Sept. 26, 2025
The Questions Gen X Women Need to Ask Our Parents Now
Episode 51: We feel like we know our parents or older relatives inside and out—but what if there are entire chapters of their lives we've never heard about? Imagine being able to ask the right questions now, so you don’t miss the chance to understand their stories, lessons, and legacies.
In this heartfelt episode, I share why midlife is the perfect time to connect with the older generation in your family. From surprising stories about college rules in the 1960s to powerful questions about values, regrets, and traditions, you’ll discover how simple conversations can deepen relationships and preserve family history for years to come.
BY THE TIME YOU FINISH LISTENING, YOU’LL DISCOVER:
✔ Why asking open-ended questions creates powerful, memorable conversations
✔ The surprising reasons we often avoid asking our parents deeper questions
✔ Simple ways to make these talks feel natural—not like an interrogation
✔ The types of stories and insights that can change how you see your family (and yourself)
🎯 OMG Moment: When an old person dies, a library burns. Every conversation you have now adds to the library you’ll carry forward.
Take Action
Want ideas to get started? Head to Patreon or Substack for a free list of sample questions and tips on how to make these conversations flow naturally.
Why This Episode Matters
As women in midlife, many of us are in the sandwich generation—caring for kids while also supporting aging parents. These conversations aren’t just about collecting stories; they’re about connection, gratitude, and legacy. Asking the right questions now ensures you carry their wisdom forward while also strengthening your bond in the present.
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Let’s talk self-care, self-talk, and owning your next chapter—without the “midlife crisis” narrative.
00:00 - The Sandwich Generation Perspective
02:45 - When a Library Burns: Lost Knowledge
06:20 - Why We Avoid These Conversations
09:10 - How to Ask Good Questions
17:48 - What to Ask Your Parents About
24:58 - Meaningful Questions for Connection
27:43 - Final Thoughts and Next Week's Preview
WEBVTT
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We've reached the age where we have parents who are getting older.
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I hate to use the O word, goodness, but it's a fact, right?
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They're getting older.
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And potentially kids or nieces, nephews who are becoming parents, or at least who are adults.
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And it's such an interesting perspective change because yes, we're in the sandwich generation phase where we might be taking care of both.
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And also we're watching both generations kind of change around us.
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And sometimes there might be things that we have missed about our parents' generation that are just powerful and special and maybe life-changing.
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Let's talk about it.
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Welcome to Mind Your Midlife, your go-to resource for confidence and success, one thought at a time.
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Unlike most advice out there, we believe that simply telling you to believe in yourself or change your habits isn't enough to wake up excited about life or feel truly confident in your body.
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Each week, you'll gain actionable strategies and, oh my goodness, powerful insights to stop feeling stuck and start loving your midlife.
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This is the Mind Your Midlife podcast.
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One of the four has a very serious health issue, however, and is not really accessible to me in the way that I would love them to be, where we could chat and we could still interact well.
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And that's been just a tremendously difficult thing to go through.
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And any of you who are going through having a parent or someone that is meaningful for you in the older generation who's going through something chronic or who is no longer with us, my heart truly goes out to you.
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It is not easy at all.
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And that being said, going through that situation with this one person has taught me so much in terms of the power of different generations, the power of family, and just the power of actually paying attention when we're interacting with people.
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So what we're talking about today is what to ask the older generation.
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I wish I could think of a better word than older.
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Maybe by the time I actually have a title for this episode, it will not say older, but here we are.
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That's always going to be the case, right?
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Our parents are not going to tell us everything, even when you have these conversations that I'm suggesting you have.
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There are definitely things we don't know.
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And what I have learned through this few years of difficult journey is there are a lot of things that I didn't know.
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And there are probably a lot of things that you don't know.
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And if you have still parents living and able to communicate with you, I don't want you to lose these things because it's so cool to learn things about this generation that we never knew.
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And maybe it becomes things that we carry on as a legacy in our families.
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Maybe it becomes things that explain something that bothered us for a long time or something that we never understood.
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Or maybe it's just fun to see that generation as more of a whole person.
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Because what I meant at the beginning of the episode is when you have adult kids, you as the parent are learning how to see those kids now as an adult, right?
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And sometimes they get frustrated with us, and I got frustrated with my parents at this point.
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So we all understand.
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We have to learn how to see them as adults, and it's a change, it's kind of filling them in from this flat two-dimensional definition to this whole person.
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And it's not done at that point.
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As our parents now maybe need help from us or support from us, we're looking at them differently, seeing new angles.
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And that can be really a powerful process.
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It doesn't have to be just about how am I going to help them out?
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What care do they need?
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I always thought of this as kind of an old, an old once upon a time.
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It used to be this way.
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Stories were passed down generations.
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But that's a thing.
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Stories get passed down generation to generation.
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And nowadays we don't communicate in the same way.
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We may or may not really spend time in large family groups telling stories and remembering things and joking about when that funny thing happened.
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So we need to be a little bit more focused on doing that because it doesn't happen naturally.
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And there's an African proverb that I found when I was researching a little bit for this episode that says, when an old person dies, a library burns.
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And I just found that to be so powerful.
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There's just so much there when we lose someone.
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This person has regrets.
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This person has hopes and dreams, some that they achieved, some that they didn't.
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This person has a whole history growing up that we never knew about because we didn't exist.
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And maybe we don't know much about them when we were growing up either, because they were taking care of us and we weren't focused on them.
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It fills in the whole person.
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And maybe, maybe fixes some blind spots that we might have about life.
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Whether this is your parent or it's uh a friend, it's someone that you're visiting in an assisted living, whatever, there are things they know that we haven't seen yet.
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Just like there are things we know that our kids haven't seen yet.
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We learn it as we grow, right?
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We learn it as we get seasoned.
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That's my favorite way of saying get older.
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And so why not try to learn from them and maybe avoid some mistakes?
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Maybe have more empathy, maybe see the value in different generations.
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And quite simply, conversation is a way that you can maintain a relationship with any person as long as they still have the mental capacity to do that.
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Maybe they're not as active, maybe they don't want to do as many things, maybe they can't travel, but they can have conversation.
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So have conversation while you can.
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Because when it goes, I can tell you from firsthand experience, it's really hard to know that you can't get that back.
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It's really hard.
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So why do we not do this?
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Why do we not just sit down with our parents and say, hey, I have questions for you.
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Tell me about your childhood.
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I think we don't necessarily think we have time to just sit down and chat.
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Maybe we aren't a sitter and a chatter.
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I have friends and people in my family who'd rather be active doing, doing, doing, right?
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That's okay.
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Maybe we think that either we would be being nosy and we might upset them, or that we already know.
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We know them.
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What questions would we need to ask?
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To be honest, I think that's how I felt.
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Of course I know my parents.
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I grew up with them.
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I've been an adult now for 30 years, and they've been involved in my life and my family's life.
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Of course, I know them.
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It's ridiculous to assume I don't.
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Don't let that stop you from having some of these conversations because there's so many cool things to learn.
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And so, what I want to do is help you.
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I want to make this easy.
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I want to give you some examples, tell you how these conversations might happen.
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And then over on Patreon and Substack for paid and free subscribers, I'm going to give you a sample list of questions and a little tips for how to have these conversations.
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I just think we need to grab this time while we can.
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And so I did a little bit of this with my one parent who I can't talk to anymore, but I didn't do enough.
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And now I'm going to go and do it with the others.
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So, what kinds of themes are we talking about?
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You probably don't know very much about their childhood.
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You may not know very much about choices they made about their career or about marriage, kids, hobbies.
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You may not know very much about things they might regret.
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That's a tough one to sit in, but it might be worth it.
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You may not know how they kind of wanted to leave a legacy and what they think is the most amazing thing that they've achieved with the family or the career or anything.
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What are they proud of?
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I love that one.
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What are they proud of?
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I mean, it's such an empowering question to ask somebody, what are you most proud of?
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Amazing.
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So I'm gonna give you some sample questions now, and then a whole list.
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So go subscribe on Patreon or Substack, find mind your midlife, patreon.com slash mindyourmidlife, mindyourmidlife.substack.com.
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It's the same, doesn't matter which one you like, and you can get the whole list.
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So the key here is to not grab a parent or an aunt or an uncle and sit down and shine a light in their eyes like an interrogation.
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Uh, we want to do this so that it feels like we are furthering a close relationship with them.
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And so you do want to be in the right mindset to do this.
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Why are we even thinking of having some discussions, asking some squat some questions to our parents?
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It's because we love them.
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It's because we know they have value and there is information that they can pass on to us that will be valuable.
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It's because we want to fill in the whole picture of who they are so we remember them in the right way.
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It's because we're grateful for them.
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We're here because of them.
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So we want to, number one, be in that mindset where we're really valuing that other person because if that's the basis of what we're thinking about, they're gonna feel it.
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It's really important that this not feel like an interrogation, right?
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So, first of all, kind of get your mindset into that.
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I love you and value you, and I want to know more about you frame of mind.
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Then you want to choose the right time.
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So, some type of relaxed setting is good.
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Maybe it's you're going for a walk or something like that.
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Maybe you're on a drive, on a trip, maybe it's a meal and you're all kind of hanging out and the TV's not on, and you you need some conversation.
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Try to just avoid people when people are stressed, when people are distracted, when you're in a rush.
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You want a casual chill moment to ask a few questions and see what they say.
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And you want to start with kind of the light questions, I'm gonna say.
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Maybe it's like fun nostalgia.
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Don't go right into how do you want to leave your legacy in the world.
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Start with fun things and make sure that this is kind of open-ended questions.
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Now, I think that some people have a natural ability to ask really great questions.
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And I think you probably know who you are listening to this.
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That was not me.
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And when I got my coaching certification a few years ago, what do coaches do?
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We ask questions to help you figure out where you're headed and how you want to get there.
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So I know how to do it now, but I had to learn.
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So open-ended questions are the powerful ones, not just a yes or no.
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Did you love going to school?
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Yes, no.
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Did you this, did you that?
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Yes, no.
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That it's gonna leave you in a situation where they say yes or no and you kind of go, hmm, okay, you don't know what else to say.
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The goal here is to start a conversation that could be a really cool conversation.
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So, what you want to say more like, tell me about when you were in high school, or what was it like when you were in college?
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For example, one of the things that I have enjoyed so much, and this has been years and years now, but my sister and I have chatted over a long period of time different things with my mom about how it was when she went to college.
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She went to college in the mountains of Virginia at a women's college that was like cousin to a men's college, so they were not very isolated as women or anything.
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And this was in the 60s, and I have always been so fascinated hearing her talk about this, and I just it was so much fun to find out more.
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So, for example, they if they went to a football game, they had to wear a skirt, no pants.
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They had, I think they had to have hose or tights, they had to wear gloves and they had to wear a hat.
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Now, I went to college around like the late 80s, early 90s.
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Uh, a skirt, a gloves, and a hat to a football game, mind-boggling.
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I've I just love picturing that.
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It just entertains me.
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And she would tell us about the house mother in her dorm and how if anyone she wanted to go on a date with came, they had to meet the house mother first, and then they had to get permission to take her out, and they could not even go off campus until something else happened.
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And I mean, it's it's mind-boggling, truly, and so cool to hear all those stories.
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Just so cool.
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Obviously, things have changed, but to me, knowing that piece about my mom, about her life and her experiences is just amazing.
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It's amazing.
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It makes me happy, it makes me feel like I know her better.
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All good things.
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So, open-ended questions is I got off on a tangent there, but open-ended questions because you just never know where it might go.
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And then you let them talk and you follow the thread.
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And so you might ask them a question about you know their college experience and they answer and they don't feel like talking about it, and then you it doesn't become anything, right?
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You move on to whatever else you're doing.
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But sometimes they're gonna say something like my mom, when she said, Oh, yeah, we weren't allowed to leave campus unless blah, blah, blah, blah, blah, blah, blah.
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And I went, What?
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How are they policing that?
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How do they even know?
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And we got into a whole conversation.
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Sometimes that's gonna happen and it's just amazing.
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And you have this knowledge that you never would have had otherwise.
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So listen and follow the threads.
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I love the idea of looking through old photos as a way to start these conversations as well.
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So you maybe are looking at a photo album or you're cleaning things out, or maybe you just have were thinking about that and you're on a walk or you're cooking dinner or you're on a drive and you go out, you know, I remember seeing this picture, you know, what was going on there?
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That makes it feel natural too.
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You want to be coming from a place of really genuine curiosity.
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I promise you, you're gonna learn some things that are either really cool or really powerful and helpful, or probably both.
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Just keep it relaxed, though.
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This is not a research project.
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You're probably not writing a book, you're just wanting to connect.
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And maybe you're sharing back and forth.
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Everybody's an adult now.
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Maybe you're talking about a summer that you loved and a vacation that you loved, and you're remembering that, and then you're asking them, well, what would you do in the summer when you were a kid or when you were that age?
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The back and forth is really powerful, and it doesn't, it doesn't make the other person feel like they're being interrogated again, right?
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And then my my next tip do know when to stop.
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If somebody seems uncomfortable or a little bit annoyed, then don't don't worry about it, right?
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No big deal.
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Either they're not in the right mood or you hit on a little bit of a hot button issue that they don't want to talk about.
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You still might have planted a seed.
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It might come up in the future.
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They might kind of think about it and bring it up in the future, you never know.
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But it's cool.
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Go back to go back to something lighter.
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It's it's not a big deal.
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We just want to see what little nuggets we can gain.
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All of that information I mentioned about my mom in college, that was many conversations over all different times over a number of years.
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So it'll add up over time, and it's such a gift for you and for me to know these things that we wouldn't have otherwise known.
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And you can even tell them that.
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You can say, I really want to know more about your life.
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I love knowing more about you.
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I'm telling you what, if my kid said that to me, I would just be I mean, so that's amazing.
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I mean, thank you.
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That's amazing.
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And I think most of the time your parent or whoever is gonna feel that way as well.
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So those are my tips for how to go about conversations like this.
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And going from a purely practical perspective, maybe you kind of take some notes of something you want to remember.
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Now, I was reading an article about this, and it said, make sure to record the audio or the video.
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And I struggle a little bit with that because it makes it feel so much more formal, don't you think?
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That you're I'm gonna, I'm turning on the phone recorder now.
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Make sure you think carefully what you say, right?
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But if you got into this cool conversation and you were like, wow, I never knew any of this.
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Like, can I can I record, make a video of us talking about this?
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This is amazing.
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I would love to share it with my sister or whatever.
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Maybe, maybe.
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Just keep it very chill.
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Maybe you just kind of write some things down after the conversation because you personally know that you'd love to tell your kids, or you'd love to tell other people in the family, or you'd love to preserve those stories.
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All right, so what am I talking about?
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What kind of questions?
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Maybe you want to know more about what their childhood was like, what their early life was like.
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There is one member of the older generation in my family who over the past, I don't know, 10 years, we've gradually learned did not have an easy childhood, and there was some emotional abuse there.
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And while I wish that hadn't happened and it was a hard thing to learn about, I'm happy that I know, if that makes sense.
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And I wouldn't have known had we just not been having these conversations about memories and things came out.
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Maybe it's about the choices they make in life.
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Maybe you want to know what matters to your mom or your dad or your uncle.
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Maybe just it's about what they really value or what they believe in.
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If you're a person of faith, maybe you want to ask them about their faith.
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It might not be exactly the same.
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We all have nuances, right?
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That's okay.
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That's really interesting to know.
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And how did that come to be?
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Maybe it's about relationships and family.
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How did they meet their spouse or their partner?
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How did they decide to have kids?
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You know, just cool stuff like that.
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You don't know that because you were the kid, probably.
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And then what about career?
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Where did they work when they got out of school?
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Do you know that?
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