Why We Turn Date Nights into Planning Meetings

It’s not always fun, but it is always worth it.

Justine Janssen
Hello, Writer.
5 min readMar 3, 2022

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Photo by taylor hernandez on Unsplash

If you’re already convinced that you want to start annual planning, I describe exactly how to do it (and share some of my past plans) here.

Why My Partner and I Started Planning

Eric and I met at an orientation event on the first day of university. I was seventeen — that was half my lifetime ago.

At the time, I thought I was going to become a rural family doctor and Eric thought he’d be an entrepreneur. We didn’t know it then, but we’d end up growing up together.

Over the years, we would change interests and add distance, demanding careers, and kids to the mix while figuring out how to grow together and stay on the same page.

Embarrassing photographic evidence of our first meeting in 2005. Babies.

“Life is a matter of choices, and every choice you make makes you.” — John C. Maxwell

Our choices can have massive impacts on the trajectories of our lives, but at seventeen, they felt like they only directly affected me.

In our early years together we supported each other, but still made our own decisions. This led to us managing a long-distance relationship after graduation. Eventually, we decided to stop long-distance and test building a life together in Toronto.

Six years after that first awkward meeting, we moved in together, only to realize we had grown differently and were not in synch at all. It felt like this wouldn’t work out.

We realized that, if we wanted to be together, we’d have to get on the same page.

We had to figure out what a life built together would look like — and if we’d love it or leave it.

And so, over a decade ago now, we began scheduling planning dates, which has evolved into a pretty solid process that we commit to each year.

Why We Make Planning a Priority Every Year

I will share off the top: planning isn’t fun.

I love the outcomes, and there are parts of the process I enjoy, but there’s a lot of it I don’t and you may not either.

Working on our 2014 plans.

What Makes it Tough

#1 It Takes Actual Work

You need to sit down and think and write and prep for it, then you need to make time to meet about it and work through it. For us, it typically takes two or three sessions of prep individually and then two or three sessions working on it together.

#2 It’s Uncomfortable

You have to be vulnerable about your desires and open to your partner having different ones. You’ll need to make compromises, and land on a plan that’s going to work for everyone, all within your family’s constraints.

In my experience, this can bring up a lot of emotions and resistance, and working through constraints can feel tense and uncomfortable.

Why it’s Totally Worth it

#1 To Live Life on Purpose

Manifesting is Insta-famous right now, and while I am not sure if having high vibe energy will magically make life happen for you, I am incredibly confident that taking time to articulate your dreams and values is a cornerstone in living an intentional life.

However, dreaming without any planning or execution, and expecting those dreams to come true, feels foolish — like hoping your way to a fit body.

Expressing your desires and working together on a plan to prioritize them, then scheduling them in to make sure they happen is magic.

Part of my 2015 dream list.

#2 To Stay Aligned

Our family has five and a half people — soon to be six people in it. The decisions that either of us make, especially when it comes to how we will use our time and energy, impact this whole crew.

If we don’t clearly communicate our intentions, the implications of decisions effectively get imposed on everyone else. This generates unnecessary confusion, tension and resentment.

In our experience, “fairness” in how family resources are deployed in a given year doesn’t matter as much as ensuring that we’ve discussed and agreed on our priorities.

Everyone needs to be aware of and aligned around what they’re signing up for.

Being up front about our desires and working through those gives and takes removes a ton of tension and keeps us on the same page. We leave the process clear on what we’re signing up for and energized about the year ahead.

We understand what our priorities are and how they impact our family.

Putting the 2022 plan on the calendar.

#3 To Level Up

Planning gives us a forum to challenge each other to consider options and opportunities we may have otherwise dismissed.

It gives us an opportunity to help each other grow.

The process also gives us a concrete plan to hold ourselves accountable to, by actually getting things on the calendar.

Planning helps us make better decisions and build a better life.

A photo of our kids that makes me feel grateful for the life we’re building.

Ready to build your own plan?

Here’s exactly how to do it.

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