The Calendar System for Scaling Businesses and Taking 2-Month Vacations

This may be one of the most important podcasts that I record for you. And it's because I'm going to share my system for taking control of my calendar. And the reason I say one of the most important is because, you know, you've heard it before: time is your most important asset or your most valuable asset. And I fundamentally agree. And when you master how to manage it, or even improve how to manage it, it has an effect on everything. It is arguably the most important or highest leverage meta-based thing that you can adjust because if you get time management down more effectively, you can manage your business more effectively. You can focus on the right priorities. You can spend time with your family. You can get your health in order. You can, you know, all of the things that are around you that make up your entire life all come down to how you're managing your time. So if you get a better grasp on that, it's going to have benefits everywhere.

So what I'm going to do is just share my system for managing time. And candidly, it's a synthesis of different tactics and techniques and things that I've learned over the years. And it's helped me immensely. And I attribute my like ruthless time management to why I'm able to do most of the things—or all of the things—that I'm able to do. I'm sure somebody does it better, but I feel like I do it pretty well.

Right? Like just this year alone... started a business in January, new business MSP Sales Partners, and we've gone from zero to about 800,000 in that business is probably where we'll end the year. I've added five people—full-time hires—to that business. We've added 50-plus customers to one program and half a dozen to another. Like it's doing very well and we're moving the needle on the right priorities.

And I've been able to do that while I've been able to create content every week. You know, like every week I haven't missed a newsletter, I haven't missed a YouTube video, you know, it's the podcast, everything else that we have in our content machine... I've been able to sit down and record the content that I wanted to record. And I've been able to have dinner with my kids almost every single night. I've gone to most of the kids' functions—or all of the kids' functions I need to be at, most of them in general. And, you know, we've taken the traveling basketball throughout Baja... and taking the family traveling for that. We traveled for two and a half months over the summer, bouncing around to Florida, Virginia, Texas, North Carolina. You know, we took a family trip where I actually completely checked out to Spain and Italy and France.

And I've been able to manage my exercise the way that I want to, which is... it's a little extreme, but it's you know about seven days a week. Typically 90 minutes to two hours of walking, running, weights, whatever I want to do that day. And I attribute time management to being able to do that. Right? Like I can't do all of those things unless I get that one thing right.

So this is my system. You know, conceptually I think we all agree: "Hey listen, we all get 24 hours in a day and if Elon Musk can use it to build 27 billion dollar businesses then you can use it to do what you're trying to do." And it's true. Like in theory we're like, "Yeah totally get it." But in practice we go, "But how the fuck do you do it?" Like what is an actual tactical way of managing it? So this is what I do.

And really what it comes down to is one core principle, which is shifting how you manage your calendar from reactive to proactive. And like basically moving from playing defense with your calendar—and letting other people fill it with what you see in your inbox and the requests that they make of you and the tasks that show up on your plate and the client demands that you have—and shifting it from a defensive mindset to an offensive mindset. Right? Where you're looking at your calendar and you're getting the things that you need in there first, and the rest of it can get filtered in as necessary. Or it gives you the filter that you need to say no to everything. Right? Like you look at it and you're like, "Well shit, there just isn't enough time. I've put in the right stuff, I've gone on offense, and now there's not enough room to fill it with shit." Right? And the stuff that doesn't really matter and the stuff that we end up wasting our time on throughout the weeks and the months and the year. And we look back and we realize we clocked a lot of hours, we didn't move the needle where we wanted to. That stems from having a reactive and a defensive mindset to time management and taking more ownership of your own calendar and what needs to be in there and pushing out all of the stuff that isn't going to actually help you.

Right? So very like tactically... what I would say is the easiest thing to implement is something that I've heard called "The Perfect Week." It's attributed to several different people, you know, so it's... I don't know where the origin of it is. But the perfect week essentially consists of taking a blank calendar. Right? Like if you use Google, Outlook, whatever... like open up a blank calendar. Now sit and think: What would a perfect week look like? If it all... if you had complete control of it. And this works if you're CEO, this works if you're a VP, this works if you're a salesperson. Pretend you have a magic wand that gives you complete control over how you're going to operate the week. And map it out.

Right? And I recommend like mapping out the personal aspect of it too. Like when you gonna exercise? What are you going to leave open for kids' dinner? What are you gonna... you know... what are the important meetings that you have to have? When are you going to be doing your prospecting time? When are you going to be doing your team meetings? Do you have time for vision and strategy in there? Do you have time for content in there? Do you have time for kids' functions in there? Do you have time for date night in there? Do you have time... All of the stuff that you really want. Right? Like you have control in this... in this, you know, scenario and you get to map out what an exact perfect week looks like.

And so plug it in to that blank calendar. And actually block the time out. Right? And look at that. Now, what I would do is take every one of those things that you can put in place—and/or the things that are most important to you—and put them on your real calendar and set that to busy. Set it to busy so that nobody else on all your automated calendars, your assistant, whoever... can steal that time back from you. Right? So make sure to put that time in and box out all of the other shit. Okay?

Now there's going to be some stuff that you look at and you're like: "Well hey, this is really dynamic. And this overlaps with that team meeting that we have. So I've got to shift this around and, you know, my boss or, you know, my big client or something is gonna this is gonna, you know, take this time." And that's fair. That's reasonable. That's life. So to the extent that you need to, take those necessary highly... highly important things, shift them to an hour later or an hour earlier or, you know, move them to another day. But make sure that they're on there.

Once you've got those locked in, start taking everything else that's left and start filling in on your actual calendar where those go. Name them. And you can set 'em to free if you have to. And if they... if they get stolen... uh, okay, like then you've got to manage it. I'm actually very... I'm pretty ruthless with it. And my shit's blocked. Like almost... almost all of it is completely blocked. And you know I know that that's gonna mean some people are disappointed or say "Hey, you don't have any availability for three weeks" or you... Yeah. That's the reality.

There's no more important thing than how I manage this asset. How I run this process is probably the thing that's going to make me a good dad, a good husband, a healthy person, and a good CEO. So I need to step up and fucking own this and be willing to make some hard choices and have some hard conversations. And if you're not in a position where you're the CEO or you get much more latitude, then that's okay. Like own the elements of it that you can. And to the extent that you need to, like go have conversations with people. Be like, "Hey, this meeting's on my calendar every week. It's a recurring meeting. Like this is something that I frankly we could shift to, you know, bi-weekly. Or this is something that we could shift to an async video. Right? Like I can drop you... instead of us having a 45-minute call every week, why don't we... why don't I drop you a 10, 15-minute video and with an update and I'll write it out in a memo too and that'll suffice. And if you have any questions, let's let's hop on a call." Something like that.

And I can't tell you how many things that sit on people's fucking calendars could just be shifted to a Loom video and, you know, an AI transcript run-through of a summary of the video and say "here you go." And and condense 30, 60 minutes down to 11 minutes, you know, doing async stuff. So have those conversations. Right? Like be willing to go to your boss, to your manager, to whoever and say "This is what I'm trying to do. And tell them what's in it for them. Hey, by doing this, here's what... here's what it's going to mean. I'm gonna have more time for prospecting. I'm gonna have more time for outreach. I'm gonna have more time for sales calls. I'm gonna have more time for project management." And and that's how you manage up.

Managing down, you do the same thing. Or even across. You have... you have those conversations and say "This is what we're doing, this is why I'm doing it, here's the benefits to the organization, here's the benefits to the team." You can have that same conversation with your spouse. You can have that same conversation with anybody else about "why I'm doing this." People are not going to love it. But if they at least understand the context and the reason behind it and the impact that it has on them, then go, "Okay. I guess like... so you're gonna make us more money with this free... Okay, let's try it." Right?

So, lock those things in. Set it into your calendar. Then, every Sunday, block an hour and sit down and look at how your week really went compared to the perfect week. Audit it. Right? Cause it won't go perfectly. Like it's... I mean even mine... with as much control as I have, shit happens. And so things do shift from time to time. I have a handful of non-negotiables, but there are things that... there are pieces of the calendar that are a little bit more dynamic.

So every Sunday sit down and look: How did the week go? Like what what did my calendar actually look like? What did I actually spend time doing? And what did I say would be a perfect week? And why is it off? Like what's the source of it? Were those things valuable? Were they useful? Did they move the needle? Uh, were they high leverage? Were they impactful? If not, why did they happen? How did they get on your calendar? And then dig into that and figure out what the root cause is. Where are those coming from? Is it the lack of a process? Is it the lack of a system? Is it the lack of communication? Is it the lack of something else?

Right? So audit it. And then fix it for the upcoming week or two. So look at your calendar going forward. And I... especially when I was getting started with this... I would do that audit on Sunday and I would look at the week coming up and I'd go, "Oh my god. Wow. I can just like free up about 8 to 10 hours right now." And I just send emails. Like, "Hey, we're not gonna do this, I'll send you an update at the end of the week. We're not gonna do this one, let's just switch this to bi-weekly. We're not gonna do this, boom boom boom boom boom." And I would immediately get all of these blocks of time back and have that to focus on the higher leverage work.

Now I I always keep that like the stuff that's really important to me... that's like... that's blocks. People can't book into it. But even the stuff around it, you know, we could just... I could just zap it the next week or two. And so it keeps the trend from accumulating back. Because what I have also noticed is that when you do this exercise the first time, you get this bolt of energy. Like "Oh, this is awesome." And then four weeks to six weeks later you look at it and you're like, "I'm just back to homeostasis." That's the point of the audit. Right? Like every week you gotta look at it and then fix it for the upcoming week or two and you keep it from going back to what it was and you establish a new homeostasis. Right?

Now, that's kind of like the the weekly system. I've actually started to to zoom out and move that to a quarterly system. Right? So I actually take one day off per quarter... uh towards the end of the quarter... and I I go off site. I've actually turned this into... I go off site for like Friday and then, you know, I pick like a resort 'cause I live in Cabo, it's like across the street. So I I pick the resort on Friday. And then I invite the family and they come on, you know, Friday night or Saturday and Sunday. We make like a little staycation out of it. So my family loves strategic quarterly planning.

But I... you don't have to do all that. Block time once a quarter and look at it and I identify: What's the major constraint to the business right now? Like what's what's what's the bottleneck? What's the biggest problem that I have? And what are the one to three things that we as a team can do to attack it? Now modify this if you're not running a business, you know, to you know to the one core thing keeping you from getting results or something along those lines. Um, but I identify: what are the one to three things that we can do to attack that individual constraint? And then box out the time to to attack it. Update the perfect week. Right? Like update the weekly calendar to to align with what you just went through and planned out for the quarter. And then use that as a filter every week for your audit.

Right? Like, "Hey are we doing the three main things that I said were going to do or the one thing that we said we were going to do? Or are we moving the needle on the one thing that we wanted to? That stems from having a reactive and a defensive mindset to time management and taking more ownership of your own calendar and what needs to be in there and pushing out all of the stuff that isn't going to actually help you."

Right? So, very like tactically... what I would say is the easiest thing to implement is something that I've heard called "The Perfect Week." So some people actually zoom out further to annual. Um, like I think Jesse Itzler has some some stuff for like the "Big Ass Calendar" and he does like a whole annual planning. I have not done that. It's... it's my own belief system or something. I think I like a more dynamic, more flexible system. Um, I find that the further I try to plan out, the less realistic it seems and the less I truly believe it. Right? Like if I think... so I don't love like fucking 10-year plans in a business. I'm like, dude... six months... like that shit's going to be irrelevant. Right? Like so... I think the further you plan out, the less believable it is and if I couldn't create the team dynamic for whatever reason... because of a board, because of a... you know just a any number of issues... I'm out. Like I'm not interested in it. Because it's not just the track record, it's not just the experience. It's also your time there. Whether you own the company or you're just a first... you know... this first in selling, doesn't matter. Your experience there will be dramatically different when you spend way too much time at work or doing work to be at a place that's subpar, suboptimal.

So if you haven't experienced it then you know. If you you haven't, and you're thinking "Okay like what do I what do I do with this?" Well, if you if you're in a position to hire, start thinking about how do I hire the right people? Not just the right players. In other words, how do I hire the right person that's going to add to the dynamic and add to the culture and help recruit and raise the standard of everything and help everyone else? Like a person that comes in and you go, "Hey, like that's... that's a good addition." You start stacking those people together, you start building a team. If you're not in a position where you can hire, then, you know, think about joining a legitimate team. Like if you're if you're talking to other employers or you're talking to, you know, people that you, you know, other partners, whatever it is, then talk about that aspect of it. Not just the day-to-day. Not just the checklist. Not just the specific responsibilities. But how do you guys work well together? Like how do you guys support each other? Like what's what's the common goal? Can I talk to a couple people? Right? Like that's... and that's we... when we did interviews, we'd let people come in like, "Hey, bypass me. Talk to them. You know, talk to them about what to what to expect."

So think about that. And if you kind of apply this filter, from my experience, you're going to end up not only putting a lot more W's on the board, um, but you'll enjoy the process as you do. Adios.