Why Does Structure Equal Freedom In Every Entrepreneur’s Life?

Shannon Waller: Hi, Shannon Waller here, and welcome to Inside Strategic Coach with Dan Sullivan. Dan, in a recent workshop, you were talking about the challenges that entrepreneurs have with taking Free Days, which is part of our Entrepreneurial Time System. And you made a comment that I thought was spot on. You said, "You gravitate to the part of your life that has the most structure." And Free Days do not tend to have the most structure. So I'm excited to dive into that because Free Days is something that all entrepreneurs struggle with, the ones I've met, and it doesn't matter at what level of our program. In fact, at the highest level, I think they have some of the most difficulty. So let's define a Free Day, and then let's get into this idea of structure. So what is a Free Day?
 
Dan Sullivan: Well, a Free Day is a 24-hour period from midnight to midnight that has no work-related activity. So, no computers, no cell phone, no emails, no reading of materials that are related to business. And I'm pretty strict about it. Like, I don't read business books, period. So that makes it easy for me not to read business books on Free Days because I'm not interested in other people's views on business. The thing that I've noticed is that with our three different kinds of days in Coach, they have three purposes. So right off the bat, our definition of a Free Day is for rejuvenation. It comes from a Latin word which means to make young again, to make fresh again, to refresh yourself. So my sense is that taking a day as if it was a Free Day, but structuring it with activities that are business activities, means that you're not going to be rejuvenated by the day.
 
So how do I rejuvenate? Well, first of all, I'm really interested in history. I've always got history books on my Kindle. Also, I'm passionate about murder mysteries. Some of these are sort of domestic, they're like big city New York, Los Angeles. There's one fascinating series is Minneapolis. And you usually don't think of Minnesota as a hotbed of crime. But this writer, John Sandford, really does a great job. And he's got about 30, 35 that I've read. And then I'm a current affairs nut. So I like knowing what's going on in the world. And I'm a political junkie, so I'm interested in politics. I'm especially interested in geopolitics since I discovered a great thinker in that realm, Peter Zeihan. I just have a lot of structure to my days when I'm not working that is fascinating to me as my workdays, you know. I have over a thousand books on my Kindle and about 400 of them are unread, you know, because I just order them. Oftentimes, you get a note that it will come out, you know, six months ahead. And I buy the book and then I forget that I bought it. And then it pops up on the screen and everything.
 
And then, I like big city life. So my favorite place is to go- Absolute favorite place to go on Free Days is London, UK. And we have structured things to go see. It's a city filled with history, so it's a great theater city, so we go to theater. And then there's exercise. I've got very structured exercise plans and everything. So I'm just giving you an example of someone who has structured Free Days. I love parties. I love dinners. So I plan ahead. As a matter of fact, it's kind of interesting that, I think Kathy Kolbe and her great philosophy says that oftentimes doing what you're not strongest, your, what I would say, the what's the phrase, the thing that you're less insistent in. In business. And mine would be Fact Finder and Follow Thru, you know. So in the Kolbe profile, I'm a 2 2 10 4. So I have to be very economical with my Fact Finding and very economical with my Follow Thru. But when I'm on Free Days, I like planning things. I like making arrangements. I like thinking ahead and scheduling things. And I find that very rejuvenating, where I wouldn't touch any of those activities at all when I'm having an office day or a workday. The office includes Zoom now. So that's just to talk about what structure. For most people, their Free Days are not working. But they have a complete absence of structure about how they go about their Free Days. And I give as much emphasis to structuring my Free Days as I do to my workdays. Structure means that I'll be supported by things that are already planned. I'll be supported by other people's activities. And, therefore, it's much easier for me to work than to take a day off.
 
Shannon Waller: And I think that's the big trap that people fall into that I hear about. They don't have a structure. And work is fun. Work is interesting. Work, to some extent, is count-on-able. And if they don't have that structure in their personal life, none of those things are true. You know, the activity may or may not be enjoyable. It's probably not planned. It may not stimulate them to the same degree that their work does. So those are all challenges that if you talk about how structured your Free Days are, and I know because I'm with you on some of them, yeah, you're very intentional about your time.
 
So I want to address something that I hear from people. One of them is like almost a scarcity mindset. Like if they have an idea, they're like, oh my God, someone told me they stopped their kids on a bike ride to capture the idea. And last quarter, I had coached him. I said, you know what? You'll have an abundance of ideas. There's lots more where that came from. Check your next workday and see if that idea doesn't still come to mind. If it does, it's probably a good idea. If it evaporates, it probably wasn't such a good idea. That was just your brain being busy. And he said that one idea that there's more where that came from completely changed his Free Days, which I was gratified to hear. But there's this worry, this concern, this fear, this kind of scarcity that, oh, my God, if I don't capture every single idea, it's going to disappear or I'm going to lose out. Can you talk to that, Dan? Because there's a mindset there that's kind of interesting.
 
Dan Sullivan: Yeah. And that's a learned skill for me. You know, I used to have the same sense of grabbing a note sheet or I've got files in my computer. In my case, the ideas I have is a new tool I've been thinking about, or it's a new book title. Podcasts are pretty spontaneous, so I don't do a lot of structuring of podcasts, but books require quite a bit of, you know, we have to get the chapters right. And the ideas come to me, but I'm doing it all the time. So I was saying it's a lot easier to write a hundred books than if you think you're only going to write one book. That's really hard. If you think you're going to write a hundred books, none of the books are as important as the person. Any one of my books is not important to me as if I was just writing one book. Not only that, if I've been writing that one book for 10 years without a completion, that's almost being taken hostage by your own brain, you know.
 
But the big thing is, I find that I have a good ability to create new ideas when I'm focused on that activity. The other thing is that most of my ideas that enter into the Program really come from the conversations that take place in the workshops. My role in the workshop as coach is I'm there to create structure that we've already prepared for and to take that. But what I'm most interested is there are new ideas that I said, gee, that's a good one. And then I write those down during the workshop. And I'm pretty good about at the end of a workshop day of getting my notes and kind of putting them into files. And they're growing files. You know, I've got tool ideas, maybe 30 or 40 of them. So I don't feel a lack of scarcity. The other thing is that if an idea is really a great idea, it bothers you.
 
Shannon Waller: I never thought of it that way, but you're right.
 
Dan Sullivan: Yeah. It wants to be born in the world, a really great idea. And I'm the closest human that it's got. So it just bothers me until I do something with that idea. But I think your mention of scarcity about new ideas is a very, very important one. I think I've gone a little further in my thinking than most people do because my StrengthsFinder is Ideation. And so it's what I do when I'm working, so I'm not really interested. If I have an idea, usually during Free Days- For example, I have a great AI program which I promote for entrepreneurs called Perplexity. And Perplexity is just utter simplicity. You go on and it says, "Ask a question" or "What do you want to know?" You know, you just type it out and you press a button and boom. It's not a search engine, it's an answer engine. And this morning I had an idea. The question was 10 ways in which Christianity created the groundwork for capitalism. I mean, I had it in 20 seconds. I read through that. I said, this is really fascinating. Like the monasteries were much more efficient economically than any of the surrounding activity. And the monks worked out all sorts of work schedules. They're the first people to have work schedules. Every hour of the day was scheduled for some sort of activity. And you know, and then it had nine other points to it.
 
And I said, well, this doesn't relate to my work. But I'm doing serious thinking during a Free Day. I'm doing serious thinking. You know, if I'm reading a murder mystery story, Los Angeles seems to be the perfect city for almost any crime you can imagine. And I'll have a map of Los Angeles out because they use the geography of the city. And then I'll come across a part of the city I didn't know. And then I, you know, do a little bit more interest. What's the history of this section of the city and everything else? So it's really, really interesting. But if you looked at me, if you followed me around, and you followed me on a workday, and you followed Dan around on a Free Day, in many cases has more structure and more scheduled activity on a Free Day than he has on a Focus Day, but none of it relates to work.
 
Shannon Waller: What I really appreciate about what you said, Dan, is you gave a perfect example of still using your strengths and your curiosity and your 2 Fact Finder, 2 Follow Thru, 10 Quick Start, 4 Implementor Kolbe, but you're applying it in a very different way. So you're still striving in a way, but striving for fun, striving for interest, striving for fulfilling your amazing amount of curiosity that you have about the world. I don't think a lot of people have thought about it like this. And we've talked about this with regard to Free Days before. You don't go from being super intentional and focused during the week to being a couch potato on the weekend. That ain't happening. But you've just described a perfect example. And I've seen you on both days and you're completely right. You actually look the same on both days, maybe a few fewer people that you're interacting with, but you're doing the same type of activity with a very different end or with a very different topic, for example. And I think that's great coaching because a lot of people are like, oh, I can still make stuff up. Yeah, I just make it up, but it's not a work thing. I like that.
 
Dan Sullivan: What would you say about the fact that I don't read business books?
 
Shannon Waller: Well, what I've heard you say before is that what's important to you, two things, actually, one is you don't want to actually use other people's ideas, especially if it's so close to our clients. You don't want to mistakenly take something from someone else, so I respect that. The other thing is, you are so hyper-focused, Dan, on our clients, their goals, their dangers, their opportunities, their strengths, and you have this incredible capacity and capability for ideation to come up with solutions to that—simplifying the incredible complexity that is involved with entrepreneurship—that I think you have a lot of trust in your own capabilities, and you kind of don't want to clutter it up with other people's. So those have been my two conclusions. You know me, I love to find cool stuff that can be multiplied, yourself included. I read lots of different types of books, as long as they meet certain criteria, but I totally respect your approach to it. Does that sound fair? Does that hit the mark?
 
Dan Sullivan: I think everybody goes about this in their own way. I really learned how to entertain myself very early. I learned how to keep myself stimulated pretty well by myself. So that would probably be a different thing. For being someone who's not social, I interact with an incredible number of people. But Babs and I never, since- We've been together 42 years. We've never socialized for the purpose of generating business.
 
Shannon Waller: Right.
 
Dan Sullivan: Okay. So there's a lot of social activity, which is really related. For example, golf. I know how to play golf. I was a caddy, and I've had that, but it wouldn't- Let's take some people who aren't in the Program and go golfing with them, and maybe by golfing, we'll get them into the Program. Or let's take them to a fancy restaurant or anything like that. But we have a whole mechanism for bringing in new clients in the business. And the last thing I'd be thinking about outside of business was interesting people in the business because we've already handled that with our own systems.
 
Shannon Waller: Yeah, so what I'm hearing is, because of how you've structured the business, your free time is less likely to get, I was gonna say polluted, that's a bit of a strong word, but confused.
 
Dan Sullivan: Well, mixed together. It's not mixed together at all. Actually, there's strict barriers.
 
Shannon Waller: Yeah. So Dan, let's talk about that. You know, you're talking about how to have successful Free Days, and I love your example, but still let's get to the heart of why Free Days are critical for success and critical for growth. Because again, I can name by name some entrepreneurs who still struggle with Free Days or they're like, well, I do what I want during this part of the day and I love work and so I do that for the rest of the day. But what's the value of 24 hours, midnight to midnight, no work? Let's anchor people in why that is actually strategic, not just a nice to do.
 
Dan Sullivan: Yeah, well, just to put definition on the other two days that we have, Free Days are for rejuvenation and Focus Days are for profitability. For many years, we had there for productivity, but productivity doesn't say you're making any money. Profitability says you're not only making money, but you're keeping money, which seems to me to be the purpose of any business. The third one, Buffer Days, which are in-between days, which are business days, but they're for the purpose of preparing future business activities, but they're also preparation for the work that has to be put in place before you take Free Days. So I use Buffer Days to get ready for Free Days. I use Buffer Days to get ready for Focus Days. And my Focus Days are Front Stage days.
 
Shannon Waller: Yes, and when you are designing tools for Front Stage too, right? And we've talked about this before, but it's creativity and relationship. And I love it. And I add that into a lot of people's thinking on the Weekly Planning Call. It's like, yes, obviously when you're seeing your clients or whoever you're interfacing with, but also when you are creating solutions, strategies, tools, designing, solve their dangers, maximize their opportunities, that's, as far as they're concerned, what they're paying you for. So I love that, and I love that design and delivery are two of our very common Focus Day activities.
 
Dan Sullivan: I think I'm a person who likes sharp distinctions. I don't like mashup days.
 
Shannon Waller: Melted Neapolitan ice cream?
 
Dan Sullivan: Yeah. It's so funny because when I'm eating, I really like mashups.
 
Shannon Waller: Just not your time.
 
Dan Sullivan: When I'm eating on workdays, when I'm eating on Free Days, I like mixing the food together in different ways, but that's another topic. Anyway, what about yourself? I have a sense that you don't lack for interesting and structured activities in your Free Days.
 
Shannon Waller: I don't. Before I met you, I didn't have any. Bruce asked me when we were first starting dating, he goes, Shannon, do you have a life? And that's one of those questions if it takes more than three seconds to answer, the answer is no. It took me more than three seconds.
 
Dan Sullivan: And there's a lot hanging on the answer.
 
Shannon Waller: There sure is. Because I worked all the time. I had the highest billable hours in my previous organization. So then I'm like, oh, one of my biggest fears in life is being boring. So I did not want to be boring. So I immediately picked up some hobbies, took some tennis lessons, did things. But now I know the environments that really work for me. It's incredibly rejuvenating to go up to our cottage. You know, we have cottages on the same lake. I know the people I spend time with. I have more friends up where our lake homes are than I do in Toronto because that's where I have the most leisure time. You know, I know the books I like to read, I know the environment I want to be in. I love traveling, love absorbing different people and cultures and things. So I'm so much more conscious and aware of exactly what it takes for me to rejuvenate.
 
And I also know what it's like to work, kind of like going back to the why, when I'm rejuvenated versus when I'm tired. You and I are both very capable even when we're tired, but what we can do when we're actually rejuvenated is a whole other dimension of creativity and value creation. So I've learned through your coaching that wearing myself out is actually not profitable. So it's incredibly strategic to take that time off. It's not just a nice to do, it's actually, as you say, a necessary precondition for periods of high achievement. And I'm committed to high achievement. I'm not interested in just being mediocre, just being okay. So I know if I want to be my best and do what I'm best at, then I need to make sure I'm rested and rejuvenated to get there. So, for me, it's a strategy. Most people look at it as a reward, and I look at it as a strategy ahead of time.
 
Dan Sullivan: You know, another aspect of this that just occurred to me is, I have no intention of ever retiring from work. And I think that affects how you take your Free Days. Because I think a lot of people say, "At a certain point in my life, I will have all Free Days and I'll no longer be working, and work will be something in my past." So I just saw that if you think you're always going to be working right up until the actual end, then I think you structure the Free Days right now very differently.
 
Shannon Waller: I think that's a really critical point. And you've talked about Free Days. It's like when you're rejuvenated, it's like you never run out of energy. Some people retire because they're just exhausted. But that mindset is a little bit of like this, people say, yeah, I'll sleep when I'm dead. It's that same kind of thinking. It's like they just wear themselves out. But if you have a plan for the long term, then you don't want to get worn out. You want to keep yourself at a peak level of energy, both mental and physical.
 
Dan Sullivan: Every 10 years, I take the equivalent of four years off.
 
Shannon Waller: Wow.
 
Dan Sullivan: And maybe more, you know, and I would say that most people who are working hard so they can retire aren't taking very much time off while they're working. And even when they're technically taking time off, they're thinking about work. So I think that makes a big difference. Babs and I have been living together and working together easily 40 years. And I can say easily that we've, in terms of our accumulated Free Days during those 40 years, I would say we've probably taken somewhere between 16 and 18 years of Free Days.
 
Shannon Waller: That is kind of wild when you aggregate them like that.
 
Dan Sullivan: I hadn't thought about it before. So we're never exhausted by our work.
 
Shannon Waller: Yeah, that's a really powerful point. So, Free Days are necessary for short-term creativity, long-term, I don't love the word sustainability, but long-term careers, entrepreneurial careers, never getting tired, never retiring, which is really powerful. So Dan, just to wrap up, this is such a fun conversation, just to circle back to the beginning, there's books, authors you love to read, there are places you like to investigate, there's Perplexity.ai, which helps you explore non-work ideas. Any other additional coaching or tips for people who are like, okay, maybe I'll finally give this Free Day thing a try? What would you suggest?
 
Dan Sullivan: Well, I would say just don't have an unplanned Free Day. And have real intention for every Free Day that you take. Because it'll show up differently for everybody in terms of what they choose to do. I'm as intentional about my Free Days as I am about my workdays. You use a word, and it often comes up in our conversations, that I have just as much agency with my Free Days as I have with my workdays.
 
Shannon Waller: Right. And I love that word agency. So again, you're always talking about taking ownership of your experience, which is often you're talking about the past, but taking ownership of your time. Entrepreneurs get hooked kind of by the focus of the Focus Days and workdays and all the rest of it, but to apply that same intentionality... So Impact Filters, everybody, it's a really good idea. And also setting yourself up for success in terms of what could upset a Free Day. Is your team set up and prepared? What happens if ... ? And play out some scenarios so that they're confident. You know, schedule a Buffer Day. If you're taking a week's vacation, schedule a Buffer Day before and after so that you can get all the stuff done. Actually, I think almost always before a long stretch of Free Days, I end up having a Focus Day before just to like wrap up all the things. Have a Buffer Day when you get back so you don't stress yourself or your team out.
 
I mean, there's so much wisdom and knowledge about how to do them, but I think your number one thing is, don't have an unplanned Free Day. Don't leave yourself to your own devices if you're not trained yet. Do you remember, Dan, there's a model that you created years ago, whereas you're first learning to take Free Days, you take them planned and away. Then, stage two is away but unplanned, preferably in a different time zone with really inconvenient Wi-Fi or bad Wi-Fi. Then, you get to at home and planned. And eventually, when all the training wheels are off, you can have less planned and at home, still intentional.
 
Dan Sullivan: I think I'm rethinking that.
 
Shannon Waller: Are you? Okay, so keep it planned?
 
Dan Sullivan: Because I find my Free Days in my 40th year are much more structured than they were at the beginning. I want to get some pop out of every day. But I'm noticing a big difference of how not tired I am. And I'm just struck these days at age 80, I started at age 30, I'm now 80, that I'm actually less tired out by work at 80 than I was at 30. I used to really exhaust myself. One of the things I notice is sleeping on airplanes. I mean, even an overnight flight, I mean, which we've done a lot of over the last year because we've had some very long flights. But I used to remember going to Chicago or one of the other cities to coach for a week. And the moment I got on the plane, I fell asleep and I'd be asleep for the whole flight. I can't remember the last time I fell asleep. I'm usually reading a novel or... So I actually think that I'm getting great rewards from my approach to the sharp distinctions between Free Days and Focus Days.
 
Shannon Waller: I love hearing this, Dan. Thank you. As always, you kind of lead the ground. I know you and Babs, well, Babs actually was one of the first people to kind of turn you on to Free Days.
 
Dan Sullivan: I had never taken a Free Day before Babs.
 
Shannon Waller: Yeah. Thanks to Babs for Free Days. But how you're so intentional about it, the things you love to do, the types of novels, the types of thinking you do, I think I've found that almost the most fascinating. So I love that. The message is, do not leave yourself with an unplanned Free Day. Thank you, Dan. As always, fascinating and interesting.
 
Dan Sullivan: Thanks, Shannon.