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I'm surprised your tax person doesn't know this. It's Roth IRA 101. You absolutely CAN withdraw your contributions (not earnings) at any time without penalty or tax. That's one of the main benefits of a Roth IRA vs Traditional! The issue is probably that your 1099-R doesn't specify whether it's contributions or earnings being withdrawn. The IRS assumes it's proportional unless you document otherwise. Make sure you file Form 8606 with your taxes to properly indicate these were contribution withdrawals.
What's Form 8606? My tax software never prompts me for this when I enter my Roth info. Is this something I need to fill out separately?
Form 8606 is used to report nondeductible contributions to traditional IRAs and distributions from Roth IRAs. Most tax software should prompt for it when you enter a 1099-R for a Roth distribution, but sometimes you need to specifically look for it or indicate you want to file it. It's important because it helps track your "basis" (the amount you've contributed) in your IRAs, which determines the taxable portion of future distributions. For Roth withdrawals, it helps document that you're taking out contributions (not taxable) rather than earnings (potentially taxable). If your software doesn't automatically include it, you can usually find it in a forms search and add it manually.
Quick tip for the future - keep meticulous records of all your Roth IRA contributions by year! I've been doing this in a simple spreadsheet since I opened mine in 2010. Makes it super easy to prove to the IRS that withdrawals are from contributions. My brokerage's year-end statements don't clearly track cumulative contributions vs. earnings, so having my own records has saved me several times. Just note the date, amount, and tax year for each contribution. Takes 30 seconds each time but saves major headaches later.
Do you know if there's any way to get this historical info if you haven't been tracking it? I've had my Roth since 2017 but never kept records myself.
We looked at CrossBorder Solutions last year for our transfer pricing needs but ultimately went with a different provider. Nothing specifically wrong with them, but we found their sales process to be very aggressive and the pricing structure had some hidden costs that weren't clear upfront. What sealed the deal against them was when we asked for client references like someone suggested above - they were really hesitant to provide any. They eventually offered one, but it was for a company in a completely different industry with much simpler transfer pricing needs than ours. Take their "unlimited service" promise with a grain of salt. When we dug into the contract details, there were quite a few limitations on what was actually included in the base fee.
This is exactly the kind of feedback I was looking for - thank you! Did they explain why they were reluctant to provide references? And what kind of limitations did you find in their "unlimited" service when you reviewed the contract?
They claimed client confidentiality was the reason for not providing references, which is somewhat understandable in tax matters, but most firms find ways to connect potential clients while respecting privacy. When we pushed, it felt like they just didn't have many satisfied customers they could showcase. As for the "unlimited" service limitations, the base fee only covered routine updates to existing documentation. Any changes to your corporate structure, new intercompany transactions, or expanding to new jurisdictions triggered additional fees. Also, their response time guarantee only applied to "routine" questions - anything complex was subject to their availability and often took weeks to resolve.
Has anyone used any of the Big 4 firms for transfer pricing? We're considering CrossBorder Solutions too but wondering how they compare to more established players like EY or KPMG for mid-sized companies?
We use Deloitte for our transfer pricing work. They're definitely more expensive than boutique firms like CrossBorder, but the peace of mind is worth it for us. Their documentation has helped us successfully navigate audits in multiple countries. The big downside is that unless you're a major client, you're often working with junior staff except for the final review.
We switched from PwC to a smaller specialized firm similar to CrossBorder and honestly haven't noticed a drop in quality. The Big 4 expertise is excellent but you pay a significant premium. The mid-tier firms often have former Big 4 partners/managers but with more reasonable pricing. The key is finding a firm with specific experience in your industry and countries of operation.
As someone with severe anxiety myself, getting a dedicated accountant changed my life. Not H&R Block, not a random CPA, but someone I actually connected with who understood my anxiety. I interview several until I found someone who didn't make me feel stupid for my questions.
How did you find your accountant? Did you just google local CPAs or was there a better way to find someone who specializes in working with anxious clients?
Have you considered having a friend or family member sit with you while you use one of the DIY software options? Sometimes just having moral support helps with the anxiety, and most tax software is actually pretty straightforward if you take it one step at a time.
Lots of good advice here but I wanted to add that if you do your own taxes, you can also deduct things like tax publications, tax software, and even a portion of your computer expenses if you use it to prepare your Schedule C. My accountant showed me how to properly document this stuff last year and it added up to a decent deduction.
Does this apply to online tax courses too? I took a short course specifically to learn about self-employment taxes for my Etsy shop.
Yes, courses specifically focused on business taxes for your self-employment activities would generally be deductible as a business expense. A tax course that teaches you how to handle Etsy shop taxes would be considered an ordinary and necessary business expense since it directly relates to your business operations. Just make sure to keep good documentation of the course, including the syllabus or description showing it was focused on business tax topics relevant to your specific situation. Also save your receipt or proof of payment.
I'm in exactly the same boat - regular job plus Uber driving. My accountant charged me $350 and said I could deduct 40% of her fee on Schedule C. She said she bases this on the extra forms and time required for the self-employment portion. Been doing it this way for 3 years with no issues.
Your accountant gives you a specific percentage? Mine just tells me "some of it is deductible" without any clear guidance. Maybe I need a new accountant lol.
Marcelle Drum
Don't forget about municipal bonds! The interest is often exempt from federal taxes and sometimes state taxes too if you buy bonds issued in your state. They typically have lower returns than corporate bonds, but the tax advantages can make up for it depending on your tax bracket.
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Tate Jensen
ā¢Are these easy to buy? Do you just get them through a regular brokerage account or is there some special process? Always been confused about bonds in general.
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Marcelle Drum
ā¢You can buy municipal bonds through most regular brokerage accounts like Fidelity, Vanguard, Charles Schwab, etc. No special process needed. Many people find it easier to invest in municipal bond funds rather than individual bonds - they provide diversification and are more liquid. Just be aware that while the interest is tax-exempt, if you sell the bonds before maturity at a profit, you may owe capital gains tax on that profit. Also, some municipal bond interest can trigger the Alternative Minimum Tax (AMT) if you're subject to it, so look for bonds specifically labeled as "AMT-free" if that's a concern for you.
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Adaline Wong
Has anyone tried Series I Savings Bonds? The interest is exempt from state and local taxes, and you can defer federal taxes until you cash them out. With inflation lately they've been paying decent rates too.
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Gabriel Ruiz
ā¢I bought some last year! Really easy through TreasuryDirect.gov though their website looks like it's from 1997 lol. You can put in up to $10k per person per year. The interest rate adjusts with inflation every 6 months. Definitely a good place to park some money that's safe from both market fluctuations AND taxes.
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