Talking Money with Women in the Wind

We love talking about money with other people. No matter how unique we are, we can always learn something new about money and about life from other people. And just listening to others tell their money stories helps to support them in reaching their personal finance goals. We’ve gotten so much out of our money conversations that we decided to start an interview series with our personal finance community. Rather than focusing only on income and investing we’re very interested in the emotional side of personal finance. And we’re thrilled to share stories from some of our friends.

Everyone, meet our friends Star & Joyful Jetsetter! They’re 43 and 52 year old women living in Chicago, IL. They’re working their way towards FIRE and making all kinds of fun plans to change their lives. We are inspired by them and we hope you will also find something encouraging in their money stories…

1. What were your childhood money experiences? Did you learn useful money lessons from family?

Star: My parents were blue collar workers in Singapore, mom mostly worked part time. We had everything we needed, but just not a lot of extra money for non essentials. My dad is a great budgeter, my mom liked to spend on little luxuries for us 3 kids when she could, and still does. As kids, we learned not to waste food, and to take good care of our belongings so they would last longer. As an adult, I have had a few mis-steps financially but I take full responsibility for any bad money behaviors, because I have had better opportunities and education on money than my parents.

Joyful Jetsetter: My dad worked as an electrician and my mom was primarily a stay at home mom until my teens when she worked in an office to help fund college for my brother and I. My parents provided many excellent lessons on money. They both sacrificed a lot of things they wanted and needed to ensure we didn’t go without. They focused on experiences and doing things we enjoyed and prioritized their spending based on what was important to them. I’ve learned all of this and more from my parents, but the biggest lesson I should have paid attention to, and didn’t, was to save at least 10% of what I earned. My parents were FIRE before it was a thing and my Dad retired at 50.

2. What kinds of experiences have you had with debt?

Star: I did rack up some debt, partly because I put myself through university for my bachelor’s degree, then later graduate school, and also partly because I was young and was sucked into buying luxury brand name stuff. I took out some education loans, put what I could on credit cards, only made minimum payments on everything, and it took some years to clear off that debt. I am a totally changed person now, I have no debt other than a mortgage in Singapore. I’m renting my condo out so it pays for itself. But now, I value my time and don’t want to trade more work for more spending – a $50 watch tells me the same time as a $5,000 watch, you know what I mean? I prefer spending my money on experiences now rather than material things. Except if I ever adopt a puppy, I would most definitely spend like a rockstar on puppy toys!

Joyful Jetsetter: In college many of my friends got credit cards and my parents were firm that I didn’t need one. My parents only bought what they could afford and didn’t believe in credit. I remember many back-to-school shopping trips done on layaway at Kmart. But credit cards were frequently marketed to us on campus and they were very hard to resist. I got my first card at graduation and then the problems began. Eventually I would rack up $65K in debt across multiple cards. After paying off my balances I cancelled all of them and didn’t get another credit card until recently (after over 20 years). Now I use my card for all of my personal spending, racking up points to offset travel expenses, and paying it off monthly.

3. What’s your investing style?

Joyful Jetsetter: I leave the investing to Star. I also leave the joint budgeting to her and do whatever she recommends when it comes to how much money I need to put in whatever account. I trust her implicitly. When it comes to my personal spending, I’m still working on the notion of a budget. I will say even without a budget my spending has decreased dramatically and my savings rate has gone up as a result.

Star: On investing I’m all about low cost index funds – because it gives me more diversification for less fees which helps maximize my returns. I still have a lot to learn about investing. My investment fees are around 0.03% on average. I do not use an advisor, I self manage mine and my wife’s investments, and learnt all of this through books and blogs and 2 of my favorite books are The Simple Path to Wealth, and Quit Like a Millionaire

Most of my money is in a 401k which holds some target date funds, S&P 500 and Total Market Indexes. I max out my 401k contributions every year, but I don’t qualify for a Roth IRA.  

My taxable brokerage account is small but more varied because I figure I can live a little more dangerously here compared to my 401k. In my brokerage I have an S&P 500 Index, a Mid Cap Index, a Cannabis Index, a Bond Fund Index, a Technology CyberSecurity Index, and I also have a little Crypto. 

For our savings and checking, we essentially have 3 buckets – “ours,” “yours,” and “mine.” In the “Ours” bucket we have a joint emergency fund in a high yield savings account that can support us both for 1 year if we should both suddenly lose our jobs at the same time, which is highly unlikely. We plan to eventually grow this into 3 years worth of living expenses at retirement. We also have a joint checking for shared household expenses, and finally a shared sinking fund for travel, charity, or sending someone flowers to get well soon, that kind of thing. For the “Yours” and “Mine” buckets we are each free to spend or save what we want, but we do have a savings goal in mind each year to try and achieve.

4. Do the FIRE and financial independence concepts appeal to you?

Star: I can’t get enough of it! I wish I had known sooner, but better late than never. I don’t want to wait till I’m 72 to retire. I want the freedom now and I’m willing to work hard at saving more to get there. Now the focus is to grow our taxable brokerage account so we can actually be FI, in the next 10 years. FIRE definitely inspires me!

Joyful Jetsetter: I’m extremely attracted to the idea of retiring early. I always used to worry about money and now having things like an emergency fund and so much money in my savings account has really inspired me to incorporate more of the things Star asks me to do. It’s been hard, but it hasn’t limited me from doing the things I love to do nearly as much as I thought it would. Star has reinforced so much of what my parents taught me early on, but I was too stubborn to listen back then.

5. What kind of work for pay do you do? And what kind of unpaid work do you do?

Star: I’m a software Project Manager, I feel blessed to have a great job that pays well and a skillset that is mostly transferable to any company and role. But my goal is to retire a little earlier than normal, because I have many varied interests and life goals and I feel work gets in the way of achieving those goals. For example, I am learning electric guitar and my goal is to play with the biggest rock band on earth called Rockin’1000. They stage stadium concerts in Europe every year, and they welcome 1,000 rockers worldwide, anywhere from 9 to 90 years old to perform in the band 🙂 I can picture myself at 90 rocking it out there, but hopefully that dream comes sooner than 90.

Joyful Jetsetter: I’ve been in technology for 30 years with increasingly demanding roles over the last decade. Work stress has become a major contributor to my increasingly poor health and I was diagnosed with an autoimmune disease in 2015. I recently quit my job because it was making me sick. Since then I’ve started independent consulting and realize I can make the same money working 30 hours that I used to when I put in 60-80 as a salaried executive. My goal is to work as little as possible while making as much as I can so that I can have the best life with Star.

Our Unpaid Work : Pre-pandemic, we both volunteered biweekly at Chicago’s LGBTQ center as “IT Help” for the seniors. They come to us about anything tech related, from how to use their phones, how to open a Facebook account, how to retrieve photos from a USB stick. We met many interesting seniors this way. I think once we’re retired we’ll find some way to either work part time or volunteer our time to keep busy with meaningful pursuits like this. We don’t quite know what it will look like yet, but that’s ok and we’re ready to adapt as we go along.

6. Do you rent or own right now? Do you plan to change your housing situation in the future?

Star: We rent, and I don’t foresee us buying a house anytime soon. We like renting because if anything breaks, we call our landlord. I’m not a fan of the total cost of home ownership which includes maintenance, insurance, housing tax, maybe an HOA, and then there’s a mortgage with interest as well. Even if we pay off the mortgage, the other costs do not stop. I read somewhere that “Rent is the ceiling, and a mortgage is the floor” – which means with rent we KNOW the most we will pay for a place to live in, but with home ownership a mortgage is just the bare minimum we have to pay. Plus, neither of us are handy and we do not enjoy trying to learn the types of things handy people do with their homes.

Joyful Jetsetter: We work to travel and I’ve always enjoyed spending extended time in places to have an immersive local experience. We’d like to give up our current rental and start living in Airbnb’s for 3 months at a time, until we find a new place to live that provides us the lifestyle we seek – more hiking, closer to family, and better weather. I’d be open to owning a home at one point if we decide to permanently settle anywhere, but that time would be far off from now.

7. Does your location have an impact on your money? Do you plan to stay in your current location forever?

Star: I don’t think location has as much of an impact on our money now while we’re working, except maybe taxes. But location would definitely have an impact after retirement and if necessary we can move to a LCOL area. We want to eventually give up our apartment here, rent elsewhere and change locations every so often, while we’re still working our remote jobs. We’d like to travel more overseas post retirement, and try geoarbitrage. We will also consider medical tourism for non urgent medical needs, to keep healthcare costs low. I want to show my wife all the beautiful places in Europe and Asia that I’ve been to, and I want her to show me all the beautiful places in the USA!

Joyful Jetsetter: I think we spend more money living in an urban environment than we will living in some of the other communities we’re looking at when we start moving around. But overall Chicago has a very low cost of living for the size of city it is. I think we also will need to anticipate the extra costs which come with exploring new communities. If we move every three months, we will constantly be in explorer mode.

8. How does money impact your relationship?

Star: I like nerding out on spreadsheets and budgets. I think keeping the ours, mine, and yours buckets help us maintain some independence in our own personal and shared financial journeys, which is very important to us. We are both strong women. My wife does not like spreadsheets, so I just ask her to save X amount per year in pre-tax, and X amount in post tax, and then leave it to her to do it her way. If she reaches the goal, great. If not, we’ll work together on how she can do it next year (and no shoe shopping till then. Please?).

Joyful Jetsetter: We have very little conflict about money and I think there are three reasons for that: First, we had important and honest discussions about money before we moved in together. I took one look at her financial situation compared to my financial situation and knew her philosophy about money would provide a better approach for our future. I knew coming in that I would have to make changes and I accepted them. Second, I’m following through with the agreements I made. And third, Star understands changing my approach to money couldn’t happen overnight after so many decades of bad behavior. She doesn’t constantly pressure me to do more and I appreciate that she understands it’s a process for me.

9. Do you have people you can talk openly with about money (not including us)? How does talking about money impact your confidence and progress?

Star: Not really, talking about money is considered taboo or rude where I’m from. If people are open to it though, I would love to engage. My wife and I may not be where we’d like to be financially yet, but we are better together now. I am not at all embarrassed to be seen in our little paid off Hyundai hatchback, while our other friends have way bigger cars or even 2 cars. I am 100% confident that we will be better off in 8-10 years with the choices we make now. We’ve got bigger goals, eyes on the prize! 

Joyful Jetsetter: I can speak very openly about money with my best friend. I’ll be honest though I’m not that interested in discussing money and finances. But I’m always telling people about FIRE and encouraging others to learn about it. If they want to know more, I direct them to Star because she’d LOVE to talk about it with them! 😊 

10. What are your personal money goals at this point in your life?

Star: I don’t really have short term personal money goals, is that weird? I believe I have a pretty good handle on what I earn, what I save, what I invest, and what I spend and give. I have several long term goals – to grow our taxable brokerage account to a point we no longer have to work. I want to learn more about tax loss harvesting, portfolio rebalancing, and mega backdoor Roth’s.

Joyful Jetsetter: My goals are simple. Have enough money to live, travel, and enjoy retirement. I also want to stop working as soon as I can and build our day to day life around the things we love: travel, learning, music, outdoor life, and being with loved ones.

11. How do you feel about money at this point in your life?

Star: I feel pretty good. For the first time in a long time I can honestly say I truly, madly, and deeply (maybe not so deeply yet), understand money. It started out as a complicated relationship, but I understand now how money can work to my advantage. There’s definitely more to learn.

Joyful Jetsetter: I feel pretty good too. I’ve had some health challenges recently which have affected my ability to work. This year I’ve only worked 6 months out of 12. Even though I’ve had a lot less money, I’ve still contributed my equal share to our joint expenses, paid my medical bills, and travelled. I’m also close to meeting the yearly savings goal Star set for me. I’ve realized I need less money to live on than I thought I did. I’ve really learned a lot about myself and money this year and that makes me feel like anything is possible.

12. What kinds of activities do you love? How do your favorite activities impact your spending?

Star: I love learning anything that does not require me to take an exam. At the moment I’m taking guitar lessons and learning Spanish. I do this in an online group setting so it’s very affordable and fun! These activities come out of my personal spending bucket. It’s important for me to be able to spend money out of my bucket for things I value and enjoy, like these online lessons. 

Joyful Jetsetter: I love travel and having new experiences. I really enjoy meeting new people whose lives are different from my own and using those experiences to expand my perspective on life. I especially love spending a couple of months in a new place living like a local versus the resort life. I love to hike and be in nature. I’m a total water baby and delight in anything having to do with water: ocean, lakes, babbling brooks, waterfalls – I love it all! My need for frequent travel definitely impacts our spending and is our largest spending category besides rent. This idea of giving up our place and moving around to different Airbnb’s is an attempt to still reach our savings goals while feeding the travel monster.

13. Last question – what are you most excited about right now?

Star: I am excited about the next phase in our lives, which is living in Airbnb’s at different locations and being close to nature and hiking trails hopefully. This means we are selling or giving away pretty much everything except for items that would fit in our little car. I am also excited about saving to a point where we would both no longer need to work – that’s still some ways away, but we will get there.

Joyful Jetsetter: I’m most excited about building a life with Star. Our one year wedding anniversary is approaching and we’ve got so much more to do and experience together. We’re better together and the world is our oyster. I’m on the edge of my seat waiting to see what happens next!

That’s it for now from the Women in the Wind! We are all looking forward to your comments!!

We are not certified financial professionals. This post contains affiliate links. For more information please read our Disclaimer.


  1. Thanks for another great interview! Star and Joyful Jetsetter sound like a really great team who are definitely headed to great places! I’m curious how long they’ve been together, and if it was hard to talk about money at first. It sounds like Star was in a slightly more solid place but that Joyful jumped right on board – was it really that easy?

    And OMG mind blown to learn about Rockin’1000. I hope Star makes that goal!!!!!!

    Liked by 2 people

    • So glad you enjoyed this interview! We think this couple is very impressive and very brave! Two people who come together from very different backgrounds with different experiences and perspectives can definitely share the same goals and values as a couple. These two are providing a great reminder for all of us!


  2. Hey Bookish Biker!

    Firstly, what a cool name! Thanks for reading 😊. We first met in 2017, and got married in 2020.
    YES it was a little awkward and hard to talk about money at first, and NO it was not easy, but we have love, respect and understanding so, anything is possible.

    I intentionally left multiple copies of finance related books just laying around the house, added the ChooseFi podcast on her Spotify and found she was open to listening to them on our road trips. We then setup free consults offered by our local branch of Capital One here and of course, we have our friends Ali and Alison who are really the rockstars in offering their views and answering our questions.

    So, it’s a journey and we’re still on the road, but now I feel we journey with intention, equipped with a map and compass. Thanks for the good wishes, I hope I make the Rockin’1000 !! 😊

    Liked by 2 people

    • We are excited to see how next year goes, rooting for you in the Rockin’1000, and so glad we have become friends! And now you’ve got a quote you can put on a shirt – “We journey with intention, equipped with a map and compass.” I just love that!! 🗺 🧭


  3. As Star said, it wasn’t easy, especially the first couple of conversations. I had to admit some hard truths. I was 47 years old and the only asset I had was my 401k. Star and I had similar salaries and we both had travelled the world. But at 38 she also had an emergency fund, took care of her parents, owned a condo, and had much more to show for her hard work than I did.

    Sometimes timing is everything and when I met Star I was really starting to get worried about my ability to retire. You could say it was kismet that we met when I was ready for her in my life and she was ready to be patient through my (ongoing) evolution.

    Liked by 1 person

    • We really appreciate how open and honest you have been on this topic – we think you are very brave and we know this is helpful for others to hear as well. You should be very proud of all of the progress you’ve made and don’t be hard on yourself. We are all just doing the best we can and continuing to learn and improve over time. Thank you so much for sharing your story Joyful Jetsetter! 👏👏👏


  4. Thanks for sharing your journey! I love seeing examples of how couples navigate money decisions and grow together! Living in places for a couple months at a time sounds like a great way to keep life fresh 🐱

    Liked by 1 person

    • We love that this couple was willing to share a very open and honest view of their process together over time. Life is a journey and so is marriage! Thanks for your comment Chickadee!


  5. Thanks for reading, Chickadee! Yes, we both like to keep things fresh and since travel is passion of ours, we’re definitely keen to try out living in different places a few months at a time. This way, I feel we can enjoy our journey together to FI, without losing sight of our ultimate destination.

    Liked by 1 person

        • I’ll answer for us – and wonder what Star and Joyful Jetsetter would say for their answer… 🙂

          We had reached a point in our nomad travels last year where we were really excited about returning to some favorite places for 2021, if things hadn’t changed with the Covid pandemic… And we had more favorites than we could fit in a year if we were going to slow down and spend 3 months in each area! But we were planning to spend 3 months in Mexico, 3 months in Japan, 3 months in Ireland and Scotland, and 3 months in SE Asia (Singapore, Vietnam, and Thailand). If we’re lucky we’ll get back to that kind of travel again some day in the future!


          • Rotating 3 continents in a year sounds great! Would you keep the AZ place or sell if that type of travel opens up again?

            I’m debating whether to save longer to try to keep a home base or sell to get freedom earlier.

            Liked by 1 person

          • I think it will be another couple of years before we return to that kind of travel, and things are too crazy to predict right now. But that gives us time to decide if we would want to turn our part of the AZ place into a rental for our housemate to manage while we travel. Maybe that would be the new plan!? Lately we have been thinking a lot about what that would be like for us! 🤷


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