Since we’re looking for jobs right now, I wanted to find any way to save some money in that department. It turns out that many job-search expenses may be tax-deductible, but as you might expect from the IRS, there are plenty of hoops to jump through:

You have to be looking for a new job in your present occupation, even if you don’t ever get one.There cannot be a “substantial break” between the ending of your last job and your looking for a new one. Vague? Yep.You cannot be looking for a job for the first time. Sorry, recent graduates.Job search expenses are lumped in with many other “miscellaneous deductions”, such as the home-office deduction, union dues, work-related education expenses, bad business debt, tax prep ...