7 Lessons You Learn After Starting a Bookkeeping Business

There’s a big difference between knowing how to do bookkeeping and knowing how to build a bookkeeping business.

You can understand reconciliations, financial statements, cleanup work, QuickBooks, and all the technical pieces that make you good at your job.

Then you start your own firm and realize: Oh. I have to get clients too. 

…And price the work.

…And lead people.

…And manage your calendar.

…And create processes. 

…And deal with mistakes. 

…And somehow keep the business from taking over your entire life.

Erin Pohan, founder of Upkeeping, knows that transition well.

Before starting her own bookkeeping business, Erin had years of accounting experience and bachelor's and master's degrees in accounting. But despite her technical background, owning a firm wasn't something she had seriously considered.

During an interview for another bookkeeping position, the owner stopped and asked her a simple question:

Why aren't you doing this for yourself?

That question helped change Erin's trajectory.

Today, Upkeeping is a team of four serving around 45 clients. Erin shared on the Millionaire Bookkeeper Podcast that the business generated roughly $250,000 in revenue the previous year.

But she didn't get there by having everything figured out.

Here are seven lessons from Erin's journey that can help you build a better bookkeeping business.

1. You Don't Have to Feel Ready to Start

Erin eventually came across a bookkeeping-business workshop from Serena Shoup of The Ambitious Bookkeeper (who we also had the pleasure of interviewing!). 

The workshop cost around $27.

Interestingly, Erin said she may have initially signed up less because she was determined to build a firm and more because she wanted access to other people doing the same kind of work.

By the end of the workshop, however, she had created the name Upkeeping and started taking real steps toward building a business.

She joined Upwork and landed her first client.

And before that first Zoom call?

She was shaking.

That's an important part of the story because it's easy to look at someone several years into business and assume they possessed some level of entrepreneurial confidence you don't.

Usually, they didn't.

They just did the uncomfortable thing enough times that it stopped feeling quite so uncomfortable.

Erin eventually developed a much simpler approach to sales conversations: learn about the prospect's business, explain her own business and background, uncover the prospect's actual pain points, and determine whether Upkeeping can solve them.

You don't need to become a completely different person to sell bookkeeping services. You need a process and repetition.

2. Don't Let the Fear of Not Knowing Everything Cost You Opportunities

Several months after starting Upkeeping, an e-commerce company approached Erin through Upwork.

Her initial reaction was essentially: I don't know if I can do this.

E-commerce introduced complexities she hadn't mastered yet, including inventory, Shopify, Amazon, international sales, payment processing, and the challenge of reconciling multiple systems that don't necessarily tell the same story.

She nearly turned the opportunity down but decided to give it a try.

Years later, Erin described that company as one of her favorite and highest-paying clients.

That doesn't mean bookkeepers should accept work they're completely unqualified to perform.

It does mean there's an important difference between being incapable of doing something and simply never having done it before.

Sometimes growing your bookkeeping business requires being willing to research, learn, ask questions, develop a process, and expand your expertise.

3. Your Biggest Mistakes Can Create Your Best Processes

Erin openly discussed one of the hardest experiences of her business.

A client had taken over accounts receivable while Erin was dealing with an injury. Sales receipts were being entered into QuickBooks, but a checkbox authorizing the customer charges wasn't being selected.

The transactions appeared on the profit and loss statement, but the charges weren't actually processing.

By year-end, roughly $75,000 was sitting in undeposited funds.

Most of the money was ultimately recovered, but approximately $5,000 wasn't and Erin lost the client.

It hit her hard enough that she sought therapy to work through the experience.

Years later, however, she unexpectedly encountered that former client in person and described their gracious interaction as a healing moment.

More importantly for her business, the mistake changed her processes.

Her takeaways included demanding bank statements for reconciliations and consistently reviewing undeposited funds.

That's what good bookkeeping-business owners do with mistakes.

Don't hide them.

Don't pretend they'll never happen.

Figure out why the mistakes happened and build a system that makes the same mistake less likely to happen again.

4. Being the Bottleneck Isn't the Same as Being Valuable

Hiring people doesn't automatically mean you've successfully delegated.

Erin discovered that firsthand.

She worked with an operations specialist who mapped the tasks inside Upkeeping.

The specialist pointed something out: Erin's name was attached to roughly 80% of the work.

Her existing team members could perform their portions beautifully, but work would eventually funnel back to Erin for completion.

So everything piled up.

The team wasn't necessarily the bottleneck. Erin was.

That realization helped lead to another hire whose role was intentionally designed to remove work from Erin's plate.

If you're growing a bookkeeping firm, periodically ask yourself:

If I disappeared for a week, what work would stop?

Those tasks show you where the business is still too dependent on you.

5. Protect the Capacity You Create

Delegation creates another sneaky problem.

You finally remove five hours of work from your week...

…and immediately find five new hours of work to replace it.

Erin specifically mentioned having to train herself not to take on more simply because she had successfully offloaded responsibilities.

This matters because growth shouldn't only create a bigger business.

It should create capacity.

Capacity gives you room to lead your team, think strategically, develop relationships, create content, pursue new opportunities—and occasionally close the laptop.

If every efficiency improvement simply results in the owner cramming more work into the empty space, the business hasn't really become more sustainable.

6. Your Calendar Reveals Your Actual Priorities

After experiencing severe burnout, Erin became more intentional about protecting her time and energy.

One tactic is remarkably simple: She blocks her calendar.

And she respects those blocks.

If she sees two meetings back-to-back, for example, she may deliberately block space afterward to reset, go for a walk, or get some exercise.

I echoed the same lesson in my post-episode recap: it's easy to say something is important, but your calendar reveals where your time and energy are actually going.

For bookkeeping business owners, this becomes increasingly important as the company grows.

Client requests will fill whatever space you give them.

So will emails.

So will Slack notifications.

So will administrative work.

Your highest-priority work needs a place on your calendar before lower-priority work consumes the day.

7. Don't Build Your Bookkeeping Business Alone

Community comes up repeatedly in Erin's story.

As a military spouse who moved frequently, she learned to establish relationships quickly.

When she entered the bookkeeping world, she found herself working alone at a desk and wanted people who understood what she was experiencing.

That desire eventually became something much bigger.

Erin created Wave Seattle, an in-person gathering for women in accounting.

The first event brought together approximately 65 women from 10 states and Canada. The next grew to approximately 100 attendees.

But community isn't just about conferences.

It's about having people you can ask:

Have you dealt with this client situation before?

How are you pricing this?

How did you hire your first employee?

Am I the only one struggling with this?

Technical education can teach you bookkeeping.

Community can help teach you how to survive and grow as a bookkeeping business owner.

You Can Figure Out the Next Step After You Start

Erin didn't begin Upkeeping knowing exactly how to build a team, sell services, prevent every mistake, manage burnout, delegate effectively, or create an accounting conference.

She figured those things out while building.

Her first year generated roughly $40,000 in revenue.

A few years later, the firm was around $250,000 in annual revenue with a team behind it.

There were mistakes between those two numbers.

There was burnout.

There were lost clients.

There were lessons she wishes she had learned sooner.

That's exactly the point.

Starting a bookkeeping business isn't about proving that you're already a perfect entrepreneur.

It's about becoming a better one as you go.

Listen to the Full Millionaire Bookkeeper Podcast Episode with Erin Pohan

Want to hear the full story behind Upkeeping—including Erin's early discovery calls, the $75,000 mistake that changed her processes, building her team, navigating burnout, e-commerce bookkeeping, and why community has become such a major part of her work?

Listen to “How She Built a $250K Bookkeeping Firm Without Having It All Figured Out | Erin Pohan” on Millionaire Bookkeeper.

Build Your Own Bookkeeping Business

Technical bookkeeping skills are only part of becoming a successful bookkeeping entrepreneur.

At Time Capital University, we help bookkeepers develop the practical skills needed to build businesses around their expertise—from mastering specialized bookkeeping to learning how to attract and close clients.

If client acquisition is the piece you're trying to figure out, join Go Pro Bookkeeping to learn how to attract and close bookkeeping clients as an introvert.

If you want to develop specialized bookkeeping expertise for real estate investors, check out Bookkeeping for REI.