An Interview with Jesse: Choosing Sanity while in the Sandwich Generation
On navigating caregiving without siblings, cognitive decline, not being safe to drive, and creating sustainable family boundaries and routines.
Jesse is deep in the Sandwich Generation—simultaneously raising a 16 year old and an almost 10 year old while supporting his 85 year old mother and her increasing needs and memory loss. Jesse’s story offers an honest look at the emotional challenges of his role and the hard-won clarity found in setting boundaries and doing the internal work. With no siblings to share the caregiving burden for his mother, Jesse and his wife, Heather, had to intentionally chart a path, leaning on the mantra choose sanity. This is an essential conversation for any caregiver struggling with guilt, managing complicated family history, or trying to find a better way through the complex demands of being in the sandwich generation.
Setting the Scene: An Only Child and a Single Parent
Lissy: Okay, let’s start by having you share about where you are within the sandwich generation. Set the scene of what your family situation is like.
Jesse: My older daughter is 16 years old, and she just got her driver’s license. My younger daughter is going to be 10 in January. My wife, Heather, and I have been married for 19 years. I would say, knock on wood, we have a really stable family life. Yes, there’s obviously the day-to-day craziness, but at a very basic level, we all love each other and communicate clearly.
And then on the parent side, my mom is 85 years old. My mom and dad were never together. Growing up, I always lived with my mom, just the two of us. So it’s just me taking care of my mom.
Lissy: I’m curious to know when you started feeling like more intentional caregiving had to start happening?
Jesse: In hindsight, I have always been some sort of caregiving for my mom. Still to this day, my mom will always say things like, you are the best son and my best friend and my therapist.
Lissy: Emotionally it was always just a part of your dynamic.
The Tipping Point: Cognitive Decline and Anxiety
Jesse: About four years ago, I was starting to realize that there were some very subtle memory things starting to happen for my mom, and she needed more support. That’s when I felt like something started to shift where I was like, oh, shit, I need to start being a more active participant in my mom’s aging slash living process. We moved her into a friend’s house, four blocks away from us. And there was kind of something that broke for her in that move, emotionally.
In retrospect, her doctors said that the early stages of some dementia or memory loss will often accelerate when there is a major life change. You have all this scaffolding and you can kind of hide it and buoy yourself with your routines.
Lissy: I think that is really telling, the idea that people can rely on their routines to kind of mask or ignore or evade the memory issues they’re having. And then you put them into a new situation that you think is supposed to improve things and then the opposite is true, at least initially.
Jesse: That’s exactly right.
Lissy: It’s startling.
Prioritizing the Nuclear Family: Boundaries and Sanity
Lissy: What was the communication like with your mom around the cognitive decline and anxiety symptoms that you were noticing?
Jesse: Initially, I just tried to keep it light with her. But I was having to work with a lot of frustration. Because it was the same conversations over and over again.
I remember our couples therapist told us when Heather and I first got married, he drew a circle and he’s like, there’s a new thing that’s happened. It’s like you and you in here (points to circle). And your family is here now (outside circle). And your number one priority is each other. So I tried to share that with mom. Heather and I are going to be there for you, but not at the expense of my marriage and my kids. If I’m feeling guilty that we haven’t seen her in four or five days, but one of the kids had something that they need my support around right now, then that’s going to be my top priority.
Lissy: Yeah. I talk about this with folks a lot, tapping into the “why” when you want to go spend time with your parents. If you’re going because you feel guilty, then that’s not necessarily how you want to show up for a visit.
Jesse: Exactly. Heather and I have a family mantra of always choose sanity. In this moment, of the sort of choices we see in front of us, what’s the most sane? For me, for Heather, for us, our kids, and then mom, and trying to do it in that order, honestly.
Making the Call on Driving: Guilt and Worry
Jesse: So at this point, she slowly adjusted into her new house that she was sharing with another woman, and we could see that she could still live on her own. And she’s still taking care of things. But this was when I was like, I’m not sure she should be driving. We need to have a conversation about the car.
And I would send her little things. Kaiser Permanente put out this thing about what happens when you’re 80 years old and you drive. Just the pure mechanics of an 80 year old and their reaction time. I tried to start sharing some of this, just trying to normalize what’s happening.
One of the barometers I used with her driving was: if she hurt someone, how would I feel? That was one of the ways that I was trying to track and make sense of it. And there started to be a moment where I was like, Oh, I think I would feel really guilty. And also Heather, was like, Babe, I don’t feel good about this anymore. And then mom got in a car accident. She didn’t hurt anyone. She didn’t hurt herself. The car is no longer functional. And that was that.
Part of the sandwich generation is witnessing my daughter get her driver’s license in the same time frame that we removed my mom’s ability to drive. Because you just see both so clearly in concert. The absolute freedom and independence and feeling like an individual because of being able to drive. And then the opposite of ripping that freedom away from someone.
Independent Living: Troubleshooting & Finding What Works
Lissy: Tell me about your mom’s friends and community.
Jesse: She has long time friends in the Buddhist community. But what you start to see is, of the 8 to 10 really close friends, there’s really only 2 of them that are patient and skillful with her. And the rest are kind of just, like enough with the complaining. Enough with repeating everything.
Lissy: That’s really hard. And I think it puts pressure on you and your family.
Jesse: That’s exactly right. Around this time, Heather started trying to take her to the local Rec Center for senior lunch. And my mom would just be like, that meal was so salty. I would never be friends with those people. Heather would come back from it and just sort of be like, What the fuck?
Lissy: I mean, it seems like there’s a certain amount of troubleshooting that needs to happen. Where I think Heather’s impulse to jump in and “do” is so normal. Figuring how to fit in the puzzle of helping her find a new routine. And then to get that negative feedback is just so hard.
Jesse: That’s exactly right. And so it got to a place where I had to say Hon, I don’t want you to do that anymore. I would actually rather shoulder much more of the burden, and know that you can just be supportive of me and the girls.
At this point, my mom didn’t have a car. Heather and I were shopping for her every couple of days. My mom would come over, and she would just sit there silently, unmoving. We started to realize that sadly it wasn’t good for the kids, for us, or for my mom. I’d be on edge. Heather would be on edge. The girls. I started feeling really guilty.
And that’s when Heather was like, “okay, I called 6 independent living places, and I’m gonna go look at them.” It just became clear, we’re rewriting this whole thing.
Lissy: And what a gift for Heather to be like, let’s do this. I’ve taken these steps.
Jesse: It was so helpful, it was exactly the kind of help I needed.
Finding Ease: Structured & Predictability
Lissy: And I think it’s also going back to figuring out what everybody’s roles can be.
Jesse: And this is exactly why I’m so excited for the stuff you’re doing, because I feel like we just stumbled our way through it. Trial and error. This doesn’t work. We’re having too many fights. I don’t know how this works. Because she’s older than all of my friends’ parents. They’re not there yet.
Lissy: I was wondering about that, if you felt like you had friends going through it along with you.
Jesse: No.
Lissy: You’re kind of charting the path.
Jesse: I kind of am.
Jesse: In that process of finding an independent living option for my mom, Heather and I started to realize that we need to create structure around the visits. So about once a week, I’ll go and spend a couple hours with my mom. Then, roughly three times a month, my daughter and I will go in and we bust her out of there, and we take her out for dinner. And it really works because it’s a very defined beginning and end. My daughter can do that, she can show up and be her best self.
Lissy: I think that’s so smart. Being intentional about it, with predictability both for your mom and for your family. It allows the relationship to be so much more easeful.
Jesse: It totally does. And then around once per month there’s a family gathering and we’ll all be together and it’s usually a little bit too much for mom, but it’s buoyed by the fact that there’s a lot of other people there and it’s not the only way we are spending time together.
Lissy: How long has she been in independent living now?
Jesse: It has been four months. I just can’t say enough good things. I just know that there’s eyes on her every single day. There’s three meals a day. Her short term memory is not great at all. Early on, the staff did some troubleshooting to help her remember the meal times, and put a nice little thing on her fridge. But now she’s totally in the routine. Even this morning when I called her, she was like, I can’t talk. I’m going to the poetry reading. She’s doing all the things!
Lissy: And that speaks to the importance of letting the dust settle, especially for someone with anxiety symptoms. We’re not going to judge this stuff on how it feels one month in. We’re going to give her ample time to settle into and tap into the new routine.
A Continual Process: Doing the Internal Work
Lissy: I’m wondering about what you found to be the most helpful and supportive when you guys were in the thick of it.
Jesse: Yeah, probably a handful of things. One of them was the mantra of, “choose sanity.” And having a partner who could help with that. It wasn’t choosing the perfect. We’re not trying to figure everything out. You can’t, you know? So in this moment, of the sort of choices we see in front of us, what’s the most sane?
Another thing that was helpful was doing the internal work. I had this realization, when things were a bit more intense, that it’s very possible that my mom could die in the night. And our last interaction might not have been positive or a heartfelt connection. And that’s okay. I have been a good son. I’ve done as best a job as I can. There’s something there that has taken some of the pressure off.
Lissy: And if you had continued to try to have her live in the apartment with you worrying about her and serving as her sole support, I wonder if you would have been able to access that internal work? Because you would have been so overwhelmed and stressed and dysregulated. And then it’s harder to tap into that emotional processing.
Jesse: You’re absolutely right. And I can get stuck a little in the planning, I’m a real overthinker, spreadsheeter kind of person. And look, I’m under no illusion that the work is done, right? Sometime in the future, we’re gonna go through the next tranche, and need to figure it out. It’s like, there’s a little victory right now and it’s clearly short lived.
When I find myself worrying about the future and potential outcomes, Heather says, “we can only do what we can do right now. This is the right choice for right now. We want to provide her the opportunity to have joy in her life right now. I want her final years to be as joyful as they can be.
TL;DR: Biggest Takeaways and Reflections for Caregivers
Choose Sanity: Unsustainable routines rupture family systems, and are not sustainable. Prioritize choices that take into consideration all factors at play: yourself, your spouse, your family, and your aging parent.
Transitions: Be aware that a major life change can augment memory loss and symptoms of anxiety, particularly in someone who has a history of experiencing anxiety symptoms. Mental health and cognitive decline often co-exist, impact one another, and are augmented by transitions.
Structure and Predictability: Implement structure and boundaries in visits, creating predictability for your parent, your kids, and yourself. Doing so allows everyone to be more emotionally available and grounded in the present moment.
Internal Work: Do the internal work of processing your feelings of guilt, worry, and fear about the past, present, and future. Practice acceptance and a “good enough” mindset. Illicit support of a therapist, coach, or support group.
Remember Joy: Keep in mind that the goal of all of this work is to allow for moments of joy and connection. Don’t let stress and overwhelm muddy this goal.
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Are you interested in being interviewed for Stress & Love? I’m looking to interview individuals who have gone through the sandwich generation, as well as those who are in it as we speak. To clarify: you don’t need to be a primary caregiver to be considered part of the sandwich generation. If you are supporting your parent emotionally, logistically, financially, or otherwise, and you are also navigating raising your own kids, then I would love to hear from you!
And lastly, if you are interested in 1:1 coaching and resources, please reach out to me through my coaching website, Sandwich Support Co, at the link below.

