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My boss went on a dream six-week vacation, and these are 5 things I now consider for my future travels

There’s always something you can learn — even if it’s how your boss took his vacation — if you know where to look. Here’s what I learned.

Have you ever met someone who’s told you, “Traveling to experience different foods, sights, cultures, and people? Ew, no.” Me neither.

The point is, the majority of us looooooove to travel, but we all have different styles of how we plan for it and actually prefer to travel, based in large part on our inner math of whether certain experiences are “worth it.”

For example, I’m kind of a rugged traveler. The idea of swank five- or even four-star hotels never appealed to me. A bag of M&M peanuts for $5? No thanks, I brought my own. An $8 bottle of Fiji water? Just tap water for me.

My travel preferences are the complete opposite of IWT CEO Ramit Sethi’s (aka my boss), who recently returned from his six-week (!) honeymoon. The trip spanned across countries: Italy, Kenya, India, and Thailand. You can read all about his trip starting here.

IMG 1815 1
Real picture of a real lion that Ramit took.

For me, luxury and travel are like oil and water — like, why bother mixing them? If I traveled, I’d usually rough it out — in the occasional hostel, and for longer term stays, in affordable Airbnbs, just as I did back in my nomadic days; whereas Ramit deliberately immersed himself in absolute luxury, juxtaposed against local life, like touring the street vendors or cooking at a local woman’s house.

Maybe it was Ramit’s excitement about his experiences as he was telling it, but the idea of traveling in luxury became a contagion that latched on and proliferated in my thoughts, shifting my perspective from wanting to ask not “why?” but “why not…?”

  • Why not try splurging on lavish experiences when I’m traveling (I am older now, after all)?
  • Why not have both worlds of “ultra lux” and the humility of local living?
  • Why not be open-minded and dream BIG?

Maybe it’s meta to be cross-examining my boss’s style of vacationing with my own travels on the very blog that he founded, but it’s important to also acknowledge that just because I’m part of the team here doesn’t mean we’re a hivemind. It doesn’t mean I just “get it.” Like you, I must undergo a process of exposing myself to different and interesting ideas and letting them percolate until I choose to make them a part of my decision-making, as long as they make sense to me.

And ultimately, what I took away from his retelling of his experiences isn’t that I necessarily need to also travel lavishly or that I should go to Thailand or India or Kenya. It’s that…

1. My own dream vacation is within my reach … I just have to plan it

While I don’t care to go on my own safari adventure, I’ve been inspired to figure out how to make my own dream vacation — a multi-month stay in Tokyo for the 2020 Olympics — a reality.

My goal for the 2020 Olympics in Tokyo isn’t a spur-of-the-moment thought I came up with just now while thinking about eating sushi for dinner (¬_¬). It’s actually been on my mind since

I got to stay in Tokyo for four months back in 2016. At the time, it was a feel-good fleeting thought — something that I’d pushed off until now obviously to start thinking about manifesting.

Stephanie’s thought process then: “Future Stephanie will figure it out somehow!”

Stephanie’s thought process now: “OK, well, I am Future Stephanie now, so the first thing to do is start automatically transferring savings into an account that’s dedicated for this trip (done); find someone who can help me maximize my credit card points between now and then (in progress); then use my hella points to book first-class tickets to Tokyo.”

The main difference between thinking about Tokyo 2020 then and now is, as you can plainly see, I am aligning my actions with this goal. As of this writing, I have more than a year to go, and automatically saving for this specific goal has already liberated me from the mental strain of thinking about putting funds aside every month (we call this automating our finances).

2. I could share my travel experiences with loved ones

It’s no secret that Ramit took his parents and in-laws with him on the first leg of his honeymoon. But what really fascinated me was what Ramit said to Brian Kelly, aka “The Points Guy,” on Brian’s Talking Points podcast:

“My parents had four kids, not a lot of money. And I was just thinking that if they were to come to Rome, they would’ve come during the hot summer. They would have planned out everywhere they went based on how much it cost. And so for us to even be like ‘Don’t even think about it, just show up.’…

We took private tours of the Vatican. We took them to a cooking class. Both of the moms have never taken a cooking class in their lives. They’ve been cooking for 30-plus years! We all just hung out. And the dads bonded. It was just one of the best memories of our lives.”

I bolded the above because I understand that exact sentiment. My Asian parents would rarely go traveling, much less even *think* about spending more money than necessary on a luxury vacation. The idea simply doesn’t exist in the realm of possibilities for them.

One year I took both my parents with me to Toronto. And I remember my dad telling me how grateful he was to have been able to reconnect with his cousins after 30 years, which wouldn’t have been at all possible had I not booked his ticket and stay.

Having the perspective and ability to share these travel experiences with loved ones to me is truly the idea of abundance and generosity, as well as a powerful motivator for why I work so hard to earn money.

3. I don’t have to fall for the mindtrap of “finding a better deal”

It used to make financial sense to forego luxury hotels and experiences and restrict myself to the idea of budget travel when I was but a broke college kid. And so I’d try to calculate cost and my expected value and level of happiness or satisfaction.

More often than not, this math was way off. One year I recall passing on the opportunity to swim with dolphins in the Bahamas. Although I was interested, it was quite a bit out of my budget but still something I could afford. But I’d convinced myself that it wasn’t worth it or that I could find a better deal elsewhere.

In the end, I missed out completely, and for months that was all my friends who did partake talked about. #FOMO

Old money decisions die hard. But as I’ve learned through adopting new money habits, cost and expected outcome aren’t something I could predict or are necessarily even meant to be predetermined. It’s not always about the deal, but about the convenience and immediate opportunity of being able to indulge in something fun and unique that I otherwise would never get to experience.

4. It’s okay to spend on things I love or just want

How many of us feel a nagging guilt that we “shouldn’t” spend money on that $65 shirt when we already have 12 other shirts, even though we WANT it? It’s hard to justify, and we all feel this, even people like Brian, who travels in style for a living. Here’s a transcription of the Talking Points podcast mentioned above that I thought was particularly profound:

Brian: “I always struggle, especially in a country like Thailand, Amans are expensive wherever you go. And people will grouse, I know, whenever I say the nice hotel in Thailand, but, yeah. I mean, it’s all about the experience.”

Ramit: “I agree. I don’t think it’s for every day. I’m perfectly happy staying at a very budget airport hotel when I need to. I don’t mind it. But I do think that there are moments in life where you say, ‘I truly want to go as far as I can on this.’ And I have this concept on my site where I talk about Money Dials. Think about a dial on your car radio.

And most people have one or two Money Dials that they just love spending on. For you, it’s travel. And so you can turn that Money Dial all the way up and you can stay at Aman’s, Ritz Carlton, wherever it is that you love. Some people just couldn’t care less. But they love clothes. A lot of people love convenience. I love convenience, that’s mine. So if you know what your Money Dial is, then you can go all in and you can spend extravagantly on the things you love.”

We each have an area in our lives where we just naturally spend more money on. These Money Dials explain why we spend money the way we do. In other words, Money Dials is a way for you to figure out what’s important to you and what’s not. For example, I value relationships, so I’ve spent more money to live in a centrally located apartment, furnished from zero, to be more welcoming and host my new and old friends much more easily.

For me, the idea of Money Dials has provided me that healthy balance of knowing that I could spend money on something — guilt-free — because it’s important to me, instead of feeling like I should only be squirreling away money for an indeterminate future.

I could have both — and spend wisely and extravagantly as long as I can afford it and it makes me happy.

5. My dream vacation shouldn’t just be a dream

We often hammer home the message of “you define what a Rich Life means to you,” but I must admit that I have to constantly think about what this means for myself.  

Through writing this article, I realized that part of my Rich Life is being able to figure out that I CAN make my “dream vacation” possible for myself.

Maybe not tomorrow. Not next week or in the next six months.

But definitely in a reasonable and achievable timeline that wouldn’t get drowned out by vague “someday” hopes. I’ve already set up my savings, and it’s only a matter of time before I start looking at flights and places to stay.

The overall message here is simple: it’s important for all of us to think about why we strive to live a Rich Life. For me, it’s about being in control and deciding what my money can do and is for.

And at least for the foreseeable future, it’s living in my posh apartment to spend more time with people I care about and then taking off to Tokyo in summer 2020 to mash myself against hundreds of people from around the world to celebrate amid the biggest stage in sports ever.

See you there?

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  1. avatar

    My husband and I have been dreaming of a trip to Europe since we got married almost 15 years ago but never really had a "reason" to go. Last year we realised it was our last chance to go on a big family adventure before our daughter starts school and we're restricted to the school timetable. So we decided to just pack our bags and go for it.

    We live in New Zealand, where getting on a plane to anywhere other than Australia is incredibly expensive so the airfares alone made my head hurt. Then we had to account for the cost of doing everything with a four year old in tow, which meant we decided to pay extra (a LOT extra) to stay at hotels with a one-bedroom suite within a block of the Vatican and the Louvre so we could visit multiple times if Her Majesty got too tired and we had to leave before we were done (actually, it turned out she loved them both so it wasn't an issue, but it was still worth it being so accessible). We paid a small fortune to skip the queue at Versailles and what felt like a week's rent for every meal we ate in Switzerland.

    I'm not normally a big spender but Ramit's advice repeats in my head like a mantra "spend extravagantly on the things you care about and save on the things you don't…" and I reminded myself this is why I buy all my clothes second-hand and my husband still drives the same car he had when I met him. At the end of the day nobody really cares what I'm wearing and there are very few four year olds in New Zealand who can say they've met all the princesses at Disneyland Paris, so I figure we got the better end of the deal by far!

  2. avatar

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  3. avatar
    John Robertson, Jr.

    You are amazing! What a wonderful analysis! I spend more than I should on an annual family vacation paying for my adult children and their spouses. We have memorable trips we will remember for a lifetime. Of course their lifetime is more than mine! LOL

  4. avatar
    Wealthy Doc

    You said it.
    Money is made for spending.

    We need to take concerted action to ensure we spend it on what truly realizes our dreams, passions, and happiness. Yes, we need to pay the insurance bill and taxes, but let's not forget the good stuff!
    We doctors are guilty of this. At least the financially responsible ones are. We are used to delayed gratification, discipline, and ascetic life.

    We have to reprioritize our spending later.