In this heartfelt and wide-ranging episode, listeners sent in deeply personal questions — and Wendy responds with honest, compassionate insight. From navigating friendships in your 70s, to handling retirement conversations at family gatherings, to ageism in the workplace, to fears about caregiving and widowhood, this episode goes straight into the real challenges we face as we age.

Wendy also answers personal questions about her own fears, where she sees herself in a few years, and the best (and hardest) parts of her day. You’ll hear stories from her life, wisdom from widowed friends, and practical steps you can take today to build a more meaningful and connected next chapter.

If you’ve ever wondered, “Is anyone else feeling what I’m feeling?” — this episode is for you.

Key Takeaways:

• Wanting connection is not neediness. It’s human.
• Friendship grows best when you pace yourself and allow reciprocity.
• Boundaries during holiday conversations protect your peace.
• Ageism and sexism are real — and they don’t diminish your worth.
• Caregiving looks different for everyone; compassion takes many forms.
• Widowhood is survivable, but not simple — community matters.
• Most money fears soften when you replace worry with action.
• You can choose what your next chapter looks like.
• Gratitude is powerful — especially at the end of a long day.

Links & Resources Mentioned:

Book a complimentary 30-minute call with Wendy: https://calendly.com/boomer-banter/30minutes

Take the “What’s Keeping You Stuck?” Quiz: https://bit.ly/NotStuck-Renewed

Adrienne Berg’s podcast, The Ageless Traveler: https://agelesstraveler.com

WE WANT TO HEAR FROM YOU

Did you enjoy this Q&A-style episode?

Let Wendy know — your feedback helps decide whether we do more episodes like this in the future.

Hello, and welcome to Boomer Banter, where we have real talk about aging. Well, my name is Wendy Green, and I am your host.

So every week on Boomer Banter, we talk about the challenges, the changes, and the possibilities that come with this season of life. Today, though, we're doing something a little bit different. Over the past week, I've asked listeners to send in questions, and many of you have.

You sent in thoughtful, heartfelt questions about things that we all wrestle with as we get older, and so things about connection and retirement, bias, caregiving, money, loneliness, hope.

You also sent in questions that were honest and vulnerable, and my hope is that I answer them in a way that speaks to your own life, even if the specific question isn't yours. I did wish that I could have talked to each one of you personally to explore what is really behind the questions you sent.

What fears, beliefs, thoughts are triggered by the events that brought you to asking your questions. I also received questions about me, questions about how I live my life, my thoughts about the future, and things I worry about.

These questions really made me think, and. And for that, I'm grateful.

I think it helps when you kind of explore yourself a little bit and dig into some of the stuff that you just kind of take for granted. So thank you for those questions as well. So let's jump in. Our first question is from Irene. She's 72.

She wrote that she has a husband she loves and one close friend. But she wants more connection, and she's worried that she comes across as needy.

She's heard all the advice, you know, take the classes, go to the community center, and she's done that.

But the problem that she is recognizing in herself is that sometimes, maybe most of the time, according to Irene, she gives more than she gets in these friendships, and so the friendship does not feel equal. And then there's a dependency on this one friend who also has other friends, and so it becomes that it turns into that needy feeling.

So, Irene, this thought of coming across as needy, a lot of people experience that. You know, we tend to put all our eggs in one or two baskets. And I think we do that more as women. And sometimes we also feel needy when we really.

What we really feel is lonely.

Or maybe you've tried before to make a friend and gotten hurt, and so now you're like, oh, feeling a little more desperate, or maybe you worry that you're asking too much of people. But here's the truth. Wanting connection is not neediness. It's a sign that you're paying attention to Your own emotional life, and that's healthy.

Something in your message also really stood out for me. You notice that you become very giving in friendships. And when we over give early on, it can create an imbalance.

Not because you're doing anything wrong, but because you're trying to build connection through effort instead of letting it grow naturally. So one thing you might want to try is to pace yourself a little bit more.

When you meet a potential new friend, invite them for a short, short walk instead of like a big event, or meet them for coffee. And then an hour is up and it's time to leave. And at the end of that hour, you might say, you know, I really enjoyed this. This was fun.

And then pause and see what they say. Are they going to be the one to initiate the next visit? Will they say, hey, I like this too? What? Let's do this again sometime? So that's a.

A healthier way. It's like give and take on both sides. It's a healthier way to build a more balanced connection.

And it also means that you, Irene, are not carrying the whole weight of building the friendship. When you're someone who naturally gives a lot.

Easing off the gas a little and allowing the other person to participate is not always easy, but it also could help the friendship unfold more naturally. It's not about withholding your kind, caring part, but it's about giving the connection room to grow without pushing it along too quickly.

The other thing you might want to try is environments where the goal isn't friendship, but service and shared purpose. I'm talking about things like volunteering or, you know, finding a local Rotary Club or some.

Some kind of service organization, maybe helping at a food pantry or an animal shelter. Something that you know you already have an interest in. And you will find that in those spaces. It's not just about making friendships.

It's really more about doing the work that you signed up for for that organization. And it takes the pressure off. And friendships build more organically that way. So that might be worth trying.

And there's one more piece of something that I'd like you to consider, and that is becoming comfortable with our own company. So, for instance, take yourself to a farmer's market or take yourself out for coffee. Treat yourself like someone you enjoy spending time with.

When we're comfortable with our own company, we don't walk into situations with the energy of, oh, please like me, I hope I make a friend here. We walk in as grounded, open people, and that makes connection easier.

You become more approachable, more comfortable with yourself and more you exude that comfort out to other people. So here's something to think about. Irene, you're not needy. You want connection, and you recognize that it's important to you.

And behavior change is not easy. It is an opportunity for growth. So celebrate your small steps as you build your new connections.

And I look forward to hearing how this goes, and thank you for this question. All right, moving on. This next one made me smile because it's so relatable and it's so timely.

Leon asks, what should a newly retired person or someone who's thinking about retiring expect to hear from friends and family over the holidays? And how do you answer their questions? Well, we all know families love to ask questions.

You know, when you're young or if you have young people in your family, people are asking them, you know, when are you going to get married? Or if they're married, when are you going to have children? As older adults, we get asked, so what are your plans? When are you going to retire?

You're already old already. Come on, retire. Be like the rest of us.

And sometimes, you know, these are really questions that are asked with love and interest, and sometimes they do carry a hint of pressure. So let's say someone says, so, Leon, when are you going to retire? You're over 65. Well, you can keep it light.

You could say something like, you know what? I actually love what I do. I'll let you know when that changes. And truthfully, you really don't owe them any more than that.

But if you've already retired and someone wants to know what's next, you can share a little. If it feels right.

So you know, you know, the people that you can trust or the people that are judging you or the people that are going to come back with all kinds of advice so you want to share if it feels safe and right. If it doesn't, flip it back to them. You might say something like, you know what? I'm exploring new things.

And then ask them, what surprised you most when you retired? Or what have you figured out to do when you've retired?

You know, people love to talk about themselves, and who knows, you might learn something useful from them. But the big thing is this retirement, as we all know, is not a finish line. It's a transition. And you don't have to have all the answers right away.

In fact, it takes time. And we evolve and we explore new ideas. And so you're allowed to say, I'm giving myself space to figure out what feels right.

It's a perfectly legitimate answer. So good luck at your Thanksgiving dinner. This next question comes from Judy, and her story is powerful. Judy ran a farm for many, many years.

She operated the equipment, she kept the records. She made all the business decisions. She did everything. And when she left the farm and applied for jobs, she was turned away for two reasons.

She says because she was a woman or because they told her she was overqualified. And Judy, what you experienced is real, as you know, and it's painful. It's not about your ability.

It's about the bias in the workplace, which you pointed out in your question.

Gender bias and age bias often overlap and they can make trying to find a new job when you're, when you're in any of these groups, it can make it really, really difficult sometimes. In my experience, overqualified is the code for we don't know what would do with a woman who has this much skill.

Or we're really looking for someone younger because they're cheaper. They're not really looking for the experience. So it has nothing to do with you or your worth or your skills.

The thing I want you to hold on to is that you didn't fail at getting these jobs. They failed at recognizing you. And I know that doesn't make it easier. And finding jobs over 50, particularly for older women, is challenging.

I don't know what you're doing now, but women who have run complex operations like you've done, they often go on to do meaningful consulting, maybe to other farms, or they take leadership roles in nonprofits or organizing events in communities. Maybe they become a coach or they take on project based work. Your expertise didn't disappear just because someone else couldn't see it.

Judy, you are a strong, competent woman with many skills to offer. I know this just from our online engagement.

There is so much more to say about some of the work obstacles that we encounter as older adults, but particularly as older women.

But each conversation about the work opportunities or what's next are so personal to the individual because it depends on where your interests are and where your energy level is and what you really want to do. So I'm going to ask if you've considered talking to a coach about what you want to do next and how much you can do to make what's next happen.

I don't feel like I've completely answered your question, but I think I've given, hopefully given you some things to think about. It is an ongoing challenge, and I think it's going to continue in the future. And as we all Continue to age. And, you know, they.

They want to hire younger people. They think they'll stay longer, which is, of course, a little crazy because we have a stronger sense of loyalty in our generation.

The younger generation seems to move around a lot, but I don't want to go there. This is a whole. That's a whole other can of worms. All right, next. This next one is tender.

Lottie asked, will I be as compassionate a caregiver as my sister was, and will I survive being a widow? I had to think a lot about this, and I had to get some help with this answer. So first, comparing yourself to your sister doesn't help you.

Her caregiving style came from her personality, her relationship, in her marriage. It came from the moment that she was in. Compassion looks different for everyone.

And often when people ask this question, it's because they care deeply already. So, lady, if we were sitting together, I'd ask why you believe you wouldn't be compassionate? Most of that time?

That belief comes from fear, not truth. I know you to be a compassionate person, so there is no worry there. It's the comparison, I think, that's getting in your way right now.

But caregiving is not about doing it the way someone else did. It's about caring in the way that fits you and the person you love.

This might be a good time to talk gently with your husband about how he would want to be cared for. We often assume we know because of how we think we would want to be cared for.

But the other person may have different needs and desires for how they'd want to be cared for. And a conversation like that now, when you're both healthy, can be very helpful, you know, instead of waiting until you really need to know.

And the widowhood part of your question, probably something most of us will worry about. But the truth is, yes, Lottie, you will survive. But grieving a spouse is not simple. It's not a straight line.

Grief is not only about losing your partner. It stirs up losses from your whole life. When you lost your mother or you lost a best friend, it shakes your identity.

It can feel like the ground drops out from under you. But because I haven't lived this myself, I haven't lost a spouse. I asked a couple of friends who have, and what they shared with me, I so appreciate.

It was honest and raw, and it brought up a lot of feelings for them. My friend Nikki said, if you're asking about dealing with grief and being alone, the first thing is choose not to be alone.

Seek out a grief group talk To a counselor, get vulnerable with your feelings. Connect with others who are also grieving. And then she said it took her two years before she was ready to even do that.

So know that there is no timeline to your grief and no timeline that you have to meet. And then my friend Ann shared something a little bit different. She said it's just grief.

Even when you know your spouse is dying and you know you'll be alone, nothing prepares you for the reality of it. She told me that when her husband was dying, he worried about how she would manage. She reassured him that she would be okay.

But after he passed, she said the feeling of losing the love of her life never fully leaves. It's been nine years almost, and she still dreams about him, still wakes up thinking of him. She also said that a friend gave her advice that helped.

Her friend told her to say yes to all the invitations she gets. Dinner invitations, go out to a play, come over and let's have coffee, let's do lunch, anything that got her out of the house.

And she said, at first it was so uncomfortable, but it was healing. And also kept her involvement in Rotary and her church.

Her good friends took care of her, and she said she is grateful that she and her husband had time to talk about what was coming and what could be next. So Ann and Nikki both talk about the value of connection.

You have to have somewhere where you feel people are understanding and supportive and caring for you and not. You know, some people say things that aren't the right thing to say.

You know, like, you should be over this already, or they're in a better place, or whatever. It is something that you don't really want to hear or need to hear at that moment.

So you want to be sure you have your connections, which is something we talk about a lot. And when you ask, will I survive being a widow? The answer is yes, you will. Not because it's easy, but because grief and love can coexist.

Because your community will help to hold you up. Because saying yes to small things like Anne's head eventually opens the door to bigger things.

And because your resilience grows in ways that you can't imagine until you need it to. So, Lottie, you don't really have to prepare for widowhood today.

You just need to know that you'll have the support and that healing isn't forgetting. It's learning how to carry love forward while finding your way into a life that still has meaning. So let's move on to money worries.

Here's a big one that almost Everyone wonders about, but doesn't say much about. Will I run out of money before I run out of life? And should I go back to work? So obviously I can't answer, will you run out of money?

But it's a normal fear. I mean, I worry about it also. We're living longer, most of us don't have pensions and the financial landscape is complicated.

I think the first thing I would suggest is meeting with a financial planner.

Many will do a free first meeting and they can run, you know, scenarios that are tailored to your age, your health, your family history, your savings, your Social Security timeline. And that's going to give you some real information to make decisions on and not this fear based guessing that a lot of us do.

But I really think there's a second part to this question, and that is, do you want to work? I mean, some people miss feeling useful, some want structure, some want extra income, some want to try something new.

There are many low pressure ways to bring in a little extra income. If that's your goal.

You could look for seasonal work, you could do tutoring, maybe you have crafts you could sell, you could do pet sitting, if you like animals, consulting, farmer, market booth. There's all kinds of things that you could try. But the thing is you get to choose what this part of your life feels like.

Money is one piece, meaning is another. What to do next is really the sweet spot of my coaching. So reach out if you have questions in that area.

All right, well, now I want to move on to some of the personal questions that I got. And they were, they were interesting and like I said, they were challenging. They made me really think so.

First one, she said, what do you worry about? And do you have fears? Well, yes, of course I have fears. I think everyone has fears.

Some people might put on a fearless person Persona, but if they're honest with themselves, there's always something. One of my worries, like we talked about earlier, is whether I'll outlive my money. And that's a very common worry.

But here's something I've learned about fear and worry. These are projections onto the future, which we don't know. All we know is right now, right? They're about things that might happen.

And worrying, it creates this like circular thinking, like, oh, what if that happens? Oh, gosh, well, then what if that happens? And then what if that happens? And that kind of worry, it doesn't change anything.

So when I notice myself worrying, I ask to myself, I say, self, is there something I can do to reduce this risk or this worry. And if the answer is yes, like making a little more money or cutting expenses or meeting with a financial planner, then I try to take that step.

But if the answer is no, you know, like when my daughter or grandchildren are on the road, you know, I could worry about their drive. But I remind myself that worrying is not going to protect them.

It's not going to make them safer, and all it's going to do is make me uncomfortable, and it's not going to change the outcome. So I try to let go of that worry and really switch it to trust.

Trust that they will be careful, other drivers will be careful, and they will get to where they're going safely. It's not always easy, but it is something that I've been training myself to do better at. Because wor worry is like hurting yourself, you know, and.

And we try to live a good, healthy life. We don't want to hurt ourselves.

And sometimes worry is about hurting others because if you're doing too much worrying about them and they know you're worrying about them, they may feel like you don't have confidence in them. And so that puts a strain on the relationship.

So if it's worrying about someone else, you really have no control over that someone else now that they're all adults. If you're worrying about something for yourself, like money or health or your relationships, that is something you can do something about.

And so thinking about ways that you can address that to be more proactive and reduce the worry could be a good strategy. There are also bigger, less personal worries that I have.

I worry about the division in our country and the anger and the lack of empathy we're seeing. Again, I ask myself, what can I actually do? Like, I can't stop the division and the anger and the frustration that people are feeling.

But for me, what I can do is I can include in my circle of people that I spend time with, I can include people from different backgrounds and different thoughts and different cultures and have conversations where I'm listening to understand not to be right, not to win, not to persuade them to my way. And some of that part of what I'm learning is a lesson I'm learning from my dear sweet partner, who is very good at that.

And so listening to understand.

You know what, it helps me feel less helpless because it shows me that connection between people from different backgrounds and different, different belief systems. Connection is still possible sometimes, right? They have to be willing to listen and connect back. Right? You can't do it all yourself.

Okay, another question. I love this question, where do I see myself in five years? So I'm 72. That would be 77. Well, I. I plan on still doing the podcast.

I love having a place to learn and share, and I learned so much from my guests and from all of you. And I also plan to have a budding and growing coaching practice. My ideal is to have three or four regular clients throughout the year.

Not the same three or four, but, you know, consistently three or. And I want to support people in creating a life that feels true and exciting for them.

I also, you know, would like to make some of that supplemental income that we talked about earlier.

And you know what, doing that kind of work, like, I could go try and work at Starbucks or Home Depot or something, but doing the kind of work that gives people the belief that they can live the life they want to lead, that really is so fulfilling for me. So that's what I want to do with that. And I also see myself. Oh, goodness, here's the one that you guys have to hold me to this.

I see myself as a sought after speaker at conferences, women's gatherings, and organizations that focus on people over 60. That's something I really want to do. I'm really leaning into.

I can reach more people to give them the encouragement and the belief that there is more to life after 60 than just fading away. And personally, I plan to keep living a healthy lifestyle. Walking, exercising, paying attention to nutrition.

I see my relationship with my partner continuing to deepen, and I look forward to many more travel adventures with him. So thanks for this question. It's good to dream out loud every now and then.

A little scary sometimes, but now that you've heard it, you all can hold me accountable for these dreams. And since I mentioned travel, this is a good time to mention my friend Adrienne Berg and her podcast, the Ageless Traveler.

When you listen to the Ageless Traveler, you will learn about travel, health, and traveling to exotic locations. She will give you tools and ideas and tips so you never stop traveling. You can listen anywhere you get your podcast. Look for Ageless Traveler.

Or you can, and you can subscribe to her free newsletter, Travel Tuesday@ageless traveler.com. let's end on a fun one. Okay, so Lottie asked, what is the best part of your day and what is the worst part of your day?

Well, the best part of my day was easy. That was the easy answer. It's the morning. I always love the mornings. I'm a morning person. I settle in with my coffee very early.

I usually take out a book and a journal. And the reason I, you know, I'm just sharper in the morning than at night.

And the books that I read are usually something I want to learn from or books by authors who'll be coming on my show. And if I wait until the evening or the end of the day, I will get to one or two pages before I'm starting to nod. So morning is really my.

My precious time for reading and absorbing. And then most days after that I try to go to the gym or for a walk. Doesn't always happen.

But I do know that I feel better for the rest of the day when I have some movement in the morning. But the second part of the question, the worst part of my day. I don't think I have a worse part of my day.

I have hard moments when unexpected things happen.

Like the day Rolling Green Village called to tell me my mother was being taken to the hospital or dealing with customer service for a credit card company or a cable company. You know how frustrating that can be.

You could be on the phone for hours with those people or coming home after Christmas last year to find my refrigerator had died, flooded the kitchen and ruined everything ins the minor inconveniences don't usually ruin my day. You know, they frustrate me for the time, but they don't ruin my day. Family dynamics can be challenging.

I think that's true for most families and that can be hurtful. When something with the family goes wrong or someone you love goes wrong, it can ruin your day or maybe even a couple of days.

But that's not what the question was. The question was really about what's the worst part of my day. And I can't think of anything. I don't have a worst part of my day.

Mostly I have pretty good days and I try to end my days by thinking about what I'm grateful for. And I want to say as we wrap up this episode that I'm grateful for. All of you that sent in questions, this is been amazing. So thank you so much.

And your questions, they really made me think they were honest, they were vulnerable, curious, brave, and I hope I did them justice with some of the answers that I shared and maybe gave you something to think about in your life. And as I said in the beginning, I wished I could have spoken to each one of you.

I feel like there is more to talk about than what I was able to really talk about in depth in each of these episodes.

So, you know, if you want to talk a little bit more, those of you who sent in questions or those of you who know didn't get to ask a question or your question wasn't asked. You can always book a 30 minute complimentary time with me and we'll just chat and see if we can dig a little deeper and find out what's going on.

You can use my Calend Calendly link by going to calendly.com boomer D banter 30 minutes calendly.com/boomer-banter/ 30 minutes and I promise I will put that into the show notes. I also want to know what you thought of this format. Did you like this Q and A style? Was it helpful?

Let me know because your feedback will help me decide if I should do something like this again. This was an experiment so, you know, no hard feelings. You can tell me it was okay or it was great. I want to do this again and think about this.

Life at this stage may look different, but it doesn't have to get smaller. There's still room for new friendships, new ideas, new ways of growing and new ways of showing up. You are not done.

You are just becoming somebody, I don't know, not newer, but maybe more true to who you really are.

And before we wrap up, if today's episode brought up anything and you started to think, maybe I'm a little bit stuck, maybe there's something else I'm curious about. I did make this what's keeping me stuck quiz that you can try.

It will tell you what your stuck type is and give you like a series of five emails over the next 10 days or so. That will give you some ideas of ways to get unstuck. You can try it at bitbit ly slash not stuck. Right? Renewed.

And again, that will also be in the show notes. So I want to wish everybody a happy, delicious Thanksgiving. Thank you so much for your questions and for spending time with me today.

Take good care of yourselves and I will see you. See you next week on Boomer Banter.