For the past 5 years, Jason and I have intentionally planned our entire year in advance. Yes, you read that right. The ENTIRE year! You may think that sounds insane, but it really does work for us. Some effort upfront and we reap the benefits all year long!
Tips for Planning Your Year in Advance
Of course, things can change in a year from now and you may need to adjust some events accordingly. That’s totally okay! But we are always surprised with how much we’re able to do on the day we originally scheduled. And even if it needs moved, it helps so much to have the event in the calendar and adjust from there.
Set Up a Digital Calendar
I love putting pen to paper and doing some of my planning that way, but when it comes to scheduling for a family and business, digital is best. We have used Google Calendar for years and years and it does not disappoint. It’s a real workhorse for our family and business.
If you’d like to calendar things for work, I highly, highly recommend having your work and personal on separate google calendars, each under their own gmail address. Even if you are a solopreneur with no one on your team (…yet) or you work for someone else, have your work calendar be seperate. Then if at any point you want to share that calendar with someone else (say a coworker or a future team member), you don’t have your personal schedule all mixed up in there.
Note: I’ve found that it’s best to use desktop to set up the calendars initially, but then we mostly use our phones after the initial setup.
Benefits to having a digital calendar
Google calendar is shareable and easy to access. All of our family and team can see events and any edits in real time. “It’s in the calendar” is a common phrase we hear at our house.
You can create multiple “calendars” under one email each with a separate main default color. This is the video tutorial I used to set up a different calendar for each kid.
You can quickly toggle on and off any calendars, according to what you need to see. We have a separate calendar for each of our kids under our main gmail address, each with a separate default color. Again, that initial setup is easiest to do on desktop, even adding custom colors.
Speaking of colors, I love the color-coding feature. When certain types of events are certain colors, it makes it quick to visually see and understand what’s going on for the week.
Creating recurring events. Things like birthdays, recurring weekly meetings, or weekly date nights are easy to just set on repeat. Don’t worry, you can edit or delete individual events when needed without effecting future events, so don’t be afraid to go for it!
Before diving into planning your year, first set up your google calendar. And once it’s set up, you won’t have to do it again!
Make a List of Categories to Plan for the Year
Get an overarching idea of things or categories you want to calendar. You can simply write a list or create a spreadsheet. It’s nice if it’s something you can refer back to next year.
I have a board I created in Monday.com (a project management software we also use in our business) that I refer to each year. It’s so nice! Each year, I feel like we get faster as we set things like this in place.
But not to worry, a simple spreadsheet will work just fine.
Once that category of events is in the calendar, you’re done! Move on to the next category. Remember, you can adjust events if needed down the road when you know more details. But getting it in the calendar will help so much. And if you’re anything like us, you’ll be surprised how little has to change because you just plan around it.
As you can see from the screenshot of our Monday.com board, let me explain some of the things we like to plan.
This is an easy one for us. We basically just plan when we will have each of our kid’s requested birthday dinner followed by presents, cake and ice cream. We are known for moving birthdays around to whatever day happens to be convenient for us. Who cares if it’s on the actual day or not? The main thing is that we celebrate.
But for the actual date, we have all our kids’ and our parents’ birthdays as repeated all day events on our calendar. We have their birth year in the event name (specifically helpful remember what birthday it is for our parents).
This is where Jason really shines! We like to plan one bigger family trip each year and he’s so good at figuring out the itinerary, cost estimates, and reservations needed or flights booked. It feels so good to get a head start on those things!
We pull up all our kids’ school calendars and get them in our calendar. First day of school, days off, end of term, etc. We love having all these things solidly in the calendar.
Holidays and Traditions
We have some traditions we love that we do around the same time each year.
Around Valentines day, we make 100 or so bags of fancy popcorn and deliver them to neighbors. We do this instead of neighbor gifts at Christmas time when they’re already loaded with treats and gifts…and I’m overloaded with trying to prepare for Christmas with 8 kids.
The week leading up to St Patricks day, the kids earn tickets by doing extra chores. Then on or near St Patricks day we make a concession stand of sorts in our house that we fill with goodies. The kids use their tickets to buy from the concession stand and we watch a family movie. It’s one of the few times a year we’re willing to pay to rent a new movie the kids want to see.
None of these things would really happen if we didn’t plan ahead to make it happen. It would just be a fun idea we never really execute on.
We look at the long weekends and plan a few to do some simple thing with our kids. For example, one year we tied a blanket as a family on a Monday we had off of school. There’s no way we would have done that without planning it in advance.
Don’t feel like every long weekend or day off of school you need to do something special. Heavens no! A day to do nothing is glorious as well.
We like a mix of simple fun and of…nothing.
We love to plan our anniversary. Generally we just plan where we will go and when.
During our planning retreat for 2023, we searched through Airbnbs and booked a one-night stay for our anniversary that was 9 months down the road. We were excited! We put it in the calendar and then basically forgot about it.
When our anniversary rolled around, it was like the excitement all came back again. We were busy getting the kids ready to start a new school year and there’s no way we would have planned the trip at that point. But guess what?? It was already planned! It ended up being one of the most fun anniversaries we’ve ever had. We both loved it so much!
Check out the beautiful airbnb we stayed at here.
It seems like every year we need to reevaluate and reinstate our date nights. It’s a good refresh for us.
This year, we put it in for Friday nights from 6-8pm, with every week of the month being a certain kind of date. One week will be a group date where we invite 2 or 3 other couples to join us (tomorrow we are having two couples over for waffles and game night at our place). One date a month that I plan, one that Jason plans, and one where we go to the temple together (a quiet place of worship for members of the Church of Jesus Christ of Latter-Day Saints). I’m super pumped!
We calendar in Sunday services, special conferences, and other church events.
Plan a retreat or distraction-free chunks of time to plan
For the past 5 years, Jason and I have done a “planning retreat” in order to be able to pound this out. Plus, it’s fun for us! We typically schedule an Airbnb somewhere close to home to keep it simple. Many times, we’ve been within 30 minutes of home. But the separate space and dedicated time are a huge benefit.
The place doesn’t need to be fancy. Typically the only extra feature we look for in a place is a table or desk big enough to spread our supplies out on and that has plenty of light.
But you don’t have to make it an all-day event like we do. We have 8 kids living at home and a business that runs out of our home, so we found stepping away is very helpful. Alternatively, you can plan some chunks of time to work on it. It will take a few separate dedicated time chunks, but believe me, it’s worth it! You could even rent a room in a library, go to a quiet restaurant, or be at a park if the weather is nice.
Our planning retreats are usually 2-night stays, giving us one full, uninterrupted day to plan. One year by the end of our retreat, we were overworked and upset with each other. Although we had gotten a lot done, nothing is worth that. That year we had tried to do too much in one day.
We learned we NEED to take lots of breaks and have plenty of snacks (including some healthy ones to keep you fueled and satisfied)! We’ve learned that generally, Jason and I need to have rejuvenating breaks for lunch and dinner at the very least. And for my sake, to keep any meal prepping to a minimum.
Don’t just say, “We’ll heat up leftovers for lunch so we can keep on planning while we eat.” Take a flippin’ break and have a great time doing it! I promise you’ll get more done overall during your retreat because you won’t get burned out. Plus it makes it so fun!
Walks are great. Games are fun. Or you can get even more creative if you’d like. Just keep it rejuvenating and fun.
This Year’s Planning Retreat
This year, we were in the town of Kanosh Utah for our retreat. We own a little house there that we’re trying to sell, so we figured why not? It’s a town of 500 people. There’s no restaurants or fast food options and definitely no theatre or any “entertainment”. And it was still so fun!
One afternoon, we walked to the tiny grocery store and explored their “bargain basement” full of random second-hand items. They sell delicious hamburgers, so we had that for lunch. We had fun buying some food we could piece together for other meals to supplement the food we brought from home.
Another evening we went to my brother’s house next door and actually played video games together with him and his wife. Jason and I hadn’t played video games for years. We laughed a lot and had a great time.
Another night, we had some fun snacks our trainer Madie sent with us as a special gift for our retreat, and we watched an episode of one of our favorite shows: “James Harriott.”
It can be any time of year
Don’t be held back from planning your year if it’s not January. Who says it needs to be in January?? Strike the iron while it’s hot and just plan a year out from whatever time it is now. Maybe you’ll find you love planning out your year every fall. Who knows?
I have one friend who loves to make goals for the year in the springtime. That’s when she feels the most rejuvenated and ready for a fresh start. I love that idea! And remember, you can always change it down the road and adjust as you figure out what works best for you and your family.
Give it a try! It works amazingly well.