For the Mary Kay business, Social Security looks at your profit (revenue minus expenses) as reported on your Schedule C. This is considered self-employment income. For 2025, if you're receiving benefits before FRA, you'll be subject to the earnings limit (approximately $22,320 for the year). One important detail: Self-employment income counts when you receive it, not when you earn it. So if clients pay you in December 2025, that counts for 2025 even if the work was for January 2026. Regarding when to apply, the optimal time is 3 months before you want benefits to begin. You can specify a start date in your application, so you can apply before you retire and have benefits begin afterward.

I'm in a similar boat - turning 65 next year and trying to navigate all these decisions! One thing I learned from my financial advisor is to run the break-even analysis between taking benefits at 65 vs waiting until FRA. In my case, if I live past age 78, I'll come out ahead by waiting until 67. But everyone's situation is different based on health, other income sources, and financial needs. For your vacation payout, definitely factor that into your calculations for the year you retire. I'm planning to take my vacation time as actual time off before retiring instead of a lump sum payout to avoid the earnings limit issue entirely. Also, since you mentioned feeling lost about timing - the SSA website has a retirement estimator tool that can help you see exactly how much your monthly benefit would be at different claiming ages. It really helped me visualize the trade-offs!

One other thing nobody mentioned - if 2025 is your first year of retirement, you can use the monthly earnings test instead of the annual one. This means after you officially retire, you can make as much as you want for the remainder of the year before retirement, and then be limited to $1,860/month ($22,320 ÷ 12) for any month after retirement. This is a big advantage in the first year! After 2025, you'd be subject to the annual limit only.

Just wanted to add one more important detail that might help - when you do contact Social Security to report your retirement, be very specific about your work end date versus payment dates. I've found it helpful to have three key pieces of information ready: (1) your official last day of work, (2) what earnings period your final paycheck covers, and (3) the exact amounts for regular wages versus any vacation/bonus payouts. SSA representatives deal with this timing issue constantly, but having all the details organized makes the conversation much smoother. Also, keep copies of everything your employer gives you about the payments - you might need to reference it later if there are any questions about your earnings record.

my mom died last year too and i had same problem!! waited forever for her ss-1099 then gave up and did taxes without it. big mistake!! got a letter from irs 6 months later saying we underpaid taxes bc didn't report all her income!! had to file amended return and pay penalty and interest!! dont do what i did lol. definitely wait for that form or get an official replacement!!

hey just checking in - did you end up getting your dads 1099 yet? mine just came yesterday for my mom so maybe yours is on the way

dont forget about checking if your state has any widow assistance programs too! some states have emergency funds or special programs. worth looking into while waiting for SS benefits

I'm so sorry you're facing this difficult situation. As someone who works with Social Security cases, I want to add a few important points that might help with your planning: First, make sure to verify that your marriage duration meets SSA requirements - you need to have been married for at least 9 months before your passing for your wife to qualify for survivor benefits (there are some exceptions for accidental death). Second, consider having your wife create her my Social Security account online NOW if she hasn't already. This will make it much easier for her to track benefits and apply when the time comes. Also, if your wife decides to work more hours to compensate for lost income during that 8-year gap, remind her that higher earnings now could increase her own Social Security retirement benefit later. The SSA uses your highest 35 years of earnings, so additional work years might replace some lower-earning years in her calculation. Finally, don't overlook potential benefits from other sources during the gap - things like your employer's life insurance, 401k survivor benefits, or even COBRA health insurance continuation might help bridge that period until she can claim Social Security survivor benefits. Wishing you and your wife strength during this challenging time.

my sil got in big trouble with SS cuz she went over the limit and didnt tell them. they made her pay back thousands!! make sure u report if u earn more than u think

Don't forget to consider your health insurance situation too! If you're getting health benefits through your part-time job, that might factor into your decision about when to claim. Medicare doesn't start until 65, so if you need those employer benefits to bridge the gap, that could influence your timing. Also, since you mentioned being overwhelmed - the SSA website has a really helpful retirement estimator tool that lets you plug in different scenarios to see how your monthly payments would differ at 62, 64, FRA, or even waiting until 70. It helped me visualize the long-term impact much better than just reading about percentages!