Has anyone tried using tax software like TurboTax or H&R Block to calculate their 1040ES payments? I'm wondering if it's worth paying for the self-employed versions just to figure out my quarterly estimates.

I've been dealing with 1040ES forms for a few years now and wanted to share what I learned through trial and error. The key thing that helped me was understanding that the IRS really just wants you to pay as you earn, not wait until the end of the year. For line 6 on the Self-Employment Tax worksheet that you're stuck on - that's asking for half of your self-employment tax. So if you calculated $2,000 in self-employment tax on the earlier lines, you'd put $1,000 on line 6. This represents the "employer portion" that you get to deduct. One thing that saved me a lot of stress was setting up automatic transfers to a separate tax savings account. Every time I get paid, I immediately move 25-30% into that account. Then when quarterly payments are due, I already have the money set aside and I'm not scrambling to find cash. Also, don't stress too much about getting it perfect on your first year. The IRS understands that self-employment income can be unpredictable. As long as you're making good faith efforts to pay what you owe throughout the year, they're generally reasonable about working with you.

Try calling your local taxpayer advocate office. They helped me get mine unstuck after 4 months of nothing

Same exact situation here - verified ID in March, got the 60-day letter in April, and my transcript shows the same 420/570 codes with no movement since. Called multiple times and they keep saying "wait 60 more days" every time I call. It's beyond frustrating especially when you're expecting a large refund. I've heard some people are having luck with contacting their congressman's office for help with IRS issues, might be worth a shot at this point since we're way past the timeframes they promised.

Watch out with amended returns and negative AGI situations! I tried to DIY this myself last year and ended up getting a notice from the IRS because I incorrectly tried to carry forward my entire negative AGI (which included FEIE). The IRS ended up disallowing my claimed carryforward and assessing additional tax plus interest. Make sure you're only carrying forward components that actually qualify - like business losses, not just the negative AGI that resulted from exclusions like FEIE.

Just to add another perspective here - I went through something very similar with my 2021 and 2022 returns. Had a negative AGI in 2021 due to a combination of FEIE and some business losses from freelance work that dried up during COVID. The key thing I learned (after initially getting it wrong) is that you really need to break down what specifically created that negative AGI. In my case, about $18k of the negative was from legitimate business losses that could be carried forward as an NOL, but the rest was from the FEIE which doesn't create a carryover opportunity. I ended up having to file Form 1045 to properly calculate the NOL portion and then amended my following year's return to claim it correctly. The business loss carryforward definitely helped offset some of my 2022 income, but it was way less than I initially thought I could carry forward. If you're dealing with multiple components creating the negative AGI like I was, I'd strongly recommend getting professional help or at least double-checking your work before filing the amendments. The IRS doesn't mess around with incorrectly claimed carryforwards.

Just wanted to add one more consideration that might be relevant to your situation - check if your teacher retirement system has any vesting requirements that could affect your withdrawal options. Some state systems have rules where you forfeit employer contributions if you withdraw before being fully vested (usually 5-10 years of service). Since you mentioned teaching for just under 3 years, you might want to verify what portion of that $7,200 is actually yours to withdraw versus what might be forfeited employer contributions. This could impact whether withdrawal vs. rollover makes more financial sense, though in most cases the rollover is still going to be the better choice tax-wise. You can usually find this information in your annual benefit statement or by calling the retirement system directly (though as others mentioned, getting through can be challenging). Better to know the full picture before making your decision!

One thing that might help with your decision is to consider your current and projected future income levels. If you're expecting to be in a higher tax bracket in the coming years, the rollover becomes even more attractive since you'd be avoiding taxes on that $7,200 at today's rates and potentially withdrawing it later when you're in retirement at lower rates. Also, don't forget to factor in the growth potential difference. Even if your teacher retirement system offers decent returns while inactive, most 401k plans give you access to low-cost index funds that could significantly outperform over the long term. With potentially 30+ years until retirement, that growth difference could be substantial on your $7,200. One last tip - if you do decide on the rollover, ask both administrators for written confirmation of the process and timeline. Government retirement systems can be notoriously slow, and having documentation helps if anything gets delayed or goes wrong during the transfer.

This has been such an informative thread! I'm in a similar situation with my freelance graphic design LLC and was making the same mistake of thinking I could somehow bypass taxation by contributing directly from my business account. Just to summarize what I've learned here for anyone else reading: You MUST pay yourself from the LLC first, pay taxes on that income, and then use the after-tax dollars for Roth contributions. There's no way around this - the IRS requires Roth contributions to come from properly reported earned income. The Solo 401(k) with Roth option sounds like the best path forward for those of us with LLCs making decent income. Being able to contribute up to $23,500 in Roth money (plus potentially more in traditional contributions) versus just $7,000 with a regular Roth IRA is a huge difference for retirement planning. One question I still have - if I set up a Solo 401(k), can I still contribute to my existing Roth IRA in the same year, or do I have to choose one or the other? I've had my Roth IRA for about 8 years and would hate to lose that 5-year clock if possible.

This thread has been incredibly helpful! I'm a tax attorney who works with a lot of small business owners, and I wanted to add a couple of important points that might save people some headaches: First, regarding the S-Corp election discussion - there's a "reasonable salary" requirement that the IRS takes seriously. If you elect S-Corp status, you MUST pay yourself a reasonable W-2 salary for the work you perform, even if it means higher payroll taxes. You can't just pay yourself $20k salary and take $70k in distributions to avoid payroll taxes. The IRS has been cracking down on this, and penalties can be severe. Second, for those considering Solo 401(k)s, remember that if you ever hire employees (even part-time), you'll generally need to include them in the plan, which can get expensive and complicated. A SEP-IRA might be a better choice if you think you'll expand your team. Finally, I'd strongly recommend working with a qualified tax professional before making major changes to your business structure or retirement strategy. The tax code is complex, and what works for one person's situation might create problems for another. The services mentioned in this thread (like taxr.ai) might be helpful for analysis, but they shouldn't replace professional advice for significant decisions. Great discussion overall - it's refreshing to see people taking retirement planning seriously!