An End of Year Planning Date

A few years ago, Bart and I started setting aside one of the days during Christmas break for goal setting and planning for the upcoming year.

This big planning session now become one of my favorite traditions and I look forward to it every year.

How we do our annual planning session

We get a babysitter or ask Bart’s mom to watch the girls and we spend about four hours going through the upcoming year so we’re both on the same page (this year may be a little tricker, but you could do it in the evening when your kids are in bed or turn on a movie for them and have at least an hour and a half).

Our first year, we went to a casual sandwich place that wasn’t busy and had lunch during our planning session. The next year, we found a quiet place on the mostly-deserted college campus nearby.

This year, we did it last Friday on our nanny’s last day before Christmas break. It was such a great way to finish up the work year and be ready to hit the ground running in January.

No matter where we have our planning meeting, we bring notepads for both of us, our laptops so we can quickly look things up, water bottles and some snacks (this year, we did sushi delivery which was extra fun).

We usually break our plan into a few categories and then divide up our time so we have some sort of schedule and don’t accidentally spend our entire time talking about one or two of the categories.

  • Yearly scheduling. We decide what trips we want to go on that year and schedule them into the calendar. Are we going somewhere for spring break? How many ski days are we shooting for? Do we want to go camping over the summer? When does school get out and when does it start again? Do we have any big birthdays coming up that we want to celebrate in a special way? Where are we spending Thanksgiving or Christmas? Having a big-picture vision for the year really helps us make sure we’re spending our time the way we want to and know how it’s all going to fit in.
  • Business goals. Since we run multiple businesses, this is a great time to refocus at the end of the year, talk about what went well and what didn’t go so well, what we want to accomplish in the year ahead, what the major areas we want to focus on in the coming year, and how we’ll measure those. We talk about each of our businesses one at a time, from start to finish.
  • Personal goals. Since we know in advance when this planning session will be, we both come prepared with some of our personal goals for the year so we can talk through them together and understand how the other person wants to spend the year and what they’re focusing on and how we can both work together to support those goals. We talk about through how we’re going to measure those goals and how we’re ranking them (is putting in a garden a HUGE goal for me or a “it would be nice” sort of goal?).

Afterward, we take all our notes and type them up so we have all our goals and plans in one place. We usually save them in Google Drive so we can access them from anywhere and often print out hard copies too so we can REMEMBER what we wanted to accomplish.

These planning sessions have been such a great addition to our holiday season – it’s so fun for us to have this dedicated time to talk through our hopes, dreams, and goals and go into the new year feeling like we know what we want from that year and that we’re working as a team to reach those goals.

Do you do some kind of planning session like this? I’d love to hear about it!


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Photos by Heather Mildenstein

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  1. I do a trip planning exercise in Google Sheets and map out where we want to go by month. It really helps to prioritize places we love, and to slot in new spots that might be better in a particular season. My husband’s not involved (not his wheelhouse or interest), but he appreciates that adventures are planned!

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