How do Independent Bookkeepers start to wind down into Semi-retirement or full retirement from what they've done for many years?

Have to have a plan, but what is it?

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I formed my business in 1994, with the intent of being a freelance bookkeeper, working for several companies in their offices or at home. That lasted 3 months, until I stumbled into teaching at a NYC computer school. This very quicly became 35 hours a week, and I all but abandoned the bookkeeping idea. When I started teaching Quickbooks desktop classes, and students came to me after class and asked for my business card asking if I am taking on clients, I realized that I could do both and started to build a business. And so, that’s where the freelance bookkeeping had a second start. It quickly grew to 10, 15, 30 clients. I was so spread out in my living room with neat piles of bank and credit card statements organized very carefully, I decided to take the plunge and get an ‘office’. My first one was in an office sharing facility, locally owned, and it was more of a cubicle than a real office. Not much privacy. The practice grew and grew. I moved to ‘WeWork’ which lasted 90 days. It was unbelievably loud — people were yelling across the hallway and the offices were not nearly soundproofed enough. I was 30 years older than any other person working on the floor at that time. Then I moved to another office sharing space that was brand new, and I loved the setup. Much quieter, very nice building manager, and reasonable rent. I am still in that building today, although in a much larger office.

I have spent a lot of time in the office in the last decade or two. Now, in 4 months, I’ll be entering my 8th decade on the planet and have been reevaluating where I am, and starting to feel my mortality. I feel like I am getting towards a crossroads of sorts.

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I didn’t discover accounting until I was around 38. I didn’t start a company until I was 41. I didn’t get married for the first time until I was 50. Obviously I got a late start on things. My age is real, my mortality is real, but because of the late start, I’m not done yet. I have more to do and more to say. The distractions in life get in the way sometimes for someone who is passionate about accomplishing things.

I’m not the best bookkeeper on the face of the Earth, but I haven’t gotten any complaints from any tax preparers, and they keep refering clients to me. I don’t have to be the best, but I want to be better than most. But how long can I keep up with 100+ clients every year? (yes, several of them are very small, maybe 45 minutes a month to complete) However, Two Questions:

1. What is the best way of slowly walking away from clients who are relationship based with me and their bookkeeping? So many clients trust me with their bookkeeping and wouldn’t trust anyone else. I’ve had people move away from NY to Florida or Tennessee, and they ask me if I would continue being their bookkeeper because they wouldn’t trust anyone else? And how many clients do I leave myself with when this long process is done?

2. What do I partially replace the bookkeeping with?

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Let me answer the second question first. That’s the easy one. I replace it with this and the podcast. The podcast started in 2022, not knowing if life would ever get back to a new normal after the pandemic, and now it’s 2024 and I feel myself getting tired more easily sitting at a desk all day and doing bookkeeping. I am starting to work slightly different hours and actually being more productive working fewer hours. It’s easy for me to write and talk about bookkeeping and related subjects and we are looking into several ways of monitizing the podcast by maybe getting into the education field with the teaching episodes. So, I do have a ‘plan’ there.

However, question #1 is a tough one for me, personally . I’ts so hard for me to walk away from anyone, even a difficult, demanding client who doesn’t understand that collaboration that should happen between them and their bookkeeper on a weekly basis. That’s the teaching gene in me — always wanting to teach and never wanting to give up on the people who just don’t get it. So, walking away from any client is mucho difficult.

I also know it has to be done. I know that I will eventually cut down on clients, work less hours, and my life will change. I will probably do more travelling, and I’ll see Wednesday Matinees of Broadway shows, take virtual classes, join interesting virtual groups, go to museums, and do things that I like to do. But I’ll always think about someone else doing the data entry on MY set of books that I have put together for clients, some of them, for 10 years or more.

If one works in an office, even for many years for one company, and you choose retirement, some of these same feelings might come up, but I would think not as ‘personal’ as they are if one is an independent bookkeeper with a relationship based practice— not just with people, but with their books. If someone is working at a job that they are passionate about, and either decide to cut down or an injury stops the continuation of doing it, then there might be a void in one’s life, even though the person can still be busy with other things and still be productive. It’s a big change.

I’m not ready for that quite yet, but can see it coming. For now, I’ll keep on doing bookkeeping, writing and recording podcast episodes and writing here on Substack.

Next newsletter, I’ll go back to talking about the core of what I am here for and the podcast.

Please email or join the chat here to suggest any topics for here or the podcast as we move forward.