Frequent Miler’s next challenge: What should it be?


We recently wrapped up our 3 Cards, 3 Continents challenge where three of us competed to see who could build the most awesome 3-continent trip with the welcome bonuses from 3 cards.  That was just the latest of our Frequent Miler challenges.  In 2021, I gave Nick my Delta Global Upgrade Certificates (GUCs) with the condition that he bring me along and complete a series of individual challenges (earn elite status from the trip, collect KLM Delft Blue houses, get far outsized point value for stays, etc.).  In 2019 we competed to see who could go farthest with 40K points and $400.  Years earlier I challenged myself to earn enough points to stay on Richard Branson’s Necker Island.  Before that, I challenged myself to earn 1 million miles in 1 month.  And finally, in 2012, I challenged myself to visit New York City on $19 per day.

Now, the question is… what’s next?

a group of people playing a game

Challenge Goals

The purpose for these challenges is to push the envelope of what can be done with points and miles.  By igniting our competitive spirits and constraining us to strict limits, we’re forced to innovate new techniques or test the limits of known ones.  The best example of this so far is when Nick was constrained to using Citi ThankYou Points for 40K to Far Away. This, led him to discover one of the best redemption opportunities in existence: US mainland to Hawaii for only 7,500 points.  In most cases, though, we learn (and share) by taking advantage of known award sweet-spots and push those to the limit.  That experience provides great insights for us so that we can better inform our audience about these opportunities.  My recent use of ANA’s Round the World Award is a great example.  This was already a well known fantastic sweet spot award, but none of us had ever previously booked it.  Now that I have, I understand its pros and cons better than I ever did before and so I’m in a great position to help others decide whether is is right for them, and to learn how to book it (expect a tutorial soon-ish, but for now see this post).

Challenge Parameters

We’d love to hear new ideas for challenges from you.  Ultimately we want to do something that ticks these boxes:

  • The challenge must be possible and practical.  We won’t challenge to see who can circumnavigate the world with 5K points – that’s not possible.
  • The challenge must encourage rewards innovation.  The idea should be to push us to figure out new and better ways to earn or use rewards, elite status, credit card perks, etc.
  • The challenge should be entertaining.

My Thoughts

The following thoughts are not requirements for the next challenge, but rather are my current preferences.  I’m sure I can be swayed to do other things if great ideas are suggested that don’t include what follows.

Repeat the Card Draft (or Something Similar)

The 3 Cards, 3 Continents Credit Card Draft was awesome.  I loved everything about it.  The idea for it originally came from a reader in response to a post like this one.  And I’d love to do it or something similar again.  Here was my original write-up about the concept:

We loved Jarrod’s idea of a fantasy draft for selecting who gets which points and we’ve taken it a step further: we’ll be picking from real current welcome bonuses.  Whatever welcome bonuses are on our Best Offers page when the draft begins will be fair game.  Once a card bonus is selected, it’s gone.  The next players cannot pick it.  We won’t really be signing up for cards.  Instead, the cards we pick will define our points & miles budget for the challenge.

Our budget begins at draft time.  We each have a $1,000 budget for our travels, including first year annual fees.  So when the first player picks the Platinum 150,000 point offer, for example, that card’s $695 annual fee will count against the player’s $1,000 budget and leave him with only $305 left.  He’ll have to pick the next two cards very carefully!

We will also be limited to $15,000 credit card spend.  Most credit card welcome bonuses require lots of spend in order to earn the bonus.  In our made-up scenario, we have exactly $15,000 of unbonused spend available.  We can’t go above that.  So, for example, if someone picks the Chase Ink Business Preferred 100K offer which requires $15K spend, their next two picks will have to offer bonuses with no spend requirement (a bonus after first purchase is allowed) since the spend budget will be gone.

Using the leftover spend:  There’s a good chance that some contestants will spend less than $15,000 towards minimum spend requirements.  In that case, they can virtually spend the rest on whichever of the 3 cards they chose in the draft.  None of that spend will be in bonus categories, though.  For example, if I had $3,000 spend leftover and I had chosen the Capital One Venture card, that would be a good choice for my final $3K spend since it earns 2X everywhere and I’d end up with 6,000 additional points.

Explore South America

Our challenges to-date have taken us to Europe, Africa, the Middle East, Asia, and Oceana.  A big hole both in our challenges is with points & miles travel to and around South America.

Interact with Each Other

The GUC trip was particularly fun because Nick and I travelled together.  Can the next challenge include more interaction?  For example, maybe we compete in teams (e.g. Nick and Stephen vs. Greg and Tim).  Or maybe we could do challenges that require competitors to meet up in various cities?  Or maybe we do something that includes some readers?

Reader Participation

We’ve often discussed the idea of including readers in the challenge in some way, but we’ve never figured out a practical way to make that happen.  If you have ideas for this, please let us know!

Comment Below

If you have ideas for the next challenge, please post your ideas to the comments section below!

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4 continents – 4 months

Take a 1-week trip each month to Europe, S. America, Asia, Africa. Around 1 week each. Using miles/hotel points.

Add in family or spouse (or mix of both) for each trip.

This adds practicality: typical trip length, more than 1 passenger, and typical USA vacation duration.

This will show many uses of miles and points all over the world. Maybe have some contestants in economy and some in business class.

Each “team/couple/family” has to use a different airline alliance. Again some go business and some go economy.

This is the basic idea. Details can be worked out based on number of teams, 2 versus 3+ travelers, etc.

This will also force usage/highlight of sweet spots to save in terms of miles required.


I don’t know exactly what the competition would be but I would love to see Team FM vs. Team Jet Lag (on YT). It’s a collaboration that would span written media and YT and I think would broaden the audience for both teams.


Picking a winner is impossible because each trip is so unique. You need to design a series of challenges that can be compared. Going to a world cup game. Going to an F1 race. Last min getaway with your significant other. Five nights in the Caribbean. Whatever it is, it needs to be comparable or eliminate the idea of a winner. Loved the draft, was probably my favorite part of the last challenge. Would love to see some unexpected thing, like, after the draft, each of the other players gets to name a challenge the other has to complete or a wheel or randomness that each person must spin. I feel like the award charts dictate your competition a lot, and that is fine I love a great find. But if I don’t take my wife to Italy soon, she is going to freeze my credit report and not tell me the password. Seeing how you would overcome some of these travel challenges that people who have a job and can’t just go on vacation on a random Tuesday would be interesting.

[…] Frequent Miler’s next challenge: What should it be? […]

d *

I mentioned this before can’t remember but maybe at an FTU… My suggestion would be to pick a destination and each person does it with a different focus in mind. So Greg could plan with high end resort type bookings, Nick could plan with family in mind and Steven could plan for best value for a longer stay with a pet. Maybe readers can choose the focal points? Maybe Carrie is also able to participate?

There might be overlap so for example, Nick might still go for the high end suite or all inclusive bc it works great for family, while Nick might also overlap with Steven’s choice of a place with a kitchen that works for a stay where eating out isn’t happening every meal/day.

And it would be interesting to see how people plan flights/methods of getting to destination bc maybe there are other ways besides flying?

What’s interesting about this challenge is everyone goes to the same destination and there’s the potential for collaboration/help each other create the best trip.

One could pick a popular destination like Las Vegas or Florida beach/amusement parks, or national park/scenic destination.

The other idea that came up in the podcast was a meetup. So if everyone was going to the same place and it was an easy one for folks to get to, then a meetup would be relatively easy.

So anyway, not a competition but definitely a challenge and I think it helps readers to see how to approach a trip given their focus/needs.

Last edited 1 year ago by d *

I think it would be great to involve readers as both the contest creators as well as the final judges.
Imagine if once a quarter you picked a reader at random and competed to design the best trip for them.
The criteria would be based on where that reader wants to go, the size of the party they intend on taking, and their own individual points and miles totals. You could all three then try and create the best trip for them and let them decide the winner.
Then, they could actually take the trip that was designed for them and document it themselves.
It might help individuals learn how to create itineraries with fixed amounts of points (you guys always seem to have infinite amounts). It would always be unique as some people would have specific ideas of where they want to go, others would not, some people might be going solo or as couples, others as a family, some would want to go in luxury, others in economy. The variables would always be changing.

Mark H

I would like to see no more secrecy. Maybe it takes away a strategy element, but I think it would be more fun and informative to read about and hear you discuss your plans as you make them.

Spencer Pederson

As many other commenters stated, I think the idea of involving readers is great. That said, I think it would be cool to have a competition focused on the readers being the competitors. (maybe this wouldn’t be a “pushing the points and miles boundaries” challenge but it could be a another type of challenge next year).

Basically, my thought is this:

  1. Greg, Nick, Stephen, Tim, and Carrie (or any mix of the FM team), position themselves in unique locations around the world (i.e. a certain resort, lounge, airport, landmark)
  2. The FM team gives out hints before the trip to help readers figure out where they will be “hiding.”
  3. Readers are tasked with finding each of the FM team members, with the first reader to find everyone (and maybe take a selfie?) being the winner.
  4. Or instead of just the first person finding everyone, there could be a weighting towards who spends the least amount of points/most luxurious travel.

Obviously, my idea is predicated on the fact that readers would be willing to participate. I think to get readers involved, some reasonable prizes would be required, but I know for myself it wouldn’t take much for me to be willing to do something like this.

The challenge would probably need to take place over the course of no more than 7-10 days (since not everyone has unlimited time off from work).

Anyway, this was basically just a brain dump of my initial thoughts, but I love the challenges the team does each year and I’ll keep thinking to see if any other ideas come up!


I would love to see a trip where you guys piece together an around the world itinerary using the 3 alliances. A minimum of 2 legs on each alliance with a preset total amount of points for booking the itinerary with a different hotel program for each stop (or a single one for all stops) being utilized


Closest to Antartica. It brings in South Africa, Australia/New Zealand and South America.


I like the idea of involving readers, not just in the selection process, but in the travel part. How about determining your trips and have a get together party with readers for a couple of days at each of the destinations. Points for the person that gets the most readers with bonus points for each 1,000 miles away from, say, Kansas City. So if 10 show up 6,000 miles away, 60 bonus points toward the prize. I bet a lot will try to join you.

Anthony Fantino

You should do a Amazing Race style competition with a certain destination as the goal such as Singapore or Antarctica, especially if you want to focus on points and miles for South America, Antarctica as your final destination would be pretty neat. There has to be certain parameters such as you can’t fly non stop to the destination obviously. Set a certain limit to the distance per flight. For example your first flight can only be a distance of 5,000 miles for a destination like Singapore or far less for Antarctica as the final destination more like 3,000 for the first flight, and shorter distances for the next flights and also limit the amount of miles redemptions per flight and limit of the total number of flights. This might mean some participants might have to resort to other transportation, train, bus, rickshaws! An Amazing race style competition to Antarctica going through South America should be your next challenge! You could even do the same fantasy style draft like your did in the last competition.

Anthony Fantino

Just watched the new podcast, a way to get the readers involved, you could choose where you are starting and ending and have the readers choose your next destinations along the way, provided that you are able to find bookable options.


How about 2 cards, one nation? Travel as many of the 50 states with 2 cards. Can use points for hotels/flights/car rentals. If you drive, then have to redeem the points for the gas spend. But there has to be a cap on driving, so you don’t end up driving the whole time.
With the nation under a recession, and budgets tight, more families are opting for domestic travel.


I think u got more posts on this then your trip.

Last edited 1 year ago by Cavedweller

Co-brand to Copacabana:

Two teams of two each draft 3-4 cards plus a small budget to build the best South American trip possible with co-branded cards only, no transferable points or cash back redemptions.