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Be your truest self for a day or weekend.

Or give that gift to someone else.

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Ever feel like your job takes up too much of your headspace?


Identify as a parent or caregiver and forget who you are at your core?


Ever been on the cusp of something new – parenthood, the next chapter in your love life or career, empty-nesting, retirement?


Been searching for something that lights you up in your soul?


We see you. And we give you permission to be you.

“You are really on to something with this business! We had such a great time and probably wouldn't have taken the time to venture out that way. It was so nice to have the whole day planned. I've been telling all my friends.”

Mary, who went on a Day of YOU in Chicago with her friend Shivani

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Our Why:

You or someone you know needs a spark.

I started On Leave to give you permission to be your truest self and help you re-think what self-care means for you. On Leave is your go-to partner for designing a day or weekend that truly rejuvenates your soul.

The locations On Leave selects for you aren’t spas, poolside resorts or yoga retreat centers. They’re cities and towns in the U.S. where you can experience what you might not have known you needed – be that tarot card readings, cake-making classes, art walks, unconventional tours, magic hour hikes – so you can tap into your best self and shift your perspective, too.

“Kelly and I had such a fun time during our On Leave day. It was so nice to just have it planned for us. We were able to enjoy each other's company for our anniversary while trying new things in our own city, and we are both so grateful for these memories. We loved this idea as a gift for someone as well! We prefer memories over material gifts anyways!”

Jaclyn, who was gifted a Day of YOU along with her partner Kelly

“I am looking forward to doing more of these types of gifts, so be on the lookout! You have such a gift for this."

Bobbi, who gifted the Day of YOU to her neighbors Jaclyn and Kelly for watching her puppy, Kai

What really lights you up in your soul?

If you’re not sure what your ideal self-care day or weekend might be if it doesn’t involve a spa, pool or yoga, we can help – even before you do a discovery call with On Leave.

This 7-question quiz will help you start to think about the self-care style that speaks to your soul.

Is your self-care style Wander, Create or Learn?

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Customize Your Leave

You do so much for everyone else. Let On Leave get to know you and design the bespoke self-care experiences you need.

Invest:
  • A day

  • A weekend

  • A Monday through Wednesday, if that’s what works best for you!

Spend it:
  • By yourself

  • With a buddy or buddies of your choice

  • Or gift it to someone else!

“I'm so busy that it would seem counterintuitive to add something else to my schedule – but this day was perfectly curated for me and I didn't need to do any work to make it happen. Afterwards, I felt less overwhelmed. And I found new activities I enjoy. Now that I've dipped my toes in the water, I want to do this again!

Meredith, who got “Create” on our self-care quiz and went on a Day of YOU in Boston

Your conversations with

On Leave will focus on YOU.

We'll talk about your goals and what you want to feel.

Here is how solo and buddy travelers and staycationers work with On Leave:

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Talk about yourself in a discovery call.

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Receive a curated day or weekend plan, with all bookings made for you.

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Go On Leave.

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Unpack your experiences in a post-trip call.

Optional – but highly encouraged!

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