Jan. 15, 2026
From Overbooked To In Control: A Practical Guide To Strategically Selfish Scheduling
Ever feel like your calendar is packed but your real life lives off to the side? We dig into a simple, no-fluff system to make every commitment visible, merge the hidden to-dos with the scheduled ones, and carve out protected time for sleep, movement, and deep work—without the guilt. The result isn’t more hustle; it’s a calmer, truer plan that helps us deliver for others while finally honoring the projects and habits that matter to us.
We start with a quick refresher on guilt-free future planning: capture big goals, weigh them with a practical matrix, and set a clear order. Then we hit the wall most of us face—there’s “no room” to schedule priorities because our calendars only show meetings while errands, caregiving, community roles, and recovery time sit invisible. That’s where strategically selfish scheduling comes in. We do a one-week extraction of every commitment, including the off-calendar certainties like grocery runs, bedtime, workouts, and drive time. Seeing it all at once breaks the mental negotiation that keeps us stressed and behind.
From there, we run a joy vs obligation scan to expose energy leaks and choose the right lever: eliminate what no longer serves, delegate to someone better suited, automate with tools or templates, or optimize through batching and tighter boundaries. We also make the case for a single master view—overlaying personal and work—so conflicts stop ambushing the day. Finally, we place self-first blocks on the calendar before meetings, naming them clearly and protecting transitions. It’s not selfish to do this; it’s the maintenance schedule for a life that actually works and a career that compounds.
If this hits home, subscribe, share it with a friend who’s stretched thin, and leave a quick review to help more people find the show. Want the time management for construction templates and workshop dates? Drop “double D” in the comments and we’ll send the link.
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00:00 - Why Selfish Scheduling Matters
01:30 - Guilt-Free Future Planning Recap
02:45 - The Calendar Blocker Problem
04:10 - Make Invisible Commitments Visible
06:20 - One Calendar To Rule Them All
08:20 - Simple Extraction Exercise
12:18 - Joy Versus Obligation Scan
15:08 - Preparing For The Firebox
18:28 - Workshops And Next Steps
WEBVTT
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If you have ever felt overwhelmed, scatterbrained, stressed out because you know you're dropping balls, some strategically selfish scheduling is the medicine for you.
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And so, what does this selfish strategy look like?
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It starts with like visualizing all of your commitments.
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And by visualizing all your commitments, I'm talking about getting them out of your head and putting them down where you can see them.
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We're talking about all the stuff that you have on your calendar, whether it's a digital calendar or a paper calendar, planner, doesn't matter, but getting them all out in front of you.
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And then getting all of the commitments that aren't in your calendar, but you've been carrying them around in your head for days, weeks, months, years.
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And the fact that they're bouncing around in your head is what's killing your focus and like taking your energy.
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So, anyways, we're going to get into how to do that.
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And if you don't know me, I'm Jesse, and I've been serving managers, business owners, parents, design their life where they can like be winning at home and at work.
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And the whole point of that is so that they can start sharing their gifts and talents with the world because we need it.
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And guess what?
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I'm here to serve you too.
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Now, if you've been here before, you probably saw us go through the uh guilt-free future planning.
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And so I want to give you a quick review of what that actually looked like and where this whole darn thing came from, right?
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So, guilt-free future planning is again long-term planning, right?
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So, quick review.
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Long-term planning, what do I want to get done in the future?
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For some of us, long-term planning means in the next week or the next two weeks because we're so busy, we can't really see that far, and that's okay.
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For some of us, it's the next three months.
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For some of us, it's the next three to five years.
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Doesn't matter, it's totally flexible to where you're at in your thinking.
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And so, in the guilt-free future planning, what we want to do is get all the things, the big ideas, goals, projects, et cetera, that we want to get done and actually start making progress on them, right?
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And so, part of the challenge there is that we just never make time for ourselves in all of that beautifulness.
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So we get the stuff out of our head and then we weigh them.
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We use the damn matrix to weigh those bad boys and give them some kind of value.
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And then we priority, we walk the plank and we prioritize which one we're gonna start first, second, third, fourth, fifth, sixth, and seventh.
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Now, all of that is simply guilt-free future planning, getting the stuff out of our head so that we can give them weight, give the things, the ideas, give them weight, give them value, and then prioritize it.
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The next step after that is to put it into our calendar.
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And this is where it's like, oh, this is the insight that I got to see again running multiple uh self-first workshops, self-first framework workshops.
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And I got to see so many people were like, ooh, but I can't put them in my calendar.
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It's like, well, why not?
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It's your calendar, just put it in there.
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Like, I don't have space, like it's already full of stuff.
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Like, oh, interesting.
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And then when we got further into it, it's like, okay, you're it's full of stuff, but what stuff?
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And what we found was it's mostly just their work stuff, not all the other things that they do before work and after work, working out, grocery shopping, taking the kids here and there, like all of those other things weren't in their calendar either.
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So, what does that mean?
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Then it's like, oh my God, I just don't have the space to do these things that I need to do to make progress on, so I can start experiencing that fulfillment and serving others to the degree uh that I can.
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So that's where the strategically self-rescheduling comes from.
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It's not necessarily okay, we're gonna populate your calendar, it's gonna be amazing.
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It's really, let's take a real hard, honest look at what the hell we have going on.
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Like for real, for real, I promise, me included, most of us have a tremendous amount of commitments that that we've told people that we're going to do, we're gonna follow through, and we don't even know what they are, like we can't even see them.
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So that's kind of the whole point of this whole thing.
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Now, what I'm gonna do is I'm gonna walk you through the process, and I have the super fancy, fabulistic templates here.
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And if you want those templates, all you got to do is drop double D in the comments, and after the live stream, I'll give you the link.
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Um, it may even be in the show notes already.
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But, anyways, drop double D in the comments, and I'll give you the link that'll get you access to the daily domination template and all of the templates that we're going through today.
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So now we've just talked about the guilt-free future planning, and I just went like super, super rapid, fast overview on the thing.
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So if you want like the deep dive on the guilt-free future planning, the different uh layers of it, just ask for it in the comments.
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I'll give you the link because the I have the replay links on the YouTube.
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So if you want to check them out, you can go hunt for them, or I'll hook you up.
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Just tell me what you want, and I and I'll do my best to get it to you.
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So, back to today's conversation about making space for you in your calendar.
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Again, this is all about like, yes, it's absolutely all about getting more done, being more effective, executing on your responsibilities and tasks, etc.
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Which I'm gonna say, the majority of you people out there like are ballers, and y'all are making stuff happen on the regular with your family, with your job, with the stuff you do within the community, which is beautiful, me too.
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But the challenge was I wasn't making stuff happen for me, like the things that I cared about that only I cared about, right?
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Like my exercise, my working out, my triathlon training, um, at one point in my life writing a book, and all these other ideas that I had that I wanted to take action on, but I didn't because I was delivering for everybody else.
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So the the self-first framework is about making space for you and your big, beautiful grand ideas and bringing them into life one little bite at a time.
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So we're gonna go back into this thing so that we can start talking about this strategically selfish scheduling.
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It's some pretty awesome sorcery.
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So, strategically selfish scheduling, one thing I want you to think about and start getting comfortable with because we're gonna come back and we're gonna dive further into the firebox and all the little quadrants in there.
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But the one thing I need you to start thinking through and embracing the idea of being selfish, and the reason for being selfish is because when you take care of yourself, when you honor your sleep, when you honor your nutrition, when you honor your exercise, you're going to be better equipped to serve the people you care about.
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I know it feels weird.
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I'm not supposed to be selfish, we're supposed to be doing things for everybody else.
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I agree.
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And I also know that if I don't take care of myself, I am not prepared to serve to the degree I was designed to serve.
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So get comfortable with being selfish just for this call.
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And if you need a little backup, just tell your people, like, well, Jesse said that I could be selfish, and then they'll be mad at me, and then you're free, right?
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I'm going to wash away all your sins.
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Now, in this idea, you'll notice on the whole overview of this thing is strategically selfish scheduling.
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There's a white box here, which we're going to spend all our conversation today in the white box, and then there's the orange box, which is the firebox.
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Come back to the next show.
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We'll dive into that bad boy there.
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But in the white box, and here's what I want you to do like right now, right now, I promise it's gonna be a little bit scary.
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And you don't need this template to do it.
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I promise, you do not need the template to do it.
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But if you want the template, again, drop double D in the comments and you'll get the all kinds of templates, all kinds of cool nerdy stuff, so that you can play around with that stuff.
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Anyways, let's go back to this bad boy.
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What I want you to do right now, maybe you don't have your calendar, don't worry about it.
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All you need to do is get a pen or get your whatever you use to take notes, right?
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I'm I'm fancy, I use remarkable.
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I want you to grab that and start writing down everything that's in your calendar, every single little thing that is in your calendar for the next week.
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So today's Saturday, if you're watching the live stream, if you're watching the replay, it doesn't matter, just the next seven days.
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I want you to write down every single thing that's in your calendar.
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I know that feels scary.
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And don't worry about like what day or putting them in any kind of order, it doesn't matter.
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I just want you to get them out of your calendar and start writing them down.
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If you have sticky notes and a whiteboard like I got back here, use that.
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Doesn't matter what you use.
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The key point is getting all of those commitments because those are things that you have committed to somebody else.
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Obviously, there's an expectation for you to follow through and deliver.
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You've got to provide a deliverable for somebody, and you've already accounted for them, and that's a lot, right?
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Like, man, in my calendar, I got so many things, I got all these meetings, I got yes, yes, you do.
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So put them out there so you can see them, and and which seems kind of redundant.
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You're like, Jesse, why the hell would I do that if it's already in my calendar?
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Here's why.
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Because now, once you get all of that stuff out of your calendar, out of your head, here visible so you can see it.
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And if you're not using a calendar, shame on you.
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Start using a calendar.
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And I don't care if it's digital or uh, you know, one of those daily planners, or I mean, hell, I know guys that got the big giant job site calendars and they put all the stuff on there.
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Doesn't matter.
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If you're not using that, start using it, like for real, for real.
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Anyways, now that you got all of the stuff from your calendar written down and like visible to you, the next step is to you ready?
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All the things that you're committed to doing that you have committed to somebody else, that you have told somebody, I'm gonna do this, I'm gonna pick the kids up from school, I'm gonna pick up dinner, I'm gonna go to the quincenera, like whatever those things are.
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My money says you have not put it on your calendar.
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Going to the grocery stores, going for a run, going to bed early, picking up some healthy food, like whatever, all of those things that you know, like right now, for real, for real.
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I'm gonna go visit my mom here in about an hour, so I could eat me some delicious leftovers.
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It's not in my calendar.
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But my calendar has stuff in it, and so now the fact that I'm gonna go like I already planned and committed to go visit mom, but I didn't put it in my calendar.
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What that's gonna do is it's gonna create a little bit of pressure, a little bit of stress because oh man, I'm gonna go visit mom, but I have these other things to do.
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Whereas had I put it in my calendar, I would have been able to see it.
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So, but forget the calendar right now.
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I want you just to write down all of the stuff that is on your calendar and also write down all of the things that you know that you're going to do in the next week that are not in your calendar.
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So if you're feeling a little bit anxious, a little like, oh, what the hell are we doing here?
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I don't like this.
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This feels ugly.
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That's okay, it's normal.
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And and and again, the like the insight comes from working with a bunch of ballers out there, a bunch of make it happeners.
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We started with uh guilt-free future planning, right?
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We got all the stuff, we did the thing, and it's like, okay, here's our big ideas.
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Now we're gonna go put them in our calendar.
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And their first instinct was like, Man, I can't, like, why not?
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Because I have all this stuff in my calendar, but I have all these other things too.
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I said, Oh, what other things?
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All I coach little league, I'm I'm a referee for the volleyball league.
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I mean, all kinds of things, like the people that I have the opportunity of hanging out with are like make it happen, there's or making major investments in their community, and so they have a lot going on, but it's not visible, like they can't see it.
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Or, and I'm not gonna judge you on this because I used to do it, but what a lot of people do that I don't recommend, I know it's difficult, I know it's uncomfortable, and in some cases, like you really can't do it, but that's rare.
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So far, I've only met one person that like technically she couldn't do it because of the arrangements and agreements at work and her contract and blah blah blah.
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But what I'm going to suggest, the problem is we like we like to keep two separate calendars.
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We have a work calendar, and then we have a personal calendar.
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And the problem with I mean, it's good, like actually, then you get a little extra credit if you have both.
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But the problem is you can't see them together, and so you end up double booking and running late to everything and sliding in just on time.
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It's like, oh, I'm sorry, I'm sorry, I'm late, and then you're just praying and hoping that nothing goes wrong so that you can make it to the next thing to pick up the kids, to go to the dinner, to pick up the laundry, to go to the cleaner, like all of those things.
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And so your brain is like constantly negotiating and and calculating what the hell needs to happen and hoping and praying that nothing goes wrong so that you can show up and deliver on the thing.
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Hey, how do I know?
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Because I lived it, and it don't have to be that way.
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The way to break that is to get it all visible, right?
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So you can see it.
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So, folks, if y'all are out there, y'all got any questions, or you think I'm just talking smack, let me know in the comments.
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Like, for real, for real.
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If this ain't landing, um, or or you think I'm in La La Land or I've been smoking some some stuff, uh, hit me up because I'd love to give you some clarity and I'd love to know that like if this is landing with you guys or not.
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All right, so let's go back to the board.
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And I promise I'm not I'm not just trying to threaten you guys.
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I really do uh want to help make things magical and awesome for you, right?
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So strategically selfish scheduling.
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We talked about make a sticky or write it down because you probably don't have stickies and all the things, or if you have a digital whiteboard, like what I'm like showing up on the screen right now, is mural M-U-R-A-L, uh, and it's my tool of choice, but it again doesn't have to be super fancy.
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And so make a sticky note or just write down all the things that are currently on your calendar, okay?
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Then make a sticky note or write down all the things that are not in your calendar.
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And if you feel anxiety, if you feel a little bit of pressure, like somebody's picking on you, it's okay.
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That's part of the deal, that's what naturally happens because this is new to us.
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And then once we get all of that out of our head, now you know what?
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Because I like you guys, if seven days of like all the stuff is too heavy, do three days, four days, five days, but at least absolute minimum three days.
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What are the things that are on your calendar?
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What are the things that are not in your calendar?
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So that you can absolutely see everything that your brain is tinkering with, massaging, wrestling with, trying to figure out how to get it all done.
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Now, you notice I'm only talking about the commitments that we've made to other people.
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We're not even talking about these beautiful things, the ideas, goals, projects that you want to bring in into the world that you keep putting off until someday.
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We're not even touching those yet because you don't have space for them.
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Right?
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What we're doing, the reason, like step one of the selfish strategy is for us to start making space for them.
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Okay.
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And so getting them out of your head, I've said it like 10 times.
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So hopefully you understand that getting it out of your head is really, really important so that you can see what is on your calendar, what is not on your calendar, you can see all of those things.
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Where then, and this is what we're gonna do next time we come hang out, we're gonna get into the firebox, right?
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And here is where we're gonna put all of these things in the appropriate quadrant based on you.
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So maybe your homework uh for today is continue writing those things down, get them out of your head, start looking at them, and then start thinking about like for real, for real.
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If nobody was gonna judge you, if nobody was gonna hate on you, if you weren't gonna disappoint people, like just say, I don't care, I'm like, I'm just gonna think about me.
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What do I want for me?
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Look at every single thing that you've written down, every single thing that was on your calendar, every single thing that wasn't on your calendar, and for every single one, think about do I care about this?
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Is this important to me, or am I doing it out of obligation?
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Is it important to me, or am I doing it because I yeah, I don't want to get written up at work?
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Like, and don't don't get me wrong, I'm not saying just stop doing everything.
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But like for real, for real, what you need to do is look at all of those things.
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Is it something that you love and care about?
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Those things, I'm I'm sure it's gonna be the smaller percentage that are on your calendar and the commitments that you've made outside of your calendar, are they things that bring you joy, that like amp your batteries up, that get you excited?
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If and and make a mark, right?
00:18:31.480 --> 00:18:33.480
Maybe, maybe here, let's keep it simple.
00:18:33.639 --> 00:18:35.240
Maybe go through the whole list, right?
00:18:35.319 --> 00:18:41.159
If you don't have the templates, which you can get, like I said, all you're gonna do is drop double D in the comments and you'll get the templates.
00:18:41.319 --> 00:18:54.519
But if you don't, and you're just writing it down for the things that like bring you joy, they bring you fulfillment, they like feel you charged up, that you look forward to and wish you could spend more time doing, draw a little damn happy face next to those, okay?
00:18:55.240 --> 00:18:57.079
And then go back through the list.
00:18:57.159 --> 00:19:00.359
And the things are like, meh, you know, whatever, I gotta do them.
00:19:00.439 --> 00:19:01.719
It's my job, it's whatever.
00:19:01.799 --> 00:19:03.399
I got a meeting, I gotta do the meeting.
00:19:03.559 --> 00:19:07.319
Maybe you do draw a little straight face, like little meh, whatever.
00:19:07.399 --> 00:19:09.879
Yeah, I don't love it, I don't hate it, it's whatever.
00:19:10.119 --> 00:19:20.759
And then for the things you're like, oh my god, I hate doing these things, I hate being in this meeting, I hate going to the grocery store, I hate XYZ, but you're still doing them, draw a little sad face next to them.
00:19:20.919 --> 00:19:33.639
I know this seems kind of kindergarten-y, but what it's going to do is it's gonna help you see, like, look at all of that stuff that you're putting all your energy, all the amazingness that you have for the world.
00:19:33.879 --> 00:19:43.480
How much of that is are you putting into things that aren't awesome, that aren't feeding you, that aren't contributing to your energy?
00:19:43.559 --> 00:19:45.319
Because that's some reality right there.
00:19:45.480 --> 00:19:46.599
So that's your homework.
00:19:46.839 --> 00:19:50.599
Now, I'm talking about a lot of things, and there's a bunch of videos, right?
00:19:50.679 --> 00:19:51.959
That you can go back and watch again.
00:19:52.039 --> 00:19:56.359
If you want to ask for the video, the link, I'll give it to you, or you can go to the YouTube channel.
00:19:56.439 --> 00:19:58.199
I know a bunch of you folks are already there.
00:19:58.279 --> 00:20:12.679
Uh, you can go through the playlist on selfish strategy, guilt-free future planning, daily domination, there's a lot of stuff, and you can take it all in and do the thing, and actually, I hope that you do because I want to help you make your days better.
00:20:13.079 --> 00:20:27.240
But if you want to like learn with a group of people and actually go through the entire system with other folks that are experiencing the same things that you're experiencing, maybe from a different degree.
00:20:27.399 --> 00:20:35.639
Um, my recommendation is you sign up for the next, I've got a batch of workshops coming up the self first framework.
00:20:35.799 --> 00:20:37.399
It's a four hour workshop.
00:20:37.719 --> 00:20:38.359
Hit the link.
00:20:38.519 --> 00:20:39.719
If you're interested, let me know.
00:20:39.799 --> 00:20:40.519
I'll hook you up.
00:20:40.599 --> 00:20:46.439
But I just kind of want to give you an overview of what that looks like because today, all we're talking about is strategically selfish schedule.
00:20:46.759 --> 00:20:47.159
Scheduling.
00:20:47.319 --> 00:20:52.439
But in the workshop, we do the future planning as it's like you're doing it in the room.
00:20:52.519 --> 00:20:53.879
You have access to the mirror board.
00:20:53.959 --> 00:20:57.399
We do the things, and I'm coaching everybody through it, having all kinds of fun.
00:20:57.559 --> 00:21:09.399
Then we get into strategically self-scheduling where you walk out with like clarity on what the hell you need to stop doing, how to stop doing it, how to outsource, how to opt optimize and automate things.
00:21:09.559 --> 00:21:24.599
And then we get down into daily execution, which again, it's a methodology for like getting stuff done and increasing our credibility, all for the purpose of building space into our calendar so we could build fulfillment into our lives, right?
00:21:24.759 --> 00:21:30.119
Or if you just want to like accelerate your career and beat the competition, this will help you with that too.
00:21:30.279 --> 00:21:31.719
I'm all about fulfillment.
00:21:31.799 --> 00:21:33.719
Um, so that's why I talk about that.
00:21:33.959 --> 00:21:40.759
Because you know, career success and all the other things for me are a byproduct of serving others and sharing my gifts and talents.
00:21:40.839 --> 00:21:42.359
So that's kind of the angle I come from.
00:21:42.519 --> 00:21:45.000
If you think that's BS, I understand.
00:21:45.079 --> 00:21:47.159
Um, you're not gonna hurt my feelings.
00:21:47.319 --> 00:22:01.559
Uh, anyways, point being sign up for the workshop, bring a friend because we'll be doing some learning, some application, and you will walk out with your own customized, personalized time management system, right?
00:22:01.799 --> 00:22:08.759
Or don't tell anybody, but it's not really a time management system, it is a self management system.
00:22:09.240 --> 00:22:14.439
Uh, and because when we start focusing on managing ourselves, guess what happens?
00:22:14.679 --> 00:22:20.679
We start really making progress because we take ownership for all of the things that are happening to us.
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