Every year, around Rosh Hashanah, our family has a tradition that my kids now expect.
We call it our Annual Family Retreat.
For the past three years, we’ve set aside a few uninterrupted hours to look back on the past year, talk about what we’re grateful for, reflect on what we’d like to do differently, and dream about the year ahead.
The retreat isn’t the same every year. As our kids grow, our conversations change. I tweak our workbook each year to reflect their ages, what’s happening in our family, and the season of life we’re in. Some activities have become traditions we look forward to, while others evolve right alongside us.
It’s become one of my favorite days of the year.
As an entrepreneur, I spend several days every year planning for my business. We review what’s working, what’s not, and where we want to go next. We set goals, talk through challenges, and make sure our leadership team is aligned before the new year begins.
A few years ago, I found myself asking:
If I spend this much time intentionally planning for my business, why wouldn’t I do the same for my family?
Most families spend their lives reacting. We rush from school to work, from sports to homework, from one activity to the next, hoping that somewhere in the middle of all the busyness, we’re becoming the family we want to be.
But hope isn’t a strategy.
Strong families, like strong businesses, don’t happen by accident. They grow through intentional conversations, shared values, and making time for what matters most.
That’s what our Annual Family Retreat has become.
We Start with Creativity
I’ve learned that if you hand kids a workbook and ask them to spend the afternoon reflecting, you’ll probably lose them within five minutes.
So we always begin with something fun.
One of our exercises is the 60 Ideas Exercise.
We’ll pick a category and challenge everyone to come up with ten ideas as quickly as they can. It might be ten business ideas, ten ways to snap out of a bad mood, ten inventions that would make life easier, or ten things you’d want if you were stranded on a deserted island.
The answers are often hilarious.
The point isn’t to come up with brilliant ideas.
It’s to get everyone thinking creatively, laughing together, and reminding ourselves that there are no wrong ideas during brainstorming.
By the time we’re finished, everyone is engaged, relaxed, and ready for the deeper conversations.
Then We Look Back
Before we think about the future, we spend time talking honestly about the past year.
What were our favorite family memories?
Did we make enough time for each other?
What vacations stood out?
Did we read as much as we wanted?
Were we healthy?
Did we grow in our relationships with Hashem and with one another?
It’s so easy to focus on everything we didn’t accomplish.
This exercise forces us to celebrate what went well before talking about what we’d like to improve.
Sometimes the kids bring up moments I had completely forgotten, an afternoon at the beach, a fun family dinner, or a simple conversation that meant more to them than I ever realized.
Those moments remind me that what children remember isn’t always what parents expect.
We Talk About Our Values
Every family has values.
The question is whether we’ve ever taken the time to define them together.
We talk about kindness.
Putting family first.
Gratitude.
Responsibility.
Generosity.
These aren’t lectures.
They’re conversations.
Sometimes our kids see things differently than we do.
Sometimes they challenge us.
Sometimes they remind us that they’re listening far more closely than we realize.
Those discussions have become some of the best moments of the retreat because they help us define not just what we do as a family, but who we want to become.
Then We Dream
This is everyone’s favorite part.
We each set personal goals for the coming year, but we also create goals as a family.
Where do we want to travel?
What healthy habits do we want to build?
How do we want to spend more quality time together?
What would make this year feel meaningful?
The kids make a list of the families they would like to invite for Shabbos during the coming year.
It’s a simple exercise, but it reminds us that building a meaningful life isn’t only about achieving goals.
It’s also about opening our home, strengthening relationships, and creating community.
Why We Keep Doing It
If you asked my kids what they remember most about these retreats, I don’t think they’d say the workbook.
They’d remember the conversations.
They’d remember laughing together.
They’d remember feeling heard.
They’d remember talking about dreams instead of schedules.
Over the years, our workbooks have become a time capsule of our family.
Throughout the year, the kids will sometimes pull out a workbook from a previous year and flip through it. They laugh at goals they wrote when they were younger, remember family moments they had forgotten, and get excited when they realize how many of those goals they actually achieved.
It’s a reminder that growth doesn’t happen all at once. Looking back helps them see how much they’ve changed, what they’ve accomplished, and how far they’ve come. It also gives them confidence to dream a little bigger the next time we sit down together.
In a world that’s always focused on what’s next, taking time to celebrate progress is a gift.
In a world full of constant notifications and endless distractions, setting aside a few intentional hours each year has become one of the greatest gifts we give ourselves.
Not because we accomplish every goal we write down.
We don’t.
Not because everything goes according to plan.
It never does.
But because we make time to pause.
To listen.
To reflect.
To dream.
I’ve spent years learning that successful businesses don’t grow by accident.
The same is true for families.
The strongest families aren’t necessarily the ones with the fewest challenges. They’re the ones who create space to communicate, grow together, and return to what matters most.
Our Annual Family Retreat has become one of the ways we do that.
The systems I’ve built have helped me grow a business.
But the tradition I’m most proud of is the one we’re building at home.
