Dan, I came to see you this last year for your “Eagles Club” coaching program. Can I deduct that as a job search expense? 
Yes, you certainly can – but here are some guidelines. The first requirement is that the job seeker must be searching for a position in the same field as the job he or she just left.
You cannot deduct these expenses if:
- You are looking for a job in a new occupation
- There was a substantial break between the ending of your last job and your looking for a new one
- You are looking for a job for the first time.
- Employment and outplacement agency fees. You can deduct employment and outplacement agency fees you pay in looking for a new job in your present occupation.
So those looking for their first job and those seeking a new career are out of luck. How will the IRS know if you’ve changed fields or not? To be honest, it probably won’t — that is, unless you get audited. Needless to say, I don’t recommend trying to pull a fast-one on the IRS but this is a stupid distinction. Changing fields is certainly common these days – and many job seekers end up increasing their taxable income dramatically in the process. Why the IRS would want to penalize them is beyond me.
Pretty much any job-hunting expenses are potentially deductible — such as the cost of printing and mailing resumes, phone calls to prospective employers, employment agency enrollment fees and travel expenses, which includes airfare, meals, cabs and car mileage at 56.0 cents a mile.
If you want the specifics, here’s the IRS form: https://www.irs.gov/pub/irs-pdf/p529.pdf
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Still don’t have your tax return ready? April 15 is on us and you haven’t filed your tax return, have you? Well, that’s really not a problem. You can get an automatic extension from the Internal Revenue Service. Remember that you have to pay any owed tax by April 15. The extension is just for filing forms. The IRS has both forms and instructions at:
“Why the IRS would want to penalize them is beyond me.” Honestly, sometimes it seems like the prerequisite to making these laws is to have zero common sense! Good info to know.