Joyce and Harry Yates have lived happily on the same sprawling property in rural Campbellville, Ont. for over 30 years. But these days, their beloved home is proving too difficult for the 90 and 92-year-old to manage on their own.

“It's just gotten too big for us,” says Joyce.

So, this fall the two will be moving to a smaller bungalow in Milton where Harry can still garden and Joyce can still golf, and they will be much closer to friends and family.

READ: The Senior Dilemma: What Should We Do With Our Real Estate Investment?

But when you've lived in a home for decades, clearing out things of sentimental value can be a heart wrenching experience. Joyce knows the move was necessary, but admits that going through all of their items and having to part with so many was an emotionally fraught process for both of them.

“I don't think for a moment that I could've done it all myself,” says Joyce. “I needed help, so my family decided what I should take and what I should leave behind. I found it very stressful.”

Strategies for Sentimental Value

Pauline Duhart, co-founder of Simply Home Downsizing, works with people like Harry and Joyce all the time. The company is designed to make moving as painless and turn-key as possible.

Simply Home Downsizing does everything necessary to get you into your new home.  All your stuff is unpacked, all your furniture is where you want it, all your art is put up on the wall and your bed is already made without ever having to lift a finger.

Part of that process means de-cluttering and organizing the old house before Duhart even starts to pack and unpack.

“People have an emotional attachment to their items,” explains Duhart. “And as a result, they feel that the item they're parting with has more monetary value than it actually does.”

As an example, Royal Doulton figurines were a popular purchase in the 1980s. People were spending $400.00 each in the hopes that the items would grow in value and they could pass them down to their grandchildren. These days, the figurines are worth about $40 second-hand and it's Duhart that has to break the news to her clients.

READ: If You Marie Kondo’d Stuff, Here’s Where To Donate Your Komono In Toronto

“I say to my client, 'I understand the sentimental value these items hold for you. But you've got 50 of these figurines and you're moving into a 600 square foot apartment. You know you can't take them all, so let's talk about picking your favourite and parting with the rest,” she says.

Sure, it's a difficult conversation, but once her clients know they're being heard and their feelings are being taken into account, they tend to think more practically, especially when there's a deadline approaching.

If you find yourself emotionally attached to and having difficulty parting with items, Duhart recommends these steps:

Step 1:

Label the items you want to keep for yourself and cannot part with.

Step 2: Look again and ask yourself, ‘What items here are sentimental, but can be gifted to family and friends who will cherish it’?

Step 3: If your family doesn't want the items or you don't have the space, consider donating them to organizations that will actually appreciate it as you have. Don't be afraid to think outside traditional donation centres either.

“I had a client who had a lot of pottery,” recalls Duhart. “She belonged to a potter's association, and so she donated all of the items to them.”

Other ideas include donating kitchen items to a women's shelter or religious items to a church.

Selling Your Stuff, Not Your Sanity

If you're looking to sell your items, this too can be an emotionally fraught process.

Sushee Perumal’s company, MaxSold, makes the selling process during home clear-outs less emotionally taxing by photographing, cataloguing and selling all your items for you as part of an online auction they coordinate and market.

“We don’t just focus on the shiny objects that other auction houses would be interested in,” says Perumal.

MaxSold will sell everything in one lot, including all of the pedestrian items that you usually don't see in an auction. And once your things are sold, MaxSold supervises their removal.

READ: Done Deal! Peerage Realty Officially Acquires Sotheby’s Canada

Like SimplyHome, MaxSold works hard to find buyers who will cherish your items just as much as you did. Plus, if you want to stay in contact with the buyer or be sent photos of the new owners enjoying your item, Perumal can arrange that (as long as the buyer didn't request anonymity).

“Some buyers have participated in video interviews, where we send a videographer into the home just so we can see how an item is being restored,” Perumal says.

The seller also gets final approval of the auction catalogue, so if there's one item they want to take back, they have 24 to 48 hours to change their mind.

Here are some more tips from Perumal on making a move easier on your sanity:

Tip 1 – Don't Procrastinate

Change can be scary for anyone, especially when it comes to moving.  So, Perumal advises tackling it head on:

“Dedicate the time, don't procrastinate, know that the move is coming, get a floor plan of the new home, find out about the area because you're going to feel isolated, so get to know the area you're going to be moving into.”

Tip 2 – Clear Out the Junk

Perumal says getting rid of junk first creates a sense of accomplishment and forward momentum so the rest of the move doesn't seem so overwhelming.

“You start to gain control little by little.”

Tip 3 – Start with the Least Sentimental Rooms

“If you start with the most sentimental items, you can get bogged down and start hemming and hawing over stuff,” says Perumal.  “If you start with the least used items, it so much easier because you don't have the emotional baggage that goes with it. Learn to let go of the little things, so the bigger things become really manageable.”

Tip 4 – Flag Items Strategically

Tackling one room of the home at a time makes things less daunting. As you think about it, start to flag items you're going to keep and items that you're going to sell, to whittle it down little by little.

“It helps the sale of goods go like clockwork,” says Perumal.

Tip 5 – Take Care of Your Health

Do things that promote good health during divestment. And if, after following these steps, you're still finding it extremely difficult to part with your things, don't be afraid to seek emotional counselling. Additional help can be found by contacting Toronto Hoarding Support Services Network.