The honest answer is probably sooner than you think. Most business owners wait until bookkeeping becomes a crisis before getting help. By then, they’re paying for cleanup on top of ongoing services and making decisions with unreliable numbers.

Here are the practical signs it’s time.

You’re spending hours you don’t have. If bookkeeping takes more than a few hours each month and you’re billing $50 or more per hour for your actual work, the math doesn’t favor DIY. Those hours spent categorizing transactions and reconciling accounts could go toward clients or projects that generate revenue.

You’re falling behind. Bank statements pile up. Receipts sit in a drawer. You reconcile quarterly instead of monthly, or not at all. Falling behind isn’t just an organization problem. It means you’re running your business without knowing your real financial position.

Your business got more complicated. You hired employees. You added a second bank account or credit card. You started tracking jobs or projects separately. You began selling in multiple states and dealing with sales tax. Each layer of complexity makes accurate bookkeeping harder to do yourself and increases the chances of expensive mistakes.

You don’t trust your numbers. You pull up a profit and loss statement and something seems off, but you’re not sure what. You can’t say confidently whether last month was profitable. You don’t know which services or products make money and which don’t. When the numbers feel unreliable, you stop using them to make decisions.

Tax time is expensive and stressful. Your accountant charges extra to sort through a year of messy records. You scramble in March to find receipts and figure out what various transactions were. You suspect you’re missing deductions because your books don’t capture everything properly.

You’ve made mistakes that cost money. You paid a bill twice. You forgot to invoice a customer. You missed a quarterly tax payment. You categorized personal expenses as business or vice versa. Small errors compound into real money over time.

The threshold isn’t a specific revenue number or transaction count. It’s the point where not having professional bookkeeping costs you more than having it. That might be money you’re losing to errors, deductions you’re missing, time you could spend on billable work, or decisions you’re making with bad information.

For most small businesses, that point comes somewhere between $100,000 and $250,000 in annual revenue, often when they hire their first employee or take on work that requires job costing. But it varies. A contractor with 200 transactions per month and three subcontractors needs help sooner than a consultant with 20 transactions and no payables.

If you’re questioning whether it’s time, it probably is. The cost of small business bookkeeping services is usually less than business owners expect, and it’s almost always less than what messy books cost you in missed deductions, wasted time, and poor decisions.