And I’m sorry to say it again, but --- mortality comes into the picture as well. 

I also reflect on the progress of A.I. How long are small business bookkeepers going to be able to stay in business?  When is A.I. bookkeeping going to take over?  Will it be a slow process or a much quicker one? No one has that answer. 

So, this Thanksgiving and holiday season, I will be thankful that I still have my health, I am still working every day, people still tell me that I don’t look like a day over 60, and I can still get on NYC busses without them ‘kneeling’ down to get me.  I am thankful that I can walk up two flights of stairs to the elevated subway and not feel dizzy. I can enjoy Broadway shows, and I can walk the ¾ of a mile to the office almost every day, and the ¾ of a mile back home almost every day. (in less than 20 minutes, by the way). I will try and focus on the good things and my New Year’s resolutions are to continue trying to  be a good human being and treating people well, trying my best to be a good bookkeeper (although mistakes will happen), and also enjoy the other parts of what life has to offer. I live a pretty quiet life, and will and have never been the ‘partying’ type, but I am trying hard to figure out the next life chapter and the chapter after that. 

What are you reflecting on towards the end of 2025?  Write me an email @Bookkeepermensch@gmail. 

Hope your Thanksgiving was a good one -- not too much fighting with the family, and that the flight that you took to get there and back wasn’t delayed too much.  

Reflectively, yours--- Paul Rosenblum