“Taking an Around-the-World Trip Bolstered My Confidence in Areas of My Life Beyond Travel”
Signing up for credit cards through partner links earns us a commission. Terms apply to the offers listed on this page. Here’s our full Advertising Policy.Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!
Miles & Points Interview: Jetsetter’s Homestead
Jennifer writes Jetsetter’s Homestead to share how she maximizes her vacation by planning extracurricular trips.
How and when did you start collecting miles and points?In 1998. I was finishing graduate school and starting to fly for work. I’d always thought I didn’t fly enough to even earn a free domestic ticket so I’d never signed-up for accounts. Finding FlyerTalk.com (still in its bulletin board infancy) changed everything.
Why did you start your blog? What’s special about it?Jetsetter’s Homestead is a 2014 reboot of a blog I originally authored from 2005 to 2009.
I’ve always written from a personal perspective about my travels and how they interweave with my personal life, whether in blog form or longer social media stories. While the world of travel blogs has exploded to encompass thousands of such sites, no one was writing about the (sometimes) deep divide between an exciting travel life and a peaceful domestic existence which is where I found myself after two decades of heavy travel.
I write about travel but I also riff on everything from making deviled eggs in the airport to Gilmore Girls and using my freezer to stretch out a pair of heels. It is basically whatever is spilling out of my head on a given day.
What’s the one single thing people can do to get more miles?Sign-up for everything – the triple miles bonus on the route you think you might never fly, an airline account in the alliance you don’t normally fly, sign-up for points in hotel program you aren’t most loyal to, register your credit cards with all the shopping portals and dining sites. Those can sometimes add up significantly over time.
What’s your most memorable travel experience?
Several years ago I took my longest-ever solo trip booked on a First Class “round the world” award with OneWorld that is sadly no longer available. Dallas to Los Angeles to Tahiti to Auckland to Sydney to Melbourne to Hong Kong to London to Dallas, across 5 different airlines!
I experienced so many firsts on that trip – being away from friends and family for the holidays, renting a car in a foreign country, and learning on-the-fly to drive on the left side of the road, staying in stranger’s homes (Homestays in New Zealand were a big thing long before Airbnb), facing the challenge of unexpectedly being forced to obtain a new passport on a holiday weekend while in Australia, and doing 3 weeks out of one suitcase.
I was at a rough patch in my life at that time – personally, professionally, and financially – so the trip took a bit of careful planning (including figuring out how to balance a very tight budget with miles & points), but I learned so much about myself on that journey. It bolstered my confidence in other areas of my life beyond travel and I bounced back in a big way in the year that followed.
Every time I think I can’t do something by myself, I circle back to that trip and remind myself what I am capable of.
What do your family and friends think of your miles & points hobby?
My family understands it – they collect miles & points too. I work in consulting, so my colleagues also understand although I may take it to extremes at times. My friends, they just shake their heads and try to make plans with me when I happen to be in town.
Is there any tool or trick which you’ve found especially useful in this hobby?Do your homework. Be sure that, at minimum, you understand the rules of the programs you are accumulating miles or points in – how to earn, how to redeem, and what benefits you may receive through the program.
Don’t expect airlines or hotels to do this for you – you may miss out on bonus opportunities or benefits that you must ask for if you do. Also find a few travel blogs or websites you like and follow those regularly.
What was the least expected way you’ve earned miles or points?
I sign-up for various dining and spending programs (like ThanksAgain) and sometimes have been shocked to see how many miles may end up posting because of a business dinner check I picked up or a purchase I made with a participating vendor I was unaware of.
What do you now know about collecting miles and points which you wish you knew when you started out?
I was late to fully embrace mileage-earning credit cards and earned my first 4 million miles in the American Airlines AAdvantage program without a single credit card dollar. I weep sometimes at the thought of all those miles that I left on the table!
What would your readers be surprised to know about you?
I’m extraordinarily domestic – it is my frequent flyer alter-ego. I bake from scratch, love projects around my house, and sometimes take my needlepoint projects with me on long trips.
If I could be anywhere in the world on any given Sunday, it would be curled up in my yoga pants in my living room with Morrissey playing while I read the paper and enjoy a lazy brunch.
Any parting words?
You can’t win at miles & points if you don’t play…so know the rules and sign up!Jennifer – Thanks for sharing your thoughts on having Big Travel with Small Money!
If you’d like to be considered for our interview series, please send me a note!
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