Has anyone looked into whether it's better to take distributions from your S-Corp and then fund a backdoor Roth vs setting up these more complex retirement plans? Especially if you expect to be in a higher tax bracket in retirement?

This thread has been incredibly helpful! I'm in a similar situation but with one additional wrinkle - I'm also contributing to a HSA through my W-2 job. Does that impact any of the S-Corp retirement plan contribution limits mentioned here? Also, for those who mentioned taxr.ai - did their analysis include HSA optimization as part of the overall retirement planning strategy? I'm trying to figure out if I should prioritize maxing my HSA first before setting up the Solo 401k, or if they work completely independently of each other. One more question - if I set up a Solo 401k through my S-Corp this year, can I still make catch-up contributions when I turn 50 next year, or do those limits get complicated when you have multiple 401k accounts?

Just wanted to add that if you take money from your HSA, make sure to keep ALL medical receipts, even small ones. The IRS allows you to reimburse yourself for qualified medical expenses from years ago (no time limit) as long as the expense occurred after you established the HSA.

Connor, I'm really sorry to hear you're in such a tight financial spot. Before you make any moves on your retirement accounts, I'd strongly suggest checking if you have any unreimbursed medical expenses from the past few years that you paid out of pocket. As Malik mentioned, the HSA has this amazing feature where you can reimburse yourself for qualified medical expenses with no time limit - as long as the expense occurred after you opened your HSA account. This could potentially let you withdraw from your HSA completely penalty-free if you have documentation for past medical bills, prescriptions, dental work, vision expenses, etc. Even something like over-the-counter medications (with a prescription), medical equipment, or travel expenses for medical care can qualify. Keep every receipt and make sure the total amount you withdraw doesn't exceed your documented qualified expenses. If you don't have enough past medical expenses to cover what you need, then yes, the 401k loan route would be much better than an early withdrawal. At 28, you've got decades for that money to grow - the real cost isn't just the penalties, it's the lost compound growth over time. Hang in there, and make sure to explore every option before touching those retirement funds! 💪

Has anyone used Wise (formerly TransferWise) for this kind of thing? They have much better exchange rates than banks or Western Union and it seems more legitimate than running transfers through your personal account.

Just want to echo what others have said about using legitimate remittance services instead of your personal accounts. I learned this the hard way when Bank of America started asking questions about my transfer patterns. Even though you're not making money from this, banks have automated systems that flag unusual patterns. Multiple international transfers, especially to the same countries, can trigger anti-money laundering reviews regardless of the amounts. For tax purposes specifically - you're right that there's no income to report since you're not profiting. But do keep detailed records showing the money flow (who gave you what, when you sent it, confirmation of delivery) just in case. The IRS generally cares about this stuff when there's actual income involved. Consider suggesting your friends use Remitly, Western Union, or Wise directly. It's actually easier for everyone and removes you from the middle of potential regulatory scrutiny. Plus your friends might get better exchange rates going direct.

Just a heads up - if you're paying through EFTPS for the first time, make sure you complete the payment by 8PM ET the day BEFORE the due date. A lot of people miss this and think they can pay until midnight on the due date, but EFTPS payments take a day to process. Found this out the hard way last year!

Thanks for all the helpful responses, everyone! I went ahead and started the EFTPS enrollment process yesterday after reading through these comments. @Abby Marshall - that 8PM deadline tip is super important, I had no idea about that! I was planning to pay on the actual due date which would have been a disaster. I'm also going to look into taxr.ai since a few people mentioned it helped clarify the process. It sounds like it could save me from making mistakes in the future. For now, since I'm cutting it close to my deadline, I might use the credit card payment option through one of those third-party processors just to be safe, even with the fee. One more question - does anyone know if EFTPS sends email confirmations for payments, or do I need to print/save something from their website when I make the payment?

Has anyone considered using a Solo 401k instead of a SEP IRA? When I was in your exact situation, I found that a Solo 401k let me contribute significantly more than a SEP IRA would.

Great discussion here! I'm in a similar situation with my freelance consulting income alongside my W-2 job. One thing I'd add is that if you're just starting out with retirement savings from self-employment income, don't get too caught up in optimizing between SEP IRA vs Solo 401k initially - the most important thing is to start saving something. That said, I did switch from SEP IRA to Solo 401k after my second year once I understood the benefits better. The Solo 401k does allow for much higher contributions, especially if your self-employment income is on the lower side. With my consulting bringing in about $35,000 last year, I was able to contribute the full $23,000 employee contribution plus about $6,400 employer contribution with the Solo 401k, versus only being able to do about $6,400 total with the SEP IRA. For anyone considering the switch, just make sure your provider supports Solo 401ks - not all do, and some charge higher fees than others.