1. How will your retirement affect your adult children (or other family members)?

Whether the day of your retirement will mean the closing of the Bank of Mom and Dad or the termination of on-call babysitting services, you should talk with your family about how your retirement will change the family dynamic.

If you’re going to downsize, point out that you won’t be the ones hosting the annual holiday get-togethers in the future, and that there won’t be a spare bedroom in the new condo in Aspen because that’s going to be the room where you make stained glass.

It might not occur to them, either, that there may not be a house to inherit if you’re planning on traveling around the world and taking short-term rentals when and where it suits you.

5. What do you both want out of retirement?

This is one chat you need to have with your spouse or partner, and before you both get too deep into planning to be able to shift gears. Otherwise, each of you could be in for some pretty unpleasant surprises.

What if you expected to globetrot while she was looking forward to extended gardening sessions, or even launching a second career—or vice versa? Or what if you both have ambitious postretirement plans, both requiring a pretty sizeable infusion of capital?

You’ll need to put your heads together and figure out how, and who, will deal with making sure they’re both given a fair shot, in both money and time.

4. Should you downsize? If so, how much, and when?

This is another conversation that needs to happen well in advance of retirement. If downsizing turns out to be something you both agree on, you can get a jump on it even before you leave the workplace.

That could save you some serious money both now and in retirement, which will make your retirement savings last longer. However, before jumping in with both feet, you need to decide jointly on which aspects of your lives, if any, should be cut.

Want to eliminate the car? What if he hates walking and biking everywhere, or finally ’fesses up to being too fatigued or in too much pain from arthritis to want to be that active? What if she plans to volunteer at a shelter and needs to haul supplies?

3. Are you both really ready for retirement? If not, what can be done to make it happen?

This is how you decide when you’re ready to shake off those shackles for good—jointly. Do you both have a good grasp of what it will cost to live in retirement, and where the money is coming from to pay for it?

Or do you need to discuss the possibility of continuing to work, at least part time, to make it come out right? Will you retire together, or is one partner absolutely fed up with working? If so, how soon will that day come, and how long will the other continue to work?

2. Should you freelance or consult after retirement?

This is the conversation to have with your boss, particularly if you anticipate either boredom or a need for additional income after retirement. In addition, if one of your goals was to launch yourself into business, or to do some long-anticipated modernization on your home, the continued business ties with an employer pleased to continue the association could go a long way toward making that happen.

But if you’re going to keep working in retirement, check out fair fees for someone with your experience and background. Go into the conversation as well informed as you can.

1. How will your retirement affect your adult children (or other family members)?

Whether the day of your retirement will mean the closing of the Bank of Mom and Dad or the termination of on-call babysitting services, you should talk with your family about how your retirement will change the family dynamic.

If you’re going to downsize, point out that you won’t be the ones hosting the annual holiday get-togethers in the future, and that there won’t be a spare bedroom in the new condo in Aspen because that’s going to be the room where you make stained glass.

It might not occur to them, either, that there may not be a house to inherit if you’re planning on traveling around the world and taking short-term rentals when and where it suits you.