Holy Moly! Downsizing everything you own to fit three people’s lives into a Honda Accord is NO JOKE! This transition has been quite an adventure, and that’s before we even got to the fun, traveling part.
I can see why most people are completely stumped by how this is possible, so I’m going to give you a glimpse into what’s happened over the past 2-3 months to get us on the road and share a few early “lessons learned” too.
Let’s start with our launch timeline…


July- Early August 2018

As I said in my announcement post a few weeks ago, we made the decision to go full “Digital Nomad” in mid-July. We booked our first several months of AirBNB rentals by early August. (Oct-Dec – Hudson Valley/Catskills region, NY; Jan-Mar – Sedona, AZ)
After that the HARD work began. We had to weed through literally everything we owned to choose what would go into storage in Salem, what would come with us on the road, and what would “go away” getting sold/donated/given away.


Late August – Mid-September 2018

So, in August and early September I became very good friends with Facebook Marketplace as I sold tons of our stuff (DVDs, exercise equipment, baby stuff, clothes, etc) We donated a bunch of things to the Epilepsy Foundation that were in decent shape, but not really worth trying to sell privately.
We also made some decisions about a few more valuable items (our virtually new couch), my celtic harp, Brian’s gaming systems. We decided to offer them to be “kept/used” by friends while we’re on the road, so that we can get them back when we come back but they are useful to someone in the meantime.
However, much of what we owned (particularly furniture) needed to be sold or donated. We wanted to keep our Salem apartment functional for as long as possible. After all, we might as well enjoy our things for those last few months, right? In reality, that meant that the last 1-2 weeks were a BIG push of releasing the bulk of the stuff after a couple months of letting go of items just a few at a time. It was hard! There were a bunch of long days and late nights for both of us.


Thursday, September 27th 

This date was our first big milestone because everything that we were putting in storage needed to be packed and ready by this date for our movers to take them away. If I do say so myself… we did an amazing job of downsizing and have tucked the items we’re keeping (mostly sentimental stuff or things that would be more expensive to replace) into a 5’x 10’ storage area.
We even created an inventory using AirTable as we packed with descriptions and photos of the interior of each box that was packed. We did this for several reasons.
  1. To remember what the heck is in that storage area since it might be a while before we see it again.
  2. To be able to find specific items in numbered boxes should we ever decide we really want to grab something again as we pass through town.
  3. For insurance inventory purposes – If the whole place went up in smoke, then we wanted to have good sense of what was in there.


Friday, September 28th 

This day was the brief calm before the weekend’s storm. The goal was primarily to pack everything that we planned to take with us, so that we could “test pack” the car on Saturday morning and ensure that everything we wanted to bring actually would fit into our Honda Accord. I now refer to this process as “Car Tetris.” Good thing I was reasonably good at Tetris in my youth.
I have to say that while that first “test pack” was somewhat disastrously messy, I’m crazy impressed with how well things on this front came together. I spent a lot of time listening to podcasts from other digital nomad families (specifically Extra Pack of Peanuts and Nomad Together were two favorites,) and I learned a lot about the slightly unusual things that we’d want to make sure to bring with us. It was this research that inspired me to create 5 special “kits” (really plastic shoe boxes):
Pantry Kit – Includes small tupperware containers for our most commonly used spices, our favorite expensive oils & vinegars, and our tea collection (because yes, we’re both somewhat picky about our tea, and we like to have a range of options.)
Medicines Kit – A collection of the most commonly used medicines from our bathroom cabinet – all the usual stuff like Tylenol, Advil, Excedrin, and also cold medicine, our heat packs for our sore backs, and care items for Pumpkin like boogie wipes, her Nosefrida, and rectal thermometer.
Dishes Kit – Mostly containing baby-related items – sippy cups, suction cup bowls, mini-tupperwares that we use for leftovers, bottle brushes. These are the kinds of things that we use every day, but we are highly unlikely to have provided at an AirBnB rental.
Office Supplies Kit – Basic office supply items like scissors, stapler, tape, pens, envelopes, stamps, and yes… my label maker (I’m still a professional organizer at heart.)
Important Docs Kit – A zippered accordion file with our passports, birth certificates, medical/glasses prescriptions, check books, bills to pay, action-related paperwork, etc.
We also decided to bring a few household items that we use very frequently or really love:
  • Electric Tea Kettle
  • A few power strips & extension cords (Thanks for the reminder Becca)
  • Withings Wifi-enabled scale
  • Ceiling-projection clock (because we both love to look up when we wake in the middle of the night to see what time it is – this is a newer version of the one we have.)
  • Bose bluetooth speaker
  • Roku Box – We’ve been a streaming-only family for several years, so this was a no-brainer.
  • A few favorite reusable water bottles and travel mugs
  • Aromatherapy diffusers and some favorite custom oil blends
  • And, of course, all our computer-related gear – Brian’s extra monitor, multiple laptops, hard drives, kindles, iPad, etc.


Saturday, September 29th 

Our big Bon Voyage/Moving Sale party for our friends was scheduled as an “Open House” from 10-5pm… although I think we kept going until close to 7pm. We wanted a chance to say goodbyes to a whole bunch of different people, and we also wanted to give our friends and family first crack at taking any of our stuff home that they could use. This included shopping in our kitchen and bathroom cabinets since all that perfectly good food was just going to get thrown out in a couple days.
A steady stream of people came through pretty much all day. We told them very clearly NOT to bring any tangible gifts, and in fact we told them that ideally they would take some of our stuff with them! That worked fairly well. We were able to pass along most of Pumpkin’s nursery furniture to a co-worker of Brian’s who’s currently pregnant, and other friends took several pieces (futon, bookshelves, glider, etc) in exchange for some donations to our travel fund ;).


Sunday, September 30th

On the Friday before the sale, I went around and took a bunch of photos of our furniture, dishes, etc and posted them to FB Marketplace as part of a “Moving Sale” posted from 12-5pm on Sunday. I immediately had a TON of people contact me about specific items. Knowing the ways of Facebook marketplace by this point, I was aware that many people would “claim” things but never come to buy/pick them up. So, I made my rule that everything was “first come/first serve.” The first reasonable offer who arrived and would take the item away, could have it.
However, I will say that this is one area that I would handle differently if I had the whole thing to do over. I would have posted the items individually (rather than collectively) about a week in advance, taken deposits via Venmo or PayPal for items, and told people that everything must be picked up on the Sunday of the sale.
What happened was a lot of people weren’t willing to risk driving over since they assumed things would already be gone, so we didn’t start getting a lot of sales until midday when I started posted things individually for immediate pickup only. However, I continued to receive inquiries all night, long after we’d left for our friends’ house in Framingham.
I think I would have sold more things had they been posted for the full week and deposits taken in advance to ensure people didn’t call “dibs” but then never paid/picked up. Ah well, there’s my biggest lesson learned which can hopefully help someone else ;).


Monday, October 1st

By Monday, everything that was left was getting picked up by the wonderful team at Clean Out Your House. I’ve used them for years both for small local moves in the Boston area, but more often with our clients at Living Peace for whenever we had someone who needed a bunch of stuff to disappear. Finally that was me! They’re amazing because they will take stuff away in their truck, but they ensure that things get sorted into what can be donated vs. recycled vs. pitched. They also have a consignment shop if you have items of enough value to sell, but I handled most of that stuff in advance in our case.
I had thought it would take numerous hours to collect and load all of the random junk onto their truck that was strewn around the apartment after the moving sale… but they had the whole place cleaned out in less than 3 hours?!?
My cleaning team came through after that to give the place a quick once-over, and our Salem apartment was empty and done! Thus, the close of that chapter.


Tuesday, October 2nd

While technically this was our first day as nomads, the next two days were our transition time. We were grateful to stay with our friends Carin & Ed in Framingham.
Carin allowed me to explode all over their house as I completely unpacked, re-organized, and re-packed the car again. There were about 3-4 bags of random “oh, let’s bring that with us” crap that got tossed into the car over the weekend, which I wanted to ensure got sorted out and put with “like” items.
Two things I couldn’t have done without during this phase: ziplock bags (thanks Carin for letting me raid yours) and velcro tape (for cord control. Glory everything has cords!) I was also able to re-organize things enough that we wouldn’t have to unload the whole car again while visiting our friends in the Berkshires for our “vacation” during the subsequent 5 days.


NomadLife Vacation (1st Stop – Berkshires Region, MA- October 3-8th)

I’m SO GLAD we took this interim break before landing in our first “long-term” place in the Hudson Valley/Catskills area of New York. We both blocked it off from work commitments, and we just rested, chatted with our friends, and explored some fun places in the Berkshires. We visited Edith Wharton’s home “The Mount” in Lenox, MA.
We had a great time at the Eric Carle Museum (of Very Hunger Caterpillar fame,) which also had a visiting Paddington Bear exhibit. Both of these are favorites of mine, and we’ve been reading Paddington books to Pumpkin each night recently.
We also drove up to Williamstown, MA to see the Clark Art Institute, which has an excellent collection particularly of 18th & 19th century paintings from some of my favorites (Renoir, Degas, Rembrandt, Turner, Cassatt, Pissarro, etc.)
We are still working with a baby who’s wandering back and forth between 1-2 naps (and refuses to nap in the car *facepalm*), so our days are somewhat foreshortened to 11-3pm. But, it’s enough to enjoy lunch and a bit of exploring together.
Finally, on Monday morning (yesterday, by when this post goes live) we packed up all our gear again into our little car, and we drove the 1.5hrs to our new “home” in New York. It’s an adorable, little two bedroom house in the country that truly couldn’t be nicer! Our hosts Kathrin & Robert stopped by for a few minutes (bringing a bottle of Prosecco!) shortly after we arrived, and we thoroughly enjoyed meeting them and getting information about the neighbors and community we’ll be experiencing for the next few months.


Up Next

I will share more photos of our adventures here in NY once we have some time to settle in ;).
But, in the meantime, if you haven’t yet ensured that you’ll receive our travel updates (and all the other awesome productivity insights too,) then make sure you click the image button below to get those directly to your inbox.
Future posts might be less long-winded logistics and have more attractive photos, but I know several folks were begging me for the specifics of the downsizing process (since our decision seems to be inspiring others!!) Therefore, I wanted to make sure that I got everything written down before it started fading from my memory.