Sherry Walling & Choosing Self Employment

This is Part 1 of our mini series, “How You Build a Business”

In today’s episode, I get to talk to Dr. Sherry Walling. She’s kicking off our miniseries on how to build a business and she helps us answer a very important question: “Am I ready to start my own business?” Sherry is a fantastic person to talk to and a wealth of knowledge. We talk self-publishing, self-knowledge, podcasting, and much more.

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Intro: Hey everybody and welcome to another episode of How I Built It! In today’s episode, I get to talk to Dr. Sherry Walling. She’s kicking off our miniseries on how to build a business and she helps us answer a very important question: “Am I ready to start my own business?” Sherry is a fantastic person to talk to and a wealth of knowledge. We talk self-publishing, self-knowledge, podcasting, and much more. This is a great episode that we’re going to get into. But first, a word from our sponsors.

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And now…on with the show!

Joe: Hey, everybody, welcome to another episode of How I Built It, the podcast that asks how did you build that? Today my guest is Dr. Sherry Walling. Dr. Sherry, how are you today?

Sherry: I’m good. It’s a mouthful.

Joe: I know. I was like totally on autopilot, so it was like the first thing you say is the first name, so just say that. How are you doing today?

Sherry: I’m doing well. It’s like 30 degrees in Minneapolis, which is like summer vacation weather for us in the middle of winter. It’s been like negative 10, so 30 is like amazing.

Joe: Yeah. Being from the Northeast, I thought I had it pretty bad at like negative one, and then I look at what you guys are going through, so I was grateful to have one 60-degree day last week. I’m like it’s 65 degrees warmer than it’s been. It builds character, I think.

You are going to be talking to us today about mental health, in general, but you have a book coming out. I’m going to bleep the bad word, because I don’t want to throw the explicit warning on this. It’s Keeping Your Beep Together.

Sherry: The Entrepreneur’s Guide to Keeping Your Beep Together: How to run your business without letting it run you.

Joe: There you go. That’s the full name. I really wish I had that up and I had something else up on my other screen. I was kind of perusing the book before this interview, and there’s a lot of great stuff in there. Why don’t we start with who you are and what you do?

Sherry: I’m a clinical psychologist. I have a PhD in clinical psychology. I have traditionally done a lot of work with people who have really high intensity jobs, so I did a lot of my training with folks in the military, and then since built a practice working largely with physicians, attorneys, people who just have sort of high pressure, high stress work.

In the last couple of years, I’ve been doing a podcast with my husband Rob Walling, who’s a serial tech founder. He started a company called HitTail, a company called Drip, and a conference called MicroConf, so he’s like a techie guy.

A couple of years ago, three years ago, actually, we started a podcast together called Zen Founder, where we talk about the mental side, the family side of being an entrepreneur and try to share some good information that’s informed by science as well as our experience to help people’s lives be a little bit easier in the midst of starting and running a business.

Joe: Man, that’s fantastic. I’m so excited to have you on the show, because it’s unlike any guest I’ve really had. I usually talk to developers or entrepreneurs about the things that they’ve created, but mental health, I feel, is something that is being discussed a little bit more but still isn’t given the kind of center stage thought that it should.

I’m definitely going to link your podcast in the show notes. It’s a great show, and you guys cover a lot of … You guys get pretty personal on the show, too, right? It’s probably not easy doing a show like that.

Sherry: You know, it’s interesting. We started out not very personal. We started out a lot of 10 points to beat procrastination, kind of thing. The last year, really the last year-and-a-half, we’ve been through some really significant things in our family including the acquisition of Rob’s company that led us to the move from California to Minneapolis.

Some of the things that we went through as a family, I think, were just super relevant to the people that listen to this show. Then last January, my dad was diagnosed with cancer, so that became a thing that also shaped our lives, but had some impact on our businesses.

We didn’t set out to do a podcast that was about us, but I work with founders, I’m a consultant with founders, I’m a therapist for founders, so I know that those kinds of experiences in your family life definitely have an impact on your business. It just sort of made sense and was authentic for us to begin talking a little bit more about our family life and personal life in the context of what it meant for us as we both run businesses.

Joe: Yeah. Absolutely. You also, kind of in that same vein, you mentioned that you are a clinical psychologist for high stress work, right? I feel like, and, again, this is like all kind of stuff that is from personal experience, but I’ve gotten, you know, “You don’t have a real job. You work for yourself,” or “You’re a freelancer,” and stuff like that.

A lot of people who aren’t in it, kind of view self-employment or freelancing, especially, freelancing has the negative connotation as like easy. They don’t view it as high stress.

Sherry: Yeah. I feel like maybe those folks don’t know what it’s like to be responsible for your own paycheck.

Joe: Right. Especially like if you have kids. I just went full time self-employed in June. I had a three-month-old at home. I don’t know what I was thinking, but it’s working out so far, but it can get very stressful.

Sherry: Yeah. I think there are some really unique stresses that go along with being a freelance or being an entrepreneur, in that you do assume responsibility for the direction of your entire life. That includes the financial responsibility as well as all of the decisions weigh on you.

Again, lots of us have high intensity jobs and stressful jobs, but I think there’s something unique about the entrepreneurial life because it is such a solo enterprise, and you bear all of the weight on your own. Even if you have a spouse that’s all in, and even sometimes if you have a business partner, it’s a uniquely lonely enterprise, which I think from a mental health perspective, has some pretty significant challenges.

Joe: Yeah. Absolutely. You mentioned that before you did this, you were doing military. Is that right?

Sherry: Yeah. I worked in several different VA hospitals in Los Angeles and in Boston.

Joe: Got you. What was the transition like? Did you find it was completely different contexts? Or were there shockingly similar contexts between the two?

Sherry: I think that there are some similarities in the sense that a lot of people who’ve been in combat learn to operate at a level of elevation or a level of stress that feels normal to them, it becomes normal to them.

Seeing a very similar pattern in entrepreneurs who’ve maybe gone through the intensity of a big launch, if they’re in software, for example, and learn to operate at this level of stress, this level of go, go, go, go, go, go, go, and they forget what civilian life is like, or similar to people who are returning from combat, it feels sort of strange to be in civilian life after adjusting to the intensity of a combat zone.

It’s obviously not a perfect parallel, but there are certainly some parallels in the intensity, constant drive, constant rush, constant push that entrepreneurs can find themselves in without kind of this memory of how to live in a more relaxed sustainable way.

Joe: Yeah. Absolutely. Just to add a personal point onto that: I’ve been kind of self-employed in some way, shape, or form since high school. I’ve been full time, I’ve been moonlighting, and one of the big adjustments, and I’m still having trouble with this, is when I’m watching my daughter, like my wife is a night shift nurse, when I’m watching my daughter, I have a hard time not waiting for her to take a nap so I can go do some work, or when I have some downtime, do some work instead of watch TV.

It’s always, when am I going to have time to do that next thing that’s on my plate? Do all parents go through this? Probably not. A lot probably have like a nine-to-five, and they’re very good at separating their work life from their home life, but that’s a transition for me, and I don’t feel like I’m super high stress in my work, but that’s a transition that’s been kind of hard for me, so I can totally see what you’re saying and where you kind of went with the analogy.

Sherry: It’s a sense of being never off.

Joe: Right. Yeah. Exactly. Which could be very stressful. So you have this book that’s kind of the entrepreneur’s guide to making sure you are ready to be an entrepreneur. Again, I have the book in front of me. I was looking at the table of contents. The chapter that jumped out at me the most was chapter three, Self-Knowledge. Because one of the things that I’ll recommend to people who are saying I’m thinking about doing it, is you need to ask, are you ready? Have you thought about this? Is this even something that you want?

A lot of people say working for yourself is a coveted thing, but it’s not for everybody. We can kind of frame all of the questions around that chapter, but branch out as you’d like. First of all, what gave you the idea for the book?

Sherry: We’ve had the podcast. We just recorded episode 151. So there’s a lot of content that Rob and I have been talking about over the years, and that I’ve been talking about at conference presentations and things like that. We wanted to really create something where it was just easy and accessible, where people could get sort of like the take-home bullet points in a fast digestible way where they didn’t have to listen to a hundred and fifty hours of podcasts although, hey, we’re very entertaining.

It also, I think, is a way of just getting that information out there in a way that’s easily accessible. Then I also wanted to really expand, I think, the reach beyond folks who are dedicated podcast listeners. I think podcasting is an amazing medium. It’s been something that I have really enjoyed doing over the last few years, but certainly there’s a larger group of people who are going to pick up a book than will sit and listen to a podcast.

Joe: Nice. Absolutely. When you set out to do the book, did you get advice from anybody? Do you know a lot of published authors who gave you advice? Did you go through the proposal process of finding a publisher? Are you self-publishing? What was kind of the legwork before you set out to actually write the book?

Sherry: Thankfully, I know quite a few authors so was able to talk with them and kind of review the pros and cons of publishing in different ways. I also have a previous life as an academic. I was tenure-track faculty for three years, so a lot of my world has revolved around writing and publishing, mostly in academic journals, which is very different than what this book is, thankfully. It’s a little bit more entertaining.

We decided, and Rob is second author on the book, so we decided that we would self-publish primarily because it allowed us to retain a lot of control and some focus on building our audience, so that was a decision that we made really thinking about what the intention for the book was.

Joe: Got you. That makes sense. Well, first of all, getting published in an academic journal, I know, is not easy or exciting, because I did it in grad school. It’s like I can’t even go back and read this paper that I helped write because it’s so dry. It’s just like very, here are the facts.

Sherry: I would spend like 9 to 12 months writing a paper, especially after you conduct the research, you’ve run your stats, you do the whole process, and I would spend all of this time writing a paper, and maybe like 50 people would read it. I got published in some reasonable journals that have pretty good reach, but then I get on the podcast and after working at it for several years, thousands of people, for better or worse, listen to Rob and I talk every week.

So the reach and the impact in the community is so much greater, which is why I’m really grateful to have the medium, and hopefully now publish the book in a way that will have bigger reach than the 50 people who read my analysis of, I don’t know, combat-related PTSD.

Joe: Yeah. Absolutely. I will say that my paper, which was on, I think the title was Automated Congestion Detection Using Mobile GPS … It’s like traffic detection using phones. I know it was published like in 2008, before it was a thing that happened. I think one person cited my paper in their paper, and it was like I had a party about it. I’m like, “Yes!” Self-publishing is great.

I’ve also gone through the publishing process with a publisher, so that’s a very different thing, too. It’s like you have the proposal and a lot of back-and-forth, but for audience building, especially, I did that because the publisher had audience and was interested in the topic. You get some money up front, but I don’t know how much my audience grew because of it.

As far as self-publishing goes, before we really get into the topic, do you have like a game plan for it as far as, are you going to do print-on-demand? It is only going to be a PDF or an e-book, and things like that?

Sherry: Well, we’re doing a printed book, an audiobook, and the e-book. We’ve gone through Amazon’s CreateSpace, which is the most archaic piece of software that I’ve used since DOS-based e-mail in college. Sorry, Amazon, but your CreateSpace sucks.

Joe: Plus one on that.

Sherry: Yeah. I’m really, really, this is the best we have? Yeah, so we have the printed version, which I am looking at a proof right now. If feels good in my hands, I’ve gotta say. Then we’ll have the e-book. Then I recorded the audiobook, which I think for the podcast listeners who are used to listening to my voice, that will feel familiar and hoping that it’s not irritating to everyone who’s not used to listening to my voice.

Joe: Was it different narrating the book as opposed to actually doing the podcast? Do you have a more formal cadence to the audiobook? Or is it still that casual conversation? Just out of curiosity.

Sherry: I really worked hard for it to sound more casual, because I think audiobooks, especially when they are read by the author, if they’re read in a way that feels really rote and detached, I think something is really lost. There’s definitely some parts in the audiobook where I just sort of go on a tangent and riff a little bit, and I’m like, “Okay, audiobook listeners … ”

I’ve really wanted it to be more conversational. Again, we’ll see if that feels good to the listener once we get some feedback and reviews about it. I will tell you that I recorded the audiobook before we finalized the printed version of the book, and that was super valuable, because, of course, I’ve read it over and over, I wrote it, I’ve edited it, I’ve spent a lot of time with this material, but reading it out loud, there were just things that, “Oh, that came out funny,” or “That’s not what I meant,” so it was a really nice final process of editing the book, actually, to read it out loud, record the audiobook, and then go back and actually make some changes to the printed text, where it just didn’t sound right as I read it out loud.

Joe: I think that’s really great advice for any kind of long form writing, especially. Some advice I got from an English teacher in school was like, “Read it out loud and see how it sounds.” I did that with a newsletter I got, where somebody said, “This app has become my wife and I’s favorite,” and I’m like you did not read this out loud, because that’s not grammatically correct, and it sounds super weird. Like my wife and I’s? I think that’s great advice in general, because you really do get to see, or hear, how it sounds to the reader. That’s fantastic. Then another bonus of self-publishing is, you mentioned you’re going to get feedback from readers, listeners; you can iterate more quickly on a self-published book, right?

Sherry: Absolutely. I mean, I own the audio files. If people are like, “What happened to you in chapter five?”, I can go back and fix that. Or I can go back and make modifications that I feel like need to be made once the products have had some life to them.

Joe: Right. Right. On that same token, I’m very grateful for my publisher, but my book is three, almost four years old, at this point. If I want to make updates to it, they don’t want to do a version two, so now I have to go through getting the rights back so I can update and distribute it if I want to.

I’m very grateful for my publisher, and it’s Peachpit, and I learned how to make websites from Peachpit, so I’m honored that they published my book, but a few years down the line, especially with tech books, it’s out of date. Now this is another hurdle I have to go through if I want to put out the book again. Oh, yeah. Go ahead.

Sherry: I was going to say, I think if there’s a second or third book in my future, I would definitely consider going through a publisher just to have that experience. I also do swim in the academic circles still a little bit, and there is still a cache to being published by a publisher and having gone through that review process.

I don’t diminish that process at all. I think it’s really important, but I think for this one, we wanted to get this out to our scrappy podcast audience. So it feels good to have self-published this one and, again, I would totally consider going through a publisher the next round.

Joe: Totally. It comes down to like what you’ve been saying, it all depends on what you want. I will say having that book officially published is what helped, I feel, that helped me land my job at Crowd Favorite, or at least Karim, the CEO of Crowd Favorite and a good friend and my former boss, was very happy that I was able to publish that book, because it was something that we could tell clients.

There is a cache to being published, and it really all depends on what your goal is. If you’re going to iterate quickly, self-publishing is definitely the way to go.

We’re like 20 minutes into this conversation. Let’s talk about the subject matter. I’ll say, like, Sherry, you’re very easy to talk to, which is probably a great quality to have in a clinical psychologist, so this is why we’re 20 minutes in and we haven’t even talked about the book. So this is going to be a longer-than-normal episode.

Sherry: Soon I’m going to get you talking about your mother.

Joe: I know. I know. I’m an Italian, so I’m very attached to my mother, of course. Let’s talk about chapter three, Self Knowledge. Maybe you can give us like a quick overview of what that chapter covers and kind of your goal for writing that chapter. Does that sound good?

Sherry: Yeah. So really my goal was not to help people assess whether or not they’re ready to be an entrepreneur. I think my goal is generally to assume that lots of different kinds of people can be successful as an entrepreneur, especially if you have like a really clear sense of what your strengths and weaknesses are and know how to plan around them.

In this chapter, we talk about a couple of different continuums. One is introversion/extroversion, which lots of us talk about all the time. One that we talked about is growth mindset versus fixed mindset. The last one that we talk about is chaos versus rigidity.

We think about these continuums as different ways of kind of organizing a personality, and no matter if you are an introvert or an extrovert, or you tend toward the more rigid, or you tend toward the more chaotic, there’s a place for you in the entrepreneurial world, but being able to tell the truth about what you’re good at and what your liabilities are is really the point of self-knowledge.

Joe: I mean, that’s a huge step in being successful, like being a successful entrepreneur, like knowing … Like I know, for example, that I would like to be more rigid than I am, but I have like 14 notebooks on my desk right now with different notes in each of them. As long as I understand that that’s the way I work and at some point during my day I organize all of those into a single list or a group of notes, that’ll help me stay on track. I’ll focus less on I need to be more rigid and more on focusing on the core of my business. Is that accurate?

Sherry: Absolutely. I think those of us who tend to be more flexible and more kind of big-picture thinking, more outside the box, those are great entrepreneurial skills, but it does mean we probably need to support our business with either the help of a Type A person who can come in and sort of keep us going in the right direction at the right time, or there’s certainly software that can help supplement, too.

I know just in working with you in organizing the podcast, you use Calendly, you have notes that are set up, so you have this system that’s in place that helps you provide structure to people who come on your podcast as guests, so you don’t bear the burden of like remembering, “Oh, I need to tell Sherry that we record this way,” and “I need to do this,” and “I need to do that.”

As an out-of-the-box sort of more chaotic person, you’re not going to be good at those things, so you can create systems that do them for you.

Joe: Right. Right. That came about because my first few guests, I’m like, “Oh, yeah, I forgot to tell you this,” and I’m like I should stop forgetting to tell my guests things.

Moving to the personality stuff, I know a lot of … At least a lot of people in the WordPress space, which is where the core of my audience is, are introverts, either self-identified or otherwise. I am super duper extroverted. What kind of effects does that have on a business? What should somebody think about if they’re introverted versus extroverted?

Sherry: For people who tend to be extroverts, it’s such a great super power, especially as you’re in sales or marketing or just letting people know about what you’re passionate about and what you’re doing in your business, but it can provide sometimes some blind spots, particularly in listening and observing.

If you want to be an extrovert, or if you are an extrovert, rather, like you don’t struggle to fill space. You don’t struggle to facilitate or host a conversation, but it might be a little bit harder for you to listen well. Listening, of course, is super important in a business. You’ve gotta listen to your clients, you’ve gotta listen to feedback from people that work for you and with you.

If you are often the center stage person, it’s really helpful to be super intentional about getting feedback and really listening to that feedback well. I also think it can be easy to kind of neglect your inner life if you’re an extrovert. It’s not that extroverts aren’t deep people, they certainly can be, and they certainly are, but to really take time to think about like, how am I doing? What’s going well in my life? What’s my emotional life like these days? That self-reflection, internalization, can be a little bit more challenging for extroverts, but it’s still really important for them.

Joe: Got you. Well, I was nodding my head a lot during that, so I’m definitely relating to what you’re saying. As far as introverts go, first of all, I’ll say this: People often equate introversion with antisocial, but that’s not really the case, right?

Sherry: Psychologically speaking, those are super super different things. Antisocial is like, antisocial personality disorder, which is essentially someone who lacks the neurological capacity for empathy. Like they tend to be highly represented in the clinical, or like in the prison population. Don’t use antisocial when you mean not very socially oriented, because antisocial is a very different thing.

Joe: Got you. Awesome. I’m really glad you clarified that. I meant it more colloquially as in people tend to shy away from social events. Even that’s not necessarily the case for introverts. Introverts, I’m friends with many, whom I’ve met at conferences.

Sherry: Yeah. I was at this speakers dinner for Converted, which is, Lee Page hosted this Converted Conference, which is like heavy marketers. Ezra Firestone was there. Anyway, Derek Hepburn was there, Rob was the speaker, really like gregarious, on-stage people who you would think would be like the extroverted extroverts. As we went around the table and talked about this, like the vast majority of them identified as introverts.

Being an introvert has really nothing to do with how well you can hold a conversation or how well you can present on stage. Being an introvert has to do with how you restore your level of energy, and usually that’s sort of the way of recharging your personal batteries happens by yourself. Your inner world is important. The quality of what happens inside of you is of great interest and importance to you if you’re an introvert.

Joe: Got you. That makes sense. My wife, who is an introvert, and I differ in that way. She values her alone time. I told her the last time I went to WordCamp US I walked in, there were like 2000 people. I knew many of them. I was totally energized by that experience.

Sherry: Kid in a candy store.

Joe: Yeah, exactly. That’s fantastic. What other highlights from this chapter would you like to mention here? Again, we’re just kind of getting a taste of one chapter of a book, and I’m already really excited to read the rest of it, because I love everything you’re saying right now.

Sherry: I think the take home in this chapter is like … is really no matter how you’re built as a person, there are some super powers intrinsic in that. If you’re a really introverted person, you have some amazing skills in your ability to observe and read situations, because you’re not busy talking; you’re often busy watching. Understanding what super powers you have based on just who you are in the world is really great in terms of identifying and cultivating your own strengths.

Then we also want to tell the truth about the shadow side, or the liabilities that go along with being an introvert, for example, and the things that you might have to intentionally either make yourself do, or hire out, or plan around so that they don’t become weaknesses that damage your business.

Self-knowledge is just about self-reflection. What am I good at? What am I not good at? And really being honest with yourself, which is not always easy to do. I think some of us are just naturally pretty barricaded against that kind of honest self-assessment.

Joe: Yeah. Absolutely. That’s fantastic. I know we’re kind of coming up on time already, but there’s more I’d like to talk about. What’s your favorite part of the book, would you say?

Sherry: Oh, that’s like choosing a favorite child.

Joe: I know. This is like out of left field, too. I sent show notes, and I didn’t prep you for this question.

Sherry: No, that’s okay. There’s a chapter that is kind of a deep dive into mental health where we talk about depression. The chapter’s called Coming Undone. I feel pretty proud of that, because I do feel like it’s a unique voice that I offer to the entrepreneurial world that many other people can’t offer with the same quality and depth as somebody who’s spent years and years and years training as a psychologist.

I don’t know. I feel like lame saying this, but I’m proud of this book. There’s a lot of me in here, so I’m already sort of bolstering myself from the negative feedback that I know will come. That’s part of putting something out there in the world. Not everyone’s going to love it, and that’s okay, but this represents some hard work that I want to offer to the community, and I hope it’s helpful.

Joe: Absolutely. Maybe we can parcel that out a little bit. Before we started recording, I told you about an experience I had on the day of this recording, which was not based on any of my work at all. It was about a pretty strong opinion about sports fans from a particular area and all of the negativity I got from that, and that wasn’t even something that I was deeply attached to, but I felt it, because it came pretty hard.

So what advice do you have for somebody who’s totally putting themselves out there? If you work for somebody, you’re probably doing somebody else’s work, and while you might enjoy the work you’re doing, I’m not saying you don’t enjoy that work, but as an entrepreneur, it’s all you. It’s your idea, it’s your execution. How do you bolster yourself from the inevitable negative feedback that will come at you?

Sherry: I think we have to choose our spheres of deep feedback. Rob has read the book. He wrote it with me. If he has feedback, I’m going to listen. There are circle of friends, there’s a circle of other entrepreneurs who I share my ideas with, and whatever feedback they have say, positive or negative, I really listen.

Then there’s, like my Twitter followers, or people I’m with on Facebook, or people who have done consulting with me, and their perspective matters to me, but it’s at this other level on the concentric circles of my selfhood. They don’t get to have this direct route to my heart. I’m going to filter a little bit more.

So we have to kind of choose how much we let people in and be willing to dismiss feedback, or at least give it less weight from certain people.

I think the other thing that I am just talking to myself a lot about is that I did my best to provide something valuable. Again, not everyone’s going to like it, but I did my best to provide something valuable, so I’m just going to say that over and over to myself, especially when I’m confronted with negative feedback.

There are certainly things that could be better about the book, and I hope my next book is better. I hope my podcast continues to get better. I’m oriented towards growing, but I’m not going to spend a lot of time thinking about feedback that doesn’t help me grow.

Joe: I think that’s great advice, and kind of based on what you’re saying there, something that I told myself this morning as I’m reading all of these mean tweets is that tweet is a blip on that person’s radar. They’re going to make that comment and then move on with their life, and I should do the same. I should read it and move on.

If I think it’s going to be helpful to me, then I will take it, but kind of taking all of these five seconds or less that these people took to write the tweet to heart and really carry it with me, is not healthy and not helpful, either.

Sherry: Yeah. Your response shouldn’t be greater than the energy that was put into the feedback.

Joe: Man, I love that. That’s probably going to be the quote that I use to promote this episode.

Sherry: Quotable.

Joe: Awesome. As we come up to the end here, I want to ask … We talked a lot about the content of the book and the book writing process. Let’s look at post launch. What are your plans for the future of this book, of followup books, things like that? What are you going to do after the book comes out?

Sherry: After the book comes out, I hope I get the opportunity to talk about it a lot and share it with people. I’m trying to leave space in my life and world for some conference speaking and being on podcasts and hopefully talking about the book as much as people will be willing to listen.

Rob and I are also hatching a plan for a course that we’re going to do, a video course, that’s going to be related to family life, particularly how to keep peace with your significant other while you’re launching a business.

I’m working on writing the content for that right now and we’ll be recording in early February. I think we are wanting to work together to provide some things that are more accessible to people than, again, like hours of podcast content or coming to a conference or something like that.

Joe: That’s great. The course that you mentioned, is that based on … I know you’re doing these events called ZenTribes. I didn’t have this written down, but I’m ad libbing a little bit. One was specifically about being an entrepreneur and being the spouse of an entrepreneur, is that right?

Sherry: Right. We did a couples retreat in September with a group of folks where we really did a deep dive into how do you keep your relationship healthy under the stress of being an entrepreneur, which I think was one of the things that I found most valuable and am most proud of in terms of last year what I worked on.

Then we put together a ZenTribe for families that we call Founder Families, but to be honest, we never launched it, because we could never find a time when we could get people and their significant others together in a group. We were looking at evening times. People are busy, so that’s why the course seemed like a better way to do that. It’s kind of a do-it-yourself-at-home kind of course.

Joe: Got you. I know the last kind of one that you announced was bad timing for me. I had considered it, though, because the things that you talk about, the kind of camaraderie that you have with the other people in these groups is super valuable. Plus I know that you’re heavily involved with the Heskeths, and they’re like the parents that I want to grow up to be.

Sherry: They’re amazing.

Joe: I’ve told them that before, so they’re not hearing this for the first time. That sounds fantastic. For the last question, I know you gave us a lot of great advice, but do you have any trade secrets for us?

Sherry: I think the trade secret that I’ve been thinking about a lot for mental health is to play long ball, to really not get tangled in the day-to-day ups and downs, but to play long ball with your business and long ball with your life.

Joe: I like that. Have a bad day here, have a good day there, but over the long term … It’s like investing in stocks. You don’t want to live and die by a single day of trading. Cool. Very cool.

Well, Dr. Walling, thank you so much for your time today. I really appreciate it. Where can people find you?

Sherry: I’m at All the things that we are scheming and dreaming are there, and we love hearing from people who are thinking about mental health, so people can absolutely find us there. I’m via email.

Joe: Awesome. I will link all of that in the show notes for this episode, which you can find over at Sherry, thank you so much for your time. Thanks to everybody out there listening. Until next time, get out there and build something.

Outro: What a great conversation – thanks again to Sherry for joining me and for kicking off this series. Definitely check out here book. It’s in the show notes and it’s $3.99 on the Kindle.

And Thanks again to our sponsors – make sure to check out Liquid Web for managed WordPress hosting. I use them on all of my important sites – they are that good! They are at They’ll give you 50% off your first 2 months just for being a listener! If you want to save your clients (or yourself) money through recovering abandoned carts, check out jilt. They are over at And finally, if you want to build incredible websites at a fraction of the time and cost, check out Beaver Builder. I use it and I love it. They are over at

For all of the show notes, head over to If you like the show, head over to Apple Podcasts and leaving us a rating and review. It helps people discover us! Finally, last week I published my brand-new Patreon page. It offers a lot better rewards, and great goals, and I’m really doubling down on it. So if you like the show and what to support it directly, head over to You can support the show for as little as $1/month.

Continuing our series next week, I’m talking to Sara Dunn about niching down. She’s been very transparent about her process and I’m so excited to get her on the show to talk about the decision making process. Hopefully it will help you too.

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