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Liam McGuire

What can I deduct on taxes as job-hunting expenses in 2025?

I got laid off in November and finally found a new position last month. As I'm prepping for my tax return, I'm wondering what counts as a legit job-hunting expense? Since I was working as an independent contractor, I wasn't able to get unemployment benefits. I'm curious because when you're unemployed and actively searching, couldn't regular living expenses technically count as job-hunting expenses? Like internet service, part of my phone bill, or even coffee shop purchases when I'm applying for jobs there? I already know about the obvious stuff like resume services, travel for interviews, and networking event fees. Also, are there any special tax breaks or deductions available for people who were unemployed but didn't qualify for unemployment benefits? This was my first time being without work for an extended period (almost 3 months), and I want to make sure I'm not missing anything that could help reduce my tax burden.

Job hunting expenses can be tricky for tax purposes, especially since the 2018 tax law changes eliminated miscellaneous itemized deductions for most taxpayers through 2025. Before 2018, you could deduct job search costs as miscellaneous itemized deductions if you were looking for a job in your current occupation (not a career change) and if those expenses exceeded 2% of your adjusted gross income. Unfortunately, these deductions are currently suspended. However, if you're self-employed or an independent contractor, you may still be able to deduct certain expenses related to finding new clients or contracts on Schedule C. These might include website costs, professional subscriptions, networking event fees, and business cards. Regular living expenses like food, rent, and utilities generally don't qualify as deductible job hunting expenses, even when you're unemployed. The IRS requires expenses to be ordinary and necessary for your trade or business.

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Wait, are you sure about this? I heard from a friend that the job hunting expense deduction is coming back for 2025 taxes. Something about those Trump tax cuts expiring? Is that true or am I confused?

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You're thinking of the right concept, but with slightly different timing. The Tax Cuts and Jobs Act provisions that suspended miscellaneous itemized deductions (including job hunting expenses) are scheduled to expire after 2025, not before. So for 2025 taxes (filed in 2026), these deductions would still be suspended under current law. After 2025, unless Congress extends the current provisions or creates new legislation, the tax code would revert to allowing these deductions again. But for your current situation with 2024 income that you'll file in 2025, these deductions are still unavailable as miscellaneous itemized deductions.

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I struggled with similar questions last year after losing my marketing contract work. I tried using some online tax prep software but got frustrated with the confusing answers about deductions. Then I found https://taxr.ai which actually analyzed my specific situation as an independent contractor. The AI tax assistant helped identify several deductions I was missing related to my freelance work. While I couldn't deduct regular job hunting expenses, I found out I could deduct continuing education expenses, professional organization memberships, and home office expenses that were related to maintaining my professional skills and freelance business, even during periods between contracts. The tool asks questions about your employment situation and guides you through what might be deductible for your specific circumstances. Way more helpful than generic advice I was finding elsewhere.

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Does it actually work for complicated situations? Like I did some gig work while looking for a full-time job, plus had investment income. Can it handle something like that?

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I'm always skeptical of these AI tools. How does it compare to just asking a real CPA? Does it give actual tax advice or just generic information you could find anywhere?

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It actually does work well for complicated situations. I had a mix of W-2 income from a part-time job, 1099 income from three different clients, and some Etsy sales. The tool helped me categorize everything correctly and identified deductions specific to each income stream. It even flagged potential audit triggers in my situation and suggested documentation I should keep. Regarding your question about comparing to a CPA, I actually used both. I consulted with a CPA after using the tool, and they were impressed with the accuracy. The AI gives personalized tax advice based on your specific situation and current tax law, not just generic information. The CPA ended up only making minor adjustments to what the tool recommended, saving me hours of paid consultation time.

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Just wanted to follow up on my skeptical comment about taxr.ai - I decided to try it out of curiosity and was seriously impressed. I had a weird mix of independent contractor work, unemployment for part of the year, and some side hustle income from online tutoring. The analysis it provided showed me that while I couldn't claim traditional job hunting expenses, I could deduct business expenses for my independent contractor work during the periods I was actively working, which I hadn't fully documented before. It spelled out exactly what qualified and what didn't, and flagged some home office deductions I was taking incorrectly. Definitely saved me money and potential headaches. Much more in-depth than I expected!

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If you're struggling to get answers from the IRS about your specific situation as an independent contractor, I highly recommend using https://claimyr.com to get through to an actual IRS agent. I spent literally weeks trying to get someone on the phone to clarify what I could deduct after being laid off from my consulting gig. After three failed attempts and hours on hold, I used Claimyr and got connected to an IRS representative in under 45 minutes. They explained exactly what self-employment deductions I could take during periods between contracts. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent clarified that while general job hunting expenses aren't deductible anymore, certain expenses to maintain my professional standing as a consultant were still deductible on Schedule C.

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How does this actually work though? I thought the IRS phone lines were just permanently jammed. Is this like paying to skip the line or something?

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This sounds like a scam honestly. Why would anyone pay for something the government provides for free? And why would the IRS allow some third party to jump their phone queue? I don't buy it.

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It works through an automated system that navigates the IRS phone tree and waits on hold for you. When an actual IRS agent picks up, you get a call connecting you directly to them. It saves you from having to sit on hold yourself, which is especially helpful if you've been disconnected multiple times after long waits. Regarding it being a scam - I was skeptical too! But it's not about "jumping the queue" - everyone still waits their turn. The service just does the waiting for you and alerts you when an agent is available. The IRS doesn't know or care that you're using a service - they just see a caller waiting like anyone else. I wasted over 15 hours trying to get through on my own before using this, so the time saved was absolutely worth it.

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I need to eat my words about Claimyr being a scam. After my skeptical comment, I decided to try it myself since I had a question about my 1099-NEC income and deductions that I couldn't find clear answers to online. I was shocked when I actually got connected to an IRS agent in about 35 minutes after weeks of failed attempts on my own. The agent confirmed that while job hunting expenses aren't deductible as itemized deductions anymore, I could still deduct business expenses related to maintaining my independent contractor business on Schedule C, even during slower periods. This was exactly the clarification I needed, and I would have never gotten through without the service. Sometimes paying to save time is actually worth it!

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Don't forget about education expenses! If you took any courses or certifications to improve your skills while job hunting, you might qualify for the Lifetime Learning Credit. It's worth up to $2,000 depending on your income. The education doesn't have to be degree-seeking - just something that improves your job skills. I took a digital marketing certification while unemployed last year and was able to claim it. The credit directly reduces your tax owed, not just your taxable income.

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Does this apply if the training is in a different field than what you were working in before? I was in customer service but took coding classes while unemployed to switch careers.

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Yes, that's actually one of the great things about the Lifetime Learning Credit - unlike some other education benefits, it doesn't require you to be pursuing a degree or even staying in the same field. Your situation taking coding classes to switch from customer service to a tech career would absolutely qualify, as long as you paid for the training and it was from an eligible educational institution. The credit is worth 20% of the first $10,000 in qualified education expenses, so potentially up to $2,000. There are income limitations though - for 2024, the credit starts phasing out at $80,000 for single filers and $160,000 for married filing jointly.

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Did anyone mention health insurance deductions? When I was between jobs as a contractor, I found out I could deduct 100% of my health insurance premiums as a self-employed person on Line 17 of Schedule 1. Saved me a ton! You don't even need to itemize to get this deduction.

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Does this work if you were only self-employed for part of the year? I had a regular W-2 job until July, then did freelance work for the rest of the year while job hunting.

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Yes, this can work for partial-year self-employment! You can deduct health insurance premiums for the months you were self-employed, but only if you weren't eligible for employer-sponsored coverage during those months. Since you had W-2 employment until July, you'd need to make sure you weren't eligible for COBRA or other employer coverage during your freelance period. The deduction is calculated monthly, so you'd prorate it for just the months you qualify. Make sure to keep good records showing when your employer coverage ended and your self-employment income began.

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