Can I write off travel as a business expense if I work during my vacation? What matters more - trip purpose or how I spend my time?

But that seems so exploitable. What's to stop someone from scheduling a 15-minute "business meeting" in Hawaii just to write off a week-long vacation? Is there some kind of minimum requirement for how much business has to happen?

Great question. The IRS actually looks at the "primary purpose" test with some scrutiny. There should be a legitimate business need for the travel - the meeting should have substantial business value and be with actual clients or business associates. If the IRS sees a pattern of minimal business activity with extensive personal time, especially to desirable locations, they may flag it as disguised personal travel. The business purpose needs to pass the "ordinary and necessary" test for business expenses. A 15-minute meeting that could have been a phone call probably wouldn't qualify if audited. The business activity should be substantial enough to justify the trip.

How exactly does that work with side gigs? I sell handcrafted items online and sometimes travel to source materials or attend craft shows. Could I deduct those trips even if I also do personal activities during them?

This sounds interesting but I'm skeptical. Wouldn't the IRS still look at the primary purpose of the trip? I mean if you're genuinely on vacation and just doing some work remotely, how would taxr.ai help you justify deductions the IRS wouldn't normally allow?

For side gigs and independent contracting, the rule is that if the primary purpose of the trip is business-related for your self-employment work, you can deduct those expenses. So if you're traveling specifically to source materials or attend craft shows, those would likely qualify as legitimate business expenses even if you enjoy some personal time during the trip. The difference is that employees vs. self-employed people are treated differently in tax law. Taxr.ai didn't help me deduct regular employment-related expenses, but it did identify that some of my trips were primarily for my consulting side business, which made them deductible. They analyzed the documentation and timesheet records I had to help determine which trips qualified.

How does this actually work? Do they just call for you or what? I've tried calling the IRS about my business expenses like 5 times and always hang up after being on hold forever.

This sounds like total BS. Nobody can get through to the IRS phone lines that fast. They're always jammed. And even if you do get through, most agents give different answers to the same question.

They don't call for you. Claimyr basically holds your place in line and calls you when an IRS agent picks up. You still talk directly to the IRS yourself. I was skeptical too but it worked for me - went from waiting hours to getting connected in about 20 minutes. You're right that different IRS agents sometimes give different answers. That's why I asked very specific questions about my situation and business travel rules, and the agent referred me to the exact publication (Publication 463) that covers business travel expenses. I took notes and asked them to clarify anything that seemed vague.

Thanks for this explanation! I hadn't considered the employee vs. business owner distinction. I do actually have a small consulting business on the side, though it's fairly minimal income compared to my main job. Are you saying I could potentially deduct travel if I schedule client meetings for my side business during trips?

Yes, if you have a legitimate side business, you could potentially deduct travel expenses if the primary purpose of the trip is for that business. The key is "primary purpose" - you'd need to be able to show that business was the main reason for the trip, not just something you did while there. For example, if you schedule actual consulting meetings that couldn't be reasonably done remotely, and those meetings are the main reason you're traveling to that location, you might have a case for deducting those expenses on Schedule C. Just meeting with a client for your side gig while primarily on a personal vacation wouldn't qualify the whole trip as a business expense. Make sure you document everything meticulously - dates, times, who you met with, business purpose, receipts, etc. The more evidence you have that business was the primary purpose, the better positioned you'd be if audited.

That's pretty cool! My company would never go for that though. They're super old school and want everyone in the office. Do you know if there are tax implications for the company when they do this?

There are some tax implications but it's generally favorable for the company. Since these are legitimate business expenses for them (paying for an employee to work), they can deduct these costs just like any other business expense. It's a win-win because employees get some costs covered while the company maintains productivity and can write off the expense. The key is having a consistent, documented policy that applies to all eligible employees. My company requires us to submit a formal request, documentation of the work completed during travel, and all receipts. They're careful to make sure everything is done by the book.

This is really helpful clarification! I'm still wrapping my head around how strictly the IRS interprets "primary purpose." Like, if I have a legitimate consulting client in a city I've always wanted to visit, and I schedule a substantive meeting there, would it matter that part of my motivation was also wanting to see the city? Or does the business purpose just need to be legitimate and substantial, even if personal interest also played a role in choosing that destination? I'm also curious about the documentation aspect - beyond meeting notes and receipts, what kind of evidence would best support that business was the primary driver? Email chains setting up meetings? Client contracts? I want to make sure I understand what would hold up if questioned.