Why you should consider a planning weekend every year

*cue the music*…it’s the most wonderful time of the year

I’m talking about planning weekend, of course. Which yes, in this household, counts as the most wonderful time of the year!

Checking in on our puppy Minnie before our flight to Greenville,SC!

What is planning weekend, you ask? It is…so many things for me and John Michael. I’ll take you through our planning weekend – what it is, why we do it, and how we do it – the whole 9 yards. Hopefully, you’re able to take away some ideas. Maybe you want to do your own planning weekend one day. Or maybe you just have a few hours to set aside. The first rule of planning weekend is that you focus the time you have on you.

The first three and a half years of my relationship with John Michael were long distance. We dated across continents and across oceans, sometimes a literal world away. So in our first year together, we went for an impromptu weekend trip and just talked about the year ahead. It was informal. I brought my planner along because #PlannerIsLife. We talked about our upcoming travel, where we wanted to go, and what we hoped to accomplish for next year. It was critical for the health of our relationship to be intentional about this. We’d go weeks – sometimes months – without seeing each other. Planning our next trip always gave us something to look forward to. Having a dedicated planning weekend didn’t just make my heart soar – it kept our relationship afloat.

And so was conceived our planning weekend. We’ve done it every year since. in the fall, typically in October or November, we leave home for a weekend away. We bring our planners now (I’ve since converted JM to an Erin Condren weekly). And we talk at a high level about next year. In years past we’ve done planning weekend in Madrid (I was living in Europe), Vermont, and Colorado. This year, we chose the location of our alma mater, Greenville, South Carolina.

Think of planning weekend as a strategy conversation about next year. You already have big ideas and big plans. This is your chance to get them on paper. For the big plans, you know what they are – the wedding of a loved one, the family reunion, the big trip with your friends. Things that you plan 6-9 months (or more) in advance that you already have on the docket. The big ideas, though? John Michael and I use planning weekend as a goal-setting retreat to share our big ideas with each other.

In Greenville this year, we stayed in a hotel downtown. Having a home based allowed us to break up planning and goal-setting with meals at our favorite restaurants and strolls down Main Street. John Michael played golf one morning and I caught up with a friend from school. Interspersed between the activities, however, we had a chance to sit down and sketch out our year.

Now, if you haven’t heard yet – we’re getting married in 2022! For obvious reasons, this date is looming large on our calendars. It’s quite literally the biggest event of our lives. I don’t know how you prepare for that. Understanding that, we’re intentionally thinking about how and where we spend our time and energy next year. We don’t want to metaphorically limp into our wedding, exhausted by overextending ourselves in the run-up to the big day. So John Michael and I put actual, physical boundaries in our planner: No traveling during the period around our wedding.

Your mileage may vary, of course. I’m not prescribing a system for you. But I am saying that it’s important to think out loud. What non-negotiable commitments do you already have for next year? Are they creating bottlenecks where you travel in multiple consecutive weeks? If you work and your work is cyclical, how does that factor in? How do you normally respond to the seasons? Do you need to escape the cold in February or March? This is your 30,000 foot view of the year. These are the questions we ask each other. It helps that John Michael is honest with me and has no qualms saying “Lauren, you’re overextending yourself. That trip doesn’t sound like a good idea if you’re trying to do it in April. Why not May instead?”

Planning doesn’t take that long. We pop a bottle of wine and play music – keep the mood light! This segues into talking about our goals for this year. Now, goal-setting is a personal process. You don’t have to do it as part of planning weekend. In past year’s we’ve used the Mäksēlife goal-setting system to set goals individually. This year was more informal. I’m a believer in setting a few goals you feel attuned to. John Michael and I reflected on our progress towards our individual goals this year. It’s all support, love, and gentle accountability. We’re not doing a post-mortem of why I tried and failed to complete a goal. Instead, we talk about what we learned and how we can better support each other as cheerleaders (& occasionally, coaches).

Inevitably, this transitions into goal-setting for next year. I share my individual goals with John Michael, he shares his with me. We ask each other a lot of questions – why that goal? Do you think this is realistic? How do you see your path to completing this goal taking shape considering everything we have going on? How will you respond to failure? The questions are pointed, but they really make you think critically about your goals. Nothing half-baked in our house! John Michael and I also discuss our goals as a couple. The identity we want to assume, the things we want to prioritize – it’s all out on the table.

Our planning summit culminates with the part I find the most touching and meaningful. John Michael and I set one goal for each other. We know each other’s strengths and weaknesses. We are each other’s accountability partner.

And oh yeah, after all that heavy thinking? We made sure to explore Greenville! Here are some of our top recommendations if you find yourself in the Upstate.

Greenville Recommendations

Sharing drinks at Juniper

  1. Jianna: This was an early date spot for me and John Michael. Its terraced seating overlooking Main Street, downtown Greenville, and famed Falls Park is my favorite seat in town to people watch and enjoy each other’s company. The fresh pasta doesn’t disappoint, either!

  2. Spill The Beans: If you don’t spring for dessert at Jianna, head across the road for a nightcap of ice cream at Spill The Beans. Mix in as many toppings as you can, I promise you won’t regret it.

  3. Juniper: John Michael and I moved away from Greenville before Juniper came to be, and it’s probably for the better. Otherwise, we would have spent all of our money here. It’s a chic and trendy rooftop bar with gin-focused cocktails. This isn’t a concept I expected to find outside of New York, but it works for Greenville. Ensconce yourself in a corner booth overlooking downtown and drink in the ample greenery overhead. You’re in a greenhouse, after all.

  4. Biscuit Head: A breakfast staple with roots in Asheville, NC, your visit isn’t complete to Greenville without trying a cat-head biscuit (so named because they’re bigger than a cat’s head) from Biscuit Head.

  5. Swamp Rabbit Cafe: The Swamp Rabbit Trail is the greenway that put Greenville on the map, or something like that. Hundreds of thousands of runners, bikers, walkers, and bladers traverse the paved trail from Downtown Greenville to Travelers Rest (& beyond). There’s no better spot to waylay yourself (on purpose) than the Swamp Rabbit Cafe. Their prime location is right off the trail. Get a coffee, a pastry, and watch families and fitness fanatics in equal numbers zip by on the trail.

  6. Tandem Creperie: So OK, my favorite meal is breakfast if you couldn’t tell. I admit it. Tandem is in Travelers Rest, a small town about 10 miles by the crow from downtown Greenville. Bike the Swamp Rabbit Trail to earn your breakfast. Get the Lumberjack crepe and a cappucino. Thank me later!

Supplies to bring

  1. Your planner

    1. Lauren’s planner: Erin Condren hourly LifePlanner

    2. John Michael’s planner: Erin Condren vertical softbound LifePlanner with a vegan leather cover

  2. Sticky notes: These are our absolute favorites! Use them as placeholders in your planner if you don’t feel like putting something on pen and paper.

  3. Pens and Highlighters: All those hopes and dreams have to go somewhere! Use your pens and highlighters to help you. (click here for favorite pens)

  4. Mäksēlife Companion Notebooks: I prefer the Mäksēlife system for goal-setting. If you don’t want to spring for the full planner, their companion notebook system is a wonderful complement to your main planner. If you use a different goal-setting system, or don’t have a goal-setting system at all, that’s OK too! The important thing is to think about your goals, no matter what system you use.

  5. Perpetual Calendar: Keep your important annual dates, events, anniversaries and birthdays handy for quick-reference when you plan ahead for next year. Grab yours here.

Questions to ask yourself

For us, this is a mix of reflection questions about the last year, as well as some forward-thinking questions about the next year. Your list can and should vary, of course.

  1. How do you feel like the last year was for you individually? How do you think it was for us as a couple?

  2. What were the most challenging periods in the last year?

  3. In an ideal world, what would your morning routine look like? Evening routine?

  4. Understanding that life gets in the way of “ideal”, what are the most important aspects of your routine?

  5. What are areas that you need help with?

  6. What are areas where I can best support you as my partner?

  7. What are some goals that we can work on together?

  8. How are we setting aside intentional time to be together?

  9. What are our individual restorative tasks? (e.g. working out, taking a nap, reading a book, meditating)

  10. What is one goal you have for me next year?

  11. What are our goals as a couple for next year?

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