109: Winning the Week with Demir Bentley
8 Dec 2025 · 49 min
Demir Bentley talks about his book Winning the Week, which argues that planning your week is essential but anxiety-inducing. He recommends pre-planning on Friday or Saturday instead of Monday, building in flex time for unexpected work, and stacking deep work early in the week. His team of five full-time staff and thirteen contractors uses weekly pre-planning to cut down on avoidable interruptions.
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Planning, even when done perfectly right, is anxiety and fear provoking. Even when done perfectly, planning will provoke anxiety and fear. Because what you're basically doing, Jenny, is taking a week's worth of what could go wrong and shoving it into 30 minutes of planning. Of course you're not going to look forward to that. Of course your animal brain is going to start to build a resistance to that and say, gosh, I don't feel good when I think about planning, so guess what? I shouldn't plan. And that's when we get these planning sessions, the shoulds of like, oh, I've got it on my calendar, I know I should do it. And then 94% of us are avoiding our planning when it actually comes around.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host, Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Hello. Hello my friends. We are in for a treat. Today I have Demir Bentley here with us who helps successful people who secretly struggle with their productivity. He is amazing. We met through a mutual friend, Selena Su. He and his wife Carrie Demir founded the Life Hack method and their podcast Freedom to Code It. Today we're talking about their brand new book, the Winning the Week how to Plan a Successful Week Every week. We were talking so much before we hit record that we just said we better hit record right now and get the rest of this good stuff in the actual podcast. So with that, Demir, welcome to the show.
Oh, thank you so much.
I was listening to you on another podcast this morning while playing balloons with my doggie and you were talking about how to be happier than a billionaire. What does that mean?
Boy, you know, I really think that we put billionaires up on this high, high pedestal. And certainly there was a past life when I worked in finance when it really maybe I'll backtrack that and say, I grew up poor. And with a lot of poor people, rich people will say, you know, money's not gonna solve all your problems. And my answer would be, hmm, I don't know. Give me the money and I'll tell you if it solved my problems or not. I really was that person who felt like, man, hard work and a lot of money will solve everything in life. And what's interesting is I've gotten to a place where I've been privileged enough to get within one degree separation of five different billionaires. Meaning I'm not their personal friend, but I'm a good friend of one of their good friends. And they are not blissfully happy. In fact, they have problems that are really crazy problems to have the kind of problems that I look over their fence and think, oh, God, I would never want that. So what I've realized in my pursuit of freedom, which really the only reason I coach productivity, is to show people how to break free and create some freedom in their life. And I've just realized that most people can be happy. What they want is so close to what they actually have that it really is just a little bit of a reach. And so when I say happier than a billionaire, what I really mean is just that ability for you to create freedoms in your life. Time freedom, monetary freedom that gets you to a place where frankly, you have a happiness that frankly rivals that of a billionaire or is even exceeds it.
Yeah, I love that you bring this up because there are so many examples of this. I quote in Free Time. The founder of Vanguard, John Bogle, cites a story in his book about the idea of having enough. And there's that. I don't know if you're familiar with the Tim Ferriss podcast. He interviewed Graham Duncan, and Graham Duncan talked about being a time billionaire, or Tyler Cowen talks about being a cultural billionaire. That we lionize people with a lot of money thinking money will solve our problems. And just like you, I find it so fascinating to hear from people who say, I'm friends with billionaires and their problems. Billionify. And what's so interesting about what you do is that you are working with successful people. And I told you before you record, this is an audience of business owners. This isn't people tiptoeing around their freedom. They're in it and they're trying to achieve that. But the irony of our lives is that the more we achieve and the more we create. You mentioned in the show earlier, like, getting married, having kids, having pets, having Responsibilities that we can become stuck by all the logistics of our life. And I just thought that's so profound for you to recognize that, because that seems like one of these complications of getting older. Like, you and I have both been in the online world for a while. Digital nomading, all the freedoms of solo life that change as our life circumstances evolve.
Yeah. I talk to my clients a lot about what I call the sweet spot, meaning life, for most people who don't have money to solve their problems can be a bit of a conqueror's curse. What I mean by the conqueror's curse is we go through life and we get married and we have kids and we have jobs, and as we conquer more territory, I mean, these are good things. It's good to have a relationship. It's good to have kids. It's good to have a business. And yet, the more territory you conquer, the more you have to defend. And so a lot of my clients can find themselves in a place where they got this really full big life. But, you know, a big life can weigh a lot, and if you're not organized in how you approach that, it can really crush you. And yet, if you can get just onto the other side of that, where your life is big enough that you're taking on the things that you want and getting all of the juicy prizes that you get from having pets and kids and properties and some money in your pocket, but not go so far as as to have billionaire problems. That's what I call the sweet spot. This beautiful place where you've conquered enough territory to have true rewards in your life and true enjoyment, but not so much that you have, frankly, the hassle.
There's another paradox of success and evolution, which is that, as you say in the book, oh, such a hard truth. You tell us to get comfortable with the idea that something can be completely worthy of your time, but you still might never get around to it. And you say, that's why I was overworked. I was chasing the long tail of my tasks into infinity. This is when the music stops and there aren't enough chairs for everyone. Oh, I feel it. I feel it. That moment where the music stops and you go, there is more good and good options and good people on my plate or in my orbit than there are chairs. And I'm just so curious, like, how that's coming up for you even now. The book is off to print. It's not out quite yet at the time of this recording. But how do you deal with this tricky truth?
You know what's funny is it's gotten easier over time because there was a part of our business when nobody wanted to play in the sandbox with us. Right when we were very new, we were really just throwing our arms around and trying to get any attention and work with anybody who would work for us. And now we're on the other side of the. Not that we're the biggest, most popular, amazing people in the world, but simply that now we are on the other side where we have more opportunities than we could possibly chase down and capitalize on more things that we could and want to do than we could possibly do. And what's interesting about that is in the very first years when that was happening, it was incredibly painful to deal with because it was hard to say no to people. It was hard to say no because to both sides, I didn't want to say no. I wanted to capitalize on every opportunity that came to me because I remember what it felt like to not have people who wanted to play with me in the sandbox. But then also it was hard to say no because you don't want to curtail more opportunities coming to you in the future. And what sort of happened is we've gotten a bit of a reputation for being the kind of people that give really upfront no's. My wife, Carrie and I have really great criteria by which we make decisions. So when you come to me, Jenny, and say, hey, Demir, I've got this idea you and I could work together in this way, I like to give you a solid yes or a solid no accompanied with a timeline, meaning my response would sound something like, jenny, this sounds amazing. Our dance card is full for this year. We could consider this next year, or I could pass you on to two or three people that I think could be a good partner in this way for you. And that's the kind of life I like to live. My wife and I have a motto. Pull triggers, don't agonize over things. Pull the trigger and live with the consequences. And I think whether that's gotten us here, you know, years on is a feeling like people sort of already know what we're going to say, you know, when they come to us, you know, we get a lot of emails that say, hey, I know you're already writing your book this year, but I don't know, just throwing this out there. Would you speak at our conference? And they've already answered their question. No, we're focused on writing and releasing the book. We're so open with what our priorities are that People actually self filter and only come to us with priorities that line up to what we've already sort of advertised.
I had a friend tell me once when I was overwhelmed, and she said, you know, maybe you just need to say no more often and know for sure that there are gonna be good opportunities or good people that slip through the cracks, but that that's okay and kind of trust that the right people circle back are the right opportunities. And that was so good for me to hear. Like, sometimes, yeah, you might miss a good one. Every now and then it just gets filtered out because the filtration system is so well calibrated. But in your case, you know, that's what's letting you write this book.
Yeah, I mean, I grew up in Hawaii and I spent a lot of time in the ocean. And if you asked a surfer how much time they spend thinking about, like, the waves that got away, they would say, like, none. You know, I don't spend any time. That would be the worst kind of surfing ever. To sit there and think, oh, damn it, there should have been my wave, but it was so perfectly formed. No, they hold it with a loose grip, right? And there's a sense of, well, the ocean is bringing me what it's bringing me, and my choices are my choices, and I can live with that. And most waves, you know, waves are breaking 247 all around the world, and I just cannot lose a wink of sleep thinking about the waves that I am not able to catch or that I passed on.
You mentioned your wife, Carrie. I'm curious if you could take us behind the scenes a little bit. Two part question. What is it like working with your wife? And I talk in free time about delightfully tiny teams, and I saw you acknowledge yours at the end of your book. So I'm curious how the two of you divide and conquer. And then what's your team set up like? And does anybody work full time?
Yeah, I mean, I'll take the easier part of that question. We have five full time people and 13 contractors, so, yes, I love that.
Term, delightfully tiny, yours is now delightfully sophisticatedly tiny.
That's incredible.
Yeah, I mean, we absolutely love it. You know, then the harder part of that question, which, although we could talk for hours about this, but I'll keep it very short. You know, when we started the business, we grounded ourselves with a couple core mottos or underlying concepts. And the first was that we were creating what I called Demir and Carry, Inc. Meaning the business was not more important than our lifestyle. Our lifestyle was why we were forming the business.
And when did you form the business? How long ago?
Gosh, almost 10 years ago. Okay, it was almost 10 years. Like, probably more like nine. Now, the reason I make that distinction is when you make the business the most important thing, then when it comes to choosing between the happiness of your partner and your business, of course you're going to choose the business. Because the idea is, I've got to be as good as I can, and I am completely willing to let the business suffer so that Carrie can be a little bit happier. And that's why Demir and Carry, Inc. Is the holding company of the business. Because at the end of the day, the business only exists to help us express ourselves at the highest possible level, do the best work that we can do, but also be the happiest people that we can possibly be. And so whenever people say, how do you and Carrie do it? I always say, you know, we never put the business above each other. Now, let me give you a very tactical example of how that really comes into conflict. Most partners, if you really think about it, you have this rightness inside of you when you see your partner making a mistake, or at least when you believe that your partner's making a mistake. And part of the reason that you go so hard to the mat against your partner is because there's a part of you that's saying, but can't you see that I'm saving you right now? Can't you see that I'm helping you not make a terrific, colossal error? And that's sort of why you get up into these places where you're up in each other's face and fighting like cats and dogs. And what I was able to do by putting Carrie first is to say, well, making errors is a part of Carrie's journey in this business. So what if she's going to make an error here? If she wants to do it and it's on her side of the business, then she should be free to do it, and we can handle it as a business. Now, side note here, Jenny. Out of the maybe 15 times that I have been so sure in my heart of hearts that I was right and she was wrong, and I sort of magnanimously said to myself, I'm just gonna let her make this mistake right now because I'm such a big person, guess how many times out of that 15, it really ended up being a mistake?
I'm gonna say zero.
Like one. So I've also learned to actually doubt myself when I get that pure sense of Rightness. But you know, working as a couple I think has been a beautiful experience for us because we've put the business on a lower tier than our self development and our full life act and making mistakes and doing things wrong and learning on the job is a part of our journey and we give ourselves the space to do it. So no, we don't step on each other and we don't come into each person's part of the business and say you're doing it wrong. We give each other a lot of space and a lot of trust and respect. And the funny thing is, Carrie will secretly admit to you too. You know, gosh, there's so many times when I just know it's going to fail the way that Demir is doing it. But it succeeds amazingly. And so we've also built with that attitude a sense of respect for each other.
I love hearing about the two of you as a couple, as the holding company or as Chamath Palipatili would say it like the Topco that the top co holds everything else. And it gives new meaning to the term lifestyle business, which I've always just never understood the derision that some people use when they say that. Because shouldn't every single business be a lifestyle or a life giving business? And why run it? I mean, I know there are some founders that are so passionate about world domination or growing something. An incredible, incredibly vast vision. Like even I just finished watching Wecrush and you see the vision that there's WeWorks all over the world and it's cool.
We'll be right back just after this.
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I just love how you describe that. The business itself is there to serve the two of you and in a virtuous circle of the greatest good for all involved within the business. I'm curious, tell me specifically, how do you two divvy up the work? And then what do the five full time people on your team like? Can you give us a little bit of an overview? You don't have to go too detailed, but the five full timers, what types of business things they're working on and even the 13 contractors because that's a lot to juggle talk about. You must have really smart systems to not get bogged down by all the managing logistics.
Oh, well, now let me be clear. Some of those contractors work once a month for us, right? So when I say 13 contractors, some of them work 40 hour weeks for us. And some of those contractors might work two hours a month for us, right? Just a vague number of like, hey, we use them when we need them. The way that we divvied up at first, you might find interesting. So at first there were no contractors, there were no VAs. It was just me and her. And so what we did was we created a list of every single job that had to happen in the business and we auctioned it off, meaning it was sort of like we created a list. And I turned to Carrie and say, what's your favorite thing? What's the thing that you want the most in the business? And so she said, I want to be able to control the finances. And so I said, great, you can have that. Then she said, well, what do you want the most? And I said, well, I want to be able to influence content and the direction of our message. Okay, great, so you can have that. And so we started going down the list. And the very top of the list is the things you really, really want. And at the middle of the list are the things that maybe I don't like as much, but she actually doesn't have an aversion to you and maybe even might like a little bit. And you keep auctioning it off all the way until you get to the bottom of the list where these are the things that it's just a question of who hates it.
Now, the reason I say that is because when we would call it captain. So finance Captain, Content Captain, right? When Carrie got finance captain, what she got was 51% of the decision making capability. Meaning if Carrie makes a decision, she'll come to me and say, hey, what do you think about this? Or I'm about to do this and I'm not agree with it. I might say, hey, I wouldn't do that. But the conversation always ends at hey, it's your call. You wanted my opinion, now you have it. But I trust you go for it, right? And so that's how we avoid in the beginning, how we avoided some of those sort of deadlocks of like 50, 50. There is no 50, 50 in our business. If you are a finance captain, if you are a content captain, if you are sales captain, your word goes and the other person doesn't get to say nothing about it. Now, when we started adding people to the team, guess where we pulled from? We pulled from the bottom of the list. We pulled from the things that we really hated doing. So that meant that our life started getting instantly better because we were doing more and more of the things that we either hated less or liked more. And at this point now I have a life where I'm doing that top 5% that I think I'm really good at, where I add a lot of value to the business. But frankly, I also really enjoy it. I love being here talking to you right now. This doesn't feel like work to me.
I know. This is the best. And you have a podcast too, right? It's like a big failure that I'm not already subscribed to it. Freedom Decoded, right?
Freedom Decoded is the podcast. It's a little bit of a behind the scenes look at how we power our freedom lifestyle.
See, I really love. I agree this does not feel like work. And I also love what you said in the earlier conversation that a lot of people you work with, I mean, you could get your week down and I've heard you talk about in other places, could be as little as two hours a day or two hours a week. However, a lot of people, when they really genuinely love their work, four hours a day is a sweet spot. Going back to that term that we want to work. Like, I feel good when I work and I get big things done. So that brings us to winning the Week. Before we get into how to win the week, I would love to know what finally inspired you. Or not finally, but deciding to write a book is a big undertaking. How did you come to know that this is the time and this is the book?
Well, you should also know that I'm pretty famous in my little community for saying that we don't need more books in the productivity world. So obviously I also had a bigger burden of proof to move past because so many people had heard me say, we don't need more books, don't read more books.
And there's so many giants like Tim Ferriss, David Allen. I had the same thoughts, like Michael Hyatt. The one thing like, there's so many giants in this space that I don't know about you, but they have changed my life. Like, who the hell am I to write a book.
Along these lines? I'm sorry to interrupt.
Keep going. Oh, no, I completely agree. You know, the way that Carrie and I see ourselves, if David Allen, Cal Newport. If some of these People are what I would say, researchers, meaning they're right at the bleeding edge of concepts, ideas and frameworks that are really going to change how we operate. We think of ourselves more as clinicians, meaning we're here to take a lot of those deep ideas and actually integrate them. Because as well meaning as, for example, a Cal Newport is, and you couldn't get a guy who was more well meaning and doing more good in the world, the truth is that he doesn't have a burden of telling people how they need to integrate this come Monday morning. And so what we saw when we started the work that we do is we saw a gap of saying, okay, there are so many great ideas out there, and frankly, so many great ideas that if we could just integrate on the ideas that we had in the productivity space right now, people's life would be transformed. And yet what's happening is they're getting more and more overwhelmed because they're reading more and more books. And if you read a thousand books, 250 are going to tell you to go up 250 down, 250 to left, 250 to the right. And I've seen clients come to me and say, wow, I'm actually less likely to take action right now because I've got so many ideas swimming through my head, I don't even know where to go now. And so I'm a passionate believer in the idea that we don't need more ideas. So, okay, hypocrisy alert. Then why did I write a book? Right? So why would I have written a book? And so one of the interesting things is I met a really mean client. And you've probably had people like this, you know, people that are just like, how did you get into my community? You were just so mean. And this guy sent me an email. And this is when I was naive enough to get on the phone because I was like, oh my God, somebody's mad at me. So I got on the phone with him and this guy was just a troll and a bad overall person. And he came at me sort of like this. He said, I'm going to claim your 30 day refund. I haven't watched any of your content or done anything. But even though I'm walking out the door, I want you to tell me the one thing that's going to change my life and my productivity. And I thought, of course. My first instinct was like, go to hell, I'm not gonna teach you anything.
Yeah, yeah. But what was interesting was the elegance of the question. Meaning I got Obsessed with this idea of, like, if you could only teach somebody one thing, like, if you knew you only had 30 seconds of somebody's time or 30 minutes or even an hour of somebody's time, and that they would never, ever work with you ever again, what would you teach them? Because I think, Jenny, this is what I call your patch, your code patch. I feel like if we're lucky, as thinkers, as thought leaders, we might be able to patch one broken piece of code in the broader culture, Meaning we can get one idea out there into the broader culture and say, let's just patch this one broken piece of code, because if that's all I could do, it would be worth it. And that sort of kept worming its way into my head, like, what would my one little piece of code be? And the answer just kept coming back resoundingly. People don't know how to plan their weeks, but the problem is they think they do. And so what's happening is we've got legions and legions of people walking around with their shoes on the wrong foot, happily pointing themselves and say, look at how well I tied my shoes. It's like, oh, my God, like, imagine if you walked around the planet and everybody had the shoes on the wrong foot. You would be going mad. You'd be screaming from the rooftops, please, people, I've got to tell you something. All you have to do is switch your shoes onto the other foot. It'll be so much more comfortable and so much happier. And so this was the brain worm that got us writing the book. The way I think about this book is if I never write another book, this is the book that I wanted to get out there. This is the piece of information I want to get out there. Because people think they are planning their weeks correctly, and they absolutely aren't.
Okay, so you've got to tell us what is the biggest mistake that people who are well read, educated have read all the business, time management, productivity books. What mistake are we making? And I mean, you could get into the whole winning the week method. I would love to talk about your weekly planning at a Parisian cafe or similar.
Yes.
But I'm just so curious what smart people who have read what's in this space are doing. Like, we know the people who've never read a book in their life. There's so much room for improvement. Well, I want to know what the mistake is that you think, like, smart, well read people are making. And the very first thing you recommend to turn it around, put the shoes back on the other foot, let's put.
Some data to make this interesting. So we surveyed 5,000 people who managed between five and 50 people. So a subgroup of people who's pretty successful has been recognized by their peers as being management worthy. Right. Successful people. And we asked them, what's the most important qualities to winning your week in the top three of 94% of the respondents, the most important thing in their top three list would have been planning your week. Duh. Right? Okay, so obvious statement of the year. If you want to win your week, you have to plan your week. But then this is where it gets interesting. We followed up with that same group and we said, okay, if planning your week is so important, have you done it for the last four weeks in a row? What percentage, Jenny, would you guess? Out of the 5,000 people who had just said that planning your week is one of the top three things you need to do to win your week, what percentage would you guess had a consistent planning practice in place?
I'm gonna go with 30%.
6%.
No, 6%.
So this was really consistent with what I saw. I would be working with clients and I would say, are you planning your week? And they'd say, yeah, I am. And then when I got in with them, I realized that what they were calling planning was not planning at all, which is dangerous when you think you're doing something and getting the benefit, but not doing it at all. It's like putting milk in your gas tank, right? Yeah, I'm filling up the gas tank.
And why weren't they doing it? Does it become like eating spinach? You know, one of these things where it just becomes a shoulda? Because I think systems that are intrinsically useful, it hurts not to do them. So why did so many people drop the ball on this?
Okay, let's be honest about the very nature of planning. Planning is like getting a slap in the face on Friday for the coming week instead of a punch in the face the next Wednesday. Right. Meaning it is not a great deal, no matter how you slice it. I mean, obviously, I'd rather get slapped in the face than punched in the teeth, but I don't want either of them. And so we have to recognize, and this is really step one in our process, we have to recognize that your animal brain is designed to move you away from pain and towards pleasure. And the nature of planning. And really hear me when I say this. Planning, even when done perfectly right, is anxiety and fear provoking. Even when done perfectly, planning will provoke anxiety and fear. Because what you're basically doing, Jenny, is Taking a week's worth of what could go wrong and shoving it into 30 minutes of planning. Of course, you're not going to look forward to that. Of course your animal brain is going to start to build a resistance to that and say, gosh, I don't feel good when I think about planning, so guess what? I shouldn't plan. And that's when we get these planning sessions, the shoulds of like, oh, I've got it on my calendar. I know I should do it. And then 94% of us are avoiding our planning when it actually comes around. And so the first step in really getting a solid planning habit is do what I call recognizing the resistance and removing the resistance.
How do we do that?
Well, the best way to do it is to make your planning session itself a reward. And so in the book, I talk about how my wife and I went to Paris. This is what you alluded to.
Yes.
We were in Paris and we had a day when we had, like, 12 hours to kill before we got on a plane. Whatever the nearest cafe is, let's just go sit down and open our laptop and do some work. And we went to this cafe that was so cool. It was like a Kodak moment. I mean, I felt like I was a thousand times cooler just sitting in this cafe with the cool French people and the baguettes. I mean, it was like, if you're a Francophile, this was literally a Kodak moment of the most perfect Paris experience you could possibly imagine.
By the way I smiled reading that, because even when you described in the book, you're like, I still remember it to this day as if it was yesterday. And I could feel the joy. I could feel the delight. I could feel how it had imprinted this experience in your mind. So I didn't mean to cut you off, but it is so tangible how brilliant that moment was.
Yeah, I can see it if I close my eyes. I can literally see it right now. And what was funny is we opened our laptop, it was Saturday, we did a pre planning session, and my wife made this really smart comment when we were leaving. She said, wow, it is like dragging ourselves and pulling fingernails to get ourselves to plan at the kitchen table on Saturday or Sunday. But, man, I could do it like this for the rest of my life. And that's when the light bulb went on for me. Wow. When we came back, we actually found a really incredible cafe, sort of total French bistro vibe. And I actually scheduled us to do a sort of French Paris planning experience. And that has become a routine for us years running now, meaning every single Saturday morning, my wife and I have a couples date where we go down, we take our laptops, we pre plan our week in 30 minutes and then enjoy each other's company for another two, sometimes three hours with the little baguettes and the croissants and the whole thing. We do it every single Saturday. And the funny thing is, now instead of dreading planning, I look forward to it because instead of trying to drag myself to the kitchen table and make it a should, now it's a want to.
I just love this. And you even describe other ways to make this joyful. One of your clients, like, makes two croissants for herself, right? Keeping in the French theme. She has one at the start of her planning session and then one at the end.
Just so cool. Like how to create a pleasurable environment around the weekly planning process. Just like you did with Carrie.
So crucial. Because frankly, I mean, I would love to go into the weeds with the rest of it, but frankly, that's what most people are getting wrong. When people don't recognize that it is an inherently stressful process and that in any inherently stressful process, you will build a resistance to it. Your animal brain will slowly but surely get to a point where it says, let's get away from this. This is stressing Jenny out. Let's move Jenny away from this. That ultimately that's going to result in something where you've got a resistance to it. And if we don't recognize that resistance and we don't change our environment to create a planning environment that is a reward in and of itself. I can promise you nothing else I say is going to work if you don't do that.
You also talk about, along those lines, putting the good stuff in first. And I think you're right. Some of the stress of planning the week comes from the guilt of what we didn't get done in the current week. And then the potential overwhelm of what's on our plate. The following. And we probably are both familiar with the saying, don't write a check your body can't cash. I feel that we do this so much with our time. And you talk about it in a brilliant way. I love how you say your time is your inventory and that we, when doing this weekly planning, you say, match your time demand to your time supply. This is Econ 101. And yet we so often don't do it. We put too much demands on our time, even in our head, and then are inevitably disappointed when the time Supply runs out. So I would love to hear. Let's say we put the good stuff in first. You say stack deep work at the start of the week. Is there anything else? Like the game changing lever of during the weekly planning session, making it fun, putting good stuff in first, deep work at the start of the week. Anything else that you've seen just really be a game changer of matching that time demand to time supply.
I mean, what comes to mind immediately is putting in flex time. We call it UUW time. UUW stands for unplanned unwanted work. And what's funny, Jenny, is I get clients who will come to me and say, oh, Demir, I didn't get what I said I was going to get done this week because of this thing that dropped on me. My boss assigned me this new thing, or a client brought this crisis to me, and I'll say, okay, cool, understood. But how many weeks out of the last 52 weeks did you have something like that? And they'll say, well, 100%. Every single week, something happens. And so it's sort of a victimhood mentality, isn't it, to know that we're going to have a UUW hit us next week. It's happened 52 out of the last 52 weeks and yet not put it into our plan. So when you bake flex time in, what you're really doing is you're taking radical ownership and saying, even though I've planned it as well as I possibly could, I also recognize that there's something additional that's gonna happen this week, something new and novel that I could not have foreseen is going to come, and I'm going to set aside a little time to deal with that. And so that's what I call UUW time. It's flex time that you build into your week to deal with the landmines that you couldn't have possibly foreseen. And I would say the number one Rookie move that 100% of my clients make when planning their week is they put zero flex time.
Yes, flex time. UUW time. I love that abbreve. And then I'm noticing email time. Like, if I don't add email, it's kind of an event diagram, sometimes overlaps with UUW that will be like, oh, it's a message from my accountant and I have to do something about it. Or, you know, there's all kinds of uuws that sneak in through the inbox. That takes time.
Okay, that's pretty much what an inbox is.
I know Right.
A whole connection of other people's priorities that they're dropping on you and telling you, I'm so sorry, but I need this tomorrow.
I know. Okay. I would be remiss if I didn't ask you about the Sticky Focus Game. Tell us how to play.
You know, the Sticky Focus Game has gotten really popular in our community. It's basically like the Pomodoros but way more gamified. So a lot of my clients call it Pomodoros on steroids. And it really simply is looking at the open amount of time in your day. So let's say out of a six hour day, you actually have three hours that isn't accounted for, meaning you're not in meetings, you're not driving the car. Like three actual hours that you could get work done. Pulling a sticky note out and for every single hour, just slapping it down on the table and writing down what you're going to do in that hour and then starting a timer. And while that timer is running, trying to block out the world and race yourself. The point here is to truly get yourself into a game forward type of brain. You know, when you see like, like a nephew or a kid or if you were a gamer in the past, there's this sort of blissful state that you can get in gaming where you're doing something really hard. But frankly, people could not tear you away from it if they tried. What we would love to do, wouldn't we, is bring that same type of intensity to our work. And we can, if we gamify it. I'll give you the simplest example of gamification. When I want to go out the door and my wife is not yet ready to leave, maybe, but I've got 10 or 15 minutes I will time and gamify cleaning my living room. Meaning I'll say to myself, gosh, I wonder how much of this living room I could clean in the 10 minutes. And I'll set a timer. And I'm now playing a game against myself, aren't I? I'm playing the game of how much of a dent can I put in this before she's ready or before this 10 minute timer goes off. And you would not believe, Jenny, how effectively I can clean in 10 minutes in these little 10 minute spurts. And so conceptually that's what we're doing in the Sticky Focus game is we're actually showing people a game to reengage a different part of their brain and take you away from the I have to. Oh God, I need to. Or what I should be working on is this. And get you into the place of like, gosh, I wonder what kind of a dent I could put in this project in just 30 minutes or in just 50 minutes.
Yes. That's so fun. I love that I actually created. It's funny, I didn't connect the dots until just now as you're saying it, but I have an email tracker that I built in notion that it says the number when I started, the number when I finished. It calculates how much time per email. So in a way it creates a little satisfaction for me that I just see these numbers totaled for any given email sprint because otherwise it feels so endless and never ending. And my way of gamifying it is just showing myself some stats about that session. And I love the house cleaning one too. Yeah. And like throw on a podcast, set the timer and then make it a game. There's even. I don't know if it's a spoiler alert or not, but I was so delighted when I got to the end of your book and there's a little badge and I felt like you gamified the book. I felt proud. I got a badge for reading it.
You got the badge. I love it. I love it. Yeah.
I mean, I've never seen it.
To me, you know, we have a built in mechanism for learning and accomplishing. It's called playing games. But we live in such a serious culture. Frankly. If you see somebody having too much fun at work, you think one of three things. Either A, they're insane and we need to send them to Looney Bend, B, they're not taking it seriously enough or C, they need more work. Right. And so there's something inherently wrong with the way that we've structured work when those three things are the first thing you think if you see somebody blissfully happy and engaged in their work.
Yeah. Or that they have some magical energy source that allows them to be having so much fun and getting so much done.
I think you nailed it. I just think, isn't it so sad that when we look at people who are truly, deeply joyful in their work, the first thing we think is, well, something must be wrong. Are they on drugs? Did they just get converted to a religion? It cannot be possible that they're just genuinely joyful in their work and it just shows you how much work we have yet to do. Myself, you, and other people who are looking to change what I call the productivity problem that we are starting from a really sick place.
We'll be right back just after this.
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There's so much software that can be used for good, but then there's so many platforms that we're part of now, even if I'm not even on social media. But the nature of our work now is so ubiquitous and digital and 247 and all consuming that I do think we're all individually up against much more than we might have been 20 years ago in different ways. I mean the culture is also evolving to talk more about mental health and work life integration. I'm curious to know. I think any book tests the author like are you sure you know what you're doing? Are you sure you know what you're talking about?
Totally.
And gives you some tests from the universe to say are you sure you're ready to be the go to guy on this? So I'm wondering what did you experience while writing Winning the week method that maybe you didn't expect? Or that you know, were these forging you to be ready by the time the book came out?
Wow, that is such a great question. And I will just co author right? Or co sign that. Every time I do an advanced training we do these bootcamps and every single time I feel like my higher power says oh really? You think you know this? Let me show you a new dimension of this problem that you're not good at yet or you're being a hypocrite at. So I'll totally co sign that. But I will have to say the honest answer is that as I was writing this book I really just got more and more sure meaning at the beginning of the book I wondered can this topic be a book? And so I was willing at some point in the book to say, you know what, this will just be a long blog post and not a book. As we kept writing it, I just found new layers of this onion. So I was gifted at least with this first book, with a sense from my higher power that this was exactly the right choice, that the topic was the right choice. And this is what we wanted to sort of where we wanted to plant our flag and the little piece of code that we wanted to try to see if we could insert into the broader matrix.
I just love this idea of the code patch and giving ourselves permission to patch a code over gaps in the world's knowledge base. It's a beautiful way to think about it. Demir, I could talk to you all day. Last question for now. I have a feeling you're going to be back if I feel excited.
Well, thank you.
Last question for now. If you could give fellow business owners permission to do something differently or drop something altogether, what would it be?
What a deep and great question. I love that question so much that I really want to give it a moment.
Yeah, take your time.
I mean, I know this is so topical and it sounds like I'm really just speaking my book in a very literal way, but I would say the number one thing that creates the most lift in your productivity is planning your week every single week. I can say it with 100% biblical certainty, but very close behind, the number two thing is running weekly pre planning sessions with your team. And I would say almost every single small to mid sized business owner that I've taught how to plan their week has then gone on to plan their week with their team. And I say this because.
You can solve a lot of your own productivity problems, but if your team still isn't looking into their week and catching their landmines very quickly, you'll realize that a solid 60% of the things that are hitting your plate are actually coming from other people, not looking into their pipeline and not being responsible with what's coming at them. And so I would say yes, you must plan your week. It is the number one thing you could do. But very quickly behind that, if you're in charge of an organization or in charge of other people, even if it's just one or two other people, you'll very quickly want to actually sponsor a weekly planning session with your team. Because I have to say, probably the smallest thing that you could do as a team to get the biggest lift in your team's productivity is simply making sure that we're all looking down the pipeline, whether that's the next week or the next month, and checking what's coming at us because the number one source of UWS is is usually avoidable. Most of the things that land on my clients plates when I really track it back, it's just somebody didn't look into their week properly. They didn't look into their month and it really wasn't an emergency. It just became an emergency because they didn't see it coming out far enough.
And did I hear you call those a weekly pre planning session or just a parallel weekly team? What's the pre planning session?
I call it pre planning. Now pre planning is actually a word. I've been called on this and people say pre planning isn't a word, it's planning. Planning has to happen. I had of time. No actually pre planning is a word. Check it out. But I call it preplanning because guess this is another funny quiz. Jenny, guess the number one day that people plan their week. Which day of the week is the number one day that people plan?
Oh, I'm so bad at these quizzes and I like pre planning can be part of your code patch. It sounds redundant, but it isn't. Okay, the number one day people plan their week. I'm going to guess Monday or slash Sunday night when they have the Sunday scaries.
No, by far it's not even close. The people who actually do plan their week and they're vanishingly small proportion of them, they actually try to plan it on Monday. So not only are we not doing planning, we're also doing it on the worst day, meaning the most stressful. If the battle started, would that be the best day to actually start to create a battle plan? God no. I mean if the bullets are whizzing past your face, let's hope you already have a plan in place. So I say pre planning just to reinforce that it is not a plan. If you didn't make it ahead of the battle starting that whatever you're reacting.
At this point, you're saying a lot of people plan on Mondays, which is not what you recommend.
Just like I wouldn't recommend you go into battle without a plan and then say we'll figure it out in the trenches when the bullets are flying and the grenades are exploding. That is the worst frame of mind to be in to actually responsibly create a plan. So when I say pre planning, what I mean is do it on Friday night, do it on Saturday morning because you get a one plus one equals ten effect, meaning by going to a wine bar with your wife or doing it at your work with a pizza with everybody Congregated around, you get the ability to create a plan for the week and then go into your weekend and oh my God, imagine what it would feel like to have a plan for the week and actually go into your weekend. Become a full person, live joyfully without that part of your brain that's constantly buzzing, thinking, oh God, oh God, oh God, what's coming at me on Monday morning? And so the double win here is you're going to do a better, more strategic, more impactful plan on Friday or Saturday morning. But you also get to give yourself the gift of becoming a person again and not having that whole part of you buzzing around like a negative fly thinking, oh no, what's coming at me this Monday? Oh God, I don't even want to look.
And there is something, I call it the crush of the inbound that just ramps up so high on Mondays that, yeah, I'll just leave it at that. But the crush of the inbound is real. And I notice I am the happiest by far when the rest of the world is on vacation. So like the holidays, I usually create really big projects and I don't know as much as I could set my own schedule. There is still something so glorious when the rest of the world has a day off and the crush of the inbound is just inherently lower. And you know, there are ways to gamify that too and turn it off and all the. But I just love this idea of making it joyful and not on a Monday. So we go into Monday feeling free and clear and planful for the week ahead.
Absolutely amazing.
Tamir. This is so fun. Tell us everything where people can find you and keep in touch. And listeners, be sure to check out the winning the week method.
Yeah, so you know, part of what we want to do is become the Johnny Appleseed of this concept of just learning how to plan your week correctly. It really isn't rocket science. We do it for free@winningtheweek.com so if you don't want to buy our book and aren't interested in that, no problem, go to winningtheweek.com, we have an hour long training and just grab that. And if that's the only thing you ever get from us and you never interact with us again, then I will die a happy man. Now, everybody who goes there and exchanges your email in exchange for the hour long training, we will follow up with you and let you know when the book is published. So if you do like what you saw and you want to go a little bit deeper, then you could jump into the book if you like.
Amazing. Thank you so much Tamir. This was a real treat and I think you're onto something with some modus content around team planning and what you've learned and who knows, could be a next book. Just gonna plant that seed.
Ooh, I like that. You know, we've been looking for bonuses to include for pre sales, so maybe we'll make that one.
Yes, I hereby request because.
I think yeah, that's something that it seems like you've honed in on really well and I just love the idea. Yes, I'll pause there, but I just love the idea of helping people click into a groove and even gamify with their teams. That would be amazing. Thank you so much. This is such a joy to chat with you today and thank you Selena for putting us in touch.
Thank you Selena and thank you Jenny. This has been a blast.
Yay. And big thanks to everybody who's here listening.
If you've listened this far, you get a gold star.
Thank you.
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