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I Quit My Job to Live on a Sailboat. Here’s How I Saved $22K Before I Left
Emily Matson

You’re going to live on a sailboat?”

Yes, that’s right. This Midwesterner turned New Yorker is going to live on a sailboat for six months. With no experience sailing and little time spent sleeping on a boat, I’ve had a unique opportunity present itself and I’ve decided to jump aboard (literally) and take it.

Here’s how the plan unfolded: Two years ago, my boyfriend mentioned that his friends, Frank and Misha, a married couple, were going to sell their house, buy a sailboat and live on it while traveling the world. To my surprise, Frank mentioned that we could join them if we wanted. My initial reaction? Of course it sounded amazing, but I didn’t think much of it because it didn’t seem like reality. Stop working, live on a sailboat, spend half a year living in paradise? I wish.

But over time that throwaway conversation continued, the plans developed into actionable items, and before I knew it, we were really, seriously considering taking this incredible adventure. When Frank and Misha finally bought the boat, we were in. And over two years of saving and planning, I was able to put away more than $22,000 for my trip. (I anticipate spending less than half of it. However, it’s good to have a cushion if an emergency happens.)

To break it down for you, I had $13,000 in my savings in January of last year (2019), which is around the time I started saving for this trip in earnest. This money was accrued over more than five years from paychecks, portions of tax returns and bonuses. As for the rest? Well, that took nine strategic months of spending very little and putting away as much as I could. Yeah, it also meant putting my entire tax return and bonus directly into savings.

I want to note that a lot of pieces had to line up to make this trip possible—most important, being debt-free and having cool AF friends. As I’m sharing all of my tips on how I managed to budget to quit my job, I’m well aware this isn’t a possibility for everyone. I’m incredibly lucky and privileged to be able to embark on this journey. That said, here’s how my experience came together.

Tying up loose ends (and debt) before leaving

I’ve lived in New York City for close to five years. I don’t own a car, I pay my credit card bill in full every month and, with the help of my parents, I paid off my student loans earlier this year. My apartment lease ended a month before I planned to leave. Fortunately, my roommates were staying in the apartment and allowed me to sublet from them for a month while they looked for a new roommate. Being debt-free was the first stepping-stone to leaving my job to travel. And because Frank and Misha are rock stars, I also wouldn’t have to pay rent while living on the boat.

Planning for upcoming payments

Once on the boat, day-to-day costs are relatively inexpensive, but I’ll still have a couple of recurring payments I need to anticipate. I’m splitting a Google phone plan with my boyfriend. At $60 per month, we’ll have service in all the countries we’ll be visiting throughout the Caribbean.

Additionally, I’ve also enrolled in a traveler’s health insurance plan, so I’ll have coverage in case anything happens; this comes out to about $100 a month. I’ve canceled all streaming subscriptions ahead of my trip, except for my Spotify premium account at $10 a month, because a girl can splurge, OK?

In total, I’ll have guaranteed monthly payments of around $170.

Food and living expenses

We decided that when we set sail (woo!), we’ll split boat fees evenly among the four of us. These include things like marina docking fees, diesel, groceries and any other costs that may arise (and I’m sure they will…).

For food, we’ve stocked up on nonperishables like rice and beans, dry pasta, canned tuna, etc. While at sea, we’ll fish when we can and purchase local groceries when we stop on land. I love to try new foods in new places, so I plan to taste local cuisines from time to time, but I’ll eat on the boat when I can. For example, we’re already planning to eat breakfast on the boat before we venture to that day’s island stop and bring along sandwiches for lunch while exploring.

How I saved enough to quit my job for this adventure

As much as I’ve planned, I know that while traveling, especially for extended periods, there are always unexpected costs. I’ve always been a saver, but as this trip got closer and closer, the fear of quitting my job and having no income set me straighter: I had to start putting away more money. Here’s how I did it in both big and small ways.

1. I always offered to pay the check (yep)

We’ve all be there. The group dinner ends with someone suggesting “Should we all just split it?” Of course, this usually comes from the person who ordered too many appetizers for the table, two $16 martinis and the $35 steak. Meanwhile, I had a glass of wine, didn’t touch the appetizers and ate a salad as my main. Instead of caving, I have a new strategy: I offer to put the entire check on my card. As an anxiety-prone person, it can be nerve-racking to put a $300 charge on my card, but with the help of trustworthy friends, this has enabled me to control my spending, even in large group settings. After paying the bill, I send Venmo requests to everyone for their portion, and I get the credit card points as a bonus. It’s kind of a win-win. (However, I do not suggest this strategy if you have cagey friends who never pay you back.)

2. I resisted the urge to take a cab

Living in NYC means that cabs and public transportation are my options to get anywhere and everywhere. On long days or rainy evenings, it’s tempting to hail a cab or call a car share service. However, those rides add up a lot over time. Knowing I had to cut this cost changed how I approached timeliness. I spent a lot more time planning my routes instead of leaving it to the last minute. When the weather is warm, I’ve tried to walk or bike. I bought a used bike on Craigslist last summer, and after a few rides, it paid for itself in what I would have spent on a cab. And when I had to take a car (going to and from the airport with all my luggage, for example), I used Uber Pool or Lyft Shared. It’s not ideal after a long flight to share a car with someone, especially because it takes so much longer to get home, but it was worth saving around $30 per trip. That money goes a long way on the boat, and this could be my share in fuel, my portion of groceries for several weeks, or a really great lunch that I want to splurge on while traveling.

3. I ate out less

Instead of spending $4 or more on coffee every day, I’ve opted to drink the coffee that is supplied by my office, and this saved me close to $1,000 for a year. The same goes for Seamless. Ordering in can feel like a great option, but after tax, tip and delivery fee, a $10 burrito is now almost $20. To avoid feeling the “need” to order in, I’ve tried to keep more groceries in my apartment. By making several dinners at home, I easily saved more than $100 per week. When the craving really set in and I really needed that burrito, I opted to pick up and save on the delivery fee and tip.

While trying to be frugal and eat at home, the reality is I still live in NYC, and going out for a full dinner experience is part of the reason I’m willing to pay so much to live here. My solution was that when I did eat in restaurants, I was more conscious of what I was spending. When having dinner with my boyfriend, each of us would order one less glass of wine than usual, saving $30 on our bill. All these things add up over time, and by not spending extra I was able to save without completely sacrificing my lifestyle.

4. I used a flow chart for clothing purchases

It was tough when I wanted an item of clothing that I thought I’d get a lot of use out of, and even harder to resist when it went on sale. One oversized sweater purchase now and soon I’m obsessing over combat boots that I will definitely not wear on the boat. Next thing I know, I’ve bought three items equal to the cost of an international flight. To make better, more conscious purchases, I asked myself the following:

Is this something I’ll have for years and can wear in different seasons?
If no, don’t buy.
If yes, see next question.

Will I love this a year from now just as much as I do now?
If no, don’t buy.
If yes, see next question.

Is this something I can take with me on my trip?
If no, is this worth paying to keep in storage? (If no, don’t buy.)
If yes, is the quality good enough for lengthy wear and sun exposure? (If no, don’t buy.) 

5. I sold what I didn’t need

In preparation for my trip, I went through my belongings and thought, What can I take? What should I store? I tossed anything that didn’t meet those two requirements.

I read an article about how you can make money selling clothing online and decided to give it a try. Poshmark was the easiest for me to navigate and sell items. All I had to do was take pictures of my belongings, post with product details and set the price. 

I did an initial purge of belongings, but then I channeled my inner Marie Kondo and went through my clothing piece by piece. I thought, How much would I be willing to sell this for? Assessing the value of my belongings really put things into perspective. Is this an item that is in good shape but never fit well or was trendy two springs ago? Time to sell it.

For pieces I like that don’t make it into my rotation often, I asked, How much would I be willing to part with it for? This helped me go through my clothing and see what I really valued. The hardly worn bright green trendy sneakers that gave me blisters on my toes? Gone. The vintage Gucci bag my mom passed down to me? Priceless. On Poshmark alone, I’ve sold close to $800 worth of items, and I only started selling in April 2019.

6. Most important, I saved, saved, saved

This may seem obvious, but there is one tried-and-true way to hold on to money: Save it. I have a savings account that is separate from the checking account I use to pay my bills and expenses. Every place I’ve worked has allowed me to have multiple direct deposits. I designated an amount that I was comfortable putting aside from each paycheck and had it deposited directly into my savings. This way, I never saw it pass through my checking account and therefore didn’t miss it. I’ve done this since I moved to NYC. At my first job I didn’t have a lot to put aside, but I still put away something, and as I’ve received promotions and raises, I’ve increased the amount that comes out of each paycheck, which has led to a significant amount in savings. When I received a tax return or a bonus, I’d put most of it, if not all, into savings. Putting money, and more important, leaving money in savings is the best way to make my travel fantasies into reality.

In total, from cutting corners and selling my things, I estimate I saved around $3,500—roughly $300 a month plus the sales from clothes. On top of that, I was still putting paycheck money directly into savings (about 10 percent post-tax for the past couple years) and adding any windfalls (bonuses/tax returns), which brought me to $9,000.

Yes, there have been several sleepless nights stressing over finances. But when I think of this once-in-a-lifetime adventure, I know I’ve planned as well as possible. As my 92-year-old grandfather says every time we speak, “Travel as much as you can while you’re young, bud, because one day you won’t be able to.”

See you on dry land, folks. 

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