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Dr. Sherry Walling on Keeping Your S**t Together as an Entrepreneur

Dr. Sherry Walling on Keeping Your S**t Together as an Entrepreneur

November 21, 2017. By

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Today, on the Early-Stage Founder Show, I’m talking with Dr. Sherry Walling, a psychologist, podcaster, and the founder whisperer behind ZenFounder. I first came across Dr. Walling’s work at a conference where she spoke about what she calls the Owner’s Dilemma.

The dilemma is that with all the freedom you get as an entrepreneur you also have a lot of responsibility, and with how hard it can be to relate those feelings to others, it can be an isolating pursuit.

In our chat today, Dr. Walling shares how to identify some of the common challenges founders will face, how to better prepare yourself for them, and strategies for what to do when it seems like it’s too much to handle.

These are all lessons that she covers in much more detail in her upcoming book, The Entrepreneur’s Guide to Keeping Your S**t Together, but today’s chat is a great primer on the subject.

If sometimes you feel like your business runs you rather than the other way around, then this is the episode for you.

Topics covered:

  • Background leading up to today

    • What is ZenFounder and how did you get started?
  • The Owner’s Dilemma

    • A walkthrough of the fundamentals

      • The responsibility that comes from freedom
      • Poison
      • Immunity
    • How do you know when what you’re going through isn’t normal?
    • What forms of help are available?

      • How can people decide what is best for them?
  • ZenFounder

    • How are you working to help entrepreneurs at ZenFounder?
    • How has your approach evolved over time?
  • Parting advice for founders

    • What is the first step you’d recommend a founder takes to start building their immunity?
  • Where can listeners go to learn more?

Resources mentioned:

Where to learn more:

Dr. Walling is about to release her first full length book, An Entrepreneur's Guide to Keeping Your Shit Together, which is a must read for any entrepreneur. Sign up for the launch list so you can be the first to hear when it’s live as well get a new podcast episode every week to give you specific tips and strategies for different parts of entrepreneurial life.

You can find Dr. Walling herself at ZenFounder.com or @ZenFounder on Twitter.

Transcript:

Andy Baldacci:      Sherry, welcome to the show.

Sherry Walling:     Thank you. It is a pleasure to have this conversation with you today.

Andy Baldacci:      Just so listeners are aware of a little bit of context to this one. I usually cross my fingers and hope that when guest call in, they don't have video on. Sherry did and so I turned my on, and the reason I hope that is because I have, since moving in this new apartment, not have a great spot to record so I'm recording from a closet right now, but that's okay, didn't scare Sherry away so we're still here.

Sherry Walling:     I'm actually really impressed by what looks like a nice collection of feather boas behind you.

Andy Baldacci:      Let's see. Oh, I think it's just one feather boa, but it's a few different colors on the boa.

Sherry Walling:     Oh, it's rainbow feather boa.

Andy Baldacci:      Yeah, yeah.

Sherry Walling:     Extra points.

Andy Baldacci:      I'm not even giving an explanation, just let you wonder why I have that, but anyways, we'll jump in though and so.

Sherry Walling:     Sounds good.

Andy Baldacci:      Sherry, just to kick it off, what exactly is ZenFounder and how did it all come about?

Sherry Walling:     ZenFounder is our answer to the problem of mental health for founders, for entrepreneurs. It got started really in 2013 after my husband Rob Walling and I, had observed just a lot of anxiety and stress and broken marriages and even some suicidal stuff in the founders that we knew and the people that we work with. We realized there really wasn't anyone who was talking about mental health issues for people who are running businesses. It started with some conference talks. It started then with the podcast and now it's become kind of my full time job in that I work with founders as a consultant and as a teacher, pretty much full time now.

Andy Baldacci:      I had known that ZenFounder existed. I knew you had a podcast. I knew this stuff was out there, but didn't really tune in too much, but at Brennan Dunn's DYF Conf. almost two years ago, I heard you speak about what's called, you've referred to it as the freelancer's dilemma. Just hearing you talk, I'm like, "She is in my mind. She knows exactly what I'm going through.", like this is mind blowing to me and it's all kind of clicked and the reason I'm bringing this up now is because freelancers are essentially are entrepreneurs themselves and entrepreneurs go through these exact same emotions so can you just speak a bit more about what this kind of I guess entrepreneur or owner's dilemma really is?

Sherry Walling:     Yeah, I think that most of us become entrepreneurs, myself included because we have an innovative way of doing something or an innovative way of thinking and we also want freedom over our lives. We want freedom to do the kind of work we want when we want on our own terms and really yield the benefits of our effort more directly than when we're working for someone else. That's this wonderful rich motivation that's pretty universal I think among freelancers and founders, but the dilemma of that is the weight of the responsibility for holding together all of these pieces of your life. It's no small thing to run a business, to start a business. It's no small thing to kind of take the reins of responsibility for your livelihood whether it's just you or whether you have a family to support and I think the dilemma is how we balance the freedom we have with the weight of the responsibility that we carry.

Andy Baldacci:      How should people deal with this? Obviously, that's a big question because it's something where there's not just one strategy, this is how you handle this, this is how you do this, and everything's going to be great. It's a complicated thing, but how do you, yourself approach this dilemma?

Sherry Walling:     I think the first step is to tell the truth about it. We can listen to podcasts and read amazing success stories and it starts to feel like this is the dream. If you're a founder, if you're a freelancer, you're living the dream, you don't answer to anybody. The reality is that, that's not true. The reality is that, maybe it's dream like, but there are also some really hard parts of it. First step, I think is to kind of being honest about how much weight we carry and how stressful it is and how hard it is to go out on your own and chart your own territory.

Andy Baldacci:      Right now, I actually am employed full time as most people still see that as this glorious thing, but when it was me out on my own, it's just constantly everyone was talking about how I'm so lucky, how amazing it must be to really be able to take charge and do things my way, set my own hours, whatever and it's like yeah, that's part of it, but there's a lot that comes along with it that isn't so great. Then other than that, you would hear these podcasts and you'd see these stories, these news articles, whatever it was, about people that seem to have it down perfectly and things are so amazing. I don't know why isn't it this easy for me? Why do I have to struggle with all of this to make it work or at least try to make it work, and it's tough so I think you're right, is that just the first step is saying like, this isn't easy. 
                   It is a lot that I have to balance with this, but then once we've kind of accepted that or at least done that, where would you go next? How can we proactively shield ourselves or at least be aware of what can kind of take us off the path, not just the path for a success in terms of business, but in terms of a solid mental health and just health in general around all that?

Sherry Walling:     Yeah, I think we want to be specific about the points of pain so there are a couple of different things that I've observed in founders that I've worked with over the years. One of them is isolation that when you go out on your own, even though you might have a great team, even though you might have a business partner, even though you might have a spouse, you're still carrying the weight of your business within your head in a very specific and unique way and that can make people feel very alone in the work that they have to do and the decisions that they have to make. First thing to tackle is isolation and I think that means finding a mentor, finding a mastermind group, finding a conference that you go to regularly, a community of people who understand you, who have your back, who are helpful, who are encouraging so you don't feel like you are a drift in doing this by yourself. You need a community of people who are cheering you on and helping you.

Andy Baldacci:      Should that be your spouse or should it not be your, do you have like any strong feelings about that?

Sherry Walling:     Yeah, I think you probably need a team. You need like a team of specialist, just like you have like a dentist and a doctor and somebody who cuts your hair. You need a team of people who can provide different sources of support so I know in my relationship with Rob, I am not his sounding board for his business like Drip has grown and done its thing and gotten sold and all of those things independent of my counsel so to speak. He has other people that he talks about marketing with and that he talks about technical things with. I talk to him like any other spouse about how's your day? What made you sad today? What made you frustrated? What went well? Where are you rocking it? I provide emotional support and companionship, but I'm not his mastermind group. 
                   When he's trying to make a big business decision, he definitely talks to me, but he has another circle of people that he talks to, which in our relationship is really ideal because I have my own business to run and I don't totally want to bear the weight of all of those choices. I want him to have other people. It's actually to my benefit and to the benefit of our relationship that I'm not his primary sounding board.

Andy Baldacci:      In my experience, a lot of people who don't have that team, they don't have that community, they don't have that around them, they don't want to burden their spouse with just kind of dumping everything onto the head on them especially when it might not be something where that's, not really specialty, but they're not equipped to really offer constructive feedback and so then you just feel almost more alone. It's like all right, this is the person who I love, who I trust with everything, but I don't want to be this burden on them, so you just bottle it up, but it's having that outside sounding board of multiple people you can go, try to think is huge and so a lot of people talk about finding masterminds, finding people to do this. In your experience, what is a good way of starting that path of actually finding people who can come to fill those roles?

Sherry Walling:     My optimal way to do that is to meet people in person first. This can happen at MicroConf or Double Your Freelancing or a WordCamp Meetup, there are many, many places or conferences that happen of course around the world in the tech space. I think it's important to get in the room with a couple of people optimally because then you have, you get a sense of them. You form a friendship, you form a relationship and that's a nice jumping off point to say, "Hey, do you want to keep meeting?", and meet weekly or monthly or whatever it is that you decide. If that doesn't happen organically, then there definitely are places to go to be connected with people specifically for masterminds so my friend Ken Wallace has a company called MastermindJam that just connects people. People can sign up and they enter some information about who they are and what they're looking and he'll put you in a group. 
                   ZenFounder also host something called ZenTribes, which is for people who are looking to get connected with other people and are thinking about how to be healthy as entrepreneurs and sort of intentionally deciding to be entrepreneurs alongside other people. There are FounderCafe and other things that are available so I really think that it is possible to find a good mastermind and maybe you start and say, "Hey, let's meet for six weeks before we decide if we're going to like sign on together for a long time or let's meet specifically because we're in the same phase of our business and we're going to you know do this next year together and then we're going to move on or at least renegotiate.", so it can be done and I think people can find other people to really be in masterminds with, but you got to decide that it's important and then of course, like everything that's worth doing, it takes a little bit of effort.

Andy Baldacci:      Yup, and it's something where at least for me, I've always been skeptical about, not forced, but it didn't organically come about for the mastermind where you go to someone else to kind of leverage their connections, their service whatever, to find a group to talk with and like if I don't really know these people already, will it really work? At the end of the day, all the people in those groups have said, "This is something that's important to me. I want to change. I want to work on this.", and so just that alone, having a group of motivated people is going to make a huge difference so I think this is some great tips. For listeners, I'll make sure to get a lot of those resources linked up in the show notes. 
                   From my perspective, the isolation was huge and that was in the original talk you gave was what resonated with me the most. It stood out as something where I just, it clicked, okay, this is exactly what I'm feeling, I just never put it into words. I was so glad that you covered that just now, but I know there were a few other, I think as you called them poisons, that were really important as well and so I'm wondering if you could just speak to what those were.

Sherry Walling:     One of the others that I talk a lot about with founders is simply the cognitive and emotional burden of all there is to do when you're launching a business. We can just call that neatly under the category of anxiety. You're carrying a lot, thinking about a lot, worrying about a lot, there's a lot of kind of channels playing in your brain all at the same time. I mean that's universal, that's part of what makes it hard to be an entrepreneur is that you are responsible for everything, for all of the details, from the website design to how things get shipped to interfacing with consultants and other people, and so there are inevitably lots and lots of pieces to just carry. 
                   When we think about how to tell the truth about anxiety, it's of course first and foremost, noticing when it's happening, figuring out what your particular signs of anxiety are and for most of us, they happen in our body. It's an upset stomach or sore shoulders, muscle tension, increased sort of heart rate, feeling frantic or distracted, being snappy, realizing that we are shifting from our normal self to this anxious self that's much less pleasant to be around than the normal self.

Andy Baldacci:      When you're able to recognize some of these signs, when you're able to feel these changes, what do you do then?

Sherry Walling:     Ideally, you'd have some systems in place to help prevent anxiety from escalating. There are very simple, very important ways that we can do that. Simple things like making sure we get enough sleep, not overdoing it with the caffeine, making sure that we're exercising or moving our bodies regularly, making sure that we're eating well. All of those really simple like lifestyle things have a tremendous impact on how our bodies process anxiety. Before anxiety strikes, I think for all founders, I would just want to infuse them with this level of self care and kind of healthy living because that just makes it so much easier to withstand some of the ups and downs of the founder life or the freelancer life that can get really hard.

Andy Baldacci:      That advice of sleep well, eat well, exercise, it's not the first time anyone's heard that, but so few people like truly embody that even at just a simple level of just getting kind of the basics of all those things in place and because they say, "I'm so busy, I don't have time to do that.", and it's just almost a continuous spiral or a cycle where they just get stuck in this rut and so to those founders who say, "Yeah, yeah, I get it, but I'm always in a rush so I don't have time to prepare my own food and eat well. I don't have time to exercise. I need to be productive so I'm going to have six cups of coffee a day and it's going to be hard to sleep at night.", how do you break that cycle?

Sherry Walling:     I think, sadly, it sometimes happens when there's no other choice like when someone gets really burnt out or really sick or has a major failure because they made a dumb decision so we don't want it to get to that point where you have to make some of these changes to your life. I really pair the well being of the business with the well being of the founder. I mean your business can't be healthier than you so if you are not of sound mind, if you are frazzled and tired and fragmented so will your business be and I think I can say that all day and all night, and some type of people sort of nod politely, sometimes they believe me, sometimes they don't, but I do appreciate that I think there are some leaders in the entrepreneurial community who are beginning to really talk about the weight of burnout and depression and the kinds of things that do happen when we don't take proper care of ourselves, but we're under intense amounts of stress. 
                   If you kind of try to cheat your body, I mean you're going to lose like eventually, the sleep will catch up with you. Eventually, the weight gain will catch up with you. Eventually, you're going to hit a point where you have no choice, but to stop.

Andy Baldacci:      It's not as though you're saying you have to be perfect for this, because in a business, even if you have kind of your shit together pretty well and things are running smoothly, there are still going to be times where you have to put in long hours, you have to be working seven days a week, and you have to do things, it's unavoidable, especially in the early stages of a business. 
                   Things might slip. That doesn't mean go to McDonald's every meal and don't get out of your chair and sleep four hours a night, but find some ways to balance it. But really, though, it's my opinion at least, it's trying to make the average day much better, so that when things do get a bit hectic it's not the new normal, it's not just how you're accepting things to be. Does that make sense?

Sherry Walling:     Absolutely. I think we set the normal by kind of a healthy way of living. Then, knowing that there's gonna be ups and downs.It's like we want the cushion to fall back on, rather than to live off, always, like we're reacting to a crisis. 

Andy Baldacci:      There's obviously the actual tactics and strategies of eating better, having better sleep, if you want to get a sleep hygiene, and then exercise and all that, but ultimately the way to get started, I feel that if you are busy, it's just figure out one thing, or how can you ignore one thing that's taking your time so you get an extra 20 minutes, 30 minutes a day and just force yourself to make just one small step. It doesn't need to be change everything overnight. But just get the wheels in motion, and then slowly, as you kind of get back control of things, then keep inching forward and inching forward. However you want to do it, I think it is important that you do make it a real priority. 
                   And Sherry, there's one other poisonous again, as you called it, that I wanted to make sure we touch one, and that was fear. Can you talk about why this plays such a big role in the entrepreneur's life?

Sherry Walling:     Fear is kind of a continuum of anxiety, but I think the fear that is really the, sort of key poison, and I talked about with founders is, the fear of failure, or a way of grappling with failure. And I think, this gets a little more existential, maybe, but we all, as founders, tend to see ourselves somewhat as exceptions. We have to believe that we are the one that's going to make it, or it's our business idea that's going to be successful, even though all of these other businesses fail or don't grow to the extent that we want them to. 
                   I think it's really important to be, again, honest, with our eyes wide open about the possibility of failure, because we do have the power to build some failure resilience into ourselves, so that if or when we are among the many, many founders who are ultimately not as successful as we want to be, we aren't feeling like there's nothing else, like there's nothing else to live for, so to speak.
                   So, when we talk about becoming failure resilient, that really means investing in relationships, investing in other parts of life outside of our business, and I get how hard that is. I get what it's like to sort of have the fever and be all in and in love with what you're doing, and do it 20 hours a day, seven days a week. I get that, but over the long run, you really do yourself a disservice when you pour yourself only into one thing. 
                   None of us are just one thing, and none of us should put ourselves in a position where our mental health sort of lives and dies according to the success of one thing. So it's sort of like diversifying your existential holdings and letting other things be meaningful. 

Andy Baldacci:      Everyone deals with some stress. Everyone deals with some anxiety with the fear of failure and with those types of things. That's never going to go away entirely, but how do you know when you really need to take a step back, because you're king of teetering on the edge of what's normal, what's not.

Sherry Walling:     So, I think the first part of this has to exist as prevention. You have to, as a freelancer, as founder, know the risks that you're taking with yourself, with your well-being and be very proactive about doing some of the kinds of things that we talked about: taking care of your body, managing your anxiety, observing your anxiety, diversifying your life so that you have more things that are just important that just your business.
                   But there certainly comes a point in the lives of many founders when the prevention isn't enough or when prevention fails and we get to a point where we are not doing well. And one of the things that I see most often is burnout, which is this kind of combination of symptoms, where people feel very physically and emotionally exhausted. People feel pretty cynical and detached and kind of withdrawn from their work, and people come to believe that no matter how much effort you put forth forward, they don't feel very effective. They don't feel like things are happening. 
                   So, those are kind of the three components of burn out. And burn out is super bad for our brains. There's just no way to say it. Like, it actually changes the structure and function of our amygdala and our medial prefrontal cortex. They're done studies where they have looked at brains of people who are really burnt out in their job and their job, and their brain is actually, literally changing before their eyes. So, it's a big deal.
                   Also, we see depression in founders. We see founders who are functioning but barely, you know. It's important to realize that many people who do high intensity jobs need help sometimes. It doesn't call into question your skill as a founder or your ability to run a group business to make sure that you are taking care of your body, of course, and then also your of mental health.
                   So, if people are coming to a place in their lives when they observe big changes in energy or sleep or appetite, it might be a good idea to get some help. If you find that you are crossing the line, like yelling at a customer or swearing at one of your kids, just doing something that's not you, that you feel a little bit out of control of your ability to keep your emotions in check. If you feel like it's becoming really hard to shift your thoughts, like you're almost perseverating or thinking over and over about the same things, it can be helpful to get some help. 
                   Certainly, apathy or sadness or that sense of, like detachment or flat mood that's blasting for weeks at a time, that can signal burnout or depression, that's a good time to talk to somebody. Then, of course, if you have thoughts in your head or voices in your head that are talking about hurting yourself or self harm, that is surprisingly common. It is not unusual for people to have thoughts of like, oh, I just wish I wasn't here. I feel completely overwhelmed to deal with this, but those thoughts get specific or loud or have authority, then it's absolutely a sign to reach out and talk with someone who's supposed to walk through that challenge with you. 

Andy Baldacci:      In the business world, it is so common to have coaches for have different aspects of the business, whether it's a consultant for something, or whether it's just a strategy coach, but there still is that stigma of getting help on the mental side of thing. It really is harmful to … The habit stigma, I guess. It really holds people back from getting help when they need it. Other than talking with a professional like yourself about this, what form of help are available?

Sherry Walling:     Thankfully, we are living in a time when mental healthcare is slowly trying to catch up with tech, but there a number of services that are easy to use, from your home. Like Three Cups of Tea is one that is kind of a listening service, of a way of getting connected to people who are equipped to help handle some of these conversations, but, you know, can happen wherever you are, your office, your home. 
                   This is also what we do at ZenFounder. We want to have these conversations with people. We are sort of the coaches and consultants for the mental game of doing a startup, and I know that many folks who are leaders in the tech and entrepreneurial world are beginning to talk very openly about their own experiences of participating in therapy, being a therapist, seeing the coach for mental health stuff. I think the stigma is becoming out of vogue. It's becoming outdated. It's becoming more and more common. 
                   I talked to Rand Fishkin a couple week ago, and he's been super open about his experience of psychotherapy, as has Brad Feld, and Clay Collins and other leaders in the tech entrepreneurial world. 

Andy Baldacci:      I was a professional poker player for eight years and back then, there was what was called mental game coaches, and effectively … obviously, they were focused on making decisions in the heat of the moment and that kind of thing, but at the end of the day, a lot of it was true counseling on different areas of what's going on. Like why are you having these emotions while you're playing? Why is this effecting you like that? And that was not thought of as different, and it seems like when reading over this ZenFounder website, you kind of hit on a lot of these types of things. 
                   If someone is willing to invest in their business in terms of improving their skills in any area, but isn't invested in here, not only are you selling your business short, which matters, but the big thing is your selling yourself short. You're doing yourself a disservice by not prioritizing your own mental health, because it's just going to make things a lot harder for yourself, and just for everyone around you, frankly.

Sherry Walling:     Yeah, I wish that as part of a new business strategy, that was just part of the gig. Like, okay, so you're gonna start a company. What do I need? I need an accountant. I probably need a lawyer. I need some people in the proverbial Rolodex that I can call when I have a question about a specialized issue. And a therapist or a coach can just be that person for that particular part of your business. I would love to just normalize that, so that's just part of your startup plan.

Andy Baldacci:      Right, and I feel like once you start investing in your own mental health and you see the benefits that you get, you're gonna think it was insane that you didn't make the investment early, that you didn't set aside the time or you didn't make a priority before, because it is just that important, so I'm glad that we were able to have this talk and really get a lot of that out there. 
                   If a founder wants to start making some progress towards building up their own immunity toward som of those poisons that are out there or just really taking a first step to taking their mental health seriously, what is a good first step for them?

Sherry Walling:     I don't know if I'm supposed to say, "Give me a call." 
                   I think probably, a great option and we really try to make some of our services affordable to people who are just starting out. But yeah, I think it's really important to at least start with a game plan, of here's my failure resilience plan, here's how I'm going to anxiety proof myself, here's how I'm going to make sure I'm taking good care of myself. I think that we're a good place to start, but I also think that if you are someone who has struggled with significant anxiety or has had a past experience with depression or maybe has an ADHD diagnosis, those are really common things in the founder's space, it's also a good thing to find a local mental health professional, who again can just be on call for you when you need them to be. Finding a therapist can be a little bit tricky, but really, like, all things worth doing, it's worth the effort. 
                   Rob and I recorded a podcast, all about finding a therapist, so we can give it to you, so you can put it in the show notes, because it has some specific strategies and techniques and questions to ask them. That'd be helpful.

Andy Baldacci:      Perfect, and I'll make sure to get that linked up in the show notes. So, I know I've gotten a ton out of listening to you talk with me today, and I hope the listeners have as well. If they have and if they do want to hear more from you, to see what you're up to at ZenFounder, what's the best way for them to do that? And are there any resources that they should check out?

Sherry Walling:     So, I'm super excited to say that we have a book coming out in the next couple of weeks. It's my first full length book. It's like watching a baby. It's like really exciting. It's called An Entrepreneur's Guide to Keeping Your Shit Together. 
                   Yeah, thank you for the title recommendations from my 11 year old. I have no idea where he heard that language, but that's what it's called. 
                   And if people are interested in that, they can sign up for the launch list. We're gonna sell it on Amazon, so it's either be like, you know, it'll be cheap for a couple days, and it will be a very exciting launch, kind of party thing. So, they can sign up at the website, and then we also release a free podcast every week. So, people can follow what we're doing and get specific tips and strategies for different parts of entrepreneurial life by following the podcast. And information about both the book and the podcast is at zenfounder.com. That's also where you can find me if you're interested in reaching out and talking about your specific mental health, founder situation. 
                   I'm Sherry at zenfounder.com and @zenfounder on Twitter.

Andy Baldacci:      Awesome. I'll make sure to get all of that linked up on the show notes. And Sherry, thank you so much for coming on today. It was a lot of fun talking. 

Sherry Walling:     My pleasure, Andy. Thanks so much. 

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