Bookkeeper Training: Learn By Doing

In the last post I was discussing training. At the time, my plan was to write this next training-themed post about running a small business. I've decided to switch that up a bit.

It has been a very long time since I've written anything for the site. Long time readers surely assumed I'd disappeared for good, and there are likely many of you who signed up for the email updates months ago and have never received a thing. I could spend a full post just apologizing and berating myself, but maybe on a future post. This time I'd like to tie this into the original topic.

Shortly after my last post work got a bit hectic. A bit quickly became a lot. Before I knew it, my client workload had doubled. For a while I tried to keep writing. I'd start a new post, get busy with something else, and wouldn't come back to it for days. After a while I accepted the fact that client work had to take priority, and I'd get back to the site when I could.

This last year has been a great learning experience. I could (and might) write about the journey. Lots of questions came up along the way.

Should I change my schedule so I can keep writing?
Should I hire an employee to help out?
Should I say no to some of the additional projects I'm being offered?

Today I want to bring it back to training. There are many ways you can improve yourself as a bookkeeper. I listed off places you can go, and things you can read to boost up your skills. Those are all great, but I've realized something more important.

There really is no substitute for work experience.

There's a reason we don't let med students go straight from their final exams to their first heart transplant. (please tell me we don't) We can only internalize so much without any practical trial and error. The pressure to pass a final exam will force you to retain a lot of information, but there's just something different about the pressure of a real world deadline, and the risk of losing your job or costing the company money if you make a mistake.

In any lesson, you are taught best practices under normal situations. Your class might teach you how to process payroll for 10 employees. It will take you around an hour, and you'll be using industry-standard software at the comfort of your office desk. It will not teach you how to get those 10 people paid at the side of the road because your car broke down on the way back to your office and it's Friday afternoon. (yes, this has happened to me before)

I believe there are 2 big benefits to learning on the job.

As I've said, the first benefit is the deeper practical experience. Learning all the real world scenarios that you'll actually face is so valuable. In my career I've spent long stretches with one or two clients. I've become very good at solving their problems. Much of that training will transfer over to a new client, but every new client comes with new problems to solve.

The new client might use different software. They might be in an industry that has different reporting requirements. Or, maybe they really struggle with cash flow. If I'm used to paying employees and taxes on time but this new client has cash flow issues, how do I adjust? I could remain a bookkeeper for the next 60 years and still come across new challenges every day.

The other benefit is about overcoming procrastination.

How many things in life do you avoid doing because you don't know how? Or, in this case, how many clients or projects do you turn down or put off? I am very guilty of this.

My big example is this website. I wanted to start writing posts about bookkeeping in 2009. What I should have done is setup the simplest site possible, and just started writing. I was scared to just start, so I decided to learn everything I could about web design and content management.

First, I read a couple blog posts about a topic. Then I ordered some books. I bought a domain, paid for hosting, and paid for a couple popular Wordpress themes. I was going to design the perfect site. It would have great design (even though I can't draw a stick man), custom features (don't know a bit of code), and I'd implement all the SEO tricks to get 1,000's of visitors (clueless at marketing).

Months later, I had a couple half-started sites, and the realization that I was never going to be a web designer.

So, in early 2010, I scrapped all of that, and went back to the original plan. I setup a simple site with little to no design, and just started writing. And writing, and writing...

All of the clients I've worked with over the past 7 years have been because of this site. The fact that I've been too busy with client work to write is because I took the plunge and just started doing.

I highly recommend you do the same. I bet there's software out there you want to try out but haven't. Instead of reading about it, go setup an account and start using it. Too scared to use it on your clients? your own books with it this year. You can always go back to your old software if you hate it. If you do hate it, you'll be able to better explain to your clients why they should stick with what you're currently using. Even that small failed experiment will make you a better bookkeeper.


Ok, so it's been ages since I've written here. That means there are lots of people I've lost touch with, and others who I've never met. If you have time, I'd like you to introduce yourself. If you're reading this in your inbox, just reply to the email. If you're on the site, please contact me. Tell me a little bit about you, your business, your procrastination, whatever you'd like. I'd love to know who's out there, and what you're learning, succeeding at, or struggling with.

Take care.

Eric Matthews

I'm a bookkeeper, husband, dad, music junkie, and general tech geek. When I'm a bookkeeper, I focus on cloud bookkeeping. I write at, which helps bookkeepers and business owners move their books online. I work with apps like FreshBooks, Xero, Kashoo, Wave, and QuickBooks Online.

Subscribe to my free newsletter!