The moment you realize the house has too much in it
It usually hits you in the garage first, or maybe the basement, when you go looking for something specific and find you can't get to it without moving six other things. Or it's a parent's house after they've passed or moved to assisted living, and suddenly you're standing in four bedrooms of furniture, boxes, and decades of decisions nobody made about what to keep. Springfield has a lot of homes like this: solid brick ranches from the 50s and 60s, split levels from the 70s, farmhouses out past Republic or Ozark that have been added onto twice. These houses have real basements and real attics, and both of those spaces are good at swallowing things for years at a time.
Whatever brought you to this point, the job in front of you is the same. You have to go through an entire house, room by room, and decide what leaves. That's a bigger project than it sounds like from the doorway.
Start with the rooms that got humid or hot
In this part of Missouri, basements and attics do the most damage to stored items, just in opposite directions. A basement that isn't fully finished holds moisture most of the year, especially after the wet spring stretch we get from March through May. Cardboard boxes down there are often damp on the bottom even if they look fine on top. Check anything stored directly on a concrete floor. If it's been there more than a couple years, expect some mildew smell and possible warping.
Attics do the opposite. Ozark summers push attic temperatures well past what's comfortable for most stored goods, and years of that heat cycle break down old plastic totes, dry out wood furniture joints, and turn photographs and paper brittle. Start your room-by-room sorting in these two places, because they'll tell you fastest what's actually salvageable and what's just taking up space.
More on this from household junk dumpster.
Work the house in a real order
Don't try to do the whole house in one pass. Pick one room, finish it, close the door, move to the next. A common order that works: attic or basement first since those are usually the worst, then garage, then bedrooms, then living spaces and kitchen last, since those tend to have fewer big items and more small decisions.
In each room, pull everything into the middle of the floor if you can. It's uncomfortable but it forces a decision on every item instead of letting things get reshuffled into a different closet. Sort into keep, donate, and trash. A fourth pile for
unsure
That's normal, but give yourself a deadline to revisit it, not an open-ended holding pattern.
What you can realistically do yourself
Sorting is homeowner work. Nobody knows what matters in those boxes better than you or your family. Bagging up clothes, breaking down small furniture, and hauling loose trash to the curb on your regular pickup day is also fine for smaller jobs, a room or two at a time.
Where it stops being a weekend project is volume and weight. An entire house, especially one with a full basement and attic that haven't been cleared in twenty or thirty years, produces more debris than curbside pickup is built to handle. Old furniture, water-damaged boxes, broken appliances, and construction leftovers from past projects add up to real tonnage fast. That's when a dumpster rented for the driveway earns its keep: it lets you work at your own pace over several days without making a dozen truck trips to the transfer station on Highway 60 or the county landfill.
A few Springfield specifics worth knowing
If your clearing project overlaps with severe weather season, April through June, keep an eye on the forecast if you're renting a dumpster and leaving it uncovered outside for stretches. Heavy rain on open cardboard and upholstered furniture adds weight and turns manageable loads into wet, heavy ones.
Older homes in this area, especially anything built before the 1970s, sometimes turn up items during a full clear-out that need special handling: old paint cans, fluorescent tubes, car batteries, propane tanks. Those don't belong in a regular dumpster load and the county has separate drop-off points for hazardous household waste. Sort those out early rather than discovering them at the bottom of a pile in week two.