I started my mileage journey when I got approved for a Chase Sapphire card in May of 2015. It was my first credit card in 27 years. (That’s a story for another time…) I jumped into the mileage game with both feet in September 2015. In the next 18 months, Molly and I were approved for 55 different cards and earned well over 2 million points in various programs plus about a dozen free nights at Wyndham Resorts, Fairmont Hotels and Hyatt. I’ve learned a lot in the first year and a half and there are things I would do differently if starting from scratch. Here are a few of them
1– The first thing I did when I decided I was going to hit this hard was sign up for an online course to speed up my learning curve. I am a strong believer in investing in yourself, but the $500 I spent on the course probably could have been better spent elsewhere. I did learn a lot of valuable information, but nothing earth-shattering that I couldn’t have learned on a dozen different travel blogs for free. A lot of the specific deals with each airline and hotel chain are constantly changing, so there was a lot of outdated information by the time they had videos made up and started selling the course. My advice would be to start following a few good blogs and you can always post questions on them where a multitude of savvy travelers will help you out. Click here for a list of some of my favorites that I subscribe to.
2– The next 2 go hand in hand. One of the best deals in free travel is the Southwest Companion Pass. If you have a Companion Pass, anytime you book a Southwest flight whether you use cash or points you get a free ticket for your companion. All you have to pay is the tax on the flight which is typically $5.20. No blackout dates or limit to how many flights you can take. It’s a pretty sweet deal. Click here for more details. The Companion Pass is good for the year you qualify for it and the next year which brings me to my mistake. I wasn’t thinking straight and qualified for it in December 2015. Stupid, Stupid, Stupid. I guess we did use it in December to fly to Portland for Christmas, but it would have been much better to have waited until January. Then it would have been good all of 2016 and 2017. We used it for 6 or 7 flights last year, so it still saved us well over $1,000, but it would be nice to have it this year as well.
How do you get a Companion pass you ask? Simple, all you need is 110,000 points on your Chase Southwest credit card in a year. If spending $110,000 on a credit card seems a bit much there is an easier way. Chase has 3 different Southwest credit cards. 2 personal cards and 1 business card. Currently there is a 60,000 point sign up bonus on the business card and a 50,000 bonus for the personal card. Those points count towards the Companion Pass. So all you have to do is get those 2 cards, pay the annual fee of $99 for each card spend $2,000 on each card in 3 months and you have a Companion Pass and 114,000 points, which is enough for 8 round trip tickets pretty much anywhere in the US. Not bad for $200…
3– This brings us to my third mistake. Not a mistake so much as not having a proper strategy. Last year Chase implemented a new rule that really sucks. If you have gotten 5 or more new credit cards from ANY bank in the last 24 months, Chase will not approve you for most of their cards. This sucks because Chase has some of the best travel cards out there. Chase Sapphire, Sapphire Reserve, 2 Ink Business cards, 3 Southwest cards, 3 United Airlines cards, Chase Freedom, Chase Freedom Unlimited and a few more. That’s at least 12 cards that would be nice to have that are affected by the 5 in 24 rule. When you start the mileage game, you need to start with Chase and figure out what 5 cards you most want. For me, the most valuable travel card available anywhere is probably the Chase Sapphire. It is a card I’m happy to pay $95 a year for. (The annual fee is waived the first year) The Sapphire Reserve is probably the second card I would get. They had a 100,000 point sign up bonus that just expired, But if you are going to do any traveling in the next 2 years the $450 annual fee (not waived) is well worth it. My next choices would be a personal Southwest card and the Southwest business card, which brings me to another point. The 5 in 24 rule doesn’t count most business cards including their own, so if someone wanted to take a less aggressive approach than I have, there are a lot of great business cards out there that wouldn’t affect your Chase eligibility. This brings me to the card I really wanted but couldn’t get because of the new rule which is the ink Business Cash card. The main benefit to me would be the 5 X points on purchases at office supply stores. At first I didn’t understand why people cared about that. How many envelopes do you need in a year? But office supply stores sell all kinds of gift cards including Visa gift cards. A conversation for another time, but there is something you will see on sites talking about MS, manufactured spending. A quick example, for the Ink business card after you spend $3,000 in 3 months, you get $300 cash back. What some people might do is go to an office supply store or if you’re really Savvy go to Swagbucks.com and use their online portal to link to Staples for another 2% cash back, buy $3,000 in Visa gift cards, take the gift cards to the post office and get a money order made out to yourself, then deposit it into your checking account and use it to pay off your Ink credit card. Staples $300 gift cards have a $9 fee, so you would be out $90 in fees, but get back $210 plus the $300 sign up bonus so you would still be up $420. That’s more than enough for a rental car for a couple of weeks in Hawaii.
4– Next on the list is American Express. They have a ton of great cards but they have a rule that you can only get a bonus once in a lifetime for each card, so the simple rule here is to only apply for an AMEX card if the bonus is at or close to an all time high. I got a few of their cards with some lame bonuses because I didn’t know better.
5– I should have been more patient when getting cards for Molly. A lot of cards will give you a referral bonus for each new person you refer that gets the card and earns their bonus. So what you should do is before you apply for a new card check to see if I can get a referral bonus 😉 then if you have a significant other, refer them so you get a bonus and they get a bonus. There are a bunch of cards I didn’t do that with and wasted probably 50,000 points.
6– I also missed out on some free points by not adding an additional card holder to some accounts. A lot of cards will offer something like a 5,000 point bonus for adding an authorized user when you apply. Tristan, my 16 year old son now has about 10 credit cards with his name on them. (They live in my safe, not his wallet.)
7– I wish I had gotten a premium credit card earlier. If starting now I would get the Chase Sapphire reserve first. It’s $450 a year, which might seem like a lot, but it’s well worth it. For starters it has a $300 a year travel credit. That means if you got the card now, and spent $300 on any travel related expense like hotels, car rentals, airline tickets or anything that is coded as travel they will automatically reimburse you for the first $300. Oh you also get 50,000 points, and a Priority Lounge Pass https://www.prioritypass.com/ I will always have at least one card that gets me into lounges. I had never been into an airport lounge until last year. Now so far, I have been in 23 different lounges in 6 countries and I’m really looking forward to hitting up some Centurion Lounges this year with my AMEX Platinum card. http://thecenturionlounge.com/locations/SFO SFO next month on the way to Sonoma, LAS this summer and DFW and MIA in October on the way to the Dominican Republic. Free alcohol, food and comfy chairs. I’m now bummed if I only have a 45 minute layover. Last October we had a flight delay coming back from Maui and Tristan and I ended up hanging out for 5 hours at the Korean Air Lounge at LAX and had a great time. http://onemileatatime.boardingarea.com/2014/02/16/review-korean-air-lounge-los-angeles-airport/
Get a card with lounge access!
8– Another benefit I missed out on was Global entry https://www.cbp.gov/travel/trusted-traveler-programs/global-entry Pretty much all premium cards reimburse you for getting global entry. It’s $100 for 5 years and lets you go through TSA Pre check in the US and skip the long lines of customs coming back into the States. I paid $300 out of pocket for Molly, Tristan and I and I have now had 3 cards that would have let me have it for free. Worked out well for my mom and sister at least.
9– Pay attention to your credit score. For a very long time my mantra was “I don’t care what my credit score is because I don’t want credit because if I can’t get credit I can’t get into debt” That actually was a good thing for me for a while, since I did have some challenges with debt in my youth, but had I known how much free travel I was missing out on I would have been a bit more pro active with my credit score. Being self employed in the construction business I noticed more than a small change in my income from 06 -09 that didn’t help boost my credit score, so I never looked at it for years and was amazed when I got approved for the Chase Sapphire card. That got me to start thinking that I could start playing in the mileage game. Since then, 37 personal cards later, my credit score has actually gone up about 80 points and I have a very scary open line of credit of $390,000 on my various cards.
10– The last thing I try not to dwell on is I SHOULD HAVE STARTED SOONER!!! I’ve always dreamed of traveling the world, but I always thought I needed to sock away a boat load of cash before I could even dare to start thinking seriously about it. Now my biggest problem is making the time to go travel and the fact that being self employed I don’t have any paid vacation. If anyone reading this gets paid vacation and you stay at home, shame on you, because if you didn’t want to travel more you probably wouldn’t have read all of this. A trip to Hawaii for a week? Easy and cheap. Molly and I are going to Kauai for a 10 nights in May. $20.80 for airline tickets, $50 in resort fees for hotel and $311 for a car. I figure I would probably have to eat if I stayed home, and I now have status at the hotels so we get free breakfast everyday. I just got a Barclay Arrival Plus for Molly that has $500 in free travel credit so the $382 will be covered. 10 days in Kauai for the cost of food will leave some money left over for FUN because adventure is fun!
