The Psychological Challenges of Being a Founder with Dr. Sherry Walling of Zen Founder

Courtland Allen 7s

What’s up, everyone? This is Courtland from IndieHackers.com and you’re listening to the IndieHackers Podcast. On this show I talk to the founders of profitable internet businesses and I try to get a sense of what it’s like to be in their shoes, how did they get to where they are today, how do they make decisions both at their companies and in their personal lives, and what makes their businesses tick.

Today I’m talking to Dr. Sherry Walling, the creator of Zen Founder. Sherry is an academic and professional powerhouse, with multiple masters’ degrees, a PhD in clinical psychology, and she’s also worked as a professor at multiple universities. She has extensive experience researching and treating the victims of post-traumatic stress disorder. In recent years, she’s taken her skills and her learnings in that area and applied them to help entrepreneurs and their mental health. So this is going to be, I think, a very different conversation than we’re used to having on the podcast. But this is fundamental, important stuff that I don’t think gets talked about often enough.

So, Dr. Walling, I’m excited to have you here and thanks so much for coming on the show.

Sherry Walling 1m 2s

Thank you, Courtland. I am super excited to be here and talk with you.

Courtland Allen 1m 7s

Let’s talk about this path that you took, from studying trauma and PTSD and working with patients, to working with entrepreneurs. I know that trauma is a very serious issue. I think it’s hard to overstate how much of an effect it can have on a person. What, if anything, is the relationship between being an entrepreneur and being a victim of trauma?

Sherry Walling 1m 26s

That’s a really interesting question. I’ve got to be honest, I don’t think that many people have asked me that before. I think they assume that I’ve made a shift. But I really haven’t made that much of a shift. One of the things that I bump up against a lot in my conversations with entrepreneurs is that many, many founders have their own significant stories of early loss or traumatic experiences, that in some ways have shaped their path towards entrepreneurship.

So many of the founders that I work with are themselves survivors of very difficult early life experiences. I think the kind of life-or-death or the high intensity of those experiences in some ways prepares them to be founders. I will also say that the capacity to cope with a lot of intensity is something that a lot of trauma survivors have to get comfortable with. That’s really common in the founder space as well. Lots of entrepreneurs are – they have to learn to navigate high highs and low lows and a lot of anxiety and stress. When people are resilient in the aftermath of trauma, that’s often one of the skills that they walk away with, which serves them very well in the founder space.

Courtland Allen 2m 48s

That’s interesting. You’re saying that the set of skills you develop in order to cope with being a trauma survivor happen to overlap with the set of skills that you need to be a successful and a skilled founder.

Sherry Walling 3m 1s

To some extent, yeah. Yeah. Of course there’s exceptions to all of this but it was this interesting sort of bridge that I took. My work in post-traumatic stress disorder was largely with people who were professionals in the military. Lots of officers, lots of medics, lots of folks who had important jobs in the military and then experienced either sexual trauma in the course of their deployment, or combat related trauma while they were in the military. Kind of from that early career specialty, I worked a lot with physicians, so another set of professionals who, in many cases, have just really hard, hard things happen in their jobs.

So it was this stair step to yet another group of folks. I’m not saying that folks who are building businesses are, like, seeing kids die or experiencing assaults. I’m not making that comparison. But I will say that I’ve always worked with really intense, intelligent, high-functioning, really amazing professionals who are also trying to cope with some significant pain in their lives.

Courtland Allen 4m 6s

It’s definitely not black or white, like you either have trauma or you don’t. There’s definitely degrees and shades of grey, and I think it can be difficult for people who haven’t read about this stuff or haven’t seen a professional to even know if the levels of stress they’ve been through early in their lives are contributing to issues or challenges that they’re facing today. So what are some indicators, or some things that can happen to a professional, that might give them mild cases of trauma?

Sherry Walling 4m 32s

One of the studies that I talk a lot with founders about is the Adverse Childhood Experiences Study, which was a study that was done about ten years ago, maybe a little more than that now, that looked at 17,000 people. It was conducted as a partnership between the Centers for Disease Control and Prevention and Kaiser.

They looked at all these health records and they interviewed people and asked them about ten categories of early life experiences, adverse childhood experiences. Exposure to physical abuse, sexual abuse, physical neglect, emotional neglect, having a family member incarcerated, having a parent who does drugs. There’s this whole list of things. One of the things that was on the list was parental divorce, which is not necessarily a trauma with a capital T, but can be quite adverse, can be a pretty troubling experience for a child depending on when and how that happens.

They looked at these ten categories of things, and the research results are very compelling in terms of the relationship between early life adversity and later health outcomes. These are not just things like PTSD although certainly depression, suicide attempts, substance abuse, all were highly, highly related to the number of adverse childhood experiences a kid reported, or an adult reported retrospectively. Things like heart disease, certain kinds of cancer, obesity, kidney problems. All of these preventable, to some extent, health outcomes were related to these early life experiences.

So I think sometimes when people hear trauma, they think about a sexual assault. Of course that’s one of the most traumatic experiences that someone can have in their lives. But there’s these whole host of other things that can shape the developmental trajectory of a kid, who of course later becomes an adult, in this case a founder, and shape the way that their body processes stress, shape the kinds of choices that they make to try to regulate their emotions and reaction to being upset. There’s this tower of dominoes that gets set into play that happens both on a psychological and a physiological level that’s very much shaped by hard things that happen to us early on in life.

Of course this is all very situationally and contextually dependent. So kids who have a really hard upbringing do really well if they have a couple of great, important, supportive adults. In the absence of any supportive adults, those kids of course struggle much, much more both psychologically and physically.

Courtland Allen 7m 11s

So let’s say that you’re listening to this and you’ve had just a golden childhood. Your parents were supportive, they were present, you didn’t deal with any of this sort of stress or trauma-inducing events early in your childhood. Do you still need to worry about mental health? Is any of this relevant at all? Or are you pretty much good to go? And also, are you at somewhat of a disadvantage compared to founders who’ve been through these things?

Sherry Walling 7m 36s

Sorry. You’re not good to go. [Laughter.] I mean, so much of the conversation about mental health, at least the way that I like to have it, is about prevention. It’s about knowing that, to be honest, any of us have our own vulnerabilities. Whether that’s in our personality, in the way our body responds to stressors, in our own history of our psychological hurts, or the bumps that we’ve experienced along the way, very few people have an absolutely pristine life experience.

If you have had that kind of golden child experience, in some ways you might be ill-equipped for things that founders experience all the time, like a lot of criticism, like disappointment, like failure. If you haven’t had a scrappiness to your upbringing, there might actually be some skills that leave you vulnerable to mental health problems because you might be maybe less resilient in the face of adversity.

Courtland Allen 8m 36s

One thing that can be hard for founders is when we’re making bad decisions based on these sometimes very subtle emotions or psychological issues. A good example is, I talked to Saronyit Barek. She’s the founder of CodeNewbie. She had this great insight a few years into her business, where she realized that in a lot of the decisions that she was making, she was optimizing for making herself feel better and making herself feel more accomplished, rather than optimizing for making her business more successful.

Or another example is if, say, you’re a programmer. You might focus on programming tasks, because at least you know what you’re doing in that realm and you can feel good about it. You get these little shots of positivity. You might end up avoiding all these other important tasks for running your business, like sales and marketing.

If you don’t even realize that you’re making decisions this way, it can be really hard to fix. Is there anything that we as founders can do to be more aware of these underlying emotions that drive our ability to make good decisions?

Sherry Walling 9m 34s

It’s such an important conversation to have, to recognize the deep entanglement between who you are as an individual and who your business is as an entity. For most founders, those things are not easily separated. That means that as your business rises and falls, as there are highs and lows, so goes your emotional life. So goes your sense of your self and your identity.

The ability to be very carefully self-reflective about the things that you’re avoiding, about recognizing the difference between what your business needs and what you need, about counter-balancing that deep relationship that many founders have with their business, to try to diversify a little bit, to try to buffer yourself from the roller coaster so that your value as a human being isn’t exclusively tied to the bottom line of your business.

Courtland Allen 10m 38s

I know it can be pretty easy to under-estimate all this stuff as a first time founder. But in your experience working with more experienced founders, do they struggle just as much, or do they naturally get better at dealing with it over time?

Sherry Walling 10m 50s

I think it’s really hard to get a grasp on that. I think even really well-established founders have a difficult time really appreciating the depth of that relationship. I usually see people really battling with it when they are approaching an exit. So highly successful founders who are ready to sell their business and ride away into the golden sunshine are realizing how very hard it is to extricate themselves from who they’ve become in relationship to their business. They and their business sort of become one, and so when you sell the business, it can cause this pretty deep crisis of identity.

Courtland Allen 11m 29s

We’re talking a lot about the risks of you as a founder identifying too closely with your business. But I think some might say that’s actually a good thing, that it helps you become more successful. What are your thoughts on that?

Sherry Walling 11m 40s

I think in some ways, it’s fantastic. You’ve found something that you’re pouring yourself into. There’s actually a research study that looked at the neurological activation that happens in a founder’s brain when they are looking at a picture of their child versus when they’re looking at an image of their business.

The neurological activation is really similar. The areas of the brain that regulate positive emotion, sort of the blissfulness of love, are highly active in both scenarios, the kid scenario and the business scenario. And then the parts of the brain that are responsible for critical assessment, for critical evaluation, are pretty inactive. They’re repressed. So both as parents and as founders, we’re super biased towards our business. We have that “love is blind” phenomenon happening.

It’s great in that it’s fun. It feels good. It feels good to be attached to something that you’re making. To put yourself out there in the world, I think it has a lot of benefits. But I also think that when you have limited resources within yourself and you put all of those resources in one activity, that does become somewhat – fairly – psychologically dangerous. Because of course our businesses don’t always work out well. They do rise and fall. If we don’t have other parts of us that can also be important and meaningful, then we give a little too much power to our business to regulate our sense of worth and well-being as a human. I love my business, but I need to have a separateness from it in order to be well.

Courtland Allen 13m 31s

Let’s talk about that, because I love that not only are you an expert on these psychological issues, but you also have your own business and you’re a founder yourself. So what is Zen Founder exactly, and what made you decide to start it?

Sherry Walling 13m 45s

Zen Founder is a combination of different things. It began with a podcast that I co-host with my husband Rob Walling. We started doing that after – I gave a couple of different conference talks about mental health in entrepreneurs, mental health in founders. They were really, really well received. I gave those talks in response to a couple of high-profile suicides within the founder community.

Rob and I both observed that we had a number of friends in our entrepreneurial circles who seemed to not be doing well. Who were struggling with depression or having difficulty in their marriages or their key relationships. We thought, “OK. I’m a psychologist. I know a little bit about this. Maybe I can be helpful.”

From that thought, I gave some talks. From the talks, we started the podcast, which really addresses more traditional mental health topics as well as prevention, how to stay well and healthy in your family as you’re running a business. We try to be fairly holistic with that. Then that has created opportunities to do one on one consulting. So I meet with founders individually, usually by Zoom, and try to come alongside and help them problem-solve mental health problems in their lives. So it’s not exactly therapy, but it’s more consulting. “Hey, keep an eye out for this,” or “Have you noticed this pattern in your relationships with the people on your team?”

We recently published a book called The Entrepreneur’s Guide to Keeping your Shit Together, which is a culmination of a lot of that material. Things that we’ve developed on the podcast, things that I talk with founders a lot – that I talk with about one on one. We’re tried to pour that into the book so it’s this easily accessible things to think about as a founder related to mental health and well-being.

Courtland Allen 15m 43s

That’s a lot of stuff.

Sherry Walling 15m 44s

It’s so much stuff. I also do some group consulting and, you know – we could talk about my unfocused business. But basically, [Laughter.] yeah, I want to have as many conversations as possible about how to stay sane and well and still kill it in your business.

Courtland Allen 16m 1s

Was there a point during this process where you decided this is more than conference talks, this is more than a podcast, but this is an actual business that I want to be profitable and that I want to make my living through?

Sherry Walling 16m 12s

That transition really happened about two years ago. My story runs somewhat in parallel to my husband’s, obviously. He was the co-founder of Drip. Drip was sold about two years ago. As part of the acquisition arrangement, we moved from California to Minnesota. So I left my clinic job and my teaching job in California. That was a nice, natural transition for me to have space and time to build Zen Founder and to make that more of the focus of how I was spending my time and energy.

Because I’ve been living with a founder for the last 18 years, I realize that, as much as I love academic work and loved a lot of what I was doing, I also caught the founder bug a little bit and wanted a little bit more freedom and a little bit more decision-making power over what my life looked like. It’s been about two years that Zen Founder has been my primary focus and vocation.

Courtland Allen 17m 11s

That goal of wanting to have control over your income and wanting the freedom to work on the things you want, at whatever pace you want, on whatever schedule you want, is pretty much universal, at least among people who decide to become founders.

What was your initial vision for Zen Founder as a business? Did you expect to generate revenue through advertisements on your podcast or through speaking engagements? Or did you just let your business model fall into place over time?

Sherry Walling 17m 37s

I’m not even sure I have a grand plan now. [Laughter.] But I think I do a lot of going where I feel like I’m needed. Which is not the best business model, but I think there’s a little bit of a missional focus to Zen Founder that is maybe different than a SaaS business or something like that.

I knew that I wanted to write a book. That’s been on my bucket list for a number of years. So that was something that was central. Part of the end game is growing as an authority and as someone who’s the go-to when folks are like, “Wow, I’m really having a hard time. Or someone on my team seems depressed. Where do I go? How do I figure out information from someone who gets the founder life but is also well-trained, not just my wise Aunt Nancy or something?”

It’s more about building a brand and the recognition of, you want to talk about mental health in the tech space, I’m your person. I know how to do that.

Courtland Allen 18m 35s

Let’s talk about that. A lot of people start a business and they launch it, and nobody shows up because they haven’t taken the time to really build an audience or a following first. They really don’t know what that process looks like. So I’m curious how you’ve gone about doing that for yourself. How do you think about making sure that people who’ve never heard of Dr. Sherry Walling find out about you and come to associate you with the things that you want to be associated with?

Sherry Walling 18m 58s

I so a lot of conference presentations these days. That’s a great way to have a high-impact interaction with a large number of people. When you see someone speak or when you meet them at an event, there’s a kind of quicker, deeper connection that you have the potential to build. Guesting on podcasts, talking to folks. It’s definitely a word-of-mouth business. I think everyone that I work with individually as a founder, I’ve either met in person or has been a referral from someone else who I work with.

Courtland Allen 19m 31s

So you’re doing it right now. You’re marketing by coming on the podcast.

Sherry Walling 19m 35s

Right now, this is a marketing activity, I guess. [Laughter.] But I think so much of this conversation is about trust. “Can I trust you with the things that I am nervous about?” So many people in our communities don’t talk to a mental health professional because they are worried about stigma, or they’re worried about people thinking that they’re crazy. Or they’re worried that if they have a problem that feels unsolvable to them, that they’re a failure in some way. There’s so many barriers to having a hard conversation with someone you don’t know. So part of my job is to be out there in lots of different ways and establishing trust with as many people as I can to make it easier.

If people don’t come talk to me, that’s absolutely fine. But to know that there are mental health professionals who are not crazy, who are actually approachable and helpful and interesting, that’s a big part of what we’re trying to accomplish with Zen Founder as well.

Courtland Allen 20m 31s

I see a lot of this with IndieHackers too, because part of the mission for IndieHackers is to get founders talking to each other about all sorts of business challenges. It’s not just limited to very practical things like how do you market and find your first customers. But a lot of it is psychological as well.

Some of my favorite conversations that happen online on the IndieHackers forum are when somebody says, “Hey, I just wanted to write a post and let you guys know that this is really hard. I’ve been struggling with my business for weeks or months or years and I haven’t gotten anywhere, and it’s tough.” I love when people make posts like that and others come in and say words of support.

What is the appropriate reaction when somebody shares that kind of information, and how can founders do a better job helping each other?

Sherry Walling 21m 11s

One of the things that we all need to be probably better about is really listening. Just because someone is coming to a group and saying, “I’m struggling,” it’s really important to listen first. All of us have lots of good ideas, but one of the most powerful experiences that is most helpful to people is the experience of being known and being heard. I would like to see that be a little bit better in a lot of the communities that I bump up against.

It’s not so much, “Are you exercising? Are you backing off the caffeine? Are you sleeping well enough? Have you talked to a therapist?” All of those things are really great things to suggest, but first you want the person who’s like, “Hey, this is hard,” to know, “Yes, absolutely it’s hard. You’re not alone in that. I hear you. I get what you’re going through.”

Courtland Allen 22m 5s

I’ve heard similar advice in relationship therapy and counseling, or if someone comes to you and says, “This is my feeling,” to – just how effective it can be to just repeat back to them what their feeling is, so they know that you heard them and you understand them and they can feel validated in that way. Sometimes that’s all it takes.

Sherry Walling 22m 21s

Yeah. I think if you’re going to give great advice, it’s best to ask, to be like, “I have a couple suggestions for you. Do you want my suggestions, or is it more important that I just listen to you right now?” I think that’s a question that we don’t ask enough. People are quick to dole out strategies and advice. It’s not often the right time.

Courtland Allen 22m 44s

You mentioned that you had always wanted to write a book. As part of your business you were actually able to do that. In your book, you sort of distilled a lot of the lessons, a lot of the conversations that you’ve had doing one on one consulting and during your research as well. What are some of the biggest issues that founders deal with?

Sherry Walling 23m 1s

One of the biggest issues is really, in some ways, what we’re talking about right now. Loneliness. I think people feel really isolated. Whether they’re just starting out and they’re working in their basement, or whether they are leading a team of 45 people. I think when you are the person who’s making the decisions, when you are the person who holds the vision for the company, it’s very lonely. There are lots of barriers to trusting other people with your journey and with what you’re really thinking about and worried about. I would say loneliness is a top one.

Another thing that I end up talking a lot with folks about is fractured attention. This can be going through a day where you are simultaneously trying to respond to Slack and email, and watch for something that you’ve just posted on Product Tent * and – I feel like a lot of founders are cognitively all over the place in a way that, over time, causes some significant damage to our ability to focus and be present and just do one thing well. Some of this is nicely articulated in Cal Newport’s book Deep Work, which many of my founder friends seem to really struggle with.

Courtland Allen 24m 22s

One thing that’s interesting is that, if you look at what entrepreneurs are talking about, if you go to the IndieHackers forum or if you go on Twitter, a lot of it is psychological in nature. But none of us are psychologists. None of us really know what we’re talking about.

So, for example, one of the big topics that comes up over and over again is motivation. How do you stay motivated? How do you keep working on your business when the going gets tough, when you get busy, when things get hard or when you lose interest? It’s a big one, because ultimately most businesses fail because their founders quit working on them because they lose motivation early on. How do you think about motivation in your own business, and what do you see that works well for the entrepreneurs that you spend your time talking to and counseling?

Sherry Walling 25m 2s

I am a fan of habits and good old-fashioned self-discipline. I think some things that help with forming good work habits are what we call context cues. You have work space. You have work times. You have kind of a work ritual that helps your mind know it’s time to shift. It’s time to focus on these particular topics and this kind of question.

As opposed to, like, working in your bed first thing in the morning when you’re not quite awake, or trying to work on your phone while you’re waiting for your kid to finish up their basketball practice. But really carving out time and space that is work time. People have different approaches to this, of course, but I think that in some ways, the more structured the better. Putting your email time on your calendar so that it doesn’t – it’s not amorphous, it’s not always an option. You check email from 11 to 12, or a couple times a day. You have a schedule and a routine and your brain and your body sort of know what it’s supposed to be doing at any given time, because it’s habitual.

It’s also helpful to shift those habits every now and then. So it’s not like you set one pattern and that’s the case for the rest of your work life. But to have seasons where you work in the same place, you maybe listen to the same soundtrack. You have these cues that say, “OK. It’s work time.” The environment around me as well as the environment within me are focused on work. Which kinds of takes your emotional motivation out of it to some extent.

Courtland Allen 26m 42s

One of the things that I’ve used myself, tangential to this, is this concept of external pressure. When I first started IndieHackers, what I would do every single week is, I would email my mailing list. I wouldn’t just say, “Here are the new interviews,” but I would also talk about what I’m doing with my business, what my plans are, what I accomplished in the last week. It became this incredibly stressful exercise.

I eventually stopped doing it. But it was a lot of pressure every week to make sure that I had accomplished something that was good enough to write to my newsletter about. On one hand, it was effective, because I ended up doing a lot more work than I otherwise would have done. On the other hand, it was incredibly stressful. How do you think about the balance between doing these things that make you more effective as a founder but that also take some sort of a toll on you?

Sherry Walling 27m 25s

I love that kind of practice, especially for a time-limited segment. Where you’re emailing your list every week for three months, then you shift to a different external pressure. I think sometimes we develop these structures that are designed to help us stay motivated, but we hold onto them maybe too long. We don’t give ourselves the space to renegotiate “What am I really after right now, right here? How am I growing, or am I still just doing the thing that got me to this point?” Sort of that “What got you here won’t get you there” phenomenon.

Most people function well with a significant amount of stress. There’s this old psychological finding called the Yerkes Dodson Principle, which is your standard bell curve or your normal distribution curve that looks at the relationship between stress and performance. For tasks that we’re pretty proficient in, a medium amount of stress is linked to high performance. That’s the pinnacle of our performance.

Too little stress, no stress, no pressure, it’s like nobody cares. You’re not motivated. Nobody’s watching, there’s no fire under you to get things done. But your performance quickly drops significantly once that amount of stress crosses over that middle point, and it becomes so much stress that your performance rapidly declines because the system is flooded with stress, essentially.

You have to be super savvy about being able to read how much stress is the right amount of stress for you, then making a shift when it’s becoming too much or too little.

Courtland Allen 29m 11s

Yeah. This is why it’s hard to be a founder, because you have to not only be savvy about your business and the decisions you’re making and whether or not they make financial or marketing or product sense, but also manage your own psychology and understand – like you just said. How much stress am I under? Is this the optimal amount of stress? Is it too much or is it too little? Is that hindering my performance?

Sherry Walling 29m 30s

It’s a moving target. [Laughter.] Right? You can figure it out one way for six months, and then you have to change.

Courtland Allen 29m 36s

Exactly. On that note, what do you think are some of the differences between being an early-stage founder and a later-stage founder? Because I know that as an early-stage founder, very often nobody knows what you’re up to. It’s only you who’s sort of motivating and pushing yourself along. Whereas, as you mentioned earlier, if you’re a founder trying to negotiate an exit, or if you have a large team, everything you’re doing is very public. People depend on you and it’s a different sort of job.

Sherry Walling 29m 59s

I think early stage folks – there’s like a high scrappiness quotient, just high energy, high excitement, lots of passion, somewhat impervious to disappointment. Hopefully, at that phase, if you are able to do some really good long-term planning, you have a good plan. But I feel like early stage founders are surviving on adrenaline and excitement and good ideas.

And then as you mature as a founder, that decreases a little bit. You have some wins, hopefully, that keep you in the game, but you also have some discouragements. You have more of a community that supports you that understands what you’re doing, but you also have time to develop some competitors and some frenemies and some people that you have more complicated relationships with as you go on in the founder circles.

So I think each sort of developmental phase of being a founder has its unique strengths and its unique weaknesses, and you have different assets at one point in the journey than you do at the other points in the journey. When you’re operating early on, you might not have much money to play with, especially if you’re bootstrapping. But later on in the journey, maybe you have more funds and you can hire more people. But that, of course, introduces more and just different problems and challenges to your work life.

Courtland Allen 31m 19s

Let’s talk about some of the psychological challenges and hurdles that you’ve had to get over in running your business. Have you ever encountered any of these problems that you spent your time counseling other founders about?

Sherry Walling 31m 29s

Absolutely, yeah. One of the times when I really felt my own – I don’t know how to say it – when I was like, “Wow, I need a me to talk to me about this” – (laughter).

So when I finished the book, I got up the nerve, the gumption, whatever, I had a moment where I was like, “I wonder if Seth Godin would write an endorsement for this book. Wouldn’t that be cool?”

So I emailed Seth and I gave him a couple sentences about the book. And he responds right away and he’s like, “Send it to me.” I was like, “Are you serious?” I was so excited. And he wrote a really lovely quote that’s on the back of the book, just a very amazing endorsement, and I was riding high. I was like, “Oh, my gosh. I’m going places in the world. This is so exciting.”

And then we get to book launch day and I’m so excited about the book. And both Rob and I emailed our lists. Rob is the second author on the book. And so the email about the book goes out to more than 20,000 people.

And despite our best careful efforts, the link to go buy the book was broken in the original email. And I was like, “I have no business here, I should not be doing this. If I can’t even write an email accurately, who is ever going to take me seriously as an entrepreneur?”

So it was just this really high and really low, and all the voices in my head that went from, “This is so awesome” to “You need to go crawl in the closet and hide the world, because clearly, you don’t know what you’re doing and you’re really terrible at this.”

Courtland Allen 33m 8s

Right.

Sherry Walling 33m 9s

So I don’t get to be an exception to those highs and lows. And I also definitely – I feel like I really read people well and understand people. But the more that I work with other people and grow my team, the more that I learn that I’m actually not very good at communication, that I’m not super detail-oriented in my instructions. And so I’m learning all kinds of things about my own self as I grow Zen Founder and learn how to try to put together a thriving business.

Courtland Allen 33m 39s

What are some of the things that you think you started out bad at that you’ve gotten better at?

Sherry Walling 33m 44s

I’ve definitely gotten a lot better at doing things in public. That’s hard at the beginning. I remember the first few podcasts that I recorded, I went and re-recorded things, and I was just completely neurotic about making sure that everything was mapped out. And now that’s okay now. I’m confident about just getting out there and trying; that’s become a lot easier. So doing things in public is definitely something that started out hard and is much easier.

Courtland Allen 34m 15s

Let’s dive into that for a second.

Sherry Walling 34m 17s

Yeah, sure.

Courtland Allen 34m 18s

Because I think a lot of entrepreneurs are in a situation where they’ve maybe built something, and the only thing holding them back is that they’re afraid to put it out there. They’re afraid about how it’s going to be received, and they convince themselves that it just needs one more feature or just one more redesign, and then it’ll be good enough because they just are worried about what’s going to happen when they start talking about what they’ve done in public.

And obviously, this is terrible for your business because you need to be able to promote yourself and promote what you’re working on if you really want to get the word out there. You’re not just going to build it and have people magically show up.

How do you get over that hurdle, and how do you get to the point where you’re psychologically comfortable sharing what you’ve done with the rest of the world?

Sherry Walling 34m 52s

I think the best way to do that is to just practice as much as you can. And that means starting at local meetups and it means pushing yourself to, whether it’s speaking at your local WordCamp, which if you do anything with WordPress – there are places to kind of get some practice that are lower stakes, lower-dollar investment.

And then I think you’ve got to have a feedback loop. You have to have a couple people who you ask to give you careful, thoughtful, constructive feedback who you really trust.

And one think that continues to be hard for me that I know is important is actually going back and watching a lot of videos of me talking, or I do listen to my own podcasts so that I can do some self-assessment.

That still feels somewhat awkward. But I do think it’s important because every time I hear mannerisms or I see things that I’m like, “Oh, this would be more polished if I didn’t do that, if I didn’t say that particular catchphrase or if I didn’t have that particular space-filler.

So practice, practice, practice, have a feedback loop that you trust, and then I think growing in your ability to take risks and be creative over time. So I give very different kinds of talks now than I gave when I first started, when I memorized everything and was really, really careful. Now I’m much more comfortable just speaking off the cuff for better or for worse.

But it allows me to accomplish a lot more in less time, not because I don’t plan or don’t think ahead, but because I’m just more comfortable with what I know is already in my mind and my ability to recall it.

Courtland Allen 36m 34s

Yeah. I’m a huge perfectionist with anything that I put out publicly, and it definitely slows me down. It’s a really difficult habit to get over.

Sherry Walling 36m 41s

Yeah. And I don’t know how much it matters. I think if you were to really look at the body of my work – the podcast, anything I’ve written, talks that I’ve given, things that Rob and I have done together – you’re going to see a lot of consistencies. You’ll see the same message show up, you’ll see the same, I think, sort of human approach. The things that I value come across in my work. And you’ll probably see some of the same mistakes or foibles or inaccuracies in some ways.

And I got to hope that at the end of the day, there’s some benefit of the doubt when you just keep showing up and you try to be in as many places as you can that, hopefully, people are gracious enough to overlook your “ums” or your slight mistakes to really hear the heart of your message. Maybe I’m an optimist in that way, but that’s what I’m banking on at least. My stuff is not perfect, not by any stretch.

Courtland Allen 37m 41s

Yeah, I don’t think anybody’s stuff is perfect, even the perfectionists out there.

So what are some of the other challenges that you faced psychologically with your business? Because I kind of stopped you after this first one.

Sherry Walling 37m 51s

I will say that a lot of the process of selling is challenging for me. Self-promotion is hard. That’s not easy. I think, like many founders, my work is closely tied to me, to who I am as a human. So hearing criticism is hard. It’s still hard.

And I think I’m still finding my place in the world in the sense that I bridge these two disciplines. I’m a psychologist who works a lot with tech folks, but I’m not a technologist. So always I feel a little bit like I’m the outsider, which has its benefits for sure.

So I guess I’ll say, Courtland, I don’t feel like I’ve come to this point in my career with lots of boxes checked off. I feel like the thing that I have done by this point is to be self-reflective enough to know when a particular vulnerability or sensitivity is getting activated, and hopefully, faster at catching it and knowing what to do about it than maybe I was earlier on.

Courtland Allen 38m 58s

How do the rest of us do that? Because I think it could be very easy for these feelings to sort of exist below the point of perceptibility and then to just sort of magically appear one day. It’s easy to not know that you’re burning out until you’re burned out. It’s easy to not know that you’re afraid to launch until six months have gone by and you haven’t done anything.

How can the rest of us develop the same sort of psychological sensitivity that you have and catch these things before they start to get really bad?

Sherry Walling 39m 23s

I think there are two areas where you want to collect data. One is to really pay attention to your physical body. Sometimes our emotions exist in our bodies before they exist in our minds in a way. So if you’re someone who sleeps pretty well but you’re not sleeping well, then it’s a really good indicator that your anxiety is too high or you’re bothered by something.

If I’m in a conversation and I find that my throat is tight, I’m not breathing very well, that the muscles in my throat and chest seem to be contracted, then that’s a sign that, “Oh, something is funky here. I’m either having some complicated feelings or I’m stressed out.”

So each of us have our own physiological indicators that something is not well. And again, for most people, that’s sleep, it’s muscle tension, it’s constriction in our throat or soreness in our shoulders. It sort of says, “Wow, I’m clenched. I’m holding something too tightly.”

So paying attention to those kinds of things can be super helpful. I also think that paying attention to your own emotional nuance. I generally like people. I don’t feel particularly defensive or judgmental. I generally like people. But when I’m finding myself having some negative thoughts and feelings about someone else, I have to sort of pause and ask myself, “Why am I bothered? What am I reacting to in this person that is causing me to think or to feel this way?”

So you become this sort of investigator of your own inner world. But first you do have to pay attention to the cues that sort of signal little, tiny red flags. Once you see those red flags, then you can do some investigation. And that’s where something like a journal is a really powerful tool, to write on a piece of paper, “Why am I bothered by my conversation with Courtland? What am I holding onto?” And just give yourself some free emotional space to try to sort through why you might be feeling the way that you feel about that particular incident or event.

Courtland Allen 41m 41s

“Dear journal, that Courtland guy is a real asshole.” (Laughter.)

Sherry Walling 41m 44s

I got to go journal. (Laughter.)

I also think that that’s another place where having a coach or a therapist or a very learned listener in your life can be a really important asset for you to just open a conversation and say, “I’m feeling a little funky, I’m feeling off, and I’m not sure why.” And they can kind of help you try to unpack why you might be feeling that way.

Courtland Allen 42m 13s

So let’s talk a little bit more about your particular business. Do you ever worry about the scalability of what you’re doing? I know you said you’re not a traditional SaaS business, you’re a little bit more mission-driven, and you’re providing a lot of personalized help to people, which I think is very high in terms of impact.

But also there’s only one of you; there’s only so much Sherry to go around. How do you think about balancing the number of people you want to reach with your business and the level of impact you have on each individual who comes into contact with Zen Founder?

Sherry Walling 42m 45s

Yeah, it’s something I think about a lot. Because at the end of the day, I don’t want to spend my life trading hours for dollars. I’d like to have something that has some scalability.

And so I kind of think about it like a pyramid, the one-on-one consulting being at the top. That’s the highest dollar. It’s also the highest impact, but it’s time-limited. It’s limited only by what resources I have available to give to someone.

And then underneath that is some group consulting, leading a retreat, doing an event. That impacts more people, but it’s still a big draw on my time.

And then you go kind of down the cycle. And down there is blogging, it’s the podcast, it’s writing, it’s things that aren’t necessarily deep, high impact between me and one person or me and a small group of people. But it’s putting the word out there, it’s getting good material out there to a much broader audience than I could ever hope to interact with one on one.

So I think as we are moving forward, we’re also thinking about some ways to develop some courses and things that are easily accessible to folks that don’t require the cost and time intensity of doing a round of one-on-one consulting with me.

Courtland Allen 44m 4s

Yeah, I think it’s an interesting approach because a lot of founders come into this with the end goal in mind right from the beginning. And so on day one, they’re trying to launch some sort of infinitely scalable SaaS app that’s going to make money on its own while they sleep. And that’s hard to start off with.

And I think the path that you’ve taken, which is a lot more hands-on, a lot more sort of hourly at least at the beginning and then gradually shifts towards something that’s more scalable, is probably the more realistic path.

So are there any bumps in the road, any sort of unexpected challenges that you’ve run into there that you would advise other founders to watch out for if they decided to follow in your footsteps? And also is there anything that’s good about the way you’ve done things that you think others should copy?

Sherry Walling 44m 47s

Yeah, I’ll speak to the second question first. At least for me – and this is, I think, highly dependent on the kind of work that I do – the day that I stop doing one-on-one consulting entirely is probably the day that people should stop listening to me.

My deep expertise comes from the practice of really going deep with founders and listening well. And if this becomes too academic and I am so much about product that I don’t have time or energy to do a deep dive with at least some people, I think that that will severely decrease my authority and my ability to be effective. It puts me too detached from my customer, so to speak, which again, for my business, for what I’m trying to do, is deeply important.

And I know that can look different in different businesses, but it’s the CEO who occasionally a support call, because you just have to be able to be in a place where you can really hear the deep needs of your customers and appreciate the challenges that you’re experiencing. So it’s like you never want to get so removed from where you started that you really forget about the thing that started you off in the first place or the needs of the people that you’re serving.

I don’t need the income so to speak, but I feel really strongly that the consulting piece continues to be really important to who I am and what I’m able to provide.

Courtland Allen 46m 23s

I think that’s something that should be universal to every founder in every business. You always want to stay very close to understanding who your customers are and what it is that they want. And I guarantee you that if your business is successful, there is a point where you understood that stuff very well in the beginning.

But it’s easy to lose track of it over time because the realities of your company start to build. You’ve got urgent bugs that need fixing. You’ve got features that you need to take care of. You’ve got all sorts of things that have a very obvious and immediate payoff if you work on them, whereas talking to your customers and staying in touch with their needs and their desires doesn’t seem to have this immediate payoff, and so you can neglect it.

But then over time the world can change. And you look two or three years later and what your customers want is different, or your skills and your knowledge have deteriorated and you’re making these asinine decisions for your company and your business.

So it takes a lot of discipline to do, I think, what you’ve done and make sure that you stay in touch with your customers and you keep talking to them even when your business is pretty mature.

Sherry Walling 47m 17s

It also keeps me really close to the heart of what I love. I always feel for the designers that are so successful that they move out of actually designing anything. And often they’re fine that. It’s a calculated choice, but for me, I think running the business without the kind of deep connection with a couple of folks or at least a handful of clients would take me too far away from my personal superpower and what it is that kind of gives me life in my work.

Courtland Allen 47m 49s

So what are some of the things that are perhaps difficult about trying to transition from a more consulting-based business and do something that’s more scalable?

Sherry Walling 47m 57s

Oh, I’m kind of all over the place. I think that’s the challenge is there are so many things that I’m trying to hold up at any one time. So do writing, promote a book, I just blog twice a month, keep up with a weekly podcast. It’s just sort of the number of things that I have my fingers in in any given week is definitely a case for not being particularly focused or not being particularly awesome at anything. So I’d add to that, of course, parenting children and being a wife and trying to have friends and stay in shape and all that stuff.

So I think in some days if I could just do one thing, if there was only one component to my business, it would be so much better for my sanity. But alas, that’s not how it’s going to work for me as I add different components and build out different things. There are just a lot of growing pains.

And I think for me, as with many founders, that growing pain look like fragmentation. It’s just not as focused as I would ideally like it to be.

Courtland Allen 49m 2s

So you’re trying to get your business moving in the right direction, to make it more scalable so you can, I guess, make more money by doing less work.

You’re doing public speaking, consulting, you’ve got a podcast, you’ve written a book, you’re doing retreats. Do any of these things stand out? Are there any outliers where they’re disproportionately effective or maybe they’re disproportionately time-consuming and you wish you hadn’t done them?

Sherry Walling 49m 24s

Yeah. I think I love doing retreats. The last retreat that I did I planned with some co-facilitators. And none of us were professional retreat planners or event planners, and I will never do that again. I will only have an event planner do any future events that I do, because it was just so much bandwidth and time and energy picking menus and working out room spaces. And it’s like I’m not good at that kind of level of detail and it doesn’t excite me. I don’t like it.

So it took a lot of energy to put that together. And really, it was a case where I should have just hired someone who was way more efficient and has more expertise than me to do it for me.

Courtland Allen 50m 12s

On that note, why don’t we talk a little bit about hiring? I know you’ve got people helping you with Zen Founder. How many people are helping you exactly, and how did you go about finding them and convincing them to join your team?

Sherry Walling 50m 22s

Yeah. We have kind of a cast of characters that help us, and most of them have come onboard through word of mouth, like our audio editor for the podcast, for example. I have an assistant that we just found on oDesk and I’ve been trying out and increasing her sort of authority over my life as I work with her more.

And I would say that hiring has been something that has been harder than I thought, especially because – so in my previous work, I hired junior clinicians who worked at the clinic where I was a director. And so I have a lot of experience interviewing and hiring, but the job was always pretty well-defined and didn’t require a lot from me. It was sort of like, “Here, new psychologist; here are your clients. Go and do your work.”

There was more to it than that, but they were experts who sort of knew what their job was. And here I am bringing in folks where I am practicing how to explain the details of exactly how I want the podcast to be done and what I want the tags to be and the categories to be and all of the things.

And I’m learning that, again, my attention to detail in communication is really not awesome. It’s a whole skillset that I’ve had to learn in hiring, which has been somewhat of a surprise for me.

Courtland Allen 51m 50s

I think it’s interesting that you’re doing a lot of things that can be immediately profitable. It’s not this long, slow revenue ramp-up that many people with SaaS businesses have. If you’re doing public speaking or you’re doing retreats, people pay you immediately, which means you have the funds to hire immediately if you really want help.

You’ve been hiring a lot off oDesk and things like that. What have you learned about this hiring process that other founders could learn that could help them hire more effectively and find the right people and do a good job of communicating with them?

Sherry Walling 52m 20s

Yeah. So one of the challenges that it experience, and maybe one of the cheats that I use, is the fact that I’m operating at a level of success that’s probably more commiserate with my life as a psychologist than my life as a founder. And so there’s a lot of things that I don’t know and I’m not good at that are more technical, which means I bring in a lot of help. I bring in help from my friends who were founders.

I was talking with someone about doing some SEO help for my site, and I’m like, “Honestly, I really don’t understand this very well.” But I have friends that do. I have friend that are experts in this. So they reviewed the person’s content material, and they looked it over and they said, “Oh, this doesn’t sound quite right. Ask about this or ask these questions.”

So in a way, when I’m hiring, I have a first pass with someone who I know who I’m friends with who is deeply successful in whatever content area it is, because there’s a lot about being a technical founder that I know nothing about that, that I’m not good at at all.

So I have an acute sense of my weaknesses and am really good about asking for help, which I know is not the case for everybody. But because I have kind of a deep network at this point, I’ve been grateful for people to review a lot of the potential hires that I’ve had.

And of course, my husband Rob is great at that, and so he does a lot of this with me. He’s also involved in Zen Founder alongside me, so we do some of that together.

Courtland Allen 53m 55s

A lot of people who listen to the podcast are not programmers, they’re not technical. And as a result, they have a lot of trouble building sort of a reputation and credibility, and also practical things like website for themselves.

You’re also not technical, and yet you’ve been able to build a huge presence for yourself, a big audience, and a beautiful website. What are your tips for nontechnical people operating in the web space? How can they do what you’ve done?

Sherry Walling 54m 18s

I think having good help is important, having a lot of people review your site, for example.

I think I’m amazed at how people see things that I don’t see, whether it’s in the copy or in the design or in the functionality. And I have found it hard sometimes but really important to just be humble enough to say, “Hey, what do you think of this, how does this look to you, what bothers you about this?” And it’s not always great to hear that feedback but important.

So I’m in a couple of mastermind groups with people who are more technical than me. And they’ll look at my stuff and give me two pages of feedback. And it’s painful sometimes because I feel really stupid. But they do. They see things that I don’t see.

So I think asking for help, being humble enough to take feedback, realizing that you can’t possibly see or know everything about your work is really helpful. And then, again, that practice of just getting yourself out there over and over and over and being on podcasts, asking people to be on your podcasts, guest writing on things, asking people to write for you.

One of the things that happened recently that I was really excited about was I got asked by Stripe Atlas – many of your listeners are probably familiar with Stripe. They have Atlas, which is a series of resources for people who are starting online businesses. But they asked me to write a guide to stress management. And it’s a really nice little way to get my name out there for a lot of folks who come across Stripe’s work.

But the only reason that that happened is because seven years at a conference, I met patio11 or Patrick McKenzie. And I’ve seen him a couple times and I follow up and we’re friends on Facebook. And when you show up over and over for a long time, people notice.

Also a part of that is showing up well; is making sure that as you’re building your network, you’re paying attention to who people are and being good to them, being curious, that you’re not a jerk at a dinner, that you’re not entitled in a conversation; that when you’re meeting people, you’re always on, you’re always gracious, you’re always listening well.

I know this sounds like maybe a tangent from your question, but the way to grow an audience is to be someone who’s engaging and connectable, someone who people want to connect with. And that takes a long time.

Courtland Allen 56m 57s

I think all of that is great advice for everybody, not just nontechnical founders. One thing that’s interesting that I’ve seen on Indie Hackers is somebody will come onto the show – or they’ll come on the website, they’ll do an interview, and they’ll just talk about what it is that they’re doing with their business.

And very often, I hear these same founders come back and say, “Courtland, you won’t believe what happened. We closed this deal or we made this sale or we made this hire or we got acquired or we got this great advice, because somebody reached out after reading our interview.”

And I think half of what’s going on is that if you come out and you share your story and people find it helpful, then they want to help you back, they want reciprocate.

But the other half of what’s going on is that if you tell your story and you share all these details, then people know how they can help you. They don’t have to guess. You’ve written it down, exactly what you’re trying to do. And so they’re like, “Oh, I’m good at that. Let me help Sherry with that problem that she’s having.”

So I think, in addition to helping other people, it’s a good thing to get in the habit of just talking about what you’re doing in public so others can see.

Anyway, we’re approaching the end of our time here. Sherry, is there anything from your book or from your work that we haven’t touched on that might help fledgling founders become more successful with their companies and be a little bit more psychologically healthy while they do it?

Sherry Walling 58m 7s

I think, hopefully, the folks that are listening to this have connection beyond just listening to the podcast, but being part of a forum like Indie Hackers, being somebody who goes to events every now and then, being someone who’s cultivating a couple of friendships with other founders, I think, is really, really important.

When we think about, going back to the trauma literature, maybe where we started, coming full circle, if you in your life are going to go through a terrible thing – traumatic bereavement, the loss of someone, an assault, just something terrible – the one thing that has consistently been shown to be the most important protective factor, so the thing that helps decrease the likelihood that you’ll have a bad mental-health outcome, the one thing, the one asset that you want available to you is a couple of good relationships.

And you don’t have to be the bell of the ball, you don’t have to be the person with the biggest network, but you want a couple people that care about you, that sort of know the details of what’s going on in your life, that will bring you a sandwich at the hospital or will fly across the country to attend your dad’s funeral with you if that’s what you need.

And those people are not always easy to find. But when you put yourself in communities like Indie Hackers or other places where you’re bumping up against people who have similar interests and similar goals, that’s a great place to develop those kind of deep lifelong friendships with folks who are going to see you through the ups and downs of whatever your journey ends up being as a founder.

Courtland Allen 59m 53s

I couldn’t agree more. Well, thanks so much, Sherry, for coming on the podcast. Can you tell listeners where they can go to learn more about what you’re up to personally and about Zen Founder as business?

Sherry Walling 1h 0m 3s

Absolutely. So I live on the internet at ZenFounder.com. That’s where you can find out about the podcast and the book and articles that I’m reading and whatever else. And then I also have SherryWalling.com, which houses kind of my therapy practice and information about my background and work in the psychology world.

So it’s been such a pleasure, Courtland. Thanks for having me on. And I’d be happy to be a resource for any of your listeners as they have questions or mental-health kinds of needs.

Courtland Allen 1h 0m 37s

All right. Thanks again, Sherry.

Sherry Walling 1h 0m 38s

Take care.

Courtland Allen 1h 0m 40s

If you enjoyed listening to this conversation and you want a really easy way to support the podcast, why don’t you head over to iTunes and leave us a quick rating or even a review? If you’re looking for an easy way to get there, just go to IndieHackers.com/review and that should open up iTunes on your computer. I read pretty much all the reviews that you guys leave over there, and it really helps other people to discover the show, so your support is very much appreciated.

In addition, if you are running your own internet business or if that’s something you hope to do someday, you should join me and a whole bunch of other founders on the IndieHackers.com website. It’s a great place to get feedback on pretty much any problem or question that you might have while running your business.

If you listen to the show, you know that I am a huge proponent of getting help from other founders rather than trying to build your business all by yourself. So you’ll see me on the forum for sure as well as more than a handful of some of the guests that I’ve had on the podcast.

If you’re looking for inspiration, we’ve also got a huge directory full of hundreds of products built by other Indie Hackers, every one of which includes revenue numbers and some of the behind-the-scenes strategies for how they grew their products from nothing.

As always, thanks so much for listening and I’ll see you next time.