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One thing nobody's mentioned - since you're technically "homeless" (living in your car), look into whether your state has any earned income tax credits for low-income/homeless individuals. Some states offer additional tax benefits beyond the federal EITC that might help in your situation. Also, keep all receipts for laundry, showers, etc. While they aren't business deductions, they help document your living situation if you ever need to prove your homeless status for any assistance programs or tax benefits.
Do you know which states specifically have these credits? I'm in California and doing the exact same thing as OP (Uber/car living) and could really use any extra tax breaks available.
California definitely has one of the more generous state EITCs called the CalEITC. For tax year 2024 (filing in 2025), if your income is below certain thresholds (around $30,000 for a single filer), you could qualify for both the CalEITC and the Young Child Tax Credit if you have a dependent under 6. For your car-living situation, California also has some specific programs through counties that offer tax preparation assistance for homeless individuals, which includes people living in vehicles. Look up the CalEITC4Me program or visit your local VITA (Volunteer Income Tax Assistance) site - they can help identify all credits you're eligible for based on your specific situation.
Ravi Sharma
Don't forget about the self-employment tax on top of income tax! That's an extra 15.3% on your net profit that catches a lot of first-time gig workers by surprise. Make sure you're setting aside enough to cover both income tax and SE tax.
Yara Nassar
ā¢Yeah I'm definitely worried about that self-employment tax hit. Do you know if I should be making quarterly estimated payments? I haven't done any yet this year since I wasn't sure how to calculate them with my unusual expenses situation.
NebulaNomad
ā¢The IRS has a safe harbor rule that might help - if you pay at least 90% of this year's tax OR 100% of last year's tax liability (110% if your previous year AGI was over $150k), you won't get hit with underpayment penalties. Since this is your first year self-employed, you might be able to use your prior W-2 job's withholding as your safe harbor amount.
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I was in almost the identical situation 2 years ago. Here's what I learned after talking with a tax professional: 1. Keep DETAILED records separating your expenses. I use different credit cards for each venture and different categories in my accounting software. 2. Make sure your startup has a clear business plan and path to profitability. The IRS gets suspicious if you claim losses for too many years. 3. For me, filing separate Schedule Cs made tracking everything clearer, especially since I planned to bring on a partner for the startup later. 4. The home office deduction gets complicated with multiple businesses. I ended up calculating time spent in the space for each business and prorating based on hours. Hope this helps! The first year is the hardest - it gets much easier once you have systems in place.
Pedro Sawyer
ā¢Did your accountant recommend any specific software for tracking dual businesses? I'm currently using a spreadsheet but it's getting unwieldy.
I started with QuickBooks Self-Employed but found it limiting for multiple businesses. I switched to QuickBooks Online Small Business which lets you track multiple businesses with separate profit & loss statements. FreshBooks is another good option that many of my freelancer friends use. The key feature to look for is the ability to tag transactions by business/project and run separate reports. If you're on a tight budget, Wave is free and can handle basic tracking for multiple ventures. Whatever you choose, set it up correctly from the beginning - I wasted hours recategorizing transactions because I didn't have a proper system initially.
Mae Bennett
Quick tip from my own experience: Don't overlook potential QBI (Qualified Business Income) deduction implications! If your freelance work is profitable but startup is running losses, filing separate Schedule Cs might preserve your ability to claim QBI on the profitable business. Combined, your overall business profit might be too low for a meaningful deduction.
This is actually super important advice that saved me thousands last year. My accountant initially combined my businesses, but when we separated them, I was able to claim QBI on my consulting income while still deducting all startup losses.
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Aisha Rahman
One thing nobody's mentioned yet - there's an opportunity cost to giving the IRS an interest-free loan. If you apply your $3200 refund to next year, that's money that could be: - Invested in your business equipment - Put in a high-yield savings account (currently 4-5%) - Used to pay down business debt - Covering operating expenses during slow months I've been running my small consulting business for 8 years and I ALWAYS take the refund now, then set up automatic transfers of 25% of my income to a separate tax account. This gives me both the cash flow benefit AND peace of mind for quarterly payments.
Do you ever worry about forgetting to make those quarterly payments? That's my biggest fear - getting hit with penalties because life got busy and I missed a payment date.
Aisha Rahman
ā¢I set up calendar reminders for all four quarterly tax payment deadlines (April 15, June 15, September 15, and January 15) with alerts two weeks before each one. I actually have a separate checking account just for taxes and transfer money there with each invoice payment. You can also use the IRS Direct Pay system to schedule payments in advance if you're worried about forgetting. The penalties aren't massive if you miss by a little bit, but they do add up over time. The peace of mind from having a system is definitely worth the small amount of setup time.
Ethan Brown
Another consideration that helped me decide: your first year business profits are often not a good predictor of your second year. My first year refund was large because I over-withheld, being cautious. But my second year had way different income patterns. If I'd applied my first year refund to my second year, it would have been way too much for Q1 and not enough for the rest of the year when my business grew. Taking the refund and then making estimated payments based on actual quarterly income worked MUCH better.
That's such a good point! My first year in business was totally different from my second. How do you estimate your quarterly payments when your income is so irregular? Do you use the safe harbor rule or do you try to calculate based on actual income?
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Just be careful about what you mean by "selling" your crypto. If you're selling on a centralized exchange, that's pretty straightforward. But if you're swapping one crypto for another (like trading your underwater coin for a stablecoin), that's still a taxable event. Also make sure you're accounting for fees in your cost basis calculations. I messed this up last year and had to file an amended return when I realized I hadn't included gas fees in my cost basis, which meant I overpaid on taxes.
What about if you swap to a different crypto and then immediately back? Like ETH to USDT and then back to ETH? Does that still count as a valid loss?
Yes, that absolutely counts as a valid loss (or gain). Each conversion is a separate taxable event. So if you go from ETH to USDT and recognize a loss, and then from USDT back to ETH, those are two distinct transactions. The IRS doesn't care what you do with the proceeds after you sell, they just care that you're reporting each taxable event. This is actually why crypto can be such a tax nightmare - every single swap, conversion, or trade is a reportable event, not just when you cash out to fiat.
I'm curious if anyone knows - do different states handle crypto tax losses differently? Like, I know the federal limit is $3k per year for writing off losses against ordinary income, but do some states have different rules?
Oliver Cheng
ā¢Most states follow federal treatment, but there are exceptions. For example, Nevada, Wyoming, and South Dakota have no state income tax so it's not an issue there. New Jersey doesn't allow carrying forward capital losses like the federal government does. Always worth checking your specific state's rules.
Paolo Marino
To answer your original question simply: Your traditional IRA basis would be $0 because you've moved everything to the Roth through conversions. But you absolutely must file Form 8606 each year to track those nondeductible contributions and conversions. TurboTax should ask if you made contributions to an IRA. Tell it yes, specify they were nondeductible contributions to a traditional IRA, then indicate you converted to a Roth. TurboTax will generate the proper 8606 form if you answer all the questions accurately.
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Dmitry Volkov
ā¢Thank you! That makes sense. So even though I put in $18,000 over those three years, since I converted it all, my traditional IRA basis is now $0. Does that mean if I check my traditional IRA account, it should show a $0 balance too?
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Paolo Marino
ā¢Yes, if you converted the full contribution amount each year, your traditional IRA account balance should show $0 or close to it (maybe a few cents of interest if there was any time delay between contribution and conversion). Remember that "basis" refers to the money you've already paid tax on. Since backdoor Roth contributions start as nondeductible traditional IRA contributions (meaning you've already paid tax on that money), you don't pay tax again when converting to Roth as long as you convert quickly before any earnings accumulate and you properly document everything on Form 8606.
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Amina Bah
Just wanted to add that if you're doing backdoor Roth conversions regularly, be careful about the pro-rata rule if you have any other traditional IRA, SEP IRA, or SIMPLE IRA accounts with pre-tax money in them. The IRS looks at all your IRA accounts together when calculating taxes on conversions.
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Oliver Becker
ā¢This is such an important point! I messed this up one year when I had an old 401k that I had rolled into a traditional IRA. Made my backdoor Roth partially taxable because of the pro-rata rule. Definitely something to watch out for.
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