How to Plan Your Dream Day

One day, many years ago, Jordan surprised me by driving me to the Oakland International Airport. I didn’t realize until he parked what was happening, but it ended up being one of the most delightful days of my life. We flew less than an hour to Los Angeles and spent the next 24 hours doing all of my favorite things. We walked around different neighborhoods. We got the spicy tuna on crispy rice that I can never find outside of LA. We ate ice cream in the sun. We had dinner with two of my best friends, Stacy and Jessica. I was even able to sneak in my favorite yoga class before we flew back home the next morning. It was so thoughtful of Jordan, and I was struck by how just one glorious day could make me feel completely refreshed, inspired, and creatively recharged for weeks.

The memory of that day has stuck with me for years, and one of my favorite things to ask other people is what their dream day would look like. It says a lot about what they value, and most of them are nothing like mine. Some people are interested in high intensity sports or hikes or physical challenges, while others just want to drink tea and do a massive puzzle in peace. The interesting thing is that most of the things people tell me are actually quite simple and attainable with a little planning and intentionality. So, here’s my invitation to you as we embark on a new year: Plan yourself your own dream day. Need a little support to get started? Here’s how:

Clarify What Your Dream Day Would Look Like

Would you stay home, go out, or travel somewhere new? What would you eat? What activities would you do? What would you wear? Would you enjoy your dream day alone or invite others? Brainstorm on a blank sheet of paper if it helps. Get as detailed as you possibly can.

Reality Check

Your dream day has to be rooted in your reality or else you won’t give it to yourself. We’re in the middle of a pandemic, and perhaps you’ve just had a baby, or broken your leg, or your resources are committed elsewhere – if your dream involves zipping off to Paris in a helicopter you may need to scale it back a little, but you can always find a way to get even just a taste of what you are craving. I loved the day Jordan planned because I was yearning for more travel, and I missed my friends since leaving Los Angeles. If a night away had not been possible, a day trip coupled with a long chat with my friends could have still have provided the boost I was looking for. In truth, a drive to explore a new town or a hike with a picnic and some good conversation could have also been great. Identify what you are wanting more of (solitude, connection, ease, nature, etc.) and then find something that fits that need that’s still within the realm of possibility given your circumstances.

Sort Out the Logistics

The French writer Antoine de Saint-Exupéry said, “A goal without a plan is just a wish.” So let’s turn that little daydream into reality, shall we? Don’t despair if you’re booked solid and you need to look months ahead, just find an empty day and block it off in your calendar. As someone who chronically overbooks myself I like to write “FULL DAY OFF” or “SHIRA KEEP OPEN!!” in a bold color. If you have kids or pets you’ll want to make sure to line up the coverage and support you’ll need for the day. If finances are tight, offer a babysitting swap to a friend so they can plan a day of their own. Once your day is claimed, it’s time for the fun part. Book that mini trip or spa appointment or workout class or leisurely date with your BFF. Map out the hike you want to take or the bread you want to make or buy seeds for the gardening you want to do. The more you prep and plan ahead of the time, the more you can kick back and enjoy your day when it comes.

Prioritize It & Enjoy!

And now for the fun part! When the big day arrives, do your best to minimize distractions so you can be fully present for it. Set up an OOO if it’s a work day, silence notifications on your phone – you get the picture. Self care is not selfish, it’s vital.

I hope you’ll take me up on this little challenge and share in the comments, or drop me an email, and let me know what you planned for your dream day. Happy dreaming – you deserve it!