Get together with strangers, and the question invariably comes up: “So…what do you do?”

Depending upon who’s in attendance, and who’s asking, the level of appreciation for your career choice—that of an entrepreneur—varies. If you’re standing next to, say, a physician, firefighter or international aid worker, your job may not be fully appreciated for the high-stress, high-risk, “Will I have a job tomorrow?” dream job that it really is.

Sherry Walling gets it.

An entrepreneur herself, Sherry is also an author and clinical psychologist with a long history of helping people who end up in high-stress situations by way of their vocations. As a business owner, you may feel alone in the fear, procrastination, doubt, frustration and loneliness of entrepreneurship, but you’re not. As Sherry says, entrepreneurs all break in the same ways. The key is acknowledging when you’re not feeling right and finding ways to give your mind and body a rest. Sound impossible? Take a moment, breathe and treat yourself to a well-deserved moment of founder zen.
 

 
 

On the road to enlightenment? Join us at Owner Summit, where Sherry will take the stage as a keynote speaker.


Carl Smith: Welcome to The Bureau Briefing. Before we get started, I want to thank our sponsors. They are amazing. Thank you to MailChimp. If you need a marketing platform, MailChimp is so much more than just email. They help you with Facebook ads, with Google ads, you've just got to check them out. And the way that you can slice and dice the campaigns, it's beautiful. 

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Speaker 2: Welcome to The Bureau Briefing, a podcast by the Bureau of Digital, an organization devoted to giving digital professionals the support system they never had. Each episode we're going to talk to a member of our community doing awesome, inspiring things. Now for your host, Carl Smith. 

Carl Smith: Hey everyone and welcome back to The Bureau Briefing. Stopping by the show today we have the Founder of ZenFounder, the author of "The Entrepreneur's Guide to Keeping Your S**t Together." I'm just going to say it, I don't care how it's put on the cover here.

Sherry Walling: Just put it all out there, Carl.

Carl Smith: Just put it out there. It's Dr. Sherry Walling. How are you doing Sherry?

Sherry Walling: Hey. I'm so excited to talk to you.

Carl Smith: Well, I'm glad you're here. I read the book over the past few weeks and I just, I know previously I'd said this was going to be my therapy session, and I believe you said you get what you pay for.

Sherry Walling: That's right.

Carl Smith: But I have to say, this is an amazing book and I just want to dive in and ask you what was it that made you decide you wanted to focus on entrepreneurs? I mean, when you were going to get your degree, did you say, "I want to be a clinical psychologist who focuses on entrepreneurs?"

Sherry Walling: I didn't. I didn't say that. Like so many vocational stories, it was a meandering path, and it just sort of happened. I will say, though, I started my journey in clinical psychology working with people who had really high intensity jobs. A lot of folks in the military, and then I worked a lot with first responders, international development workers, physicians, so people who by way of their vocation end up in some really high-stress situations.

I wanted to be someone in the world who was helping to keep those folks as healthy as possible so that they could do the amazing work that they were doing. When I look back at the fact that now I spend a lot of time with entrepreneurs, it's not super surprising 'cause some of the foundation was there all the time. And then-

Carl Smith: We're not dealing with real fires.

Sherry Walling: True, not literal fires, but fires come in many shapes and sizes. And the other piece of the journey, of course, is I have been married to a serial founder for about ... We just celebrated our 18th anniversary.

Carl Smith: Whoa.

Sherry Walling: So the people who have been in my living room most of my adult life have been founders. They've been business owners, they've been tech folks, they've been people who are running agencies, and so that became the community that embraced me and I cared about, and those were my friends and my colleagues, and as I saw these really bright, amazing folks struggle with some significant mental health challenges, get divorced, feel suicidal-

Carl Smith: Wow.

Sherry Walling: ... I thought, "Okay, there's got to be a way to bridge these two worlds a little bit better."

Carl Smith: Do you find yourself unintentionally analyzing friends when they're over at the house?

Sherry Walling: It's funny. I don't. 

Carl Smith: Good.

Sherry Walling: I don't know how to talk about it in a way that doesn't make me sound crazy myself, but there is a part of my brain that I turn on and off, and I really know the difference of a conversation I'm having with a friend versus listening in a clinical way, or listening with like my full therapy training. It's a different listening.

Every once in a while, my husband will catch me and I get this detached intensity and he's like, "Okay, I want my wife back. You lady, you doctor lady, you go away. I'm not paying you."

Carl Smith: That's awesome.

Sherry Walling: He can feel the difference.

Carl Smith: When you are talking with entrepreneurs, how does this work? How do your clients engage with you? Do you actually help entrepreneurs one on one?

Sherry Walling: I do. Yeah, so I have two umbrellas of my work life, and one is I do function as a traditional psychologist, so I have therapy clients, I have a local office here in Minneapolis, and I have just a handful of slots but I do continue to work with people who are struggling with clinical depression, or post traumatic stress disorder, or significant mental health difficulties. 

That's the more traditional psychotherapy world, and then I have another hat, and that's my consulting hat. So I work a lot with folks either on the one-on-one level, or on the agency or business level, to try to think about how to optimize for wellbeing and mental health. Again, whether that's an individual founder or an executive person, or whether we're thinking about the wellbeing of a whole community.

Those mostly happen on Zoom, they happen remotely, so fortunately I get to work with really amazing people all over the world, and be a sounding board and a resource for people who are trying to manage the crazy life of the founder.

Carl Smith: From your vantage point and all the conversations you've had, what are some of the common ailments or common challenges that you see entrepreneurs facing?

Sherry Walling: Yeah, I think we all have our own story and our own brand of neuroticism, but I think some of the really common ones are loneliness and that can often go up and down. Like, I guess I should say that's independent of success. Some people can be absolutely thriving in their business, and feel extremely lonely. And then people can be really struggling in their business and feel really connected, so that's a little bit of a harder one to spot.

Loneliness is something I end up talking a lot with folks about. I think another thing, especially as people are in businesses or agencies that are growing, is the weight of the responsibility of being the decision maker, being the one in charge. That can look like getting really saturated, and having difficulty making decisions, or just feeling deeply responsible for your teammates or the people who are your employees.

I think that pressure can become debilitating if we don't talk through it, and the limits of it. So yeah, I mean-

Carl Smith: I'm trying not to fall over right now as you talk directly to me.

Sherry Walling: Uh-oh. We're also human though, right?

Carl Smith: I know.

Sherry Walling: Like, we all break in the same ways. We feel lonely, we feel responsible, we want to make a great life and a great business, and we are frustrated with our limits to be able to do that well all the time. There's not so much that's profound or novel in what I do or what I talk about because we all break in the same ways for the most part.

Carl Smith: It's amazing to me when we start looking at the way that our industry is going distributed, and so many of us don't really see anybody else except on a screen, for a whole day. And then the laptop shuts down, and your whole world goes away. There is something that's lonely and I've had a few conversations on this show with people who are struggling with eating disorders, or substance abuse, on distributed teams.

And nobody could really tell, nobody knew. That's really insightful to think that loneliness is there anyway, but now we've got this additional layer on top of it. Do you find distributed teams are having slightly different problems?

Sherry Walling: I do. I think that there are great ways to do distributed teams, and I know a lot of companies in the bureau are thinking very carefully about how to do that well and how to create good relationships among team members, even if they're connecting from all over the world. But we are three dimensional creatures. We relate differently when we're in the room, and that data that we receive from body language and just the experience of being physically in the same proximity as someone else, those are important pieces of data, and important points of connection.

When we don't spend a lot of time in a room with anyone else, we miss out on the depth of part of that relationship. It's a problem and it's certainly not a reason to never have a distributed team. That is, you're right, the way that the industry is going so we do have to figure out how to do that well. Whether that means really supporting members of our teams in having relationships outside of work, or in putting people in coworking spaces where maybe they're working alongside people from other companies, but they're with other humans.

I mean, we have to get creative about how we do that, but it's a huge mental health and physical health risk factor, this sense of isolation and loneliness, so we can't ignore it, that's for sure.

Carl Smith: Especially when we look at the pressure and the stress for somebody who's in charge, and they've got all that responsibility barreling down on them and the walls can really close in. Again, I'm not saying it's happening to me, but it's one of those things where when there's nobody else to look at, yeah, that can just be crippling. Your internal critic just turns on so loud.

Sherry Walling: Yes. Like, "What's wrong with you that you can't make this work? Look at all these other business owners that seem to have their shit together, and what's your problem that you're falling apart right now?" I mean, the voices that live in our head can be brutal.

Carl Smith: That's actually been one of my struggles lately, is I should be super motivated. I have got a soon-to-be 17-year-old and a 15-year-old daughter, they're going to be starting college, right? Next year and then two years after that. And I've really, thank you very much Entrepreneur's Guide, I've got to keep my shit together.

That is one of the things that I really got out of the book. I will find myself sitting, staring at my laptop, knowing that I've got to do stuff, but if it's acute stress or whatever it is, I just can't hit a keystroke. In the book, it talks about procrastination a bit, and you've got some rules in there. Would you go deep on that for a minute, and just share what people can do when they find that they're just stunned?

Sherry Walling: Yeah. I think one of the pieces of research that was really interesting for me to think about as I tried to get my mind around how to help people who are procrastinating, is this idea of having a positive relationship with your future self, which sounds so maybe like strange, psychological intervention, but it's to really realize that the Carl that is going to be around two years from now, Lord willing, is really going to want you to have done your work so that you can pay those tuition bills.

Carl Smith: He's not a big fan, I've got to tell you. Two years from now, looking back.

Sherry Walling: He's like, "Please Carl of 2018, hook me up. Do a brother solid."

Carl Smith: [crosstalk 00:13:42].

Sherry Walling: I think one of the challenges of procrastination is that we get so in our heads and so critical, in the moment. Like, "I should be doing this work, why can't I do this work? What's wrong with me that I can't do this work? The conversation then becomes about the narrative of self-criticism, and our attacking ourself for our failure to be motivated and get things done." It just turns into this whole cycle which of course makes it really hard to chill and focus, and get your work done.

So one of the other strategies is really to practice disrupting that cycle and practice the radical kindness to oneself, regardless of the situation. If that means that you say to yourself, "Okay, I don't have it right now for whatever reason. I'm going to step away form the laptop, walk around the block, go play with the dog for a few minutes. I'm going to give myself the benefit of the doubt rather than this spiral of criticism. In my head, I'm going to reset how I'm feeling about the situation, and be kind to myself and then I'll come back to the work when I can come back to the work."

Carl Smith: That today I was sitting there, and I had emails that I had to reply to. There was nothing major about these, but I grabbed the book and I mentioned this to you previously that I use the book a little bit as a resource now. I was just going back through that and I went, "Why am I not replying to these emails? These emails are not a big deal." Then I looked at what was next, and it was working on new offerings from the Bureau.

As soon as I was done with these emails, I was going to have to work on that and I've messed that up before, and I've got some internal pain around things that I've tried before. I was like, "Oh, I see what's going on." Don't have anything to do with the emails, it has to do with what's next.

Sherry Walling: Yeah, and your feeling about what has to happen once you're done.

Carl Smith: Yeah. What I ended up doing, and I think other people I know do similar things, I just answered the emails, but I did it while I was walking. I mean, I have a phone that's pretty cool, so I don't have to sit in this room, and I can get out and I can do those things. The other thing for me is sometimes I like to run, and that in itself is probably some sort of psychological issue.

But when I go for those runs, my brain can fix things. Then when I sit back down, I can do it. Is there something about doing physical activity and then coming back to something that you've been stuck on?

Sherry Walling: Oh, absolutely. There's a body of research behind that experience you're describing, especially with running. We like to think that our work comes just from our prefrontal cortex, the front of our brain, but it doesn't. We're super embodied humans and when we are stuck in a part of our brain, often one of the best things we can do to get unstuck is to physically move our arms and legs and move our body around.

When we change the context, the setting, the situation that we are physically in, we have the power to reset the whole thought process. There's also really a lot of benefit to physical exercise as a way of stimulating the activity of our brain. It's this bathing our brain in this nurturing energy. That sounded very hoo-hoo, but I'm talking about endorphins. I'm talking about [crosstalk 00:17:32]-

Carl Smith: I'm a short-haired hippie. You're fine.

Sherry Walling: Nurturing energy. I mean, on a scientific, neurological level, we're saturating our brain in neurotransmitters that are really helpful for us.

Carl Smith: I left my crystals in here somewhere. Let's head to Asheville.

Sherry Walling: I'll send you a TED Talk from a neurologist, okay? I do some strange things, but this conversation is not one of them.

Carl Smith: No. I'm glad to hear that. I knew there had to be something. I always figured it was just I get my body so active, that my brain knows that I'm going to be doing the same thing for a while and I can just let go. You know what I mean? It's that same concept of acute stress versus chronic stress, where we lock our brain out from doing the one thing we're telling it to do, right?

Sherry Walling: Yes.

Carl Smith: That's why you think of things in the shower, 'cause you told your brain, "Hey, you know what? Forget it." And your brain goes, "Oh, by the way."

Sherry Walling: And especially with tasks that are creative, or novel, or your to-do list of, "Think about new offerings for Bureau of Digital." Like, you can't force that. You have to come at that from an open neurological space where your brain feels free to play and dabble, and can't be under pressure to generate creative material.

Carl Smith: I mean, we only have so much time, and hell, I could just call you up after the show. That's fine.

Sherry Walling: We can talk [inaudible 00:19:01].

Carl Smith: I want to circle back around to the idea of entrepreneurs and depression, and how people can reconnect with a sense of meaning. I'm sure it's different with every person, but when you find out that somebody just doesn't seem to know why they're doing it anymore, and they're just lost, how do you help them reconnect with their purpose?

Sherry Walling: It's a little bit of an unfolding process, unfortunately. I wish it was easier and faster.

Carl Smith: So do I.

Sherry Walling: Truth be told, it's a meandering conversation a little bit. I think some of the first questions that I have in a conversation like that are about how well someone is just taking care of the basics of their own self. How well are they sleeping? How well are they eating? Are they moving their body? Do they have the basic building blocks in place to be able to have an existential conversation?

Because without some of those simple things in place, you're just not able to function as well as you need to be able to to make good big decisions. And then, I like to ask people about how they got into the work that they do. What motivated them in the first place? What were their priorities? Has their job as it currently exists, shifted away from that? Has it shifted too much? What meaningful things have replaced it as they have gone on in their career?

I think it's this process of elimination, in terms of trying to identify what takes us away or gets in the way of a sense of meaning and connection. For many of us, it's busyness or it's becoming so successful that we've now become a CEO, and worked ourselves out of the job that we loved. We're not designing anymore, we're not writing anymore, we're not doing the things that we used to feel really excited about.

But if someone is really in burnout, again, I wish there was an easier way, but it is almost always necessary for people to take a couple weeks off, and really let the conversation reset and give the body and the mind a break. Nobody likes to hear that from me, but it's not like, "Hey call me up in an hour, we'll have you all patched up." Every once in a while that happens, but usually it's like, "Okay, you're not all right. We have to listen to that. We have to take that seriously. Let's put everything on pause and see what we can do to do some deep investigation about what it is that you need at this point in your life."

I think the other tricky thing about meaning is that it changes, right? As we develop as humans, as we go through different phases of our lives and our work life in particular, what becomes meaningful and motivating shifts. We don't just get to like figure it out and it's one and done. We have to constantly listen to what's happening in our inner lives, so that we can stay on top of it.

Carl Smith: How difficult is it for those CEOs, managers, entrepreneurs, to take that time off? Do they feel that everything's going to fall apart if they step away?

Sherry Walling: Yep. Exactly.

Carl Smith: I think early in our lives, we want to be important so bad, and later in our lives, we realize being important is the worst possible thing we could want. It makes it impossible to step away. But I love what you're saying about you have to have your own basics down. Sherry, thank you so much for stopping by the briefing today. I truly appreciate it, and I'm also excited, because you're going to keynote at Owner Summit 2019 in Austin next February. Thank you so much for that.

Sherry Walling: I cannot wait. It's going to be great, and thank you so much for having me. I love what you've built with Bureau of Digital. I'm such a huge fan, and I've gotten to know some of the folks in your community, and it's a great place to hang out in person, or via podcast. So thank you for inviting me in today.

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