Tax planning doesn’t necessarily get easier as you age. There are times when taxes get more complicated as you get older. When taxes are complex, there are more opportunities to benefit from proactive tax planning. This could be good news in the form of tax deductions and tax credits. Tax often feels more complicated as you age, partially because you likely have more sources of income. Not to mention once you leave the workforce, you must deal with tax withholdings on your own. Other tax complications exist around Medicare premiums, Social Security, and Required Minimum Distributions.