What exactly is an "accountable plan"? My company is small (like 15 people) - would this work for us too? Our boss is actually pretty reasonable but I don't think he knows about tax stuff like this.

An accountable plan is simply a formal reimbursement arrangement that follows IRS guidelines. It works for companies of any size - even tiny businesses with just a few employees! The basic requirements are that expenses must have a business connection, employees must adequately account for these expenses (with receipts, etc.) within a reasonable time, and employees must return any excess reimbursement. When these conditions are met, the reimbursements aren't included in employee wages, which means they're tax-free to the employee and the company doesn't pay employment taxes on them. For a small 15-person company, it's actually easier to implement because there's less bureaucracy. Your boss just needs a simple written policy outlining how employees should submit expenses and get reimbursed. There are templates online, or an accountant could set it up quickly. It's win-win because the company can deduct the expenses and employees receive tax-free reimbursements!

It covers basically any unreimbursed expense that's "ordinary and necessary" for your job. Before 2018, you could potentially deduct things like union dues, work clothes (if not suitable for everyday use), work tools, professional subscriptions, continuing education, home office (if required by your employer), etc. But now, most of these are NOT deductible for W-2 employees through 2025. Some exceptions still exist though - teachers get a special $300 deduction for supplies, and some education expenses might qualify for education credits instead.

You need to deduct those as business expenses! The 1099-K shows the gross amount paid by customers, including Uber's cut. Go to the expenses section of Schedule C in FreeTaxUSA and deduct all the commissions and fees that Uber took. You should have a breakdown of these in your annual summary from Uber.

That explains why I got one this year but not last year! I didn't make that much more driving but crossed the threshold I guess. Thanks for mentioning this.

That's really helpful about the deadline! I had no idea there was a cutoff for getting refunds. Does the IRS charge penalties for filing late if you're owed a refund?

Good news - the IRS generally doesn't charge penalties if they owe YOU money. Penalties and interest typically only apply when you owe them. So if you're confident you'll be getting refunds, you should be fine penalty-wise. That said, filing sooner rather than later is always better. Besides the refund deadline I mentioned, having unfiled returns can sometimes cause issues with other government programs or financial applications like mortgages. Some people also find that their refund was larger than expected, which is a nice surprise!

I used FreeTaxUSA for a late 2020 return last year and it worked great. Super straightforward and much cheaper than TurboTax or H&R Block for prior years. Federal was free like you said, and I paid $15 for state. They walk you through everything step by step.

3 Wait, is that really true even if you're claimed as a dependent? I thought dependents couldn't open retirement accounts.

9 Yes, it's absolutely true! Being claimed as a dependent doesn't affect your ability to contribute to a Roth IRA. The only requirements are that you have earned income and don't exceed the contribution limits (either your total earned income or $6,500 for 2023, whichever is lower). Many parents miss this opportunity for their working teens. It's a fantastic way to start building tax-free retirement savings early, and the compound interest over decades is incredible. I opened mine at Vanguard with help from my parents when I was still in high school.

11 Good point! Does anyone know if you need to file state taxes if you're under 18? I'm in California and making about $8,000 this year through my parent's Venmo.

I tried Wealthsimple Tax last year for my non-resident return. It works okay for simple situations, but I found it struggled with properly applying tax treaty benefits. I ended up switching to a professional preparer because I wasn't confident it was handling everything correctly.

Actually, if you have Canadian self-employment income, the deadline is June 15, even for non-residents! But any balance owing is still due by April 30 to avoid interest charges.

You're absolutely right about the June 15 extension for self-employment income. Thanks for that correction! Always good to remember that even with the extended filing deadline, paying after April 30 will result in interest charges, even if you're not charged a late-filing penalty.