Why I bought a timeshare: Selling the dream of luxury travel – life on a permanent, 5-star vacation resort

This week is our last week of a month and a half tour of Mexico. Although I’ve traveled extensively since I was young, and have made money online for several years, I’m only beginning to make enough money to really travel around, work from anywhere, and fully engage in nomadic living.

During our time in Mexico we experimented with hotels, hostels, apartments, Airbnb and other short-term accommodation options. This week, however, we managed to book 5 days at an all inclusive 5 star resort for the insane price of $199 (it was a $999 package, but we didn’t pay the full amount).

Part of the deal was that we had to attend a time share presentation, and I was dreading it. I hate all forms of dishonesty and am always very transparent. So I knew that the sales rep and other staff could pretty much read in my eyes from the get-go that I had no intention of buying a time share.

Although we met all the requirements (married couples, certain age, certain income) they were hesitant about even giving us the presentation since we didn’t look like the type of people who would invest in a time share package or membership.

The whole thing was awkward: They get to know us, talk about our lives, ambitions, jobs, travel plans, and then finally offer a few pricing options. The first two packages were $59,999 and $49,999USD. I’m thinking to myself, for that much we could buy a decent house in many countries…

But then they offered us another option.

$9,999 for 20 weeks of hotel stays, with options all over the world – we would pay $199 per weekly stay. Then they gave us $2,000 off. They they gave us another $2,000 off for “giving back two weeks” (didn’t understand that part.)

So we were at $5,999 – and he threw in an extra 10 weeks.

Never would I have imagined leaving that room agreeing to pay almost $6000 dollars – a small fortune, and of course I’m still anxious about it. But here’s why I signed.

My wife and I plan to spend most of the next year traveling around the world. Obviously the best bet for us is to find a nice apartment on AirBnB and get a good monthly rate (between $500 to $1000). But, as we experienced in Mexico, sometimes you want to go visit another city without living there, or need a place to crash for a night.

I spent way too much time on agoda.com looking for hotels that were often about $80; nicer apartments on Airbnb are usually over $75 – which works about to about $525 a week (over $2000 a month.) Not ideal, of course, but if you’re traveling and don’t have much choice, you take what you can get.

I’ve always been a budget traveler at heart; I used to love not knowing where I’d be sleeping, meeting new people in hostels, being free to explore. But since a single room for two at a hostel is upwards of $40, it usually makes more sense to spend a tiny bit more for a hotel room, especially since I’ve got a pretty decent graphic design/computer set up that I travel with. I need a desk, an office, somewhere comfortable, to get work done as we travel (that’s really the whole point – being able to support yourself on the road).

And as much as I hate wasting between $50 and $100 on 1 night – it’s even worse to pay that much for a mediocre room and very few amenities. Sure, we could travel through Europe on a shoestring, stay in cheap and boring apartments and dingy hotels – but that’s entirely not the point of the lifestyle I’m trying to create.

I learned in Mexico, after taking the first apartment we found (roomy, but extremely boring, far from the city, no internet) that since 80% of our time abroad is probably going to be spent in our room, choosing a place to stay is not to be taken lightly.

Sure, we can say “It’s only for 1 night” or “it’s only for a month” – but that’s a huge chunk of our life spent in surroundings we don’t love.

Of course “normal” people will find a place to life and buy a house, paying several thousand a month on a mortgage. I understand this is a very practical and smart plan – I can’t say I don’t hope to be able to buy a house also someday.

But the lifestyle I’m developing has different aims: the goal as self-employed/creatively independent is to constantly increase the amount of products/businesses/money generating assets that are bringing income to you. While many people save for retirement – a time when they can stop earning money and live on their savings – I’m planning on developing my resources to the point that the income never has to stop.

But in the meantime, I can’t recommend this lifestyle to anyone unless it is comparable with the comfort and pleasure of home-owning: that is, having a truly wonderful, awe-inspiring, creativity generating place to stay. Being fully self-employed or creatively independent shouldn’t have to be a sacrifice from the kind of lifestyle regular people with good jobs can earn.

Paying $6000 now on the possibility of future hotel savings appeals to me for a few reasons:

1) I can spend less time worrying about where to stay because I’ve already paid – I’ve prepaid – for some great hotels around the world.

2) Rather than feeling guilty about “splurging” in the future on a good hotel or feeling “cheated” by paying for a bad one, this one time payment will nullify a lot of future hotel-booking anxiety, allowing me to enjoy our travels, spend more time working.

3) Most months we hope to find an apartment for around $500, but will splurge sometimes for a week at AirBnB’s truly amazing options. But now, at the same time, we also have the option of staying for a week (or four) at a luxury resort for $199 a week – less than $800 a month. Although we’ve already paid for it (the actual price is closer to $500 a week) having that option on the table, when normal booking at the same hotels would be in the $200/$300 range per night, seems to be a handy bit of travel ability.

But that’s if it all works out.

The truth is, I was sold a dream of luxury travel. I was sold the potential of future realizability.

It reminds me of several popular books, that offer inspiration to create you own life, make your own money, travel and do whatever you want – offering you the idealized image of a luxury lifestyle without supplying the hands-on personal steps to get you there. When you buy the book, you buy into the affirmation “Yes, I can do this too!” whether or not you actually follow the guide of the book to develop your own path to success is beyond the point.

Likewise, I don’t expect my time share experience to be easy or cheap. I don’t think I’ll save a ton of money. I may even have spent too much. But, I will do my darndest to use the weeks I’ve bought and exchange them for the best, highest class resorts throughout Europe and Asia – places I never would have dreamed of staying just a few days ago. Buying the Time Share changed my reality by raising my expectations, both in terms of what I think I can afford, and what I expect others to provide for me through my membership.

This is a powerful – almost magical – part of manifesting your ideal lifestyle that is rarely talked about: sometimes you have to take a big leap from the small bowl you’ve grown accustomed too, and hope you make it into the big bowl. You might be terrified at first. You might even miss the big bowl and end up on the floor gasping for breath, contemplating death before circumstances allow you (hopefully) to get back safely to your small bowl. But even if you fail, you’ve learned more, you’ve grown tougher and more aware. After since you’ve seen what’s out there, you’ll probably jump again – and next time, you’ll probably make it.

I don’t want Creativindie to only be about supporting yourself through art and writing, because – while it’s a great goal – it’s insignificant. Who cares if you can support yourself or your loved ones? Who cares if you can quit your job and go on permanent vacation. Sure it’s a good start, but ultimately it’s very selfish and small-minded. At first I feared the same about me buying a Time-Share (how can I preach “luminosity” – leveraging your creativity to make a positive impact on the world – while spending so much money on something as trivial and selfish as luxury resort living?)

But here are my responses (both to myself, and to you by extension):

1) There are many bloggers right now urging you to quit your job and start a new life overseas with  your mobile business. But most of them are minimalists: they teach (truthfully) that it doesn’t take that much to live abroad pretty comfortably. I’ve been doing that for years, and living in very decent apartments – but nothing about my lifestyle was really inspiring. It certainly wasn’t enough to spark that powerful, consuming enthusiasm (something like a blend of envy and lust). But living for 28 weeks (7 months) in luxury resorts across Europe, the Middle East and Asia? Pretty damn cool. I hope it will allow both myself and others to broaden their awareness of what’s possible, what’s achievable.

2) The early retirement: We will be surrounded at these resorts by business owners, most of them who have plenty of money and are living a completely different reality from us. Unlike us, they built up their businesses/savings first. They probably have a house and a couple cars somewhere and travel a few weeks per year. But when they were our age they were probably working 9-5 jobs.  In contrast, we are enjoying our “retirement” now, and investing our time into the creation of passive income generating products (books, art, etc) that will grow in time. I realize our path is riskier, but it also holds more promise: successfully achieved, we are (like them) spending our youth working, but without the burden of house or car payments, allowing us to invest more into our own projects, while living the lifestyle that they had to save up for decades. Simply living this lifestyle wraps us in a protective cloak of perceived success (both externally and internally) which will change our own perception of our abilities, as well as others’ perception of us.

3) Effectively, we have moved up a rung on life’s ladder: from this vantage point, it is easier for us to view and understand commercial opportunity and business prospects; it is easier to develop confidence in our own abilities to make money; it is easier to convince others that our lifestyle has some value and we are not just kids escaping responsibility by hiding out in hostels. This makes it easier for us to forge powerful relationships with influential people and generate more cash, faster – generating a crescendo of creative energy that can be deployed towards whatever benevolent or altruistic cause we feel called towards.

At least those are some of the things I’m telling myself to justify a position I never pictured myself in. At heart, I’m anti-tourism and would prefer the experiential lessons of a homestay, or living in a student dorm  surrounded by locals. On the other hand, picture the scene between Mat Damon and Ben Afleck in Good Will Hunting: Damon, despite his potential and unlimited opportunities, is waxing poetic about the beauty of simple hard work. Afleck tells him that actually, staying there by choice when he could be doing something else is an insult to all of those people who can’t make the same choice and are forced into their position.

Isn’t this the same situation we face as international travelers? We can attempt to live simply, like the locals, giving up our Western birthright of affluence and success, but we will never ‘fit in’ because  we have  a choice that they were never given: We can always escape and go do something else. Why pretend we don’t have this ability – this responsibility? Isn’t it kinder to them to leverage our ability for a huge income, and present them with lavish tips and generosity?  (obviously a controversial subject, one I’m not settled on, merely voicing opinions.)

In contrast, budget travelers and eco-tourist try to visit other countries without leaving anything behind, without spending a lot of money or making any impact. How is this better than huge resorts full of rich tourists, that are actually stimulating the economy? (Even though the resorts are probably owned by Americans anyway, at least there are a lot of jobs to fill…)

I’m not sure I’m sold on either method of travel. But the spacious lounges, the open bar, the comfortable furniture and all the other luxury perks of resort travel sure do make for an enjoyable “work from home” experience.

 What’s your favorite way to travel? Do you have any experience with Time-Shares?

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Derek Murphy

I’m a philosophy dropout with a PhD in Literature. I covet a cabin full of cats, where I can write fantasy novels to pay for my cake addiction. Sometimes I live in castles.