If you are talking about job-related expenses, meaning expenses you incurred for work where you receive a W-2, those are hard to get a deduction for. After you enter the total amount of them, a number equal to 2% of your Adjusted gross Income is subtracted from the total and you only get a deduction for the balance.
After all that, though, there's the problem that these expenses are only one small part of your itemized deductions. Until all your itemized deductions, including things like mortgage interest, add up to more than your standard deduction, they won't benefit you at all. You'll still be taking only the standard deduction.
For example, if you're filing Single, you already get a standard deduction of $6,300. All your itemized deductions would need to add up to more than that, before you would actually switch to itemized deductions. You can only take one or the other. The program gives you whichever is largest because that helps you to owe less tax or get a bigger refund.
