Downsizing without overwhelm: Elinor Warkentin on starting small and keeping the decisions yours

Interview by Ken Gardner for Fruitful Years

Start with one manageable area and the belongings that are easiest to decide about. You do not need to settle the future of every sentimental possession before making progress.

Elinor Warkentin of Goodbye Clutter! helps clients with downsizing, decluttering and estates. In this interview, she explains how to break the work into smaller decisions, involve family without applying pressure, and clarify expectations before hiring help.

This interview has been edited for length and clarity from Elinor’s written answers. It offers general organizing guidance, not individual legal, financial or medical advice.

1. What is a useful first step when downsizing feels overwhelming?

Elinor: Overwhelmed is a word I have heard frequently in more than 25 years of helping clients downsize. Know that you are not alone, and that help is available if you want it.

Start with the easy decisions: items you know you do not want, things that are old or broken, and belongings without a strong emotional attachment. You do not have to begin with the hardest possessions.

Break the project into chunks. That might be one room, one closet or even one drawer. Approaching one small piece at a time makes the work more manageable, including when a move is not yet scheduled.

2. How can someone decide what to keep when possessions carry memories?

Elinor: Think of your belongings on a spectrum. At one end are the possessions that hold your most important memories. At the other are things you once loved but that no longer have the same meaning for you. Practising with the easier decisions can help you become more comfortable with the process and learn to trust yourself.

Look at items one at a time rather than only as a whole collection. Someone might initially feel that every book must stay. Going shelf by shelf can make it easier to notice individual books they no longer want, without having to decide the fate of the whole bookcase at once.

I tell clients, “It’s your stuff, your decision. You can change your mind until ‘the truck drives away’.” The intention is to take some pressure off the process.

Couples should not make these decisions for each other, and one family member should not decide for another. Nor should I. Pressure can damage trust and make people hold on more tightly. An impartial professional can listen to the story behind an item and help someone work through a decision. Look for someone who respects both you and the process.

3. What sequence helps when a smaller home is involved?

Elinor: Measuring the new space is key. Identify any belongings you feel you must take, and check whether they will fit.

Sorting can happen in two stages. First, identify the things you do not want. Then consider whether what remains fits both the available space and the home you want to create.

4. How can family members help when they disagree about belongings?

Elinor: Respect the owner of the item and give them room to decide. Have a clear conversation about belongings that might be passed on to family or let go.

It is a two-way conversation. If a child particularly wants an item, encourage them to say so and make that preference known in your planning. If they do not want something, they should not be made to feel guilty or forced to take it.

It is not always easy, but being clear at the start is better than assuming everyone has the same wishes.

5. What should someone ask before hiring an organizer or downsizing service?

Elinor: Ask about experience. People enter and leave the field within a year or two and anyone can call themselves an organizer, so find out what relevant experience the person brings.

I use a Letter of Agreement; some organizers use a contract. Ask whether they provide something in writing, and whether they are transparent about their rates, cancellation fees, insurance and privacy policy.

Explain your priorities, including your budget, timeline and values around reuse and recycling. If you have preferred destinations for belongings, say so. Discuss the work you want help with rather than assuming the organizer has the same priorities you do.

Editor’s note: Before agreeing to a service, clarify in writing what is included and who is responsible for selling, donating, disposing of or transporting belongings. Elinor’s answers do not establish that every organizer provides each of these services.

6. What could a realistic first week involve, and what makes the process harder?

Elinor: A first week might involve walking through the current home, reviewing the timeline and scope, and discussing a strategy. The practical work should begin at the client’s speed, in an area they choose. Get feedback after the first session so that you can check whether the process is working for them.

Not planning first is one mistake. Clients may not know the available options, which belongings might have monetary value if selling is important, or which skills an organizer can bring. A good organizer can explain the stages ahead and ask questions that help the individual plan. Planning can save time, energy and money.

Another difficulty is leaving decisions until circumstances make them urgent. Over the years, possessions can accumulate long after they are useful: work clothes, professional books, paperwork, entertaining supplies, photo albums and household linens. A later change in health or living arrangements can make sorting a home harder.

Consider what you use, love and value now. Clearing what you no longer need can leave a more manageable home and fewer decisions hanging over you.

Less is more. Except with chocolate.

About Elinor Warkentin

Elinor Warkentin says she has helped clients downsize and declutter for more than 25 years. Her supplied biography identifies her as a member of Professional Organizers in Canada since 2003 and a Platinum Leaf member. Goodbye Clutter! also has a team she calls Organizing Angels for larger projects, including estates. Her approach emphasizes ethics, communication and helping clients “make room for what matters.” She enjoys chocolate, travel, photography and storytelling.

Website: Goodbye Clutter!

A manageable next step

Choose one small area with relatively easy decisions. If you want professional help, write down the work you need, your timing and budget, and the questions you want answered before you agree to a service. Keep the owner’s choices at the centre of the process.

Editor’s separate reading suggestions: If a keepsake prompts a story you would like to record, explore the family-history activity. For a different small everyday activity, browse the Seven Ideas printable. These are optional Fruitful Years resources, separate from Elinor’s answers; the owner still decides what happens to their belongings.

Editor’s separate reading suggestions: If sorting belongings is part of a change in daily life, Karen Carr’s retirement interview explores routine and identity in retirement. For a small social step alongside the practical work, the social-connection guide offers a way to plan repeatable contact. These are separate perspectives, not promises about the outcome of downsizing.