Helping someone you love transition into the next phase of life is one of the greatest gifts you can give. It’s also, frankly, a lot of work. Below are a few tips to help make the processes more efficient and enjoyable.

Start immediately, earlier if possible

It can easily take months, sometimes longer, to downsize a lifetime of memories and possessions. While some people find downsizing fun and liberating, to others it can feel physically and mentally draining. Starting early can make all the difference. It gives everyone, you included, the time to take things in bite-sized chunks and ease into the process and the decisions. It lets you start with the easy steps, take breaks when needed, and builds in time for inevitable hiccups and delays along the way.

Start by making a running list of all the key items in the home. Pay special attention to furniture and to items such as books, records, tools–anything that is either a “collection,” is heavy or awkward, or might have value (either sentimental or monetary). Prioritize coming up with a plan for these items first, as they can be the most tricky to pass on in ways that feel comfortable and correct to everyone involved. 

Create a vision for the new space

As you are looking at what to keep and rehome, really consider the life your loved one wants to live going forward–and the specific layout and dimensions of the new space. Come up with a plan. Make every item earn its place in the new home, either because it’s deeply loved or because it will support the new lifestyle and future opportunities. 

To get a clear sense of how everything will fit, especially if the new space is significantly smaller, you might consider using a free room planning software application. 

Be realistic about the resale value of furniture 

Unless you have bonafide antiques, you may be disappointed by the price your furniture fetches in the secondhand market–even when it’s in excellent condition. The simple fact is that the main value of your furniture is its value to you, not a monetary sum. While this can be hard to accept, once you do, it can make the process of getting rid of items simpler. You might choose to try to sell some items, but realize that often the “hassle factor” of trying to max out what you’d earn by selling everything negates any compensation you might get from doing so. The earlier you start this process, the less stressful it will be. You’ll be able to take your time and ensure that everyone is comfortable with where the items land. 

If you haven’t done this already in Step 1 above, start by listing all of the significant furniture pieces in the home. As you figure out your plan for each, note it next to the item. Set out a rough timetable for when you’ll need to take action on each, what that action is, and when it needs to be completed. Common actions include:

•  Take to the new space
•  Give to a relative or friend
•  Sell directly via Craigslist, Facebook, or other source
•  Donate to a charity or other organization 

Pro tip: If you are thinking of gifting items to others, be sure to confirm they want them sooner rather than later. Many in today’s younger generations aren’t emotionally attached to family heirlooms and keepsakes, preferring to go through their lives with fewer possessions.

Digitize memories

Digitizing preserves memories by making digital files of them that work on today’s cellphones, tables, computers, and other modern technology. Digitizing protects and preserves memories from simply degrading over time. But that’s just the start.

Putting keepsakes into digital form lets you easily enjoy and share them right now. This is particularly true for formats where the playback mechanism is cumbersome or obsolete, like video tapes or film. But, it's also true for photos, thanks to digital photo frames and online photo resources like Google Photos. Digitizing also lets you backup your memories —on the cloud, on drives, in multiple places—for peace of mind.

Want to know more? Curious about where to start? 

Come up with a backup plan

This is particularly important if you have a hard-stop end date. What if you get to that and there are items left? Having a charity or estate sale or other resale organization set up to take furniture items is one option. Or maybe you do a “fire sale” where everything must go quickly (and thus likely cheaply). But what about smaller “stuff”? If you can see that you maybe not be on pace to get everything taken care of in time, definitely pause and make it a priority to set up a backup plan. You’ll be glad you did.