Less going in circles. More independence. LessAccounting gives you a dedicated bookkeeper who learns your business and keeps your books current every month, with every client payment and business expense recorded, so quarterly taxes and tax season stop being a guessing game.
- Dedicated bookkeeper
- QuickBooks Online included
- No long-term contract
Bookkeeping for small businesses since 2007.
By Chris May · Updated October 2026
(The live H1, “Less going in circles. More independence.”, becomes the benefit line.)
LessAccounting provides done-for-you monthly bookkeeping for independent contractors: a dedicated bookkeeper who learns your business records your client payments and business expenses, reconciles your bank and card accounts, keeps business and personal spending apart, and sends a monthly report that shows your profit so you can plan estimated taxes. Plans start at $299 per month, scoped on a free demo call.
Why bookkeeping gets messy when you work for yourself
No one withholds your taxes
As a contractor, nobody takes taxes out of your payments. The IRS expects estimated tax payments if you’ll owe $1,000 or more when you file, spread over four payment periods (IRS: estimated taxes). You can only estimate well if you know your profit month by month.
Self-employment tax on top of income tax
Net earnings of $400 or more from self-employment trigger self-employment tax: 15.3% for Social Security and Medicare, per the IRS self-employment tax page. Every legitimate business expense you record lowers the profit that tax is calculated on.
Personal and business money in one account
One checking account and one card for everything is a common setup, and the hardest to untangle at tax time. Separating them is step one (see how to stop mixing business and personal finances).
1099s that don’t match your records
Clients send Forms 1099-NEC in January, and payment platforms may send their own forms. The totals rarely match your bank deposits one-to-one, because of timing, fees and refunds. And income is taxable even when no form arrives, as the IRS gig economy tax center points out.
Irregular income
A big project in March and nothing in April is normal for contractors. Without current books, it’s hard to tell a slow month from a real problem, or to know how much you can safely pay yourself.
Deductions you can’t prove
Home office, equipment, software, mileage, travel: deductions only hold up if the expense is recorded and the receipt can be found. Rebuilding a year from bank statements in April is how deductions get missed.
What we handle every month for independent contractors
- Bank and credit card reconciliation, every account matched to statements
- Client payments recorded by client, including payment-platform deposits net of fees, with the fees recorded as expenses
- Business expenses categorized in consistent categories your tax preparer can work from
- Business vs. personal transactions separated and flagged for you to confirm
- A monthly profit report you can use to size your estimated tax payments
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✔ Year-end, CPA-ready books so your tax preparer works from clean numbers
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✔ Invoicing support on Growth (up to 10 invoices/month) and Business Pro (up to 20)
- A dedicated bookkeeper who learns your business, and whom you can reach directly
- QuickBooks Online included in every plan
Not in the monthly plan: payroll and tax preparation are separate services, quoted independently (payroll by number of employees, tax prep after a review of your last two years of returns). Catching up past months is a separate project too (see How it works).
How it works
- Book a call Tell us how you get paid (direct clients, platforms, agencies) and which accounts you use. We scope your plan on that free demo call.
- Onboarding We connect your accounts and set up categories that match how you file. If your books are behind, catch-up isn’t part of the monthly plan: it’s a separate project, priced by how many months behind your books are (see the bookkeeping cleanup checklist). Once you’re current, you move straight into your monthly plan.
- Monthly close Every month we record income and expenses and reconcile every account. Books are ready within 15 business days of receiving your documents.
- Reports and check-ins You get your monthly report with year-to-date profit, in time for each estimated tax payment.
The Contractor’s Quarterly Tax-Ready Routine
A monthly and quarterly routine that keeps your books ready for estimated taxes. Print it, pin it, or let us run it for you.
The Contractor’s Quarterly Tax-Ready Routine
Monthly habits plus four quarterly checks, from LessAccounting
Every month
- Every client payment recorded by client, with platform fees as expenses
- Business card and bank account reconciled to statements
- Personal charges on business accounts flagged and moved out
- Receipts attached for every expense you plan to deduct
- Your agreed tax set-aside moved to a separate savings account
Before each estimated payment
- Year-to-date profit pulled from reconciled books, not your bank balance
- Profit sent to your tax preparer to size the payment
- Payment made and recorded, with the confirmation saved
- Big one-off income or expenses noted for next quarter’s estimate
Doing it yourself, a spreadsheet, or LessAccounting?
| DIY in a spreadsheet or app | Generic bookkeeper | LessAccounting for contractors | |
|---|---|---|---|
| Your time | Evenings, usually in April | Less | A dedicated bookkeeper does the monthly work |
| Estimated taxes | Guesswork from last year | Depends on how current the books are | Monthly profit report before each payment |
| Business vs. personal | Easy to blur | Varies | Separated and flagged monthly |
| 1099s received | Checked (maybe) at tax time | Varies | Income recorded every month, ready to compare with your 1099s |
| Receipts and deductions | Hunted down at year-end | Varies | Recorded as they happen |
| Price | App subscription + your time | Hourly or flat, varies | Plans from $299/mo (scoped on a demo call), QuickBooks Online included, no long-term contract |
Simple monthly pricing, starting at $299
| Plan | Price | Typically built for | Which contractor it fits |
|---|---|---|---|
| Simple | From $299/mo | Under $300K revenue, ~2 bank accounts | Solo contractors with simple books and one or two business bank accounts |
| Growth (most popular) | From $449/mo | $300K–$1M, ~3–4 bank accounts, AR support up to 10 invoices/mo | Contractors with several bank accounts, steady invoicing or a subcontractor or two |
| Business Pro | From $699/mo | $1M+, up to ~10 bank accounts, quarterly consultations | Contractors who’ve grown into a small firm |
| Custom | Custom quote | Over $5M or multiple entities | – |
Plans start at $299, $449 and $699 per month. We scope your plan on a free demo call based on your revenue, the number of bank accounts you use and your average monthly transactions, and if the work grows beyond that scope, you move up a tier. Every plan includes a dedicated bookkeeper who learns your business and QuickBooks Online. Payroll, tax preparation and catch-up work are quoted separately.
Client story: read Kumano Adventures case study to see how a growing business moved its bookkeeping to LessAccounting.
Bookkeeping for independent contractors: FAQs
Do independent contractors need a bookkeeper?
Not every contractor does, but most benefit once they have regular clients and more than a handful of transactions a month. A bookkeeper keeps income and expenses recorded and reconciled, so you know your real profit, can size estimated tax payments, and hand your tax preparer clean books. The alternative is rebuilding a year from bank statements in April, which is when deductions get missed and estimated payments turn out to be wrong.
How do independent contractors pay taxes?
Independent contractors usually pay income tax and self-employment tax through estimated quarterly payments, because no employer withholds them. The IRS expects estimated payments if you expect to owe $1,000 or more when you file, divided into four payment periods. Self-employment tax covers Social Security and Medicare at 15.3% of net earnings and applies once net earnings reach $400. Your tax preparer calculates the amounts; current books give them accurate numbers to work from.
Do I need a separate business bank account as a contractor?
It isn’t legally required for a sole proprietor, but it’s the single most useful habit for clean books. A dedicated business checking account and card mean every transaction on those statements is business by default, which makes categorizing, reconciling and proving deductions far easier. If you operate as an LLC or corporation, keeping business money separate also helps protect the legal separation between you and the business. Ask your attorney or CPA about your situation.
What should I do if a 1099 doesn’t match my records?
First, check timing and fees: a client may report a payment in the year they sent it while you received it in January, and payment platforms may report gross amounts before fees and refunds. If the form is still wrong, ask the payer for a corrected form. Either way, report all the income you actually earned, because income is taxable whether or not you receive a form. Your bookkeeper can match each 1099 to recorded deposits.
What expenses can independent contractors deduct?
Generally, ordinary and necessary business expenses: things like software and subscriptions, equipment, a portion of your phone and internet, business travel, professional fees, insurance and, if you qualify, a home office. Personal expenses aren’t deductible, and mixed-use items need a reasonable business share. The key is records: an expense you can’t document is hard to defend. See our home office deduction guide, and confirm specific deductions with your tax preparer.
How much does a bookkeeper cost for an independent contractor?
LessAccounting’s plans start at $299, $449 and $699 per month. We scope your plan on a free demo call based on your revenue, the number of bank accounts you use and your average monthly transactions; Simple typically fits businesses under $300K in revenue. If the work grows beyond that scope, you move up a tier. Every plan includes a dedicated bookkeeper who learns your business, monthly reconciliation, a monthly reporting package and QuickBooks Online, with no long-term contract. Catch-up for past months, payroll and tax prep are quoted separately.
Should a contractor use cash or accrual accounting?
Most solo contractors use the cash method: income is recorded when a client pays, expenses when you pay them. It matches how you file as a sole proprietor and is simple to keep. Accrual accounting, which records income when you invoice and expenses when you incur them, becomes useful when you carry large unpaid invoices or want a truer month-by-month picture. Choose with your tax preparer; your bookkeeper keeps the books consistent with that choice.
I’m a year behind on my books. Can you catch me up?
Yes. Catch-up is a common way contractors start with us: one year of client payments, card charges and receipts that never got sorted. Catch-up isn’t part of the monthly plan: it’s a separate project, priced by how many months behind your books are, and most projects are completed in two to six weeks. You end up with reconciled, categorized books your tax preparer can file from, and then a monthly plan keeps you current.
Get back to the work you’re actually paid for
Book a call and we’ll show you what your books would look like every month.
Sources
- IRS: estimated taxes (irs.gov)
- IRS self-employment tax page (irs.gov)
- IRS gig economy tax center (irs.gov)