Cadet
Regular price$29$14.50 / month
Founding price for your first 12 months
1 seat included
- Public proposal approval & signing
- Deposit on acceptance
- Proposal-to-invoice conversion
- Billable time tracking
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Getting paid
The freelancer tax calendar: the dates that decide your year.
Freelance taxes are a calendar problem before they are a math problem. Know the four quarterly dates, the annual deadlines, and the small weekly habit that makes all of it boring.
Reviewed
In short
In the US, freelancers pay estimated taxes quarterly — mid-April, mid-June, mid-September, and mid-January — and file annually in mid-April. The calendar is the easy part; the hard part is having organized records when each date arrives, which is a weekly expense habit, not an April project.
The four quarterly estimated dates
Self-employed workers generally pay estimated tax four times a year. Mark these and treat them as fixed appointments:
- April 15 — payment for January–March income
- June 15 — payment for April–May income
- September 15 — payment for June–August income
- January 15 (next year) — payment for September–December income
The annual rhythm
The annual return is due mid-April (or October with an extension). An extension moves the paperwork, not the payment — the estimated amount is still due in April. Put both dates on the calendar a year ahead so nothing depends on memory.
The weekly 15-minute habit
Taxes feel hard when records are rebuilt in April. They feel easy when the record is continuous:
- Log every expense weekly, with the receipt attached
- Categorize as you go — software, travel, home office, contractors
- Reconcile invoice status: paid, open, overdue
- Set aside a fixed share of each payment for taxes in a separate account
Keep the records where the money already lives
Expenses are easiest when they live next to invoices and clients, not in a shoebox. Workspace369 tracks expenses beside invoices, payments, and reporting, with files attached — so quarterly estimates pull from actuals instead of a weekend of reconstruction. Note: this is an operations guide, not tax advice — confirm your situation with a tax professional.
FAQ
Common questions
Do all freelancers pay quarterly estimated taxes?
Most US self-employed workers do once they expect to owe above a threshold at filing. The amounts depend on your income and deductions — a tax professional can size your payments; the calendar dates above are the fixed part.
What happens if I miss a quarterly date?
Penalties can apply for underpayment, scaled to how much was underpaid and for how long. Catching up promptly and setting the remaining dates as calendar events limits the damage.
How much should I set aside from each payment?
A common rule of thumb is 25–30% of each payment, moved to a separate account the day it arrives. Your real rate depends on income, state, and deductions — worth one session with an accountant to calibrate.
Plans for freelancers
Pick the plan your work needs today.
Client records, proposals, invoices, online payments, time tracking and intake forms are on every plan. Upgrade when your work needs calls, texts or more.Voyager
Regular price$74$37 / month
Founding price for your first 12 months
2 seats included
Everything in Cadet, plus
- SMS messaging
- Voice & voicemail
- Shared inbox
- Missed-call text back
- No-answer forwarding
Specialist
Regular price$149$74.50 / month
Founding price for your first 12 months
10 seats included
Everything in Voyager, plus
- Online booking
- Expense tracking
- Payment plans
- Inventory tracking
Founding member offer: 50% off your first 12 months, for the first 100 customers who join by Oct 31. 14-day trial with a card, USD monthly billing. Compare all plans.
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