The Best Time of Year to Start a Bookkeeping Business

podcast Feb 05, 2023



Today, I want to answer a question I received recently from somebody who was applying for one of my programs, because I’m guessing this question is on some of your minds, as well.

This person wanted to know this: if she joins the program now (late January/early February) and takes a couple months to complete it before starting a bookkeeping business, will that be bad timing? Will she be starting her business during a slow season for bookkeeping?

Most people know that as bookkeepers, our busiest time is in the month of January. From the time when statements are closed onward, we're trying to crank out that last month of data while looking at 1099 requirements, filing them, communicating with the tax preparers, and so on.

By the end of January, I am, for the most part, finished with that year-end review. That's our busy season, though most people are thinking about bookkeeping and tax through April 15th.

Because of this, a lot of people start to think that if they aren’t starting a bookkeeping business during that busy season, or if they’re not already established, they’re going to miss a huge rush of clients.

Spoiler alert: that’s not true.

There is no bad time for starting a bookkeeping business. So in this post, I want to put a spin on each season of the year to show you how you can really build a successful bookkeeping business at any time of year.



Stop Judging Yourself

People tend to think that the summer is slow for bookkeeping; however, summer is when I built my bookkeeping business intentionally back in 2019. I really revved up the strategies and the growth that I then turned into my program, which is now Life By The Books, at that time.

I grew thirteen clients in just a handful of months over the summer. I had an intention to sign five clients, and I signed thirteen over the course of this supposedly “slow” season.

Summer’s not too slow for you to think about starting a bookkeeping business. Neither is the beginning of the year. Neither is the spring. Neither is the fall. Neither is the end of the year.

There's no wrong time for starting a bookkeeping business. The right time for starting a bookkeeping business is when you understand that it's the right thing for you, when you're sold on it, when you're motivated, and when you're ready to start taking the steps and to stop looking for reasons to stall.

Even if the beginning of the year was the best and only time for starting a bookkeeping business, now would be the time to start that process so that you will have everything in place to get it going next year.

The best time for starting a bookkeeping business was probably the first time that it came into your mind. But if you're like most natural humans, you ignored that thought for a while. You dismissed it. You poked holes in it. You told yourself all of the reasons why starting a bookkeeping business wouldn't work for you, and for whatever reason, you didn't start yet.

In my last post, I talked about giving yourself permission to mess up; this is one of the areas where you need to forgive yourself for messing up, if you’re feeling the weight of that “mistake.”

You had the idea for starting a bookkeeping business a while ago, and that would've been a great time to start. And it’s easy to get bogged down by the thought of, “If I had started then, I would be so much further along now.” But for whatever reason, you weren't ready then. You’re ready now.

Stop judging yourself. Now is the second-best time to start. And if you start telling yourself why it's not a good time of year for starting a bookkeeping business and end up stalling until it's the “right” time of year, you're going to find yourself right back where you are today.

So what if you don’t grow quickly at first? Instead, commit to the long-term vision that you're working on. When you do that, you can continue to grow rather than sitting still and not going anywhere.

If you're not doing anything, you're not growing, period. So instead of judging the speed at which you might grow if you start now, let's just start now and release any kind of time pressure. It can happen fast—it did for me—but it doesn't matter if it happens fast or not, so long as it’s happening.


January to February

Let’s talk about the different seasons and how things change depending on when you start your bookkeeping business. 

At the beginning of the year, you probably need to do absolutely nothing to grow if you've already gotten your systems in place. If people already know what you're doing, if you already have a way for people to inquire about working with you, then you probably need to do next to nothing, because you've already told people that you're a bookkeeper, and people are thinking about bookkeeping at the beginning of the year, especially proactive people who didn’t have their books done in the previous year.

In January, these people are thinking, “Oops, I dropped the ball in 2022. The whole year went by and I didn't do my books, and I don't want that to be my story this time next year.”

That's how you can speak to those people. You can say, “It's the beginning of the year. You didn't do your bookkeeping for last year. Let's make this year's New Year's resolution getting your books under control so you can see how your business is doing, increase your profits, and actually make a change in your life because you're keeping your money. Because now you're not just focused on sales; instead, you're seeing the whole picture in order to understand what you're bringing in, what you're spending, and what you're left with, and then you can work to improve that.” That would be my beginning-of-the-year messaging if I needed to do it.

If you have clients today, I really think that the best thing to do in January is to serve your current clients. And once that year-end wrap-up is done, if you’re ready to start growing, you can get to work on that.


March to April

So that’s how to get the proactive people in January. Your less proactive people are waiting until April to then go, “Oops. I not only didn't do my bookkeeping for 2022, now we're in April of 2023, and I can't find a bookkeeper who wants to do this, or a tax preparer who will even talk to me in April. They're all telling me that they're booked.”

So if you're a newer bookkeeper and have capacity, this is messaging you can play with. You can say, “Taxes are due, and you can't find a bookkeeper. You can't find a tax preparer because you waited too long. I can help you, and more importantly, I can continue this for you monthly so that this doesn't happen to you next year.”



June to August

Once you get into the summer, you're going to start hitting procrastinators who are maybe a year behind the people who were thinking in January, “Oh crap, I didn't do my books.” The bigger procrastinators are now in the summer, and they said that they were going to start. Maybe they couldn't find somebody to do their taxes in April, so they filed an extension and they still haven't even done those taxes from 2022. And now we're into the summer of 2023, and they’re going to be in a bit of trouble.

If you're looking for clients, summer is a good time to say, “Oh my gosh, it's June. Half of the year has already passed us by, and you still haven't touched your books. I know you said you were going to DIY it. I know that you might’ve even bought my DIY template, but have you used it? Are you actually updating your books? Or are they collecting dust?”

It can be a great time to remind them half of the year is gone and they haven't done that thing yet, but it's not too late. You can still catch them up from January to now, and you both can get this thing rolling. You’ll get them caught up, and then they'll get those financials every single month so that this sense of stress is gone and it's being handled completely for them every month.


September to December

If you’re starting a bookkeeping business in the fall, it's just more of the same messaging. You're going to start running into the extension deadline, which is the time where I signed one of my clients, actually! It was the fall of 2022 and their 2021 taxes weren't filed, so they needed me to hop in and help them with that, as well as make sure that this didn't happen to them again.

Starting a bookkeeping business in the fall can be the time where, if you’re booked up a bit already, you can start saying, “Hey, I'm signing clients this month through this month, and then I'm not signing any clients over the holidays. I'm basically closing my doors to new clients until I get through January.” Or, if you’re really new, you can head into fall by saying, “Three months left in the year. Almost time to start thinking about what you're bringing to your Thanksgiving dinner. Have you done your books yet? Or are they still collecting dust?”

Starting a bookkeeping business at this time requires the same general messaging as summer, just different timing. And by the time that's done, you're into December and you could start thinking about signing people so that you can get them in better shape for January.



Any Time of Year Works…As Long as You Find the Right Messaging

When I say any time of year is great for starting a bookkeeping business, I mean it—but it is important to pay attention to the messaging aspect. When starting a bookkeeping business at any time of the year, there's strong messaging relating to why your clients or potential clients should feel urgency to look at this, how you are going to get it done for them, and how you're going to stop this bad habit and make it never, ever repeat itself by offering your monthly services.

Don’t let fear of “bad timing” stop you. The best time for starting a bookkeeping business was the first time you wanted to start…and the next best time is right now.



Learn how to take your bookkeeping skills and turn them into a business that allows you to replace (or surpass) your corporate salary, be present for your life, and profoundly impact your clients without selling your life in the process by joining Life by the Books (LIBBY).

If you're looking for more tips for bookkeeping, insight on how to become a bookkeeper, and how to say hello to a more confident business model, enroll in Become A Bookkeeper (BABs). 

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