Earlier this year, I went on a personal journey to lower my stress after jaw surgery — an injury that traced back to long-standing stress. One of the changes we made at home was adding the Skylight Calendar to our routine. Like a lot of moms, I juggle a lot between work, family, and taking care of myself. And it felt like I was carrying the entire mental load just to keep everyone’s days straight — especially now that the girls are older and have plenty of their own things going on. The Skylight was my fix: something to keep us organized that wasn’t just my brain. (This isn’t sponsored, just my take on it!)
Here’s the honest version, though: six months in, I can tell you this is not a set-it-and-forget-it system. You have to keep it updated and tweak it to find what works. The first few weeks involve some trial and error. But once we found our rhythm, the Skylight became something we reach for every single day. Below, I’m breaking down exactly how we use each feature (and the lessons we learned) so you can skip some of the hurdles we went through.

The Calendar
The calendar is the easiest feature to set up with no subscription needed. We synced all of our individual calendars and color-coded them by person, so you can see exactly what everyone has going on at a glance. You can also adjust the color-coding manually. For example, if Chris is the one taking a girl to an appointment, he can add himself to the event, and it shows up in both of their colors.
What I love most is that it syncs both ways. If I edit an event on the Skylight, it automatically updates the source calendar (iCloud, Google, and so on). We sprung for the $79 year-long subscription to Calendar Plus, which unlocks several premium upgrades. For starters, with the subscription, you can forward an email to your device, and it will pull the event details into your calendar for you. The subscription has other benefits too, and I’ll get into those below.
Chores & Rewards
This is what we use the Skylight for most, and it’s had the biggest impact on our family. (Note: While setting up basic chore checklists is free, you do need the Calendar Plus subscription to unlock the actual star-based tracking and reward features.) I initially set it up so every star was worth a quarter, and I assigned stars to everything — routines, daily and weekly chores, even a “read for 30 minutes a day” task worth 10 stars.
The trouble was that some of those things the girls were going to do anyway, like brushing their teeth or getting dressed, so they’d forget to check them off. Then they’d go back and mark a week’s worth complete right when they wanted to cash in. Not exactly how the system is meant to work. And reading for 30 minutes isn’t something I can really fact-check, so it was easy to “remember” reading that hadn’t happened.
Here are the pivots that made it work for us:
- Understand the difference between chores and routines. A routine is something you do every day — brushing teeth, showering — and if you skip it, it resets the next day. A chore has a due date: if you’re assigned to unload the dishwasher on Monday and don’t, it rolls to Tuesday with a “one day late” reminder in red. For me, the deciding question is simply whether I want the task to roll over. If I do, it’s a chore.
- No more rewards for routines. At our girls’ ages, I don’t need to incentivize morning and evening routines — but the checklist is still helpful for keeping them on track.
- Vary the stars by effort. Each girl has daily tasks that keep the household running — usually quick resets like unloading the dishwasher or tidying a specific area. I assign more stars to the tasks that take more time or effort. I also created “up for grabs” tasks that aren’t assigned to anyone and can be claimed by whoever gets to them first. Those are worth the most stars, since they tend to be the bigger, harder jobs. They’ve become a surprisingly effective way to get things done without me assigning them.
- Switch to a tiered reward system. At first, every star was worth 25 cents, and the girls cashed out at $10. But managing those frequent cash-ins got tedious. So I built a system where the more stars you save before cashing in, the more each one is worth. It works almost like compound interest. It rewards them for waiting, which quietly teaches delayed gratification and real-world money management, and it’s far easier for me to manage.
Meal Planning
I’ll be honest, this is one area where we aren’t using the Skylight to its full potential yet. Chris is the cook in our family, and I’d love for him to start putting his meal plans on it. Every single morning over breakfast, the girls ask, “What’s for dinner?” Having it on the Skylight would save him from answering that three times a day.
Keep in mind that the entire Meal Planning section is exclusively within the paid subscription feature, but it’s been entirely worth it for our family. It includes advanced meal-planning tools: you can import recipes, and it builds a grocery list for you. With so many of Chris’s recipes already online, I think this could work beautifully for us. And if you’re not much of an inventive cook, you can even snap a photo of what’s in your fridge, and the subscription’s AI assistant will generate a recipe for you.
Lists
This is the feature I’ve most recently started playing with, and it’s a nice, flexible one. You can create any kind of list you want, whether that’s groceries, a weekend to-do, or a quick note you don’t want to forget. Standard text lists are free for anyone to use. But if you have the premium plan, you can even photograph a handwritten list and import it directly.
One of our team members uses lists to keep a running “wish list” for each of her kids. When they ask, “Can I have this?”, she has them add it to their Skylight wish list — and when birthdays roll around, she has a whole list of ideas to pull from, without trying to store any of it in her head until then.
Is the subscription service worth it?
When my sister recently got one, she asked me the question everyone wants answered: “Is the subscription really worth it?” My answer was an immediate yes. The rewards system alone earns its keep for us, and the AI assistant has been a genuinely handy bonus.
Is the Skylight Calendar worth it?
Ultimately, the Skylight has been a genuinely helpful tool for our family, and it’s one I’d recommend. It does take some work to learn and set up. This isn’t a plug-in-and-walk-away system — but once you find what works, it’s a wonderful way to lighten the mental load. For us, it’s cleared space in my head and gotten the girls contributing regularly to keeping our home running smoothly. That’s worth a lot.
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