I worked as a freelance magazine writer and editor when my kids were tiny. Then I took a long “break” from paid work. When I returned to my career five years later, the kids were 14, 11, and 8, and one of the first things I noticed was that there were a bunch of ceremonies and systems from my consulting life that could also help with the chaos at home.
We started having family meetings after Sunday dinners to talk about the upcoming week. I created Kanban boards for everything from house projects to Christmas lists. I even thought about creating a Slack workspace for the family. But the business concept that fascinated me the most was the annual retreat.
The concept of stepping away from the grind, of creating space and focus to do some serious strategic thinking was fascinating — and new — to me. As a child of the 1970s, I had heard of Marriage Encounters retreats, but that sounded more like punishment than a gift.
Despite my fascination with the concept of retreating, I never managed to adapt this corporate practice for my personal use. The closest I came was on my 40th birthday when I asked my husband to take the three kids out of the house for 48 hours as a gift to me. I just wanted to be in the house alone. It was glorious and restorative, but I didn’t do any strategic thinking or purposeful planning.
But this year, a year when I started a new part-time job and launched paid subscriptions for this newsletter, a year when I’m *this close* to being an empty nester, this year is going to be different. This will be the year I finally plan an annual retreat for myself. And I’m going to follow a plan created by Jen Dary, a leadership coach and the founder of Plucky.
Jen’s been doing her own personal retreat for nearly a decade. “What happened was I started my own business and nobody told me to annual plan like they do in real companies,” she explains. “I was just like, ‘Okay, just make money as fast as you can in as many places as you can.’” But after a couple of years of that, she realized she needed to be more strategic. So her personal retreat, her Day of Big Dreaming (DOBD) as she calls it, came out of her need to get a sense of how her income would look for the upcoming year. Jen devotes an entire day between Christmas and New Year’s to dreaming about the upcoming year.
Jen’s DOBD helps her see when she needs to run hard and when she can walk at a more lesiurely pace. “So if I have a big trip planned for mid-year, I want to make sure my income is very healthy in Q1 so I can afford to take time off,” she explains. But it’s so much more than calendaring. “It's also a great forcing function to see what I'm actually ready to try/experiment with/commit to for my business.”
During her DOBD, Jen asks herself tough questions about her life — both at work and at home — and does her damnedest to answer them. “These are the kinds of questions we talk about late at night with friends,” she explains. “It’s a level of reflection that doesn’t show up on a random Tuesday afternoon. You need space for this stuff to come out. And, sadly, no one is coming to make space in your calendar for you.”
So how does she make the time? She does it during Dead Week, the week between Christmas and New Year’s. “I think for me, it's the perfect timing to have something to look forward to in a post-holiday setting, but also right before New Year's, which is when you're supposed to be having your big dreams,” explains Jen, who suggests you think of it as a more elaborate New Year's resolution or as pre-gaming NYE. "Okay, okay, we're all supposed to be new people January first? Well, I will be a new person December 28th."
This week tends to be a quiet week at work and at home, so you’re probably not going to miss much — if anything — in order to make this happen. Heck, it’s a great excuse to take a break from family togetherness and show your kids that you deserve to be prioritized. And if you have little ones, you might have visiting family who can keep them busy while you retreat.
Dead Week always puts me in a funk. Maybe it’s the fact that all three kids are at home and on wildly divergent schedules (one goes to bed just a couple of hours before another wakes up to work out; one is finishing lunch while the other starts breakfast). Maybe it’s just that the excitement and anticipation of the holidays is over and I’m left with an adrenaline deficit. Or maybe it’s because we’re stuck at home during a paid holiday because of the high schooler’s sports commitments. Whatever it is, this year I’m going to combat the funk with my own DOBD.
Luckily, Jen has provided me with a roadmpa. At first, her DOBD was something she did for herself as an entrepreneur trying to keep a lot of balls in the air. But when she mentioned it to family, friends and clients, they got curious. They had a lot of questions about the logistics and asked how they could plan their own DOBD. So in 2021, Jen introduced an e-course to help other people dream, too. She lays it all out for you: There’s a theme, an agenda, little videos to kick off each part of process — even a workbook.
The Day of Big Dreaming is designed to address the personal and the professional. Although we like to think of work and life as very separate buckets, she explains, the content of one often spill over into the other. “I found that it was way more fulfilling, to some extent, to have those two parts of my life in conversation,” she adds. So if, for instance, you’re a small business owner with a kid starting kindergarten in September, you might want to plan for a lighter workload during the fourth quarter so you can be a bit more flexible during that big transition. Or if you know you’re using your high school junior’s spring break to visit colleges, you should go ahead and request that time off now.
I’m so excited. Investing in myself feels like the perfect way to banish my holiday funk. I’ll be thinking about what I want to write and where I want to publish it. I’ll be planning some fun getaways with friends and I’ll take a closer look at where all my time goes.
When you think about it, moms probably need an annual retreat more than anyone else. The job of being a mother changes so drastically from year to year as our kids move from one stage to another. From toddlerhood to elementary school, from chauffeured middle schooler to a teenager who drives, from a senior who stays at home to a college kid you only see during school holidays. Each new stage of their lives ushers in a new stage in ours. And that requires an adjustment. An entire day to be intentional about your hopes and dreams — and, yes, the logistics — of the coming year is a gift we all deserve this holiday season.
Dream big,
Plan your own big day of dreaming
Ready for a self-paced day of reflection? Here’s what you need to do.
Purchase the DOBD or DIY it
I personally love the idea of outsourcing the planning so I’ve already purchased this year’s DOBD e-course from Plucky for $139. Jen is offering readers of this newsletter $20 off: Just use code SKIN23 at checkout. (Bonus: This is a really cost-effective way to dip your toe into coaching if you’re curious about that.) The course is available until the end of January. If you have a professional development budget, use it for this.
If you need a less expensive option, you can DIY your DOBD, but you need to give it some structure. Personally, I love a simple retrospective (or retro). They’re great for teams, of course, but there’s no reason you can do one solo. For a more personal twist, try using this liked/learned/lacked format instead of the usual start/stop/continue.
Pick a venue
My friend Stevie has done a personal retreat for years. “I’ve found that creating the space to reflect on the last year and dream about the year ahead only happens if I can create some distance from the distractions of my life,” she explains. She’s retreated in a friend’s office, at a hotel, even in a cabin in the woods. “The key for me is to be free of the little distractions that split my attention and limit my ‘possibility thinking’ or distort my true priorities.”
Jen likes to borrow someone's office with a big whiteboard, which is pretty easy to do at the end of December. “One year I did it at my lawyer's office, one year I did it in the church basement and one year I did it in Times Square at a prom dress company,” she says. You could also just buy a day pass at a co-working space.
Treat yourself
Remember, you’re investing in yourself. Make the day fun and comfortable. Jen buys herself a grande chai latte instead of her usual tall and grabs herself some yummy takeout for lunch. My BDOD will conclude with a little happy hour, during which I’ll toast myself and my big plans for 2024.
Don’t half-ass this:
Ideally, you devote an entire day to dreaming. Stevie carves out two days and an overnight for her personal off-site. You might be able to squeeze it into a half day, but an hour isn’t going to cut it. Certain seasons of life are not conducive to dreaming — and that’s OK. If you’re the parent of tiny tater tots, for instance, this may not be your year. “You can’t squeeze in a Day of Big Dreaming while the baby’s napping,” Jen explains. “You’re going to have a tiny dream. There's a certain point, especially with young children, where you don't need a DOBD, you need a nap.” If you’re in such a season of life, bookmark this for another time.
Go into “Do Not Disturb” mode
Block your calendar, turn off phone notifications and otherwise make yourself unavailable for anything other than dreaming. Ask the in-laws to take the kids. Or swap childcare with a friend so you can each do your own day of big dreaming. Do not try to multi-task.
Use the output in your next 1:1
You don’t have to be an entrepreneur to benefit from a DOBD. Jen encourages clients to use the output from a DOBD to have important conversations with their managers when they return to work. “Whether it’s a project or a promotion you’re after, what your boss really wants is to know what you want them to sign off on,” she explains. “So you go back to work and say, ‘I want to travel to the main office in Japan." ‘I want to lead a team.’ ‘I want to have interns.’ Whatever your vertical is, you can lay out what your expectations are and then you have a place to start the conversation.”
Follow-up
Dreaming is a great start, but you have to be intentional in order to stay on track. Plan a monthly breakfast for yourself and use it to pull out your DOBD workbook, your white board photos, your notes — whatever — and check in with yourself. Are you doing what you need to do to make your dreams come true?
Don’t be afraid to change course
Jen chooses a word of the year as part of her DOBD. “There have been a couple years where, around June I was like, ‘Ruh roh. Need a new word. That just isn't happening this year,’” she admits. Changing your mind about a word or a dream halfway through the year doesn’t mean you failed. It means you’re being thoughtful.