205 FS Retreats with Sherry Muterspaugh Walling

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01:39 - Sherry Muterspaugh Walling Introduction


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CHUCK: Hey everybody and welcome to episode 205 of The Freelancers’ Show. This week on our panel we have Reuven Lerner.

REUVEN: Hi everyone.

CHUCK: I’m Charles Max Wood from DevChat.tv. And this week we have a special guest, Sherry Walling.


CHUCK: Do you want to give us a brief introduction Sherry?

SHERRY: Sure. I am a clinical psychologist and I work as a therapist primarily. So I take care of people who are stressed and suffering and trying to figure out how to live life well, and I also do some consulting with founders and the co-hosts of the Zen Founder Podcast. I have some expertise in the area largely because of my marriage to founder Rob Walling and the entrepreneur journey that we've been on throughout the last 20 years of our life together. And in my spare time, I raise two small kids and do a little bit of writing and speaking and going to the beach.

CHUCK: I love how you make raising two small kids sound like a part-time job. It’s just not that way around here.

SHERRY: It’s more like a third full-time job.

CHUCK: Yeah. [Chuckles]

So I’m going to jump in here and give a little bit more context to the conversation before we get going. I met Sherry in Las Vegas during MicroConf. And funny thing was I’d heard about Zen Founder and I listen to Startups For the Rest of Us which is Rob’s podcast, and I went to MicroConf last year, and so I kind of knew who Sherry was. But I was sitting at a table during lunch and we were all just discussing what we do and who we are, and it was a large table so Sherry was having conversations with people on one end and I was sitting across on the other end of the table.

And I think I said something to the effect of I’m completely overwhelmed and I don’t quite know where I’m going with my business. And somebody said “well you should do a retreat”, and I’m like “I know nothing about such a thing”, and then they pointed at her. [Chuckles]

So we chatted for a little bit. She had a lot of great insight, and then it turned out that she has a book about founder retreats which I bought about 5 minutes after talking to her. And I actually read it this morning. I've been trying to plan a retreat. I haven’t gotten around to picking up the book, but I was like “I've just got to read this”. And ironically, I went for a drive up American Fork Canyon for about an hour because I needed some space, and then I read the book and I’m like “yeah, I need more than an hour”.

Anyway, lot of context here just to say that we got the expert on this on here to tell us why we need to do these retreats and how to do them. And I’ll also point out that – as I said, the book, I read it this morning; it’s not that long, and a lot of it feels like common sense when you're reading it, but at the same time it really does give you some context for how you want to plan these retreats and then what you want to do while you're out there.

Sherry, I’m kind of hoping that you can explain to us where the idea came from though?

SHERRY: Sure. I think –


REUVEN: Can I actually just break in and say can you tell us first what a retreat is because I'm really not a hundred percent sure I know.

CHUCK: When the oncoming army is coming at you –


SHERRY: Run! Run!

CHUCK: You strategically run, yes.


SHERRY: And that’s actually not a bad way to think about it if you think about the oncoming army rather than people carrying spears and swords and things, but it’s the onslaught of the tasks and the busyness of your life. And most of us have really full lives and lots of demands especially people who are freelancing or who are running their own businesses, and I think we can live in this constant state of anxiety response. Even if we love being that way – we love the adrenaline and the busyness of this kind of life, there is certainly a time and a place to retreat, to run, to stop being in the midst of the battle or the heat of the startup or whatever it is that you're doing that’s energy and adrenaline and anxiety-filled for most of us, and take a really strategic time out.

So retreats are a way of thinking about how to step away from all of the stimulation in our modern technical world; so all of your email notifiers, all of your – all of the bells and whistles on your computer that are telling you that you need to do things or think about things or respond to things, and to stop and have some dedicated time to think and reset and decide whether the task that you are doing in your life are really the things that you want to be doing.

CHUCK: So did you and Rob or somebody else you know come up with the idea of a retreat?

SHERRY: It’s a really long tradition. One of the parts of my background is I grew up in a very religious family and have very religious people on both sides of my family. And retreats are part of many religious traditions.

In my own [inaudible], I ended up in a seminary for a couple of years and studied some monastic traditions and [inaudible] virtuality, but then came to realize that yogis go on retreats and monks go on retreats, and lots of people in different contexts who are seeking enlightenment, retreats are super old practice. I think our catching up and becoming kind of popular because so many of us are so overwhelmed with busyness, but people have been taking retreats maybe generally for spiritual reasons, but people have been stepping aside from the task of their lives for thousands of years.

CHUCK: Yeah, that makes sense; not something that I had really thought of until I heard a few people talk about taking them, and I was like “oh, that sounds really nice”. But for me, it sounds nice because it’s I got to turn everything off, not necessarily that I go out there with any specific purpose in mind to learn something or to figure stuff out. But at the same time, it’s hard to make those 10,000-foot few decisions when I’m fighting hand to hand with something that I think is critical.

SHERRY: There are lots of different ways to think about retreats, and I think so much of it depends on how you are and what's going on with you right now. I want to be clear that a retreat is not a vacation. When we go on vacation, we go do exciting fun things. We lounged by the pool maybe. We drink some margaritas. It is a time to turn off.

But I think maybe a better way of thinking about retreats is a time in, like a time when you're really focused on a certain question or perhaps just focused on a time to rest and turn off all of the stimulation because you don’t know what might be percolating underneath the surface when you give yourself time and space to not constantly respond – be responding to demands and activities.

REUVEN: So you mentioned religious traditions and everything. I’m Jewish and religiously observant; so on Saturdays, I don’t use the phone, I don’t use the computer and everything, so I have experienced with being away from work in that sense. But at the same time, I try as hard as possible not to do work during that time.

But it seems to me that the idea of this retreat is yes to step back from the day-to-day work and responding to clients or responding to those things, but yes to thinking about where you want to go with your business. This is definitely like a concentrative work time; or did I get that wrong?

SHERRY: No, you're absolutely right. It is a concentrative work time. And you might come to a retreat with a really specific question, like “should I take on a co-founder? Should I raise my rates? Should I start saying no to this kind of client and transition my business more towards this other direction?” So you might come to a retreat with a very specific question that you just really need the time to think through.

So when I go on retreats, I have this system of big rolls of butcher paper and markers, and I lay it out on the floor of the hotel or cabin or wherever I am, and just really record my thought process in response to the big question that I’m asking. One of the first retreats that I went on actually was I was really unhappy in my job. I was working as a professor. It was a job that I thought I would always want to have. I trained for a long time to do this job. And I –

REUVEN: [Inaudible] You don’t have to convince me.


SHERRY: You think you want it, right? [Chuckles] So you could see where this story goes, but I thought I should be happy, but I was really unhappy. So I started just writing all of the things in my life that I didn’t like, and so many of them came back to this particular job. And so right there and then, in this retreat, I decided I need to leave this position. I need to do something else. And it was a really important moment of clarity.

So one simple way to start with a retreat process is to simply ask what's going well in my life, what's not going well. And when you ask that – it’s like “what clients do I really enjoy working with? How can I pursue more of that kind of client?” versus “what kind of clients are totally sapping me? Or what kinds of projects that I’m working on that I just dread thinking about or working on?” And then you ask the question “how do I eliminate these experiences from my life moving forward?” But for most of us, it takes some set-aside time to really think through those questions.

CHUCK: I was going to say you asked those questions and I started trying to think about that, and I immediately got stressed out. And it’s just because I have so many other things that I’m worried about right now; just getting enough space in my head to really consider those things, it’s rough. How long does it take for you to – once you get away from everything? You turn off the phone or you turn off the notifications, you turn off your laptop, you get out and spend – in your book, you said that it takes half a day or something to get that space where you don’t have all the inputs.

SHERRY: Right. Even just to start breathing again, it could take a good 6 hours. [Chuckling]

I would recommend going on a retreat for a minimum of 2 nights, 3 days. I think it does take that long to turn off your brain and let your body calm down. And I know for me that usually the first night I’m on a retreat, I’ll sleep for 10 or 12 hours. I’m just exhausted. I don’t feel exhausted in my daily life, but once I give myself the space to sleep as long as I want to, wow, it turns out I sleep a lot longer than I thought.

And so I think it does take a lot of time to just walk around, calm down, get out of the space of responding and into a space of being more observant and self-reflective. And that’s a big transition for most of us. So giving yourself a lot of time – I've gone on retreats for one night, and it’s just not enough time for me.

CHUCK: So I have to ask; let’s say that you're going on this retreat then and you have more than one big question. So maybe you have two or three things. There's something really pressing that you're trying to figure out with your business, and then you’ve got maybe something with family or personal, be it spiritual growth or some personal challenge that you're dealing with or some area of your marriage or something with one of your kids; and so you’ve got three or four of these things you’ve got to figure out. Do you take a longer retreat, or is 2 days enough time for you to move from one area to the other and just work through one problem until you exhaust it, and work through the next one until you exhaust that one, and then come back to the other one when it bubbles to the surface again?

SHERRY: Well, I don’t know for you. [Chuckles]

I think a couple of days is at least a good start. And I think if you can’t get a little bit of traction on a couple of questions, I think of more than 4 is probably too much to tackle in that amount of time. But 2 to 3, 3 to 4, something in there, that seems reasonable. You have a chunk of time to – you have a whole afternoon to think about “how’s it going in my marriage? How am I doing with my kids? Am I the kind of parent I want to be?” And then you have an afternoon to think about your client base and whether or not you're doing the kind of work you want to do.

But sometimes, not being able to gain traction or not being able to answer your question is its own source of information. You either need more data or you need some more input or you need more time. So I guess that’s the other thing about retreats is those type A among us who are so good at setting goals and executing those goals in a timely manner might find retreats a little bit frustrating because you're psyche doesn’t always work on the time demands that you get it. 

So ask those big questions, take a lot of notes, take as much time as you need, but if you don’t feel resolved about a question, then there's really no need to try to force a resolution after your 48-hour retreat just because you said you were going to when you set out on your adventure.

REUVEN: It was interesting as you're talking, I’m really thinking. And first of all, I was thinking “well, what have I done until now? What do I do without retreats? How do I deal with these big questions in my work?” And there's a very simple answer to that, which is I spend 6 months going to my wife and saying “urgh, this is such a problem, urgh”.

And so we – I guess instead of me having concentrated time to think about it and trying to improve things, I just stretch it out and it probably affects me and other parts of my life. I know it affects my family because they're hearing about my tension and my [inaudible] all the time. But then when you said maybe even as part of [inaudible], I don’t know the last time I took time to think about if I’m doing the things that I want to in my personal life because I’m spending so much time with my work because I’m training and I’m doing this and I’m doing this and I’m doing this to just sit back and say “what could I be doing? What could I change to be a better parent?” I just can’t remember the last time I even sit around and said that, and it’s embarrassing, but true.

SHERRY: I think it’s really common. I think we just do our lives, and you're a good enough parent and a good enough worker and a good enough spouse, so there's not a burning problem. And so for many of us, there's not a need to really sit down and “do I want to stay in my marriage or not?” Unless you're desperately unhappy, you're not going to get in into a therapy office or meet with your rabbi for counsel; you just march along.

But I think that there's some mistake in not really being intentional about examining our lives because we might be able to do better, to really press in to make a couple of tweaks to how we interact with our kids that feel much better to them and much better to us. But when we don’t stop to think about it, then I think we miss some opportunities.

CHUCK: One thing that I am thinking about here as we discuss this is that some of the conclusions that I am assuming at least that I would come to or things that I've avoided even admitting to myself – for example, I joke about not being in shape, but I’m really not in shape. And you're talking about what being a better parent, and that’s something that I kind of feel guilty about off hand, and I worry a little bit about going on this retreat and having to admit to myself how far out of shape I am, or how irrational I am about certain other things, and having to come to terms with that without anything to distract me and take my mind off of those particular issues that are not easy for me to deal with emotionally. How do you get around that stuff? How do you get your hands around it so that you can appropriately deal with it?

SHERRY: I think retreats are really hard. I think introspection is really hard because like you're pointing out, most of us are pretty motivated not to really tell ourselves the truth about certain aspects of our life. And so things like shame or other emotional processes are actively working against this kind of thinking or self-reflection.

And so I think one of the things that is helpful about a retreat is that you do have time to feel crappy if you need to. You can feel bad for a little while. You can face some hard truths and you don’t have to turn around and pick kids up from school and run people around. You have the space to be bombed.

But I think it’s really important, even as you're feeling bad, to ask the opposite question: “What's going well? What do I love? I’m not in shape, but how am I spending my time instead that’s valuable? How did I get to this point of not being in shape and what control do I have over it and what trades did I make to get here? And do those trades still make sense?” Does that make sense that I’m thinking about that?

CHUCK: Yeah, it does.

SHERRY: So you can’t totally stew in the hard part of your life because the reality is that for you to even be in this place and be as busy as you are and have your life as full as it is, more things are going well than not.

CHUCK: I think you also said something really important there, and that is it’s ok to feel bad about it. Yeah, certainly you don’t want to focus on the negative, but at the same time, having that room to actually say “you know what, I’m not doing as well here as I would like” and actually give yourself permission to feel that, to process it and then to be able to say “ok, I do have some control here and my life isn't falling apart. I could go be doing these things with my kids if I were in shape, but the reality is that we went to a soccer game on Saturday and had a good time”.

And so, I’m doing ok as a dad, and if I’m going to focus on this area, my health, then I can do better as a dad, but I don’t have to – I’m done feeling bad about it and I’m now recognizing the ways that I can improve and recognizing where I have succeeded in the other areas.

SHERRY: Sometimes it’s these negative emotions that are important motivation to make those kinds of changes. And I know all of us, as a people, are pretty motivated not to have negative emotions or not to feel bad, but there's a reason that we have the capacity for those kinds of feelings, and they're important. We don’t want to let them run out of control, but they're important correctives in terms of what we should be doing or what's best in our lives.

REUVEN: The way you're talking about this retreat, I assume this is something you do on your own. So is there something to be set forth in retreat with your spouse, or is this really something that you do on your own thinking about you and your relationship with them?

SHERRY: Rob and I both take two retreats a year alone. Usually in December, January, and usually in the summer – June, July-ish – setting the goals for the year, review in the year, and then a check in about how progress is going or how our intentions and plans are playing out. And then we, as a couple, try to go away twice a year where we are intentional about asking some of these retreat-ish questions, but then we also do fun stuff together too.

I would say that especially for freelancers or founders or people who are running their own business, this is important to do by yourself. And then if you can manage to find the time and the child care and the organization or whatever to do something like this with your spouse or your partner, then that can be really helpful as well.

CHUCK: That makes sense. And it’s interesting because I've done some of these kinds of trips with my wife where we just go somewhere and do stuff. And it’s a lot of fun, but we don’t go into some of these questions, and I think sometimes we really would come away and benefit from some of these questions being answered or having the discussion over where we’re at, where we want to go, and what we want to do.

The thing that’s really interesting about those questions though is that when I try and ask my wife about those things, a lot of times she just gives me an “I don’t know and I don’t have time to think about it right now”, and I think this kind of a retreat would benefit – it would benefit us because again, we’re getting away from those kinds of distractions. We’ll call our kids every night and make sure that they know we care, but just having the space to have those kinds of conversations, I think, will really help.

SHERRY: I think it’s also really great to have an evening set aside to talk to your spouse after they go on a personal retreat. That’s one of my favorite things is Rob will go on a retreat for a couple of days, and then we set aside an evening, get a sitter or whatever, and I’m like “tell me about what you thought about. Tell me about how it went”. So I get to join in his experience as a listener and get to support him or give some feedback about the things that he decided as he was thinking through his retreat questions.

So that’s also a way, I think, for people to connect. Chuck, you talked about your wife not having the time or space to ask any of these questions. How it great would it be for her to go on a retreat and check in with herself about “how my parenting, how is my health or am I growing personally in the ways I want to, am I reading the kinds of books I want to”, and then to come back and tell you about it after she’s had the time to think about it.

CHUCK: That was actually my next question is I don’t know how my wife would actually respond to something like this if I said “hey, I would like you to go take this retreat or would you like to go take this kind of a retreat”. And so I don’t know quite how to talk her through going and doing something like this. I would like – even if she just got 2 days’ worth of space, that would be, I think, something. But to actually have her go and be able to figure out what she wants and where she want things to be headed and things like that, I think it would be very beneficial for both of us; probably more for her than for me.

But at the same time, I don’t know quite how to get her to that place where she would go and do that. I could sit down and talk to her, but is there a way to frame this so that it makes sense to her that she would approach this the same way I do as a business owner as well as a dad and all the other things that I am?

SHERRY: I think the process is parallel. She’s the CEO of the family. She’s running a show. She’s got kids to manage and things to do. And even for spouses who work and have other things going on, I think even listening to this conversation if you can tie her down and make her listen to your podcast [chuckles] or having her skim through the retreat guide that I put together, which is designed to be really short and easy and practical and like “no theory, just here’s you do and here’s why”.

But I think it’s – for most people, a lovely invitation “hey, how would it feel to you to have some silence, to have some time alone, to have a break from all of the responsibilities that you carry?”

CHUCK: Yup, she’s busy. We have 5 kids. When I sent her on a vacation last month, she went out and visited her bestfriend for a week, but again, that’s not the same thing. As much as I sent her to get some down time, she really didn’t get any. And so that’s the other thing that I keep thinking is that if she does have that down time, even that just a day to relax, then yeah, start asking some of these questions and come to that place while she gets some physical down time, I think, would be really nice. And I want her to be happy too. It’s not like I’m sending her off just so that – “ok, figure your crap out so that I can have a better life [chuckles]”. It really is –


REUVEN: [Inaudible] if you phrase it that way. [Chuckles]

CHUCK: Yeah.


SHERRY: That’s not the pitch I would make.

CHUCK: Right. What I really want is I want her to come back and tell me how we can continue to do the things that we’re doing that work, and at the same time also, do whatever it is that we need to do so that she’s getting what she wants out of life too. Because it's not an “either or”. It’s not my way or her way. There are definite things that I can do, both in and out of the business to arrange things so that she can get what she wants as well as me getting what I want. And there's no reason why we can’t arrange around those things. But a lot of times, there’s not clarity around what those are.

SHERRY: Right. So you're asking the question like “what do you need in your life, and how can we tweak things so that you get a little bit more of what you need whether that’s time or space or exercise time or whatever”. It’s about problem solving together, but until you know the problems that need to be solved, you can’t really implement any changes. And in some ways, that’s the retreat question. What needs to be different? What can be better? What's going well, what do we need more of?

CHUCK: Yeah, that makes sense.

SHERRY: And then you make a plan.

REUVEN: It feels to me if I were to do one of these retreats – and you're making it sound very attractive, I must say. Although I think if my family were to hear me say “oh by the way, in addition to all the travel that I do, I’d like to go away for 2 days”, I think some smart pitching there.

CHUCK: I don’t know though because the way that it’s been put forward by Sherry as far as you get away to figure these things out, just pitching it in the sense of “this is what I’m hoping to get out of it: more clarity, more happiness, more rest, a better vision of where things are going”, they all benefit from that.

The other thing is – and this is something that has had a profound impact on me just over the last 5 years of being out on my own, is that things have gotten hard sometimes. And I've gone to my wife and I’m just like “I’m sorry things are so hard and blah blah blah. Do you want me to go get a full-time job?” I've asked her that a couple of times. And she has always said that she’s much more interested in me being happy than me being less busy. And so if that means you can take a couple of days to get that benefit, you'll that your family is behind that.

REUVEN: Ok. Ok, so that’s pretty convincing. I guess part of my worry is, and this might be ridiculous, but I’m going to come up with all these issues, all these problems. When you say make a plan, I guess it’s like a software project to sound like a nerdy here, which is there are always way more issues. It’s like the backlog on a software project. There are way more tickets, way more bugs, way more features you want to deal with than you have time to deal with, and you have to prioritize.

And so I guess – I’m guessing that part of the goal of a retreat is that not just to identify problems and issues, but also to prioritize what you want to work on or what are the most important issues to fix in the next 6 months, a year, or until the next time you have a chance to think about them.

SHERRY: Absolutely. And I think one of the benefits of listing all the problems, so to speak, is that often there's themes that link the problems. So there's themes maybe around being too busy and missing stuff with your kids, or there's themes around really really difficult clients that are stressing you out or creating a lot of internal havoc for you. So I think if you sit down – at least this has been my experience and Rob as well and people that we've talked to about this – if you list like “these are the things that my low points for the year; the things that I just – my low points where I was sad or I was depressed, I was angry and I was at my worst”, often there's some interrelationship between those low points.

And so it might not be 86 different bugs; it might be 3 that are really causing a lot of problems maybe across domains of your life, or at least you can identify “these are the priorities. These are my real pain points. And here are some ways to problem solve around them”.

CHUCK: Yeah, it makes sense. And in the book you actually talked about this where you say – you basically say “ok”, you identify the problems, you’ve identified possible solutions, and then you make a plan, you make goals and you don’t come out of it just with these ideas of “ok, these are the things I’m going to fix”, but you’ve come out of it with ideas and specific plans for solving those issues.

And sure, you may come back and you may have that evening with your spouse or significant other where you basically have the conversation and you tell them what you’ve learned and you tell them what you decided and you share your plan with them and they help you tweak it a little bit more to get closer to where you want or closer to where you both want. There's nothing permanent about those plans, but just that fact that you're able to get enough room to have those conversations with yourself and then make a plan that you can then go forward with is a big deal.

I have another question for you Sherry and this is for some of those people, freelancers or business people who look at where they're at now and they're just like “there is no way I can even take 2 days off. I can’t afford to not work for 2 days or I can’t just tell my family and my clients and my customers that I’m out of reach for 2 days”. What do you do? It seems to me that the trade-off for clarity – it makes a lot of sense to me where I’m at, but I can see other people looking at it and going “I don’t know if I can afford the time”.

SHERRY: Well on one hand, I would make [inaudible] a problem to solve over the next 6 months or the next 9 months. So maybe you can’t go right now, but look for a gap in your projects or look for a time when it’s maybe more possible, and then talk with some friends about housesitting for them or going camping or – you don’t have to go to a fantastic [inaudible] retreat center or hotel; you can go anywhere that is affordable to you. Go to a hostel, go to a – there's lots of options.

In the short term though, and this a little bit of a tweak on the retreat conversation, but in the short term, I think it can be really beneficial for all of us really to just begin to cultivate the capacity for increased self-reflection. So again, one of my favorite self-reflection questions is “what went well, what's life giving, and then what sucked the life from me today? What were my low points today?”

So if you can’t go on a retreat and ask these big giant questions; just ask it everyday in a small way. Spend 5 minutes jotting down a couple notes about how you felt about what happened in your life today, and then maybe begin to integrate a little bit of meditation or quiet or silence, a little bit of prayer if that’s your background or your interest.

So the thing about retreats is you're reflecting, you're looking back, you're thinking with silence and quiet without distraction, and then you're making a plan for the future. So you can do all of that everyday in 15 minutes, which I’m sure you can find. And that will at least begin to develop those muscles, so to speak, those self-reflection muscles, so that when you do have time to set aside some time for those really big existential questions, you'll have all of these data about what's going well, about what is not going well, about how you're feeling, and then I think you'll be in a great place to do a retreat even if that’s a year down the road.

CHUCK: So do you ever schedule a retreat when you have a big decision to make that’s outside of your regular retreat schedule?

SHERRY: I do. I do, actually.

CHUCK: Do those go any different than just a regular retreat?

SHERRY: I think they're very focused. I don’t do this big self-reflection over the past year or 6 months. I really just sit with that question. I make lots of pros and cons list, I do a lot of walking, I think about what I’m afraid of about the various decisions that are available to me.

I think I even outline this in the book too. These different kinds of retreats, whether they're broad self-reflection or whether you really have a burning question that you need to deal with, whether it’s to change your kids’ school or leave consulting for a job, or leave a job for consulting, or whether you need to change something in your marriage if something has happened in your marriage that’s disrupted you and you need to really spend some dedicated time thinking about that. Those might be a shorter retreat or you might not have as much time, but to really again spend this dedicated time thinking through the question is really important.

CHUCK: So let’s say that I’m an entrepreneur and I decide – this isn't too far from life. I’m trying to figure out when I can take one at this point, but let’s say that I figured out “ok, I can do a retreat maybe in a month”. And I got the weekend blocked out. What are the next steps to plan this out because it doesn’t feel like it’s something that you just go “hoo, I've got a couple of days, here we go”.

SHERRY: Yeah. If you have the time to plan, then you might choose a couple of questions that are important to think about. I would also be intentional about where you go, so finding a place that is relaxing to you that’s rejuvenating that’s not too distracting. For many people, that’s the forest or the ocean, sitting by a lake somewhere where there's not a lot of stimulation or noise.

CHUCK: I’m 5 hours from Las Vegas. Terrible idea, huh?

SHERRY: Yeah. No, no, no, no. No, no, no, no. Don’t do that.

REUVEN: There's nothing distracting there luckily.

CHUCK: No, nothing.


SHERRY: So yes. So we’re quiet.

And then I would dedicate a notebook or a roller paper or something that becomes your retreat tool that you go back to over the course of your retreats over time. Gather some materials. I would recommend you not take your computer if you can at all get along without it. And then if you have the time to prepare in advance, then yes, pick a couple of questions that you want to sort through.

If you don’t have the time, then that’s ok. You can begin with some more general questions and see where you're thoughts take you.

CHUCK: That makes sense. Now, you mentioned you take a big section of butcher paper. Do you do that? Do you take a notebook? Do you take a journal; just whatever works for you?

SHERRY: Yeah. I think there's lots of different ways to do it. Rob has it in a retreat notebook that he has kept for years and he – every retreat he just does a new entry. It’s full of the brainstorming and lists and thoughts and things like that. And I have these random scrolls of butcher paper because I like to get down on the floor and be nonlinear and write different sections, and I’ll sometimes make a list of things related to my kids or things related to marriage, things related to my work, and I need the space to spread out and be nonlinear.

And then I will take a picture of it or when I get back I’ll summarize it in a Google Docs so I have a record of it, but yes, I have all these scrolls of butcher paper sitting around that have been written all over with colored markers and they look like somebody draw mushrooms and had too bit of a time. But they are really actually very helpful and insightful to me.

CHUCK: One thing that occurred to me was that I might want to take something to record into my phone, but the problem I have with that is that it’s much harder to get to the part that you want if you want to go back and look at over again.

SHERRY: One of the things that I really like about writing is that it slows down your brain. Most of us write a lot slower than we think and most of us type faster than we write. So actually handwriting something tends to be a way to slow down our process and help us to be a little bit more emotionally integrated into what we’re writing. Believe it or not, people study this.

And in terms of an audio recording, I haven’t done it that way, but it’d be interesting to hear how it goes if you do decide to do it that way. Or maybe you do some writing first and then you do some recording if you're more of a verbal processor.

CHUCK: I’m much more of a verbal processor.

SHERRY: Yeah. I could tell that about you.


REUVEN: It’s funny you said this about the writing because my handwriting has been just atrocious from a young age, and so I learned to touch type at the age of 13 or 14, and it’s so much faster and easier for me to type. But I think if I were sitting somewhere and really just trying to actively think – I was thinking first of all, there's no way on [inaudible] that I would bring a notebook or a piece of butcher paper because [chuckles] it would be unreadable to me, to others.

But I think it is true that if I were to sit and take the time and write it out and not feel the pressure from the outside world, then maybe I could write things and I would definitely feel that connection that you mentioned.

CHUCK: The other thing for me is that when I’m in front of my computer, I’m in a different mode. If I have a piece of paper in front of me, I am totally in a different headspace. And so since the computer headspace is very well-defined for me because I spend all day on the computer, I think that a piece of paper, it would be easy enough for me to switch into the mode where I can let go of a lot of the stuff that I deal with when I’m on the computer and just make it happen on paper, in a notebook, in a journal or whatever.

SHERRY: And that’s a really important piece is you're disrupting whatever patterns you normally are in. So if you spend most of your time in front of the computer as most of us do, then don’t do that. Do it a different way so that you are using some different brain circuitry and you're engaging your inner life and expressing it in a way that is abnormal for you or atypical.

REUVEN: How long have you been doing these retreats for yourself?

SHERRY: About 5 years.

CHUCK: Now, when you go, do you usually go somewhere close to home? I’m thinking – I live right near the mountains. I look out my window and I see mountains because I live in Utah. And so I’m thinking “oh well, the beach would be heavenly, but I’d actually have to travel to get to the beach”. And then part of me thinks “well, it’d be nice because the weather is getting really nice these days to just go up in the mountains and just hike”, and so I’m thinking like Park City or some campground up one of the canyons or something like that.

And I think in a sense, something close by would be nice just from the standpoint of I don’t have any of the stress of travel going and coming. And the other thing is that it’s a whole lot less of financial thing to be able to go. What are your thoughts there?

SHERRY: I like to go somewhere within just a couple hours’ drive of my house because I think the retreats begins when I get in the car. I intentionally don’t listen to podcasts or sometimes I’ll turn music off altogether and drive in silence, which is again atypical and unusual for me. But to even begin to slow down and stop all the noise and stimulation on the drive, I think, is helpful.

And I agree with you about when time is so precious, I think spending the time to make a big trip for a retreat is probably not recommended unless you have extra time and you can still have your set-aside time to just relax. I think it would also be hard for me to get on a plane right after a retreat and just deal with the airport and deal with all that stuff. I think it kicks you out of retreat mode too abruptly; it’s a violent violent torture.

CHUCK: Right. The other thing that I had considered in the past was taking the retreat when I’m already away. So for example, I very seriously considered doing the retreat immediately after coming back from MicroConf because I was already gone, so I would just stay gone for an extra couple of days. But ultimately that didn’t work out for me. Is that a good idea or do you think maybe the ideas from the conference or whatever other follow up you need to do from the conference may overwhelm the retreat?

SHERRY: I think that’s possible. I think you have to do what works well for you. If it’s easier for you to stay gone if you're already gone and not re-immerse in life, then do that. If you're coming away from MicroConf or another conference and you feel distracted or hyper-focused on that material and maybe not – your thoughts aren’t necessarily representative of your normal day-to-day life, then that could be a little bit problematic. But I think practically, people – it’s more important that people just do what works for them rather than get to technical about when or how.

CHUCK: That makes sense.

SHERRY: So can I ask you a question Chuck?

CHUCK: Oh dear. Yes.


SHERRY: I remember our conversation at lunch at MicroConf and you feeling overwhelmed and busy and not sure which way you were going or coming, but what made you interested in the idea of retreats?

CHUCK: Ultimately there are a few large decisions that I've been making in the business lately, and those occupy a good chunk of my mental space. And then there are all the day-to-day things that I have to manage that I have let go for a while, and then I've come back around rather abruptly to having to deal with them just because I had neglected them. And so it was “ok, well I’m totally overwhelmed making these larger decisions and then still having to deal with the day-to-day day-in day-out things.

And the other thing is that I go through this emotional – I don’t know exactly how to describe it, but periodically, I feel like I’m doing really really well, and then within probably about 3 to 4 weeks, I feel like I’m doing really really poorly. And that feeling a lot of times has no bearing whatsoever or no relation whatsoever to the actual reality of things; it’s just the way that it is.

So I’m up for a few weeks and then I’m down for a few weeks; not depressed and not – I don’t know what the opposite is. I’m not manic and I’m not depressed; I’m just – but I’m feeling really good about things for a while and then it’s “oh, I’m doing so badly”, and then I look at things, I realize “no, it’s not as bad as emotionally you're feeling”. And I feel like a lot of it just comes from gaining some feeling of control and then eventually something will come up that will demonstrate that I don’t have the level of control that I felt like I had.

And so just being there, I hit that point about 2 or 3 days before I left for – or I hit my down point a couple of days before I left to go to [inaudible], which was the conference I was at right before I went to MicroConf. I flew from San Francisco to Las Vegas from one conference to the other, and so I was dealing with a lot of that. Of course, MicroConf pumps me up and so I came home on a pretty high note. But yeah, it’s that way for me and I feel like if I felt like I had a better grasp on things, then in a lot of ways I would feel better about things and I wouldn’t have these slumps in the middle of things.

The other thing is it hit right when I was feeling overwhelmed with things because I was realizing just how much stuff I had to do to get caught up after being gone for a week and a half.

SHERRY: Yeah. It'd be interesting to really spend some time thinking about those low points and why – if you can track what causes the slump or what is bothering you during the slump and do some reflection on that in that retreat type setting.

CHUCK: Yeah. I think there's a lot to unpack there. I think I understand some of the reasons behind it, but I don’t think I completely understand all of them, so anyway – but I have noticed that there's this cyclical pattern to it that happens; probably every 2 to 3 months, I go up and then I go down, and then I go up and then I go down – and yeah, just getting to a place to understand that.

SHERRY: Yeah. But you have to track that data too if you're somebody who does that.

CHUCK: I would like to do more of that, but a lot of times I don’t feel like I have the time or it’s just another thing for me to worry about that add stress, so it’s a weird thing. I’m definitely a data-driven data-interested person, but at the same time it’s like “huh, one more thing for me to keep track of and this is kind of hard”.


SHERRY: Right. It’s hard to keep data about ourselves especially when we don’t want to see the data [chuckles].

CHUCK: I know, right? But yeah, I think it might be interesting to track that. And in reality, I could probably track it a few times a day and it wouldn’t impact anything, and I could just set reminders so it’s like “look, you don’t even have to think about it. When it pops up on your phone or your calendar, then you just log it and move on”.

SHERRY: And of course, there's an app for that.

CHUCK: Of course there is. There are probably ten of them.

SHERRY: Yup, exactly [chuckles]. Mood Tracker is one. And there's things like that where you just get a random pop up and be like “rate how you're feeling” and according to a series of emoji faces or a number or whatever, and go back to your day.

CHUCK: If you get on on your retreat and you start to realize the business would be better off if I did these things and not those things, and you also come to the conclusion that you hate doing these things and you love doing those things, what do you do?

SHERRY: Well, you write it down.

CHUCK: [Laughter] Good plan.

SHERRY: You write it down. Those are big decisions and they require lots of thought obviously, but I think knowing that that’s your preference is a really important starting point even if you're not going to go home and change your business that next week. But knowing that maybe that’s where you want to go, that you're driving a big ship – your life is a big ship, but it can’t turn that fast.

So if you have these insights about what you want to change or what would be different and what would be better and where your sweet spots are, give yourself time to test your theory, and then take some steps in that direction and see how it feels. Rash decision making obviously is never recommended.

CHUCK: I’m really good at it though.


SHERRY: Well, you have a unique skill. [Chuckles]

CHUCK: That’s what I've been told.

SHERRY: Most people crash and burn a little bit that way.

CHUCK: Oh, I do that too, but it seems to be working so far.

SHERRY: [Chuckles] I think you should write your own retreat guide. “How to make really quick decisions based on your emotions”.

CHUCK: You know, it’s –


REUVEN: [Inaudible]

CHUCK: No. It’s – yeah. Ultimately it’s funny because some things – for example, I’m moving the websites back over to WordPress. I made that decision within 2 days and that was during MicroConf, and I’m basically done with it now. And I tend to make decisions that way.

Some of the decisions I agonize over – one of the other things that I would just point out that – and we had this conversation on The Freelancers’ Show so I feel like I could share some of the details, but having a retreat would’ve been nice for the particular decision on how I manage things with Mandy who’s the assistant that does the work on editing and posting the podcast. She does a lot of other things for me too, but we had that conversation on how are we going to structure things.

So initially, I was like “yeah, well we’re just going to do what the guys on the Freelancers’ Show said”. And then about a week later, I went back to it and I said “we’re not going to do what the guys on the Freelancers’ Show said [chuckles]. We’re going to do these other things instead”.

And then I thought about it some more and I really considered it and I realized that – no, actually, the part of what the guys on the Freelancers’ Show said that freaked me out was that I was going to try and turn everything to her at once, where in reality I wanted to make sure that we were moving along well in certain areas and then we would add in the other areas so we could work through things a bit at a time and make sure that we really deeply understood the processes behind things and really deeply understood the outcomes that I needed from her and that she needed from me. And that was really empowering to come around to that.

But if I had gone on a retreat and really thought about it, I probably wouldn’t have put her through so much emotional angst while I figured out what I really wanted. So I see the value here and I’m excited about that, but I tend to make decisions rather quickly. And then I don’t usually change my mind, but when I do, especially when it involves other people, it’s painful because they're getting this message one way and then the other way and then the other way and then we finally settle in on it. So, yeah.

SHERRY: I think again, part of this deeper self-reflection process is thinking about “what are my strengths as a person and what are my weaknesses, like where do I irritate other people, where do I fall short of my commitments, or where do I make life difficult for others or for myself”. And that’s also, I think, really fair game for a retreat kind of work is to do a little personal assessment. “What do I value right now and am I really living out of those values? Where have I been a jerk to people and how can I make sure that I” – not that you’ve been a jerk to Mandy; that’s my words, not yours – but how do you figure out how to be the kind of person that you want to be and have some awareness about that.

CHUCK: Yeah. Yeah, exactly. It’s not easy to make these decisions. But at the same time, just recognizing – I don’t think any of us want to really face down what we’re bad at. I don’t think any of us want to face down where we’re essentially failing at whatever it is that we’re doing, or at least not doing it to the extent that we would like to, or doing it as well as we want to. I have a real problem a lot of times with just admitting “I’m not good at this” or admitting that I probably shouldn’t be doing something that I really enjoy, and then figuring out “ok well, is that a decision I really want to make?” and – yeah.

REUVEN: [Inaudible] One of the things that I like about this retreat idea is that it turns into a regular part of your life. It’s not that “oh, I’m so bad”; it’s that “ok, this is a time once a year, twice a year, when I think about the things where I want to improve”. And so it becomes not a matter of “oh I’m so bad. Let me beat myself up”, but “everyone has places where they can improve. What am I going to focus on improving over the next 6 or 12 months?” And I feel like that could then be more of an upper than a downer.

CHUCK: Yeah, exactly. The other thing is that a lot of my ups and downs, I really feel like I’m out of control; and it’s not control over the fact that it’s like I have ultimate say about everything, but it’s I don’t even know where I’m going sometimes. And then just having that and saying “ok, I’m going this way which means I’m going to say yes to this and no to that and really understanding the decisions that I’m making and knowing that I need to be steering the ship this way, it puts me back at the helms so that I can actually make those decisions instead of feeling like I’m doing a lot of it off the seat of my pants and just making up wherever it is that I think at the moment I want to be heading.

SHERRY: I think you'll get some clarity about what you're in control of and what you're not. We can control a lot of how we react to things and a lot of decisions, but there's also a lot that we can’t control.

And I think that’s what's so hard about being a freelancer being out on your own, being a founder, that you are your tool, your intelligence, your creativity, your business savvy. And I think fitting right in with that is your mental well-being, your capacity to handle stress, your capacity to make decisions, your capacity to cope well with the fact that there are very real limits to what you can control in the business that you're in.

And I think, again, the retreat is part – it’s a piece of – it’s a tool to help people be as healthy and self-aware as they can so that they have the maximum ability to be productive and well and use their – yourself, your personal tool, to the best outcome that you can in your business and in your life.

CHUCK: The other thing that I see is that when I was a full-time employee, the only outcome I really cared about was making my boss happy and not getting fired. There were other outcomes, but they were all basically related to that. And as a freelancer or an entrepreneur, there are so many other things that come into play. The podcast – there are definite financial outcomes that are related to that for me that are important to me, but the thing that’s really important to me is am I helping people, am I serving the audience well, and things like that.

And so I've got that to worry about, and then I've got outcomes with other aspects of the business with the remote conferences and with all the other things that I’m doing. And there are a lot of success scenarios where I come out of it with something that I wanted. And so I feel like, again, as a freelancer or an entrepreneur, I have a lot more – if I lean on the steering wheel, it’s going to turn. In a lot of the companies I worked on, if I leaned on the steering wheel, somebody would push me off of it.

So there's a lot of that going on, and then there's also just “ok, what about marketing? What about all the other hats that I wear in my business, and how do I approach those until it feels a little bit more overwhelming as a freelancer?” And I think that’s where this really comes in because I now have the time to go in and say “ok, what are the important things? What are really going to get me the outcomes that I want? What are going to take me along to the place that I want to go to?”

And it helps sometimes to have that master plan that’s way out there 5 years in the future. But ultimately if you're going to do another retreat in 6 months, it has to be good enough to get you there. And so you could take a lot of the pressure off, you cannot worry about a lot of those things, and then you could take whatever time you need to get whatever big picture you need and then work it out so that you have a plan, be that a large long-term strategy as well as some short-term plans that you can exercise and move ahead with until the next time you do it.

And the other thing that I have gotten out of this just through this conversation and thinking through this is that in 6 months, if I get in there and my long-term strategy or plan turns out and I’m like “well, my values have changed and I want to go somewhere a little bit different”, I can change it. And the last 6 months weren’t a mistake; they were just going along with the best information I had, and now I have this time to go in and do some introspection and figure it out.

It’s like Agile development where you have the retrospective: “yeah, that wasn’t working” or “we now have more information and realize that we have to worry about these outcomes too”. And so you have better information to make better decisions that are going to get you along to where you want to go.

SHERRY: You just summarized it beautifully. Absolutely yes. And this self-reflection is the information.

CHUCK: Yup. And man, I just – I have worried so long over the last 5 and half years that I've been self-employed about making the wrong decision long term and ultimately, I just have to make the best decision I can with the information I have. And if it turns out to be the wrong decision, then I’m finding that less and less stuff is permanent. And so I can go and I can change the direction of things later on.

REUVEN: I found that by bad decisions make for great stories.

CHUCK: Yeah, there you go. I just made another podcast [inaudible] decision.


CHUCK: And I fest up to some of those on the show, but it’s really true. By the way, moral of one of the stories: pay your taxes.

Anyway, let’s go ahead and get to some picks. [Laughter] Reuven, do you have some picks for us?

REUVEN: Yes. I was actually trying to figure out what to do in terms of the pick, and from Sherry’s description of retreats reminded me – I've mentioned even in just recently this terrific new podcast called Surprisingly Awesome where they take things that seem boring and they find how they're actually really interesting.

And their most recent episode as we’re recording, the topic was Boredom. And I remember [inaudible] this and thinking “oh my god, this sounds terrible”. But they actually looked into boredom and they took the host of the podcast who are extremely busy probably like all of us listening to the show, and they forced them to be bored for a while. And then they asked them “what did you think?” and I am shocked to discover that they said “wow, this was great. I didn’t have my phone. I didn’t have my computer. I could just sit and think”; and this was for 15 minutes. And it was amazing for me to think that it would actually be positive because I think I would be gnawing off my arm or something like that.

So the combination of what we talked about and what they said on the podcast has really made me think about retreats and so forth. And in any event, it’s a fast and fascinating episode to hear about some of the scientific discoveries they’ve done about why people are bored, what makes them bored, and how boredom is not necessarily a bad thing. Anyway, so that’s my pick for this week.

CHUCK: I was just thinking what would be more painful for a teenager – taking away or their phone or the rack?

REUVEN: I think they have done studies on that and found that people go totally nuts if they don’t have their phones and start looking for things to do. And that’s really what I expect to this episode, and I think that the younger you are, the less likely you are to be able to deal with this; or if you're a programmer.


SHERRY: Which is like really deserving too; deserving in like the way that our brains are so dependent on external stimulation at this point that we can’t be internally entertained.

CHUCK: Yeah.

SHERRY: Our imagination or curiosity.

REUVEN: Right.

CHUCK: Yup. Alright, I’m going to put a couple of picks out there. For me, I’m just going to pick a couple of things that I have done or places that I've gone that I think would make great places for retreats.

The first one is, and I've already mentioned it, Park City, Utah. If you're thinking “oh, Park City like up in the mountains”, yes, that’s up in the mountains. The thing that if you’ve never been to Park City before that you need to realize is they have the main downtown area, which is essentially one road with back alleys along the backs of the buildings so that businesses can have stuff dropped up to them without blocking off the main road, but Park City covers actually a really wide area up there and a lot of it is secluded.

And so if you want to go up there and you want to stay on one of the hotels, you can, and even that’s pretty close to nature; or you can probably Airbnb somebody’s cabin out there and find some space. Not too far from that is Sundance which is at Provo Canyon. It’s halfway between Provo and Park City. Park City is on the other end of Provo Canyon. It’s up another canyon. It is kind of at a crossroads there. But yeah, those are two great places to go if you are out in my direction.

One other place that I've really enjoyed as far as ability to get some downtime or that my family has enjoyed going to, it’s Ventura, California that got a great beach and is not very hard to get aways out of town. Now granted we went out there because my mom grew up at Thousand Oaks which is not in that area, but you can get a beach house or again, something that’s kind of off the beat and track a little bit, but is within 10 or 15 minutes of a couple of different towns where you can go get food and things like that; and fairly relaxing just to be able to get away on the beach. One other thing I’ll point out is that the couple of times that we've gone out there since I've been an adult, we found that if you go around noon or a little afternoon on a weekday, there aren’t that many people on the beach so you can get a little bit of that seclusion.

The other thing is that on one of the other beaches – I don’t remember what it’s called, but it’s like 10 or 15 minutes north of Ventura, it’s got a public park area and then it goes down to the beach. And if you walked down along the beach aways, you actually get down to part of the beach where it’s beach but there are rocks right behind you and stuff, and there aren’t as many people there because the beach is rather shallow. So if you go down there during low tide, you get beach but you don’t have as many people around either. So anyway, those are all just nice places to go and walk.

And then obviously, I have to pick other places in Utah because I just love them. If you want to go down Moab and Arches, it’s another great area; or you can go to Zion National Park and they’ve got some terrific places to hike or climb or both if that is the way that you need to get away. So anyway, those are some of my favorite places, so I just thought I’d share and pick them.

Sherry, what are your picks?

SHERRY: To add to your location options, there's a website called retreatfinder.com where you can search for retreat spaces that are near where you are. And some of them are in monasteries or other small spaces that you might not know are right around the corner from where you live. And so it’s a good option, at least, to check out places that might facilitate personal retreats, silence – they're set up for that kind of thing.

I have another pick which is Headspace, the Headspace app. This is for folks who are interested in having a little mini retreat in their mind in 5 minutes or less. It’s an app that facilitates simple meditation and relaxation practices and can get you in the retreat mode even if you are not able to be away.

And then finally, it’s probably unseemly, but I think I should plug my own book which is The Zen Founder Guide to Retreats which is available on Gumroad and we have a link to it on the zenfounder.com site.

CHUCK: I was actually going to ask you to plug your book after the picks, so thanks for doing that though.

SHERRY: There you go. That’s my pick. [Chuckles]

CHUCK: But I have to say it was a quick read and it was very very direct as far as “do these kinds of things. Make sure you're doing these kinds of things. Go to these kinds of places”. A lot of great stuff in there; there are a couple of diagrams at the end of the book. And so if you're looking for a good place to go and just get an idea of how to set all this up, we covered a good portion of it in this chat, but not everything, so I highly recommend that you check it out if you're looking at doing something like this because it will really just walk you through “ok, these are the kinds of things that you need to be thinking about for you to get your retreat done”.

Anyway, thank you for coming Sherry.

SHERRY: My pleasure. Thank you so much for having me and for talking about this topic. I think it’s important and I appreciate you valuing it enough to give it some space on your podcast.

CHUCK: Well, we do this to help people and I really think that it will benefit a lot of people to at least think about going on a retreat or finding ways to take time to do this kind of introspection. So thank you for coming and sharing your expertise.

SHERRY: My pleasure.

CHUCK: Alright. Well, we’ll go ahead and wrap this up. We’ll catch you all next week.

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