A Boat To Bangkok: Where Do I Start?

JANUARY 8, 2026

It was a summer day in 2015 when the tall ship The Hermione sailed into New York Harbor.

Her crew sailed into the bar where my friend Tommy and I were hanging out and we all became friends. Which is how we found out that these sailors? They were amateurs. Anyone could apply to sail that ship.  

So being the adventurous sort, I took out my phone and applied on the spot. I also signed up for a few other sailing websites.  And then immediately forgot that I’d done any of these things.

For 2 years.

And then one day I got an email from a man who asked if I wouldn’t mind coming to Koh Samui to sail his catamaran through the Gulf of Thailand to Bangkok.  

Uhm…you want me to do what now?

Seems he’d bought the boat a few months earlier so that he and his girlfriend could sail over all the seas. Which they’d been doing until they got to Kuala Lumpur where the girlfriend decided she was done. With the boat. And the boyfriend. 

And so now he had a new plan, which was to high-tail it to Thailand, ditch the boat, and go do whatever you do in Bangkok when you get dumped by the love of your life.

The problem with his plan is that it would require him to stay awake for about 5 days straight and he figured he was probably only good for 2 or 3. He was desperate for help. And now he was emailing me.  

Me, a woman with no actual sailing experience.

This poor guy wanted to fly me in and then he was gonna basically sleep as much as he could, while I sailed his boat all by myself through the deep waters in the Gulf of Thailand.

I was like, OK but you know I don’t actually know how to sail your boat.  

He was like, You don’t have to know how to sail the boat. It’ll be fine. 

And I was like, Okaaaaay....

He was right. It was fine.

For 3 days, I sailed this guy’s boat through the Gulf of Thailand. 

And the wild thing is? I truly didn’t need to know how to sail. I just needed to know how to steer.

Because once he got the boat going? All I had to do was keep it going.

A boat in motion, stays in motion.  


The trick of course is to get the boat in motion in the first place.  

Sir Isaac “Boat in Motion” Newton calls that “getting it started.”

And this is the problem with that: Starting sounds easy. But starting is not easy at all. It’s scary. And overwhelming. And requires all kinds of forces, most of which (in my personal experience) come in the form of bribery by candy.

It’s a wonder I still have any teeth in my head.


It takes a tremendous amount of gumption to square your shoulders and stare down The Big Ugly Thing that is stealing all of your peaceful easy feelings and say to it: No. More.

And really mean it this time.

Especially when The Big Ugly Thing is a whole bunch of things cluttering up your home and making it hard to live there.

Because starting to declutter. Is. Hard.  

And there are all kinds of feelings attached, most of which involve confusion about where to start and fear that we’ll stinky fart it up somehow. 

Or get in over our heads. 

Or won’t be able to do it and we’ll give up and turn back and will have wasted all of this time and energy just to be back where we came from.


All of those thoughts are real. And not just about decluttering.

Anyone who has ever done anything has thought them.

And also? Anyone who has ever done anything has decided that they are going to have all of those questions and fears AND they are going to do The Big Ugly Thing anyways.

They start. And then they do. And so will you.


You can be uncertain about what to do first and do The Thing anyways.

You can be terrified that you’re gonna end up biting off more than you can chew and do The Thing anyways.

You can be worried that you’re gonna wind up pulling everything out and then shoving it all back and do The Thing anyways.

Because you are a do-er. You do. And doing this is important.

Having a home that makes your life easy and lets you rest and is full of heart and happiness and all the members of your book club every Tuesday night is important.

And you need space for that to happen. The live you want to be living needs space. And shouldn’t have to do battle with the Christmas decorations and the toilet paper and stacks of old textbooks and magazines just to get the yoga mat out of the closet and onto the floor.

So.  

If you haven’t already started, this is your sign to put the boat in motion. So it can say in motion. 


So let’s get practical. Where do you start?

✅ Pick a room if:

  • you need visible relief and you need it fast.   
  • there is one room in your home that you avoid because you just can’t.  
  • you have all kinds of stuff everywhere and most of it doesn’t belong where it’s sitting right now.
  • you want one space to feel better.

✅ Which room? A good starter room checks at least two of these boxes:

  • It is really stressing you out and finishing it will make you exhale.
  • You are living in it every day and sorting it out means you’ll feel the win every day.
  • You rarely use this room and so working on it isn’t going to disrupt your entire week when it gets messier before it gets awesome.
  • The clutter in this room is slowing you down and you just need it to not.
  • It contains lots of items that don’t belong there. And getting them out of the way will make the whole space feel lighter and liveable.


✅ Pick a category of items if:

  • you keep finding the same items all over the house,  
  • but you can never find anything when you need it.
  • having all of your cords or paper or kitchen gadgets sorted out and handled will give you peace.
  • there is one thing that would make tomorrow so much easier if it were under control.
  • “One thing totally done” feels better than “one room slightly better.”


✅ Which category? A good starter category checks at least two of these:

  • It’s small enough to finish (or at least finish a subcategory of the category) in one session.
  • You are fighting with these kinds of items on the daily. Or you’re always searching for these kinds of items. 
  • It is full of duplicates and things spread and migrate all over the house and you just want them to have one home where they belong.
  • It is haunting you. You can’t stop thinking about it. And not in a “I think about it and smile” kind of way.
  • Includes lots of things that will have quick, easy decisions. Things are expired or broken or duplicates, etc.


✅ Want a quick and fun way to pinpoint exactly the right place for you to begin? Scroll to the PPS and download my free Downsizing Starter Kit. 

A quick Cosmo-style quiz that will tell you exactly what room or category will bring you the most relief right now. And it’ll give you your first steps to get your first win. 

This is how you get the boat in motion. So you can sail that dang thing all the way to Bangkok.



Your friend who wonders if she can put sailboat Captain on her resumê,
Vivian




PS. What’s the Big Ugly Thing you want to start? And what's been keeping you from starting it? Hit reply and let me know. I will read it. And I will reply back.


PPS. Not knowing where or how to start is a real thing. And I do NOT want that to be the thing that keeps your downsizing project in “objects at rest will stay at rest” mode.  

That’s why I created The Downsizing Starter Kit. It’s a free, 10-minute tool to help you get out of decision paralysis and into motion.

You’ll get:

 ✅ A quick quiz to reveal your personal starting point, based on what’s stressing you out most.

 ✅ The one micro-zone to start with (and permission to ignore everything else)

 ✅ A simple Exit Strategy to get things out of your house, not just rearranged


Send Me The Kit!
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Why it brings us joy.  And what to do if it doesn’t.

Let’s talk about the things that make our lives better and how to deal with anything that’s keeping us from experiencing the pleasure of just being at home.

Because don’t we all want more style, ease, and FUN in the part of our life that isn’t taking place at work?

Yeah. I think we do.

On smushed angels, invisible love, and why your home feels crowded.

December 5, 2025