When should I hire a bookkeeper or CPA instead of doing it myself?

Doing your own books is fine when you're a low-volume sole proprietor with simple income and a handful of expenses — software plus a dedicated business account may be enough. Consider a bookkeeper once transactions pile up, you're behind on categorizing, or you can't quickly answer "how much did I make this month?" — bookkeeping is ongoing recordkeeping. Bring in a CPA or tax pro when your situation gets layered: an S-corp election, employees or contractors, multi-state sales tax, large equipment purchases, the QBI phase-out, or simply when your time is worth more than the fee. A common pattern is a bookkeeper handling the monthly records and a CPA handling tax strategy and the return. The cost is usually deductible, and good advice often pays for itself through cleaner books and missed-deduction recovery. If taxes cause you stress or surprises, that's your signal.