Smart Money Podcast — Travel Smart, Give Smart: Southwest Companion Pass and Charitable Giving Strategies

Welcome to NerdWallet’s Smart Money podcast, where we answer your real-world money questions. In this episode:

Learn how to maximize Southwest Companion Pass benefits and how to plan effective charitable giving to make your donations count.

How can you get and use the Southwest Companion Pass? What’s the best way to plan charitable giving to make the most impact? Hosts Sean Pyles and Sara Rathner discuss travel savings and effective philanthropy to help you understand how to maximize rewards and make thoughtful donations. Sean begins by talking to travel Nerds Meghan Coyle and Sally French to discuss the Southwest Companion Pass, with tips and tricks on earning it through points and flights, timing it for maximum value, and using it strategically for travel savings.

Then, Sean and Sara talk to Grace Nicolette, Vice President at the Center for Effective Philanthropy, about planning and optimizing your charitable giving. They discuss how to align donations with personal goals, avoid common pitfalls like over-focusing on nonprofit overhead costs, and ensure your contributions have a meaningful impact.

Check out this episode on your favorite podcast platform, including:

NerdWallet stories related to this episode:

This transcript was generated from podcast audio by an AI tool.

Holiday travel season is in full swing, and as anyone who’s done a lot of travel can attest, travel can be a lonely experience. This episode, we’ll give you some tips so you can bring a buddy with you on your travels for free. Welcome to NerdWallet’s Smart Money podcast. I’m Sean Pyles.

We are in the thick of the holiday travel season right now, but for people who love Southwest Airlines, we are in a special season as well. I invited back our travel Nerds Meghan Coyle and Sally French to tell us about it. Later in the episode, we’ll talk with the Center for Effective Philanthropy about how you can make your charitable giving go even further. But Meghan and Sally, you are up first.

Always good to see you, Sean.

Thanks for bringing us back. We’re talking about one of my favorite ways to save money on travel.

All right, give us the scoop.

And this is a perk that is so different from anything other airlines offer. With this Companion Pass, if you meet the minimum requirements to actually earn one, you’ll be able to bring a designated companion with you on all your flights for at least a year. The duration of how long you hold it depends on when you get the pass, but once you have it, the best part is you will not need to pay full price for your companion’s ticket. All you pay is the taxes and fees. In most cases, for domestic flights, that’s $5.60.

It’s like a buy-one-get-one deal, and you don’t get to do this just once—you get to do this every time you fly Southwest for that period that your Companion Pass is eligible.

Okay, that’s a pretty sweet deal. But Sally, Meghan, we are at the end of 2024. Why are we talking about this now?

Now is a great time to start thinking about the Southwest Companion Pass. That’s because, if you play your credit cards right, you might be able to earn a Southwest Companion Pass for almost two years. I did talk earlier about the duration of time you own the pass. Basically, this is a smart time to think about it so you can own it for the longest amount of time. We’ll dive into that later.

But first, I do want to note at the outset that we’re going to talk about Southwest credit cards, which are issued by Chase. And Chase is a NerdWallet partner. I do want to note they are not paying us to talk about their credit cards. They don’t influence how we talk about them on this podcast, but I love this travel deal. I love the Southwest Companion Pass. We wanted to share it with Smart Money listeners, so just keep that in mind.

Awesome. Well, I will let you guys tell us all about it.

Thanks, Sean. Southwest is such a special airline in the U.S. Why don’t we talk about why this Companion Pass is so different from the other ones out there offered by other airlines like Alaska or Delta?

It’s important to note that many of the other “Companion Passes” that you see on airlines like Alaska or Delta apply to one flight. This is for people who can really game it. If they’re flying this premium flight on a really expensive itinerary, say they’re going to Europe, maybe that makes sense.

But what’s great about the Southwest Companion Pass is that you get to use it as many times as you can in the period that you actually own the pass. So if you fly with someone—maybe that’s your significant other, your parents, your bestie—this is a great way to save money on flights, especially if you do fly often with that person.

So who would you say really should consider getting a Southwest Companion Pass?

The Southwest Companion Pass is as valuable as often as you fly. So if you fly Southwest often—this is for people who live near an airport with a Southwest hub—then it definitely makes sense to try to go for that pass.

And that person doesn’t necessarily have to be a partner. It could be your kid. It could be a really great way to take advantage of family travel. Let’s say you and your partner had one and you have two kids. There you go. You have buy-one-get-one-free travel basically for your entire family.

That’s exactly right. In fact, you can change your designated companion up to three times in a calendar year. So typically, my companion is my fiancé. I have a Southwest Companion Pass, I’ll admit, but once I was doing a flight with another young woman on my weightlifting team, actually, and I’ve used it on her to get both of us to meets that we’ve done together.

A few things to keep in mind though. Southwest doesn’t fly to a ton of international destinations, so if you’re going abroad, you probably shouldn’t plan on using your Companion Pass for that.

With international travel, it does become trickier. Of course, there aren’t as many international destinations. The other thing that’s important to note is that we mentioned with domestic travel, you’re typically paying taxes and fees of $5.60 each way, but when it comes to international travel, you can often see taxes and fees so much higher depending on the destination. So sometimes we’ll see taxes and fees upwards of $100, which doesn’t really make the Southwest Companion Pass as good of a deal.

But there are a lot of ways to maximize the Companion Pass when you do have it. One cool way to use it is there are no blackout dates. You can literally use your Companion Pass on any flight. So this is a really good time to use it when prices are high. So for example, like holiday travel, maybe an expensive flight to Hawaii, that might be a really cool way to use it. And you can also use it when you book your ticket on Rapid Rewards points. So literally your companion can come with you when you’re booking an award ticket.

Now is a great time to strategize how you might earn these passes so they will be valid for the longest amount of time. Let’s just dive into first how you earn these Companion Passes.

To qualify for a traditional Companion Pass, you need to do one of two things. You need to fly 100 qualifying one-way flights in a calendar year, which, if anyone is listening and has done that, I would love to talk to you. That’s basically a flight every third day. Very few people are earning it that route.

Most people earn it the route where you earn 135,000 Rapid Rewards points in a calendar year. Of course, you can earn these qualifying points through revenue flights booked via Southwest. So you book a flight, you get points for it. You can also earn points on Southwest credit cards as well as base points you earn from Rapid Rewards partners. The Southwest credit cards one is a huge way to earn a bunch of points in one go, and that’s because of intro offers on these credit cards.

You have to time it exactly right. So these intro offers need to hit in the calendar year that you are trying to earn the pass in. For example, right now we’re at the end of 2024, but to get a Companion Pass that’ll be valid for the longest amount of time, you actually want it to hit in 2025.

You could apply for a card today. Maybe you get it in the mail later this week or next week. You can start spending on it, but you don’t want to meet the spending minimums to be eligible for the signup bonus until at least January, maybe even February, maybe March. You don’t have to rush, but it’s really important that it hits in 2025.

You can’t always time your spending exactly right. It’s difficult to hit it exactly, but you want to get those 135,000 points as close to the beginning of January 2025 as possible without actually occurring in 2024.

Once you have that Companion Pass, you have it for the following calendar year and then the next calendar year after that. If you think about it, if you earn this Companion Pass in January 2025, you’ll have it for the duration of 2025 and into 2026.

If you get too excited and you somehow earn all those points by December 2024, then it’s actually a bummer because you’ll only have it for the rest of 2024 and then 2025 as a whole, but you wouldn’t have it for 2026. So it is really important that you are targeted about when you actually earn this pass.

And I’m sure people are listening and they’re thinking, “135,000 points? I can’t get that with just a credit card.” And you know what? That’s okay because there are so many different ways to get it. You’re also earning these extra points when you use the credit card on Southwest purchases, on bonus categories like local transit, ride-share, internet, cable. There’s a lot of ways to earn extra points. And then, of course, any flying you might be doing early in the year next year — that’ll all count towards earning a Companion Pass in 2025.

Just a reminder that the only flights that qualify are ones that are paid entirely with dollars, or maybe if you have an extra voucher laying around from a canceled flight, but flights that you booked on Rapid Rewards points, those won’t count towards the qualifying flights.

And then I also do want to mention, just on that topic of qualifying flights, what does and doesn’t count. There’s another thing that is a common misconception—a lot of people think they can transfer Chase Ultimate Rewards points to Southwest and have that count towards their Companion Pass.

Now, you can definitely transfer Chase Ultimate Rewards Points to Southwest to have Southwest Rapid Rewards points, which is a really great transfer partner, but I do want to be clear, these don’t count towards the 135,000 points that you need to actually earn that Companion Pass.

And Sally, you’ve had one of these Companion Passes for a few years, is that right?

Yes. It really came in handy when my fiancé and I were going to a wedding. We actually intended to rent an RV to go down to the wedding, but the RV rental is a whole other story. It was complete chaos. The RV did not go through.

We had to book a last-minute flight. It was going to be $500 per person. That would’ve been $1,000 for us, which would’ve been so tough. At least with the Southwest Companion Pass, we were able to get both of us for $500. So we do really feel like that alone saved us so much money.

That’s Nerd math for you.

If you’re listening to this and you want to learn more, we’ve built a webpage. It’s nerdwallet.com/southwest. There’s all sorts of information there — more deep intel on how to actually earn it, which credit cards might help you earn it. That’s typically how I earn it.

So if you’re interested in learning more, visit nerdwallet.com/southwest. Sean, I think you’ve been lurking there. Do you have those pages pulled up?

I have been. I’m here and I have that page pulled up, and it’s actually a super handy resource. We’ll include a link to it in the episode description.

And I gotta say, flying Southwest seems like a great deal. I just wish that there were more flights out of Portland because my options are pretty limited here.

Okay, Southwest people, I know you’re listening. Sean wants more Portland flights.

Well, Meghan, Sally, thank you so much for joining us again and sharing all of your Nerdy travel insights.

Now let’s move on to my conversation with my co-host, Sara Rathner, and the Center for Effective Philanthropy. We’ve got loads of tips to help you give better this year. That’s coming up in a moment. Stay with us.

We’re back. In this episode, we are all about giving — philanthropic giving — because Giving Tuesday is coming up. We know a lot of people are feeling generous this time of year, but what’s the most effective way to donate to the causes that you care about?

To help us explore how to be better and more intentional about our charitable giving, we are joined by Grace Nicolette, Vice President of Programming and External Relations at the Center for Effective Philanthropy, an organization which works to help individuals and organizations make their charitable contributions go further. Grace also hosts the Giving Done Right Podcast from CEP. Grace, welcome to Smart Money.

This time of year, many are hoping to maximize their charitable giving, but they might not be sure the best way to go about it. Since you are a VP at the Center for Effective Philanthropy, I’m hoping you can start by explaining what it means to give effectively. Does it depend on what you want out of your charitable giving, or are there common themes across all kinds of giving that make it effective or not?

I think that effectiveness really has many dimensions. One major dimension is: is the money that you are giving having its intended effect? Is it being well-used by the nonprofit that you’re giving it to?

And I think that here is an area where, without realizing it, donors actually pick up a lot of “conventional wisdom” that actually may not serve their goals very well in giving effectively. You want to be as generous as possible to nonprofits. You want to do your homework in advance and then give so that you can unleash the nonprofits to do their best work.

That means, if you can, research nonprofits in advance. It’s hard to make a really big gift to a group that you don’t know very much about, and you don’t know whether their goals and strategies align with yours.

What’s an example of a common rule of thumb or convention around giving that might not actually be in people’s best interest?

The biggest one that we see is that donors really over-focus on overhead administrative cost ratios of nonprofits. There’s a sense in which nonprofits should have some sort of percentage of their operating costs that should be as low as possible. When we think about it, I know where that comes from, but actually, it doesn’t really serve a nonprofit well. You want to make sure a nonprofit has all the resources that it needs to attract the best talent, to have up-to-date systems, to be able to do their best work.

And it’s really hard to also just have one metric across multiple nonprofits. If you’re comparing a school versus an animal shelter, those numbers are going to be really different. So instead of looking at that one thing, because I think donors are often looking for, like profit for a business, what is that one thing that I can look at that can just tell me whether a nonprofit is good or not? And I think that it requires a lot more nuance and a lot more education to say no, there actually isn’t one thing—you have to really fully understand.

On a practical level, someone might be disinclined to give to a nonprofit or a charity if they hear about how much executives or the C-suite might be earning versus how much they’re actually making a difference at the organization’s goals. Is that right?

That’s right. Every holiday season I see a meme going around on social media with different nonprofit CEOs’ pay levels, and the lowest CEO salary of this one organization was purported to be $13,000, and that was supposed to be a good thing. And I look at that and I’m like…

How does someone survive on that?

Exactly. I’m not sure how that person is able to survive, and I’m not sure that organization’s attracting the best talent.

Grace, you mentioned doing a little bit of research into an organization’s goals, but on the CEP’s website you also talk about how effective giving can start with knowing your goals as a potential donor. So if somebody knows that they want to give charitably but they aren’t exactly sure what they want to support, how can they get some clarity around that?

This is really the biggest question, and sometimes it’s actually the hardest place to start, is for someone to actually sit down and write down, what are my goals? And one of the challenges here is also just right-sizing your goals with how much money you can give. It’s very tough to say, “Well, I would like to eradicate homelessness in my town, but I’m giving $1,000 a year.” That’s not in line with the scope of the issue.

Part of it is looking at how much do you want to give and what areas really touch your heart and your head? Start close to you, like what are causes that mean a lot to you and your family? How are you helped along the way? And start from there. Find what’s interesting and ask questions, talk to people, that kind of thing.

So do you think it is important for people to look at what’s going on in their individual community at a local level or maybe follow some of their ideals, or perhaps a mix of both?

I think all are needed. There really has been a big debate within philanthropy about whether or not you should always give, for instance, overseas. A lot of folks in the effective altruism movement would say that cost per life saved, dollar per life saved, would actually be the most important metric. We don’t believe that, and I don’t believe that personally.

I think that all are needed. I think that if we believed that we would never give into our own neighborhoods. We would never give to things that address beauty and justice around us. And so I think it’s an “and,” and not one or the other.

You mentioned the idea of metrics, which is something that is hard to grapple with sometimes. I think about how I give to local food banks, and I like seeing the metrics of “$30 a month is providing this number of meals for people.” But it can be hard to know exactly what your dollars are resulting in and what that means performance-wise. How do you think people can understand whether the amount they’re giving is making some kind of progress on whatever goals they may have?

The wonderful thing is, here in the United States, most nonprofits have annual reports and also tax filings, the 990s. You can actually look into their website just to see how they are spending the money. Usually, nonprofits are pretty clear on how they’re spending it. As a donor, I would say give in a way that gives a nonprofit the maximum flexibility. We know some donors who give to a food bank, let’s say, and will say, “Well, I only want it to go towards the food and not towards any of the overhead.” But actually, we saw specifically during COVID, that kind of flexibility for nonprofits is really key.

When kids were out of school, yes, they needed food, but they also needed tutoring and other support. Nonprofits are on the front lines, and if you can give in a way that is not restricted, it really helps them. If you have any questions, most nonprofits will call you back and answer your questions if you reach out.

You talk about giving effectively. The CEP also talks about giving strategically. So what does that look like for individual donors?

I’ll use myself as an example. I think that when I first started giving—when I graduated from college and had my own income—I was really excited to be able to give. And I just wrote a bunch of really tiny checks to a lot of small nonprofits. I didn’t really have much of a strategy or a thought behind it. If someone asked me, I would be responsive. And I think that there’s a lot of power in that too.

But I think that, particularly for larger donors, it really does make a difference to sit down and write down: What do I hope will happen with my giving? What would I like to be contributing to? Having that strategy can help bring to light, “Here are the folks I should be talking to. This is my lane, not some other lane.” Because you could get pulled in infinite directions with so many causes—there’s so much need in the world. Strategy really is combining some of your resources and giving in a deeper way, rather than just spreading it around.

Another thing that people are probably thinking about when it comes to giving strategically is how they can get a tax deduction for their charitable giving. Something that I’ve been thinking about a lot is that since the Tax Cuts and Jobs Act of 2017, deducting your charitable contributions might actually be less appealing. That’s because the TCJA greatly increased the standard deduction. To deduct charitable contributions, you have to itemize your deductions.

For an individual, what this really means is that if you don’t have itemized deductions totaling more than $14,600 in 2024 — the amount of the standard deduction — it’s probably not worth it to itemize. But, of course, it doesn’t mean you shouldn’t give charitably. Grace, I’m not sure if this is something that CEP looks into, but I’m wondering if you have noticed a change in how people have donated since the TCJA was passed?

I don’t have specific data on that. My sense is that what you’re alluding to is that individual giving did go down for donors who are giving smaller amounts. I think that for donors who already were giving a large proportion of their incomes or wealth, itemizing still continues. Especially with COVID, we saw just tremendous needs in our community. There’s a challenge for those of us who might be giving on the cusp of that $14,000 mark to really not be swayed by that. We should aim to be as generous as we can because it really does make a difference in the areas that we care about.

Right. And a tax deduction probably should not be the main reason that you’re giving to charity.

Exactly. We’re one of the only countries in the world that offers that.

Tax deductions aside, Americans are a very charitably minded bunch of people. In 2023, individuals in the U.S. gave over $370 billion. That’s according to Giving USA. At the same time, it can be really hard to vet the sources that you’re giving to. I’m thinking of all those GoFundMes that we see after myriad crises that pop up to support maybe an individual family or one person who’s having trouble making rent. How can we balance giving to urgent causes but ensuring that we’re not giving to somebody who isn’t exactly what they seem?

With GoFundMes, I really do think a good rule of thumb is: Do I know this person? Is there a level of trust? Trust really is the theme across both informal giving networks like GoFundMe, as well as giving to nonprofits. No one is saying you should go out and give to an untried and untested organization or someone you don’t know, or an organization you’re unfamiliar with. We do say, do your homework. Definitely ask for the information, ask the good questions, and then give as generously as you can. That trust piece really undergirds all of it.

And I think that can be part of someone’s individual strategy of giving. I’m thinking about my own strategy, as it were, where I have regular monthly contributions to organizations. Then I see all of these posts on social media feeds from artists and people that I follow saying, “Hey, this person needs $200 to cover their groceries,” or, “Here’s this family that was displaced by the war. Can you please provide something?”

In a sense, I’m relying on my parasocial trust of this celebrity as a proxy for trust of this GoFundMe being real. I feel so torn over giving because I want to help people and I do donate to these groups. But as it fits into my strategy, it’s a much smaller portion than my overall strategic giving.

Maybe you set aside a small amount to do that. That itself could be a whole strategy — where it’s like, “I would like to give to disasters in other places.” For me, and I think for many people, having a relationship with the communities and the causes that you care about can be a really important part of being an effective donor. So I would say maybe also give in a way that really connects you to your own community and causes that are close to your heart.

Yeah. An example of that might be maybe there is a nonprofit in your city that helps people who are displaced by a war that you are hoping to help someone through as well, so that way you’re connecting your ideal and your local community.

CEP also suggests that people reflect on their giving after the fact. You call it assessment and learning. Can you talk about what that looks like in practice?

Yeah. I mean, this is geared a little bit more towards large institutional funders. Funders who are giving large amounts of money into different communities or nonprofits — it’s actually really important that they listen well to what those folks need. I think this is somewhat true also for smaller donors. Sometimes donors have a really clear idea of what they want to do, but there might be a disconnect between what they want to do and what is actually needed.

Getting that feedback, and what’s so tricky about it is that communities and causes recognize that there’s a power dynamic. You’re the one with the money, and so they don’t want to jeopardize the funding. It might be really hard to say, “Actually, what you’re doing is not really what we need.” Being the kind of donor who can be approached and trusted to listen — again, that trust we talked about earlier—to say, “Actually, I know you want to do this, but can I also share about this need with you?” And really learning and expanding your view of what is needed and what communities say is most important to them is a really key part of the journey.

That means so much because I think people really have good intentions, but you also get it stuck in your mind, “Hey, this is what this other person needs, so this is what I’m going to do.”

And it can be really hard to hear them say, “I see that you want to help me, and I’m going to tell you exactly how you can help me.”

It’s really important to listen to that and give the help that’s actually needed, because sometimes help can end up being a burden on a community.

Exactly. And I think the root of this is often that we see financial wealth as being the sum total of wealth generally. Actually, there are many dimensions of wealth. Poor communities, communities on the margins—they actually have a lot of wealth and assets, perhaps that are non-financial, that we with the funds may lack.

We have to have a deep measure of humility when we go into communities or causes that we are somewhat distanced from and to say, “Actually, I have a lot to learn. I have money to give, but maybe I have something to gain too from the way they live their lives, what’s important to them.” It really is like a mutual exchange and not just a one-way thing.

Giving to a charity can be a very personal experience because maybe you’re giving to a cause that supports people who were displaced during a natural disaster in your home state, or it supports people who are affected by a specific illness that you have a loved one who also has that illness. There are certain causes that touch your heart in a very specific way.

That’s right. It’s very powerful.

Can you think of any stories where individuals or families have been able to use charitable giving to make a real impact on a cause that they care deeply about?

This is really the day-to-day experience of donors. I have a family member that has a rare genetic disease, and the only way that there’s going to be treatment for that disease is that all the families have banded together to basically fund the research that it will take to bring about a cure. That is true for any range of common diseases as well as rare ones. That’s just one small piece of it.

In every community in the United States, there are community foundations. These are places where donors can come together and say, “Hey, actually, here are some of the needs in our community. How can we band together and address them?” That’s a really powerful place for folks who might want to look into what’s going on with other people in their community. How can I join others? They should really look into that because in business, you want to keep your business strategy to yourself because it’s a competitive dynamic.

In giving, you actually want to do the reverse. If you’re just doing it in a silo, you’re probably not being very effective. You want to go out and see, what are other people doing? Who can I join? What’s my lane? I would really encourage donors to consider that.

Donating to important causes gets a lot of attention around the holidays, but whatever organization or cause people want to support probably needs that same financial support throughout the whole year. How can people take these generous intentions that they may be feeling right now and make them more sustainable long-term beyond just the holidays?

It’s so funny because this is an area that I’m actually personally trying to challenge myself with right now — and this is my job. I have always waited until the end of the year to do my giving, and partially that’s driven by tax reasons, but really it’s also, there’s no real reason why that’s true.

Maybe some of us, we have bonuses at the end of the year, that kind of thing. You’re right, nonprofits are so reliant on that end of December, at least in the United States, kind of giving that it really is feast or famine compared to the rest of the year. One of the things I’m trying to do is actually challenge myself not to wait until December. And you may want to talk to nonprofits that you support because sometimes around Giving Tuesday, they have matches or they have other interesting fundraising dynamics that might make your dollar go further. If you actually just email the nonprofit and say, “Hey, I don’t want to wait. Do you have anything like that now?” I guarantee you they will tell you what’s open and available to you. They will welcome the earlier gift. Oftentimes, I make that gift in the very last few days of the year, but then the check doesn’t arrive until the next year, that kind of thing. So it’s like, why do I do this to myself? I personally am also trying to just do it way earlier.

What I’m thinking of is, at NerdWallet, we talk a lot in terms of a savings strategy. We say it’s helpful to pay yourself first, where you have deposits go into your savings account first. I try to practice that with giving to charities first, where I have these auto payments go out on a monthly basis to some organizations that I care about. And making it something that is part of your monthly regular budget and can be anticipated just makes it so you don’t even have to think about it, but you know that in the background you are supporting the cause that you care about.

That is so important to nonprofits. That kind of ongoing operational support is really key.

Grace, I’m wondering if you have any other thoughts for individuals as they’re thinking about how they can maximize their charitable contributions.

I think that in the beginning, it’s actually somewhat challenging to get started. Maybe a lot of the listeners that you have are actually already giving in really thoughtful ways. I find that sometimes the real transformation of a donor actually happens after they start to give. It really is such a journey — and I hate that word because it’s so trite — but it is a journey. It is so different than being in business or medicine or law or any other field. That part of you that’s a donor, there’s a whole set of skills and a whole set of blessings, actually, of just really cool things that can happen. Making space and recognizing that it is a journey and seeking to learn is really powerful and actually will make your money go much, much farther.

All great lessons to learn at this time of year and any time of year, as we’ve discussed. Make it a year-round thing.

Grace Nicolette, Vice President at the Center for Effective Philanthropy, thank you so much for joining us on Smart Money.

Thanks so much for having me.

That’s all we have for this episode. Remember, listener, that we are here to answer your money questions, so turn to the Nerds and call or text us your questions at 901-730-6373. That’s 901-730-NERD. You can also email us at [email protected]. Visit nerdwallet.com/podcast for more info on this episode. And remember, you can follow the show on your favorite podcast app, including Spotify, Apple Podcasts, and iHeartRadio, to automatically download new episodes.

And here’s our brief disclaimer. We are not financial or investment advisors. This nerdy info is provided for general educational and entertainment purposes and may not apply to your specific circumstances.