Level 3
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Business & farm

This was the OP reply to my question:
If you are setting up a self-employment business, you can't deduct any expenses until you actually have income.  Then, your start-up expenses are either deducted all at once in the first year your business is operating (up to $5000), or amortized over 15 years, or a combination, depending on the amount.  For any self-employment, your income and expenses are reported on Schedule C and used to determine your net taxable income or profit.  This is completely separate from itemizing personal deductions like mortgage interest and charity contributions on schedule A.

You can't deduct expenses for one job against the income from another job.  If you have no self-employment income in 2016, then you just file a normal tax return using your W-2.  The only business expenses you could deduct would be expenses related to the W-2 job, and those are itemized deductions subject to the 2%rule.

Also, expenses for education and training to change jobs or meet the minimum requirement for a new career are never deductible.  You can deduct education and training expenses that you pay to maintain or improve your qualifications for your existing job or career.