If you’ve read any of my columns or seen me on TV, you probably know that I believe getting organized is one of the things that can really help people live a much healthier happier life.

However, a few years ago I began noticing an unusual trend. As baby-boomers began to move into their retirement years, more and more people started asking me for help with downsizing a lifetime’s worth of possessions. Often times those requests came from the adult children of the retirees who were concerned with how they’d deal with their parents’ stuff.

Frankly, they were frightened at the prospect of dealing with their parents stuff when they already were struggling with their own over-stuffed homes—but at the same time they were equally frightened at the prospect of disrespecting their folks or creating problems in their extended families.


Because of that, earlier this year I wrote and released a book called Let It Go: Downsizing Your Way to a Richer Happier Life. The book is a practical guide to help you and your loved ones figure out the best way to handle your parents’ stuff in a way that will not lead to sadness or loss but instead will bring even more joy to a family.

Here’s some of what I’ve learned in doing research for the book:

Start the Conversation Early.

It’s too late to start the discussion of downsizing once a crisis has hit (health, financial, or otherwise). The better path, instead, is to gently introduce this topic regularly over family meals or in casual conversation. Make sure you get your siblings involved early, too This will get your parents thinking about how they would like the things they own to be used or dispersed among family or friends or to a worthy cause.

It’s good not only to hear what your parents are thinking, but also to initiate this important family discussion. In this way you can short circuit possible problems and avoid possible hard feelings in the future. Dealing with everyone’s concerns now is the only way to go.

Woman adjusting picture frames

Be Sensitive to What Your Parents Have Gathered About Them.

While many of your parents’ things may not look like they have significant emotional or sentimental meaning, to your parents they are the measure of their lives’ work , their successes and milestones.  The things they own represent the families they’ve loved and raised.

While you may be talking about downsizing, what they might be hearing is you say you don’t value the life they’ve lived. So be sensitive and gentle so as to avoid falling into a trap of simple miscommunication and alienating them.

Be Creative in Your Suggestions.

In my experience what can be an initial experience of angst about letting go of things can be substantially softened if you recommend some practical and creative strategies of how to do it. For example, something as simple as labeling larger items with the name of the intended recipient or making lists of items your parents would like to pass on to others now can get your parents less concerned about trying to remember who was promised what.

Simple lists can also go a long way to reducing the burden on whoever has to deal the estate after your parents are no longer able to. Also, consider your parents’ favorite charities or causes – these organizations may be very happy recipients of some of the items your parents own and welcome a generous donation to their cause. Suggesting that items are going to good homes where they will be valued and used reinforces the idea that what they own will be used well and softens the idea that not everything of theirs will be moved to the homes of other family members.

Old hands hold an antique pocket watch

Find What’s Most Important and Focus on That.

Finally, remember that through this process it’s the ‘treasures’ that are most important. The treasures are the few most significant things which mark the most important memories, achievements or moments in a person and a family’s life.

When dealing with a home full of possessions, it’s very easy for anyone – especially older people – to become overwhelmed and often paralyzed, unable to make any decisions. By first identifying the treasures in a home you can help your parents differentiate the most significant from the less important. Helping them create this distinction goes a long way toward them clearly seeing what is important to hold onto and what they can more easily let go of.

Bottom line: Be gentle but be direct. Talk frankly about your concerns. Establish from your parents what’s really important.

I’ve worked with so many people who didn’t have this conversation and ended up inheriting a full home’s worth of stuff having no real idea what their parents thought was valuable or significant and what was simply ‘the rest’. Having this discussion will not only establish what’s important to your parents and involve the whole family in the process but will also help you avoid a sense of guilt of not honoring your parents’ memory in an appropriate meaningful way.

Sometimes the most difficult conversations end up being the most rewarding. I wish you and your family much happiness toward this important endeavor.

Peter Walsh