10 Questions to Ask When You're Thinking About Downsizing

Start with what you want daily life to look like. Are stairs, yardwork, or repairs taking more energy than they used to? Would you like to be closer to friends, family, or the things you enjoy? You can start exploring while you still feel comfortable at home and have time to make decisions at your own pace.

Pick the question that's weighing on you most. If it's money, start with an estimate of what your home could sell for. If it's where you'd live, tour a place that interests you. If it's your belongings, start with one drawer or closet. One answer can make the next decision easier.

Picture an ordinary Tuesday. Where would you walk the dog? How would you get to the grocery store or see friends? Would you rather have a smaller home to yourself or a community with meals, activities, and neighbors nearby? If you're touring senior living communities, ask what's included and what support is available if your needs change.

Ask for a seller net sheet that estimates what you'd keep after selling costs and any mortgage payoff. Then compare your current expenses with the full cost of your next home, including any deposits, monthly fees, and services you'd pay for separately. Those numbers give you and your financial advisor a starting point.

Moving first may be an option. It can give you time to settle in while your home is being prepared for sale. The decision comes down to what you can comfortably carry if the two homes overlap. I help families compare both timelines and, when a senior living community is involved, coordinate with its team around the move-in date.

I'd walk through your home with you before you spend money. We'll look at what buyers in your market are likely to notice and what's worth the effort. In some homes, clearing rooms and making a few repairs are the best places to start.

Start with what you want in your next home. A floor plan can help you see which furniture fits. Ask family members what they'd genuinely like to keep, then decide what to sell, donate, or pass along. If sorting everything yourself feels like too much, a senior move manager or organizer can help.

Tell them what you're considering, what you're unsure about, and where you'd welcome help. You might say, “I'd like you to tour a couple of places with me. I'm still deciding what feels right.” Giving everyone a role can make the conversation easier while keeping your wishes at the center.

Give yourself time to say goodbye. Take photos of the rooms you love, invite family over for one more meal, or choose a few things you'll enjoy seeing every day in your next home. You can look forward to a move and still miss the home you're leaving.

Through Collective Moves, I help with home valuation, sale preparation, and timing. I can also connect you with professionals for organizing, estate sales, senior living, and legal or financial planning. We work with senior living communities to offer educational seminars, so you and your family can ask questions while you're still weighing your options.