Of all the rules, advice and complicating factors you have to account for with wealth management and retirement planning, one of the toughest to get a handle on is the issue of timing. Because when you do things is sometimes as important as what you do with regard to your investment and retirement decisions. Timing issues with your 401(k)/IRA are among the most confusing—and, naturally, also some of the more important. The biggest issue is that there are very different rules for different types of accounts. Some accounts have windows in which you can or must take certain actions, and other accounts have hard deadlines. Those rules are unforgiving, and missing those windows/deadlines can have some costly implications. One of the biggest issues that many people try to navigate around is the costly 10% early withdrawal penalty. You can avoid that penalty if you wait until the age of 59 ½ to take out funds, but be careful! That deadline is calculated based on the exact day you turn 59 ½, and withdrawing funds even a single day early can expose you to the penalty. What makes this confusing is that this is in contrast to the way the 55-year-old separated-from-service 401(k) exception is determined. That deadline is much more flexible: if you separate from service anytime in the year you turn 55 or older, you can make penalty-free withdrawals. Just to make things extra complicated, the fairly stiff penalties that apply to those who fail to make withdrawals before they turn 70 ½ years old use a different timeframe calculation. You have until April 1st of the year following the year you turn 70 ½ to make your withdrawals. The bottom line? Do your research, consult a trusted financial advisor…and invest in a calendar!