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Just so you know, payment apps are now working with the IRS more closely than ever. A buddy of mine thought he was being slick by keeping all his side hustle payments under the reporting thresholds, but still got flagged for an audit because his spending didn't match his reported income. They looked at his bank deposits and found regular payments coming in from apps that he hadn't reported. Regardless of how you get paid, the safest approach is just reporting everything. The penalties for unreported income are way worse than just paying the taxes you owe in the first place.
Is there any way to separate personal payments from business ones on these apps? Like if friends pay me back for dinner through Venmo vs clients paying for services?
Yes, most payment apps now allow you to flag transactions as personal or business. PayPal and Venmo both have this feature - you should use it consistently. The personal transactions shouldn't count toward the 1099-K threshold, but the business ones definitely will. Also, I recommend having separate accounts if possible - one for personal use and one strictly for business transactions. Makes record-keeping much cleaner and helps if you ever face questions about what was business versus personal.
Something nobody's mentioned yet - if you're getting paid in cash, you're missing out on building business credit. I shifted from mostly cash to almost all digital payments for my handyman business, and it's helped me qualify for a small business loan because I now have documented income history.
That's actually a really good point I hadn't considered. I've been preferring cash to "avoid the hassle" but my long-term goal is to grow my business enough to get financing for equipment upgrades.
Exactly - when I applied for financing to buy a work truck, the lender wanted to see consistent business income. My payment app history and bank statements showing regular business deposits were crucial for approval. Cash-only would have made that much harder. You should also look into a business banking account if you don't have one already. Many banks offer free business checking for small operations, and it further legitimizes your business when seeking loans or credit.
Just to add another perspective - if you provided more than half of your own support and didn't live with your parents, they definitely can't claim you. The joint return test is just one of many tests that must be met. The IRS has a worksheet to determine "support" - did you pay for more than half of your housing, food, education, medical expenses, etc.? If yes, your parents can't claim you as a dependent, period.
How exactly do you calculate the support test? I paid rent and groceries, but my parents helped with tuition for part of the year and kept me on their health insurance. Does the insurance count as support?
Yes, health insurance premiums paid by your parents would count as support they provided. For calculating total support, you need to add up ALL expenses: housing, food, utilities, clothing, education, medical/dental care, transportation, and other necessities. If your parents paid tuition and health insurance, you'd need to get the dollar value of those benefits. For health insurance, it would be the portion of the premium attributable to your coverage. Then compare their contribution to the total support amount to see if it exceeds 50%.
My sister went through this EXACT situation last year! The tax preparer told her that because she filed jointly with her husband, her parents couldn't claim her - REGARDLESS of the "no tax liability" exception. Apparently, that exception is super rare in practice. The preparer said that once you're married and file jointly, 99% of the time you can't be claimed as a dependent. It's not worth the risk of an audit for your parents to try claiming you.
Your 401k provider is handling this correctly, but there's one detail everyone's missed: you need to check if they're distributing the EARNINGS on the excess contribution separately. Those earnings are subject to the 10% early withdrawal penalty (unless you're over 59.5), even when the excess contribution itself isn't. This is a common mistake 401k providers make. When you get your 1099-R, check if they've separated the excess contribution from its earnings. If they haven't, you might need to calculate this yourself to properly report it on your tax return. The earnings portion should be small if you caught this quickly, but it's still important for accurate tax reporting.
This is really helpful info I hadn't considered. The check I received was for exactly the excess amount ($1,350) minus the 10% withholding. Does that mean they didn't include any earnings, or would the earnings have been calculated into that amount? Should I specifically ask about the earnings portion?
Based on the amount you received, it sounds like they may not have calculated earnings separately, which is actually a mistake. Even a small excess contribution will generate some earnings while it was in the account. You should definitely call your 401k provider and specifically ask about the earnings on your excess contribution. Ask them how those earnings were calculated and how they'll be reported on your 1099-R. The correct procedure is to distribute both the excess contribution and its earnings. If they haven't properly accounted for the earnings, you might need to request an additional distribution specifically for those earnings. The provider should be able to calculate what those earnings were for the period the excess contribution was in your account.
Quick tip: If your 401k provider hasn't been helpful, try contacting the IRS directly at 877-829-5500 which is their specific line for retirement plan questions. That's how I sorted out my excess contribution issues last year.
That number has been impossible to get through on. I tried for weeks and never spoke to anyone. The wait times are insane or they just tell you to call back later.
For what it's worth, I was in almost the exact same situation in 2016 - had W-2 income then switched to 1099 and didn't file. When I finally filed in 2019, I requested a payment plan for about $7300 I owed including penalties. The IRS approved me for a 72-month payment plan at about $115/month. The process was pretty straightforward - I filed Form 9465 with my late return. The penalties weren't as bad as I expected because I was due a refund in one of the years I hadn't filed, which offset some of the penalties. One tip: if you had any estimated tax payments or withholding during that 2018 year, make sure you claim them! They'll reduce your liability even on a late return.
Thanks so much for sharing your experience. That's actually really reassuring. Did you file yourself or use a tax professional? I'm debating whether I should try to DIY this or if it's worth paying someone at this point.
I started trying to DIY it using one of the major tax software programs, but got stuck on how to handle some of my 1099 business expenses. I ended up hiring a CPA who specializes in late filings, which cost me about $350 but was totally worth it. She found several deductions I would have missed on my own, which saved me more than her fee. Plus she knew exactly how to request the payment plan and advised me on the penalty abatement request. If your situation involves 1099 income with business expenses, I'd definitely recommend getting professional help. If it was just W-2 income, you could probably handle it yourself.
Small but important tip - when you do file, make sure you select the correct tax year forms! The IRS won't accept current year forms for past years. You need to find and use the actual 2018 tax forms. You can find previous year forms on the IRS website under "Prior Year" forms. If using tax software, make sure to select 2018 as your filing year. Most major tax software still supports returns from several years back.
Also worth noting that you can't e-file prior year returns (after a certain point). You'll have to print and mail them. Make sure to send it certified mail so you have proof of when you filed it!
Bruno Simmons
One thing nobody's mentioned - if you do offset your $20k gain with the $4k loss, remember that your state tax situation might be different from federal. Some states don't recognize crypto losses the same way the IRS does. I live in California and got surprised by this last year. Had to pay CA state tax on the full amount of my gains even though federally I was able to offset some with losses. Check your specific state tax rules or talk to a local tax pro before making any final decisions about selling those altcoins.
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Tasia Synder
ā¢Damn, hadn't even thought about state tax differences. I'm in Texas so I think we don't have state income tax, but I'll double check. Does anyone know if there are any other gotchas I should watch out for with crypto taxes?
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Bruno Simmons
ā¢You're lucky being in Texas then! No state income tax means you only need to worry about the federal side of things. Another gotcha to watch for is the wash sale rule situation. Currently, crypto isn't subject to the same 30-day wash sale rules as stocks, which means you could technically sell your altcoins for the tax loss, then immediately rebuy them if you still want to hold them long-term. The IRS could change this rule in the future, but for tax year 2025, you're still able to do this. Just make sure you actually execute the sale - moving coins between your own wallets doesn't count as a taxable event.
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Aileen Rodriguez
Just a heads up that the IRS has been getting more aggressive about crypto reporting. Make sure whatever exchange you used is sending you proper 1099 forms. I had a similar situation last year with about $15k in gains and didn't report it all correctly. Got a lovely letter from the IRS six months later saying I owed an additional $3k plus penalties because my exchange had reported the transactions to them.
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Zane Gray
ā¢This is so true. Friend of mine tried to "forget" about $8k in crypto gains and got absolutely hammered with penalties. The exchanges are definitely reporting to the IRS now - this isn't the wild west anymore.
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