[Ally Castillo]

Would You Rather? 05.12.2025​

My, my, surprised to see me (Ally) jump into an afternoon newsletter? The lovely Emerald is on break for the week, and I will be checking in with all of you in her stead! I can only hope you don't get tired of seeing my name in your inbox this week... but enough about me! How was everyone’s weekend? Did you finally crack open that book you’ve been meaning to read since 2009? Did you try a new recipe, or just reorder from that one restaurant again? (No judgement—I'm the same way!)

I've been in a little introspective mood since Saturday and wanted to lean into a little reflection today as well. I know retirement is one of those big milestones that comes with a whole lot of freedom, and now I've got a question: Would you rather write a memoir and publish your life story for the world to read or keep a private journal and pass it down secretly to your descendants? Tell the TGV team all about it in the comments! As for me, I'd rather pass down a journal with all sorts of secret codes that my family members can try and solve—sort of like a family treasure hunt! Whether or not it leads to actual treasure is a secret I'll never tell.

Drop your thoughts below—I can’t wait to hear your takes!

Sincerely,
Ally

 

[Gayle B.]

I’m boring. I have no descendents. I would keep a journal with instructions to burn it right after I pass.

 

[GaryBlake]

I have been keeping a journal for many years for my kids. I went through a very rough patch for a looong time… almost a decade, after my divorce. I read one of my notebooks from back then, and it was very, very hard to read. Some of it was even illegible. I am pondering whether to keep it, or burn it as a cathartic.

 

[Gibb]

Really I would do neither. Things
from my past aren't for others to know.
My kids would just feel sorry for me or try to " fix " it. No thank you

 

[deaniela]

I’d definitely keep a journal and pass it on to my family. Mostly boring but some real bombshell too.

 

[Donna54]

I have a daughter she is 50 now, I write a note or letter every month and give it to her, it’s dated inside and out and also wrapped in that months holiday napkin! Sometimes it’s how my month went, sometimes to vent, sometimes money or just something I wanted to show her. It’s been a long time, she has two lock boxes! She says she won’t open till I’m gone. She will have mostly smiles I hope, lots of memories and some tears , for she is my best friend also! Just something we decided together

 

[Boyledee]

I haven't written down everything I have done in my life, I know I could write a book about all my escapades but I am a procrastinator. I come from a large family, 6 girls and I boy. My sister that is 4 years older than me has been my partner in crime and on road trips. We start with a destination but stop to check out places that are interesting . I retired and have been to many of my bucket list items. I only have a few states left. Hopefully I can get another state or two off my list soon.
Stop and smell the roses along the way. In my case it was tulips and Niagara Falls.

 

[TriciaR]

I’m boring. I have no descendents. I would keep a journal with instructions to burn it right after I pass.

Thank you for sharing @Gayle B. — and don’t sell yourself short! Everyone’s life has stories worth telling, even if they don’t seem exciting to us. I bet there are moments and memories in your journal that would make people smile, laugh, or feel seen. But hey, your ‘burn it’ plan does add a bit of mystery — very intriguing! If you were to keep just one story or memory for someone to discover one day, what would it be?

 

[TriciaR]

I have been keeping a journal for many years for my kids. I went through a very rough patch for a looong time… almost a decade, after my divorce. I read one of my notebooks from back then, and it was very, very hard to read. Some of it was even illegible. I am pondering whether to keep it, or burn it as a cathartic.

Thank you so much for sharing something so personal @GaryBlake . It takes real strength to revisit those difficult chapters of your life — especially in your own handwriting. Your journal is such a powerful gift to your kids, and even the tough parts tell a story of resilience. If you do decide to keep it, maybe you’ll find a way to include a note that explains how far you’ve come. Or if you choose to let it go, that too can be a healing act. What do you think your kids would take away from reading that part of your journey?

 

[TriciaR]

Really I would do neither. Things
from my past aren't for others to know.
My kids would just feel sorry for me or try to " fix " it. No thank you

Thank you for sharing @Gibb — that’s a very personal and thoughtful stance. It takes strength to set boundaries around your own story, especially when you know how others might react. Your choice reflects a deep awareness of what feels right for you, and that’s something to be respected.

 

[TriciaR]

I’d definitely keep a journal and pass it on to my family. Mostly boring but some real bombshell too.

Thank you for sharing @deaniela — sounds like a journal your family won’t be able to put down! A mix of everyday life and a few bombshells? That’s the perfect recipe for a page-turner. What’s one little teaser you’d be willing to share from the ‘bombshell’ section?

 

[TriciaR]

I have a daughter she is 50 now, I write a note or letter every month and give it to her, it’s dated inside and out and also wrapped in that months holiday napkin! Sometimes it’s how my month went, sometimes to vent, sometimes money or just something I wanted to show her. It’s been a long time, she has two lock boxes! She says she won’t open till I’m gone. She will have mostly smiles I hope, lots of memories and some tears , for she is my best friend also! Just something we decided together

Thank you so much for sharing this lovely story @Donna54 . What a beautiful and thoughtful way to keep your bond strong — those letters wrapped in holiday napkins sound so special and personal. It’s clear how much love and trust there is between you and your daughter. What a precious treasure she will have, filled with memories and emotions only you two share. Do you have a favorite letter or moment from this tradition that always brings a smile?

 

[TriciaR]

I haven't written down everything I have done in my life, I know I could write a book about all my escapades but I am a procrastinator. I come from a large family, 6 girls and I boy. My sister that is 4 years older than me has been my partner in crime and on road trips. We start with a destination but stop to check out places that are interesting . I retired and have been to many of my bucket list items. I only have a few states left. Hopefully I can get another state or two off my list soon.
Stop and smell the roses along the way. In my case it was tulips and Niagara Falls.

Thank you for sharing your amazing journey @Boyledee ! What a fun and lively life you’ve had, especially with your sister as your partner in crime — those spontaneous stops make the best memories. It sounds like you’re living your bucket list to the fullest, and Niagara Falls and tulips must have been spectacular moments. Which state are you hoping to explore next? And any favorite ‘off-the-beaten-path’ spots you’ve discovered on your travels?

 

[GaryBlake]

Thank you so much for sharing something so personal @GaryBlake . It takes real strength to revisit those difficult chapters of your life — especially in your own handwriting. Your journal is such a powerful gift to your kids, and even the tough parts tell a story of resilience. If you do decide to keep it, maybe you’ll find a way to include a note that explains how far you’ve come. Or if you choose to let it go, that too can be a healing act. What do you think your kids would take away from reading that part of your journey?

I have decided to keep it. My kids know I am imperfect. I have never represented myself to them any other way, yet, they love love me deeply.

 

[TriciaR]

I have decided to keep it. My kids know I am imperfect. I have never represented myself to them any other way, yet, they love love me deeply.

It’s truly inspiring to hear how embracing your imperfections has built such a deep and loving bond with your kids. Being genuine and authentic is one of the greatest gifts we can give ourselves and those around us. Your story is a lovely reminder that love grows strongest when we’re real. Thanks as always @GaryBlake , for opening your heart to us!