Episode 250 Featuring Alex Bond

Therapy for Entrepreneurs with Dr. Sherry Walling

Therapy for Entrepreneurs with Dr. Sherry Walling

Dr. Sherry Walling is a clinical psychologist, speaker, podcaster, author, and mental health advocate. Her company, ZenFounder, helps entrepreneurs and leaders navigate transition, rapid growth, loss, and any manner of complex human experience.

Sherry also hosts the ZenFounder podcast, which has been called a “must listen” by both Forbes and Entrepreneur Magazine and has been downloaded more than 1,000,000 times.

Her new book, Touching Two Worlds, is an award-winning, poetic, incisive exploration of grief and joy in the aftermath of loss. 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.

On this episode, Sherry and I discuss some of the mental roadblocks that entrepreneurs deal with, her path to psychiatry, went to seek psychiatric help, and much more.


What is ZenFounder

Sherry Walling: Yeah, I am a clinical psychologist by training. So Zen founder is a place where we provide mental health. Related services and information to entrepreneurs of all different kinds.

Alex Bond: That's great. And so your specialty is in helping entrepreneurs with any sort of mental health struggles. I mean, what are some of the mental roadblocks you're referring to that that entrepreneurs deal with? 

Sherry Walling: Yeah, I mean, as you are well aware, and I'm sure your listeners are aware, like entrepreneurship is a journey of high highs and low lows. And so finding some balance or cadence in the midst of that instability is really important for folks. 

So our team does lots of things. Sometimes we help negotiate co founders that aren't getting along super well. We kind of do therapy for co founders. Sometimes we really help people think about how to prevent burnout.

Other times we are just part of the support system. We're along for the ride for the life of the company years, sometimes where founders want to have a safe, objective sounding board to talk through the ups and downs that they're experiencing within their company. 

Alex Bond: And just kind of like feel heard more than have someone fix the problem sometimes. 

Sherry Walling: Yeah. Or sometimes have somebody help fix the problem. So, you know, I think consulting is a little bit different than traditional therapy in that sense where my team and I are responsible for helping people move to a different spot. 

So if someone is coming in and they're having conflict on their team or they're feeling really disengaged or like they just don't have that creative oomph that they used to have, we want to help provide solutions. Like my job is to help people feel better and act better and show it better in their companies. 

But people, you know, really benefit from an external sounding board. That's an informed listener, but doesn't have a horse in the race. So one of the other things that I end up working with people around a lot is the decisions around whether to sell their company or when to sell their company.

What is the exit? What are they going for in? The life of the company, you know, do they want to stay for 15 years or do they want to have an exit in three? Those are very different companies and very different pressures and helping people discern for themselves what they most want is really important.

Alex Bond: Yeah, absolutely. So what are some of these other specific solutions that you provide? Is it reflective listening practices? Is it? Trying to get people to mindfulness exercises, yoga. I mean, what are some of these tangible solutions that you're referring to? 

Sherry Walling: Yeah. So some of the things that you're suggesting, I would call sort of a suite of mental hygiene. So we know that exercise is really helpful for your mental health. 

We know the breath. Your ability to calm yourself down through breathing is really helpful for mental health. So almost everyone who comes through my practice is going to get some introduction to just the basic foundational of like how you really care for this amazing machine, which is your brain.

So it's almost always movement. It's almost always breath. We talk about like nutrition, sleep. These are just the building blocks that. Are universally helpful to all of us, especially as we face increased pressure as our businesses are growing or experiencing challenges. Beyond that, those highly individualized strategies are different for everyone.

So depending on someone's background, their family history, maybe they had a lot of trauma in their childhood. What it looks like for them to lead a company is going to look a little bit different than it looks like for another person who was sort of the, the golden child in their family and didn't have anything pretty like anything terrible happened to them, but maybe had a lot of expectations put on them.

So the individual sort of psychological factors are going to be different for those individuals. And so that's where my job, my team, we just like dive in and really see who is this person in front of us? What are their unique challenges? What do they need to move them forward? And we build that then on top of the foundation of kind of universal basics that help all of us function better.

Guiding Through Milestones: Partnering During Critical Career and Business Transitions

Alex Bond: Is there a specific time in people's careers or lives that you usually start working with them. I mean, is it like when something big is happening at the company where they, they are about to scale very quickly and they're really stressed out about it? Or is it when they're about to start a company or when they're going to sell it? I mean, or is it all of that? 

Sherry Walling: It can be all of that. I would say in general, my team and I kind of come on board right around the time of hiring like employee number eight, because that's where you've moved from like a really small agile team to a company that needs systems and structures and has some more complicated interpersonal dynamics. 

And often founders come to their company with a set of skills. Maybe they're highly technical, maybe they're great at SEO, maybe they're coders, maybe, you know, they've figured out some way to hack the system to their advantage, but they're not always good at the people things. They're not always good at dealing with grumpy customers or dealing with team members. 

And as your company grows, the pressures change. And the really the tasks of the job change and that tends to be this point in the life of a leader where the things that brought them to a certain level of success are no longer really what is needed to move them to the next level and it's a little bit of like a midlife crisis in in the life of a company.

So that tends to be the point where people are like, Hey, I need some help. I need to be able to do this better. And I think the other main times that people reach out to someone like me are again, in this sort of question around an exit or a major transition, or maybe something externally has happened.

They're getting divorced, they've lost a parent, they've had their second child and they're just totally overwhelmed. Those kinds of not specific to the business, but personal life factors really. You know, our times when people often benefit from additional support. 

Alex Bond: And part of what I'm hearing you say, Sherry is like entrepreneurs generally are self motivated in terms of I'm going to go out here and do this thing for me with myself at the focus if that makes sense. 

And so when that mindset has to change and now I'm in charge of a 20 other people. I can't exactly operate of, like, if something goes wrong, it's just me who takes the fall or I'm only putting myself at rest versus now an entire other group of people. That's kind of a long way of asking, is that normal for every entrepreneur that has to kind of like grapple with this self focus to team focus? Does every entrepreneur that starts a business have to have to kind of deal with that problem? 

Sherry Walling: Not necessarily. I mean, a lot of entrepreneurs stay solo. I mean, that's a really great model. Actually, for an agile and highly profitable business is to keep your team as small as possible. I mean, having a team solves a lot of problems, but it also creates other problems. And so sometimes there's an important conversation to be had around even the model of growth. 

Does it include a team or not? Because especially a lot of eCommerce businesses can solve scaling problems with processes and technology and don't necessarily need to hire numbers in order to, you know, move the business forward. So it's not necessary that everyone grows in the same way. It's just a thoughtful choice around what's the best strategy. 

Exploring the Relationship Between Coping with Trauma and Symptom Dissipation

Alex Bond: And you mentioned something just a little bit earlier in terms of background about myself. I worked, I want to say two or three years ago as a recovery coach and peer recovery specialist for people in recovery from substance use disorder, which also is dealing with mental health struggles some effect. Most people who are, who have a substance use disorder are dual diagnosis to some effect. 

But one of the gentlemen that I worked with was pretty emphatic that all recovery and that's recovery from mental health or recovery from substance use disorder is rooted in like trauma to some sort of effect. So I'm curious if you agree or disagree with that like usually, there is some sort of trauma to find and once you can cope with that, then the symptoms begin to dissipate? 

Sherry Walling: So this is an interesting question. This sort of emphasis on trauma has become really, I guess popular is the word I would use. And has really been pushed forward by folks like Dr. Gabor Maté Dr. Bessel van der Kolk. These are wonderful, wonderful physicians who I think have thought quite deeply around the role that trauma plays. 

I came up in my training actually as a trauma specialist and trained at the National Center for PTSD, which is in Boston, well, has sites around the country, but I was at the site in Boston. From that context, when we think about a PTSD context, we're a little bit careful about what we mean when we say trauma. 

So trauma does have a technical definition, which involves the threat of loss of life to oneself or someone else. Or a significant violation of one's physical integrity, which would be cases of sexual assault or abuse.

So I do feel a little bit protective of what we're talking about when we talk about trauma. So one of the things that I've started to do, I don't think I'm the only one that does this, is talk about sort of capital T, Trauma. Which is that kind of trauma where an overwhelming experience has happened where someone's Deep safety or body is really, really in danger.

And then there's trauma that's lowercase T, trauma. And those are experiences of feeling really uncared for or like not understood by someone's primary caregivers, which are also significantly psychologically disruptive. But not necessarily what I would call trauma from, you know, it sort of varies person to person.

So all that to say is, I think the things that matter to us in our formative years are extraordinarily important to how we develop. And even experiences of feeling uncared for or alone that happened to us as babies before we're verbal can set us up for how we physiologically respond to stress for the rest of our lives.

The difficult things, the traumatic things, the disruptive things that happen are incredibly important in shaping how unwell we feel in our bodies and what kinds of things we're grasping for to cope. Substances being a prime example of something that is a regulating force to our physiology. That people are variably responsive to depending on how much disruption they've had in their early life experience.

So that's a very sort of long, I guess, and so it went technical answer to your question, but generally the answer is yes, the things that happened to us early in our life matter very, very much to our substance use. 

Entrepreneurial Well-being: Navigating the Optimal Time to Seek Psychiatric Help and Therapy

Alex Bond: I'm curious at what point especially for entrepreneurs, should someone begin to look into seeking psychiatric help or any sort of therapy from someone such as yourself? 

Sherry Walling: You know, without it sounding like a pitch for me and my people, I really think that If you are someone who wants to accomplish pretty extraordinary things, your own capacity to be self reflective and in touch with your shadow parts, in touch with your own painful past that may have some bearing on your future and your present.

That's a process that begins sooner rather than later. So, you know, for those of us who do really difficult work in the world, like. You have a person the whole time. Maybe it's not the same therapist. Maybe you don't meet every week routinely on Tuesday at 10, but you have someone in your life who is your objective sounding board, who can sanity check your decisions and your impulses, who is a guide, a counselor. 

So that can be formal. It can be a therapist, a psychologist. It can be a member of the clergy. It can be a coach at different times. It can be a mastermind at different times. So I don't think it has to be the same thing throughout the course of your career, but it should be something.

Alex Bond: No, that's great. And I appreciate you expounding on the fact that it can be someone that isn't a therapist, as long as it's someone that can kind of provide that sort of space for you. Some entrepreneurs believe. 

Well, this is kind of old hat, but I definitely know that there are some. Still, people who believe adversity instills a mental toughness, almost like their struggle is a badge of honor or a notch in their resume or that, you know, again, it creates some sort of tough attitude to some sort of effect. Is there any sort of benefit to like not getting help like that or is that really just stubbornness and that's kind of like an archaic way of thinking? 

Sherry Walling: I mean, I think life is hard. And hard things are going to happen in your life. You know, we've all gone through a pandemic. Many of us lost people we love.

There's 100 percent guarantee that hard things are going to happen to you in your life. I don't think we need to idolize difficulty. And I don't think we need to go through difficult things by ourselves. And to believe that there's some kind of badge that goes into our autonomous ability to function without the well being or like without the help of another person, you know, I think.

When we talk openly about the difficult things that happen to us, that can be helpful for ourselves and for others, but not from a tone that's like, and look what a hero I am that I could grin and bear it through these really pain through the divorce or through the closing of my company or through these painful things. That's not a helpful conversation. It's not realistic. 

Breaking Barriers: Paving the Way for Global Mental Health Advancement and Continued Destigmatization

Alex Bond: And you mentioned something that I think is, is really valuable in that is. The pandemic to some sort of effect. I mean, mental health awareness is something that has become increasingly de stigmatized in the last few years. 

And I think that personally, I think the pandemic really opened up a lot of people's eyes to their own mental health struggles and different people saying, you know, panic attacks, anxiety, that stuff doesn't exist. You're not just not being tough. 

And then a pandemic happens and then people are faced with their own reality of. Maybe it is real because it's happening to me. Essentially, my question to you, Sherry, is what's the next step in continuing to curb mental health on a large scale or in the US or in the world? I mean, it's something that is becoming increasingly destigmatized. How does it continue to be? 

Sherry Walling: That's a great question. I mean, I think that we've come to a general culture understanding of well mental health is a big deal. And when our mental health isn't in a good place, all manner of things fall apart, our professional lives, our parenting, our relationships, the place I would like to see the conversation going next.

And it's happening, but is this broad understanding of the sort of basic building blocks of mental health like I was talking about before, how our food, our sleep, our water intake, all of like the hours that we spend sitting in a chair in front of a screen, how all of those are directly shaping. That mental health experience, and they're all completely within our control, both as individuals and as businesses and as a society.

So let's translate the concern that we now have about mental well being and start applying common sense to our systems and our expectations. To give ourselves a bit more of a buffer and a bit more of a strong foundation underneath us when we're thinking about mental health. So one of the things that just like kills me as a psychologist and as a parent is we know a lot about how kids brains work and the relationship to movement and activity and then ability to focus. 

But yet many kids who are elementary school age or middle school age spend six hours sitting a day, which is absolutely not good for their mental health. Like, it's just not good for their mental health. So kid gets in trouble at school. What's the thing they take away? Recess. You can't go out at recess. 

So I, you know, I think there's, those are little systems where it's like, this is stupid. If you say that you care so much about the mental wellbeing of children, let's have structures around kids that actually support their mental health. Same is true of adults. 

Like the reality is that we shouldn't have an expectation of ourselves or of anyone else that we have our butts in the seat of a chair for eight hours a day. It's not good for us. It's not the way that we do our best work. I would like to change some of those systems, now that we're all so concerned about mental health. Let's do something about it. Even these little, simple, very sane things. 

Alex Bond: Like access to, you know, resources in the workplace or something like that. I'm curious about the other side of the coin now, essentially, which is that with a proliferation of knowledge of mental health, I don't know entirely if I believe this, but I think that there is a capacity for people to essentially weaponize mental health to some sort of effect in terms of, I don't know, using buzzwords and specific, very surface level knowledge to, I don't know, self diagnose things that might not be diagnosable. 

And that's not to discredit people, I just know that there is a certain line where I think people are okay crossing it, because it's still a developing thing. Is it possible to weaponize mental health for my own selfish gain, is kind of what I'm trying to ask?

Sherry Walling: I also think that there's downside of democratizing the conversation right now. There's lots of language around, do you have narcissistic personality disorder? And so everybody's like a little bit of like a couch therapist. Again, like the conversations are happening. I'm cool with that. It's great. 

But when I see like an influencer on Instagram, who's like, let's talk about tips for your mental health. You know, we can get through the five point listicle. And maybe that's helpful for people. But when we talk about really substantive, meaningful thought and help, I would like to think that we do need to still talk with the experts, like with people who've been doing mental health care for years and years.

You know, I think people don't necessarily understand the amount of expertise and experience that goes into getting a license, for example. So I'm a psychologist. I went to five years of graduate school after my undergrad. Then I did a postdoctoral fellowship that was very, very focused on trauma. And I had to do 3000 hours of supervised clinical work before I could get a license.

So 3000 hours, right? That's essentially a year and a half of time where everything I did was observed and documented and critiqued. And, you know, that doesn't mean wisdom. That doesn't, that's not the only way to get wise or to be helpful related to mental health, but it certainly means that like I put my reps and I put my time in thinking about the best way forward and some of these really tricky human experiences again, I'm happy for the conversation.

I think the democratization of the process and the language is really helpful, but let's not forget that in our cultural milieu, we have folks who've. Really done a deep dive in how to help and I don't, you know, we don't want to like substitute those folks for like. The cool influencer on Instagram.

Unveiling the Path: The Journey of Discovering Entrepreneurial Psychiatry as a Personal Calling

Alex Bond: I'm interested how when you first realized that entrepreneurial psychiatry was your path. 

Sherry Walling: Yeah, it was super specific. Actually, as I mentioned, I trained as a trauma psychologist, so I was primarily working with members of the military E. R. Docs first responders. So people who were exposed to trauma in the context of their jobs. And then I married an entrepreneur, a tech entrepreneur. My husband's name is Rob. 

And so I was coming up In graduate school and early in my career working with folks who had really high intensity jobs and he was coming up founding companies and so we had all these like software startup people in our living room all the time and I was just really aware that like a lot of them weren't doing well.

But then I came home one day and I found my husband crying in our office, which is an unusual thing. This is a man with like two engineering degrees, like kind of not a big crier. And he let me know that Aaron Schwartz had died by suicide. And I was like, that's terrible. Who is Aaron Schwartz? Like, I don't know this person.

But Aaron, of course, was one of the co founders of Reddit and was just this like super brilliant young tech mind who died by suicide in his early twenties. And I think for whatever reason, it was just one of those events that was like, this should not have happened. I don't know this young man. I don't know anything about him. 

But I know that there are lots of just brilliant folk running around creating companies who get lost in the stress of it, who get lost in all of the pressure and really lose their ability to ground themselves when their company goes bad or when things get really difficult.

And so I wanted to take what I was learning about folks who were experiencing trauma in their jobs and bring that forward to be helpful to entrepreneurs who were, you know, having a difficult time in the context of their work. And so that was sort of the beginning point. I started a podcast, my husband and I worked on a book together, and now that's, that's all I do. That's my entire day job is is helping entrepreneurs with. Mental health kinds of things. 

Alex Bond: That's great. I appreciate you sharing that story. I'm interested, Sherry, if it's kind of like the saying, who gives the barber a haircut? If you have a therapist or a psychiatrist that you see personally. 

Sherry Walling: Yeah, I have worked with psychologists or therapists, as I mentioned, sort of throughout my whole career. When I was in graduate school, it was really encouraged, right? It's like, if you're going to do this job, you should probably know what it feels like on the other side of the college. 

So I had really positive experiences of therapy, you know, in my early twenties and then as I've gone through the ebb and flow of my own life, raising children, being in a long term marriage, starting a company, I found it to be so helpful. I have a person, I have a therapist, we use a couples therapist as we need to. 

I've worked with business consultants as I need to. So I think it's so helpful and important to just get the help you need. It's like going to the dentist or the doctor, like just take care of that part of your brain and your life. And I'm absolutely no exception to that. 

Alex Bond: And you bring up something that I think is somewhat important too. And that's not everyone does have great experiences. So I'm interested if you had any advice for people who say had a bad experience with a therapist and essentially are in a mental state of, I tried it didn't work for me.

Sherry Walling: Yeah, unfortunately, finding a good therapist is a little bit like dating like. You got to kind of like sit crappy dates before you find someone that really you feel like a fit with because it is a deeply interpersonal experience. And so you have to feel like they get you. You have to enjoy talking to them.

I went in and did a consultation with one potential therapist and I walked in her office and she had like a huge bookshelf that was covered with bookshelves. absolutely packed with like little figurines. And I think she used them for play therapy, which is totally cool. But I was like, there's no way that I can sit in here and talk to you about my deep dark things with like 700 little figurines staring at me.

There's no way I can do it. So that's not a fit. One of the best strategies is, is word of mouth. You know, talking to who your friends are saying trying to find someone who does have some experience with entrepreneurs is also helpful when I started in this work, I was kind of like there were like five of us that we're doing it now.

There are many more clinicians or people who have experience with entrepreneurs and I sort of aware of that journey. So that's going to be really helpful to the most of the people listening here. And I think the other unfortunate thing is just to like, try a few folks. Most therapists will do like a 15 minute free consultation call.

So that way you're not like wasting your time, wasting a whole hour driving somewhere, whatever. You can just do the 15 minute, like, Hey, do we kind of, it's like speed dating. Like, do we kind of. Jive, and then it's like, trust your instincts and trust the process. 

Alex Bond
Alex Bond

Meet Alex Bond—a seasoned multimedia producer with experience in television, music, podcasts, music videos, and advertising. Alex is a creative problem solver with a track record of overseeing high-quality media productions. He's a co-founder of the music production company Too Indecent, and he also hosted the podcast "Get in the Herd," which was voted "Best Local Podcast of 2020" by the Richmond Times-Dispatch in Virginia, USA.

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