Obviously a lot depends on your specific circumstances, but generally speaking it makes sense to do the opposite of what you're talking about and working slightly into 2017 to get your vacation pay into 2017. If you get it in 2016, you'll be taxed on that pay on your marginal rate based on the whole year of working. If you get it in 2017, particularly if your work has a 401K, you can frontload, you oughta be able to put ALL your vacation pay into your 401K and IRA. No taxes, and your AGI will still be $0.