How to time your first Social Security check
Q: I plan to retire in August at my full retirement age of 66 and 2 months. How soon should I let Social Security know that I want to begin claiming benefits to ensure that I receive my first check on time?
A: Let’s be clear about what “on time” means because even if you give Social Security ample notice, you won’t get paid in August.
Social Security pays one month in arrears, so your first payment, which is for August, won’t arrive until sometime in September.
With that in mind, you should file your application at least 60 days before the month that you plan to retire, said Jim Blair, a former district manager for Social Security and currently co-owner of Premier Social Security Consulting in Cincinnati.
You can apply for Social Security benefits as early as four months before that point, he said.
If you expect to rely heavily on Social Security for your day-to-day expenses or will face big bills the first month you retire, the delay in payment could hurt.
“People need to plan ahead for that,” Blair said. “You just need to make sure you have enough money to get you to that point from when you retire until you get that first Social Security check, which may be a month or month and a half later.”
Q: I’ve heard about tax harvesting and the 30-day wash-sale rule. How does the IRS define “days?” Are these business days or calendar days?
A: The IRS defines them as calendar days, and the 30-day rule applies before and after the date the investment is sold.
So it’s really over 60 calendar days that you cannot repurchase a security sold at a loss if you also want to claim the deduction on your taxes.
Q: How do I report my $300 donation to charity in 2020 if I don’t file an itemized tax return?
A: Nonitemizers can write off up to $300 of charitable cash contributions on line 10b of the 2020 Form 1040.
This means filers can take the standard deduction and a deduction for up to $300 of cash donations paid to a 501(c) (3) organization.
The $300 cap applies whether you file a single, head-of-household or joint return. (Note that for 2021 returns only, the ceiling is $600 for couples who file jointly.)