Don't forget that if your AGI was over $150,000 last year (or $75,000 if married filing separately), the safe harbor percentage increases from 100% to 110% of last year's liability. Given that you mentioned you're expecting an income increase, this might affect you. Also, if your income is likely to vary significantly throughout the year (common for new self-employed folks), look into using the annualized income installment method. It's more work, but it might prevent you from overpaying early in the year when your income might be lower as you build your business.

When I went self-employed, my accountant told me to just make sure I'm setting aside 30-35% of my gross income for taxes - that covered both the income tax and self-employment tax with a buffer. Way simpler than trying to do fancy calculations each quarter. Just my two cents!

One thing to consider - if you're filing back taxes and expect refunds, double check if you had any stimulus payments during those years. For 2021 especially, if you didn't receive the third stimulus payment ($1,400 per person), you might be eligible to claim the Recovery Rebate Credit on your return. Also, if you had children and were eligible for the expanded Child Tax Credit in 2021, make sure that's accounted for. Those were partially sent as advance payments, but you might be eligible for the remainder. Those two things alone could significantly increase your refund for 2021!

I just went through this whole process of filing 3 years of back taxes. My biggest piece of advice is to gather ALL your documents before starting. Make a checklist: - W-2s from all employers for each year - 1099s (interest, dividends, contractor work, etc) - Mortgage interest statements - Student loan interest - Health insurance forms - Any major life events (buying home, education, etc) Once you have everything organized by year, the software is actually pretty straightforward. I used TaxSlayer for all my back years and while it was a bit pricey (about $40 per year including state), their interface was really easy to use for someone who was overwhelmed like I was.

Anybody have recommendations for how to handle expenses when you're doing both freelance and a part-time W-2 job? I'm still at my design agency 20 hrs/week but building up freelance clients too.

Hey Giovanni! Welcome to the freelance tax world - it's definitely overwhelming at first but you'll get the hang of it. A few quick points to add to the great advice already given: Since you're 8 months in and haven't made quarterly payments yet, you'll likely owe a penalty when you file. For 2025, you can avoid penalties by paying 100% of last year's tax liability (110% if your AGI was over $150k) or 90% of this year's liability through quarterly payments. Since you missed the first few quarters, calculate what you should have paid and make a catch-up payment ASAP. One thing I learned the hard way - keep separate business and personal bank accounts even if you're not formally incorporated. It makes tracking income and expenses SO much easier come tax time. Also, consider getting a business credit card for all your freelance expenses - the statements become your expense records. For your monthly income range ($4,800-5,500), you're definitely going to want to bump that savings rate up to at least 30%. Don't forget about state taxes too if you're in a state that has them. And seriously, start tracking EVERYTHING now - mileage, client meals, software subscriptions, even that new ergonomic chair for your home office. The IRS loves documentation, so keep those receipts!

Pending" processing specifically means your return is in Status 30 in the IRS internal tracking system. This indicates'it s passed initial validation and is queued for substantive review. For amended (returns Form)1040-X , this typically means'it s waiting for assignment to the Accounts Management team rather than the standard processing pipeline. The key distinction is that normal returns are batch-processed, while amended returns require manual review by a tax examiner. This is why amended returns take 16-20 weeks versus 21 days for standardreturns.

I'm dealing with something similar right now - filed my amended return in February and have been getting the same "pending processing" runaround for weeks. What's really frustrating is that they can't give you any real timeline or explain what exactly is happening behind the scenes. From what I've gathered from calling multiple times, it seems like amended returns just sit in a massive digital pile until someone gets assigned to review them. The 10-16 week timeframe they quote is basically their way of saying "we have no idea when we'll get to it." I've started keeping a log of every call I make just to track the different responses I get from different representatives - it's amazing how inconsistent the information is!

One more suggestion - don't forget to check your online IRS account if you have one. Sometimes adjustments are being processed that you don't know about. When I had a similar issue with an excess contribution correction, I noticed that my account showed an adjustment in process before I even contacted them. Turns out their automated systems had flagged the discrepancy and they were already working on it. It just hadn't been completed yet.

I went through this exact same situation last year with my excess Roth contribution. The frustration is real - it feels like the IRS just completely ignored your Line 26 payment! What worked for me was calling the IRS with very specific documentation ready. Before calling, I prepared a simple timeline showing: 1) Original excess contribution date, 2) Date I corrected it with my brokerage, 3) Date I filed amended 2022 return and made the $258 payment, 4) The 2023 1099-R with code 8J. When I finally got through to an agent, having this timeline made the conversation much smoother. The agent could see my 2022 payment in their system and understood immediately that this was a double taxation issue. They processed an adjustment for the full amount I was owed. The key is being very clear about the sequence of events - that you already paid tax on those earnings in 2022, but the 1099-R is trying to tax them again in 2023. Line 26 exists specifically to prevent this double taxation. Don't give up - you're absolutely entitled to that credit!