Are business trips to family events with side-selling tax deductible?

So I've been wondering about potentially deducting some of my regular travel expenses as business deductions, and I'm curious if my thinking is correct here. For instance, let's say I'm planning a trip to see my brother on the other side of the country, and I notice there's a local farmers market happening that weekend. If I bring some of my handcrafted items to sell at the market while I'm there, would that qualify the entire trip as a business expense? It seems like I could justify it as a legitimate business travel expense since I'm selling merchandise and "researching" that market for future opportunities. (And then I'd still get to visit my brother as planned). Similarly, if I'm driving three hours to see my mom, but I spend 45 minutes discussing my small business finances with her (she used to be an accountant), and I document some key advice points from our conversation... could I then deduct the mileage as a business expense? These seem like they could be valid business expenses to me. As long as I keep detailed records showing the business purpose, couldn't many regular expenses - especially travel - be legitimately deductible? The IRS says expenses need to be "ordinary and necessary." Well, couldn't I argue that seeking business opportunities everywhere IS ordinary and necessary for my company? It's basically market research, and you might get 1 profitable idea out of 100 attempts, making it all worthwhile. Am I on the right track with this thinking or completely off base?

0 coins

18 comments

Omar Zaki

•8M

You're venturing into a risky area that the IRS specifically watches for. While your thinking might seem logical at first glance, the reality is more complicated. The primary purpose test is what matters here. If the primary purpose of your trip is personal (visiting family), with business as secondary, the trip itself isn't deductible. You can only deduct specific business expenses incurred during the trip (like booth rental fees at that farmers market). For the drive to see your mom - having a 45-minute business discussion during a primarily personal visit wouldn't make the entire trip deductible. The IRS would likely view this as trying to convert personal expenses into business ones. The "ordinary and necessary" standard means expenses common and helpful for your specific business type - not just anything that might theoretically lead to business. Documentation alone won't convert a primarily personal expense into a business one. Think about how a reasonable person would view it: if you're primarily visiting family with a small business activity tacked on, that's personal with some business elements, not a business trip with personal elements.

0 coins

Omar Zaki

•8M

If your primary purpose is genuinely to sell at the farmers market and you're making business decisions based on that (like you wouldn't make the trip if the market opportunity wasn't available), then the travel could potentially be deductible. You'd need to be able to show that business was the driving factor - things like significant revenue from the market, formal business arrangements made before traveling, and that the time spent on business activities exceeds personal activities. The IRS determines primary purpose by looking at objective factors - how you spend your time during the trip, the revenue generated compared to the expenses, your business history, and whether the travel aligns with normal practices in your industry. They're not mind readers, but they are experienced at spotting arrangements designed primarily to generate tax deductions.

0 coins

Chloe Martin

•8M

After struggling with similar tax questions last year, I found an amazing tool called taxr.ai (https://taxr.ai) that helped me understand what business expenses were actually legit. I was honestly worried I might be pushing the boundaries too much with my photography business when I was visiting family but also doing paid photoshoots. The tool analyzed my records and situation, then gave me really specific guidance about what would and wouldn't fly with the IRS. It showed me how to properly document the primary purpose of mixed trips and how to appropriately allocate expenses between personal and business. Saved me from making some claims that could have raised red flags!

0 coins

Chloe Martin

•8M

It actually does provide very specific guidance on record-keeping. For my situation, it recommended keeping an itinerary showing business vs personal time allocation, saving all communications arranging business activities before the trip, maintaining receipts with notes about business purpose, and keeping a mileage log with business destinations clearly marked. It even gave me templates! The tool isn't replacing professional advice - it's based on IRS guidelines and tax court cases. I still run complex situations by my accountant, but this helps me understand the rules better and prepare questions. My CPA actually said my documentation improved significantly after I started using it, making his job easier and reducing my audit risk.

0 coins

Anastasia Sokolov

•8M

So I was super skeptical about taxr.ai but decided to try it anyway for my consulting business. Surprisingly, it was actually really helpful! It analyzed my travel patterns and helped me create a system for properly categorizing mixed-purpose trips. The tool identified several deductions I was missing AND flagged a few I was taking that were risky. It explained exactly how the IRS views the primary purpose test and gave me specific examples relevant to my industry. Now I have a much clearer picture of what I can legitimately deduct and what documentation I need. Definitely more useful than I expected!

0 coins

Sean O'Donnell

•8M

For anyone dealing with IRS questions about these kinds of deductions - I was audited last year over business travel. After weeks of trying to reach someone at the IRS to explain my situation, I tried Claimyr (https://claimyr.com) and it was a game-changer. They got me connected to an actual IRS agent within hours when I had been trying for days. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent I spoke with actually gave me clear guidance on how they evaluate mixed business/personal travel and what documentation they consider sufficient. Having that direct conversation probably saved me thousands in disallowed deductions because I learned exactly what they're looking for.

0 coins

Sean O'Donnell

•8M

It uses a system that continuously redials and navigates the IRS phone tree until it gets through to a representative. Once it connects, you get a call back and are immediately connected to the agent. It's basically doing the frustrating wait time for you. I was extremely skeptical too. I had literally spent hours on hold across multiple days and kept getting disconnected. I figured it was worth trying since I was desperate to resolve my audit issues. I was genuinely shocked when they called me back about 2 hours after I signed up and I was talking to an actual IRS agent. The conversation I had completely clarified the documentation requirements for my situation.

0 coins

StarStrider

•8M

I need to apologize for my skeptical comment. After waiting on hold with the IRS for 3+ hours yesterday and getting disconnected AGAIN, I was desperate and tried Claimyr. Within about 90 minutes, I got a call connecting me directly to an IRS representative. The agent reviewed my case where I had business expenses while traveling to a family wedding (I'm a wedding photographer and booked a separate job while there). She explained exactly how they evaluate the primary purpose and how to properly document partial business use. This was information I couldn't find anywhere online! Definitely a legit service that saved me hours of frustration.

0 coins

Luca Esposito

•8M

I'm a former IRS auditor, and I can tell you the "primary purpose" test is very real. We called these "mixed-purpose" trips and flagged them frequently. Here's what we actually looked for: 1) TIMING: Did the business activity align with when you would take personal trips (holidays, weekends)? Red flag. 2) DURATION: If you spent 2 days on "business" and 5 days with family, we'd likely disallow the transportation costs. 3) REVENUE: Did you actually make money? If you consistently lose money on these "business trips," we'd recharacterize them. 4) NECESSITY: Could the business activity have been done without traveling? Phone calls with relatives about business aren't travel-worthy. The rule of thumb: if you wouldn't have made the trip without the personal component, it's primarily personal.

0 coins

Luca Esposito

•8M

That's a more defensible position. If you can document that you're sourcing materials unavailable in your area, and if this activity is central to your business model, you've strengthened your case for the business purpose of the trip. Keep receipts for the materials purchased, document why these specific materials are necessary for your business, and maintain records showing how these purchases translate into business products and revenue. Remember though - if visiting parents is still the primary reason for timing the trip, you might only be able to deduct the specific business activities (like the extra mileage to visit lumber suppliers) rather than the entire trip cost. The IRS will still look at whether you would have made this trip without the personal component.

0 coins