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Money Dates & Couple Goals

Listen to this series via our Date Smart podcast. Episodes are released weekly!

I believe mastering love and money are the most intricate and enriching part of our lives. And with anything that’s highly rewarding, it takes time, energy, and effort to reach mastery. So, how can we continue to expand our money minds, navigate money talks with our partners, and master the game of love and money? It begins with creating the time and space to have conversations. So, today we are talking all about “money dates.” As we evolve, our money mindset should also evolve, and we should have a space to discuss what has changed in our world. Taking it one step further — having joint money goals is a great way for both partners to work together as a team toward achieving a dream. It keeps you both motivated and inspired. It gives you both a WHY. Why do you want to save your money? What do you want out of life? In the book, Eight Dates, John & Julie Gottman suggest going to a five-star hotel lobby to have your money date or any place that makes you feel wealthy or rich in some way, however you define those things. Here are some questions you might explore on your money date:

  1. Has anything changed in your money psychology? Share anything that has shifted your mindset (maybe a new book or podcast gave you a new insight you’d like to share).
  2. Look at the numbers (debt, savings, investments, expenses). Are you on track to hit your personal money goals? Are you on track to achieve your joint money goals as a couple?
  3. Create exciting and inspiring money goals together. Make sure to end your conversation on a high note. What money goal are you working toward that lights you both up? Are you planning a month-long trip to Italy? Have fun dreaming a little bit and getting on the same page about how you’ll use some of your money for “fun and adventure.”

Bonus assignment: Read chapter six from John & Julie Gottman’s book Eight Dates titled “Play With Me: Fun & Adventure” to see how important it is to plan for fun and adventure in your relationship. My favorite quote from this chapter is, “When our lives are infused with play, we’re able to see the absurd in the serious and find excitement in the mundane. A relationship without play is a relationship without humor, without flirting, without games, and without fantasy.” It goes on to say that different people have different ideas of what fun and adventure entail. For example, authors John & Julie Gottman say this about their relationship, “The issue comes when two partners get this brain-prize (dopamine) in different ways. Julie can’t sit on the couch and read books on physics and satisfy the seeking system of her brain. John can. John’s brain (the brain of a man who can easily think of ten ways you can die at a picnic) will not get the same rush of pleasure that Julie gets from skiing at breakneck speeds down a mountain.” “In the end,” John continues, “I had to face the fact that this woman, the love of my life, is very different from me. She is an athlete, an explorer, and a true adventurer. Adventure for me is studying quantum mechanics and differential equations from the safety of my chair. We created a new shared experience that has helped us remain in love year after year of marriage.”

So, think about what you both want and what constitutes an enriching, fulfilling life for the both of you, and create money goals to help you move toward your dreams. Because, at the end of the day, why are we saving our money after all? When Diego and I sat down to have this conversation, we both realized we wanted similar things. When we envisioned our perfect future, we both saw a life full of nature, sports, and community. We want to live on a farm and grow our food. I want to travel around the world for tennis tournaments, and he wants to train for cycling competitions. We both want a group of friends and family that bring us joy and peace. We want a beautiful home to host dinner parties. We want the freedom to travel for 3-4 months every year. To us, money means freedom. It means not having to worry about money and working on things that interest and inspire us. This is precisely why we created a joint money goal of reaching 1 million dollars in investments which will allow us to be “financially independent” meaning our investments produce a bigger return than our expenses so we never have to work again if we don't want to.

What kind of life do you want to create?

Interview with Rebel Finance School Founders Alan & Katie Donegan

Taylor (00:00):

Do you both have joint financial goals? And if so, what are they?

Katie (00:05):

Not necessarily in finances anymore, but we have things that we work on together.

Alan (00:11):

We have the Rebel Finance School where we give away courses that we run together, teaching people this stuff. So we have a goal to run one of those a year and we've helped a couple of thousand people sort their finances out. And we have goals to travel to places and do things. And every now and again, I have a goal of, I want to go to Disney for my birthday and stuff like that. Now we do a lot more goal setting together but that's been an evolution over the years.

Taylor (00:42):

Talk about the evolution. How did it start? Did it start with the financial independence conversation and having that joint goal?

Alan (00:49):

So it started with my obsession with goals, which came from self-development, which says you should have goals. So I would set goals. I would never meet them. I'd feel utterly demotivated. I would lose a couple of weeks to being depressed and just didn't want to make progress. And I had this love, hate relationship with goals that they'd inspire, but when I didn't hit them, I would be depressed. And that's because you set a timeframe of when you're going to do them and if you don't hit them, it's a very binary success or not. Whereas something like financial independence is a long, long goal. So it was less like it has to be done. Now we just need to chip away at it and do little bits and steps. And then eventually we started talking about different goals. And we started to set things together and like Steven Covey's book talks about you can't build something you haven't first seen. So you need to, he calls it, start with the end in mind. So first visualize where you're going and then set the steps to get there. And so we started to do that and talk about goals. And I started to learn, that it's not just a one-and-done, you don't set them and then forget about them. It's something you do every day. And there's been a long journey of learning about goals, and how they operate. And I think they can put a lot of people off. And if you get it wrong, it can actually damage where you are going and set you back. But if you change your mindset, they can be incredibly motivational over the long term.

Katie (02:21):

I think that all or nothing mindset hurt you a lot. Didn't it? Because say you had a goal to run 20 miles and you'd never run before in your life. And that one time you run 19 and a half miles. Oh, are you a failure? Because you didn't hit your goal like that all-or-nothing thing.

Alan (02:41):

Yeah. My goal was to make $100,000 in a year.

Katie (02:44):

So if you made $95,000 then you're a failure. If you start and maybe what, the year you set that goal, you were making $30,000 and you're like, I'm gonna stretch that goal. I'm gonna go for a hundred and you do 95. So you've tripled it.

Alan (02:58):

But I didn't, I would go from $30,000 to $35,000 or whatever, and then feel utterly depressed that I was nowhere near it. And it completely destroyed me at that point. And that's the thing about thinking in decades, not years, everyone overestimates what they can do in a year and they underestimate what they can do in a decade. So stop thinking in years and set the big goal for way out and then improve every day on the way towards it. And you'll get there eventually.

Taylor (03:27):

How did you guys work towards these goals together? Did you have weekly meetings, or monthly meetings? Did you have milestones? How did you work towards these goals together?

Katie (03:37):

For the finances? One, we would have monthly check-ins.

Alan (03:41):

We had monthly finance meetings, and constant discussions. What we're going to do. We got fully inspired by that one. And that one took over for a long time and we got very outsized results in that area because of our focus on that one area.

Taylor (03:55):

Financial independence for five or so years? 

Alan (3:58):


Taylor (3:60):

What did those conversations look like? I'm so curious about the details, like what did those conversations look like? Like, give me an example of what you guys would talk about.

Katie (04:08):

We have a process that we follow that comes from Jim Rohn, who’s one of the original self-development OGs. And he has a process that you go through where you start by saying, what's five things you've done recently that you're proud of to get you in the right mindset of feeling positive and like, oh, I can do stuff. Look, I've already done these five things.

Alan (04:36):

Write 50 plus goals. Who do you want to meet? Where do you want to go? What do you want to have in your life? Do you want a new fridge? <Laugh> Do you, whatever it is, write 50 plus goals and volume is important. Then you pick your top four one-year goals. And then those one-year goals, you write out a paragraph of why they are important. And then the final piece is the question, who do I have to become to achieve those goals? And that's a really fascinating question because then you say, okay, I want to grow my business and sell this much money. Well, who do I have to become to do that? I have to become a great salesperson. Okay. So now my task is to learn how to sell, to develop my skills as a business person. Then you have the process to get to the goal. Whereas I think quite often we set the goal and think about it, decide some random action that we take and it never gets you towards it.  So that kind of process of goal setting happened.

Katie (05:37):

We look back over those goals that we set over the years and invariably, even the ones that we didn't focus on, you'll read through and be like, yeah, done that, done that, done that, done that. So that thing about thinking in decades rather than years, yes. You were frustrated after only a year that you hadn't made enough progress but you look back 10 years ago and you're like, blimey, I’ve done all of those.

Taylor (06:02):


Alan (06:03):

And then what did the conversations actually look like? We actually found that walking together was one of the best ways. So imagine a scene where we’re in Basingstoke in Hampshire.

Katie (06:14):

Most people wouldn't be able to imagine that.

Alan (06:16):

It's gray. It's cold. It's England, it's raining.

Katie (06:22):

Google the Wote Street Willy.

Alan (06:25):

We had this same loop around Basingstoke that was like a half an hour walk. And being next to each other chatting so you're not just face to face. Like there's something about that being next to each other, walking, talking, coming up with the ideas that was where a huge amount of the conversation actually happened.

Taylor (06:49):

I love that because whenever we go face to face, I feel like there's an unnecessary tension there. And we've had our biggest conversations either in the car or walking on the beach. Yeah. I remember I don't know why this pops into my head, but the weekend that we went to San Pancho, a little nearby beach town and we had done the 50 questions to fall in love, that one quiz that went viral, or the 36 questions to fall in love I think it was. And we decided to do it in the car ride up to San Pancho and it took the entire car ride. And then we continued the conversation during dinner and then whenever we finished the questions he ended up proposing right afterward. So I thought it was really funny timing that we did the 36 questions to fall in love and then he proposed afterward.

Alan (07:47):

Do you think it was premeditated?

Taylor (07:50):

I found the ring a year, no two years before he actually proposed. He doesn't know that I found the ring in his backpack when I was cleaning and so yeah, he had been thinking about it for a while.

Alan (08:03):

He had been thinking about it for a while. Just looking for the right moment.

Taylor (08:06):

Yeah. Yeah.

Katie (08:08):

I think the beauty of when you are walking or in the car is, silence is okay if you're walking, it’s like, oh, we’re walking so it's not weird if you're not saying anything.

Taylor (08:19):

Oh, that's true.

Katie (08:20):

So you got the time to process rather than just like looking at each other.

Alan (08:24):

Like, “Are you going to reply?”

Taylor (08:25):

<Laugh> Do you guys have joint finances?

Katie (08:30):

I mean, we don't have any joint accounts or things aren't in both of our names. It's either in one name or the other, but we think of it in aggregate. So it's all of ours.

Alan (08:44):

But one important part of any relationship is both people should have access to some of their own money. You should never have to go to someone else and say, please give me money for something. You need to have a way so that you both have some independence financially, as well as the joint working on it and the joint goals.

Taylor (09:03):

Because people assume they need to join accounts or join finances when they get married. But that's not a reason in itself. You have to have a reason to want to join your finances.

Katie (09:18):

We just always had separate but thought of it as together. So Alan would pay for holidays and fun stuff and I paid the mortgage and the electricity bills. And actually, it came out about the same anyway.

Taylor (09:34):

Oh, I like that. That makes it really easy. Yeah. You don't have to worry about, okay, now it's February, we're going to pay half and half.

Alan (09:44):

Yeah. We never had that. We both had incomes.

Katie (09:51):

Well, when you were self-employed, your (income) was more erratic.

Alan (09:55):

So some months I would do really well, some months I wouldn't. And it wasn't until later on in my career that my business was growing, that I was bringing in money regularly. It was very on and off to start with.

Taylor (10:05):

Yep. Makes sense. Making financial decisions in the relationship. I know you mentioned, that you want both of you to create the decisions together. It's like a 50/50 contribution to the relationship. You gave the example of how you guys have your separate accounts and then you handle the mortgage and you handle the vacations. Can you give any more examples of how you shared finances and how you guys came to that conclusion?

Alan (10:30):

I think how we came to the conclusion. I think it started from that very first bit where right at the start, Katie was at university and I was earning money and I always said, it will go the other way. Like I will pay for food now, but at some point, it will go the other way and it did. And then it went the other way and I was making more money and Katie wasn't and then it went the other way. And so those experiences always led to it doesn't really matter whose it is. It's ours. It doesn't matter which account it's in. It's ours.

Katie (11:05):

Yeah. I don't remember ever sitting down and being like, okay, I'll pay XYZ. And you do ABC. It kind of evolved naturally.

Alan (11:14):

And then I guess the big bit in terms of investments, most of the time it's whose name is most tax-advantaged to put this in, and tax drives a lot of decisions and reasons. And it's like, okay, you've got a certain capital gains allowance. I've got a certain capital gains allowance. We've got certain tax allowances and that drives a lot of our decisions is what's the most tax-efficient route.

Katie (11:44):

It's more like a game to play together.

Alan (11:48):

It's a game to play together to win the system.

Taylor (11:50):

<Evil laugh> Love it. What do your guys' meetings look like today? What do your money meetings look like today?

Alan (12:00):

We have a monthly finance meeting that we do together, which is one of the most exciting times of the month.

Katie (12:04):

We get very excited. I'll say, Alan, do you know what it is tomorrow? It’s our monthly finance meeting. 

Taylor (12:10):

I love this. Tell me more.

Alan (12:14):

It normally involves a nice breakfast out.

Katie (12:17):

The last working day of the month. We have a net worth spreadsheet, which lists out everything that we have.

Alan (12:26):

Yeah. Assets and liabilities.

Katie (12:28):

All assets and liabilities. And we update it to say how much we have.

Alan (12:32):

And then are we going in the right direction? Or are we not going in the right direction? And what happens? And then we have a good discussion of like, what did we spend? Where did it go? What was a good investment of money? What was a waste of money? What would we spend more on?

Katie (12:46):

When you say good investment, you mean our spending. So we look at two things, we look at how much we have, a snapshot, and then more the cash flow. So what did we spend this month? And that's what you mean when you say, was it a good investment? Did we get value for our money? What was a waste of money?

Alan (13:04):

Well, we're in our Airbnb at the moment and we paid a lot more for an Airbnb on the beach, but what a wonderful use of our financial resources. Because we can roll out onto the beach, go running, go swimming. It's amazing. And that's been in our discussion: spend more on the stuff that we value. And sometimes you spend money like we go out for a fancy meal and it wasn't that good and you're like, okay. It just felt a bit awkward. There were too many people around you. It was a bit weird.

Katie (13:35):

Let’s just go to the taco stand next time. <Laugh>

Alan (13:38):

And like that didn't represent value for money. So let's not do that. Let's do that instead. Mm. So we kind of have a look at that. Like where could we spend more to have more happiness and where are we spending too much that does not bring happiness?

Taylor (13:53):

That's really, that's really great. I haven't thought about doing that exercise with Diego.

Alan (13:59):

Where's your money going? And is it bringing you happiness?

Katie (14:02):

Is it in line with your values? So Alan and I love having a really nice place to live. The environment that we are in is very important to us and we enjoy food and we enjoy eating out.

Alan (14:14):


Katie (14:15):

Not necessarily fancy stuff. We just like really good food. Good quality, high quality, but not super pricey, super fancy. And then on the flip side, we don't spend money on jewelry and clothes.

Alan (14:31):

Because that's not what we value.

Katie (14:32):

I've never been into makeup. Like we don't value it so we don't spend any money on it. And I think it's knowing what is important to you and spending your money accordingly.

Alan (14:42):

And if clothes are important and you value them, then spend your money on that, don't spend it on a car, just spend it on what's important to you. But sometimes I think people spend to keep up with the Joneses and to keep up appearances, whatever, and they don't actually get the joy.

Taylor (14:57):

I’m going to steal this exercise though. I mean, we both have an idea of what we value and what we would like to spend money on. I love having a nice environment. So my house is really important to me. Diego could live anywhere and be happy. I'm jealous of him. He's very happy with whatever he has, which is an amazing quality. But trying to get him to understand, I need to have, you know, aesthetics is important to me. I need to feel like I'm in a nice environment, in a nice home. So I can feel good. I feel inspired. I feel safe. I feel all of these things that I feel when I'm in a good environment. And so, yeah, and I try to get him to be like, Hey, what do you value? What would you like to splurge money on? He can't think of anything! He’s such a practical guy. He's like, I don't feel the need to splurge on anything. (And I’m like) But give me one thing, I feel like I'm like pestering him like just give me something! He’s like, okay, a bike. I’ll spend money on a nice bike. He loves cycling. Cycling is his life. He's so passionate about it. But I love this exercise. Like what do you value together? What did you spend too much money on this month? What can you spend more money on next month that you both really value? I love that. Thank you.

Katie (16:17):

We can send you a list of questions that we ask ourselves each month.

Taylor (16:20):

Please. Yes.

Alan (16:22):

It's part of our financial meeting each month we ask ourselves a set of questions and yeah. Questions are the key.

Taylor (16:30):

How many questions are there?

Alan (16:32):

Like four or five for the end-of-month meeting.

Taylor (16:34):

What are they? Can you tell me now? Let's get into the nets and bolts.

Katie (16:44):

What went well this month? What did we spend a lot on? What really added value to our lives? What was a waste of money? Where could we spend some more money?

Alan (17:00):

And the final comment is where is our money invested? How much have we got in equity, property, and cash?

Taylor (17:08):

Love it. Do you guys have any bullet points or questions from previous conversations? Like a long time ago? I'm just curious.

Alan (17:18):

It'd be in the old notebook.

Katie (17:19):

When did we start doing this?

Alan (17:22):

A long time ago? Did we have a monthly finance meeting?

Katie (17:25):

Did we jot down those answers? I don't remember doing it.

Alan (17:29):

I've got January 2020. It's not that long ago, but like two and a bit years ago. Mm yeah. What went well, we rented out our flat. Yay. We turned it into an asset. We're diligently tracking our expenses. We were very happy about that. Yeah. What do we spend a lot on, we booked all accommodation and transport for the next few months, we spent on travel insurance for the year. What really added value to our lives? You loved pole dancing. It says good spending of money.

Taylor (18:02):

It's a great workout.

Alan (18:04):

Alan enjoyed coffee out and working on his laptop.

Katie (18:08):

Each to their own.

Taylor (18:09):


Alan (18:13):

We bought some tickets to an event that we didn't end up going to. So like, that's a huge waste of money. Where could we spend more, accommodation and massages were our two comments.

Taylor (18:27):

I like that.

Katie (18:29):

We were in Thailand for context.

Alan (18:31):

And then our split was 3% cash, 22% property, and 75% equity. That was where our money was at that time. And you reflect on your total net worth and all of that jazz. Where's your money going?

Taylor (18:48):

Yeah. Perfect. Thank you for sharing. 

Alan (18:50):

Some random things for you and insight into our lives that you never knew you wanted.

Taylor (19:00):

But I love hearing this and seeing this and having you guys talk about it because Diego thinks I'm really weird that I have all these questions written down and that I want us to have financial monthly meetings and he thinks it's too much, you know, he's like, just let things happen naturally. Come on <laugh> and I'm like, but I want to plan our entire lives right now!

Katie (19:20):

I mean, it is weird in the sense that it's unusual. Like no one does this, but then that's why the people that do focus on it have the results that they have because they're building that and they're focusing on it. So yeah, it is weird, but embrace the weirdness.

Taylor (19:36):

Embrace the weirdness. I like that.

Alan (19:39):

The thing I would say to Diego and to everyone listening to this is extraordinary doesn't just happen. You don't drift into it. You have to build it. And if you're not consciously creating your life, you will just drift through it. And you can be happy doing that. And that's fine if that's your choice. We wanted to build something else. We wanted to build our version of what an extraordinary life is. And I think for everyone listening, I would say, figure out what extraordinary means to you and then go after it.

Taylor (20:10):

I love that.

Katie (20:11):

And it doesn't have to be big and grand and crazy.

Alan (20:16):

It might just be dinner with the kids every night, that's extraordinary in this time.

Taylor (20:21):

Yeah, exactly. Figuring out what is extraordinary to you. And that goes back to doing these monthly questions. What do you value? Right. Such an important question. My final two questions for you guys. When, in your personal opinion, should people start talking about money? When should people in their dating journey start talking about money in their relationship with their person?

Alan (20:48):

I feel like it would come up on the first date with who's paying for the meal or who's paying for the, whatever. It always get a little bit awkward and weird.

Katie (20:56):

I was going to say, maybe not the first date, but you're right. That can prompt a little bit of weirdness. 

Alan (21:05):

I don't think you want to go full in with that conversation in the first three or four dates. Like, let's get to know each other, but it's interesting. Like, oh, what do you feel about this? What do you think about this? Ask questions. I think it's fascinating and getting a little bit deeper with the person opposite you, it’s really interesting to actually understand them. So start easing it in.

Taylor (21:30):

And it doesn't even have to be questions like how much money do you make. It can be, did your family talk about money when you were growing up? Right. Or some sort of non-invasive question about their past.

Katie (21:41):

Which they can choose to answer in as much depth as they want to. Like, no, they didn't really talk about money, and then maybe they shut the conversation down, which is a sign. Well, it's a sign, but also it's like, I'm not ready to open up about that yet.

Taylor (21:55):

It's a good point. You can tell a lot by what a person says or doesn't say and their body language, right? Like if they tense up right away.

Alan (22:07):

And how they react when the bill comes and the tip and all sorts of different things around booking tickets for the cinema for your third date, like, is it up to you to pay? Do they even offer? Is it a discussion? It's interesting. You can notice a lot about these things.

Taylor (22:27):

And I feel like we're in an interesting time now just because it's changing quite a bit gender roles. As it should. I have a lot of friends that are still very old-fashioned and they say, I want the guy to pay for me maybe the first two dates and on the third date, I'll start contributing, but I want them to pick up the bill the first two dates because I feel like they are making a gesture or I feel like they're showing me that they care about me. I have some friends like that still. And then I have friends that are like, I'm insulted when they pick up the bill for me, like the opposite end of the spectrum.

Alan (23:03):

It's dangerous. There's no right answer for us anymore. And you don't know what's going to happen. It’s like, so the bill has come, how do you feel about this? Which one of us, are we both going half? Would you like me to pay? I'd love to. I don’t know. It’s challenging.

Katie (23:22):

It's a minefield.

Alan (23:23):

It is. I don't want to step on the landmine.

Taylor (23:26):

It's so true. We're in an awkward phase but I like that, just bringing it up. That's a great conversation starter. Like what do you think about who should pick up the bill? Just bringing up the conversation, right? And do you have any advice for partners, on how they can start having these conversations around money, especially if one partner is reluctant?

Katie (23:49):

I think, what did your parents teach you about money is a really nice way to ease into it. Because it's exploratory, it's not accusatory. And the other one is, to start talking about what you want to build together. You need that big why before you start going into the nitty gritty of like, well, how much do you have in this account and this account? And people can feel very interrogated.

Taylor (24:20):

I love that. Yeah. That's exactly what we did. So Diego and I started asking those questions about our family and money psychology. And now we're in the, what kind of life do we want to create together phase. And I have this huge list of questions that I had to translate into Spanish first and then I sent it to Diego and I said, why don't we write a vision statement? That sounds so formal, but like, a vision statement of what we want our family to look like in five or ten years. And, here are some prompts like some questions and we can come together and we can share those with each other and see.

Alan (25:00):

That's one of the most insightful exercises. We did that when we were heading towards financial independence, we did an exercise where we both created a PowerPoint. We sound like such corporate geeks.

Katie (25:13):

That's how we communicate.

Alan (25:14):

That's how we communicate. We created a PowerPoint each of what do we want life to be like in financial independence. And then we shared it and commented on it. I used a lot of pictures. It was beautiful. <Laugh>

Katie (25:26):

Implying that I didn't use a lot of pictures.

Taylor (25:29):


Alan (25:30):

And we talked about it afterward and it's because I think there's always one more of a verbose partner and that's challenging because then you're trying to pull answers out of the other person, whereas you need to give them the time to write and create and think, then you can swap and comment and it'll inspire conversations. So I love that you did that. We did exactly the same thing and we do it actually every year. We have an annual set of questions that we talk about, what went well, where are we going with life?

Katie (26:01):

I think it's important, like you said, to answer the questions separately and then come together, because like you said, the danger in our relationship would be Alan would go, oh let's do this, this and this. And I’d go, oh, that sounds fun. Okay. And then I haven't had a chance to input or take the time to think about it and I can be a bit lazy and be like, okay, yeah, you've come up with something cool. Let's just do what you said.

Alan (26:24):

And that leads to resentment in the future if you're not careful.

Taylor (26:28):

The first time you guys did this exercise, was there anything that came to light that was like, oh wow, we're both on the same page or we're not on the same page with this or what did that first exercise look like?

Alan (26:42):

Well, I think I wanted to go and write a movie and Katie wanted to cycle around the world type stuff and we had different things. But that's good to know. And then you can do a bit of this and then we do a bit of that and I wrote the movie first and then we went to New Orleans for music for Katie later. And I think it's good that you find out these things because then you go, okay, that's your dream. I want to help make your dream real because I know that will make you happy, which will make us both happy. And it's not a binary outcome where one of you gets to do what you want and the other one doesn’t. There is a way to fit it all in to create the life of your dreams together. But we did have those like, oh, you want to do that? I want to do this. How does that fit together? And it doesn't have to, you can do them one after the other.

Taylor (27:33):

Yeah. Yeah. We haven't done the exercise yet. I just sent him the questions. So we're going to convene next week.

Katie (27:41):

Report back.

Alan (27:41):

Are you going to record it for everyone listening?

Taylor (27:43):

I want to, yeah. <Laugh> I told him I'm like, do you mind if I record and we'll probably do it in Spanish, but I was thinking, how can I do like a translation over us speaking in Spanish? I haven't figured out the details yet, but yeah. I want to record. I'm just looking at all the questions I have. It's going to take a while but yeah, that'll be fun. I promise last question. Did you guys talk about, do you guys want to have kids?

Alan (28:14):

No. We did talk about it.

Katie (28:16):

We both assumed that we would have kids because that's what you do.

Alan (28:20):

When we first met, I wanted a four-bed house and two kids. That was my goal way back when.

Katie (28:26):

Which we kind of just inherited from society and culture being like, that's what you do. And then slowly it occurred to us that we didn't want that. And we like the freedom that we have from not having kids.

Alan (28:44):

One of my friends made it his mission to show me what bringing up kids was actually like, changing diapers, telling me all the stories and he would always end the stories with, "and of course I love them and they're a massive joy in my life.”

Taylor (28:58):

The obligatory comment after each word vomit <laugh>.

Alan (29:03):

He definitely created an “away-from” motivation for me that I don't want kids.

Taylor (29:11):

I forget now the exact number, but the dollar amount of raising a kid until they're 18…

Alan (29:17):

It's like a quarter of a million.

Taylor (29:18):

A quarter of a million. Yeah.

Alan (29:20):

It's expensive.

Katie (29:22):

It would be cheaper in Mexico.

Alan (29:23):

It would be definitely cheaper in Mexico, but we decided we didn't want kids and we love our life and our freedom. And maybe that sounds selfish in a way, but I didn't care. I love my life. I love our life together. I love the way it is. I love that we get to travel and what we do and the freedom we get to create courses, and give them away. It's just incredible. And I'm sure we would be happy if we had kids, just a different type of life and you sometimes see our friends and they love their kids and they love their life, and they're also jealous of our lives.

Taylor (30:03):

At which point did you guys have the kid conversation, whether you wanted kids or not?

Alan (30:09):

I think we both assumed when we were first getting together that we would have kids. Yeah. And then it gradually shifted.

Katie (30:16):

I always just kept deferring it. So we got together when we were quite young and I was like, oh, you know, when I'm 30, then we'll start thinking about it. And I got to 30 and I was like, well, my brother had kids when he was 35. So 35 is my new deadline. And then we got to 35 and I was like, no.

Taylor (30:38):

We have similar stories.

Katie (30:39):

<Laugh> So you've decided not to have kids?

Taylor (30:41):

Well, it's funny because the same thing, whenever we got together, it was just five years ago. We both assumed that we would want kids. And I told him, you know, I think I will want kids when I'm 34, 35. I was what? 30 at the time? Yeah. I was 31. I'm 36 now. Sorry. I'm bad with math. 

Alan (31:04):


Taylor (31:04):

So anyway. Yeah, same story. We both assumed we wanted kids. And then, you know what?  I think it was a year ago or over a year ago, and I was reading Ramit Sethi's book, I Will Teach You To Be Rich, and at the very end, there's a whole chapter dedicated to how much it costs to raise a child. And I got done reading it and at that time I was 34, and I still didn't have that urge that I wanted to have kids and I turned to Diego and I just said, I don't think I want to have kids and he just said, okay. And I said, really? Okay? And he said, yeah, I think it's okay. And I go, I don't know. I think you want kids. And he said, yeah, but at the same time, they're really expensive.

Alan (31:58):


Taylor (31:59):

And the world, this is during the pandemic when it first hit and he was like, the world is just in shambles right now. I don't know if that's a good choice. And I said, okay, well, we’ll keep talking. Now I'm 36 and I still don't want children. I don't think I'm going to want children. And I'm just worried that he is going to want children. And so I want to keep having that conversation with him and seeing how important that is.

Alan (32:30):

We always said if like Katie goes past it and we want kids… that’s not what I meant.

Taylor (32:37):

Well, yeah when we hit a certain age our fertility declines. We're talking about freezing my eggs right now. So I get it.

Alan (32:42):

We could always adopt, we could always do something else. Like there are plenty of kids out there that need loving parents. There are ways to do it. And we've got nieces and nephews that we can go and hang out with and then return them afterward.

Katie (32:56):

They kind of fulfill our like parental needs, like that bond and connection but it's obviously not the same, but we get the joy from being around them.

Alan (33:07):

Yeah. And if we ever want to change our minds, we could adopt, we could do different things, we can settle down in a place. We can work it out. And I don't want to make a decision forever. I want to see how we feel and the way we felt for a long time is no and then we'll just see what happens.

Taylor (33:27):

Yeah. That's where we are. We've discussed adoption and freezing my eggs. So yeah, we’ll see what happens. But it's a big decision.

Katie (33:41):

And there's a deadline as well, which is different from other decisions. Like, well, we can always change our minds later. You don't have the same option if you want to have your own biological children.

Taylor (33:50):

Exactly. I mean, they are working on fertility technology, hopefully, in the next 10 years, that'll be a different story, but currently, yeah, there's a deadline.

Alan (34:02):

What a conversation.

Taylor (34:03):

What a conversation. Anything else you want to add before we wrap up? Where can people find you?

Alan (34:11):

So if they want to find us, I have a website called and we both write articles about financial independence. And we run our Rebel Finance School that we give away and I run the Rebel Business School. So just Google Alan Donegan, and you will find us and me and what we're up to and all of that stuff. And I have a podcast called The Rebel Entrepreneur.

Taylor (34:34):

Which is amazing. I binged it last year. 

Alan (34:38):

Thank you very much. It's all about how to start a debt-free businesses. And that's been my mission to help people make money for a long time. And I guess my closing thought for everyone listening to this is you can build any life you want to. I genuinely believe that any of you listening to this can build any life you want to. Don't just let it happen to you. Take control of it and build the life you actually want. Decide what is your version of extraordinary and then create it.

Taylor (35:15):

I love that, so important. People check out his blog, his podcast, their rebel business school, and rebel finance school. I will link to everything in the show notes. Where do you like to talk to people? Is it Instagram Facebook, the blog, or the newsletter?

Alan (35:32):

Face-to-face in a taco shop in Puerto Vallarta would always be good. <Laugh> but yeah, they can send us a message on the blog is a great place to find us.

Taylor (35:42):

Okay, cool. And they offer amazing courses on finance and entrepreneurship and yeah, all-around amazing people that I've become so close to here in Puerto Vallarta, Mexico. So thank you for taking the time. As always much appreciated.

Alan (36:00):

Thank you for inviting us on the podcast.

So, what kind of life do you want to create? Alan & Katie urge us to “start with the end in mind.” This means visualizing the life you want to have because you can’t build something you haven’t seen yet. So, first, visualize where you’re going and then set the steps to get there. Why do you want to save your money? What do you want out of life? Or in Alan’s words, “what is extraordinary to you?” Not what is extraordinary to your friends, or your family, or what society tells you, but what is extraordinary to YOU? Once you get clear on what you want, only then can you begin to consciously create your life. In Alan & Katie’s monthly finance meetings, they ask the following questions:

  • What went well this month? 
  • What did we spend a lot of money on? 
  • What really added value to our lives? 
  • What was a waste of money? 
  • Where could we spend some more money?
  • Where is our money invested?

I love the question, “What added value to our lives?” because this shows you how money can add value and joy to your life. Many of us spend money on random consumer goods or we spend money to keep up with the Joneses. However, few of us stop to consciously think about how we spend our money, and if our spending habits are bringing us joy and adding value to our lives. Spend time and think about what you really want. And if you’re in a relationship, talk about it with your partner. Alan & Katie created a vision statement for their lives, just as Diego and I are doing the same thing right now. And as Katie pointed out, yes it’s weird, and no, nobody does it, but embrace the weirdness. Be different. Be intentional. Be conscious of your decisions. Only then can you get the results you desire. And remember, you can build any life you want to.  

That is the end of season three, my dear friends. Next week I am releasing a bonus episode of the entire unedited conversation between myself and Alan & Katie Donegan if you want to check that out. Otherwise, we will be back in a few short months with season four. In the meantime, find us on IG, FB, and Twitter at ambiancematch and say hi. I love hearing from our listeners. You can also head to our website at and subscribe to our newsletter where we release blog posts and news of upcoming podcasts. Thanks!

Resources mentioned in the episode:

The 7 Habits of Highly Effective People by Stephen Covey

Listen to this series via the Date Smart podcast. Episodes are released weekly!

The Date Smart podcast is hosted by Ambiance Matchmaking’s cofounder Taylor Wade. Twenty years ago, Taylor cofounded Ambiance Matchmaking, an exclusive matchmaking agency that has helped over 100,000 singles master their dating lives. In this podcast, she shares the same tactics and techniques with you. Mastering your dating life is easier than you think –– it’s just a matter of science and a little know-how.

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Taylor Wade

Taylor is one of the founders of Ambiance Matchmaking. She now dedicates her time to curating content for our community through her podcast and blog. Writing and podcasting is the art of great story-telling. As a relationship writer and editor, she has always sought to capture the reality of the dating experience, full of drama, friction, and joy. The best mind is an open mind, so she specializes in asking questions and approaching a story without preconceptions.

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