Leslie and Genny working at Stae Cafe in Markham

Work dates with my sispreneur

If you follow me on Instagram, you may have noticed that I go on work dates with the owner of Bee Clean Boutique once a month. Yes, she’s my sister in real life! And we’ve been doing these work dates for a whole year now—missing only the month of December because that was peak season for both of us. It’s been such a great experience that I want to tell you a bit about it and maybe it will inspire you to find your own work buddy or tribe to do monthly work dates with.

There were 2 reasons we started this. As entrepreneurs who are still too small to hire help, and therefore managing very full plates all the time, we found it difficult to make time for friends and family, and in our case, for each other. But we are both business owners – how cool is that, and wouldn’t it be fun to work together and exchange ideas, all while spending time together in person?

The second reason was that, admittedly, planning and creating content was frequently something that was easily put off because there was always something else that seemingly required our attention first. We recognized the need to dedicate a full day focused on content, and I’ve stuck to this purpose on all 11 of our past work sessions.

So, now you know what motivated us to do these work dates. Now, let me tell you more about them.

  • Organizing these work dates – We take turns on a monthly basis planning our work dates. The person responsible is in charge of selecting locations for working, for meals, and for one fun activity. The organizer is also responsible for expenses of the day up to $100, at which point we start paying for ourselves.
  • Locations – We love to explore new places and support local businesses in and north of the GTA. We usually start at a coffee shop where we can have brunch and work for an hour or two. We then go to a second location for more caffeine and quiet work time, and stay for 3-4 hours. Sometimes, there is a third location that may or may not involve food. After a productive day, we reward ourselves with a fun activity.
  • Fun activity – This is such an important part of the day. Not only is it motivating and rewarding, it also allows us the chance to treat ourselves to fun experiences, which can be a rare thing for busy moms to do. Some examples of things we’ve done are spa treatments, nature walks, and dining experiences.

You might be wondering how productive we actually are because it sounds like a lot bouncing from place to place. Actually, our brain needs breaks between focused work periods, and when we are not surrounded by chores around the house waiting to be done or children who constantly need our attention, then work is our priority and it gets done!

Before I end, I want to tell you about our very first work session, which was more than a day. We rented an Airbnb in Collingwood for a couple of nights and used that location to do a lot of photography and took advantage of the time to do a ton of planning. For fun, we explored the town and stayed up late at nights talking and watching TV. Heck, the whole weekend was fun! Anyway, my point is, it doesn’t have to be a single day meet-ups.

If you have any worksite or activity recommendations in the GTA and surrounding areas, please leave a comment. Like I said, we’re always looking for something new to do.

Leslie sitting on a hammock working Working in background with veggie platter in forefront Planner, phone, coffee and sunglasses on a marble table
Leslie and Genny at Bob Marley installation
Leslie working at coffee shop
Sitting in Toronto hotel lobby


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