How to Downsize as Smoothly as Possible

Are you thinking about downsizing? We work with downsizers all the time, and there is so much more to consider than you could possibly imagine… which is why we’ve created a detailed guide with everything you’ll need to know!

Every stage of adult life brings about compelling reasons to downsize. While no downsizing effort is ever comfortable, there are many ways in which you can smoothly address the process.

By following these steps, your downsizing process will be less painful, less tiring, and possibly even joyous.

1. Start The Process Ahead of Time

If you know well in advance that you will be downsizing, don’t wait. Start the process today.

By starting early, you’ll facilitate the process, you’ll also have more time to sell large, valuable items for a better price, and you’ll be less stressed out.

To begin, grab a notebook or note-taking app, and start taking inventory of ALL of your belongings.

As you take inventory, make sure you take lots of pictures too. These help you remember all the things you have around the house. Also, the pictures can be used to preserve memories of precious items you may need to get rid of.

Once you’ve taken inventory, highlight those items that your friends and family members have “stored” in your home, as well as large heirloom items you planned on passing on to family members.

Next, start calling your friends and family members and ask them to pick up their possessions. And if you were planning on willing large and bulky heirlooms, such as a grandfather clock, consider gifting them now.

Then, start going through all of your archived documents. Store away important ones such as deeds, wills, power of attorneys, passports, military records, etc. Keep them safely stored away in a safe or secure file cabinet, and let a trusted family member know where they’re located.

Shred or burn documents you don’t need, such as old canceled checks, receipts, magazines, bank statements, etc. If you find a document you’re not sure whether you should get rid of, consult your tax attorney.

If you have more than one vehicle, consider keeping just one. Besides downsizing to a smaller home, getting rid of a vehicle (or all of them) could lead to large monetary savings. 

In fact, according to AAA, if you factor in depreciation, fuel, insurance, and other car ownership expenses, it costs around $8,558 a year to own an average sedan in the US.

If you and your spouse are retired, you may be able to get by fine with just one car, and supplementing its usage with public transportation. And depending on where you’re moving to, you may not even really NEED to own a car.

If getting rid of vehicles isn’t an option, consider downgrading to more affordable ones with better fuel efficiency.

Lastly, pay off your debt as quickly as possible (the waterfall payment method is a time tested strategy to get rid of credit cards and other bad debt).

And for ANY expense you need to have in the future (there will be many when it’s time to actually move), live by this old school rule: if you can’t pay for it in full right now, you can’t afford it.

2. Keep in Mind Where You’re Going

Keeping in mind your new home is extremely important since it will determine how extensively you need to simplify your life.

For example, if your new place doesn’t have a yard, there’s no reason to keep any landscaping tools. Or if you’re downsizing from a 3-bedroom home to a 2-bedroom one, there’s no need to keep more than 4 or 5 sets of sheets and linens.

At the same time, focusing on your new home and thinking about all the new and exciting memories you will create, will be of great psychological help. Moving is always a difficult experience, especially if you lived in your old place for decades, and you have tons of memories tied to the place.

3. Start With the Small and Easy Stuff

There are certain places in the home that accumulate more clutter than others. Places like the garage, the attic, and the basement.

However, don’t feel like these places need to be the first ones to be decluttered. Not only do these places tend to be very uncomfortable during the summer and winter, but these places tend to accumulate a plethora of items with emotional attachment.

From abandoned hobbies to holiday decorations, these places end up holding all the stuff that you just couldn’t bear to throw away in previous decluttering efforts.

Start with areas of the house with little to no emotional attachment, such as the laundry room, linen closet, yard or home gym.

Pro Tip: If your treadmill, Bowflex, or similar exercise equipment has become a glorified clothes rack, you probably won’t use them in your new home. Get rid of them. If you’re planning on staying physically active, join a gym instead!


By going through those rooms first, you’ll make immediate progress, and you’ll be more inspired to keep that momentum going.

4. Scale Up Your Effort

Now that you’ve gone through the easy(-er) stuff, it’s time to tackle the harder stuff.

Before you begin, it’s essential to define the difference between wants and needs.

Needs are things you cannot live without. Stuff like clothing, medical supplies, work tools, eating utensils, etc.

Certain items aren’t TECHNICALLY needed but are very precious and irreplaceable. Stuff such as engagement rings, photo albums, deeds, diplomas, etc. You CANNOT afford to throw out.

Finally, there are other items you should keep because they make life A LOT EASIER, and get plenty of use. These could include toasters, blenders, coffee makers, crock pots, side tables, etc. If they are still in good shape and fit in your new home, it’s a good idea to keep them.

Anything else that doesn’t fall into these three categories could be considered “luxury” wants.


Pro Tip: If you’re helping elderly family members downsize, consider helping them move away early, so they don’t watch their beloved home being taken apart item by item.


While it’s important to know the difference between needs and wants, that doesn’t mean that you should be overly strict about it.

You want to simplify, not live like a monk.

However, if you want a successful downsizing, you do need to draw a line.

When deciding whether you should keep an item or not, try asking the following questions:

  1. Do I NEED to keep it, or do I just WANT to keep it?
  2. Does it hold sentimental value? Why? Is taking a photograph of it enough to keep its memory?
  3. How often do I use it? Has it been months or even years since I used it last?
  4. Do I have any other item that performs the same function, possibly even better?

And as William Morris says “Have nothing in your house you do not know to be useful or believe to be beautiful.”

When answering these questions, be honest with yourself. Make sure you also include your spouse and family members in the decision process.

As you begin to separate items into items to keep and items to get rid of, you may be tempted to keep a “maybe pile”. Don’t give in.

More often than not, the maybe pile ends up getting larger than both the “yes” and “no” piles combined, and you actually end up slowing down or even stopping your downsizing efforts.

5. Find a new home for items you’re not keeping

Moving is expensive, especially if you hire a professional mover. The fewer items you take with you, the more affordable your move will be.

Once you know which items you will be getting rid of, you can find a new home for them.

Some ways of doing so include:

Hold a Yard Sale

The old-school yard sale still works. Not only does a yard sale help you get rid of clutter and make a bit of cash from your efforts, but it also places the burden of transporting the sold items on the buyer.

For best results, pick a yard-sale date that is convenient and likely to have pleasant weather.

Before planning your yard sale, make sure you check with your neighborhood association or city zoning regarding requirements for a yard sale.

And to draw the largest number of buyers as possible, invest in some signs. Place them around the neighborhood a few days in advance, and let everyone in your social media circles know about your yard sale.

Give Away Items to Friends and Family Members

Make a list of items that didn’t sell in your yard sale, and let your friends and family members know. They may be willing to take some of that stuff with them.

Donate to Charities, Schools, Day Care Centers, Etc.

If you still have lots of items in great condition that you couldn’t sell and your loved ones had no use for, consider donating them.

Check on Google for charities, toy banks, and other places willing to accept them.

6. Say goodbye to your home

Take your time saying goodbye. It’s ok to bask in nostalgia or to even shed a tear or two. Take pictures if you must. Even creating a beautiful album of photos of the home throughout the seasons, holidays and special moments captured while you were there will make a great coffee table book for your new home while holding onto the memories of your last one.

It’s extremely important that the entire family supports each other during the downsizing process.

But once it’s time to say goodbye, the goodbye should be final. It’s ok to feel sad, but don’t lose focus on all the exciting things to come in the future. Focus on the fact that it’s a new and exciting beginning, not just the end of an era.

7) Make the transition

No matter how smoothly you managed to make the downsizing process, it won’t feel like home right away. Once you get to your new place, make sure you unpack those items that make your new home feel more comfortable and more familiar.

At the same time, the move-in day should be a happy event to share with friends and family, even if you’re getting help from professional movers. 

Be sure to accept help from any family member or friend willing to help out, even if it’s just bringing food and snacks.

Try to keep the entire occasions happy and optimistic.

The adjustment process is, of course, a process. It takes time to adjust, and you can’t just rush it. Keep communication open with friends and family, but don’t overdo it either.


Downsizing is an excellent idea with lots of benefits. But it’s not a process that needs to be rushed. If you take the steps needed to make it as smooth as possible, you help make the process feel less painful.

About the Author

Joshua Stephens is the founder and president of Moving Greater Boston and a Vice President of Berkshire Hathaway Home Services Warren Residential. After graduating from UMASS Amherst with a degree in psychology in 2008, Josh dedicated five years to social service work on the North Shore before joining Berkshire Hathaway in 2013, where he found his professional calling and quickly distinguished himself as a motivated innovator capable of synthesizing the needs of buyers, sellers, investors, and developers. In just a few short years, Josh formed Moving Greater Boston and achieved over $100 million in sales after only 7 years in the business. Josh's team has been consistently recognized at both the local and national levels, receiving numerous prestigious awards for sales and customer service. Last year, the Moving Greater Boston team was awarded the coveted Chairman’s Circle Platinum award for all of Berkshire Hathaway Home Services, which recognizes agents and teams that are in the top 1% for sales across a network of over 70,000 agencies. In 2017, Josh was also personally selected to serve on the Berkshire Hathaway Home Services National REthink Council, an honor bestowed upon only 15 agents among thousands of applicants. Despite his many and ongoing successes in the world of real estate, Joshua has never lost sight of his social work roots. A compassionate and principled professional who knows the value of strong communities, Josh continues his advocacy outside of the office by being actively involved in a number of local organizations and charities. In 2016, he was instrumental in conceptualizing and developing Business Networking International (BNI) Prospect Hill, an organization that connects local business professionals and aspiring entrepreneurs. As a native of Massachusetts, Joshua has an intimate knowledge of Boston real estate, while having a degree in psychology helps him to understand each of his clients' unique needs, enabling him to connect them with ideal communities, an opportunity which he considers both a priority and privilege. Rather than simply facilitating the buying and selling of property, Josh views his role as a realtor as a lifelong commitment to continually serving the best interests of the people who have put their trust in him. Josh continually strives for excellence in service, provides in-depth knowledge of the market, and blends unwavering integrity with amenable good humor to alleviate the stress of real estate transactions and assure the experience is one that lets the sensation of being in the perfect place, at the perfect time, truly resonate.