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One more thing about extensions that no one mentioned - they're super helpful if you contribute to an IRA! You can make IRA contributions for the previous tax year until April 15th, but if you file an extension, you still only have until April 15th for the IRA contribution. The extension only applies to the filing, not to things like IRA contribution deadlines. I messed this up last year thinking I had until October to make my IRA contribution for the previous year. Just don't want anyone else to make my mistake!
Wait, I'm confused. Are you saying the extension doesn't extend the IRA contribution deadline? Or that it does? Sorry, your wording was a bit unclear to me.
Sorry for the confusion! The extension does NOT extend the IRA contribution deadline. Even if you file an extension giving you until October to file your tax return, you still must make any IRA contributions for the previous tax year by April 15th (the original filing deadline). The filing extension only gives you more time to complete and submit your tax forms - it doesn't extend other tax deadlines like IRA contributions, estimated tax payments, etc. That's the mistake I made thinking I had until October for my IRA contribution.
Has anyone used TurboTax to file an extension? Is it free or do they charge for that too? Their pricing confuses me.
You can file a federal extension for free using Form 4868 directly on the IRS website. Don't pay TurboTax for something that's free! State extensions might be different depending on where you live though.
One important consideration that hasn't been mentioned yet - even if your Wyoming/Delaware LLC doesn't owe US federal income tax because you have no US clients or operations, you WILL most likely need to file: 1. Form 5472 (Information Return of a 25% Foreign-Owned US Corporation) 2. Form 1120 (even if it's a zero return) or potentially 8832 + Schedule C on your personal return depending on election Failing to file these, especially Form 5472, results in a $25,000 penalty PER FORM. I learned this the hard way. And the IRS is getting much stricter about foreign-owned LLCs because too many people were forming them without proper compliance.
Thank you for highlighting this! That $25,000 penalty sounds terrifying. Do you recommend using a registered agent service that specializes in foreign-owned LLCs? And did you find any particular state to be easier to deal with than others for the ongoing compliance?
Yes, absolutely use a registered agent that specializes in foreign-owned LLCs - they'll keep you compliant with state requirements and help ensure you don't miss filings. I personally found Wyoming to be slightly easier than Delaware for ongoing compliance as a foreign owner. Wyoming has simpler annual reports and lower fees. Most importantly, work with a US accountant who specifically handles international clients. Regular CPAs often don't understand the nuances of foreign-owned LLCs and may miss critical filings. I'd recommend setting aside at least $1,500-2,000 annually for proper tax compliance services - it's much cheaper than those penalties!
Has anyone considered using a pass-through structure with an offshore holding company instead? My team (all non-US residents) formed a BVI company that owns our Wyoming LLC. This way: 1. The LLC is treated as a disregarded entity 2. We file minimal US paperwork (still need Form 5472) 3. Banking is managed through the Wyoming entity 4. Tax obligations remain primarily in our home countries This creates an additional layer of separation while maintaining the benefits of a US business presence for payment processing.
One area you might want to focus on during your secondment is owner-manager taxation. This is a huge part of domestic tax practice in Canada that involves integration of corporate and personal tax planning. Ask to sit in on meetings with business owners where the tax team discusses compensation strategy (salary vs dividends), timing of distributions, purification strategies for QSBC status, and estate freeze transactions. These areas combine technical knowledge with practical business advice. Also, pay attention to how tax professionals communicate complex concepts to clients who don't have accounting backgrounds. The ability to translate technical jargon into actionable business advice is what separates great tax practitioners from average ones.
That's a great point about owner-manager taxation! I've had limited exposure to this through some of the trust work, but haven't seen the full picture of how it integrates with corporate planning. Is there a particular industry you think would give the best exposure to these concepts during a short secondment?
Professional services firms (doctors, lawyers, dentists) typically offer the richest learning experience for owner-manager taxation because they have more flexibility in their structures than capital-intensive businesses. They often have complex structures with holding companies, family trusts, and professional corporations all working together. Real estate is another good sector if you want to see how capital gains planning works in practice. The strategies used for property developers versus long-term holders are quite different, and you'll learn a lot about timing strategies for triggering gains or losses.
Quick tip: during your secondment, make sure you understand the difference between tax PREPARATION and tax PLANNING. Many firms keep these functions somewhat separate. Tax preparation is more compliance-focused and involves working with historical data to prepare returns accurately. It's detail-oriented but can be repetitive. Tax planning is forward-looking and strategic, helping clients structure their affairs to minimize tax within legal boundaries. This involves more client interaction and creativity. Based on your comment about enjoying unique problems and solutions, you might gravitate more toward the planning side. But both skills are essential for a well-rounded tax professional.
Totally agree with this distinction! I'd also add that if you're someone who likes definitive answers, tax preparation might be more satisfying. Planning work involves a lot more gray areas where you're dealing with probabilities rather than certainties.
I was in the exact same situation last year (self-employed, Head of Household, income below standard deduction). Just want to share a couple things that helped me. 1) File for the Earned Income Credit!! With one child and income around $10k, you could get back around $3,700 which would more than cover your self-employment taxes. 2) If you use your home for business AT ALL, claim the simplified home office deduction. It's $5 per square foot up to 300 sq ft, so potentially $1,500 of deductions with zero documentation needed. 3) Track ALL your business mileage. Even short trips add up with the 65.5 cents per mile deduction. Don't be ashamed of your income level. The tax system is actually designed to help people in your exact situation, especially with a dependent.
Thank you for the encouraging words and practical tips! I do work from home so the home office deduction sounds perfect. For the mileage - does that include driving to meet clients or pick up supplies? I haven't been tracking that at all.
Yes! Mileage includes ANY driving for business purposes - client meetings, picking up supplies, going to the post office for business mail, driving to the bank to deposit business checks, etc. Basically anything except your regular commute (which you don't have if you work from home!). Start tracking immediately for 2024 - there are free apps like MileIQ that make it super easy. For 2023, you can reconstruct a reasonable estimate using your calendar, email confirmations, receipts from supply stores, etc. Just be realistic with your estimates in case of an audit.
I'm seeing some confusion in these comments so I want to clarify: being under the standard deduction doesn't affect your filing STATUS, but it does affect your tax LIABILITY. With $10,500 in self-employment income, you: 1) Can still file as Head of Household 2) Likely won't owe INCOME tax (because under standard deduction) 3) WILL owe SELF-EMPLOYMENT tax (15.3% of 92.35% of your self-employment income) 4) Can still get REFUNDABLE credits like EITC and Child Tax Credit The self-employment tax would be about: $10,500 Ć 92.35% Ć 15.3% = $1,479 But your EITC with one child at that income level could be $3,000-3,500 So you'd likely get money BACK overall, not owe money!
Wait I'm confused about the math. If the standard deduction is like $20k for Head of Household, and she only made $10,500, how does she owe any taxes at all? Isn't the first $20k tax-free?
Freya Andersen
Just a heads up for anyone using tax software for the Child and Dependent Care Credit - make sure you're entering your expenses correctly. I had a similar issue and realized I was accidentally entering some expenses as "education expenses" rather than "childcare expenses" which caused the software to calculate things differently. Also, check if your state offers a separate childcare credit. In Massachusetts, we have an additional deduction that works differently from the federal credit, and my tax software wasn't prompting me for it until I specifically searched for it.
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Omar Farouk
ā¢Do you know if before/after school programs count as childcare expenses? My kids are in elementary school but I pay for after-school care until I get off work. My tax software is giving me contradictory information about whether this qualifies.
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Freya Andersen
ā¢Yes, before/after school programs definitely count as qualifying childcare expenses as long as they allow you to work or look for work. The IRS is pretty clear on this - any care provided for children under 13 that enables you to work or actively search for work qualifies. The key is that the primary purpose of the program must be childcare, not education. Most standard before/after school programs fall into this category. Summer day camps can also qualify, but overnight camps don't. Make sure you get the tax ID or SSN of the provider, as you'll need to include that on Form 2441.
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CosmicCadet
I found a workaround for the TurboTax issue! If you go to "Review" mode, then select "View/Print Return" (sometimes you have to dig around for this option), you can actually see the completed Form 2441 before paying. In my case, I noticed TurboTax was splitting my childcare expenses across two different entries because I had entered two separate payment periods (spring and fall semesters). This was causing some weird rounding in the calculation. When I combined them into one entry, the credit calculated correctly at exactly $600.
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Natasha Petrova
ā¢Thank you! This worked for me too. When I went to the form view, I saw TurboTax had somehow entered part of my childcare expenses in the wrong field. It was counting some of my expenses as "dependent care benefits" from an employer (which I don't have). Once I zeroed out that field and put everything under the actual expenses, it calculated correctly to $600. Thanks everyone for the help! Saved me from either overpaying for the "expert" review or submitting an incorrect return.
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CosmicCadet
ā¢Glad it worked for you! I've found that looking at the actual forms is always the best way to catch these errors. TurboTax and similar software try to make things "easy" by hiding the forms behind their interview questions, but sometimes that just creates confusion. For anyone else with this issue, another thing to check is that your care provider information is entered correctly. If the provider's tax ID is missing or formatted incorrectly, some tax software will reduce the credit amount without clearly explaining why.
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