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Ask the community...

  • DO post questions about your issues.
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  • DO post tips & tricks to help folks.
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Chloe Martin

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Don't forget about Section 195 of the tax code! You can elect to deduct up to $5k of your startup costs in the year your business becomes active, and then amortize any remaining startup costs over 15 years. But the $5k immediate deduction starts getting reduced if your total startup costs exceed $50k (which doesn't sound like an issue in your case). The key is that you have to make this election in the year your business becomes active. If you don't make the election, you have to amortize ALL the costs over 15 years instead of getting that immediate $5k deduction.

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Wait, so this is an "election" we have to specifically make? How do we do that? Is there a specific form or do we just deduct the $5k on our Schedule C?

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Chloe Martin

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You make the election by attaching a statement to your tax return for the year your business begins operations. The statement needs to include the amount you're electing to deduct, a description of the expenses, and the month your business began active operations. You'll also report the actual deduction on either Schedule C (for sole proprietors) or your business entity return. The remaining amount over $5,000 would then be amortized over 15 years starting with the month your business began. Most tax software will walk you through this if you indicate you have startup costs, but it's good to be aware of the requirement for the election statement.

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Make sure you're tracking these expenses properly from the beginning! I messed up my first year in business by just throwing all receipts in a shoebox and trying to sort it out at tax time. NIGHTMARE. For your daycare business, you should set up separate categories right now: - Supplies (consumable items like art supplies, cleaning products) - Equipment (durable goods like furniture, play structures) - Professional services (licensing fees, legal costs) - Marketing/advertising - Insurance - Training/education costs Trust me, you'll thank yourself next April!

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Are there any good apps you recommend for tracking this stuff? I'm starting a small side business too and want to do it right from the beginning.

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Mia Alvarez

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This might be unpopular, but I've started charging extra for clients who bring in disorganized or obviously fake records. I have a tiered pricing structure - clients with proper bookkeeping pay my standard rate, while those with "creative accounting" pay 1.5-2x more to compensate for the additional work and risk. I explain this policy upfront so there are no surprises. Some clients clean up their act to avoid the higher fees, and others are willing to pay extra for me to sort through their mess. Either way, I'm compensated for the headache.

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Carter Holmes

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Do you have any suggestions for how to determine what falls into the "higher fee" category? Do you have specific criteria or is it more of a judgment call?

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Mia Alvarez

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I've developed a pretty clear checklist that I review with clients in our initial consultation. Higher fees apply if their records show: unsorted receipts/statements, missing months of data, personal expenses mixed with business, revenues that don't match 1099s or bank deposits, or rounded numbers for most expenses (like you mentioned). I also charge more if they bring everything in last minute (less than 3 weeks before deadline) or if they have no formal bookkeeping system at all. Having clear criteria makes it less personal and more about the actual work involved. I've found being transparent about this from the start weeds out problem clients and encourages others to get organized.

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Sophia Long

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Am I the only one who actually just refuses these clients? After being burned a few times early in my career, I now have a strict policy: no proper books = no service. Life's too short and my license is too valuable.

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How do you screen for this before taking them on? Do you have some kind of initial assessment process?

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For what it's worth, my tax preparer explained the "at risk" question to me this way: If you personally could lose the money you put into your business, it's "at risk." If you have some arrangement where you can't lose some of the money (like certain limited partnerships or non-recourse loans), then some investments are "not at risk." For most small freelancers who just started out, you'll almost always select "all investments at risk" because you're using your own money and don't have fancy financial protections.

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So if I borrowed money from my parents to start my freelance business, but promised to pay them back no matter what, would that be considered "not at risk"?

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No, borrowing from your parents with a promise to pay them back would still be considered "at risk" for tax purposes. The money is still at risk in your business - if your business fails, you might not be able to repay them regardless of your promise. "Not at risk" typically refers to very specific financial arrangements like non-recourse loans (where the lender can only take specific collateral but can't come after you personally) or certain complicated partnership arrangements with guaranteed returns. These are relatively uncommon for most small freelancers.

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Maya Patel

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Another schedule C question - Does anyone know if TurboTax handles this "at risk" question automatically? I'm trying to decide which tax software to use for my freelance work.

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TurboTax does ask this question during the Schedule C section, but it doesn't really explain it well. I ended up having to Google it anyway. I've heard FreeTaxUSA explains it a bit better and is cheaper too.

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Keisha Brown

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Former tax preparer here. Just a friendly warning - if you've been getting notifications for YEARS and ignoring them, you may already be in the collections process. At this point, you should: 1) Open and read every single notice you've received 2) Find out if there are any liens or levies already filed against you 3) Get professional help IMMEDIATELY Also, the IRS has something called Substitute for Return (SFR) where they file a return on your behalf if you don't file. These are almost always TERRIBLE for you because they don't include deductions or credits you might be entitled to. If they've done SFRs for you, you'll need to replace those with actual returns.

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StormChaser

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Thanks for the heads up. I was afraid of that. I just checked my credit report and there are no liens showing up yet, so maybe I caught it in time? Would the liens definitely show on my credit report or could they exist without showing up there?

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Keisha Brown

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Tax liens don't always show up on credit reports anymore - the credit bureaus changed their policies a few years back. The absence on your credit report doesn't guarantee there's no lien. You should request an "Account Transcript" from the IRS for each tax year to see exactly where you stand and what actions they've taken. You can request these online through the IRS website if you can create an account, or your tax professional can request them for you with proper authorization. These transcripts will show if they've filed SFRs, assessed penalties, or initiated collection actions.

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I've been watching this thread since I'm in a similar situation (8 years unfiled). Has anyone dealt with the Fresh Start program? I've heard it can help reduce penalties?

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Dmitry Petrov

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The Fresh Start Initiative can definitely help in your situation. It expanded options for installment agreements and offers in compromise. One key benefit is penalty abatement - especially for first-time non-filers. You might qualify to have some penalties reduced or removed entirely.

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Another option is to print out the relevant section from IRS Publication 544 which specifically addresses this. Page 3 explicitly states that "basis is the amount of your investment in property for tax purposes. The basis of property you buy is usually its cost." There's nothing in there about the basis being limited to purchases in the current tax year because that's not how it works. You could also show examples of Schedule D and Form 8949 where previous year purchases are clearly reported in the current year's tax forms when sold.

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Jacinda Yu

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Thanks for the suggestion about Publication 544! I just pulled it up and found the exact section you mentioned. I'm going to email this to my tax preparer tonight along with a few examples. If she still doesn't get it after reading the IRS's own publication, I think I'll definitely need to find someone new to help with my taxes. Really appreciate everyone's help here. It's been driving me crazy thinking I was missing something obvious!

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Glad I could help! Just to add one more resource - if you look at the actual Form 8949 instructions, there's a worksheet that clearly shows how to report transactions where the purchase and sale dates are in different years. That might be the most direct evidence to show your preparer. Good luck! And yes, if she still doesn't understand after seeing the actual IRS guidelines, it might be time to find someone with more experience in investment taxation.

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Malia Ponder

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I had a very similar issue last year. My tax guy had never dealt with crypto before and was making the same mistake. What finally got through to him was when I compared it to real estate - if you buy a house in 2010 and sell it in 2023, you don't just report the selling price on your 2023 taxes with no reference to what you originally paid! The same principle applies to literally any capital asset - stocks, bonds, crypto, collectibles, etc. The year you establish your cost basis and the year you realize the gain/loss can be (and often are) different.

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Kyle Wallace

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That real estate comparison is perfect! Makes it super clear even for people who don't understand investments.

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