Why I Run My Relationship Like a Corporate Retreat
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Each week, I share real talk about building a life you actually enjoy—the wins, the fails, and everything I'm learning along the way.
This past weekend, my husband and I locked ourselves in our favorite local coffee shop for five hours straight.
Not a crisis meeting, I promise. We were doing our yearly couple's planning session. And believe it or not, it's one of my favorite things we do all year.
I know that sounds nerdy as hell… Most people think "romantic getaway" and picture a beach or a bottle of wine. Not spreadsheets and goal-setting. But here's why it's actually my favorite: This is where we get to dream big together, check in on what's actually working (and what's absolutely not), get wildly excited about plans that feel impossible, and make sure we're still rowing in the same direction.
If you've been around She Boss Life for a minute, you might've already snagged my free couple’s planning template. But I wanted to share the story of how this became our non-negotiable yearly ritual, because knowing the steps and actually doing it are two very different things.
Why our first planning session is still the most memorable
I first heard about couple's planning on a BiggerPockets podcast episode with Jay and Weendy Papasan. They talked about taking an annual retreat to plan their year together, and something about it just clicked. So we decided to try it for ourselves. We booked a long weekend in a nearby town, brought our laptops and notebooks, and dove in.
We had been casually throwing around the idea of buying a rental property for a couple of months before our first planning session. You know, the kind of goal that sounds great in theory but feels absolutely impossible when you think about actually doing it. But we figured, hey, we're doing this planning thing, might as well throw it on the list and see what happens.
As we mapped out our goals and started breaking down the actual steps to make this rental property happen, we realized... it was doable. Like, very doable. We weren't missing some magic ingredient or secret knowledge. We just needed a plan and the guts to start.
By later that summer, we had purchased our first rental home.
That was my first real "oh damn, there's something here" moment. This whole planning process wasn't just a cute couples activity. It was legitimately life-changing…
What we learned after years of doing this
We've been planning our year together every January since, and here's what actually works for us:
1. Get out of your house. Ideally, make a long weekend of it. Book an Airbnb, find a cabin, go somewhere that feels special. At minimum, post up at your favorite local coffee shop for the day. (With all the travel chaos happening in January this year, the coffee shop was our move. Still counts.) There's something about changing your environment that makes the big dreams feel more possible and the honest conversations flow easier.
2. Schedule quarterly check-ins. This is the part most people skip, and it's the part that makes the whole thing work. Things change. You schedule more than you bargained for and suddenly that trip to Portugal feels insane. Or you lose interest in that side hustle you were so excited about in January. The quarterly check-ins keep you aligned and give you permission to adjust without feeling like you "failed" at your plan.
3. Try something new each year. Every time we plan, I like to bring at least one new activity or framework that sounds interesting.
This year, I incorporated an exercise I read about in Die with Zero where you map out a life timeline with experiences you want to have at different ages, looking at it in 5-10 year increments. It only took us about 15 minutes, but man, it was insightful. Some trips I'd been mentally holding onto suddenly made way more sense for a "later in life" phase, so I got to release that mental energy. But that massive hike I've been thinking about? That needs to happen while my knees still work. So it's now officially scheduled for September.
Last year, I brought these conversation starter cards to one of our quarterly check-ins and they ended up sparking some surprisingly deep discussions about our future that we probably wouldn't have had otherwise.
You never know what new activity is going to unlock something about yourself or your partner. Stay curious.
4. Don't do this on January 1st. Let yourself recover from the holiday chaos first. Wait until you're ready to settle back into routines. Then use this planning time as your chance to actually guide what those new routines should look like for the year.
The real secret? Just start messy.
Look, your first couple's planning session probably won't be perfect. You might forget half the questions you meant to ask. Your partner might get distracted by their phone. You might realize halfway through that you have wildly different definitions of "financial goals."
That's all normal.
The point isn't to execute flawlessly. The point is to create space for the conversation in the first place.
Here's what I've learned after years of doing this: the couples who plan together don't just accomplish more…they fight less, feel more connected, and stop having those "wait, I thought we agreed on this?" moments.
So if you've been putting this off or waiting for the "perfect" time, this is your sign. Grab the free couple’s planning template, block off a few hours, and see what happens. Trust me, you won't regret carving out the time for this.
Here’s to a year you design instead of just survive,
- Kara
Short on time but want to absorb this while you're doing literally anything else? I made a Speechify audio version of this email. Listen here at 1.5x speed while you're folding laundry or walking the dog. You're welcome.
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About Me
Hi, I’m Kara. I’m a former workaholic turned time-management expert. I help women stressed out in their 9-5 get more done, in less time, so they can get back in the driver’s seat and start living a life they love.
