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When do you deposit check?

I have seen that too. You don't have option of holding a check a couple of weeks before year end.

On a cash basis, the period starts Jan 1 and ends 12/31.

If it is direct deposit on a cash basis. It is income when it hits the business account. Same way on holding a check until Jan 1st of next year. It is not income until it hits the account.

Check could be dated 12/15/2025. Check deposited 01/01/2026. On a cash basis, that is 2026 income.
What if the client sends you a 1099?
 
I bill my clients - private and bank - and they pay after they get the report. It has been 10 years or so since I have got stiffed for a fee. Huge jobs I do require a retainer, otherwise I generally know who I am dealing with.
 
I bill my clients - private and bank - and they pay after they get the report. It has been 10 years or so since I have got stiffed for a fee. Huge jobs I do require a retainer, otherwise I generally know who I am dealing with.
I like that. Let private party know it's a retainer fee. Sounds better.
 
Paypal, Venmo, Zelle, Apple Cash or CashApp directly after inspecting. No typing until fee is paid then they get the report 2 to 4 business days later.
 
If you do much private work, you'd better get used to accepting payments via "Apps". If you don't, you will lose business to those who do.

Doubtful. I do a ton of private work and everyone pays by check. Most bank apps have a method to pay anyone by their phone number, but it's still technically a check.

As for when to cash a private party check....right away. I will usually start on a report depending how busy I am at the time, but do not deliver until their check clears. Which is another reason to avoid apps. They're easier to chargeback than a check. I think Zelle may be one of the better ones, but avoid paypal and any of the others tied to it.
 
Does that work for expenses?
If I date an expense check 12/31 in 2026 and send it out to be paid in 2026?
Yes on a cash basis. If you pay for it in 2025, it is 2025 expense. If you pay for it in 2026, it is a 2026 expense on a "cash basis". These are IRS rules. I know dang well you have an accountant.

You write a check Dec 31 2025, it is a 2025 business expense on a "cash basis" if that is how you do your taxes.

You pay for it Jan 1st, 2026, it is 2026 business expense on a cash basis.
 
Doubtful. I do a ton of private work and everyone pays by check. Most bank apps have a method to pay anyone by their phone number, but it's still technically a check.

As for when to cash a private party check....right away. I will usually start on a report depending how busy I am at the time, but do not deliver until their check clears. Which is another reason to avoid apps. They're easier to chargeback than a check. I think Zelle may be one of the better ones, but avoid paypal and any of the others tied to it.
I also do a ton private work, and never had a chargeback via "app". Yet. The advantage to the consumer running on fumes is the ability to put it on their credit card instead of having to actually withdraw cash from their bank account. You are correct about Zelle, however. It's the one endorsed by most lending institutions.
 
What if the client sends you a 1099?
The 1099 is different story on a cash basis. The 1099 is automatically counted as income because the 1099 goes to IRS. Sometimes a client don't send one. I know my income. I count it as other income if I don't get a 1099.
 
Sometimes I wish people paid me in cash. LOL
 
I heard some dude got paid $50,000 cash doing border control. Probably a hoax story
 
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