Episode 377 | Staying Sane While Starting Up With Dr. Sherry Walling

Show Notes

In this episode of Startups For The Rest Of Us, Rob talks with Dr. Sherry Walling about staying sane while starting up. Sherry talks about her work with the founder community as a clinical psychologist. How to deal with stresses and fears while growing a business and the importance and power of retreats.

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Rob: In this episode of Startups for The Rest of Us, Dr. Sherry Walling and I discuss staying sane while starting up. This is Startups for The Rest of Us Episode 377.

Welcome to Startups for the Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome at building, launching, and growing software products. Whether you’ve built your first product or you’re just thinking about it. Im Rob.

Sherry: Hi, I’m not Mike.

Rob: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What is the word this week, not Mike?

Sherry: Well, I’ve been compulsively checking for the mail. I keep going down and pushing the snow out of the way so I can open the front door to see if the package has arrived that has what I hope is the final proof for my new book. But we had 11 inches of snow so the whole infrastructure of the city is slow going and I’m not sure that the delivery will get here today.

Rob: Traffic is not great today. There’s just a lot of stuff. All the schools are closed. All three of our kids are home today, and I feel your urgency. You’ve run through a few proofs. It’s the cover. Is the cover having some struggles with the printer?

Sherry: The cover’s having some trouble and part of it has been sort of the designer not understanding which template to use but also not asking but me also not making sure. There have been some communication lapses and then the first round of the proof came the week before Christmas and so we were bogged down with the holiday as well. So it’s just sort of a slow process to get that final hurdle of the final, perfect, most beautiful version of the book printed.

Rob: I can feel you there. In case someone is completely lost, you are Dr. Sherry Walling. You and I have been married for going on 18 years. You and I host a podcast called ZenFounder. You are @ZenFounder on Twitter. You recently completed a book with a little help from me. I’m the with on the book. I’m the second author. The book is called The Entrepreneur’s Guide to Keeping Your Shit Together, How to Run Your Business Without Letting It Run You. I’m pretty stoked about the book. Are you stoked? Are you excited?

Sherry: I am excited and I also feel some trepidation. I think it’s like founders [inaudible 00:02:31] You’re gonna launch something, it’s like you’re putting a little bit of yourself out there in the world. In this case, it feels like it’s a lot of myself. It’s 50,000 words from yours truly. It’s a lot about how I think about life as a founder and I’m super excited to put it out there. It’s been a lot of hard work. But I’m also totally scared that people will hate it or they won’t care.


Rob: The indifference would be not good. You’re packaging a heck of a lot of expertise into the book. You have a PhD in Psychology. You have also been married to me, a serial founder, for like I said going on 18 years. You’re an entrepreneur yourself having essentially launched ZenTribes. You’ve launched essentially a consultant practice. You have actually a really good ebook that’s gotten pretty reviews on retreats, how to take founder retreats. We’ll actually talk about that a little later on the episode. But you’re getting yourself out there in a way that I don’t think you or I would have expected even 10 or 15 years ago. There’s been a shift in you since maybe the last 5-7 years.

Sherry: I set out when I began my career as an academic. Life as an academic has a lot of conference presentation and writing but it’s just on a much smaller scale. In the opinion of most academic communities, what it means to cultivate expertise is 15 years in the trenches and lots and lots of papers. I’ve ended up shifting and now I’m working in the founder space and I still now have 15 years of expertise in lots and lots of podcasts, maybe not papers. I’ve begun to be someone who has wanted to get information and helpful tips to a much wider audience, not just the academic community, which of course has meant lots of hustle and lots of hard work to try to package a message in a way that’s most helpful and most accessible to people who need it.

Rob: That’s the thing in the startup or the founders space. I have, over the years, seen a few people come out of the woodwork, who are being the CEO/Coach or the Founder/Coach but they don’t have the credentials and in a lot of cases don’t have the experience that you do.

I remember maybe four or five years ago you were saying, “I want to go location-dependent with my work.” I remember us having this kind of conversation like “Should you dive deeper into yoga? Do you want to do more of that or do you want to dive deeper into serving founders?” It was a deliberate decision and we started ZenFounder and quickly become obvious how much of a dearth of really knowledgeable people there are in terms of staying sane and staying happy and keeping relationships healthy and not struggling with anxiety or depression or at least fighting through it, figuring out how to work with it.

There are so few people in our world. This is both the venture funded world, it is the bootstrapped world, and it’s also the broader entrepreneurial world. Let’s say you’re not doing a startup, there seems to be a real, definite need for folks, someone like you with your expertise. There aren’t any around. Every time you speak in a conference, it seems like people are saying, “Wow, what a breath of fresh air, not a lot of people are talking about this.”

Sherry: I think there are lots of helpful sources of information from lots of different places. One of the things that I try to do is to pair years of science based education and even my years working as a researcher with the on-the-ground experience. And I think being married to you is worth two PhDs on Entrepreneurial Science.

But I think much of this conversation began when Aaron Swartz committed suicide. And then shortly thereafter, I felt like we heard very often about founders who had taken their own lives or whose lives have just got totally derailed. I look at those kinds of instances or something that is potentially preventable, not 100% of the time, not perfectly. I certainly don’t know, I don’t have all the answers to try to keep someone alive when they don’t want to be alive.

I think there’s a lot of information in the psychological literature, especially in the clinical psychological literature, that can be super helpful to help people manage stressful lives and optimize their performance which is what most of us are trying to do. I think sometimes people hear clinical psychologists and they think like, “I don’t need a doctor,” or “I don’t need to see a therapist.” If we reverse engineer what we know about what breaks people down, what causes mental illness, if we do that backwards, often we can learn a lot about what helps people be really well. I think that’s what we try to accomplish with ZenFounder; get the information out there that can prevent problems before they start.

Rob: I think in addition to that, I see you as keeping people at the top of their game. Stress and all the stuff we’re talking about, all the negatives because there’s so much that comes with being a founder that just is thrown at you constantly, it can and will negatively impact your performance, and your throughput, and your ability to think clearly, and your ability to make really sharp and quick decisions.

I see you helping people, whether it’s one-on-one, whether it’s through your ZenTribes, whether it’s through the book or through the podcast, keeping people on top of their mental games so that they can perform because a founder’s job is not sitting on the sidelines and hanging out. It’s like you’re in the middle of the field, you’re the quarterback and everybody’s relying on you. If you’re stressed, you’re hungry, you’re tired, you’re not sleeping well, you’re sick, whatever, it negatively impacts everything including your bottom line and long-term, your health.

That’s where every founder or aspiring founder needs to be thinking about this topic, about how to stay sane, and how to stay mentally well and healthy and strong while you’re starting up. Even if you’re just an early [inaudible 0:08:41], if you’re doing it nights and weekends, you’re gonna get less sleep. You need to start thinking about how am I gonna counteract that? How am I not gonna burn myself out? How am I not gonna push myself too far? That’s where the message coming from you is so critical. I think a lot of people hand wave it away. Some of the founders go, “I don’t need that,” or, “I’m not sick,” or, “I don’t have depression,” or, “I don’t have anxiety.” That’s not the point. It’s just being more productive and being on top of your game and really not letting yourself burn out.

Sherry: I think I’m a reasonable speaker. I definitely have things like [inaudible 00:09:12]. I’m always astounded when I start talking about things like sleep or things like communication with your spouse. When I give a conference presentation on some of the basic parts of life, the room is pretty transfixed. People are really hungry to figure out how to help their lives go more smoothly, not only to optimize their performance, which of course is a high goal for many founders, but I think to make life enjoyable even in the midst of doing hard things.

Rob: We’ve talked about your background. Folks who want to learn more about you can go to www.zenfounder.com. We’ve talked about why this is an important topic for pretty much everyone listening to the podcast and why folks should be thinking about this from day one.

When you’re just getting started, there’s gonna be tough times. When you start to have success, there’s gonna be stress. The more success you have, the more stress I felt I had. There’s so much writing on you. You get a company to 10 people, now they’re relying on you. The dollar swings are way bigger. You have a great month versus a bad month. It used to be a couple of thousand dollars, it can be 40-50 grand difference. And suddenly it’s like “Whoa! The stakes just became very high!” Hopefully, folks listening to this have been taking notes if they haven’t been thinking about this yet.

I wanna touch on two topics today and have you talk through them a little bit. These are both out of the book. We’re gonna talk about self-knowledge and I wanna touch on retreat. You started going on retreats and I was really intrigued by them. I went on my first retreat years ago and I came back and raped about it on the podcast. And then it kind of spread through our circles. And there was no one, absolutely no one, talking about founder retreats before we did. I feel a certain pride that we were able to bring that into the space because it’s just a novel and helpful thing. Everyone who goes on one comes back to me and says, “Oh my gosh, it completely blew my mind!” I wanna be able to make sure that we do touch on that.

Let’s dive in a little bit to this idea of knowing yourself or self-knowledge. In the book, you talk about some different extremes. You talk about chaos versus rigidity, introversion versus extroversion, fixed mindset versus growth mindset. I know each of those is a concept all to its own. Maybe kick us off with why is it so critical to know yourself, and then talk through maybe one or two of those concepts.

Sherry: The premise of the conversation about self-knowledge is very practically helps you plan around your relative weaknesses and maximize your relative strengths. If you’re thinking about starting a business or you’re knee-deep in the process already, if you can have moments when you sort of catch yourself and ask, “What am I good at in this scenario? Where’s my sweet spot?” And then also be able to tell the truth about like “Oh, I’m really not good at this part of this problem or at this part of my business.”

That’s really what we’re talking about when we’re talking about self-knowledge; the ability to think about your own process in real time. When you can do that, when you are someone who can self-reflect pretty well, it means that you have the option or the opportunity to be able to plan around things that you’re not good at. If you know that you are not particularly good at public speaking or you’re not particularly good at marketing or there are pieces of what’s required of you that you’re not strong in, you can invest the time and energy to really learn how to counteract those weaknesses or you can hire help or you can do something about it. But when you go in blind and you’re not paying attention, that’s when you risk sacrificing potentially good outcomes when you risk sacrificing the success of what you’re working on because you haven’t taken the time to stop and think “Oh wait, actually I suck at networking. I need to get better at that or I need some help.”

Rob: So is this a lot about strengths and blind spots?

Sherry: It is, to some extent. Each of the topics that we talk about in that chapter are different continuums.

Chaos versus rigidity is an interesting one. I picked this up from a woman named Filipa Perry who is a therapist in the UK. She talks about how we can organize our conceptualization of mental health along that continuum. You can break at either polarities. If you are hyperchaotic or very chaotic, then you might be somebody who really has trouble following through. Perhaps you are really able to think outside the box and move quickly, but you aren’t that great at communicating what you are thinking to people who are working with you and for you.

Chaos at the outer edges can become very problematic, but if you move in towards the middle of the continuum, there are some real strengths there that are important to know about yourself.

The other side of that continuum is rigidity. Under extreme stress, some of us tend to be very rigid. We need things in a very specific way, a certain way, and we become very anxious when our environment doesn’t align with what we believe we need. That kind of rigidity, on either ends of the spectrum, they look like obsessive-compulsive disorder or an anxiety that is un-wielding or inflexible.

Knowing whether under stress you tend to clamp down and become more rigid or whether you tend to let it all hang out and lose your keys and forget to pick your kids up, and tend toward the chaotic, you can plan around that. Say you are about to launch a new product and you know that you tend to get a little bit chaotic when you are under pressure, you might need to invest a little bit more time in organization, or you might need some extra help, or you might need to think about the things that generally fall through the cracks when you’re under stress and make a plan for them.

Rob: And can it also be not just blind spots that you need to account for, because I think that’s a good point. Sometimes feeling a sense of anxiety or depression and not knowing what it is and finally realizing, “Oh, it’s because I hate this part of the job.” Like unearthing what you love versus what you don’t and being able to then delegate that.

Sherry: Right. It’s always a conversation about strengths and weaknesses. When you realize ” Oh my gosh, this piece of my business totally stresses me out.” Once you have enough money to hire someone, hire someone to do that. Hire someone to do the thing that has the highest emotional pain point because even the most mentally sane person is gonna waste some cycles and spend some anxiety on something that causes a lot of apprehension. If you can have someone do that for you, then that’s gonna save you both the doing of the task as well as the anxiety that goes along with it.

Rob: How about one of the other two dichotomies I mentioned? There was a fixed mindset and growth mindset and introvert and extrovert.

Sherry: I think the same can be true of introversion and extroversion. Those are ways of organizing how we relate to the external environment. If you are introverted, you are pretty attuned to what’s going on inside of your own head. You might be somewhat apprehensive or reticent with a lot of social stimulation. The way that you recharge or refill your emotional bucket, so to speak, is doing things that are either alone or with fairly low-key social stimulation.

Versus an extrovert on the other end of the spectrum who really feeds off of social interaction. That is energizing, they love to be engaged in conversation and maybe animated, outgoing. These are usually the terms that we come to associate with extroversion. Those are both great personalities, right? The strength of an introvert in being able to observe and read a situation, the strength of an introvert in being able to think first and speak later, those are super valuable in the founder world.

But if you need to make that really energetic sales pitch, and that just fairly is not your personality, you have to really gear yourself up. You have to practice extra. You have to have all of your resources about you, whether that’s spending extra time to make a really amazing keynote or whether you bring someone to present with you. Those are the ways that we problem solve around our relative weaknesses.

The thing about knowing yourself isn’t that one way of being is better or worse. It’s that we all are a mixture of skills and abilities and we have to be super honest about what we’re good at and what we’re still growing in.

Rob: I think it has a profound impact on my, I wouldn’t say success as a founder, but it’s more like my ability to become and remain happy as I’ve started these companies and launched all these products. Early on, I remember feeling guilty as I jump job to job every couple of years. My dad told me people are gonna look at your resume, it’s not gonna be a great thing. And then I realized that I don’t like working on the same thing forever. It was just something I learned about myself that I was probably never gonna build a product and keep it around for 10 years. There’s been just a few exceptions in my life.

I think finally understanding that about myself and not feeling guilty and stressed about it when I get 18 months or 24 months into a project and I start really feeling down on it and burned out and all this stuff. As soon as I switch to a new project, I’m just fired up. I know some people who do that every month or two and then you’re never gonna get anything done. But I will see a product to enough success that it makes it worth it and then want to just move on.

Sherry: If you really accept that about yourself, then you would be razor sharp on honing the skills that it takes to get a startup going and then to a certain level where you can just hand it off to somebody else. Hypothetically, you wouldn’t really stress about do I babysit this thing for the next five years. You would just say, “No, this is what I’m good at. This is what I do. I know myself well enough to know that I am not going to retire out of this company.”

Rob: Let’s talk about how you do this. Someone listening to this says, “Okay, I don’t know myself very well.” How do you go about introspecting to the point that you can start identifying things for yourself?

Sherry: I think one of the best ways to do that, to really create space for meta reflection, for thinking about how you’re doing, is to have a practice of going on a retreat once, maybe twice a year, where you satisfy the day-to-day and put down your to-do list, turn off your computer and ignore all notifications and buzzes and beeps and things that often distract your attention. And then, begin to really ask yourself some deeper questions about what have been you successes over the last year; what have been the points in the year that brought you the most joy where you felt you’re most in your sweet spot. And then you ask the opposite kinds of questions. Where did you feel like your life was being sucked from you? Where were you miserable? Where did you feel like you failed? Begin to really look at those questions as an amalgam and look at what does it tell you about what kinds of moments and experiences you’re drawn to and what kinds of things really seem to not go so well for you?

Rob: You’ve thought and written a lot about this. You wrote the ZenFounder Guide to Founder Retreats which is available on Gumroad. I assume you have a link to it from www.zenfounder.com as well. That’s a 28-page ebook and 2 worksheets. You also wrote a bit about it in the Entrepreneur’s Guide that we’re talking about today. That’s a lot of fun, a lot of content on something. It sounds like just based on that, this is a really crucial piece and something that you believe in quite a bit.

Sherry: Absolutely. It’s not just me. There’s some great research behind the benefit of really disrupting your schedule and stepping aside from your normal context. One thing that’s really important about a retreat is you really should not do it in your office. You need to go to the mountains, you need to go to the coast, you need to go somewhere with different sensory cues, with a different environment so that you can let your mind engage the questions of your life in a different way. That’s helpful to begin to vary the ways that your brain is used, sort of like the well-trodden paths that your brain is used to taking. If you can get out of your normal environment, you create a level of environment to a novelty that lets your brain think in a different way.

Rob: That makes sense. It’s taking two days away from the spouse and the kids or just your everyday life, head somewhere. We used to go to the beach. We had the beach apartment and we go there all the time. But other folks I know would go to the mountains, go to the desert, and really just hold yourself up. If I recall, I didn’t even bring a laptop most times. I had my phone in case there was an emergency and I need to check email or something, but I would bring the black notebook with a pen and just start with those questions. Typically, a bunch of stuff fell out right out of that because it was like, “What do I wanna do this year?” Some years it was like well, it’s a year where I’m either acquiring something, I’m going to build something, I’m going to tool around until I find something, or it was a growth year.

It was like whoa, just a second, you’re at Drip. I know I’m not stopping doing that, so how do I wanna get to where it needs to go? How am I gonna do that? Sometimes, it was more about the business. Sometimes, I would have the personal side of thinking about me. Oftentimes, honestly, it was a combination of both.

Sherry: It’s just time to ask those big questions like how am I doing? Am I happy in this life that I’ve constructed for myself? If not, what do I need to do? Those are not those big existential questions, we can’t do that on a day-to-day. We’re busy driving people and answering email and doing the business of our life. We need to step aside to be able to really have insight into those big questions

Rob: The thing is when I would go on a retreat, most of the first day was towards just leaving everyday life behind. It wasn’t typically until late in that day or maybe it was the next day where I would start to have a little bit of clarity about things because it’s like the rest of life went away and left all this room for deep thought, a state you don’t get into everyday, hectic lives of running businesses.

You obviously go into more depth on that in the book. The book is out in the next couple of weeks, as soon as printing is finalized. You cover a lot of other stuff about understanding where you came from, optimize where you’re going, battling the haters in your head, mastering disruption, getting things done when things aren’t getting done and staying connected.

Folks can go to www.zenfounder.com/book anytime to sign up for the launch list. I think the book’s gonna have impact on a lot of people. We really are selling it as a book. It’s gonna be, what, $25? I don’t know if we have the final price, but it’s gonna be $20-$30 bucks. It’s not gonna be some info product where we have all the whiz-bang and it’s hundreds of dollars, this is something that we want to get out to as many people as possible. It’s gonna be a no-brainer for so many of the founders who struggle with this stuff or potentially will in the future and just need a toolbox or just one more piece of knowledge for people to keep it together while doing this pretty stressful thing.

Sherry: Somebody asked me who the book was for. Obviously, it’s a really good marketing question. It’s for humans. It’s for humans who have jobs and are doing things. Obviously, it is geared towards people who are founding something and running their own business. So many of us are looking for strategies to help manage stress and the challenges of our everyday life.

Rob: Yeah, for sure. That’s www.zenfounder.com/book. You also do one-on-one consulting with founders and entrepreneurs, wanna talk a bit about that?

Sherry: I do. That’s one of the things that I have just found to be so rewarding over the last few years is to be a resource for folks who are trying to do some of this how do I get to know myself, how do I become more self- reflective, how do I answer big questions about my life, how do I make decisions when decisions are hard to make? I’m a sounding board, a sounding board with a lot of experience and trained ears to hear potentially problematic thoughts and to spot blind spots and patterns that are counterproductive. I try to come alongside people and help them be as awesome as they can be in their businesses and in their lives.

Rob: It’s totally confidential and that’s something that you’re very good at so I have no knowledge of who you talk to but I do know that you have co-founder disputes that you moderate, you help folks who forgot how to communicate better with their spouse or their family. You’ve consulted founders on how to deal with either a problem employee or a manager to get through struggles with, that kind of stuff. Folks considering selling their company, they’re getting an offer and they don’t know if it’s the right decision. You’re that sounding board where it’s a little bit about advice, but it’s a lot about getting someone to think what is the right answer for them, or just leading them to the right answer when it’s a hard decision and it’s not super clear and someone really needs to dig deep and to think to think about a lot of factors in order to make the decision

Sherry:           It’s a lot about asking the right questions and listening really well.

Rob: Yeah, and it can be super helpful to have someone to just think through decisions now and again. I think that wraps us up for today. Folks who want to get a hold of you, www.zenfounder.com is your home online.

Sherry: It is. If people are interested in my professional background, I also have a presence at www.sherrywallling.com.

Rob: If you have a question for us, you can call it into our voicemail number at 1-888-801-9690 or you can email it to us at questions@startupsfortherestofus.com. Our theme music is an excerpt from We’re Outta Control by MoOt used under Creative Commons. Subscribe to us in iTunes by searching for Startups and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening, we’ll see you next time.


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