76. Your Mid-Year Points Check-In: How to Evaluate and Recalibrate Your Strategy

Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher-than-average expenses to travel the world. I'm your host, Devon Gimbel, and I believe that your expenses are your greatest untapped asset if you know how to leverage them. Ready to dive into the world of credit card points and miles so you can travel more, travel better, and travel often? Let's get started.

Hello everybody, and welcome back to another episode of the Point Me to First Class podcast. I hope you're having a great Monday if you're listening to this episode on the day that it airs, or a great other day of the week if you're listening any other time. How are you all doing, and what's going on in your points life right now?

What's going on in my points life is that I am preparing to go and sit down and do a little bit of a points check-in with myself. This is something that I usually do twice a year, once in January and then again in August or early September, and I wanted to share that process with you all so that you can take, steal, or use whatever portion of it you find helpful. 

In this episode, we are going to cover what a points check-in is, what you can get out of doing them, and how to do one so that you can get the most out of it. Whether you're brand new to points or a seasoned points traveler, this exercise is one that anyone can benefit from. 

But one thing that I want to be sure to note is that while I personally love things like checklists, planning, and organization, you might not. You can be incredibly successful at points without doing anything that I say. So if nothing about this process appeals to you, please feel free to ignore it.

But getting back to our topic. Of the two points check-ins that I routinely do every year, the initial one in January is where I lay out my goals for what I want to accomplish with points for that upcoming year and how I plan to do it. I look at how many points I want to earn in which specific points currencies in order to book the award travel that I'm most looking forward to, and I make decisions like creating a rough timeline for applying for any new credit cards that I already know I want and laying out a roadmap for how I want to allocate anticipated personal and business spend, especially large expenses, so that I can meet the travel priorities that are the most important to me. 

Doing this at the beginning of the year is a great way to know where you want to focus your points earning and how you want to leverage the spend that you anticipate having during the year so that you don't miss any opportunities to maximize what your expenses can do for you. 

I also repeat this process every year in January because my travel goals and priorities don't stay exactly the same from year to year. So even if I had a points plan that worked spectacularly one year, that doesn't necessarily mean that I want to do the same thing again if the types of trips or award travel that I want to book the following year is significantly different. 

January is also the ideal time to create a points plan for the calendar year because there are a lot of loyalty programs and credit card perks or benefits that run on a semi-annual or annual basis. So creating an annual plan at the beginning of the year puts you in a great position to ensure that you're taking advantage of those opportunities or setting yourself up well to hit milestones in hotel or airline loyalty programs for earning status if that happens to be one of your points priorities for that year. 

Now I'm going to briefly walk you through how I create a points plan at the beginning of the year and then discuss how I use that to do a Q3 or third quarter points check-in toward the end of the summer and what exactly my Q3 points check-in that I'm going to be doing soon entails. 

Now if you have never thought about making a points plan before or are sitting here thinking, wait, it's already August, and I don't know what my plan was for this year, please don't worry. You can absolutely still benefit from doing a mid-year or Q3 check-in, and you can save this episode and re-listen to it at the beginning of next year if you want to do this process from the start at that time.

But in a nutshell, here are the four things that I do during my initial points planning session or points check-in in January. First, I take inventory. Second, I make a rough list of all of my points goals for the upcoming year. I don't limit myself here, I just get them all out. That's because third, I narrow down and I pick my top two points priorities out of everything that's on the wish list that I just made. Fourth, I make a rough plan to accomplish those top two priorities. 

So here's just a little bit more detail about what goes into each of those steps. So first, when I do my inventory, this is what it looks like. I pull out all of my current rewards credit cards so that I know exactly what my current credit card portfolio looks like.  I check all my current points balances, including the balances in each of the transferable points currencies I have, as well as balances in any individual airline or hotel loyalty accounts that might have points or miles sitting in them. 

Second, like I said, I make a rough list of all of my points goals for the upcoming year, basically anything that I would love to do with points, including travel that I want to book and whether there are any loyalty programs that I want to make a concerted effort to earn or maintain status in. 

Now, I tend to book a lot of my travel and my family's travel a year out. So in January 2024, I had already booked a lot of our actual 2024 travel. But that's the time that I actually start thinking even farther ahead about what points trips we might want to take in 2025 that I want to put myself in a good position to begin booking during the 2024 calendar year.

Then third, out of that whole list of points goals that I made in the prior step, I narrow down, and I pick my top two priorities because that is where I'm going to focus first in terms of making decisions around how to earn points that year or what needs to happen in order for me to be able to make those really top priorities possible. 

Fourth, I create a rough plan for how I'm going to accomplish the top two points goals that I chose in the prior step. So that plan can include things like identifying specific points currencies that I need to earn more points in and then deciding how I'm going to do that, either by using the current rewards credit cards that I have or choosing specific new rewards credit cards to apply to during the year and deciding when to do that based on my anticipated spend patterns.

Basically, I look at strategizing how to use my current or new rewards cards to earn the number and type of points most important to me to reach my top points goals. Another thing that I do here is that I make sure to note any credits or perks that are available on my current rewards cards that I want to make sure to take advantage of, and I make a rough plan or timeline of when and how I'm going to use them so that I don't run the risk of having them expire just because I completely forgot about them during the course of the year. 

So really, most of my planning work for the year is already done in January and then I just go about executing that plan in the subsequent months. Again, I want to note that the reason I do this is because it works for me. This is helpful for me. Any piece of this that sounds, I don't know, like torture to you or that wouldn't work because of the way that you plan your own travel, use whatever I offer here if and to the extent that it does apply to you and is helpful for you.

Now once I've made that plan in January and just go ahead executing them, I've found that doing a mid-year or a little later than mid-year check-in can be just as beneficial because it's an opportunity to evaluate if I'm on track to hit my points goals for the year while there's still more than enough time to course correct if I need to. It can be really disappointing to realize in November or December that you are really close to hitting some big points goal but that you only have a limited amount of time or a limited amount of spend available to you in order to get that done, and it's just not enough. 

I am not a last-minute person. So I find that it is so much easier for me to do this type of check-in, again, not at the very end of the year but a little bit before that so I still have time to recalibrate or to course correct if I need to. 

The other reason that this is a great time of year to evaluate where you are in hitting your points goals is because the last quarter of the year has some important points milestones that you might want to begin prepping for now if they apply to you. 

This includes things like getting yourself prepared to apply for Southwest credit cards if you want to earn a Southwest companion pass in early 2025, making sure that you are ready to capitalize on paying quarterly estimated taxes that are due in September if you have those, and looking ahead to your anticipated holiday spending so that you can maximize the points that you can earn for what can be a spendy time of year for some folks. Going through a simple points check-in checklist like we're going to cover today in August or September can make a world of difference instead of waiting to do this, again, later in the year.

So doing this is going to ensure that you are making the most out of your upcoming expenses in terms of using them to achieve your most important points priorities. So now that you know why I think doing a third quarter points check-in is so valuable, in the rest of today's episode we are going to cover a simple process that you can follow to do your own points check-in. 

Doing this now is going to put you in a great position to take advantage of being prepared so that you can meet your points goals for the year. Like I said before, you can do this even if you didn't make an annual points plan back in January or have never even considered having a points plan before. 

The good news is that doing a third quarter points check-in is fairly straightforward. There's only two main steps to complete. First, you take inventory, and second, you either stick to your current plan or adjust your plan if you need to in order so you can hit your most important points goals. Now we're going to walk through what specifically to do in each of those two steps, starting with what to include in your inventory. 

There are four main things that I like to check during the inventory stage of a Q3 points check-in. First, check your current points balances for all of your open accounts. So this is going to include transferable points balances for each currency if you have more than one, as well as the points or miles balances on your individual airline frequent flyer accounts and hotel loyalty accounts, as you may have points spread across all of these. 

Now, if you're old like me and you know how to use a pen and paper, you can just write out a running list of all of your points balances. Or if you were born this century or just generally prefer modern conveniences, you can also do this using a spreadsheet or other document on your computer, whatever works best for you. This happens to be one of my favorite parts of doing a points review because there's something really fun and dopamine inducing about seeing all of your points balances laid out like little digital treasure coins. 

Once that's done, the second thing that you're going to want to note are all of your current open rewards credit card accounts, paying special attention to whether you are still working to meet the minimum spend requirement to earn the welcome bonus on any one of those cards. This is also a good time to review each of your rewards credit cards to remind yourself which ones offer annual or semi-annual credits that you want to make sure to take advantage of, and whether or not you've already used them. 

Now, you can obviously take whatever approach you want with all of the various potential credits that you might have available to you based on the number of credit cards you have and the type of credit cards you have. Personally, I don't really care about most of them, and I don't make any special effort to chase down every single $10 monthly dining credit or obscure software credit.

But I do make an effort to know what credits are available on each and every single one of my cards and then decide on purpose which ones that I want to be sure I utilize and take advantage of by the end of the year if I haven't already by this point. 

For any credit card I have that offers a credit that I want to be sure to use at some point before it expires, I write down what that specific credit is, and then I just put a checkmark next to it if I've already used it. So once I've made my list, if there's no checkmark next to an individual credit then I know that that is something that I'm going to want to include in my plan in step two that we're going to cover in a little bit.

For those of you who have hotel co-branded credit cards, remember that you might have things like a free night certificate or lounge or suite awards that will expire if you don't use them by a certain date. Different rewards credit cards offer a plethora of annual credits or benefits that can expire if you don't use them. So it's worthwhile to check each of your credit cards individually and note their specific benefits and when they need to be used by.

So on my inventory sheet, again, after all of those points balances are written down, I note for each of my individual rewards cards, whether they have a welcome bonus that I'm still working on earning and which specific credits or benefits they have that expire at the end of the year that I actually want to make an effort to take advantage of. That way, it's really, really easy to see what welcome bonuses I still have to earn or what credits or benefits I haven't used yet that I want to be sure that I do before the end of the year. 

The third element of taking inventory is to track your progress towards reaching the annual points goals or priorities that you laid out in January or that you just know that you want to reach by the end of the year. This can include things like how close you are to having a certain points balance if there is a particular number that you want to hit for an upcoming award booking or how many points you have left to earn before you reach that goal. 

This is also where it's helpful to track your progress towards earning status in any airline or hotel loyalty program that's important to you since many of these have multiple tiers of status and increasing and very specific eligibility requirements that you have to meet at each tier. I think for most of us, it's really hard to just accidentally earn very high levels of status in loyalty programs without intentionally meeting those status requirements. But if you're someone who is able to do that, that's great. 

But for the rest of us, this is a great time of year to gauge where you are now in terms of your status eligibility requirements and what specifically you have to do by the end of the calendar year in order to earn the level of status that you're shooting for. This assumes that the loyalty program that you're focused on earning status in operates their status on a calendar year, which many but not all do.

So even for loyalty programs whose status year doesn't run exactly from January 1st through December 31st, taking a quick inventory of what qualifying activities you still need to complete before the status year ends for that program can be worthwhile. I think that this is a good time to mention that there are tons of different goals that you can have for points, and it can become confusing or overwhelming to try to be working on 10 different ones synchronously all at the same time. 

This is why I find it helpful when I'm doing my initial points check-in in January for me to clarify my top priorities for the year. Again, I tend to focus on two of them. You can focus on as many as you want, but I do think it is helpful to narrow down that focus. I know that I can always have more goals or add goals down the line. But by identifying the ones that matter the absolute most to me, it helps me to focus all of my points-earning activities during the year to make sure that if nothing else, I'm on track to accomplish the points goals that matter the most at that time.

When I sat down in January of this year, the two points goals that were the most important for me that I really wanted to focus on for this year were, number one, to boost my Chase points balance as much as possible, and number two, to make sure that I re-qualified for Globalist status in the Hyatt Loyalty Program because that's a status that I benefit tremendously from and I want to continue to have it at least for another year. 

Knowing that those were where I wanted to focus this year made it really easy for me to decide how best to leverage my personal and business expenses and not get distracted by tons of other appealing points opportunities, at least until I had accomplished those two things. That's because most of us, even if you do have high spend or a lot of expenses that you get to leverage in order to earn points or put on rewards credit cards, most of us don't have unlimited spend. So we do have to be deliberate about where our spend is going in order to have the biggest impact based on what we're trying to accomplish at any given time. 

But once you know if you're on track to meet your most important points goals, then you have the opportunity to use the rest of your annual spend or upcoming spend to reach new points goals if you want. For my two biggest points goals this year, earning as many Chase points as possible and re-qualifying for Hyatt Globalist status, here is where I stand right now.

I need to earn 60 qualifying nights through Hyatt's Loyalty Program by December 31st in order to keep my globalist status for another year. Right now, I have 56 qualifying nights already earned. Looking ahead to what I have planned for the remainder of the year, I have another 17 nights of Hyatt stays booked. So I already know that I will easily re-qualify for Globalist status and meet that goal. 

That also means that from now until the end of the year, I don't have to worry about allocating any of my upcoming expenses to put on a Hyatt credit card in order to help me earn status. So I'm free to put my spend on other cards that will be more valuable. This is great because Hyatt credit cards themselves aren't very strong points earners for most expenses compared to other cards that I have. So I don't like putting any more spend on them than is absolutely necessary once I know that I'm going to re-qualify for Globalist. My spend is better used and better allocated to other cards in that situation.

In terms of my other points priority for this year, which is to earn as many Chase points as humanly possible, I'm not done with that goal. So I still want to use as many of my upcoming expenses as I can to maximize my Chase points earning for the rest of the year. So that goal is still in progress and is not yet done.

Once you've walked yourself through determining how far along you are in accomplishing your most important points goals and what you still need to do in order to get all the way there, the fourth and final piece of inventory you want to take is what do you have to work with between now and the end of the calendar year in order to meet your points goals. 

This is where I take note of things like how much estimated spend do I have for the remainder of the year, including any large upcoming expenses and what do I think my spend is going to look like by category. Please note, this does not have to be down to the minute detail. You don't need to try to figure out every single latte that you expect to buy in the next four months. 

But you do want to note if you expect to spend $300 on holiday gifts towards the end of the year or $3,000, or if you have an estimated tax payment due in September that you can leverage to earn points or other large expense coming up. 

Likewise, if you're aiming for status in any loyalty programs, this is a good time to note if you have any travel already booked or that you need to book for the remainder of the year that's going to help qualify you for status, including any booked flights or flights you need to book that will earn you miles or segments towards airline status or any hotel stays that are already booked or that you can book that are going to count towards earning you hotel status.

Your remaining spend for the year or any upcoming travel that you need to book, these are all resources that you get to utilize in order to make your top points priorities a reality. Knowing these things becomes very, very helpful when you're making decisions because you have multiple options available to you for how you want to spend money in terms of the card you want to put that spend on. 

Or if you know that you have a business flight that you need to plan, and you've got options of multiple different airlines, knowing what your priorities are are really going to be helpful in terms of eliminating some of those options and really helping you focus on the ones that are going to be the most advantageous for you so that you can make sure that you're putting all of that spend or all of those activities where they're going to have the biggest impact.

The entire purpose of the inventory step of the points check-in is to get an accurate picture of where you are right now, where you want to be by the end of the year, and the assets that you have available to you to leverage between now and the year's end in terms of expenses that you have upcoming and activities already booked or that you need to book that are going to help qualify you for status depending on what your main points goals are. 

Once you've done that, the inventory stage is over. Now you can move on to the making a plan stage. This should be fairly straightforward because at this point you should have a clear picture of whether you've already achieved your points goals for the year, and if you haven't, how far away are you from reaching those goals and what specifically is left for you to do in order to close that gap. 

So let's look at two different scenarios and talk about what making a plan for the remainder of the year could look like and what to keep in mind as you work through making your own points plan for the next few months. 

So scenario number one. This is for people who realize after the inventory stage that you've already accomplished your main points goals for the year or for people who maybe don't have one specific goal that they're working towards right now. I just want to note that it's not at all a problem to not have one specific clarified goal that you're working toward or to not yet have a specific driven mind that's guiding what type of points or how many points you need to earn. 

Because instead, if you're in this position, you have the freedom to just take advantage of any individual points earning opportunity at any time. This could look like leveraging your remaining spend for the year to open up one or more new rewards credit cards just based on the best welcome offers that are currently available. It can also look like just using your existing rewards credit cards for your spend for the rest of the year, just being sure to use whatever card you have that's going to earn you the most amount of points for any given expense based on its category. 

The key for folks in this scenario is just to earn as many points as you can for the remainder of the year. At any point in the future, when you have a more clear idea of a trip that you want to book using points, you can always focus or adjust your points earning plan at that time to accommodate that. 

Now, scenario number two is for folks who have a specific points priority that they're working toward, but they haven't reached it yet. What you want to look at is how can you use the spend that you have for the rest of the year or how can you use other resources like cash flights that you need to book or hotel stays that you need to plan in order to have the highest impact on closing that gap between where you are right now and where you want to be with your points goals.

So here's just one example. Let's say that you are aiming to earn 400,000 American Express points by the end of December this year so that you'll have enough points built up so that you can book two roundtrip business class flights to Asia in December of 2025. 

So after you run your inventory, let's say that you currently have 250,000 American Express points. Then you know that all you have left to do is make a plan for how you're going to earn the remaining 150,000 Amex points that you want over the next few months so that you're going to be ready to book your flights as far in advance as possible when those booking calendars open, and that you're already going to have earned the number of points that you wanted to to make it easier for you to have options of the flights that you want to book. 

So from here, you get to choose whatever path you want to take in order to earn the amount of points that you've identified that you still need. As you probably know by now, there are multiple points earning approaches, and you get to pick any one or combination of ones that are going to work best for you in order to reach your points goal in the time that you have based on how much spend you have to leverage. 

So one option for this could look like just opening one new Amex card that offers at least 150,000 points as the welcome bonus and being sure that you meet that minimum spend requirement in the next couple of months so that those points post to your account. 

Another option is to intentionally utilize American Express' affiliated online shopping portal, Rakuten, for all your online shopping purchases for the remainder of the year in order to generate extra Amex points that way. You can also take a look at your anticipated expenses for the remainder of the year and leverage the bonus categories available on your current Amex cards to ensure that you're optimizing your points earning that way.

This can also be a scenario where even if you have rewards credit cards for multiple different points currencies, you may choose to allocate all of your spend, preferentially to cards that earn one specific currency for a designated period of time, because those are the points that are most valuable to you for an upcoming trip that you want to book. 

So the benefit of there being multiple ways to earn points is that you can pick and choose which approach or approaches are going to be the most high yield for you based on how much spend you have in the upcoming months and where you can get the biggest impact for that spend. 

While I don't have saving for a specific trip as one of my top priorities this year, like I mentioned before, I do want to earn as many Chase points as I possibly can. So, that's part of my points planning part of this whole check-in. I don't have a specific number of points that I'm trying to get to. I just want to focus on earning Chase points preferentially over other points currencies right now because that's the one currency that I have been using the most of recently and that I consistently have the lowest balance in.

So, for me, here is what my plan looks like for the goal for the rest of this year around this priority. So I've already opened up a few Chase business credit cards this year and earned the welcome bonuses on those. So I'm not really eager to open up any more new Chase cards over the next couple of months. Instead, my plan for the rest of the year is to allocate all of my upcoming spend to the Chase credit cards that I currently have and to optimize my points earning by leveraging those cards' various bonus categories. 

So even though I have credit cards in other points systems like American Express and Citi and Capital One, and that for any individual expense, one of those other cards might actually have a slightly higher bonus points earning rate than one of my chase cards, I'm okay with that. I've still made the decision that I want to preferentially allocate all of my spend to Chase cards because right now those are the points that I have the least of and that I want to earn the most in. 

So just notice that it's not always necessarily about what individual card is going to give you the highest points earning for what individual expense. It really can be your priorities at that time that help you determine where is that spend actually going to have the best impact for you. 

So, for me, I'm looking at the rest of the year, and I know that I have a couple of upcoming large expenses that are all non-category spend. So I'm going to rely primarily on using our Chase Freedom Unlimited card for non-category personal expenses and a Chase Ink Business Unlimited card for non-category business expenses to earn as many points as possible from those. All dining and travel expenses are going to go on my Chase Sapphire Reserve card, and I'll also likely creatively use the office supply bonus category on my multiple Chase Ink Business Cash cards in order to earn extra Chase points. 

Now, because I know that I'm already set to re-qualify for Hyatt Globalist status this year, which is my other main points goal, like I mentioned before, I know that I don't have to allocate any of my upcoming business expenses to my Hyatt Business credit card. Instead I can funnel all of those to my Chase Ultimate Rewards points earning cards so that I can maximize my Chase points earning. 

But for those of you who have earning status in an airline or hotel loyalty program or potentially even more than one at the top of your points priority list for the year, this is a step where you want to make sure that you plot out exactly how you're going to meet the status qualification requirements by your program's annual deadline.

Many loyalty programs have multiple activities that actually do count towards earning status and so you'll want to make sure that you understand first, anything and everything that does qualify you for status as a qualifying status activity and map out the easiest way for you to fulfill the remaining eligibility requirements that you need to in order to hit the tier of status that you most want. 

Now, the last thing to include in your planning stage is when and how you want to take advantage of any of those credits or benefits that you still have left on your various rewards credit cards. If you have remaining free night awards for any of your hotel credit cards or loyalty programs, when can you plan to use those before they expire? 

If you have store credits or program credits on any of your credit cards that you haven't used yet, do you already have things in mind right now that you want or need so you can put those credits to good use, or do you want to save them to use a little bit later in the year and just be sure to set a reminder in your calendar so that you don't forget about them and then lose them? 

Remember, I don't personally think that it's necessary to use every last credit possible that's available on all of your different credit cards unless you want to, but the purpose of taking an inventory and making a plan is so that you don't miss out on using a credit or benefit that's actually really valuable to you just because it slipped your mind.

There you have it. Once you have your plan, you should know exactly how you want to use your expenses for the rest of the year to have the biggest impact in helping you reach your most important points goals. I have found that over the years of earning and using points, taking time to do a third quarter points check-in has been incredibly helpful for me, and I hope that you've heard something in this episode that will be helpful for you as well. 

Walking through this process of taking just a little bit of time to see exactly where you are in reaching your points goals, what's left in order for you to get there, and laying out a plan to follow really helps to eliminate the guesswork of what you should be doing with your expenses and also significantly decreases the chance that you miss out on taking advantage of credit card credits and benefits that are actually really useful for you. 

As always, use whatever in this episode is helpful for you, but please don't think that you have to do things exactly the way that I do, or that if you have your own process that works better for you that you should change it. Not at all. Anytime I offer anything on this podcast, it's just a suggestion. Take what works and leave the rest. I hope that you are all well on your way to reaching whatever points goals that you have for this year, and I'll see you again same time next week. Have a wonderful week, everyone. 

Thank you for joining me for this week's episode of Point Me to First Class. If you want more tips on turning your expenses into travel, visit pointmetofirstclass.com to learn more. See you next week.