Thinking of retiring in Hawaii? The U.S. senior population is soaring. The number of Americans over 65 is projected to nearly double by 2060. Additionally, by 2040, the 80+ population is expected to exceed 28 million, which is more than triple the numbers that same demographic posted in the year 2000.

As the baby boomer generation has grown up, its members have significantly impacted American life. This powerful generation filled public schools and created shortages in labor markets, where they’re expected to leave a large hole as they choose retirement.

Now that baby boomers are reaching a mature age, they’re also expected to have a significant impact on the housing market. Many are moving to homes better equipped to handle senior occupants. For some, this means choosing a single-level home without stairs to navigate. For many, it means downsizing. In fact, 46% of baby boomers tracked in a National Association of Realtors survey were moving to a smaller home.

We’ve certainly seen this trend first-hand. We’ve helped plenty of seniors make local moves to smaller properties, relocate to the Mainland to be closer to family or move to Hawaii to create a simpler, post-retirement life.

Whether you’re executing the move yourself or helping a senior family member, we’ve put together a checklist of seven items for you to consider. By taking care of these items ahead of your move, you’ll be better equipped for a simple, stress-free senior move.

1. Downsize Possessions—as Early as Possible

Everyone intuitively knows that downsizing your home means downsizing your possessions. However, we’ve shown up to move a senior into a one-bedroom condo and found at least three bedrooms’ worth of possessions waiting to get moved. Not only does this mean that the move may cost more than anticipated, but it also means some tricky maneuvers to decide what goes and what to do with the rest. In short, it makes for a stressful Moving Day.

To make your downsizing process easier for (and more effective) for retiring in Hawaii, we suggest:

  • Starting as early as possible: As soon as seniors decide they’re ready to downsize, start looking into options for reducing their possessions. (We’ve got a few tips on this below!) It might take you a few months to clear everything out.
  • Setting up a “dry run” in the current house: If you’re downsizing, visualizing your new space might make it easier to make decisions. Grab a tape measure and some blue painter’s tape. Tape off a few sections of the house to mimic the floorplan of the new home. So, for example, if your current bedroom is a few feet larger than your new bedroom, measure out and tape down the footprint of the new bedroom. Then rearrange your furniture inside the tape lines. This will help you see exactly what will fit—and what won’t.

Getting creative in your downsizing process can also help you get everything down to a manageable size. For example:

  • What can you gift to children and other relatives? Rather than waiting to hand these items down, now might be the perfect time to make these gifts.
  • Can you reduce a collection to one or two special items? If you’ve spent a lifetime collecting Hummel figurines, instead of packing the entire collection, can you choose a favorite (or two?) to take with you?
  • Can you ask internet-savvy family members for help? If you own some truly valuable pieces, you may be able to sell them. We have seen some beautiful collections of solid koa furniture here in Hawaii that were easily sold on consignment. If you have children or grandchildren, they might be able to help with selling items on sites like Craigslist or Facebook Marketplace. (And, hey, if you’re great with computers, more power to you!)

Once you’ve got the downsizing of your possessions underway, there are a few more items we’d suggest to help with a smooth transition.

2. Pack an Essentials Bag

Even if you’re doing a same-day, local move, you don’t want to be hunting around for the important things you need every day. Moving is stressful enough without having to hunt for your toothbrush or your medication.

Instead, pack a bag for yourself as though you were going on a vacation. After all, retiring in Hawaii should feel like the longest vacation ever. Include all of your toiletries and medication, as well as a few outfits. That way, when you get to your new home, you’ll have everything you need for a few days in one place, no unpacking necessary.

This bag will give you some certainty that you’ll have what you need during those first nights in your new home. Those initial days are often the most disorienting. Having the essentials at your fingertips will add some simplicity and ease to your transition.

There’s also another set of items that will help inspire some warm feelings as you get established.

3. Keep Some Happy Memories Close at Hand

Moving is stressful, no matter your age. However, having some familiar items around to trigger happy memories will help you feel settled more quickly.

If you’re downsizing, you may not be able to take boxes and boxes of photos of a life well lived to your new home. However, consider bringing some memories with you in thoughtful ways. For example:

  • Pick and choose enough photos to fill two or three photo albums. Keep them in an easy-to-access place so you can flip through them whenever you want. Put the rest in storage or consider giving them to a family member to keep.
  • Take some framed photos of your family and display them in your new home. You may have to pick and choose the ones that will fit in your new space, but make sure you put them out sooner rather than later.

Having some of these familiar touchpoints to remind you of the relationships in your life can help you transition more easily to a new space. In fact, these little touches might make your new place feel homey more quickly than you might expect.

You might also find it easier to say good-bye to your old home if you give it a formal farewell.

4. Make Some Final Memories Before Retiring in Hawaii

Before your move, consider having friends and family over for one last party. You might even memorialize the event with a few photos you can display at your new home. By bringing loved ones together, you’ll make some final memories—and give yourself the opportunity to say a formal farewell to your old home.

Pro Tip: Get some postcards with your new address printed up from a service like Shutterfly. Have a stack ready at the party for your friends and family. Once you start to get postcards, holiday letters and greeting cards at your new address, it will really start to feel like home.

And while we’re talking about your new address . . .

5. Don’t Forget the Paperwork

When you move, make sure you or a family member notifies service providers and government agencies so you can continue to receive important mail. At a minimum, make sure you:

Pro Tip: Once you move, look for the yellow USPS forwarding label on any incoming mail. This will give you a heads up that the sender still has your old address. Make sure to reach out to update your address for any future correspondence.

Now that you’ve done all of this preparatory work, there’s one other factor that will heavily influence how smooth your senior move will be: your moving company. We’ll give you a couple of tips for finding the right company—and the right services—for your move.

6. Get Three Independent Quotes for Your Move

No matter what kind of move you’re preparing for, we always recommend getting quotes from three different companies. No matter if you’re retiring in Hawaii, moving to a smaller home, or changing islands, you’ll want to adhere to this rule. it will give you the lay of the land for what a move like yours should cost. The quoting process will also give you a chance to get to know each company and choose the one you think would work with you best.

As you go through this process, we suggest also asking for a quote for a “full-service” or “door-to-door” move. When you choose this level of service, your moving company will take care of just about everything. Your crew will show up with everything they need to pack and load your items, then the crew will unpack everything at the other end. They will also assist with furniture disassembly and reassembly, as well. All you have to do is make sure the movers have a clear pathway to get in and out of your house, pack your own valuables and they’ll do the rest.

If you’re a senior moving yourself, a full-service move can be a great option, since you’ll be able to leave all the heavy lifting to your crew. Who wants to kick-off retiring in Hawaii with hard labor, anyhow?

And, finally, we have one more note for you. This one comes from nearly 40 years of experience handling tens of thousands of moves to all destinations for customers of all ages.

7. Expect to Get Emotional

Transitions can trigger deep feelings, especially if you’ve spent many happy years in your current home. It’s hard to leave the familiar behind. Moving to a new home comes with a lot of uncertainty. In fact, it’s one of the most stressful life events you may experience.

All this is to say: Don’t be surprised if you find yourself getting emotional before, during and after Moving Day. It’s all a part of the process. And, in our experience, you’ll find yourself feeling at home in your new space earlier than you think. But don’t worry, retiring in Hawaii means that you’re loved ones will definitely want to come to visit!

Plus, if you’ve followed our tips above, you’ll avoid some of the more common and painful scenarios, reducing significant stress and making for a smoother move to your new home.



Need Some Help with Your Senior Move?

We’d be happy to assist you! Whether you’re headed to Hawaii, moving to the Mainland, transitioning interisland or even staying local, we have crews based on Oahu, Maui, Kauai and the Big Island who can help. Just get in touch with us for a quote. We’ll help you make a simple and stress-free transition to your new home.

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