How do you know if doing your own books is working?
Look at last month. If every bank and card account was reconciled to its statement, and you can say roughly what came in, what went out and who still owes you, the books are working. IRS Publication 583 tells businesses to reconcile the checking account each month, so that's a fair yardstick for an owner as much as for a bookkeeper.
The second question is what it cost you to get there. Two hours on a Tuesday night is one thing. Most of a Sunday, every month, plus the low dread of a pile you haven't opened, is another. Neither answer is wrong. It just points to a different decision.
Which situation are you in?
Find the row closest to where your Bloomfield business is today, then read the section under it.
| Situation | What it looks like | What to do |
|---|---|---|
| Current and quick | Every account reconciled last month in a few hours of work | Keep doing your own books and recheck in a quarter |
| Current but costly | The books are right but they take evenings or weekends you resent | Hand off one piece, usually the reconciliations |
| Months behind | Unopened statements, an uncategorized pile, no reconciliation since spring | Catch up first, then decide who keeps the books |
| Growing | Staff on payroll, customer invoices to chase and bills to schedule | Hire a bookkeeper for the whole set of books |
Your books are current and the work is quick
Keep going. There's no bookkeeping reason to hire help for books that already reconcile and that you understand. Set a date each month for the reconciliation and keep the business account separate from your personal one, which Publication 583 also advises. Check again in a quarter, or sooner if you hire someone or add a new account.
Your books are current but they cost you evenings
Hand off the part you dread rather than the whole job. If that's the monthly bank and credit card reconciliations, it's a natural first piece, because it's the step that gets pushed to next week and then the week after. You keep entering sales and paying bills, and someone else makes sure the balances agree each month. If the handoff works, you can add pieces later.
You're months behind
Don't decide yet. Get the books caught up first, starting from the last month you know was right, because whoever keeps them afterwards needs a clean starting point. That's a bookkeeping cleanup and catch-up project. Once the accounts reconcile again, you'll know whether you can keep them that way on your own.
Your business is growing
This is the clearest case for hiring. Staff, customer invoices and scheduled bills all feed the same ledger, and one person keeping the whole of it makes it easier for the reconciliation, the payables and the month's reports to agree with each other. That arrangement is called full-charge bookkeeping. Hand over the work but keep the main login to the software yourself, with your bookkeeper on a separate user.
Start a conversation with Brittany about where your books stand and which part, if any, is worth handing off.
Call (860) 234-7704What changes when you hire your first employee?
The paperwork grows, and so does the cost of a missed month. The CT Department of Labor says all employers of one or more persons, full or part-time, must register online for unemployment insurance. The Department of Revenue Services says an employer required to withhold Connecticut income tax must register for withholding with DRS. The IRS hiring page says every U.S. employer must complete Form I-9 for each person it hires.
CT Paid Leave adds a quarterly job: employers remit the deductions to the CT Paid Leave Authority every quarter, and registration is required even if a payroll provider enrolled the business. A payroll provider runs the checks, but the owner still has to confirm that the provider's reports agree with what left the bank. That kind of checking can sit under payroll support, with the scope agreed with Brittany, and payroll is often where doing your own books stops fitting in an evening.
What should a Bloomfield owner keep, whoever does the books?
Dated records of what the business owns. A trade name in Connecticut is filed with the town clerk where the business is primarily transacted, and Bloomfield's Town Clerk charges $20, cash or check, as its page read in October 2026. Bloomfield's Assessor lists the Town Clerk's records, trade name certificates included, among the sources it uses to discover property. Registering a trade name is one way the Assessor learns a business exists.
Business personal property in Bloomfield is assessed to whoever owns it on October 1. Connecticut's statutes set the declaration's due date at November 1, or the next business day when that falls on a weekend, and an extension has to be requested in writing by that same date. The Assessor decides whether there's good cause to grant one, and the town's personal property brochure names December 15 as the extended date in Bloomfield. Miss the deadline that applies to you and state law adds a 25% penalty to the assessment. The same brochure says equipment still in use must be reported even when it's been fully depreciated, and that selling the business on January 15 still leaves the seller with the July bill.
None of that changes with who keeps the books. What changes is how long the declaration takes. If each equipment purchase was recorded with its date and cost when it happened, the list is one report. If you're in town and want to talk it through, start with Brittany's Bloomfield bookkeeping page.
What does hiring a bookkeeper actually hand off?
Recording, categorizing and reconciling, plus the reports built from them. Brittany works alone from Wethersfield and serves Bloomfield and the rest of her Hartford County service area. Her list runs from full-charge bookkeeping down to single pieces like transaction categorization or expense tracking, and scope is agreed before work begins. What stays with you: decisions, approvals, the main login and anything to do with taxes, which goes to your tax professional.
