Dial In on the Retirement Timeline and Prepare
Anytime you deal with government agencies, things take time. Retirement is no different. Many new retirees are caught off guard when they realize how long it takes to get the first check. Let’s get into it.
When Can I File for Retirement?
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You can file for Social Security as early as 4 months before your 62nd birthday. Over 65% of applicants file online at SSA.gov. You can file via phone by calling the national line at 1-800-772-1213 as well.
Another option is to file in person at your local Social Security Administration (SSA) office. Please know that SSA offices schedule appointments for two to four weeks out. You can call the national line at 1-800-772-1213 or contact your local office directly to make an appointment.
For the rest of this article, we are going to use a fictional example of ‘Jennifer’ born on October 15th. If Jennifer wants to file in person for early retirement at age 62, she should call her SSA local office around May 15th to make an appointment on or after June 15th. Don’t go into the office earlier than 4 months before your 62nd birthday, otherwise they will turn you away and tell you to reschedule.
Applying for Social Security
Go online to SSA.gov to make sure you are eligible and to get an idea of your estimated monthly check. Once you’ve determined you’re eligible for Social Security and the timing is right, the next step is getting ready to apply for benefits.
Before you start your application, make sure you have the following information at hand to help prevent any delay in processing.
Birth certificate, or another official record to prove your age
Your Social Security card or another record showing your number
Proof of U.S. citizenship or lawful alien status, if you were not born in the United States
Marriage and/or divorce documents, if you’re applying for spousal or divorced spouse benefits
Work and earnings history, this means your most recent W-2 or tax returns if you’re self-employed
If you don’t have some of these documents available, don’t panic! You can still apply and provide the missing paperwork later. The SSA may even be able to help you get them.
How Soon Do I Get My First Check?
Social Security is paid to you in arrears. You have to be retired for an entire month before you get paid the following month. And the day you get paid depends on what day of the month your birthday falls on. Payments are typically distributed on specific Wednesdays based on your birth date. Birthdays that fall on the 1st-10th are paid on the second Wednesday of the month. Birthdays on the 11th - 20th are paid on the third Wednesday of the month. Birthdays on the 21st - 31st are paid on the fourth Wednesday of the month.
Example: Jennifer turns 62 on October 15th and quits her job. She makes an appointment to file for Social Security the following week. She would receive nothing for the last half of October because the rules state that you have to be of minimum age and retired for the entire month to receive payment. Jennifer would be eligible to receive payment for November, but would be paid out the following month. Because her birthday is on the 15th, she is looking for a direct deposit on the third Wednesday of the month. In 2026, this direct deposit would come in on December 16th, two months after her 62nd birthday.
Knowing the actual start up timeline is critical because many households are paycheck to paycheck. In this scenario you would need up to two months of financial reserves in place to successfully make the leap to Social Security.
There is a workaround but it is less sexy than the ‘Take This Job and Shove It’ Johnny Paycheck scenario in your head where you quit corporate America and retire on the same day. If you opt for early retirement, there are a set of rules called Earned Income Limits that allow you collect Social Security and continue working at the same time within limits. For 2026, the earned income limit for early retirees is $24,480. The SSA will deduct $1 from future benefits for every $2 you earn above this limit. If you retire mid-year like Jennifer did, Social Security applies a Special Earnings Limit Rule. In your initial year of retirement only, the SSA applies a monthly earnings test instead of an annual limit. In 2026, the monthly exempt amount is $2,040. Jennifer can get a full Social Security benefit for any whole month she is retired and earnings are below the monthly limit.
If Jennifer was stressed about not having two months of financial reserves in place, she could put a plan in place like this. She turns 62 on October 15 and files for Social Security the following week. Then she continues her job for the rest of October. She isn’t getting a Social Security check for October because she filed mid-month, so she can earn however much she wants to in that month. Now in November, she can only work up to $2040 in gross wages without any penalty. If Jennifer makes $48,960 a year, she can work the first two weeks of November and then quit without penalty. Now she only has to wait one month until her Social Security payment hits her account. It’s still not perfect, but it cut the wait time in half.
How Can You Prepare in the Months Leading Up to Retirement?
How deep is your pantry? FAWA recommends you stock 8-12 weeks of food in your freezer and pantry while you are still working - a Retirement Starter Kit. With the price of groceries these days, it is important to shop the sales and do it slowly over time. Making the decision to retire is just as much an emotional one as it is financial. Having your pantry well stocked helps get you through the initial wait time and will calm any fears you may have about government glitches or delay of payments. You may have to juggle obligations during this time but at least you know you won’t go hungry.
FAWA has created a starter list of items for you to consider. Don’t forget to stock up on personal care items, pet care, and paper products. Seeing your starter kit begin to stack up can be exciting as it becomes a tangible, real sign that your retirement is around the corner.
Another critical aspect is to take a close look at your monthly budget. Make sure you have a plan to pay down your debt as much as possible prior to switching to a fixed income. Many of us may need to find an enjoyable part-time job or side hustle that will help to make ends meet. Making these preparations in the months leading up to your 62nd birthday will allow you to sleep better at night.
Don’t Forget About Medicare
Note: Get ready for a bunch of alphabet soup acronyms. Government loves acronyms.
As a retiree, you are eligible for Medicare starting at age 65. Your Initial Enrollment Period (IEP) for Medicare is a 7-month window that begins 3 months before the month you turn 65, includes your birth month, and ends 3 months after. For Jennifer, her 3-month window before her birthday would be July, August, and September. The enrollment window includes October as her birthday is October 15th. It also includes the 3-month window after her birthday during November, December, and January.
If Jennifer signs up in July, August or September, her Medicare coverage would start for the month she turns 65 which is October. If she enrolls in October, November, December, or January, her coverage will start the month following her application.
If Jennifer forgot about her 7-month Initial Enrollment Period altogether, she may have to wait to sign up during a General Enrollment Period (GEP) that runs from January 1 to March 31 each year. Jennifer may also have to pay a monthly late enrollment penalty for as long as she has Part B coverage. The penalty goes up the longer she waits. She may also have to pay a penalty for Part A premium. Learn more about late enrollment penalties here.
The odds of Jennifer actually forgetting about her Medicare enrollment date are slim. Once she enrolls for Social Security, she will begin to receive an onslaught of offers in her mailbox from very interested Medicare Sales Agents.
The Annual Enrollment Period (AEP) for Medicare runs from October 15 to December 7 each year. You can change your Medicare Advantage or prescription drug coverage, with changes starting January 1 during this time. If you watch cable TV, you will see many, many ads for Medicare annual enrollment.
There are other times of the year that you can make changes to your coverage. A Special Enrollment Period (SEP) can be triggered by specific life events, such as losing employer health coverage. You typically have an 8-month window after employer coverage ends to sign up for Part B without a penalty. A SEP can also be triggered if you move outside of the service area that your current health plan is in.
Whew. That was a lot.
Alot of pre-retirees look at saving money and investments as an activity done prior to retiring. If you believe you may have some extra cash on hand in the first few years after you retire, learn about investments during retirement.
