As you know, I love to think about different “retirement” lifestyles. Over the years, I’ve pondered many different cool lifestyles. I’ve thought about buying a sail boat and spending months floating between the Caribbean Islands. I’ve also thought about renting an RV and rolling through North America chasing the best seasons in every state. 

And I’ve even considered Mama Lee’s incredible lifestyle – she lives permanently on a luxury cruise! Really, Google her. She’s awesome. 

I recently heard about an article in the Wall Street Journal highlighting the idea of working remotely in a different exotic city each month. I don’t have a subscription to the WSJ, so I couldn’t read the full article. However, the idea of spending each month in a new city sounds kind of amazing, doesn’t it? 

You wouldn’t need to learn to sail unless you wanted to, and you wouldn’t have to try and drive a large RV through rush-hour traffic. Depending on where you go, you might not even need a car. 🙂 

Here’s the question to consider… 

If you could live (and work) remotely in a new location every month, where would you go and what would you do? 

I’ve been kicking this question around and sketched out the following rough plan: 

January – Basking in the sun and beauty of the Turks & Caicos Islands sounds pretty good to me! We’ve never been to Turks & Caicos, but I have to think exploring the islands for the first month of the year would be incredible. Especially considering the weather in Ohio during January! I would get up early and work for a few hours, so I could scuba dive and snorkel in the afternoons. Once we wrapped up our afternoon excursions, we could enjoy incredible sunset dinners and long walks on the beach with a bottle of cheap wine! 

February – How about hopping over to Maui, Hawaii? We went to Maui for our honeymoon, and it was simply paradise. It would be amazing to live on the island through February, which just happens to be my least favorite month of the year. This month would include snorkeling, zip-lining, and a sunrise bike tour of Haleakaka National Park. In addition to the sunsets, we’d have to go to a one or two Hawaiian luaus, too.

March – The Florida Keys sound kind of nice for the month of March, don’t they? From my research, it seems as if March may be the sweet spot for the Keys. It’s between the busy winter and summer seasons, so it’s not very crowded, and the lodging rates are very reasonable. The weather is also still amazing, averaging in the 70 degrees. We’ve vacationed on Islamorada previously and loved the relaxed pace of life. The drive down to Key West is simply amazing. Add in some scuba diving, snorkeling and some great food and it sounds like an amazing month! Move over Hemingway, the Mintons are headed your way. 

April – We’ve vacationed on Hilton Head, South Carolina, every April for the last 13 years and love it. It’s not too hot, and the island isn’t overly crowded yet. Why mess with a good thing? This month would also include-mini trips to Charleston, South Carolina, and Savannah, Georgia! 

May – This was a hard one, but I ended up picking Memphis, Tennessee. It’s the best weather for the area, and it’s also “Memphis in May,” featuring the National BBQ Championships and many music festivals. Good weather, great music and BBQ, what could be better? Sign me up! 

June – We’ve never been to Cape Cod, and the month of June just seems like a great time to visit. How about some time on Nantucket? Or a mini-trip to tour the Gold Coast Mansions? 

July – At first I was going to pick Manhattan, New York, until I realized I wouldn’t want to spend an entire month in the Big Apple, since we’ve been there several times. A long weekend would be perfect, especially to enjoy the 4th of July fireworks. I ended selecting Montreal, Canada, instead. I realize this is the main tourist time for Montreal, but it just seems to fit perfectly. It’s a major city we’ve never been to, and it sounds like an amazing place. While there we would be in “tourist” mode, trying to see Mount Royal, St-Paul Street, and Basilique Notre-Dame and the views from Au Sommet.

August – On the way back from Montreal, why not stop and spend a month in Mackinac Island, Michigan? Per Business, “Visitors can enjoy the sunny weather while boating, fishing, and parasailing. On land, you can hop between historic sites. And sweet tooths will have something to celebrate too: the Mackinac Island Fudge Festival!” I just happen to have a sweet tooth. LOL.

September – Based on my research, the busy tourist time for Amsterdam, Holland, is between May and August. September may be more enjoyable because it will be less crowded. Plus, the weather will still be decent, with averages in the 60 degrees. So off to Amsterdam we go! Take a second and Google fun things to do in Amsterdam, and you’ll be blown away. 

October – How could you not pick Asheville, North Carolina, for the fall? Picture the leaves changing colors in beautiful 65 degree sunshine! I don’t even need to mention the stunning views from the Biltmore. This month could include mini-trips to Nashville, Tennessee and Charlotte, North Carolina. 

November – According to Mr. Google, the weather in Malibu, California, for November is an average of 74 degrees with only three days of rain. Sounds amazing, doesn’t it? This is where I’d spend the second-to-last month of the year. On a quiet beach enjoying the quiet life. 

December – After enjoying such an amazing year, I would want to come home to be with my family for December. Think Christmas trees, Christmas lights and decorations, Christmas cookies, Christmas presents and fun family days in front of the fireplace. This would obviously include watching old family videos, too. The day trips would be to visit our extended family in PA. 

I have to admit that it was a lot of fun to think about where to go each month. My suggestion (and your homework assignment) is for you to do something similar. This little exercise is extremely valuable for you, as you really think about creating your future. 

Your plan is sure to be signficantly different than my plan, and that’s fine. Maybe you’d travel more internationally, visiting Sydney, London, Paris, Rio and Buenos Aires. 

Or maybe you’d decide to go from one warm island to another. 

My hope is that you really think about this! Maybe even go out to dinner with your significant other and create a plan together. It’s a lot of fun to dream about. 

Now that you’ve finished planning this amazing year, try and get an estimate of what it might cost to actually do. Research Airbnb and VRBO properties. See what the transportation costs will be. Will you need to rent a car? How much will you spend on food and entertainment? See if you can get an estimate of what it might cost per month. Would it be $3,000, $5,000 or $10,000? 

Remember, life will give us what we ask of it. 

The problem is we don’t typically ask for much. This plan allows you to ask, and to plan for, an amazing year. 

Now, you can probably guess what the next step is, right? 

Start thinking about how you might create the monthly cashflow you’ll need to fund your plan. Could you create the needed cashflow from investing in income-producing assets? Or would you start a new cashflow business that you could run remotely? 

Why not set a goal to create this monthly cashflow in 2020? New year = more monthly cashflow!

I’ll even help you do it. 

Just become a Cashflownaire Member here.

Yes, I’ve just opened the doors to my Membership! It has been closed to new members for a few months. Even better, I’ve added an incredible bonus that I’ve never included for new members before.

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