Travel hacking and other shortcuts

“We have to leave now and you don’t even have your shoes on!” said my Mom many times in my youth.

“No problem” I said. “I’ll put them on in the car”.

Ever since I can remember, I always had a burning desire to be efficient with my time. If there was ever extra time, I wanted to spend it doing everything but work. When I was a kid, it was watching TV, playing Atari (2600!), reading about sports, re-organizing my tape collection, or just staring off into space. I didn’t like cleaning, picking up stuff, washing dishes, or having to put my shoes on before heading out for school.

I still don’t like any of those things, especially having to wear shoes ever!

Shortcuts, in my experience, are underrated. I love shortcuts. They enhance my life! Some of the more practical shortcuts I take are:

-Now that I don’t have a dishwasher, I batch my dish washing. If I have to stop and clean my dishes after each meal I eat at home, it’s much less enjoyable and takes more time than if I reserve a little time each day to do all the dishes. I don’t mind cleaning dishes if it’s all at once. I turn on a podcast and it’s almost meditative! But having to do dishes with every meal is super annoying and a small time suck.

-I do my laundry every 2 weeks. Another instance of batching work. I hate laundry, it’s one of my least favorite things in life next to dishes. But, if I don’t have to do it all that often, I can save time and effort by doing two big loads every other week instead of constantly heading to the laundramat. I’m still planning on getting my laundry lady back to pick up, wash, fold, and bring back in 24 hours- a much better shortcut!

-I wear flip flops whenever possible. No socks involved, no tying anything, just step in and go.

-I go through the automated car wash. Takes about 4 minutes. Much better than scrounging for quarters and spending an hour or more at a self service car wash, and really not saving any money.

-I listen to my podcasts and audiobooks on a faster speed (1.5x or 2x), and use a piece of software called Enounce Myspeed that allows me to watch online videos at a faster speed (up to 3x, but I’m usually around 1.5x).

As for travel hacking, it’s a work in progress. But I’m learning things and getting better. Earning airline miles is the best way to save on travel. For a while now, I’ve put all my business expenses and most of my personal expenses (minus stuff like rent and mortgages) on United Mileage Plus credit cards. That has worked out well and got me 2 free trips to Asia, including one business class flight.

However, I’ve barely scratched the surface with miles.

I read Chris Guillebeau’s post on travel hacking 6 weeks ago and set out to implement the system.  This is a quick summary of how it works:

-Apply for and obtain one of the Chase Ink cards that allows you to earn 5x miles at office supply stores (among other things)
-Apply for and obtain an American Express Bluebird debit card
-Go to Office Depot and pick up a few Vanilla Reload cards. You can add up to $500 each to these and they cost $3.50. Use your Chase Ink card to get the 5x points.

Then, you simply transfer the funds from your Vanilla cards to your Amex Bluebird, and from there you can pay anything with it- including rent, mortgage, and all your bills.

Genius, right? I thought so. But there’s a glitch. Office Depot no longer carries the Vanilla Reload cards. I’m trying to figure out now if this can still be done somehow. In the mean time, by using my new Chase Ink, I am earning more points with certain things than I was before- i.e. I get 5x points by paying my cable bill with it (yeah only $35/month but still not bad), and 2x for buying gas with it ($70/month or so for me).

(If anyone has ideas on how to now do the Guillebeau system, I’d love to hear it. Apparently he shuts down comments on his posts once they get over a certain number).

I also have the advantage of owning real estate. The downside is that when you own houses, stuff routinely breaks. Heaters, air conditioners, pipes, fences, refrigerators….you name it, houses are like ticking time bombs. So when I can, I will use my credit card to pay technicians and to replace items. It makes those surprise bills sting a little less when I know I’m earning points with all of these purchases.

The key is to use miles on the longest trips. So for example, when I went to Bali last year, I only spent 32,500 miles to get there. Even a flight to New York would cost me this much, and that’s about 6000 miles closer!

And then there’s local travel hacks. I’ve recently begun using This is a site where you can rent out a room or a place to people. Since I have a desirable location right by the beach, I get a ton of emails from people on the site. So, if I accept someone and they stay at my place, I can leave and have my rent paid for plus my trip where ever I go paid for.

For example, I’m charging $95 a night for my place. If you average out my rent, it’s around $33 a day that I pay. So I’m playing a little arbitrage game. This last time I had guests, I just stayed with a friend downtown. It was just two nights and I pocketed $184. The next one will be 5 nights and I will get $412 total. I’ll probably couch surf, maybe hit the desert or the mountains one or two of the nights.

This summer, I aim to be in Colorado for at least some of it. And I won’t be paying much to live.

And I won’t be wearing shoes. 🙂

Picture of Kevin Koskella

Kevin Koskella

Kevin is a podcaster and writer on living free, despite the crazy world we live in. Kevin travels full time and explores the world and how to achieve and maximize freedom in life.

Check Out The Upcoming Book

Share the Freedom!

Posts you may like