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As someone who's dealt with both unfiled returns and PTO payouts, I'd strongly recommend getting those back tax filings sorted out ASAP before making any decisions about the PTO timing. The IRS has different rules and potential penalties for late filing that could affect your overall tax strategy. For the PTO itself, one thing to consider is your state's tax situation too - some states have different withholding rules for lump sum payments that could impact your decision. Also, if you're planning to use any of that $10k for major purchases or debt payoff, the timing of when you actually receive the cash (after withholding) vs. when you get it back as a refund could matter for your financial planning. Given the complexity with the health insurance subsidies, unfiled returns, and potential salary increase, this might be worth a consultation with a tax professional who can run the numbers for your specific situation rather than trying to figure it all out on your own.
This is really solid advice. I'm in a similar situation with unfiled returns and I never thought about how state withholding might be different for lump sums. Do you know if there's a general rule about which states treat lump sum payouts differently, or is it something I'd need to research state by state? Also, when you say "tax professional," are you thinking CPA or would someone like an enrolled agent be sufficient for this kind of situation?
@Connor Murphy For state withholding differences, it really varies quite a bit. States like California and New York tend to have higher supplemental withholding rates up (to 13.3% and 13% respectively ,)while states like Texas and Florida don t'have state income tax at all. Some states follow federal supplemental withholding rules, others have their own flat rates for bonuses/lump sums. You d'probably need to check your specific state s'revenue department website or ask your payroll department how they handle it. As for tax professionals, either a CPA or enrolled agent would work well for this situation. Enrolled agents actually specialize specifically in tax matters and can represent you before the IRS, which might be particularly helpful given the unfiled returns. CPAs have broader training but many focus heavily on tax work too. The key is finding someone experienced with unfiled returns and complex timing situations like this - maybe ask potential candidates specifically about their experience with catching up on back filings and income timing strategies.
I've been through something very similar with a large PTO payout and unfiled returns. Here's what I learned that might help: First, regarding the withholding vs actual tax liability - you're absolutely right that it evens out when you file. However, there's a cash flow consideration many people miss. If you take the lump sum now, you'll likely have 22% federal plus state withholding taken out immediately, but you won't see that money back until you file your return (which could be months away if you're still catching up on prior years). For the health insurance subsidies, this is actually the biggest factor in your decision. The ACA subsidy cliffs are steep - you could lose thousands in premium tax credits by going just a few hundred dollars over the income threshold. Since you mentioned expecting a salary increase next year, splitting the PTO between December and January might be worth it just to manage your annual income in each tax year. One thing I don't see mentioned yet - since you haven't filed for 3 years, you should know that the IRS stops processing refunds after 3 years. So if you had refunds coming for 2021 or earlier years, you may have lost them permanently. This makes it even more important to get caught up on those filings before worrying about optimizing this PTO payout. My suggestion: handle the unfiled returns first, then use those actual income figures to model out how the PTO timing affects your taxes and subsidies for both this year and next year.
This is really comprehensive advice, thank you! The point about losing refunds after 3 years is something I definitely didn't know - that's a huge wake-up call. I'm curious though, when you say to handle the unfiled returns first, do you mean I should actually file all three years before making the PTO decision? That seems like it could take months, and my company is asking for a decision pretty soon. Also, you mentioned modeling out the ACA subsidy impacts - is there a reliable way to calculate those cliffs myself, or do most people need professional help for that kind of analysis? I'm trying to figure out if this is something I can reasonably DIY or if I really need to bite the bullet and hire someone.
I'm experiencing the exact same issue! My DDD was 2/23 and I'm using Netspend through Pathward as well - still no sign of my refund. I've been checking my account multiple times a day hoping it would magically appear. Called Netspend customer service yesterday and they gave me the same response about no pending deposits showing up. It's really stressful when you're depending on that money for bills and expenses coming due. After reading through everyone's experiences here though, I'm feeling a lot more reassured that this is just typical Pathward timing - seems like they consistently take the full 4-5 business days they're allowed to hold our funds. It's frustrating that they can earn interest on our money during that time while we're left wondering if something went wrong. Thanks for starting this thread - it's comforting to know so many of us are going through the same delay right now with Pathward. Definitely considering switching to a regular bank account next year to avoid this stress!
I'm going through this exact same thing! DDD 2/24 with Netspend/Pathward and still waiting too. It's my first time using a prepaid card for my refund and I had no idea they could hold it for so long. I've been refreshing my account like crazy thinking maybe I missed a notification or something. Reading all these stories has been really helpful though - now I understand this is just how Pathward operates unfortunately. It's so annoying that they get to make money off our refunds while we're sitting here stressed about when we'll actually get our own money! Definitely learned my lesson for next year. Hang in there - sounds like we should see our deposits by the end of this week based on everyone else's experiences!
I'm dealing with the exact same frustrating situation! My DDD was 2/24 and I'm still waiting on my Netspend card through Pathward. It's so stressful when you need that money for bills and expenses. I've called Netspend twice and they keep saying no pending deposits, which just makes me more anxious. But reading through all these comments has been incredibly helpful - I had no idea Pathward was notorious for taking the full 4-5 business days they're legally allowed to hold our funds. It's really annoying that they can earn interest on OUR money while we're left wondering if something went wrong. I've been obsessively checking my account every few hours hoping it'll magically appear! From everyone's experiences here, it sounds like this is just typical Pathward behavior and we need to wait out that full 5 business day window. Definitely switching to a real bank or credit union next year to avoid this stress. Thanks for posting this - it's reassuring to know we're all going through the same Pathward delays right now!
I'm going through the EXACT same thing! DDD was 2/25 and my Netspend/Pathward is still showing zero. This is incredibly frustrating - I've been checking my account literally every hour thinking maybe I missed something. It's so stressful when you have bills coming due and you're counting on that refund money. Reading everyone's experiences here has been really eye-opening though. I had no idea that Pathward consistently takes the full 4-5 business days just to make interest off our own money! That should honestly be illegal. I've called Netspend three times now and keep getting the same "no pending deposits" response which just makes me more paranoid. But it sounds like this is just their standard operating procedure unfortunately. Definitely going to open a credit union account before next tax season - this waiting game is absolutely brutal when you need your own money! Thanks for sharing your experience - at least we know we're all suffering through this Pathward delay together.
I appreciate everyone sharing their experiences and expertise here! As someone new to this community, I've learned a lot just from reading through this thread. The consensus seems clear that claiming exempt when you know you'll owe taxes isn't worth the legal risk, even if some people have gotten away with it in the past. What really stood out to me was @StarSeeker's audit story - knowing that the IRS has automated systems specifically flagging exempt claims that don't match up with tax liability is pretty sobering. And @Sasha Ivanov's point about the 90%/100% rule for withholding requirements helps explain why the penalties exist in the first place. For anyone else considering the exempt route, it sounds like the smarter play is using the IRS withholding calculator and Form W-4's Step 4(c) to legally reduce withholding while staying compliant. Combined with maximizing 401k contributions and maybe setting up an automatic transfer to a separate tax savings account, you can achieve most of the same cash flow benefits without the audit risk. Thanks to everyone who took the time to explain the real consequences and better alternatives!
This has been such an informative discussion! I'm new here too and really appreciate how helpful everyone has been. I was actually considering a similar approach with my W4 at my new job, but after reading through all these responses, I'm definitely going to stick with the legal withholding adjustments instead. The combination of real experiences (especially the audit story!) and professional advice from people like @Sasha Ivanov really shows why taking shortcuts with tax compliance isn t'worth it. I had no idea that employers had to submit exempt W4s to the IRS or that there were automated systems flagging mismatches. Going to check out that IRS withholding calculator and maybe look into some of those other tools people mentioned for getting proper guidance. Better to do it right from the start than deal with penalties and audits later!
I'm glad I found this discussion! I was honestly tempted to claim exempt on my W4 at my new job because withholding always feels like giving the government an interest-free loan, but reading everyone's experiences here has completely changed my mind. The point about it being a legal certification rather than just a tax strategy really hit home. I don't want to risk an audit or penalties just to get a bit more cash flow each month. @StarSeeker's story about getting flagged by automated systems is exactly the kind of real-world consequence that makes you realize it's not worth the gamble. I think I'll follow the advice to use the IRS withholding calculator and adjust my W4 properly using Step 4(c). That way I can still optimize my take-home pay without breaking any rules. Plus the idea of maxing out 401k contributions to reduce taxable income is something I should be doing anyway for retirement planning. Thanks to everyone who shared their knowledge and experiences - this community is incredibly helpful for navigating these tax questions!
Welcome to the community! I'm also relatively new here but have been following this thread closely. It's amazing how much you can learn just from one discussion - I had no idea about the automated flagging systems or that exempt W4s get submitted directly to the IRS. Your point about withholding feeling like an interest-free loan to the government is something I've thought about too, but you're absolutely right that the legal risks just aren't worth it. The audit story really puts things in perspective about what can happen when you try to game the system. I'm planning to take the same approach you mentioned - use the official tools to optimize legally rather than risk penalties. It sounds like we can still achieve most of the cash flow benefits without the compliance headaches. Good luck with your new job!
To add something different to the QuickBooks discussion - I'm a bookkeeper who works with several self-employed clients. Here's how I recommend handling quarterly estimated taxes: 1) Set up a specific equity account called "Owner's Draw - Tax Payments" 2) When you need to pay taxes, transfer money from business to personal as an owner's draw 3) Pay the taxes from your personal account 4) Track the amounts in a separate spreadsheet so you know how much you've paid toward taxes each year This keeps your business books clean and accurate while still giving you the records you need for tax time. Remember that these payments are NOT business expenses - they're distributions of profit.
Do you recommend setting up automatic transfers for this? I keep forgetting to do the transfers and then end up scrambling at quarterly tax deadlines. Is there a way to automate this in QuickBooks?
I generally recommend setting up recurring transfers from your business account to personal account specifically for taxes. Most banks allow you to schedule these quarterly to align with tax due dates (April 15, June 15, Sept 15, Jan 15). QuickBooks itself doesn't automate the transfers, but you can set up recurring reminder transactions that prompt you when it's time to record the owner's draw. Go to Lists > Memorized Transactions and create a new memorized transaction for your owner's draw. Set it to remind you quarterly before each due date. This way you'll get a QuickBooks notification when it's time to handle the transfer and make the payment.
I'm looking at my QuickBooks right now and don't have an Owner's Draw account. I only see a bunch of expense categories. How do I add that as an account type? And would this be considered an equity account or something else? Thanks for being patient with my beginner questions!!
In QuickBooks, you'll want to create an Equity account for this. Here's how: 1. Go to Chart of Accounts 2. Click "New" 3. Select "Equity" as the account type 4. Name it "Owner's Draw" or "Owner's Distributions" 5. Save it Then when you pay your quarterly taxes, instead of categorizing it as an expense, you'll categorize it to this equity account. This correctly shows you're taking profit out of the business rather than counting it as a business expense.
Thank you so much! I found it and was able to create the equity account. I also went back and recategorized my previous tax payment. My profit and loss statement looks different now (higher profit) but I guess that's more accurate since I'm not counting tax payments as expenses anymore. One more question - will this affect how much I need to pay in estimated taxes for next quarter since my profit is showing higher now?
Dylan Cooper
Just wanted to share my experience as someone who went through this exact situation last year! I was renting a room in a shared house and using part of it for my freelance writing business. After doing a lot of research and consulting with a tax professional, I ended up going with the actual expense method rather than the simplified $5/sq ft method because it worked out better for me. Here's what I learned: 1. You definitely calculate based on your rented room space, not the whole house (Option 1 is correct) 2. Keep detailed records of everything - measurements, photos, rent receipts, utility bills 3. For utilities, only deduct the business percentage of what YOU actually pay (not what roommates pay) 4. The "exclusive use" test is really important - I made sure my desk area was only used for work, never personal stuff One tip that really helped me: I created a simple spreadsheet tracking my monthly expenses and business use percentage. Made tax time so much easier and gave me confidence that everything was documented properly. The deduction ended up being pretty substantial for me - definitely worth doing it right! Just make sure you're comfortable with the record-keeping requirements.
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Andre Laurent
β’This is really helpful, Dylan! I'm curious about your spreadsheet setup - what specific columns or categories did you include to track everything? I'm trying to set up something similar but want to make sure I'm capturing all the right information for my home office deduction. Did you track utilities monthly or just calculate an annual average? Also, when you say the deduction was "substantial," are we talking about saving hundreds or thousands on taxes? I'm trying to decide if it's worth the extra paperwork compared to just using the simplified method.
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Anita George
β’@Andre Laurent For my spreadsheet, I tracked: monthly rent my (portion ,)utilities I pay for internet, (my share of electric/gas ,)square footage measurements, and business use percentage. I calculated utilities monthly since they vary seasonally. For me, the actual expense method saved about $400 more than the simplified method would have. My office space was small 35 (sq ft so) the $175 simplified deduction wasn t'great, but my rent portion was high enough that the percentage method worked better. Definitely worth running both calculations to see which gives you more! The key columns in my spreadsheet were: Date, Expense Type, Total Amount, My Portion, Business Percentage, Deductible Amount. Made it super easy to total everything up at year-end.
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Aisha Hussain
Great question about home office deductions for room rentals! I actually just dealt with this exact situation when filing my taxes as a freelance developer. You're absolutely right to go with Option 1 - calculate based on your rented room space (40 sq ft / 130 sq ft = ~31%), not the entire house. Since you're only responsible for rent on your room, that's the appropriate denominator for your calculation. For utilities, here's what I learned works: You can only deduct the business percentage of utilities that you actually pay for. So if you pay $50/month for your share of electricity, you'd deduct 31% of that ($15.50/month). Same goes for internet - if you pay $30/month as your share, you can deduct about $9/month. One thing that really helped me was keeping a simple log with photos of my setup and measurements. The IRS loves documentation, especially for home office deductions. Your divider setup sounds perfect for meeting the "exclusive use" requirement. Also worth noting - run the numbers both ways (actual expense method vs. simplified $5/sq ft method). With 40 sq ft, the simplified method would give you $200 total, but depending on your rent and utilities, the actual expense method might be significantly better. The key is being consistent and keeping good records. Sounds like you're already on the right track!
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