How to sell it all and move to Hawaii

Ready to sell it all and hit the beach? Here’s how to sort through your stuff without losing your mind! 

Donate. Sell. Ship. Pack. 

This shouldn’t be too difficult. I just have to sort through everything I own. I just have to sort through EVERYTHING I OWN! Let the hyperventilating commence! 

Many people ease into a big transition, like say, selling everything and moving to Hawaii. I’ve never been an “ease into it” kind of gal. 

Which is why I found myself having a full-on panic attack as I stood in my apartment in a sea of belongings. Perhaps emptying out all my closets and disrobing my shelves in one fell swoop wasn’t the best approach to deciding what to do with my possessions. I don’t suggest it actually. But you don’t have to lose your mind along with your belongings while preparing for a big move or a nomadic life! You just need a few guidelines: 

Have labels on hand so you can assign your possessions to their proper destination: Donate. Sell. Ship. Pack (bring on the road or plane). These were a good starting point for me. I later added a fifth label, “Undecided.” Over the course of a few months, make note of what lives in that pile, and how frequently you use it. Chances are, if you remove an item from the “Undecided” pile to use it within a week, you should probably bring it with you. If a month has passed, and an item is collecting dust and generally looking forlorn, give it a new home! 

Go room by room to avoid a flood of panic! Grab some Rubbermaid totes and those labels of yours, and label them as “Donate” and “Sell” and so on. Then commit to going through one or two rooms each week and sorting through the drawers and closets and nooks and crannies, deciding the destiny of that rooms’ stuff. 

What about anything I will need to use before I make the big move? Glad you asked! I had a walk-in closet in my New Hampshire apartment that I emptied out for this exact purpose. Anything I wanted to bring on the trip (other than perishables and toiletries) but couldn’t pack just yet was waiting in that closet. 

Feeling sentimental? I definitely struggled with this one! Certainly, I couldn’t donate or toss the framed photo of my grandmother! Belongings like this will most likely be as valuable to a friend or family member as they are to you. In the case of the photo, I gave it to my sister, who I know will cherish it as I have. 

Almost ready to ship off to their new homes!

Still feeling indecisive? I’ve been there! When you revisit that “Undecided” pile, ask yourself the following questions to determine if that slow cooker or this pillow belong on the road with you: 

Is it practical and functional? If your life move will take you anywhere north of Mississippi, you probably want to find a place for that Patagonia puffer in your van!

• Consider where and when you will be traveling, and how you will meet your basic needs in that location, depending on the season! If you will be traveling to the Canadian Rockies, don’t leave those practical wool socks behind. And definitely pack the camera if you’re going to camp across from an active volcano in Guatemala. 

• Did I purchase this item within the past six months? If so, was it to meet a need? As I took stock of what I acquired over those six months in New Hampshire, I realized that I actually lived happily without most of them before I brought them home. Like that bookshelf. However the coffee maker I replaced is an exception... and a purchase that met my need to actually function each day! 

• Do I use this at least once a week? If so, will I still use it once a week if I’m living in a van on the road or a studio near the beach? For example, will I use my tall leather boots that I wear to the office? Not likely. 

• Did it come at a high price? It may be hard to part with your high-end blender simply because it cost the equivalent of a months’ worth of groceries. I made a general rule for items such as this as I sorted through my belongings – To make it onto the “Pack” list, something had to cost over $400, be used at least once a week, and be small enough to fit in my compact future home. Anything that did not meet all three requirements would move over to the “Sell” list. 

Make some money. Or make a difference! You’ve determined what you will sell and what you will donate, so now what? Selling your stuff online is a fantastic option for anyone who doesn’t mind making the occasional run to the post office. I’ve had great success with sales on EBay and Poshmark. 

For furniture and anything large, consider using CraigsList and finding a buyer locally. As your date of departure approaches, don’t be alarmed if you still have furniture that remains unsold. Contact a consignment shop for a convenient way to sell your couches (and still make some money). Or reach out to the Habitat for Humanity in your town and arrange to donate your furniture and home goods to their Re-Store. Trust me, they’ll be greatful! 

My local consignment shop has been excited to take those high-end suits and dresses off my hands, since I won’t be needing those in Hawaii! I’ve donated any remaining articles of clothing to womens' shelters in my community, and deposited pairs of shoes and piles of books into the yellow donation bin outside my gym. 

Stop! You heard me. Stop! Plop yourself down in the middle of that pile and close your eyes. Picture yourself in your new life. How do you want to feel when you wake up every morning? What are you surrounded by, other than perhaps some stunning mountains, or the expanse of the ocean? Once you’ve hit reset, return to your sorting with that image in mind! 

Pare down. Then pare down again! Well, you’ve successfully sorted all your belongings into Donate. Sell. Ship. Pack. And your sanity remains in tact! Congratulations! But you STILL own more than you can fit in your van, suitcase, or backpack don’t you? I thought so. This is a great time to re-examine what you’ve piled into those bins. You’ll likely discover that it becomes increasingly easier to part with you possessions once you get the hang of it... And get closer to the day you’ll hit the road! 

Remember that this WILL be worth it! What you are giving up will be a small price to pay for the adventures ahead of you!

Finally made it to Kona, Hawaii! Let the adventures begin!