Cross It Off Day

Check out Cross It Off Weekend for an extended, luxury version of Cross It Off Day

Do you have something on your To Do List that’s been there for far too long and is now a source of stress, guilt, or feeling like a failure?

Do you keep pushing back the “deadline” of a task or project?

Are you really good at finding things to work on that aren’t THE thing you actually need/want to be working on?

Have a hard time reaching completion? Are you constantly stopping and starting and hamster’ing in the hamster-wheel?

Do you enjoy working solo but amongst others whom are also working?

Or maybe you just want a day to self-indulge and read trashy magazines while curled up in armchair before you do a ginormous 1000-piece puzzle?

Are you ready to finally cross “it” off?

Wait, pay to do something I can do on my own, when I want, from my home? But why? This is why. You can do sit-ups whenever you want. Do you? That’s why we hire the trainer, pay for a gym membership. Sometimes you need more of a push.


Due to COVID, Cross It Off Day is only virtual until further notice.

All below dates are at the historic Colvin House Mansion in Edgewater at 5940 N. Sheridan Road. Free parking is available in the lot. Make sure you register for the correct date. Sign up for all four of the 2020 dates before our February one by becoming a Quarterly Cross It Off’er, get one day for free. 

If you’d like to track, remember, invite, or share via Facebook — 


Cross it Off Day is, without exaggeration, the best anxiety-relieving concept/tool/event that's come into my life. I've been attending for about a year, and knowing that I always have one coming up within the next few months gives me such peace of mind. All the little things (and sometimes not so little) that are important yet easily put off, can be relegated from 'I'll do it "later"' to "I'll do this at my next Cross it Off Day". There's a place for those things now. Saya, thank you for giving me the opportunity to write some very important letters, emails, streamline financial stuff, and meet some awesome people in the most incredible place (shout out to Angela & Colvin House)!
"What an inspiring day!  Thank you for creating the format and facilitating such a successful event.  I hope you'll do it again as I'd love to come back!"
"GAME CHANGER!!! I'm having the most productive and happiest Monday I've had in awhile."
"I admit, when I heard about this initially, I thought, 'Why would I pay to do something I can do on my own?' I get it now. I got done in 10 minutes today things that I couldn't get done in the past three months."
"You're a magical-fairy. Every event of yours that I attend, I leave feeling good and having been productive."

Focus. Feedback. Camaraderie. Distraction free. Progress. Feel good.

An entire day to get it done

Bring your unfinished projects, the guilt-ladened items glaring at you from the fridge post-it or that abandoned list of your 2017 2015 1999 goals. It’s much more fun (and effective) to work on your to-do list when everyone around you is also hunkering down.

You’re tired of your excuses. We are too. No more excuses.

But also.

Play. Self-care. Selfishness. Fun. Feel good.

An entire day to do whatever you want to do.

Bring that romance or YA novel you’ve been dying to read. Those trashy magazines eyeing you from the guilty pleasure drawer. The drawing or painting you keep promising you’ll get back to. The scarf you want to knit. The reconnecting with high school or college friends. The puzzle still in the box.

Maybe it’s a serious, business’y, adult task you want to tackle. Maybe it’s a YouTube tutorial on how to put makeup on.

The point is that you have a chunk of uninterrupted hours for you to do you.


  • Group kickoff
  • Individual work (including breaks and lunch)
  • Group wrap-up including your progress report and “So, now what?” discussion

Primary Goal

Remove the big, hairy task from your To Do List. OR have a day dedicated to all the things you love to do but don’t make the time for — reading for pleasure, art, scrapbooking, making mixes, legos, video games. Your passion projects, your side hustles, your Squeeeeee.

Secondary Goals

  • Get feedback and support on specific tasks/projects or big picture’ness
  • Meet other motivated individuals who may turn into friends, clients, collaborators
  • Utilize a space outside of your normal space
  • Set yourself up for future success


Saya has run a business since 2004, providing a variety of offerings rooted in helping individuals and groups find fulfillment. Applicable to Cross It Off Day, Saya is a productivity maven with solutions on everything from which app will fix your inbox to how to plan that vacation in record time at her fingertips and is the ultimate connector — people to people, people to opportunities, people to themselves, people to success.

What’s Included

  • A full day of access to the venue – a cozy and peaceful ambiance that’ll allow for individual focus and group camaraderie – if in person or to the Zoom Room if virtual
  • Other people just like you, looking to get it done
  • A facilitator there to do one thing: help you make quality progress
  • Resources to help you continue your productivity post-event

We’ll even take your cell phone and/or not give you the WiFi password if that’s what you need to finally:

  • Write those thank you notes
  • Update your website
  • Create a budget spreadsheet
  • Research & plan your next vacation
  • Study for the GMAT or PMP or…
  • Plan 12 weeks worth of meals
  • Organize your taxes
  • Digitize your receipts
  • Read a book
  • Collage
  • Take a nap (seriously, someone did this)
  • ??? …


Where does this take place?

Zoom if virtual. If in person, usually the Colvin House. But we also change up locations. If you have a spot you’d like to offer up, you can reach out to Saya. Needs are fairly basic: desks and chairs, quiet, wifi. Bonus if you’re accessible by CTA, have parking, have a kitchen area. Bonus bonus if it’s an inspiring and serene environment.

Who is this for?

Nice humans with a task that needs completion or whom simply want to have a “do whatever I want to do!” day.

Seriously? People come to just read a book?


What if I don’t have a task or project?

Really? Really? Nothing on your To Do List?! That’s impressive and we aspire. If this day appeals anyway, come. Read. Doodle. Lend support to others. Teach us how to not have a To Do List.

What if I don’t have a big or sexy project, like writing a book or dropping an album?

Size and sexiness doesn’t matter. Anything is welcome as long as it won’t disturb other people (no noise, no smells, no animals) and doesn’t take up too much room (think the size of a desk).

What if I want to work with other people?

Virtually, have at it! In person, as long as there is an enclosed space where you can talk without disturbing others, fantastic!

What should I bring?

Everything you need to work on your project (notebooks, pens, your laptop, files, box of receipts, etc) or to practice self-care. In-person: Headphones if you want to block out ambient noise; lunch/lunch money.

What if I can only come for part of the day?

That’s ok but you’ll be cheating yourself (and us — we want to experience the entire journey with you). We highly suggest making this (and yourself) a priority and blocking out the entire day.

What if I’m an introvert?

Introvert-friendly environment. Saya is a master facilitator and host who is an expert at making everyone feel welcome and at ease. 

Should I register now or later?

Instead of adding “register for that awesome event” to your To Do List, just go ahead and register now. Then you don’t have to worry about it later.

Can I get a refund?

There are no refunds. You may transfer your spot to someone else via your Eventbrite account.

Why are you doing this?

No matter how successful we are, how many TEDx talks we’ve given, what magazines we’ve been in, how “happy” we are, it’s a constant challenge to feel productive, balanced, and fulfilled. When we do accomplish something or cross something off the list though, oh my goodness what a feeling. We selfishly want more of that for ourselves. We lovingly want more of that for you. We also are head over heels with the vibe and infectiousness that manifests when you get a diverse group of nice humans together all working towards a goal and wanting one another to succeed.

Plus, what a gift to yourself to have a day where you can remove your adulting pants and have a guilt free marathon of doing whatever makes you Squeeeeee.

Lunch – where and what should I eat if it’s in-person?

Bring your lunch. Have lunch delivered. Go out to eat. Whatever you choose, we’d suggest stretching your legs and giving your brain some air. We’ll give you some suggestions, depending on our location.