Finding Hope in Grief as a Creator with Sherry Walling

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We all deal with grief. It could be the loss of a loved one. Maybe the loss of a job. Or the feeling that you’ve lost control of your life or your business. Throughout the pandemic, many of us experience grief in one way, shape, or form — and Dr. Sherry Walling is no different. But she decided to write about her grief. First, it was just for her. Then she shared it. Then she decided that her writings could help countless people and turned them into a book. I’m grateful she took the time to talk to us today. We get into how grief affects us, what creators can do, and the book writing process.

Top Takeaways:

  • When you experience grief, writing is a helpful exercise. It helps you process your feelings, but it also allows you to write a new reality for yourself.
  • Life doesn’t necessarily stop, but you have more space and time than you think. It’s OK to slow down for a while.
  • Reconnecting to hope happens in tiny moments, like getting up, hugging a loved one, and even making a meal. Listen to your body and do what is best for you.

Show Notes:


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Joe Casabona: We all deal with grief. It could be loss of a loved one, maybe loss of a job, or the feeling that you’ve lost control of your life or your business. Throughout the pandemic, many of us experienced grief in one way shape or form.

Dr. Sherry Walling is no different, but she decided to write about her grief. First, it was just for her, then she shared it. Then she decided that her writing could help countless people and turned those writings into a book. I am grateful she took the time to talk to us today.

We get into how grief affects us, what creators can do, and the book writing process. There are a lot of helpful things for a lot of people. I tried to put this interview through the lens of creators who can experience isolation and burnout, but really Sherry’s own experiences shed a lot of light on how we can work through our grief.

And I do just want to mention a little bit of a trigger warning here. This episode does talk about death, loss, and suicide. So keep that in mind as you listen on. You can find Sherry’s book and all of the show notes we talk about today over at And I want to end by saying that this is a hopeful conversation. So I hope you really enjoy it.

I also want to thank our sponsors for this episode: MOFT, Nexcess, and LearnDash. You’ll hear about them later on in the show. But for now, let’s get to the intro and then the interview.

[00:02:57] <music>

Intro: Hey everybody, and welcome to How I Built It, the podcast that helps small business owners create engaging content that drives sales. Each week I talk about how you can build good content faster to increase revenue and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

[00:03:19] <music>

Joe Casabona: All right, welcome to Episode 279. Thanks so much for joining us. I’m really excited to have a repeat guest on the show today, Dr. Sherry Walling. We’re gonna be talking about her new book. According to my notes, because I’m bad at what I do, it’s called Touching Two Worlds: A Guide for Finding Hope in the Landscape of Loss. I’m so excited. Sherry, how are you today?

Sherry Walling: I’m great. It’s great to be with you. Thanks for inviting me back on.

Joe Casabona: Yes, my pleasure. A little behind-the-scenes stuff. I get like a bevy of bad pitches and Sherry reached out with the most perfect pitch. So if you want to learn how to… and I mean, it helps that we know each other, but it also helps that she knows the audience. And this is a really good topic too. I was-

Sherry Walling: I know the audience because I know you; I know you because I know the audience. Right? They go hand in hand.

Joe Casabona: Yeah, absolutely. You know, a little bit of that legwork goes a long way. So you have a new book out. The last time you were on the show I believe you were talking about your previous book, which again, the name is escaping me because I’m apparently bad at what I do.

Sherry Walling: The Entrepreneur’s Guide to Keeping Your Sh*t Together.

Joe Casabona: Yes, that’s right. And I gave away a couple of copies of that book if I recall correctly.

Sherry Walling: You did. Thank you.

Joe Casabona: Yeah. This one is a different tone, kind of totally different topic. What led you to write this book?

Sherry Walling: Well, I wrote this book because a bunch of really terrible things happened. This book is about grief and about how people find their way through grief. And I started writing a few days after my dad was diagnosed with esophageal cancer. I didn’t start writing for the intention of writing a book that I would sell and release. I was writing because it was what was helpful to me when I was in the midst of difficult thing.

So my dad was diagnosed with cancer, he died 18 months after his diagnosis. And right along that same kind of parallel process, my brother who was in his early 30s at the time really took a deep dive in his own addiction and depression, and he died by suicide six months after my dad. So it was these two people I loved who were really becoming unraveled and then eventually dying from these different illnesses.

And writing was my kind of way of processing and then sort of leaving little breadcrumbs behind me for people who may have to go through similar experiences.

Joe Casabona: That’s a really tough thing to go through. I’ve experienced both of those things not close to each other. And certainly, I mean, not one of my siblings. You know, my mother-in-law actually as we record this recently passed away after a very long battle with ovarian cancer.

And writing is a good outlet for a few reasons because you’re capturing kind of how you feel in the moment, which I think is you’re in a totally different mindset than probably the mindset you’re most… I don’t want to say normally, but most commonly in.

And like you said, it can be helpful to people down the road, right? Because it feels a little bit hopeless. For us, it was seven years. And I told my wife this: I felt like every call or every text was the like, “Is this it text?”, which would be a terrible way to tell somebody. “So is this a call?” And kind of capturing those feelings in the moment are helpful to reflect on and get some perspective.

Sherry Walling: I think too you’re writing a new reality for yourself, right? I lived in a reality in which I was a person who had a mother and a father and two brothers. And that was all I knew myself to be. And as my reality was shifting, that I am a person who has a living mother and a living brother and a dead father and a dead brother, it’s like I’m telling a new story.

And the writing is helpful because it helps us to transition into this new reality. So I recommend writing as a tool for lots and lots of reasons. But I think mostly because we’re sort of trying to anchor or wrap our minds around a new version of ourselves, a new reality in our lives.

Joe Casabona: That’s such a great point, too. I mean, over the last two years, people have gone through a lot of different transformations. There’s the grief. There’s also… I don’t know if you were at WordCamp US 2019 that was-

Sherry Walling: The one in St. Louis?

Joe Casabona: Yeah.

Sherry Walling: Mm-hmm.

Joe Casabona: That was my last big conference before the pandemic and I came home to getting smacked in the face with a positive pregnancy test. So since the pandemic started, we’ve had two more kids. So things look very different. And then we’ve experienced grief.

I was telling you in the green room, I guess, that I sought therapy for the first time ever during the pandemic because I didn’t feel like I could be an effective father. I like wasn’t coping well because my wife still had to go to work. She was a nurse, and still is a nurse. So it was me kind of stay-at-home dad and dealing with the stress of trying to be an entrepreneur, always being home, I’m an extrovert, and then trying to take care of small kids. So there was a lot of things going on.

You’re also a very busy person, right? I will put it that way. You are working on a lot of different projects and you have a family as well. So life doesn’t stop when terrible things happen to you. And I think you touch on this in the book, right? Like, how does one deal with the world continuing when it feels like yours needs to stand still?

Sherry Walling: Well, it’s a bit of a Both And because it does sort of stop, and then it doesn’t, right? There are experiences that we have. Like, you know, having a new child or losing your mother-in-law. These are life-altering moments. And it does take your breath away. And you do have a paternity leave or bereavement leave or there’s some acknowledgment that you’re departing from the patterns that you’ve been in, and you’re making new patterns, a new version of your life to go along with this new person or the loss of the person.

So in that way, I think it’s important to say like, yeah, your life does stop, like pause. There’s a big departure from what was before to what is going to be in the future. But the other things don’t stop. The dog still needs to be fed, the library books still need to be returned. Apparently, I still need to pay invoices and collect money from my clients. Like there’s still work to be done.

And I think, for me, it’s been important to navigate the logistics of life in a very gentle way, especially when you’re in the throes of grief. Like many of the things that I thought needed to happen in a timely manner turns out there’s not that much urgency. So I’ve learned about the value of giving more space and time and being a little bit more gentle even though there’s still that part of me that’s like a hard-driving, ambitious, motivated person.

And I really want to do things. I really want to go to that event or write that book or do that thing. It’s okay to turn it down for a while and it’s okay to have these moments of pause to honor that the world did stop as you knew it.

Joe Casabona: That’s something that really resonates with me there is basically the day my mother-in-law died, I signed a five-figure contract for like a rush video deal. And I’m meeting with the client and I’m like, “Yeah, like, I have a funeral this weekend, but I’ll be able to…” And they’re like, “Take the time.” And I’m like, “I can do this, though.” I was a little glibly like, you know, it wasn’t my mom, which is weird because I was very close to my mother-in-law. But it’s almost like I wanted to keep pushing through almost like feel normal, or you know, kind of keep doing this thing that I had control over.

Sherry Walling: I think that’s super normal. I have a few instances of doing very similar things. Like sitting by my dad when he’s receiving chemo. You know, you’re kind of there all day. So he’s getting chemo and I’m like working on a book proposal or drafting a speaking pitch.

It’s actually why my book is called Touching Two Worlds because I’m trying to grapple with what it feels like to be so alive and be in a really beautiful phase of my life with young kids who are flourishing, with a career that I’m just in love with, like think is amazing, and then also be challenged to be totally present to death and grief and loss and the unraveling of things.

So how can you go in one day from the heavy reality of death to this incredible opportunity that you’re super excited about? So I don’t pathologize what you did, Joe, because I relate to it. And I do think that all of us are trying to just be big enough and wide enough to hold the both ends of the spectrum.

Joe Casabona: Yeah, absolutely. And to that point, you’re a trauma psychologist, right?

Sherry Walling: Mm-hmm. Yeah.

Joe Casabona: I guess I hope this isn’t grief now, but you know, there’s always the question of does the barber cut his own hair? You have a deeper understanding of trauma and kind of how people process things and most people. Does that weigh on you at all? Kind of do you recognize that you’re trying to process your own… you’re kind of trying to read the label from inside the bottle sort of thing?

Sherry Walling: I was grateful for my training when all of this was happening because I think I had more language to give to what I was experiencing and I had a little bit of a framework. Because I’ve seen so many people recover from really, really painful things, I think I knew that I would recover. Like I wasn’t gonna get stuck in the depths of my grief, or, as it relates to my brother’s death, the depth of that very traumatic experience.

I had this kind of deep assurance that I would find my way out because I’ve lived alongside so many of my clients as they’ve found their way out. But also, I had a therapist and I saw a physician and I sort of did all of the things that need doing when your life is dismantling. And I don’t for a second think that I get a pass on any of the pain or the experiencing of it or the need for help. So thankfully I had enough humility to not pretend for a moment that I was going to heal myself and then write a book about it. Like that’s not what this book is about.

Joe Casabona: Gotcha. That makes perfect sense. So let’s move on to… I mean, the title of your book is not just about the hard part, the heavy part. It’s about finding hope, right? Because it can feel hopeless. Again, drawing on my own experience here, seven years we feel like… I felt like when the moment came, like, “Oh, well, we already kind of… we’ve been grieving the loss without experiencing the loss. Which obviously is not the case, because we could still go talk to her up until we lost her. So it could feel hopeless.

So let’s talk about let’s say the subtitle of your book: Finding Hope in the Landscape of Loss. Why don’t you give us the kind of 10,000-foot overview first, and then we can kind of dig in?

Sherry Walling: Yeah, I wish that I could say, “Okay, I’ve got a three part plan for you, Joe. If you’re looking for hope and loss, do these three things. First, is this phase and then is that, then is that.” That was not my experience, nor the experience of anybody that I know really, truly.

I do think that most of finding equilibrium or refunding or reconnecting to hope following significant loss happens in very little moments. So it’s every day that you get up, every day you take a shower, every day you re-engage your work or talk to your friends. It’s sort of these very small step-by-step moments.

And I think that part of writing the book was to call some of them out. One of the things was really, really helpful to me in reconnecting with my own aliveness was really being in my body. Like having a very consistent yoga practice, training as a circus aerialist. Finding ways for me to daily feel the beating of my own heart, feeling the breath in my lungs, feeling the strength of my arms.

Similarly, one of the things that was really healing was making sure that I was really intentional about hugging my children, which sounds super, super simple. I didn’t need a PhD to figure that out. But my kids were experiencing death in their family and I was experiencing death.

And death is, you know, often depicted as this like shadowy figure who’s lurking in the back corner. And it does kind of feel like that because once death enters your life, you’re very aware of it. And one of the best ways that I can think of to be resistant to that feeling is to celebrate the warmth and the connection and the aliveness of like bodies and a hug. So I would spend a lot of time just watching TV and holding my kids. And that was very, very hopeful to me.

Joe Casabona: I mean, you know, I’m a parent of three small children and that certainly helped. I know it helped my wife too in multiple cases, right? Because every day we’re getting up, so we have those little moments of “well, we got to get Teresa off to school. Oh, Louis needs a new diaper or whatever.” And so we have those little moments.

But then having a good support system and having people around us to let us know that, Hey, we’re not alone and we can celebrate those connections that we have. I guess that’s another thing I wanted to kind of touch on. Because again, in maybe my darkest moment of the pandemic when I had a… Again, I said this in the greenroom. I’m not calling it a panic attack but I was kind of like crying on the floor a little bit and my three-year-old had to bring me a towel and water and it’s like, “It’s okay, daddy.” And I was like, “This should be the opposite.”

But I didn’t feel like I had that support system. We felt very alone because again, my mother-in-law was… we were being very cautious at the time. We didn’t want to expose her to anything. And my father-in-law was taking care of her full time. So it was kind of just us, and the kids and I was home the whole time. And it was really hard.

Sherry Walling: And your wife’s at work as a nurse in a very scary medical crisis. That’s super challenging and isolating circumstance that you find yourself in.

Joe Casabona: So having any kind of support system or any… I just found really helpful. Like I said, I saw that support system for me at that time. So it wasn’t like dumping on my wife all day after she got home from like, yeah, nine people are dead from COVID, or whatever, was to seek therapy. And I talked to a toddler specialist so that she could help me with the parenting stuff.

Sherry Walling: Work out this toddler.

Joe Casabona: And it was usually helpful. I’ll share one story. I’ll share one story. Because I don’t know what a good benchmark is for children until you have children. But I was reading a story to my daughter called How to Train Your Dragon to Say No, or how to teach your dragon how to say no or to hear no.

And I was like, “Oh, [Degree?] couldn’t go outside because it was raining.” And Teresa was like, “Why doesn’t he just get an umbrella.” And I like snapped at her. Like, “Just let me read the story.” And my therapist was like, you know, this is actually a really good problem solving and troubleshooting for a three-year-old and you should really encourage that.” And I’m like, “Good to know. Don’t do that.” So having someone there was super helpful, I guess, is that long story.

Sherry Walling: I think we all need a coach sometimes. We all need a like, person that can be a sounding board, to our inner thoughts. I think that’s a hard thing about being an adult. Like when you’re in a kid… this works for better for worse. But when you’re a kid, you have all kinds of feedback, right? You get grades, you get accolades, you win your sports races. There’s all this like feedback loop, whether you want it or not, that’s telling you if you’re doing a good job or not.

And as adults, depending on where we are in our lives, especially as entrepreneurs, we just don’t have that. There’s no supervisor that’s like, “Joe, just giving you a 4.5 out of 5 on the parenting today.” There’s no overseer.

So I think sometimes it’s helpful to have someone that you can be like, “This is what happened. This is what I did. What do you think?” especially when we’re in unknown terrain, as we all were in the pandemic, but especially you as an extrovert, I get home with very little children, you know, like you are in unknown terrain. I was in unknown terrain when I’m like, “Everybody’s dead.” You’re like, “What do I do? How do I talk about it?”

[00:24:07] <music>

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[00:25:13] <music>

Joe Casabona: To bring it back to you, this is not like the Joe therapy session, but this is a really important topic. You mentioned that writing was a helpful exercise. So we’ll wrap up kind of with what led you to write this book and then kind of who this book is for before moving on to a great article that you have in Fortune.

So you said you were writing for yourself at first. What led you to decide to get this published? Was it exactly what you were writing that you published? Or was it like, “Well, these are kind of like the notes that I’m going to base the manuscript on.” What was that process like.

Sherry Walling: There are a few things that unfolded. One is I wrote a lot. And I would find myself sending little clips to people, paragraphs, essays, things. So it became evident to me that I did want to share what I was writing and I did feel like it could be helpful to other people who were in the throes of their own chaos or crisis. So that was happening.

I also was invited to give a talk. It’s called a One Last Talk. My friend Philip McKernan hosts these talks where basically, if you had one last talk to give, what would it be? And I don’t know that it was like the one last talk that I’ll give forever for my life but I talked about grief, and thriving and grief. And it was very heavily from the book. And I think the talk felt really powerful. I really loved giving the talk. It felt important.

So it made me sort of wonder like, “I really want to get this message… like there’s a message here that’s important to me that I want to share.” Then I attended a memoir writing workshop that Scribe hosted. Then I had a few other people look at the book as it became more of a book.

And then eventually, I had the opportunity to… You know, I had a book agent who was interested in it. Like months, months, months later, got a publishing deal and they really asked me to go back through all of the essays, and more than make them stories about me to really engage my life and my training as a psychologist.

So the format of the book is such that it’s a story from me and then there’s some kind of like an analysis within an offering. Like, Hey, if you come to the end of your wits as a parent when you’re in the midst of grief, try this,” or, “Hey, this might be helpful.”

So it’s intended not just to be my story, but to be of service to other people. It’s a very broad audience. One of the reasons that I went with a traditional publisher for this book is because most of my work has been in cultivating an audience around entrepreneurs. This book is super relevant to entrepreneurs, but it also has a broader reach. And so working with a publisher hopefully will be helpful in engaging a broader community.

Joe Casabona: That’s kind of the key that publishers are looking for is they want the broader audience because they’re going to put it in bookstores and they want to make sure they’re getting a return on their investment. Which we’ll talk about more in Build Something More. Feels like a super weird time to mention this, but if you want to get that conversation and you want to get all the conversations ad-free, head over to

So you attended a workshop, you had a book agent. This story reminds me a lot of The Last Lecture by Randy Pausch. Have you read that?

Sherry Walling: Mm-hmm. Yeah.

Joe Casabona: That was a very impactful book for me in college. He was a computer scientist, I was a computer scientist, and so feels very, very relevant to the conversation. I’ll link that in the show notes. That’s a really good book, too.

So you mentioned that this is a broader audience. I guess I’ll put it this way. You and I have talked about our experiences with death to experience grief, but you don’t need to experience death to experience grief, right?

Sherry Walling: I think grief is the emotional reaction to loss. And death is the most kind of permanent loss but there are all kinds of losses that many of us experience, whether that’s a divorce. There’s a lot of grief in divorce, the loss of an opportunity, the loss of a job, the loss of a friend. Loss happens all around us all the time.

And I think that death is a great teacher about grief because it’s extreme. But that all of us would benefit from more comfort or just like being more comfortable, I guess as a way to say that, being more comfortable in the landscape of loss because we’re in it all the time, especially in the pandemic.

Joe Casabona: Yeah, absolutely. Talking to creators specifically, but I mean, entrepreneurs as well, I’m certain you’ve seen this is, it’s really easy to get burnt out, right? And maybe that is feeling that a loss of your own time or feeling like a loss of control. I know creators who have gone to a dark place because they felt that burnout.

So, I guess, who should buy this book? Should it be like people who are currently experiencing grief, people who were anticipating—I guess that’s everybody—grief? What are some of the big takeaways for someone who’s reading this book?

Sherry Walling: I think humans should buy this book. I mean, this is the painful part of the process, right? Like, “What is the product market fit for your book?” The book will help anyone become more proficient in the landscape of grief, both understanding grief as they experience it and then kind of what to do about it.

I also think grief can be a very isolating experience. So when my husband read the book in its early phase, he was like, “Wow, I didn’t fully appreciate all that you were going through. And now that I’ve read this book, I understand better what grief does.”

So I think that’s where the book isn’t really limited to people who are currently in grief or anticipating grief. It really has deepening effect for all humans who are longing to be like a little bit more emotionally intelligent.

Joe Casabona: That’s something that I really worried about. Again, my wife is very close to her mother. I was like, “Am I gonna be able to be there?” Both of my parents are still around. The last person I lost was my grandfather, and that was tough. But you expect to lose your grandfather kind of, right?

Sherry Walling: Yeah.

Joe Casabona: Like, you know don’t expect to lose your mother when she’s 54 years old. I mean, that right there, humans should buy this book, because it’s… I think that would have helped. I was told I did okay. And she asked me too. She’s like, “This is your loss too. Are you okay?” And I’m like, “No, I’m fine. I’m good.” To that point it could be very isolating. I didn’t bury my feelings, but I wanted to make sure she was taken care of before I kind of unloaded my feelings.

Sherry Walling: I think it’s a part of life that we all could… It would be better for us as a society collectively, if we were a little bit more adept at grief and grieving well. Because when we don’t create space for grief, we shortchange some of the most important experiences that we have in our lives.

Grief, as we experience it related to death, is kind of like birth, right? We’re only going to do it a few times. And you want to be present for it. You want to be able to fully experience the emotional range and honor that the loss of somebody that we love is… you know, it’s part of love.

Joe Casabona: Yeah, absolutely. To that point, you have a great article in Fortune called How the Great Grief led to the Great Resignation that may be related to your last point about making more space for grief. I’m an elder millennial, but I still have a very boomer view on feelings. Well, I used to. Like pre-pandemic, I was like, “I’m a man. I don’t feel feelings. I just swallow them. I am a man.”

Sherry Walling: “And now I’m crying on the floor.”

Joe Casabona: Yeah, exactly. Right. Now I’m like, “I’m a man, I feel my feelings and I do what I need to do to take care of my family or whatever.” That’s funny. I’m a man, so I’m a man. But I read this article. I really enjoyed it. So what’s the thesis here, how the great grief led to the great resignation?

Sherry Walling: Well, I think probably everyone who’s listening will have heard some conversation about how the nature of work is changing. The great resignation has been one of the terms that’s been thrown around. But, you know, there are lots of different statistics. One is that in November of 2021, just in that one month, 4.5 million people left their jobs.

So 2021 was this year when there was this huge reshuffling in how work happened, so much so that like, many folks are just still having difficulty hiring. But I think that the great resignation, that those shifts in people’s willingness to come to work or to participate in the jobs that they had been doing prior, I think that that’s really driven by grief. And so that’s what I talked about in this article is helping employers and other professionals understand how grief may be at play in all of these transitions that we’re seeing in the world around us.

Joe Casabona: It definitely forces you to face other things in your life, right? Where are you spending the right amount of time? I know, it’s not necessarily quite the same as grief, but kind of the similarities between birth and death.

I quit my job at the agency I was working at when my daughter was three months old for that exact reason. I felt overworked and I didn’t want to miss out on being a dad. And I thought that I’d be able to support my family and spend time with my family if I was self-employed, which knock on woods, three kids, and several years later, it’s still going pretty well.

Sherry Walling: I mean, in a way, these are existential crises, right?

Joe Casabona: Yeah.

Sherry Walling: Birth, death, they get us thinking about the nature of our existence. And if we do that inventory, that internal inventory, and ask the question of is the way I’m spending my time meaningful to me? We asked that question and we say, “No,” we are out the door and that job in a heartbeat. So when grief enters our world, it forces us to ask these questions, but we reevaluate what we’re doing and why we’re doing it.

[00:37:31] <music>

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[00:38:29] <music>

Joe Casabona: There’s a couple of quotes here that really, really stood out to me from this article. And we kind of touched on this. “This exodus from structured work is a symptom of collective grief. We touched on that a little bit.” The one that I think struck me the most is bereaved parents and spouses are nearly twice as likely to die than those not bereaved, and after a year, they’re still 10% more likely to die. Can we elaborate on that a little bit?

Sherry Walling: Yeah.

Joe Casabona: I’ve heard in pop culture like they died from “a broken heart,” quote-unquote. Is that kind of like a gross oversimplification of this quote?

Sherry Walling: Yeah, but it’s actually super accurate. One of the school shooting in Uvalde, one of the teachers that was shot, her husband died of a heart attack within days of her death. So grief is a form of shock, and it can hit people like the way an acute stressor would.

So physiologically it has a significant toll on our bodies. So people are often likely to die of things like heart attacks because they’ve had had such an infusion of stress into their physiological systems that their body is unable to cope with it essentially. So saying that you died of a broken heart is actually not very… it’s pretty accurate. It’s not very much hyperbole.

So there’s also a significant amount of practical stress that goes along with these kinds of losses. So our bodies are in chaos, our lives are in chaos, and it can undo us. You know, it can literally kill us to be in that level of disruption.

Joe Casabona: And during the pandemic, a lot of people experienced that, right? I learned the true meaning of it takes a village to raise a child like during that. Like when you lose that village, it really sets in like how much help you’re getting with children, and especially small children who like need you to do everything for them.

Sherry Walling: Right.

Joe Casabona: Which brings me to my second quote. Again, this one really resonated with me. “During the onset of the pandemic, job demands increased until she (the person you’re talking about) felt overwhelmed and burned out. She could never keep up with her emails. She finally quit in order to spend more time with her daughter.”

Again, this was kind of something that you come to realize during the pandemic, right? Where am I spending my time wisely? Is all of this stress really worth it?

Sherry Walling: And I think especially a lot of parents experienced “I just cannot do both. I cannot be on Zoom in my computer room for eight hours a day, and have my children get their first grade education. Those things cannot happen at the same time.” So of course, a lot of people choose their families. In some ways, that’s good, because of course, we all love and value our families. But in some ways, that’s also like because it feels like the choice you have to make.

So obviously you are an incredibly engaged father, but the way that the pandemic impacted a lot of women was to set women’s vocational and professional equality back years, because often it was women who were leaving their jobs to tend to kids.

Joe Casabona: Yeah, yeah. And I recognize here that my wife and I are in a unique situation where we were perhaps less impacted from two parents with traditional jobs, right?

Sherry Walling: Yeah.

Joe Casabona: Because she works three 12-hour shifts, which means I was able to work at least two days a week. And yes, I feel like maybe my business isn’t where it would be had the pandemic not happened, but I feel like the reason I quit my job to work for myself was to give me the flexibility not for situations like this, but a little bit for situations like these.

Sherry Walling: But when a situation like that arises, you have the margin to be able to adjust your life and your schedule to feed your kids.

Joe Casabona: We also had the strong benefit of not having to do virtual school because our children were just in daycare and there was no curriculum we had to stick to.

Sherry Walling: That was rough for people. There are whole sort of segments of math that one of my kids just didn’t learn. I’m not sure what he was doing on his iPad for, you know, hours and hours a day unsupervised but it wasn’t math it turns out.

Joe Casabona: See, it’s probably best that I didn’t because my fatal flaw is I think I’m smarter than everybody. And if I saw like the common core math teach… like I’d probably argue with the teacher. I’d be like, “No, I got the right answer. This is the right answer.”

Sherry Walling: I feel like you just would have homeschooled if you’d have just been like, “Forget it. I’m just taking this over.”

Joe Casabona: Exactly. Yeah, exactly. We were perhaps in a better situation than most people. Now, let’s end on a potentially happy stat here, right? I’m gonna say potentially because starting a new business is hard. And I don’t think a lot of people realize how hard it is until they’re in it. But a recent study by Intuit QuickBooks found that 17 million Americans will launch a new business in 2022. Very exciting for me, because I think anybody who has the drive to start a business should. What’s your general feeling about that?

Sherry Walling: Oh, I love it. I mean, obviously, I spend my life supporting entrepreneurs. So these are people I love, the people who are like, “I made something. I’m gonna sell it. I’ve got an idea for a great cookie recipe. You know, whatever it is all across the board of entrepreneurship, I think that that level of ingenuity and self-determination and all of the values that drive someone to decide, “I’m going to file this application for my business permit,” those are my people. So those are, you know, the creative classes. It’s who you and I both work with and serve.

And like you’re addressing, I realize it’s hard. And not all of those businesses will be successful but I think they’ll probably be meaningful and they’ll probably be an important part of life for the people who endeavor to make them successful, even if in the end they don’t have, you know, exactly the financial outcome that they would hope for. But I think that’s how the economy is changing, right? All of us are wanting more control, more flexibility, and more ability to make sure that we’re spending our moments in ways that really matter to us.

Joe Casabona: Yeah, absolutely. And if there’s, you know, one good thing that comes out of the pandemic I think it’s that people are realizing what probably many entrepreneurs have already realized, right? Is that time is the only thing you can’t get back. Bill Gates has said it, other entrepreneurs have said it. And so maybe we’re we want to spend our time more wisely.

Sherry Walling: Yeah, absolutely.

Joe Casabona: Dr. Sherry Walling, this has been such an enlightening conversation. Cathartic maybe. Cathartic for me at least. If people want to… First let’s say, if people want to buy your book… I strongly recommend you go out and buy this book because whether you experience it or you’re supporting someone who’s experiencing grief, understanding you’re not alone and that there is hope in loss is, like you said, something everybody should know and understand. So where can people go to get the book?

Sherry Walling: It is at all the major book places. So it is of course on Amazon and it’s also at your local bookstore down the street. So I will just put in the little plug that reviews matter a lot. So if you choose to buy the book, which I hope you will, take an extra minute to leave a review and just a quick little sentence about what you learned from the book or how it served you is very, very helpful and will help me get to another book deal someday, you know?

Joe Casabona: Yeah. I got a couple of bad reviews on my last book because it wasn’t the same as the previous edition. And that dramatically hurt my ranking for a long time.

Sherry Walling: Oh, no!

Joe Casabona: Yeah. So reviews-

Sherry Walling: So if you don’t like the book, don’t worry about it. But if you love the book, please-

Joe Casabona: If you love it, be nice, leave a good review. Awesome. I’ll have that linked up in the show notes as well, which you can find over at If people want to learn more about you, where can they find you?

Sherry Walling: I live on the internet at I’m on Instagram @SherryWalling, and Twitter @Sherrywalling. So I’m pretty easy to find. And I love connecting with folks, so feel free to follow.

Joe Casabona: Are you still doing your own podcast?

Sherry Walling: I am. I should probably plug that. Thanks for the reminder. My podcast is called Zen Founder and we address all issues related to the mental health of entrepreneurs and those who love them. So we’re I don’t know if 330 episodes in. Something like that. So definitely give that a listen as well.

Joe Casabona: Yeah, use that search bar that’s in the app you’re probably listening to right now and you’ll find it. Again, if you want to learn more about the… Now, Sherry now has written a book, both self-published and traditionally published. So we’re going to talk about that for a few minutes in Build Something More, which you can sign up for for 50 bucks a year. That is less than five bucks a month over at You’ll get ad-free extended episodes of the podcast as well as behind-the-scenes to look at the stuff I’m doing. So check it out. Dr. Sherry Walling, thanks so much for joining us today. I really appreciate it.

Sherry Walling: My pleasure. Thanks for having me.

Joe Casabona: My pleasure. And thanks so much to everybody listening. Thanks to our sponsors for this episode. And until next time, get out there and build something.

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