3 Easy Ways to Intentionally Plan Your Summer

Longer days and warmer temps.

Students and teachers wrap up the last days of school. 

The smell of grilling fills the air each night.

Summer is here. 

And if you’re anything like me, it’s easy to let these precious months slip by far too quickly.

This year I invite you to join me in challenging the norm.

Let’s pause for a moment and think about how we want to experience our summer this year. 

Let’s intentionally design our summers to meet our ideal mix of joy, rest, and fun.

Sound good?


Then be sure to check out episode 97 of the I’m Busy Being Awesome podcast today.

Learn my simple, three-step process to design your perfect summer.

And start making the most of these precious days ahead.

You can listen to the episode below, or stream it on your favorite podcasting app here: 

Prefer to read? No problem! Keep scrolling for the entire podcast transcript.

Listen To The Podcast Here!

In This Episode, You Will Discover… 

  • How to plan your summer with intention
  • Three new ways to approach the planning process
  • How to put these tools into practice and take action today

Links From The Podcast

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Episode #97: 3 Easy Ways to Intentionally Plan Your Summer (Transcript)

This episode releases on May 31st, which is absolutely wild. How is tomorrow already June? This is insane. I’ve been thinking a lot about the summer months coming up. A lot of my clients have kids beginning summer vacation soon, or they’ve already started summer vacation. It is finally getting warm, actually, it’s downright hot. I think it’s supposed to be 90 degrees today in Boston and summer is in the air. 

I’ve had a couple of people ask me about doing a podcast episode on planning out their summers. How can we intentionally create our summers and plan out our summers so that we really enjoy the next three months ahead? And I thought, love this idea. Heck yes, let’s do it. Because let’s be real, who doesn’t want to plan an amazing summer? 

Now, if you are listening out of real-time and it’s not summer, let’s say it’s November that’s okay! You can absolutely apply this three-month approach to any season. So whatever time you’re listening this episode is for you. You can just swap out the examples of when I talk about going to the beach with making hot cocoa and rolling snowman or something like that.

3 Steps to Plan Your Ideal Summer

Okay. So today we are going to talk about how to plan out and make the most of your summer. Now, just as we talked about in the time budget episodes, a couple of episodes ago, it is so important to make space, to plan so that you actually have time in your calendar for the things you want to do. And we’re going to do the same thing for us for the summer months ahead. So I’m going to share with you three powerful steps to design your summer with intention so that you feel good about where the time is going. And you can use one of these steps. You can use all three of them. Choose the ones that resonate most with you, put them into practice, and start designing your summer months. 

Now, summer has always been pretty fluid for me. It tends to kind of slip by in a blink of an eye. And if I’m not careful about it, I just kind of stay business as usual. Now like I said, this has been my MO – my mode of operation – for so many summers. And I have zero excuses. I’ve always been in the education space, which means I technically have summers off from teaching. I mean, yes, I’m still researching and writing and prepping for the next school year, but my schedule is much more flexible. But nevertheless, because I’m a creature of habit. And for my fellow ADHD out there, cognitive flexibility, not my strongest executive functioning, I am not a super go with the flow change, the routine type of person. So it’s much easier for me to just keep working and doing what was familiar. 

And upon talking with my clients, I have heard the same thing from them. It’s so much easier to just stick with what we know, keep doing the same things business as usual. But the reality is that we often end up regretting this. When we look back on how we use our time, we look back and we feel disappointed because we’re thinking, “oh, I wasted my summer. I didn’t make the most of my time. I really wish I would’ve done things a little bit differently and we get stuck in regret. 

Feeling Regret

And I have something to say about regret. Unless you have a time machine, regret is not a very useful emotion to sit in because we can’t change the past. So we don’t want to sit there in regret, just feeling terrible. Instead, we want to learn from it. We want to grow from it. And we want to move forward. So what do you want to learn from those past experiences where maybe you regret how you used your time? What do you want to learn from that and how do you want to show up going forward? How do you want to design your summer this year? 

So let’s talk about how to do that. My first tip is to think about your future self. Now, I’ve talked about the future-self concept for the long-term a couple of different times on the podcast. But basically, the idea of thinking three to five years from now about who you are and what you’re doing and checking in with future you for a bit of a reality check, to get some advice from future you to figure out how you want to show up today. Well, it turns out that you can do the same thing with shorter-term planning.

Check-in With Your Future Self

You can check in with future-you three months from now, and you can ask her, how are you feeling at the end of these three months what’s going on for you? Are you feeling energized? Are you feeling well-rested or are you feeling connected? Maybe you’re feeling accomplished. How are you feeling at the end of these three months? 

And then check in and ask, what are you thinking about? What are you thinking to yourself that’s making you feel that way? Are you thinking, “oh my gosh, what an amazing summer!” And you’re feeling super energized. Or maybe you’re thinking “that downtime was so needed” and you’re feeling rested and calm and at peace. Maybe you’re thinking about how much you love the people in your life. And you’re feeling super connected. 

So ask yourself, how am I feeling at the end of these three months? What am I thinking about that’s making me feel that way? And then from there, check-in on the specifics. Where did you focus your attention? What did you do? How did you spend your time allowing yourself to go to that best case scenario? Why not? You have the opportunity to create that. 

What do you want in these three months? Did you go all-in on that new skill or learn that language that you’ve been meaning to learn? Did you spend as much time outside as possible because you’ve been cooped up indoors for so long? Or did you reconnect with really important people in your life whom you haven’t seen for a while? 

Now, when I did this process for myself, I found that I was feeling incredibly rested and connected and grateful, but I was also feeling really carefree as well. That’s how I was feeling when I checked in with my future self three months from now. One of my goals this summer is to shift from existing as a human, doing all of the time into a human being. How can I be? How can I be in the moment and enjoy the time now? And so I found myself, when I checked in with future Paula three months from now, really focusing on that. I kept asking myself, how can I be? How can I be with the people I love? How can I be and enjoy and rest and feel grateful for where I’m at right now. 

Identify Your Must-Do Activities

Okay. So that is step one, take some time to think ahead to your future self. How are they feeling? What are they thinking about? Why are they thinking that way? What do those three months look like generally? And once you’ve checked in with your future self and you know what you’re thinking and feeling, then it’s time to identify what your must-do activities actually are. Now, what does must-do actually mean? These are your non-negotiables. 

So what are you determined to make sure happens no matter what? Maybe you are determined to finish your book or visit your family, or run a marathon. Alternatively, what are the traditions that you always plan on happening every single summer? So maybe your kids always go to summer camp. That was one for me. I would go to summer camp for a month every summer from the time I was seven until I was 17. That was a non-negotiable for me. 

I’m also from Minnesota originally, and if you asked people what their weekend plans are, 50% of them (at least) would say, “oh, I’m just going up north.” And that always meant we’re going up to the cabin this weekend. That was tradition. My aunt and her family always go to Disney every summer, no matter what, that’s their non-negotiable. So think about your life and your traditions. What are the things that you do not want to skip?

Summer Non-Negotiables

Another area to consider are the activities that you already have planned. So maybe there are graduations or weddings or reunions. Maybe you also have fun habit-based type goals that you really want to make more consistent in your summer life. So maybe you want to go to the beach once a week on Fridays or walk every single morning that it’s not raining, Maybe you want to work outside on your deck more often, rather than always inside in the office. So what does the everyday look like? Do you have any habit-based goals or activities that you want to incorporate more often into the day-to-day?

I encourage you to really spend some time brainstorming what these different must do activities and routines look like for you in the next three months. Do a big thought download of all of the different ideas. And to help create a little bit of clarity and structure in this brainstorming, you can even divide it into categories. Maybe you have a category for family, for self, for friendships or relationships, and for work. And you have all of the must do things that you want to incorporate in each of those categories. 

Now be careful here. We are talking about must do. These are the non-negotiables. So don’t go into fantasy land here. It’s going to be really easy to tell yourself you want to do all of the things, all of the ideas, all of the goals. And then you’re going to start mapping them out on the calendar, which is the next step. And it’s not going to fit. So check in with yourself. Are you slipping into a fantasy land where you’re really planning for the next six summers instead of the next one summer? Be on to yourself.

Map It Out

Then, like I said, the next step is to go to your calendar. Once you have identified your non-negotiables. And once you’ve identified the things that you absolutely want to incorporate in your summer months, it’s time to start mapping them out. Do all of these activities fit? If you’re planning tons of travel, does it literally fit in the calendar? Are there enough days for traveling to and from the destination as well as the actual vacation time? If you have tons of habit-based goals or goals that you’re working toward, are they realistic or are you spreading yourself too thin? 

So check in again with your future self as you build out your calendar. Check in with her to see if you’re in alignment with what she says you’re feeling at the end of the summer. For example, if at the end of these three months, one of your goals is to feel well-rested, yet your calendar has tons of activities or projects every single week, is this in alignment? Are you setting your future self up for success to have the summer she truly wants?

Choose your summer theme

So the last tip I want to share with you is to choose your theme for the summer. And I’m going to explain what I mean first, and then I’ll talk about how that fits into planning out our summer. So you can do this in a lot of different ways. 

Now, I was thinking about this when I was in the car the other day. I heard a couple of different songs that basically took me right back to summer in high school. I’m always so amazed by how music can really transport you back to that time when you first heard that song. I mean, you know how every summer there’s usually one or two songs that play constantly on the airwaves? And when you hear them over and over, you start to align them with those summer months. 

Well, when I heard some of those songs on the radio from high school the other day, it took me right back to that carefree, fun, and freedom of a high school summer. And I was thinking, well, what if I intentionally chose some kind of summer theme for myself this year? It could be a song, but it could also be a word or a phrase, or a quote. 

Words, Phrases, Quotes, and Songs

What would I choose? What would I do for a summer theme this year? And that got me thinking about a past episode that I shared on the podcast about choosing your word of the year, where you choose intentionally one word to outline how you want to show up throughout the year. And this year for 2021, my word is joy. So I’m intentionally finding ways to weave joy into my everyday life.

As I thought about the summer, I knew I wanted to build on this concept of joy. And from that, I kept returning to the idea of play. How can I build more play into my life? And I thought of a quote from Emerson that I really like, which is: “it is a happy talent to know how to play.” 

Now, I personally love this quote because I know for me, it’s easy to lose this talent of play. All of a sudden things become so serious. And I think it’s easy for us to essentially forget about play and the lightheartedness of play. And so I decided that my theme for the summer is to develop my talent for play. So I encourage you to choose your word or phrase or song to encompass what you want your summer to look like. What might that be for you? Then once you’ve chosen your word or your phrase or your song, then you can put it into practice. 

So how do we do that? How do we use this phrase or this idea for our summer? Well, what you’re going to do is take that concept that you’ve chosen and use it to help you make decisions on your day-to-day activities. 

Rocks, Pebbles, and Sand

There’s this story about a university professor who wanted to make a point about the importance of prioritizing how we spend our time. So apparently the professor stood in front of the class with this empty jar and they first filled it with some really big rocks. And they asked the class, is this jar full? And the class all said, yeah, the jar is full; the rocks are all the way up to the top.

Then the professor took a box of pebbles and they added those into the jar and they kind of shook the jar around so that the pebbles could fall into all of the open cracks and all the spaces where the big rocks weren’t. And the professor then said, okay, now is the jar full? The class said, yeah, now it’s really full. Then the professor took some sand and added that to the jar. They filled all the spaces where the pebbles hadn’t filled so there’s sand all the way to the top of the jar. And then the professor asked again, is the jar full? And the class apparently laughed and said, yes. Now it’s full. 

And the message here is that the jar is your life. And the big rocks are the most important things. They are your non-negotiables. Then you have your pebbles. The pebbles are all of the other things that matter, but you have some flexibility with them. And then the sand is the little stuff. It’s the material possessions. It is the extra things that you do all day. It’s the scrolling on Instagram. It’s busywork. It is the everyday stuff that fills your time.

Now, if we reversed the order of the things we put in that jar and we put the sand in first, there wouldn’t be enough room for everything else. You wouldn’t have room for the rocks, your most important non-negotiables. You wouldn’t have room for the pebbles, those other things that matter to you. Instead, there’s only room for the sand. So by prioritizing your big rocks first, your most important things, you always have room for them. 

And I think about this with our summer plans. We’ve talked about the big rocks. We’ve talked about those non-negotiables that we want to include. And we’ve talked about the pebbles, the smaller activities and the smaller goals and the habits that you want to incorporate as well. And I like to think about our word or our theme or our phrase for the summer as a way to intentionally choose the sand that we’re pouring into the jar. How can ew use our theme to flavor the everyday activities and tasks? Are they in alignment with our theme? 

For example, would agreeing to this request or that activity help me develop my talent of play? If not, maybe I reconsider. So think about how you want your summer to unfold. What is your theme? And then use this theme to inform your everyday activities and your mindset as you approach these precious days ahead. 


All right, let’s do a quick recap. Whether you are planning your summer or you’re listening to this at some other time of the year, all is well. You can absolutely use these three concepts to intentionally plan and make the most of your next three months ahead. So I encourage you to start by checking in with your future self. How are you feeling at the end of these three months? What are you thinking about? Where did you focus your attention? What did you do? How did you spend your time? Get that advice from your future self. I am telling you they are so wise. 

Then think about your must-do activities. What are your non-negotiables or the traditions that happen every year? What are the additional adventures or goals or habits that you want to work toward? And what do you want to make sure happens this summer? THEN, do a reality check. Do these activities actually fit in the calendar? Are you planning for fantasy land or do you actually have enough time? If you’ve over-planned then it’s time to constrain. What is most important here? What is TRULY a non-negotiable and what can wait?

Then once you’ve done those two steps, it’s time to think about your theme of the summer. What can you use, whether it’s a word or a quote or a phrase or a song, to check in with yourself and ensure that you are indeed intentionally designing your days in a way that you want throughout the next three months?