NEW: Organized Living is available for pre-order now: CLICK HERE

How to Plan Your Dream Day

Share this post:

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.

plan your dream day

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!

Leave a Reply

Your email address will not be published. Required fields are marked *

12 comments on “How to Plan Your Dream Day

  1. THIS. IS. GENIUS. Just thinking about it, makes one reassess and look to implement little changes, to include some things more and exclude others. And, plan for that Dream Day to actually happen. Thank you Shira, you always bring good things into our lives.

  2. “A goal without a plan is just a wish.”

    I needed to read this whole post today, but this quote really got me. Thank you, Shira!

  3. Its a ways out but I always take my granddaughter school cloths shopping. This last year was a first ,we drove to St George Utah took in a spur of the moment play at out door theater then drove to Vegas to shop for cloths. It was so amazing. I want to do again. This year I have marked off Aug 5th for a flight with Granddaughter to Calif my Sis (who is a great shopper) will go with and we will shop. overnite with sis in her new home in Northern Calif
    Note- my granddaughter’s Mom goes to she is so much fun and like a daughter.

  4. I am having my dream day today at the Florida beach with my husband and a stack of books I have been wanting to read. We are taking this week off to rest and pray and read and see what we want to accomplish for 2022!

  5. This is hard for me because I’m a mom of 5! I have younger (youngest is 16 months, 5 yo, and 7 yo) kids and older kids so I have built in babysitters (15 and 18 yo but their gone a lot) and my husband works really long hours and it’s hard to get date night or a night by myself somewhere or anywhere.
    We are trying the one car thing for being more green (less gas, maintenance, emissions and all that other stuff) and our public transit isn’t that great (horrible).
    I usually have our car on the weekend but we are doing family stuff. Uggghh this is harder then I thought!!
    My dream right now is to just go to the bathroom by myself uninterrupted! I don’t know what it is about little people but everything becomes urgent once I enter that room, or it’s time for bed.
    A spa day where my husband and/or older kids take my kids out of the house and I have my bathroom all to myself for 2-3 hours and do my homemade lotions and potions and soak in a bath and read!
    I’d love to go to to a real spa but because, well the pandemic, I’m not. Anyways I don’t know why I felt you needed a back story 🤷🏻‍♀️. Maybe because I have 5 kids you now know how badly I need this dream bathroom spa day! Lol!!
    This is a little off topic but what are your favorite “sustainable” or “green” or non bad chemicals beauty products and bath products? Would love a post!
    Have a great day!

  6. What a fantastic blog post this is! Great idea, Shira! I have too many dream days ideas, which is what prevents me from doing anything at all….so this will help me clarify! Thank you! Xoxo

  7. YES! I just had a disappointing birthday, full of running kids around my dr. husband worked late and I had to make dinner and (sigh) ate a piece of chocolate in lieu of a cake! I’m so happy you posted this–I’m resolved to plan my dream birthday for next year, a full day off for skiing with friends and a HUGE chocolate cake with candles!

Get on the List

Fewer, better emails. Sign up below for tips, resources, and inspiration, plus personal tidbits from my home and life.

Victory! You're in. It's all happening. Stay tuned for fewer, better tips, resources, and inspiration delivered straight to your inbox.
x Shira
Join the Community
Photo of Organized Dresser Top.