When Hiring a Bookkeeper Starts to Make Sense

Hiring a bookkeeper is rarely a snap decision.

More often, it’s something that builds gradually — a shift in how you want to spend your time, a shift in what your role in the business looks like, a shift in what feels sustainable.

If you’ve been circling the idea, here are a few markers that can help you sort out where you are.

1. The Money Side Makes Sense

Let’s start with the practical piece.

Hiring a bookkeeper costs money. We can absolutely talk about ROI and long-term benefits (and I’m happy to, at another time), but at its most basic level, this is an ongoing business expense. Dollars leave your account each month. That part is real.

When the timing is right, that expense feels intentional and strategic, not like you’re crossing your fingers that the client check comes in on time so you can cover the cost.

To be sure, that doesn’t mean your business has to be wildly profitable. We work with business owners who are in growth phases, investing heavily in upgrades, or still ramping up. Profitability and “this investment feels solid” are not the same thing.

The question is simpler than most people make it:

Can your business absorb this cost without it creating strain?

If the answer is “yes” — even if you’re still building — that’s useful information.

If the answer is “not yet,” that’s useful too. It may just mean moving “hire a bookkeeper” from the to-do list to the “goals for next year” list.

2. You Want (or Need) Bookkeeping Off Your Plate

Sometimes the tipping point isn’t about money. It’s about how you want to spend your attention and spoons.

It could be that:

  • You don’t enjoy doing your bookkeeping and never have.

  • You can do it, but it eats up time you’d rather spend serving clients, refining offers, or, you know, not working (radical, we know!).

  • You don’t know how to use your bookkeeping software and have no desire to become proficient.

  • You kinda-sorta know what you’re doing, but you’re never actually confident about it.

  • Being up-close-and-personal with every.single.transaction feels tedious, overwhelming, or like a poor use of your spoons.

For some business owners, it’s about energy.
For others, it’s about leverage.

Either way, if bookkeeping is consistently pulling attention away from higher-level work or costing you more in energy than it’s worth, that’s something to add to the equation.

3. Keeping Up Is Getting Harder Than It Used To Be

Bookkeeping is important. It’s rarely urgent.

Which makes it extremely easy to push off to “later”.

A few weeks behind turns into a month, then a quarter, and the further behind you get, the heavier it feels to log in and start. Pretty soon, you’re having a “wait, how did this happen again” moment. (We’ve all been there, whether it’s with bookkeeping or, say, having a sink full of dishes and no clean forks.)

There’s a difference between “behind this month” and “always behind.” If your books are consistently lagging behind your actual business activity, that’s a signal. Not a crisis. Just a signal.

And that signal may be saying that your business has outgrown the “I’ll get to it when I get to it” phase.

4. You’d Like to Stop Wondering If You “Did It Right”

There are plenty of ”myriad of right ways to do things” areas in business.

Bookkeeping isn’t one of them.

Income and expenses need to be recorded accurately. Accounts need to be reconciled. Reports need to reflect reality.

You don’t need to live in fear of the IRS to recognize that accuracy matters.

But if you find yourself thinking:

  • “I’m pretty sure this is right?”

  • “I hope I categorized that correctly”

  • “I’ll deal with it if it becomes a problem”

that’s a lot of question marks to be working around. And over time, question marks and “pretty sure” can get tiring.

To be sure, having clean, accurate books doesn’t guarantee you’ll never get a letter in the mail. But it does mean that if you do, you’re not scrambling or second-guessing your own records.

There’s a certain steadiness that comes from knowing your numbers are solid.

So… Is It Time?

There isn’t a universal milestone where every business “should” hire a bookkeeper.

But there is a time when it starts to feel like a practical, helpful reallocation of energy.

If you saw yourself in several of these points, that’s worth paying attention to.

It may mean that bringing in bookkeeping support would free up time, stability, and mental space in a way that very much aligns with where your business is now.

And if you read through this thinking, “Not yet, but I can see it coming,” that’s useful too. It simply means you’re aware of the shift and can keep an eye out for when it arrives.

Either way, the goal is alignment — between your role, your energy, and what feels sustainable.

If you’re curious what bookkeeping support could look like for your specific business, you’re welcome to [reach out here].