Just wanted to add one more consideration that might be relevant to your situation - if you're married, you'll also need to think about how your Medicare enrollment timing affects your spouse's HSA eligibility. If you're both covered under the same employer family plan and you enroll in Medicare Part A, your spouse can still contribute to an HSA as long as they're not Medicare-eligible themselves. However, if your spouse is also approaching 65, you'll want to coordinate your Medicare enrollment decisions to maximize both of your HSA contribution opportunities. My wife and I staggered our Medicare enrollments by a year specifically to extend our HSA contribution period, and it worked out really well for building up our healthcare nest egg.

I went through this exact situation two years ago and want to share what I learned. The key insight that saved me thousands was understanding that Medicare Part A enrollment is NOT automatic at 65 if you're still working - that's a common misconception. You have to actively decline it. Here's what I did: I contacted Social Security about 3 months before my 65th birthday to formally decline Medicare enrollment while I continued working. This allowed me to keep contributing to my HSA for another 2.5 years until I retired at 67.5. During that time, I maxed out my HSA contributions and even did catch-up contributions since I was over 55. One critical thing to watch out for: if you ever filed for Social Security retirement benefits (even if you suspended them), you'll be automatically enrolled in Part A at 65 regardless of your work status. This is a trap that catches many people off guard. My recommendation: Call Social Security soon to clarify your enrollment status and formally document your intention to delay Medicare while working. Get everything in writing! The peace of mind is worth it, and you'll avoid any costly mistakes with your HSA.

This is such a valuable thread for anyone dealing with self-employment and Social Security! I'm approaching 62 and have been putting off claiming benefits partly because of confusion about these rules. One thing I wanted to add based on my research - for those tracking hours, make sure you understand how SSA defines "retirement" for self-employed individuals. It's not just about hours or income alone, but about whether you're "rendering substantial services" to your business. This includes things like: - Making major business decisions - Having regular contact with customers/clients - Supervising employees or managing operations - Being actively involved in day-to-day operations Even if you're under 15 hours per month, if you're still making all the key business decisions and managing client relationships, SSA might still consider you "not retired" for that month. This is especially relevant for consultants and other professionals who might think they can just reduce their hours while maintaining the same level of responsibility. I've been considering restructuring my business to have a partner take over more of the operational decisions while I transition to more of an advisory role. Has anyone here tried something similar? I'm curious if SSA recognizes that kind of gradual transition or if they expect more of a clean break from business involvement. The documentation suggestions everyone has shared are gold - I'm definitely implementing the spreadsheet approach and keeping detailed records of any business structure changes I make.

This entire discussion has been eye-opening! As someone who's been dreading the complexity of coordinating Social Security with my freelance graphic design business, seeing all these detailed experiences and advice is incredibly reassuring. What strikes me most is how proactive everyone recommends being with SSA rather than just hoping for the best. I've been guilty of the "ostrich approach" - just avoiding thinking about it because it seemed so complicated. But reading about people getting hit with $9,400+ overpayment bills really drives home that ignorance isn't bliss when it comes to Social Security. I'm particularly grateful for the clarification on net vs. gross income for the earnings test. As a freelancer, my business expenses are substantial (software subscriptions, equipment, home office, etc.), so knowing that reduces my countable income for SSA purposes is huge. The spreadsheet tracking idea with different categories of work time is brilliant - I never would have thought to track administrative and marketing time separately, but you're absolutely right that it all counts toward the monthly hours. I'm setting up my tracking system this weekend. One follow-up question: for those of you who've actually called SSA to report estimated earnings in advance - do they give you anything in writing confirming the conversation? I'm thinking it might be smart to document these interactions in case there are any disputes later about what was communicated. Thanks again to everyone who shared their experiences. This community is such a valuable resource for navigating these complex issues!

I'm in a very similar situation - turning 66 and 8 months in June 2025 and have been putting off this application because I was so confused about the timing! Reading through all these responses has been incredibly helpful. It sounds like the unanimous advice is to select the month you reach FRA (April in your case), and the payment will automatically come the following month. I had no idea that Social Security always pays benefits one month in arrears - that explains so much of the confusion I've been having. Thanks for asking this question, it's saved me from making the same mistake of overthinking this decision!

I'm a retired benefits counselor and want to add one more piece of advice that might help ease your anxiety: if you do make an error on your application, it's not the end of the world! SSA allows you to make corrections, and you can always call them (though as others mentioned, it can take patience to get through). The most important thing is that you're applying close to your FRA rather than months or years late. Also, keep records of everything - screenshot your application before submitting, save confirmation numbers, and make note of the start date you selected. This documentation can be helpful if any questions come up later. You're being very thoughtful about this decision, which shows you'll handle the rest of the process just fine!

Just wanted to add something that might help - when you're gathering medical records, make sure to get records from ALL your healthcare providers, not just your primary doctor. This includes specialists, physical therapists, mental health providers if applicable, and even emergency room visits. SSA wants to see the complete picture of how your condition affects your daily life and work capacity. Also, ask your doctors to be specific about your functional limitations in their notes. Vague statements like "patient has pain" don't help as much as detailed descriptions like "patient cannot sit for more than 30 minutes without severe pain" or "patient cannot lift more than 10 pounds due to back injury." The more specific functional limitations are documented, the stronger your case will be. Good luck with your application - it sounds like you're being smart about preparing thoroughly!

One thing I haven't seen mentioned yet is timing - since you've been on LTD for 8 months already, you actually have some flexibility in when you apply for SSDI. While your LTD policy probably requires you to apply, most give you a reasonable timeframe (usually within 12-24 months of becoming disabled). This gives you time to make sure your medical documentation is rock solid before submitting. Don't rush into applying just because you're worried about the process - a well-documented initial application has a much better chance of approval than a hastily prepared one that gets denied and has to go through appeals. Also, keep in mind that SSDI has a "closed period" option if you think you might eventually return to work. This lets you claim benefits for a specific time period when you were disabled, rather than claiming ongoing disability. Given that you're dealing with accident injuries that might heal over time, this could be worth discussing with a disability attorney.

Based on what you're describing (concerns about back payments and work income), it sounds like you might be dealing with a potential overpayment situation or the earnings test for early retirement benefits. These are complex areas where getting accurate, personalized advice is crucial. While you can get general information anonymously, at some point, you'll need to discuss your specific case with SSA. When you do, remember that being proactive about reporting changes or concerns almost always leads to better outcomes than waiting for SSA to discover issues later.

As someone who's navigated SSA inquiries before, I'd recommend starting with the SSA's Publication 05-10003 "How Work Affects Your Benefits" - it's available online and covers most scenarios without needing to contact anyone. You can also check out the detailed FAQs on their website about the Annual Earnings Test. If you do call, another approach is to frame your questions around helping a family member or friend understand their options. Representatives are usually happy to explain how the rules work in general terms when you position it that way. Just remember that phone calls to federal agencies can be recorded, so there's always some level of tracking involved. The key is getting enough general information to make informed decisions before you need to provide your personal details for case-specific advice.