Focus On This Podcast

92. 5 Steps to Planning Your Dream Vacation



Have you ever returned to work after some time off and felt like you needed a vacation from your vacation? Maybe you were checking your phone and emails so often that you brought the office with you. Or you spent too much time doing and not enough time resting. Is there a way to go on vacation and return rejuvenated rather than just as tired as when you started?

In this episode, Courtney, Verbs, and Blake talk about how to set up your time away from work to get the rest you need. They share 5 steps for planning the fully unplugged vacation of your dreams, so you can leave with confidence and return refreshed and ready to jump back in.

In this episode, you’ll discover—

  • How casting a vision for what you want turns hopes into actual plans
  • A step-by-step plan for equipping your team to cover your bases
  • Why it’s necessary to define “emergencies” before you leave
  • The value of blocking off time to tie up loose ends and get to inbox 0


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Episode Transcript

Verbs: Welcome to another episode of Focus on This, the most productive podcast on the Internet, so you can banish distractions, get the right stuff done, and finally start loving Mondays. I’m Verbs, here with Courtney Baker and Blake Stratton. Happy Monday to you both.

Courtney: Yes. Happy Monday.

Blake: Happy Monday indeed. I am ready for a vacation. It is officially June, and I sorely need some rest. I need some rejuvenation or…wait for it…re-June-venation. See that? Do you see what I’ve done? Do you see how witty and clever I am? Oh my gosh. Someone just had to pull over in their car. They groaned. They have a stomachache after listening to me say that.

This is a theme this month of rest and rejuvenation. The reason we’re focusing on rejuvenation on a productivity podcast is because if you don’t think of it intentionally… I would even go so far as to say if you don’t actually plan intentionally your rest and rejuvenation, you’ll be like me, where you go on a vacation that really just feels like a long trip. You get back as tired as you left, and you feel the need for rejuvenation still. We want to help you avoid that when we talk about today’s topic: vacations.

Courtney: We have a free tool for you. Listen. Before I tell you what the free tool is, I need you to not judge it yet. Okay? Like, judgment free when I say what this free tool is, because your first instinct is going to be like, “This sounds like a terrible idea,” but it’s actually brilliant. It is our Vacation Optimizer. Again, I can kind of hear you in your cars right now, thinking, “I don’t need to optimize my vacation. That’s exactly what a vacation is.” You’re actually wrong, and we’re going to tell you why on this episode. You can go ahead and get that download at

Blake: It’s true. Hand up. I’m the guy who says, “You know what I don’t want to do on my vacation? Anything.” So, planning or doing homework for my vacation does not sound great, yet I’m also the guy who has come back from vacation feeling like, “I’m still ready to go on vacation, because I’m just as tired.” I’m maybe not as stressed, because I took my mind off of work, but I’m not rejuvenated, or as I would say this month, re-June-venated.

Courtney: That is so hard to say…re-June-venation.

Blake: We have a theme this month of rejuvenation, and to be honest, I think what I’ve learned most in what we’ve recorded so far on this stuff is that if you’re not intentional about rejuvenation and you assume rest is just turning an off switch or turning on reruns of The Office, you actually are doing yourselves a disservice.

Rejuvenation… It sounds backward. It is restful, but you kind of have to do some work. Not work, but intentional thought to get the rest you need. I’ve been the guy who comes back from vacation, and I’m like, “Oh no. Oh, dang it! I need a day off, or three days off, before I go back to work, because I’m not rejuvenated.”

Courtney: Well, what about this? I actually have a friend… I was talking about this a few weeks ago. To get ready to go on her vacation, she was working so much. I mean, so, so much. I asked her… I said, “I feel like by the time you get to your vacation it’s going to take you the whole vacation just to get back to baseline. You’re not even going to rest.” She was spending so much energy trying to get the things done to be gone for that week. I feel like a lot of people do that. It’s like, “I’m still going to work those hours. I’m just going to do it all before I leave on vacation.” Then vacation doesn’t serve any purpose, really.

Blake: So you told your friend… You looked at her, and you were like, “Listen, Megan Hyatt Miller. You need the Vacation Optimizer.”

Courtney: No. It was not Megan Hyatt Miller. It was a good friend who’s an executive in her company, leads the company. She has such a great heart. She was doing all of these things. I was like, “You really have to look at yourself for a little bit and figure out what you need so this vacation really does do what it needs to do, to rejuvenate you and refuel you.”

Verbs: I think even not just not getting enough rest, but you want to switch over to actually enjoy your time away from work. Like you said, if it takes a while for you to just get back to baseline, then you’re going to check back into work feeling like that vacation never actually happened, which is what we’re going to talk through today, because there is a right way to go into your vacation as you plan it. I think we have about five steps of planning your dream vacation. Guys, are you ready to get into it?

Courtney: Yeah, let’s do it.

Blake: Let’s do it.

Verbs: Let’s do it.

Courtney: Step one is name your why. This is important to establish. Why are you going on vacation? I mean, right now it probably feels obvious. You’re recovering from 2020. But it’s important to say why you’re going on this vacation and what’s at stake if you decide to cancel your vacation or if you let work creep into your vacation. Again, I talked about that Vacation Optimizer and made the joke that you may be like, “I’m not sure about optimizing.” If you want to have a vacation where work doesn’t creep into it, that tool is really going to help you out.

Blake: I think the hurdle with this step is assuming the why is completely understood. This goes not just for you personally, but if you’re going on vacation with friends or with family, I think it’s all the more important to get the why out there, to say, “Hey, actually…” I’m doing a family vacation, and I think for my parents, part of their why is “We want to spend time with our granddaughter who we don’t get to see that much,” and part of my why is I want to spend less time with my daughter a little bit and spend more time with my wife and get some childcare.

Courtney: We need to scratch that from the audio so she doesn’t grow up and hear this podcast.

Blake: No, I want to spend time… Obviously, I do, but the why, getting clear on that and communicating that… It may not be as obvious as it seems to you, especially if you’re traveling with others. A bonus for this is when you get clear on your why, it’ll start to spark a lot of positive feelings rather than feelings of guilt. You’ll have feelings of, “Oh, I’m excited about this. This is going to be fun. This is why we’re doing this,” rather than a sense of “I have to mitigate my vacation” or almost apologize to others for missing work, or that sort of thing. I think it really cues you up well.

Verbs: I think it also shapes the kind of vacation you want to have when you’re naming the why of the vacation. For example, a vacation that’s meant for relaxing and recharging might be less full of activities than one that’s meant for adventure and seeing the world.

So, just saying ahead of time, “This is the kind of vacation we want to have,” or better yet, “How do we want to feel at the end of this vacation?” helps shape everything else you plan into it or that you plan to do while you’re on vacation. Starting from there, defining that why, how you want to feel by the end of it, helps you say yes to some things and no to the things that won’t fit into that feeling you want to have at the end.

Courtney: That’s a great transition to the second step, which is cast your vision. After you’ve established your why, you need to know what you want from your vacation and design it around that. How do you want to rest? Who do you want to see? Where do you want to eat? What do you want to do? This is the fun part. I don’t know if you two are like this, but once I’ve gone on one vacation, I’m thinking about the next vacation. You’re kind of in that mode of “Ooh. Maybe we could do this thing or that thing.”

My vision for vacations is a little dampened right now with an infant, but I’m going to live vicariously through y’all and get creative on ways I could do this. I think those questions help paint a picture of the hopes you have so you can turn hopes into actual plans. It gets back to what we’re all about on this podcast: what gets scheduled gets done. Honestly, that applies for your vacation too.

Blake: They say the most fun part of vacation tends to be before you even take the vacation. Have you guys ever heard that? Or it’s some version of that, where it’s like part of the fun is just the anticipation you feel. Especially if you’re really busy. I’ve had vacations before where, all of a sudden, I’m on the plane, and I think, “How did I get here?” because it was kind of a whirlwind getting everything packed and booking the Uber to the airport. “Okay. Let’s get everyone checked in.” And we’re on the airplane, and it’s like, “Oh yeah. We’re taking vacation. Cool.”

Casting vision allows you to feel the feelings you want to feel ahead of time. When you think through, “Oh yeah. Where do we want to go? What do we want to do? What would that be like? Oh, that looks so amazing. I love how this hotel has this. Let’s stay there,” that sort of thing, you actually can reap some positive benefits… Your vacation can start benefiting you before you even get in the car or on the plane.

Verbs: I think what also is important here… Blake, you just mentioned how much of a hustle and bustle it can be just to get to the airport to get on the plane. Even as you’re casting your vision and designing this moment, factoring in the realities of the moment that it’s going to take you to get there…

For instance, if you are traveling with little ones and you have an early flight, you know it’s going to take a lot to get them to where they might need to be and prep them for everything. Definitely take into account the getting to the actual vacation point where it begins. That way it’s not blindsiding you and you’re like, “Man! I’m already drained, and we’re not even to the airport yet.”

Just factoring those things in so you’re prepared mentally… Again, if you’re traveling with little ones, especially in an airport situation, you can prepare them, or even if you’re just driving somewhere. That way you’re not all the way zapped before the vacation even officially starts. To us that has been helpful.

Courtney: Verbs, I feel like you should get a gold star for assist in this episode, because once again, a great transition to our next step, which is cover your bases. In order to get the full benefit of your vacation, you need to do something hard, and that is unplug. No checking email. No checking Slack. No taking work calls. Obviously, there are emergencies, but you want to do all that work ahead of time so you can be prepared to be on vacation. You need to have that confidence that “Hey, while I’m gone, everything is going to get done.”

The first step to do that, to cover your bases and make sure you’re ready to go so you don’t have that stress, that overwhelm going into vacation… The first thing you can do is just make a list of everything that needs to happen in your absence. Again, the Vacation Optimizer tool walks you through this step-by-step, and, again, that’s at Then, once you have made that list, it’s going to be really easy to determine what needs to happen for each task. Is it something you can defer until you return? Is it something you need to delegate? Or is it something (my favorite) you just need to eliminate entirely?

Verbs: I have a question for you both on this whole “cover your bases” step. How far ahead of time…? Say, for instance, Courtney, I know you were out of the office on parental leave. How far ahead of time do you start thinking about this to stay out of that stressful time of having to think about it two weeks before? What’s a good amount of time to put our minds on it?

Courtney: That’s such a great question. Obviously, I was out for 12 weeks. I mean, if you’re going out on vacation for 12 weeks, that’s awesome. Good on you.

Blake: You got to have a 12-week vacation. You just kicked your feet up. No hard work.

Verbs: Produced a human. Kicked your feet up.

Blake: Must be nice.

Courtney: I’m not even going to respond to that.

Blake: Oh, did you hear that? That was the unsubscribes. There they go. One-star reviews.

Courtney: For me, when I was going to be on leave, I started working on this three months in advance pretty seriously. Honestly, we have a tool we use for parental leave that is a more robust version of this Vacation Optimizer tool. I needed to make sure everything was covered, and some of those were really big things that needed a lot of hand-off. I wanted to make sure there was enough runway to do that hand-off well. That included having some of my directors involved in certain types of meetings.

I left enough room for me to remember things, maybe things that only come up once a quarter. I wanted to be like, “Oh, you know what? That’s something that’s going to happen while I’m out. I need to make sure I have that covered.” I started that process really early. We’ve talked about this in other episodes. It was also great to have other people on my team step up to the next level because I was going to be out. That can happen, as well, when you are out on vacation. You can equip some other people to take on some tasks that maybe they wouldn’t get to do on a regular basis.

Verbs: Step four is communicate with stakeholders.

Blake: This is anyone who’s going to be impacted by your absence. That’s a stakeholder, people who need to know what to do and what’s going on when you’re gone…your colleagues, your team, your clients…anyone who’s going to be affected by your absence. This is a great opportunity, when you’re communicating with stakeholders, along with step three, to really up your game in terms of the systems and the communication systems that maybe are things you’ve had to work on for a while. The vacation and the impending flight or trip date, or whatever… You can leverage that to improve your communication overall and your system of communication with your stakeholders.

Verbs: I think that’s why I asked that question about how far in advance you are thinking about what needs to be communicated, what might need to be handed off, or who needs to be brought up to speed while you’re out, because depending on that time frame, it might be a good time for you to think about this and delegate, but then you have to also make sure the team you’re communicating to, or whoever it might be, is in a space where they can actually receive what you’re saying and know what to expect as well, because if it’s a week or two before you head out, chances are somebody is going to run into some conflict somewhere and you’ll get a call when you’re on the beach saying, “The office is on fire.”

Blake: You bring up a good point. There are some emergencies that maybe you would want to be in the loop about even if you’re on vacation, but it’s not good enough just to say, “Hey, call me if you need anything.” Right? Courtney, how did that work? Did you ever get “The building is on fire” type of phone call when you were on leave?

Courtney: No. I didn’t. Actually, there were a couple of things I knew would be happening, like closing out 2020, that I really wanted to know information, like, “Hey, how did this go?” It was interesting trying to pull responses. Most of the time people would be like, “Courtney, no. Just enjoy…” Because they knew, like, give me… It’s like that “If you give a mouse a cookie” concept, that I would want to know more. I would have more questions. “What about this? Did this happen?” So, they would be very vague, like, “It’s good. Okay. Go back.”

Verbs: Thumbs up.

Courtney: “Enjoy your time.” Yeah.

Verbs: I’m actually right in the middle of this. I think we’ve mentioned this before on the show. Every three years that you’re on team here at Michael Hyatt & Company, you get a month-long paid sabbatical. Here we are in the month of June, and I’m in the process of making sure that as I prepare to go on sabbatical in July, everything is in place and those who I might be able to delegate to or need to come in on some of the things I would normally do get that proper communication.

But it does take going back through your own process, because you know what to do. You know what you’re doing or you know what it takes to get what you would normally do done because that process is in your head, but just going back through and recounting steps and the workflows of certain things or certain projects… It helps the other person you’re going to delegate to who might be stepping in while you’re gone. It really helps them grab the overall process of what needs to get done as well.

Blake: So, you’ve communicated with stakeholders, people who are in the loop. You have clarity. They have clarity about what’s going to happen when you’re gone or what would have to happen. You’re ready to move to step five, which is tie up loose ends. This is the big one: tying up loose ends.

I would say with this one, I’ve been guilty of not scheduling loose-end administration time before a trip. I’ve kind of learned whenever my flight is, whenever that day is, I have to block at least a full day… You may even find it valuable to block two or even three days, depending on your responsibilities and how integrated you are and dependent you are with your team.

I’m relatively independent in the work I do, so I block out about a day just to catch up on loose ends, last-minute communication, those open loops with prospects or clients of mine I need to communicate with. This step is the difference between an “Oh God! Did I forget something?” type of feeling on the flight and a feeling of “I’m so excited” and feeling rested and able to engage in vacation.

Verbs: How are you catching what these loose ends actually are? How are they showing themselves as something that’s like “Oh, I did forget about that”? Are we missing a step somewhere or is it just new thoughts that come up? How does that work for you?

Blake: That’s a great question.

Verbs: Thank you.

Blake: I wish I could answer that, but we’re out of time, Verbs, so let’s move on. No. The Weekly Preview has steps that help me with this step of tying up loose ends. I just take it out of a Weekly Preview context and kind of put it into hyperdrive when I’m getting ready to leave on vacation. Specifically, the list sweep part of your Weekly Preview, if you’re used to doing that… You want to engage in that type of activity before you go on vacation.

For me, I check all of my inboxes. Back in the day, you had a physical mailbox and maybe a physical inbox on your desk. Some of you maybe still have these, the paper stacker trays on your desk. Now everyone has a dozen or more inboxes, from email to your digital project management tool to your Full Focus Planner to those physical mailboxes and other requests that may be coming in through different software streams.

So, for me, I like to look at my calendar. I just look at everything and do a big list sweep, and inevitably, just like sweeping your house… “Oh, I did not realize there was that much crap on my floor.” That’s usually what happens when you do a list sweep of all of those inboxes. Then it’s just a matter of not necessarily executing those things, but taking time with each one of those items and deciding what’s necessary.

“Is this something I need to delegate while I’m gone? Is this something I could just put on pause and set a reminder when I come back? Is this something that is only going to take 30 seconds and I can just execute or could I delete this item altogether?” After doing that big sweep, I just process through that whole list, so I’m effectively at inbox zero. I’m not just talking about email, but I’m effectively at inbox zero of those loose-end, open-loop things when I leave for vacation.

Verbs: Maybe, if it’s your first time doing this, as you prepare to go on vacation… Blake mentioned two to three days, but it may take you a little bit longer during your first time just so that proper communication can happen and you have enough time to close the loop before you leave versus two days before and there’s an open loop because the communication hasn’t been landed yet, and then people are sending you texts when you’re out.

Courtney: This just gave me an idea. I’m going to do this today, because I haven’t done it. I have a vacation coming up in October, and I’m going to go ahead and block off those two days before I leave on my calendar so things can’t get scheduled, that they’re already allocated for this exact thing. I think what usually happens is a lot of meetings get hit those last few days before you’re going to be out, because you’re going to be out. So, I think going in and blocking that off might be a great tool to try.

Verbs: The good news is you don’t have to return from vacation feeling more tired than when you started. You can create the fully unplugged vacation of your dreams when you name your why, cast your vision, cover your bases, communicate with stakeholders, and tie up those loose ends. Courtney, Blake, any final thoughts for our Focus on This listeners?

Blake: I have a final thought, and this applies to everyone listening, but it’ll be especially useful if you already have a Full Focus Planner. In the Daily Rituals section of your Full Focus Planner, one of the ways we teach setting up rituals is to first ask the question, “How do I want to feel?” In other words, when I’m doing my workday, how do I want to feel when I start my work and what would be required to achieve that? That’s the starting point for creating a workday startup ritual.

When you’re on vacation, it can be tempting to just throw everything out the window. Obviously, when you’re trying to unplug from work, you want to unplug from work, but the temptation is “Well, as long as I just turn off, or whatever, then a good feeling vacation is just going to happen.” That’s not necessarily the case. By all means download our Vacation Optimizer. We’ll give you that link again before we sign off. That’ll be helpful.

But at least ask yourself the question, “How do I want to feel each day when I’m on vacation?” and think about adjusting your morning ritual. For me, when I pull out my planner…I’ll be honest…it kind of triggers a work mode, because I tend to work with my planner open, and I don’t like to use my planner on vacation, but you may want to use it, at the very least, to construct a modified morning ritual that will cue you up to the type of day and feeling you may want to have.

It doesn’t have to be big. It doesn’t have to be long. It could literally just be two items on there, but ask yourself, “How do I want to feel when I’m on vacation, and what would be required of my mornings?” Maybe it’s as simple as “I wake up. I’m going to take 10 minutes to do some journaling about things I’m thankful for, and then I’m going to take 10 minutes to talk to my spouse or my friend, or whoever, to sketch our day so no one is stressed out about plans the rest of the day and we can feel free to improvise.”

Maybe that’s a bonus final thought. If you’re hearing all this planner talk about your vacation and you’re like, “No. I just like to play it by ear and improvise…” The reason you’re doing all of these steps is so you can improvise without any stress.

Verbs: That’s good.

Blake: So, there’s a little bonus final thought about my final thought. Enjoy your vacation and be intentional, everybody.

Verbs: Thanks for joining us on Focus on This. This is the most productive podcast on the Internet. Don’t forget to download the Vacation Optimizer at We’ll be here next week with another great episode. Until then…

Courtney & Verbs: Stay focused!