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Dont forget about the standard mileage deduction!!! Its 67 cents per mile for 2024 i think which adds up FAST. I drove about 5000 miles for doordash last year and it saved me thousands in taxes. Make sure you track EVERY mile from when you turn the app on until you turn it off.
Actually the standard mileage rate is 65.5 cents per mile for 2023 reporting (filed in 2024) and 67 cents for 2024 (which you'll file in 2025). And you can't just deduct every mile from when the app is on - you need to be actively working (driving to pickup, to delivery, or to a hotspot). Just having the app on while you're parked at home doesn't count.
Great question, Lily! I've been doing gig work alongside my full-time job for about two years now, and the tax situation definitely takes some getting used to. Here are a few key things I wish someone had told me when I started: First, open a separate checking account just for your Doordash earnings. Deposit everything there and immediately transfer your tax savings (I do 30% to be safe) to a separate savings account. This makes tracking so much easier and ensures you're not accidentally spending your tax money. Second, start tracking expenses from day one - not just mileage, but also things like phone accessories (car mounts, chargers), insulated bags, and even a portion of your phone bill since you're using it for work. These add up more than you'd think. The quarterly payment thing sounds scary, but it's really not that bad once you get into the rhythm. Just remember the dates: April 15, June 15, September 15, and January 15. You can make payments online at irs.gov/payments - super easy. One last tip: consider adjusting your W-4 at your regular job to have extra taxes withheld. Sometimes that's easier than making quarterly payments, especially if your Doordash income isn't huge. Good luck with saving for that truck!
This is really helpful advice! I'm also considering doing gig work while keeping my day job. The separate bank account idea is genius - I never would have thought of that but it makes total sense for keeping everything organized. Quick question about the W-4 adjustment - how do you figure out how much extra to have withheld? Is there a calculator or formula, or do you just estimate based on how much you expect to make from Doordash?
Has anyone had success deducting UPF sun protective clothing for outdoor work? My dermatologist actually wrote me a note recommending specialty sun protective gear including hats and shirts since I work on boats all day. Wondering if the same "specialized equipment" rule might apply?
I successfully deducted UPF clothing for my landscaping business last year. The key was having my dermatologist write a letter specifically stating these were medically recommended for my occupation, not general use. Also made sure to buy styles/colors that were clearly work clothes (company logo, not fashionable). Documentation is everything!
Thanks so much for sharing your experience! I already have the doctor's note, so I'll definitely look into getting some work-specific UPF gear with my company logo. That's a really smart way to clearly designate them as work clothes versus regular attire. Did you happen to take photos of the clothing for your records too?
As someone who's been through multiple IRS audits for my marine equipment rental business, I can tell you that documentation is absolutely critical for these types of deductions. For your polarized sunglasses, I'd recommend creating a simple business use log - just date, hours worked, and brief description of conditions (like "8-hour charter, bright sun, open water"). The fact that you have separate personal sunglasses is huge in your favor. I also keep photos of my business-specific gear alongside receipts to show the difference between work and personal items. For sunglasses specifically, polarized lenses for water work have a much stronger case than regular tinted glasses since they serve a specific anti-glare function that's directly tied to safety and job performance. One thing that helped me was getting a brief letter from my insurance company acknowledging that proper eye protection is recommended for marine work - it adds another layer of documentation showing these aren't just personal preferences but legitimate business necessities.
That's really smart thinking about getting documentation from your insurance company! I never would have thought of that angle. Do you think a similar letter from my boat charter insurance provider acknowledging that proper eye protection reduces liability risk would carry the same weight? I'm definitely going to start that business use log you mentioned - it seems like having contemporaneous records rather than trying to recreate everything later would be much more credible if I ever get audited. The photo documentation idea is brilliant too, especially showing the difference between my work polarized glasses and regular personal sunglasses.
I think you're underestimating the IRS's ability to track related transactions, especially with larger amounts like $22,000. The IRS has sophisticated data matching systems that can connect 1099-B forms (showing your stock sale) with gift tax returns (if you file Form 709) and your children's brokerage accounts. Even if you stay under the annual gift tax exclusion and don't file Form 709, brokerage firms report all transactions. If your kids buy the same stock shortly after you sell it, especially if they're using accounts at the same brokerage, that creates a clear paper trail. The audit risk might be low, but the consequences of having your loss deduction disallowed plus potential penalties make it worth being careful. A safer approach might be to wait the full 30 days before gifting the money, or have your kids invest in genuinely different securities that aren't substantially identical to what you sold.
This is really eye-opening about the IRS's tracking capabilities. I had no idea they could match up transactions across different accounts like that. The 30-day waiting period before gifting sounds like a smart safeguard - it would help establish that the gift and any subsequent purchases by the kids were separate decisions rather than part of a coordinated plan. Do you know if there's any official guidance on what constitutes a "safe" time gap between the sale and gift to avoid step transaction issues?
There isn't specific official guidance on a "safe" time gap for step transaction issues, but tax attorneys I've consulted generally recommend at least 30-60 days between related transactions to help establish independence. The key is that each transaction should have its own legitimate business purpose. For gifts specifically, you want to document that the gift was made for normal family reasons (birthday, holiday, general financial support) rather than as part of a tax avoidance scheme. Keep records showing the gift was unconditional - your kids can do whatever they want with the money, including not investing it at all. The step transaction doctrine isn't just about timing though. The IRS looks at factors like whether the transactions were legally interdependent, whether intermediate steps had economic substance, and whether the taxpayer was committed to completing the entire series of steps from the beginning. Good documentation of independent decision-making at each step is crucial.
One important consideration that hasn't been mentioned yet is the gift tax implications. While you mentioned the $22,000 gift, remember that the 2024 annual gift tax exclusion is $18,000 per recipient. If you're gifting $22,000 to each of your three children ($66,000 total), you'll exceed the annual exclusion limits and need to file Form 709. This actually creates additional documentation that could make it easier for the IRS to connect your stock sale to your children's subsequent purchases. The gift tax return would show the timing and amounts of your gifts, which could be cross-referenced with their brokerage activity. Consider splitting the gifts between you and your spouse (if married) to stay within the annual exclusion limits, or spacing the gifts across tax years. This reduces both the gift tax filing requirements and the paper trail that might trigger IRS scrutiny of the overall transaction sequence. Also, make sure your children understand they should make their own independent investment decisions with the gifted funds, and document that the gifts are unconditional with no expectation about how the money will be used.
This is a really important point about the gift tax reporting! I hadn't considered how filing Form 709 would create that direct paper trail linking the stock sale to the gifts. The timing suggestion about splitting gifts across tax years is smart too - it not only avoids the reporting requirement but also creates more separation between the sale and any subsequent purchases by the kids. One question though - if you're married filing jointly, can both spouses use their $18,000 annual exclusion for the same recipients even if only one spouse actually makes the gift? Or does the money need to actually come from both spouses' accounts to qualify for the combined $36,000 exclusion per child?
Has anyone used the IRS withholding calculator for this? I tried but it seems more designed for W-2 income than retirement accounts. Is there a better calculator specifically for retirees with IRA distributions?
The IRS Withholding Estimator isn't great for retirees. I've had better luck with some of the retirement-specific calculators from Schwab or Fidelity. They have options specifically for pension and IRA income that the IRS calculator doesn't handle well.
Brady, congratulations on reaching retirement! This is such an important question and you're smart to think about it upfront. I went through this exact same situation about 2 years ago when I started my IRA withdrawals. The 10% default is rarely the right amount for most people. What really matters is your total tax picture - not just the IRA withdrawal itself. You'll want to consider: 1. Your other retirement income (Social Security, pensions, part-time work) 2. Your filing status and standard deduction 3. Any other taxable income or capital gains 4. Your state's tax treatment of retirement income I ended up needing to withhold 20% because I had Social Security and some rental income that pushed me into a higher bracket than I expected. The key is to think about your total annual income, not just the IRA portion. One practical tip: Start conservative your first year. You can always adjust the withholding percentage for future distributions based on how your first tax season goes. It's better to get a refund than owe penalties for underpayment. Have you calculated what your total retirement income will be for the year? That's really the starting point for figuring out the right withholding rate.
This is really helpful advice, Ryan! I'm actually in a similar situation to Brady - just starting to think about retirement withdrawals. Your point about calculating total retirement income first makes a lot of sense. Quick question: when you mention starting conservative and adjusting later, how often can you actually change the withholding percentage? Can you do it monthly, quarterly, or is there a limit on how frequently you can adjust it? I'm worried about either over-withholding early in the year or under-withholding if my income changes mid-year. Also, did you find any good resources for estimating what your Social Security and other income will actually be? I'm having trouble getting accurate projections for planning purposes.
Malik Johnson
I'm a new member here but have been following this discussion closely since I'm experiencing the exact same issue! My DDD is also 5/22 and like everyone else, there's absolutely nothing showing as pending in my Navy Fed account. This is my first year banking with Navy Federal after switching from Bank of America, so I had no idea this was their new policy. I was genuinely starting to panic thinking my direct deposit information was wrong or that my return got flagged for some reason. The complete silence from their system is so different from what I experienced with my previous bank. Reading through all these experiences has been incredibly reassuring - it's clear this is a widespread policy change and not an issue with individual accounts. I really appreciate everyone who took the time to call customer service and share the details about why they made this change. While I understand their reasoning about reducing confusion, it definitely creates more anxiety when you're counting on that refund! I'm going to follow the advice about setting up account alerts and try to be patient until Thursday morning. Thanks to this amazing community for helping me understand what's really going on behind the scenes - I would have been a nervous wreck without finding this thread!
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Katherine Shultz
ā¢Welcome to the community! I'm also brand new here and can completely relate to your experience switching from a different bank and being caught off guard by Navy Fed's policy change. I came from Wells Fargo where pending deposits always showed up 2-3 days early, so this complete radio silence has been really unsettling. It's such a relief to find this thread and realize we're all going through the same thing with our 5/22 DDDs. The community here has been amazing at sharing information and helping everyone stay calm during what could otherwise be a really stressful waiting period. I've already set up those account alerts based on the earlier suggestions, and it's definitely helping me resist the urge to constantly refresh my app. Here's hoping we all wake up Thursday morning to good news - based on everyone's shared experiences, it sounds like Navy Fed's deposits are still reliable even if their transparency isn't what it used to be!
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Ella Lewis
I'm a new member here and this discussion has been incredibly helpful! I'm also dealing with a DDD of 5/22 and the same frustrating situation with Navy Fed showing absolutely nothing pending. This is my third year with them, and the change from their previous policy of showing pending deposits 2-3 days early has definitely caught me off guard. What's been particularly stressful is that I'm a single parent and was counting on this refund to cover some unexpected car repairs that came up last week. The complete lack of visibility into whether the deposit is even in their system has had me questioning everything from my return accuracy to my direct deposit information. Reading through everyone's experiences has been such a huge relief - it's clear this is a bank-wide policy change and not an issue with individual returns. I really appreciate all the members who took the time to call customer service and share what they learned about Navy Fed's reasoning behind this change. While I understand they want to reduce confusion, the uncertainty is definitely more stressful than helpful from a customer perspective. I'm going to set up those account alerts that several people mentioned and try to be patient until Thursday morning. Based on all the shared experiences here, it sounds like the deposits are still hitting reliably on the actual DDD despite the lack of advance notice. Thanks to this community for helping me stay calm - without finding this thread, I would have probably spent the next two days calling both Navy Fed and the IRS unnecessarily!
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