Lessons Learned from Talking Money Part 1, Remembering Asha

Wow this post is an emotional one for us! Here goes…

We’re always intrigued and excited when we hear from someone new for the first time. We wonder how they found us and what made them want to reach out to us, but mostly we’re curious to know what their story is and how we can help.

In February of 2021 we got our first few emails from Asha and her husband Jan. As soon as we read the first email from Asha we were excited to get to know this couple better and become friends. Getting Asha’s first email was like having an old friend give you a book they loved because they know you’ll enjoy it. That first email was very long and it covered a bunch of different topics including various jobs they’d both held, the story of Asha’s entrepreneurial efforts, Jan’s corporate career, their feelings about holding real estate, their concerns about family members and money guilt, their experiences around volunteering and giving back, and their travel goals both for visiting other countries and living in different parts of the world. The other big topic in that first email was cancer.

In Asha’s first email to us she also answered our question about how she found us before we could even ask…

“Thank you very much for sharing your story on Retire Early Lifestyle. I’ve just discovered your site! Your stories touched me because you seek to empower women, and you’ve shared your stories so beautifully and so lovingly. Thank you for being there for the fire community on your truly incredible soulmate journey.”


That’s how Asha talked and wrote, as if she wore rose colored love glasses designed to recognize love and generosity because that’s what she was always showing to others.

Asha Olivia, 1970-2022

Asha’s first message made it clear that she and Jan were looking for new friends they could bounce some ideas off of. They wanted to have 4 sets of eyes on their numbers and 4 sets of opinions about what they might do next, and we were excited to play along.

“At this time, we’re sort of at a crossroads because we don’t really know if we’re making the right moves and what other spreadsheets we should be busting out and what other money moves make sense. We’d love to see if you’d be open to having a Zoom call with us and take a look at our spreadsheets and see if you see anything weird or glaring and what other analyses we should do or money moves you’d recommend, without being a financial or legal advisor, of course! 🙂 Your love for animals makes me trust you very much, even though I’ve never met you!”


Those first few conversations were intense! One of the hot topics we all focused on in our conversations was a whole life insurance plan that Jan wanted to use as a “volatility buffer” style of investment. Jan and Asha’s whole life insurance policy was the most disagreed upon topic between them in their personal finance picture. Should they continue paying into the policy or cancel it?

Asha had read some posts from other FIRE bloggers describing whole life insurance as a bad option for people seeking financial independence, which helped lead her to the idea that they should cancel the policy. But Jan continued to make monthly payments and he had done a tremendous amount of research on his own. Jan was convinced that his volatility buffer idea would be sound in a best case scenario where Asha stayed in remission, and in a worst case scenario if Asha did not survive the cancer she was fighting the life insurance payout would help others carry on with life.

Asha and Jan had been debating their whole life insurance strategy for a while and Asha knew from reading every post on our blog that we weren’t fans of whole life insurance policies in general, so she expected us to side with her. But we were taking both of their concerns very seriously and promised to do our own research plus whatever homework they gave us. Jan sent us a long list of articles to read and podcasts to listen to so we could understand where he was coming from with his proposed strategy. We both read every article and listened to every podcast episode Jan gave us on that topic, which was a lot! We also ran a bunch of tests on their portfolio trying to estimate what growth and interest their accounts and real estate might produce based on different scenarios and timelines. But wow did we learn a lot about whole life insurance.

And now for the hard part… Asha died of cancer a few weeks ago, which deeply depressed us. We’re still thinking about Asha and Jan every day, remembering how kind and thoughtful Asha was, wishing we could talk to her one more time. We’re sad Asha died after she emailed us for her last time, but before we replied to her one last time. We felt like too much was left unsaid.

In 2018, as we were quitting our jobs to retire early and travel full time, Asha was diagnosed with stage 4 non-smokers lung cancer and doctors told her she had only 6 months to live. Asha fought her cancer for 4 years and dealt with countless medications, procedures, clinical trials, and surgeries before the cancer spread to her brain.

We were heartbroken when Jan let us know Asha had died. We were excitedly expecting to catch up on another video chat that same week and felt robbed of that last conversation. That might seem silly since we only knew Asha for a little more than a year and never met her in real life, but every conversation we had with her was very personal so we felt like we had known her for much longer. Of course the amount of time you have with people is less important than how much you care.

This is Asha and Jan in 2021 enjoying one of our favorite cities in Mexico, San Miguel de Allende.

Alison and I started building our own personal finance community of friends in 2018 after years of only finding bloggers we couldn’t relate to in the financial independence space. Over the last four years since then we’ve met wonderful people online and in real life with experiences that are similar to ours, who we can relate to, who aren’t afraid to talk about their hopes and fears and be vulnerable, who have goals and values we understand and appreciate. Whenever we meet people like this that we really connect with, like Asha and Jan, it changes us a little.

When talking with Asha about money we were always aware that there were deep personal and financial anxieties she wanted to overcome, to build her own confidence, and especially to help her make choices for the wellbeing of others in her life.

“As you might imagine, with my possibly shortened time, we want to make the most of our lives and finances, and I also just want my husband to be financially OK without me should I go soon.”


Like many people, Asha couldn’t think about money without thinking about family. And our conversations about things like the emotional value of a house, or making financial choices based on pride or guilt, were really intense. We wanted more time to talk about all of those topics with Asha and Jan, and hoped to ease the burden of emotional money baggage they were carrying.

So what did we learn from Asha? Balancing your own wellbeing with the needs and wants of relatives and other family members can be complicated. And how much time we have with our friends and family really is out of our control.

One thing Asha was really good at was putting other people’s needs before her own. After listening to Asha share her experiences we realized she really struggled with the idea that she should put her own mask on first as the saying goes. The fact that it was hard for Asha to focus on her own health, life goals, and financial needs first was one of the topics we had a lot more to say about. We hoped to convince Asha that the goals she and Jan set for themselves should be her/their first priority, rather than spending so much of her energy putting the health and financial wellbeing of others before her own. Because Asha had such a loving and generous spirit she was more concerned about her relatives thriving after her death than she was about her own needs in life.

No matter how different our experiences are, it’s pretty easy to find commonalities. But no matter how much we care or relate, we aren’t identical. What I think and feel when my American mom asks me for money really can’t be compared at all to what a woman of color like Asha would feel. We know she worried about her family in Colombia having enough money and that was on her mind constantly. It helps a lot to tell each other our stories, and really listen to each other when we do, but then we need to let everyone decide for themselves what choices to make in their unique situations.

“Well, getting diagnosed was a turning point in my life, and my husband and I realized that, with possible limited time, we wanted to become more financially independent… As you might imagine, with my possibly shortened time, we want to make the most of our lives and finances, and I also just want my husband to be financially OK without me should I go soon.”


There were so many things we still wanted to discuss with Asha, but her remission didn’t last as long as we all had hoped. But one thing is clear – There’s great value in feeling heard and understood and being able to talk openly about things that matter including health and money.

If Asha had been able to share her own story like others have done in our Talking Money series, we’d all have more of her hopeful, positive, encouraging ideas and feelings to benefit from. She might have talked about the idea that people can find love anywhere since Asha found the love of her life (Jan) at a dog park, so don’t give up if you’re looking for your soulmate! And Asha would definitely have talked about the fact that she seriously wanted to rescue every dog that was suffering, and make sure every dog felt loved, taken care of, and protected. Asha also would’ve had more to say on the topic of entrepreneurs and women entrepreneurs specifically, since she wanted women to feel like they could be their own bosses and responsible for their own success. Asha also would have talked about her ideas of being “anti fragile” both emotionally and financially as she was often saying, “Remember your own strength!”

And then there are the fun topics like travel and being a global citizen that Asha was excited about. Asha said she felt at home in the USA, in Colombia where she had relatives and spent much of her childhood, and in Germany where her husband Jan has family. Asha was very excited about the prospect of moving again to Ireland, yet another country where she and Jan hoped to create a new life as a next adventure together. When we talk to Jan now about being on his own we can’t help hoping that he might still feel free to take that next leap.

Asha had an incredible amount of enthusiasm and joy that everyone around her benefited from. She was one of those people who would have coached her friends to put themselves first, even though she didn’t know how to put herself first. And we know she would say the same to Jan now as he decides what he wants and needs for himself moving forward – Hey Jan it’s time for you to put yourself first!

Another lesson that Asha reinforced is that financial independence actually can buy you the time and energy you need to more effectively love yourself and others, but unfortunately money can’t buy the love you need. We can’t remind Asha of this truth any longer but we can remind Jan and share it with others. Taking good care of yourself and prioritizing self-care every day doesn’t mean you love others any less. It means you deserve to be healthy in every way and you deserve to be mindful of your own needs. And if you’re anything like Asha it might help to know that self-care can also help you support the people you love.

When we look back at those early conversations with Asha and Jan we keep remembering that hotly debated whole life insurance strategy, and Asha’s concern that paying for that type of insurance seemed like a conflict with the financial independence movement. It’s true that there has been a lot of discussion about whole life insurance by bloggers in the personal finance space, often saying whole life insurance is a terrible financial strategy for most people. So here’s the next lesson we can all learn from Asha – It doesn’t matter if other people agree with your choices, and it definitely doesn’t matter if a celebrity blogger disagrees with your personal finance strategies. What matters is that you find your own path and build strategies that are right for your needs and goals.

Jan could see that it would be reasonable for them to make a major investment in whole life insurance so he created an opportunity to do so. They asked us to get in on the debate and so we did, and we were sorry to agree with Jan since it was Asha’s ongoing treatment and steadily growing cancer that made it so clear Jan’s idea was sound. Hey Jan – you did a really good job of taking care of Asha and pulling together the right strategy for your situation! We loved seeing how much you loved and cared for Asha, thank you for sharing so much with us!

“Jan and I have unconditional love and acceptance. When I go, I know he has friends like you to keep him sailing in the right direction.”


So what’s the lesson here? The lesson is that the world is full of amazing people who pour their hearts into everything they do and live with a primary goal of improving lives beyond just their own. Asha was one of those people and we’re grateful that she came into our lives.

Anyone with access to the internet can find plenty of articles and blog posts to read about personal finance topics. But just reading about the mechanics of saving and investing doesn’t always help people see how they can implement ideas, claim them for their own personal strategies, and really take action towards managing their own money successfully. That’s why we need friends we can talk to, share ideas with, learn from, and clearly see ourselves in.

For all of you who feel “whip-lashed by life” as Asha said she felt, keep putting one foot in front of the other. Talk about the important things in life with people you trust and keep growing your community. Take care of your health, take care of your wealth, and keep moving forward.

If we can become friends and be there for others like Asha and Jan, to help them create and maintain positive momentum through their own financial independence journey, the purpose of our blog has been achieved.

Thank you Asha, for sharing so much love and trust with us.


    • Thanks Chickadee! We’re so glad Jan wanted to share this story publicly, it gave us something to do that felt useful and we’re grateful for that. Asha was unique as we all are, but she also seemed so familiar and relatable so we wanted to put a little more of her voice out into the universe for others.💗

      Hope this is a good year for you!

      Liked by 1 person

    • Beth thank you, that is very kind of you to say💗

      We were actually thinking maybe it was time to think about whether the blog still had a purpose, but Asha’s death seems to have motivated us to keep going for now. We are very lucky to have met so many wonderful and big hearted people like you too over the last couple of years! Hope you are doing well and enjoying life!

      Liked by 1 person

    • Aw thank you Steph. We keep meeting such wonderful people – including you! Hope all is well and that you’re doing well during this crazy year. We should catch up soon!

      Liked by 1 person

  1. So very sorry for the loss of this beautiful human! Thank you, Ali, for another wonderful, heartfelt post. Great reminder to us all that personal finance is, ultimately, PERSONAL.<3

    Liked by 2 people

    • Thanks Kelly! Hope all is well in the land of “Traveling Lesbian FIRE believers”!!😁 Hope you are doing well this year!

      Personal finance is indeed very personal, and it’s amazing to hear what different people have experienced around money in their lives. Hope you are doing well! It feels good to know that other people who didn’t have a chance to connect with Asha directly are getting a glimpse of her personality now. She was all heart!💗

      Liked by 1 person

    • Thanks for this comment Sabrina! We are very sorry for Jan’s loss but so glad we were able to connect with Asha and Jan last year. Asha was amazing💗

      We hope you are doing well and enjoying your first year in retirement! We should catch up soon!

      Liked by 1 person

  2. I’m sorry to hear about the loss of Asha. My sister died of non-smoker’s small cell lung cancer in January, only six months after being diagnosed. She was 64 years old. She had saved her entire life for retirement and was always worried about money even though she and her husband had a nest egg large enough to see them through the leanest times. I believe her money stress contributed to body stress that helped create conditions for cancer. Her husband is now living the life he tried so hard to talk her into living.

    We’re grateful for the compassionate information and advice you two provide.

    Liked by 2 people

    • Hey Jeff thank you for this comment. We’re so sorry about your sister and the loss you all have experienced.

      Your sister’s story reminds me of my aunt who retired at 64 and then died of pancreatic cancer about two years later, which was a huge motivator for me to retire two years after that. And I absolutely agree with you about the idea of money stress contributing to body stress and cancer.

      We’re grateful to have connected with you and your wife through our blog and money conversations, and hope you are both well and happy and enjoying retirement! And we’d love to catch up since it has been a few months so I’ll DM you.

      Liked by 1 person

  3. […] Lessons Learned from Talking Money Part 1, Remembering Asha. [All Options Considered] — “There were so many things we still want to discuss with Asha, but her remission didn’t last as long as we all had hoped. But one thing is clear – There’s great value in feeling heard and understood and being able to talk openly about things that matter including health and money.” Have these conversations when you can. (Submitted by Harlan.) […]

    Liked by 1 person

  4. Thanks for sharing this write up of your friends Asha and Jan. We so appreciate your perspectives, $ wizardry, and posts like these that let us learn about and appreciate awesome humans that we haven’t met ourselves. All of this is such a gift, thank you.

    Sending you caring vibes and condolences on this heartbreaking loss. 💜🌈

    Liked by 1 person

    • Hey Barb & Kat! So great to hear from you, thanks for this comment. Losing Asha to cancer was awful and sharing her story with others made the loss easier for us. Our hearts go out to Jan now as he rebuilds his life and we are thankful that he was willing to share his wife’s story with others. He’s one of our heroes for sure!

      We are so lucky to have such a great community of personal finance friends, which are our real and truly fabulous friends, and that includes you two! We hope this tough year with Covid and a market downturn hasn’t been too hard on you. There are still so many things for all of us to be grateful for. Let’s have a video chat soon! 💜🌈


  5. […] Lessons Learned from Talking Money Part 1, Remembering Asha. [All Options Considered] — “There were so many things we still want to discuss with Asha, but her remission didn’t last as long as we all had hoped. But one thing is clear – There’s great value in feeling heard and understood and being able to talk openly about things that matter including health and money.” Have these conversations when you can. (Submitted by Harlan.) […]

    Liked by 1 person

  6. I just caught the tail end of a FIRE webinar today where you were the presenters. From the little bit I watched with interest, I loved your perspectives and I cannot wait to receive the entire replay. That, albeit brief, introduction to you both is what brought me to your website and right to this wonderful post that touched me deeply on many levels. I look forward to digging more into your blog!

    Liked by 2 people

    • Welcome and so glad you found us through the Entrust webinar. We had fun doing that brief presentation on the FIRE topic. We hope you find other posts here that you also find helpful. We would be interested to know how you are using Entrust to self direct your IRA if you are comfortable sharing? Best, Alison


      • I am actually not a customer of Entrust but somehow (serendipity??) came across their ad for the FIRE webinar. I signed up because I am always interested in hearing about like-minded people and their pursuit to FI!


        • Oh thats fun! Glad you took the chance with it. There was so much more we could have explored but there just wasn’t time. Good for you for signing up.


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