Using Points and Miles to Travel Impulsively and Why You Should Never Sacrifice Your Love for Travel

Hello from Tokyo! A couple of days ago I booked a trip to Tokyo on a whim, and those who have been following the blog for some time now probably have noticed a recurring pattern in my travel style: I usually just get up and go when the right doors open, without second-guessing myself (remember my New Year’s Resolution?).

Over the past couple of months, many friends, family, and readers have reached out to me via Twitter, Facebook, and email, asking me some degree of the same question – “How Do You Do It?”

To be honest, I do it because it’s really not that hard to. So many people forget how simple it is to just live the life you want to live. Not to be all Oprah on you with a leadership talk, but just remember that everyone is the pilot (how fitting) of their own circumstances, and that’s a beautiful power to be proud of.

In fact, I recently read a super inspiring post written by Dia, The Deal Mommy, titled There Will Never Be Another 22 (or 32, or 42), and it gave me chills because she basically took the words out of my mouth. In a lump-sum, Dia challenges people to really go after what they want instead of putting it off with an excuse or some internal fear of the unknown. If you haven’t read it yet, I encourage you to do so.

Granted the fact that I’m grateful to generally have the time to pick up and go as I please because I’m self-employed/a freelancer, there’s also some down-sides to that way of life too. Working for yourself means that you don’t have “steady” income, and believe me, the unpredictable earnings can dip and rise at extreme levels. On a personal note, in this past year alone, I’ve experienced both the “rock bottom” and the “thank-you, universe” phases. So what? I survived. I always know tough times get better. And to honest, the whole not-knowing-what-tomorrow-brings phenomenon is exciting to me; I see it as a positive challenge, encouraging me to chase my dreams harder.

I also have learned not to feel sorry for myself and not to have a pity party when work is slow, so you’ll never see me sacrificing my love for travel. Just like eating well, taking care of my health, or even investing in a higher education, I believe that travel enhances my overall well-being and is a vital source of continuous learning. I initially became heavily involved in the game of points and miles entirely because I saw them as the fuel for my burning-desire to travel, especially when it was not financially possible for me to do so.

One of the things I love about points and miles in general is the great sense of freedom that comes along with knowing that I can feasibly get almost anywhere comfortably with very little notice in most cases without breaking the bank. Sure, there are unavoidables like fuel surcharges, taxes, visas, spending money, etc., but if you play your cards right you can basically toss out your “I-can’t-travel-because-of-X” excuses out the window. Truthfully, if I had only one message to spread over the course of my lifetime, it would simply be these four words: Get Out and Travel.

So when people ask me “how I do it”, this is how I answer:

• Be Inspired: The first step is the find the seed of inspiration within. Nobody can motivate you to do the things you want to do better than yourself. I always hear people saying things along the lines of “I wish I could just wake up, go to the airport ticket counter without a plan, and just hop on the next random flight going anywhere” (kudos to my friend who did that for her honeymoon) and “Ugh, my week was so stressful, I wish I could just wake up in Paris.” Those are examples of some common travel wishes that get tossed around in conversations left and right. Whether it’s travel-related or not, the same principle applies to everything in life: envision what you desire and go after it. Speaking of inspiration, remember my rant about how some people just don’t get it? Not everyone will always be on the same page as you in life, but that’s OK.
• Leave Your Fears at the Door: Remember your first flight? Your first big trip or first time in a big, foreign city? Heck, even go as far back (…or as recent as) your first kiss. I bet you can relate that on top of all the excitement, there was an icing of fear, but when it was all over, you said to yourself, “hey, that wasn’t so bad”, or “looking back, I can’t believe I was so fearful at that moment!”. In a strange way, fear is a good thing; it keeps us on our toes and gives us a shot of adrenaline, allowing us to get through it. Sure the thought of traveling impulsively can and will be fearful in come cases, but so what? I recently met a woman who told me that after going through a bad divorce, she decided to pick up the pieces and go all the way to Turkey to clear her head in a Turkish Bath House. For many years she has always wanted to do that, but she had never been on an airplane before and had a tremendous fear of flying. Long story short, she ended up meeting a new man there (yes, in the bath house), and now they’ve been happily married for decades… and they both have earned top-tier status from flying together all of the time.
• Just Book It: Don’t think so much! Turn off your analytical brain and let your heart and gut take control. When there’s a flash sale/mistake fare/unbelievable mileage-run opportunity, my philosophy is “book now, think later” because most airlines/booking agents have a 24-hour free cancellation policy anyway (just be sure to check), so there’s really nothing to lose. I’ve had several successes in this year alone just “booking it”, such as my $1 room at the Public in Chicago, a round-trip flight from NYC to TLV for $330, my $14 round trip flight to Boston, and an amazing award redemption for a first-class suite on Singapore Airlines with United miles.
• Diversify: Aside from my 14 or so travel credit cards, in my family alone, we have over 130 active frequent flyer accounts and loyalty programs spread across 5 people. I keep track of all of my balances with Award Wallet. Some accounts have as little as 100 points, others over 100K, but they have all been useful to me when traveling impulsively. It’s important to remember not to put all of your eggs in one basket with points and miles. Having variety allows you to have more routing options, hotel choices, and possibilities.
• Status Helps: Having elite status is definitely helpful when it comes to taking a spontaneous trip, especially with airlines. Many airlines charge a close-in ticketing fee (roughly $100 per booking) when making an award redemption for travel booked with less than 21 days notice to non-elites. Having elite status grants you a reduced close-in fee or eliminates it all together if you’re top-tier. For those who are non-elite or a measly Silver like me, there are ways around the close-in fee if you have a trusted top-tier elite friend and a credit card with a flexible points system like, the Chase Sapphire Preferred^SM Card. Scottrick (Hack My Trip) recently was kind enough to book a last-minute ticket for me using his miles from his United 1K account, avoiding the close-in fee all together, and I was able to immediately “pay him back” by transferring my Chase Ultimate Rewards points right into his Mileage Plus account (related post). Another good thing about status is having lounge access, which allows you to save money on food and drinks at the airport so that you to have more money to do fun things in your new destination!
  
• Know Your Programs: For those who are new to the game, I’ll agree that diving right in and getting to know all of the program rules can be intimating at first, but if you can get familiar with your programs, then you’ll have a better sense of which miles and hotel points to use to get the “most bang for your buck”. As an example, for my impulsive cruise last month, I knew right away that I could get to Miami via American Airlines for  just $5 round trip using 15,000 British Airways Avios. That same trip would have priced out as 25K AAdvantage miles had I booked it directly from my American Airlines account (bad redemption, IMO). Do your research and you can stretch your points and miles to their limits.
• Stay Current: This one’s a no-brainer. By staying current I mean keeping up with the blogs (high five for reading this one), forums, and social media. To be honest, 90% of my yearly travel is inspired by some type of “deal”. I generally have a sense of where I want to go in the world, but if I see an awesome mileage run deal posted on one of the forums like MilePoint and FlyerTalk, I jump on it and make a vacation out of it (looks like I’ll be doing some zip-lining in December – last week I booked a $284 round trip flight to Costa Rica). It’s also not a bad idea to follow your favorite airlines, hotel brands, and personalities (ahem, are we connected?) on Twitter and Facebook because that’s usually the primary source of the latest deals, promotions, and ways to get free points.
• Be Realistic: Most importantly, be realistic. For instance, just because you have a stash of points and miles does not mean you get to wake up and hop on your own personal private jet. Also, re-evaluate how you’re earning points and what points are important to you. So many people come to me and say, “I have this great credit card that gets me so many points” and I nearly cringe when I hear that it’s a co-branded Costco card. If you’re serious about traveling on moments ‘notice, do your homework beforehand  and set realistic goals. It’s also imperative to make sure that traveling impulsively is right for you. If it doesn’t feel right, doesn’t fit in your schedule, or if will leave a tremendous dent in your wallet, I wouldn’t recommend doing it. The whole point is that you feel good before, during, and after your trip.
• Let Go and Have Fun: As a conclusion to a rather-long post, I’ll leave you with just few words: Enjoy every minute of your journey. Let go. Disconnect. Breathe, and take it all in. Open your mind to learning.

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