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I set a reminder in Google Calendar for the 7th of every month to pay estimated tax on the money I earned the previous month.
I wait until it’s time to pay.
I figure out how much I owe.
I go to my bank and download the transactions for the past month.
I select ‘Custom’ for the Date Range and set it to the first until the last day of the previous month.
I select ‘Other’ under the ‘Show’ dropdown to narrow it to non-Visa-debit-card activity.
I have Claude open on the left half of my screen and my bank history on the right half of my screen and I just copy in the deposits and ask Claude to add them up. Double-check each deposit to make sure it should be included (e.g. a reversed transfer should not be included).
I multiply that by 0.15 to get the self-employment tax I owe.
I pay it.
I go to the IRS ‘Make a Payment’ page.
Verify Identity
I open a previous tax return in Dropbox to see what address I used and copy it exactly.
I record the payment amount and confirmation number in my Google sheet for tax payments.
I confirm the payment was received.
…? Maybe I should check this the following month?
I go to https://www.irs.gov/your-account
After signing in, scroll down the page to look for the ‘Payments’ section, then click ‘View Payment Activity’.
If I see a payment listed as ‘Pending’ for too long, I call the IRS.
1-800-829-1040