It depends. To find the answer, let's answer some questions with more questions.
Are You Currently Keeping Your Books?
Are you currently maintaining your own books? Do you love it? Can you not even begin to describe the pure, unadulterated joy you feel when you get the opportunity to sit down and get down and dirty with QuickBooks? If you answered yes to those questions, you are a sicker than we are and hell yeah, you should keep doing your own books.
Have you done this before?
If you've ever learned anything new, you know there is usually a learning curve. Sometimes simple things take you longer because you haven't done them enough times to anticipate mistakes. Sometimes you make a simple error that sends you flying down the Google-search rabbit hole, where time warps and hours fly by in what feels like minutes. If you have the time and energy to put towards learning this new skill set, do it. It's an invaluable exercise and you'll learn a lot about your business and your spending. You'll develop systems and you'll get better with time.
Do you have more time and energy than you do paying customers?
Well, do ya? If you say yes, then I'm going to go out a limb here and say, do your own books!
If you're so busy with work, you might be ripe for hiring a bookkeeper. At a certain point, it makes more sense for you to focus on running your business and less time on the day-to-day stuff that a bookkeeper can help you with. For example, there are plenty of business owners who are too busy to read this to know they should probably be hiring a bookkeeper.
Do you hate it so much that you want to poke your own eyes out?
Well, that's gnarly and you should probably get a bookkeeper. BUT and there is a big, juicy BUT (hehe) - it has to make sense from a financial standpoint. The time and energy that you would have put into keeping your books must free you up so you can focus on running your business, earning revenue and helping your customers. Otherwise, from a financial standpoint, I don't think you can justify hiring a bookkeeper.
Do you want to scale and grow your business?
If the answer is yes, then you should absolutely considering hiring and paying for bookkeeping services.