Is This the Right Moment for Tax Planning?

When you’re nearing retirement or dealing with major life shifts, this question isn’t just worth asking—it might be the most important mment to take action. Because when it comes to taxes, timing isn’t just important—it’s everything. A missed opportunity will cost you. A well-timed decision? That can save you five figures or more.

 Below are six windows you don’t want to miss:

There’s often a 5-12 year window between retirement and when Required Minimum Distributions (RMDs) start at age 73 or 75. This is prime time for strategic planning.

With lower income during these years, it may be possible to level out taxes over time, reduce the size of future RMDs, and prepare for long-term income planning. It’s also a good time to evaluate charitable giving strategies that can help you manage tax exposure while supporting causes you care about. Many  people only start thinking about RMDs when they go into effect and they are getting clobbered with taxes—don’t make that mistake.

Retirement years are uneven. You might work half the year, get a payout, or start living off savings. That irregular income can change your tax bracket—and open the door for smart tax strategies. You need to have a tax smart plan for how you will spend your assets as you enter retirement.

You also have important decisions about when to start drawing Social Security. This is a decision that should take into account the earnings and life expectancy of each spouse. Before Social Security starts, you may be in a lower-income year than usual, which can affect how much of your benefits are taxed later. This window is brief, but it matters.

Yes, the early bird gets the worm! This is your final stretch while earning full income. That usually means you’re in a higher tax bracket—so you still have room to act before everything changes.

This period is often the last chance to shift income strategically, take full advantage of retirement contributions, or explore planning options while you’re still in a higher tax bracket. After retirement, many strategies become less effective or off-limits.

Sold real estate? Cashed out investments? Inherited money?

These one-time events can dramatically spike your income and throw off your tax picture. The tax impact often goes beyond just the number on the check—it can affect your Medicare premiums, phase out deductions or credits, and trigger extra taxes like the Net Investment Income Tax.

Timing becomes critical in these years. A windfall can make other income more expensive from a tax perspective. The sequence of when you recognize gains, take withdrawals, or make large purchases or donations can change your total tax bill significantly. This is a year where consultation with a professional can pay off in real dollars.

This is the most ignored opportunity in tax planning. A bad year—job loss, medical leave, income dip—isn’t just hard. It can also open up options that don’t exist in higher income years.

Lower income could create favorable conditions for asset sales, income shifting, or other moves that are otherwise too expensive from a tax standpoint. These years deserve just as much attention as the big ones.

Life changes fast—and taxes follow. If you’re going through something big, your tax strategy needs to adapt.

Divorce, moving to a new state, downsizing, or facing a serious illness in the family can all reshape your tax picture. These transitions often involve a change in filing status, income sources, or asset ownership—each with their own timing considerations.

For example, if your spouse is facing a life-threatening illness, your current filing status may offer one last opportunity to make certain moves before everything shifts.

Tax planning isn’t about doing everything yourself. It’s about knowing when the stakes are high enough to bring in a pro.

If you’re staring down retirement, recovering from a tough year, or dealing with a major life change, the timing might be right. And the sooner you get advice, the more options you’ll have on the table.