My Plan to Live in 43 Cities and Make Money Doing It
June 16, 2017This spring has been an absolute blur for me: my daughter graduated from college, then six days later, my middle guy graduated from high school. Two days after that, my youngest started taking finals in his first year of high school. Granted, all I had to do was show up & root them on, but it’s been super busy and a bit emotional too.
Any day now, my daughter will receive a job offer and become a full-fledged adult member of society, when I swear it was only a few days ago that I held her hand and walked her down the hallway to Ms. Linzey’s kindergarten class… Now I’m facing the fact that in three short years, my youngest will be a high school graduate, moving on to the next phase of his life. It’s time for me to ponder what I want to do once the kids are gone.
The last two decades of my life have been way more about them than it has been about me, and for that, I’m a much better and happier person. But now that it’s time to start thinking about my next chapter, I realize that what I have jokingly referred to as my “Professional Hobo Plan” (PHP) is actually something I might be able to pull off.
Becoming homeless by choice
One of the beautiful parts of working at Financial Finesse is that in order to do my job, all I really need is a telephone, a solid internet connection and a nearby airport. From what I’m told, they have those three things pretty much everywhere now, which means that I can work from almost anywhere. So that’s what I plan to do.
My current game plan for my PHP is to move around to a number of different cities for some yet to be defined period of time, long enough for me to feel more like a local than a tourist. Right now my list of places sits at 43, but it grows once in a while. Some places, like New York City, might require a 3 – 6 month stay (or longer) in order to learn the city like a local, while some, like Portland, Maine, might be more like a 2 – 3 week engagement. In between cities, I’ll come back home to Baltimore to see friends and family – and anyone is welcomed to come visit me during my travels.
Living in 43 cities without going broke
This sounds like a cool plan in theory, but the question I’ve wrestled with was how to pull it off without going broke. I already went through a long and costly divorce and am not where I projected I’d be financially at this age, so I need to make up ground rather than lose ground toward my longer term goals. This is when a few conversations over beverages, random thoughts in the shower, time alone on a plane/train/automobile and some time playing on the internet gave me some ideas about how to fund this and even make it a positive impact financially.
Making it a financial win
While going through my divorce, I actually lived on a boat for 3 – 4 years before moving back on to land and selling the boat. I moved primarily because my kids didn’t love winters on the boat, but once they’re gone, I can easily buy an inexpensive boat, which are in great supply with low demand in this economy, and spend my Bmore time on the boat. This would give me a place to stay while I rent my house for a 2 – 3 year window.
I’ll have my Financial Finesse paycheck along with rental income, while my living expenses will consist of a cheap rickety boat & slip fees that are less than my property taxes. I figure I can save my entire income for a few years if my rental income is steady. And as an added bonus – in some cities there are opportunities to get paid to do house-sitting! Who knew??? I’m picturing a house-sitting income in one city that might pay for a non-house-sitting temporary home in my next city, so my effective cost of on-the-road housing is negligible, while my Bmore housing cost is a net positive cash flow. And, I get to see every cool city in the US and learn them like a local. I may even get a book written along the way…
Making the most of a flexible job
That’s the dream, the plan, the working model currently. I’m not sure if I’ll pull the trigger on this plan in 3 years or not. Life has a way of throwing things at us that make plans change. But if I do, it’s completely because this work-at-home when not traveling out to client sites allows me a lot of flexibility and freedom. And — if I can get the US plan worked out – I could potentially expand the model to include some international cities. That might take more coordination because I do work at our client sites fairly often, but I have a few dozen US cities to hit before I start putting my International Hobo Plan (would I get sued if I call it my IHoP idea?) into action.
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