What Are The Real Qualities You Need To Be a Successful Entrepreneur With Special Guest Sherry Walling PhD

Dr. Sherry Walling is a clinical psychologist, speaker, podcaster, best-selling author, yoga teacher, and mental health advocate. Her company, ZenFounder, provides mental wellness resources to leaders and entrepreneurs as they navigate the transition, loss, conflict, or any manner of complex human experience.

She hosts the ZenFounder podcast, which has been called a “must listen” by both Forbes and Entrepreneur Magazine. She is also the host of Mind Curious, a podcast exploring innovations in mental health care and the new science of psychedelics.

Her best-selling book, The Entrepreneur’s Guide to Keeping Your Shit Together, combines the insight and warmth of a therapist with the truth-telling mirth of someone who has been there.

Dr. Walling is an expert in trauma, stress, and burnout and her research has been published in academic journals such as the Journal of Traumatic Stress

Sherry and her husband, Rob, reside in Minneapolis where they spend their time driving their children to music lessons. She has also been known to occasionally perform as a circus aerialist.

Rob Walling the joint founder of Drip and the host of the popular podcast “Start-up For Rest of Us.”

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Intro: Welcome to the WP-Tonic WordPress and SaaS podcast, Jonathan Denwood and his co-host Steven Sauder interview the leading experts in WordPress e-learning and online marketing to help WordPress professionals launch their own SaaS. Take it away, guys.

Steven Sauder: Welcome Back folks to the WP tonic podcast. Today, we have a great guest with us, Dr. Sherry Walling. She is an author, written two books or a notebook soon to come out, too. Keeping Your S**t Together, the entrepreneur’s guide, to keeping your s**t together, and touching two worlds, which is a book about grief, which should be coming out here in July 2022. But we’re really excited to dive into the idea of entrepreneurship and mental health and what that means and what does that look like as an entrepreneur tries to lead a company? I also have my co-host, Jonathan Denwood from WP-Tonic. But Sherry, do you mind just quickly introducing yourself a little bit? Maybe tell us some things you’ve been working on, lately.

Sherry Walling: Yeah, absolutely. It’s great to be here. Thanks for inviting me. So I spend my days talking with entrepreneurs, CEOs about the hard parts of the business. So whether that’s stress, whether that’s sort of managing family life and business life, whether it’s working with relationship challenges within the business, I kind of like to get down and gritty about what’s hard and find innovative creative ways to think differently and work differently. And I, so I come to my world from the background of clinical psychology I spent the first part of my career working with people with really high-intensity jobs. Like people who’ve been deployed to war zones, people who were, working in emergency rooms, things like that. And so the transition to working with entrepreneurs has actually been fairly streamlined, because they’re maybe not people, experiencing life-threatening events in the context of our startups, but, people are certainly experiencing a lot of stress.

Steven Sauder: Thanks. Jonathan, you wanna quick introduce yourself to, the new listeners and viewers.

Jonathan Denwood: Yeah Sure. I’m the founder of WP tonic we build membership and learning platforms for entrepreneurs and organizations looking to utilize the power of e-learning over to you, Steven.

Steven Sauder: Awesome. And just for the record, this is episode 643. And we’re gonna take a quick, break and hear from our sponsors, and then we will dive, right.

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Steven Sauder: All right, coming back, Sherry, it’s really like what you were just saying in that intro, is really fascinating and interesting because I think it’s so easy to put entrepreneurship up on this pedestal and say like, that’s the ideal. And like that’s what a lot of people are trying to do and become and glorify that and glamorize it. And you forget to look at some of the harder aspects of it. I know when I first started, my own company, right, it was all exciting and fun and games. And then all of a sudden, there’s cash flow and payroll and priorities. And, you’re trying to work through all of these different points of stress that are impacting your personal life and your professional life. But as you’ve talked to a bunch of different entrepreneurs, what would you say are some similarities or things that make somebody a successful entrepreneur? And I’m not just talking about like, from like a monetary success standpoint, but from like, like from a mindset or mental space, like what is, what does success look like? I think it’s so easy to say like, oh, well the bottom dollar is how you define success. When in reality success means something far, far greater than that.

Sherry Walling: I mean, I think success looks like somewhat who is finding a lot of meaning in doing something that is interesting and challenging. So I think most entrepreneurs really have very active brains. These are minds that are alive and they’re making something in the world. And I think people who are really successful really content find a balance of how to drive and push, but then also enjoy the benefits of what they’ve built and the freedom and the connections that they have created for themselves.

Jonathan Denwood: Do you feel like a lot of that is trying to figure out how to carve out, time and space to enjoy those benefits? Or how do you start, like going through the process of, maybe separating the stress of work from enjoying life? Like oftentimes that stress of that entrepreneurship impacts that enjoyment that you can have of the thing that you’re actually trying to build. Like, you be really excited about what you’re building, and all of a sudden you find yourself in this space where that excitement just manifests itself in stress, you know?

Sherry Walling: I feel like the people that do this really well integrate their lives pretty well. So, I’m parenting a 15-year-old and 11 year old and that’s pretty stressful sometimes. I wouldn’t say that like my family life is easy and my work life is hard or that’s where the stress comes from. I think there’s stress in all aspects of our life. We can have stress from the health of our bodies. We can have stress from our relationships, even being in a great romantic relationship has its stressful moments and there’s stress from the businesses that we’re building. So I think that the balance of it isn’t to say I do my hard work here, and then I go do my play over here. The best-case scenario is that work feels like play sometimes that we’re getting both enjoyment and challenge from all aspects of our life that are causing us to sort of level up or to keep growing

Steven Sauder: Jonathan over to you.

Jonathan Denwood: Yeah. I think that’s interesting. I’ve got this question about spectrum conditions because obviously, I suffer from, I was gonna say a word that I don’t like using Sherry. I have dyslexia and I’ve noticed, and I was wondering if you’ve noticed this yourself, I’ve read a few studies and a few, that there’s a high proportion of people with spectrum disorder that are entrepreneurs that have dyslexia, mild autism, and, other spectrum conditions. But I think, in the popular media, there’s a misconception about spectrum conditions in general. And maybe you like to comment on that and do you think they are a lot of entrepreneurs that have a kind of spectrum condition?

Sherry Walling: Well, to answer the latter question first, there aren’t a lot of comprehensive research studies looking at the sort of mental health within entrepreneurs. The one that I’m most familiar with was done by Dr. Michael Freeman who, has an appointment at UC San Francisco and his study found that there was a higher prevalence of ADHD and bipolar disorder in entrepreneurs compared to the general population. So those are both, we can sort of understand both of those actually as some spectrum-related disorders. What I think is really interesting. and just a little side note, I don’t love using the word disorder, especially in this context, because I think what I’m about to say is that some of this diversion thinking these are brains that are wired differently, they are functioning on the tails of the normal curve. So if you remember your statistics class, that bell curve, when we’re talking about, a brain that’s looking really different, it’s functioning at the tails either, sometimes in an advantageous way and sometimes in a problematic way. But that diversion thinking that ability to put pieces together, to see patterns to, look outside the box is a superpower for a lot of entrepreneurs.

Of course, it also has its problems, which is why it ends up in books like the DSM with a disorder tag behind it. But when it comes to entrepreneurship, neurodiversity, can be an incredible asset. I dunno if that lines up with your experience, Jonathan, but–

Jonathan Denwood: Well kind of, and doesn’t because I don’t want to downplay the difficulty that a lot of children have that have dyslexia facing American and British education system, nor do I just want to classify those [Inaudible 10:36 ]to apply to children that have dyslexia because you are kind of round peg being tried to be rammed into a square hole and that produces a host of problems. Do you also just do a follow-through question- do you think it also so causes, I have read some studies where it, it does seem to be high propulsion of people that have dyslexia and other conditions, not all entrepreneurs. but is it also a similar situation that ethnic groups can find themselves like, some, some Jewish populations or, or Asian populations have concentrated in certain industries or certain sectors because they’ve been discriminated against and they’ve not been allowed to go into the profession, so they concentrate in entrepreneurship or business ownership. Could it be just that factor?

 s I mean, I think there’s a, how people decide what vocation they choose and how people decide to become an entrepreneur is a pretty complicated process. And one of the predictors of whether you become an entrepreneur is someone who has had a successful business. So if you’re growing up in a community where there are people that are around you, your aunts and uncles, maybe your parents who have been business owners that pathway suddenly becomes much more available to you. And there’s a known track record there’s practical help, which is why we do see entrepreneurship show up in certain communities or within certain families cause hey, there’s a pathway for that.

When I was growing up, I didn’t, I didn’t know anybody who ran a business. My parents were teachers and pastors and they were operating within these very traditional structures. And so, it wasn’t really, until I met my husband, Rob, who is an entrepreneur that, that became like a conversation that we were having because there was no footprint for that. Coming back for a minute to this question about neurodiversity I have worked with so many entrepreneurs who really struggled in school. They dropped out of high school, they took the G E D. Maybe they didn’t finish, a number didn’t go to college. So those traditional pathways towards success that, your, your third-grade teacher talks about and your junior high teacher talks about. They weren’t a good fit for that, they were that square peg in a round hole. This is why for many people who have differently wired brains entrepreneurship becomes, almost like a default choice because graduate school, wasn’t a good option. They didn’t get the grades for that, but they’re brilliant and they can do things with their mind. So they find these alternative outlets for their ability and entrepreneurship is available if you haven’t followed those traditional structures.

Jonathan Denwood: Yeah. Yeah.

Steven Sauder: All right we’re gonna go for our mid-show break here for a quick word from our sponsors, but afterward I’d love to hear Sherry, how you kind of found your path into, this whole segment of kind of looking at entrepreneurship and the mental health of that. So we’ll go for a quick break and we’ll be right back.

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Steven Sauder: All right, coming back. So, Sherry, we were just talking about, people finding their path into entrepreneurship. But I would love to hear how you found your path into looking at, this whole area of entrepreneurship from the mental health kind of, standpoint place.

Sherry Walling: Well, as I mentioned, I have always really loved working with people who are really engaged in their work. So people who find their vocation to be really significant to them and I wanted to help people be healthy at work. But my leaning towards working with entrepreneurs largely began through my husband, my husband Rob is the founder of Drip and MicroComp and, Tiny Seed, and a handful of other things. And so he’s been around this sort of tech startup world for a long time. And so the people in my living room really for all of my adulthood were entrepreneurs, were people who were starting businesses. So they became my friends and I sort of heard some of the struggles that they were having from a mental health perspective and really felt like, oh, there’s nobody talking about this very much. I mean, it certainly wasn’t the conversation that it is now. But very specifically, I came home, I think it was January of 2017. I came home and found my technology engineering-oriented has been crying in his office. And, that’s not a normal occurrence in our family so I was like, what’s going on?

Jonathan Denwood: Yeah, I don’t see Rob crying too much.

Sherry Walling: No, not a big crier Nope, no. and he told me that Aaron Schwartz had died. And I said that’s terrible. Who is Aaron Schwartz? We didn’t know Aaron, but Aaron, was the founder of Reddit and a host of other things. he died by suicide and I think for Rob, he represented sort of the best of this kind of brilliant mind that has so much potential to create and to be a successful entrepreneur, but that, that kind of mind sometimes gets really lost and succumbs to, the pressure or whatever underlying mental health issues are, are lurking there. So it was that day that I said, okay, I’m gonna start talking about this. And so I gave my first talk about entrepreneurship and mental health, at MicroComp and it was super well received, and got lots of questions. And then Rob and I started a podcast about it. I wrote a book about it and that kind of launched the conversation.

So I see my work as really wanting to help entrepreneurs be more attentive and mindful of their own mental health as prevention so that they understand that you can be amazingly sick, successful, and have a business that you really care about, but also have some things lurking inside of you that are hard to work with. And you don’t have to be alone in that situation. There are things we can do to prevent problems, and there are resources and help that can be offered when problems come up.

Steven Sauder: Where does an entrepreneur start or like, you’re, you’re talking about being mindful and aware, like, what are those things? Cause like there’s, there’s normal everyday stress that we feel that’s, for whatever reason. And we can let go of that really easy, but like, how do you start? Like knowing or identifying if there’s like a larger issue that needs to be resolved or something, but how do you train yourself to be more mindful in that?

Sherry Walling:
Yeah. I think it’s really important for people to be attentive to their own cues. So often one of the first things that get disrupted when we’re, sliding off of baseline and starting to not do well, is we see disruption in our sleep, right. We’re waking up at two in the morning, we’re staring at the ceiling, we’re worrying about things. So sleep is an early indicator that maybe something is kind of any inside. Certainly changes in diet or nutrition. Like, you find yourself stuffing your face with chips because you’re just kind of mindlessly, trying to nourish yourself every diet.

Jonathan Denwood: I do it every day sherry.

Sherry Walling: So maybe that’s your baseline so, any significant shifts in our body, our bodies, a really smart indicator that things might not be going well in our brain. Other things that we kind of look for this sort of telling us, Ooh, might not be doing well or the way that we treat people. Like if you’re genuinely like a pretty kind relaxed human, but you find that you’re snapping at people or you’re feeling really frustrated. You’re making fun of your customers something feels off. That’s another good indicator that, Hey, I may need to make an adjustment. I may need some rest. I may need a sounding board. I may need some help. Those kinds of things I think are good early indicators.

I also feel like all entrepreneurs should have a pretty good working knowledge of burnout. What burnout looks like, what the diagnosis is and how it might show up. I think it’s really helpful for entrepreneurs to have a pretty good working understanding of anxiety. And when are motivation and excitement helpful and when is anxiety getting to be too much for us?

Jonathan Denwood: Yeah, I think that’s great, but I think it’s it, it’s a beast that stalks quietly and you are not aware that you’ve got to stage that you’re not functioning that well. And I think that’s one of the problems. I’ve got a passion for WordPress entrepreneurship and education. So when I found my niche, it’s been, quite a joyful couple of years. It’s only taken a long time to get there though. But I’ve got a passion for education and a fascination with IQ. I think not only in America, but also in Western Europe, definitely in the UK education seems to be slightly in crisis, but I dunno if you would, I just have the sense that it is a bit–

Sherry Walling: I agree.

Jonathan Denwood: And also there seems to be unhealthy trying to classify everybody through IQ exams or tests. But when I studied a lot of the history of IQ testing, it seems quite a lot of it is what I call. I’ve just lost the word it’s, bit suspects, a little bit iffy, a lot of–

Sherry Walling: The product of the military-industrial complex.

Jonathan Denwood: Well, I wasn’t gonna put words in your mouth, but pseudoscience it’s based on a lot of IQ. The history of IQ  is I would classify comes from the area of pseudoscience, but I’m not sure if am been what are your feelings?

Sherry Walling: Well I have lots of feelings. I do agree that education is really, probably not serving many children well. And I would argue that education is problematic because of the lack of differentiation. So we have kind of teaching to the mean. And so kids on the tails, again, whether kids are struggling with a certain subject or kids are excelling and ready to move faster, those two groups of children aren’t being served super well. And of course, the history of education is to sort of raise the general population to a certain level of ability so that they can work in factories and vote and things like that. But the lack of differentiation I think, is really leaving a lot of kids, listless and behind and bored and those kinds of things.

So that’s where I think that the question of IQ does become interesting, not because of IQ in and of itself, but a question of how do we effectively differentiate kids and meet their needs according to what’s possible for them and what they’re capable of achieving. And there’s no great way to do. I mean, that’s a complicated question. It’s a problematic question.

Jonathan Denwood: Oh, it came for me, Sherry. Most of the guests are exposed to my crazy mind.

Sherry Walling: But IQ traditionally, at least, my understanding of it is that it was really a way of trying to assign, soldiers to different kinds of jobs. So it was designed to differentiate people in the military who could do certain kinds of work versus people who should peel potatoes and to do that quickly and fast so that soldiers could be assigned effectively.

Jonathan Denwood: Yeah. But I would just be assigned for peeling the potatoes.

Sherry Walling: I would too. I’m sure, I’ll see you in the kitchen.

Jonathan Denwood: Well not the badest place to be though. 
Steven Sauder:
I was just saying some of the best times I’ve ever had were on pitching crew.

Sherry Walling: We may be the happiest crew.

Steven Sauder: There’s, there’s less mental stress than you could just take it out on a potato, you know?  You can take out that internal stress.

Sherry Walling: I think IQ testing as it exists now is one indicator of differentiation, is one indicator of what a brain can handle, but it’s very narrow to certain kinds of intelligence. It doesn’t capture kinesthetic intelligence, it doesn’t capture relational intelligence, emotional intelligence, all of these other things that we know are super important to success, are not captured in IQ tests. So I think it’s useful among a bunch of other measures to help us understand how an individual is functioning.

Jonathan Denwood:
Yeah. I think before we move on to the next question, Steven will put it to you. I think, a good example of that is Henry fold, who, who had severe dyslexia. And actually, he was shamed. He was taken to court and he was asked if he had ever read a book and he had to admit that he had never read a book in his life and he couldn’t actually read or write that well. But he is one of the original industrialist’s inventors, even though there were aspects of his personality that were particularly unpleasant when it comes to his ideas around racism. But I think that’s a really good example where obviously an individual that’s got enormous drive and capacity doesn’t really fit into the norm. Over to you Steven.

Steven Sauder: Yeah. Yeah IQ is interesting. What, what you were saying, especially like from its roots, cause like, the function that it was supposed to serve right. Was to sort people really fast in a way that needed to happen fast. And like there wasn’t the time and resources, but all of a sudden it’s [Inaudible 27:59 ] metric that more historically, I guess, is used to like determine somebody’s outcome where you don’t need to sort, 10,000 people in a day, it’s used in a school system or whatever; less now, thankfully, but, more historically I guess.

Something that, I kind of wanted to talk about a little bit is social media and perceptions. This kind of goes along with like, the IQ idea too, that, it’s almost a requirement. It feels like as an entrepreneur to be on social media, there’s so much marketing and conversations and stuff that happens on there. and we’ve heard a lot of stuff about, kids comparing themselves on social media, how it damage, one’s perception of themselves. but I think also like as an entrepreneur, somebody in business there’s been moments in time where I have felt really bad about myself because of what I’ve seen or the optics of what I’ve seen, like somebody’s business, gets acquired, right. Or I decided to work for a company versus another company. And then they just get to the IPO stage and you’re like, oh man, if I would’ve made that, decision and we know the people that are set for life now. How, I guess, like, as you’re thinking through like, watching for like that baseline that we were talking about a while ago and like swings and like to make sure you’re mental, okay, there’s still this a requirement to engage in this world that makes it hard. how do you siphon through that or figure out how you can engage in a world that like still makes you feel things that you don’t wanna feel sometimes?

Sherry Walling: Oh yeah. It’s a struggle. As you mentioned, I have, I have this book coming out and, the book got purchased by a publisher. I self-published my first book, but this book is going a professional or a more traditional publication route. And I made the amount of scrutiny that the publisher placed on my social media. I was like, I have a PhD. Like, do you care about that? They’re like, no, no how many Instagram followers do you have? Like, that was the metric of my value as an author. And I was like, this is so backward like this is terrible. So anyway, I feel you, the social media woes.

 I think, the sort of rule of thumb with how to have a healthy relationship with social media is sort of like, how you would have a relationship with 17 magazines when you’re, a, a kid growing up is, use it sparingly. A couple of minutes, a day, pop on, check the newsfeed, make a few comments, leave some messages for people. So have some limits around how much and how long and those kinds of things. I have found some fun and satisfaction as a content creator. So thinking about, how do I make that sort of pithy clever tweet? So letting it be a creative outlet as much as possible, rather than a high-pressure outlet, is probably not a great social media strategy, but I think a lot more about what I’m putting out there. And then I check people that really care about, and I don’t use it as a source for news or for sort of information from more general sources. So being very specific, I guess, with how you’re using social media can be really helpful.

Steven Sauder: Yeah. Like controlling that [Inaudible 31:38 ] how you’re consuming or where you’re consuming it from, instead of just being like a passive thing that you’re always plugged into and tuned into. And although it feels like a passive thing that you’re just checking, it’s actually like a very active thing. That’s feeding all these different things.

Sherry Walling: You are having an emotional relationship with it.

Steven Sauder: Yeah you are. OH, man. Well, thanks so much for the discussion. we’re out time for the podcast where we’re gonna keep doing 15 minutes of bonus content which everybody can tune into on the WP-Tonic Facebook page or the YouTube channel, Sherry, before we move into the bonus content. How can people find out about you and what you’re up to?

Sherry Walling:
Yeah. My company is called Zen Founder, Z E N founder. So I also have a podcast by that name. And that’s at Zenfounder.com. And then I have a book called the entrepreneurs, guides, keeping your s**t together, how to run your business without letting it run you, which I think is a handy dandy resource. And it’s on Amazon and in all the book places, but mostly Amazon.

Steven Sauder:
And Jonathan, how can people find out more about you?

Jonathan Denwood: Oh, that’s easy, but I just wanted to say that I was very moved by your episode about your brother, Sherry. I think it’s episode 220. And your eulogy for your beloved brother, I was very moved by it.

Sherry Walling: Thank you. Is

Jonathan Denwood: Over to you, Steven?

Steven Sauder: did you just wanna let people know how they can find out more about you Jonathan at all?

Jonathan Denwood: I’m not sure if they should really.

Steven Sauder: Well, if you’re on the WP-Tonic Facebook page, you can always see what’s going on latest and greatest what’s going on WP-Tonic. All right so that’s it, folks. Thanks so much, for joining us, and, check us out on the Facebook page to join in for the bonus.

 Outro: Thanks for listening to the WP-Tonic podcast, the podcast that gives you a dose of WordPress medicine twice a week.

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