Need step-by-step guide for deducting conference & travel expenses on taxes - tracking receipts when attending industry events

Thanks for the detailed response! So if I understand correctly, I can only deduct the portion related to my 1099 work? How exactly do I determine what percentage to allocate? Should I base it on the percentage of my total income that comes from 1099 work vs W-2? Also, are there specific meal limits I need to be aware of? And what about things like airport parking or Ubers to/from the hotel?

You don't necessarily need to base it on income percentages - it should be based on the actual purpose and use. If 70% of your conference activities relate to your 1099 business and 30% to your W-2 job, then you'd deduct 70% of the expenses. For meals, you can deduct 50% of the cost for business-related meals during your trip. For 2025, some business meals might qualify for 100% deduction, but the standard is 50%. And yes, all transportation costs like airport parking, taxis, Ubers, and even mileage to/from your home airport are deductible at the same allocation percentage as your trip.

Does it work with phone pics of receipts? I'm terrible at keeping paper ones and they're always faded by tax time. Do you also use it for other business expenses or just travel?

I've heard mixed things about AI tax tools. How accurate is it really? I'm concerned about putting trust in software for something as important as tax deductions where mistakes could cost me.

Yes, it actually works great with phone pics! You just snap photos of receipts as you get them, and it extracts all the important info automatically. The text recognition is surprisingly good even with those flimsy thermal paper receipts that fade quickly. I use it for all my business expenses now, not just travel. It handles everything from home office calculations to tracking mileage and recurring subscriptions. The best part is it learns your business patterns over time and gets even better at suggesting proper allocations between personal and business use.

Wait, you actually got through to a real person at the IRS? I've literally given up trying because it's impossible. How exactly does this work? Seems too good to be true.

This sounds like a scam. Why would I pay someone else to call the IRS for me? You can just keep calling yourself and eventually get through. Plus, how do you know the "agent" is even legitimate?

It connects you directly to the IRS's official phone line but somehow bypasses the usual wait times. You're definitely talking to real IRS agents - they verify all your information just like if you called yourself. It's not someone else calling for you - you're on the actual call yourself. The difference is that their system navigates the phone tree and holds your place in line, then alerts you when an agent is about to pick up. I spent hours trying on my own for days and never got through. With this, I was talking to someone in minutes. Totally worth it when you have specific questions about business expense allocations that online research can't answer clearly.

That's a good point I hadn't considered. My company will reimburse up to $1000 annually for professional development, but I haven't used any of it yet this year. Do you think it's better to use that for the conference fee and then deduct the travel costs through my 1099 business? Or would that look strange?

Definitely use your company's $1000 allowance first! That's free money you'd be leaving on the table otherwise. And no, it won't look strange to have part covered by your employer and part deducted through your 1099 business - that's actually cleaner from a documentation perspective. Apply the company reimbursement to the conference registration fee since that's the most straightforward expense, then carefully allocate your travel costs (flight, hotel, meals) between your W-2 and 1099 work based on how you spend your time at the conference. Just make sure you document which sessions or activities relate to your self-employment work to support the allocation if ever questioned.

Per diem only works for meals though, right? You still need actual receipts for hotel and airfare?

Exactly right! Per diem is only for meals and incidental expenses. You absolutely need actual receipts for major expenses like hotel, airfare, conference registration, and transportation. The per diem route is great because meals can add up quickly and are a pain to track individually, especially when you're grabbing coffee between sessions or eating at the hotel restaurant. Just make sure to use the correct per diem rate for the city where your conference is held - rates vary significantly between locations.