How to Run Your Own Goal Setting Retreat (8 Min Read) | Vol. 226

PSA – If you’d like to do your goal-setting retreat with us, Wendy and I are hosting our final The ONE Thing Summit & Goal Setting Retreat virtually on November 13–14. It’s two half days, so you can book a hotel nearby, enjoy your mornings, and join us for the sessions. Every attendee gets our 40+ page workbook walking you through the process. It’s arguably worth the ticket price alone. Learn more here.

October 23, 2026

“Unspoken expectations are premeditated resentments.” – Neil Strauss

How to Run Your Own Goal Setting Retreat

In 2006, Wendy and I had two kids under two, born 16 months apart. We had no family in town to help. Life was a blur of diapers, bottles, and very little sleep.

One day, Wendy suggested we get away for a weekend. Just the two of us. At the time, we had no idea this would become an annual ritual and play an essential role in our relationship and business success. 

The goal-setting retreat was born.

We booked our first-ever overnight babysitter and a cabin on a river in the Hill Country. Wendy planned the whole weekend. A nice dinner out. A slow morning. Then a list of questions she’d found online. Lunch. A massage. More questions.

I was nervous. I had no idea what we were getting into.

Here’s the funny part. The guy who would go on to co-write The ONE Thing didn’t set a single professional goal that weekend. Not one.

We’ve done it every year since. The questions have changed. Like our kids, the process has grown up. We’ve added pieces from The ONE Thing and, more recently, the Someday Letter. But the heart of it hasn’t changed. Two nights away to get on the same page about where we’re going and why.

I’m writing this for couples because that’s our story. (Flying solo? It still works. Running a business with partners or a leadership team? Most of this translates. Just skip the massage.)

Why Bother?

When you’re building a business and raising a family, the urgent always wins. You talk about school drop-offs, grocery lists, and who’s taking the dog to the vet. You rarely talk about where your life is headed.

A retreat makes space for the conversations that don’t happen at the kitchen table. Aging parents. College. Wills. What you each want the next ten years to look like. The things you expect from each other but have never said out loud.

It also builds a muscle. Goal setting gets easier and bolder every time you do it.

Wendy’s favorite example is money. Early on, we set a ten-year goal to become millionaires. At the time, our net worth was just $2,000. Our total household income didn’t add up to six figures. She thought the goal was ridiculous. Honestly, so did I.

We had no idea how to get there. So we guessed. We figured we needed to save about $1,500 a month. A monthly target that would add up to a down payment on a rental property each year. It wasn’t the right number. But it was close enough to get us moving. Each year, we saw how far we’d come and set a slightly bigger goal. Then a bigger one. We hit our “ridiculous” millionaire goal a little more than seven years later. Three years early. 

It’s not easy. But it’s not complicated either. Pick a goal. Take action. Course correct along the way. 

Before You Go

1. Pick your dates and get out of your habitat. Two nights is ideal. That gives you one full day plus the evenings on either side. We’ve held ours anywhere from September to January, but October and November are the sweet spot.

Get out of the house. At home, the laundry and the to-do list will stare back at you. You don’t need anything fancy. For years, we booked the cheapest downtown hotel we could find on a last-minute app.

Then remove every excuse in advance. Book the sitter. Board the dog. Set your autoresponder for the weekend. Bouncing between your dreams and your inbox kills the flow.

2. Do your homework. The retreat is for the big questions. Don’t waste it on busywork.

If you run a business, draft your business plan before you leave. Then you can spend your time on the why instead of the what.

Gather next year’s big dates. School breaks, conferences, family events. Planning vacations around them is one of my favorite parts.

Pull your numbers. What’s your monthly budget? What’s your net worth? Money is one of the top things couples fight about. Show up with facts, not feelings.

Finally, know your intention. What do you each want to walk away with?

3. Name the nerves. Let’s be honest. Treating your marriage like a business is super weird. If you’re the driven one, your partner may be wondering, Why not just plan a getaway and skip the work? 

Paint a better picture. Sell the benefits. Two nights away. A great dinner. Maybe a massage. A cup of coffee without a tiny someone throwing up in your lap. Parents of toddlers, I see you.

During the Retreat

4. Start with fun. We warm up with a nice dinner and easy conversation. Travel and bucket lists often come first. It’s like eating dessert first. Fun at the start and the end makes the hard work in the middle easier.

Not every retreat goes to plan. One year in wine country, we got almost nothing done. We did, however, have to splurge on a bigger wine fridge.

5. Dream before you plan. Start with the big picture. Revisit your core values. Our favorite newer tool is the Someday Letter. It asks you to look at least ten years out and describe the life you want to be living. Don’t let where you are today set the limits.

Then work backward. Your someday shapes your five-year goals. Your five-year goals shape your one-year goals. That’s Goal Setting to the Now.

Knowing your partner’s someday is powerful. It’s helped us make decisions one of us might never have made alone. A ranch sat on my five-year list for three years. As investors, it made zero sense. Then an unexpected partner showed up, and suddenly it did. Wendy says we bought a zoo. (She’s not wrong.)

Twelve years later, one of our new goals is to sell it. The kids are grown. What mattered then doesn’t matter now. That’s the beauty of doing this every year. You get to change your mind.

Clarity also makes it easier to say yes. Japan was on our five-year list, penciled in for two years out. When a friend invited me to go sooner, it was an easy yes.

We also keep a long list of questions sorted by stage of life. Kids turning ten? Have you started saving for college? Kids turning 18? You’ll need their permission to talk to their doctors. A medical power of attorney matters. The right question surfaces what’s not on your radar yet.

6. Cover your whole life. One of the biggest mistakes is only setting business and money goals. Life is also health, relationships, community, and hobbies.

We often create a category for each of our kids, our parents, and even key business partners. Sometimes a goal is as simple as taking someone to dinner. Sometimes it’s more of a hope. Wendy hopes our kids find loving partners someday. She’s not on a dating app for them. (She does ask our oldest about his love life. A lot.)

7. Give every goal an owner. What if you don’t agree? On a five-year list, “sure, let’s try” costs very little. The worst case is you look at it a year later and cross it off.

What makes a goal stick is an owner. Wendy once wanted to plant apple trees at the ranch. Nobody owned it, so it never happened. Every goal needs one of you to say, “That’s mine.”

8. Make room for the quieter voice. If you’re an entrepreneur, you probably think fast, talk fast, and are used to selling your vision. Your partner may process more slowly. Or they may have let you do the dreaming for years. Their dreams are still in there. They just haven’t said them out loud.

So ask questions. Then listen to the answers. Wendy’s advice is blunter. Sometimes the most powerful thing you can do is “shut the heck up.”

When you push hard on your business without explaining how it serves the family, your partner isn’t along for the ride. It’s like you stuffed them in the trunk and took off down a winding road. They don’t know where they’re going or why. A retreat invites them into the front seat.

After You Get Home

9. Date your goals. The other big mistake is treating the retreat as one and done. You can’t wait a whole year to look at your goals again.

Our goals live on our 411s. Most Sunday mornings, you’ll find one or both of us on the couch updating them. Wendy updates our net worth spreadsheet. (I fix it when it breaks.) Our weekly date night gives us space when something comes up.

We check in quarterly, too. In really hard seasons, we’ve even taken a second retreat. I carry our five-year goals, our one-year goals, and my Someday Letter in my notebook. Wendy keeps her 411 open on her computer. Find what works for you.

The first retreat is the hardest. It’s awkward. You’ll answer questions you’ve never thought about. But it gets easier every year. Your goals get bigger. Your conversations get better. And you start to see patterns. One recent year, we noticed we were both subtracting a lot. We weren’t sure yet what we were making space for. We only saw it because we had years of goals to look back on.

Wendy and I go deeper on all of this on this week’s episode of The ONE Thing Podcast. We talk through the mistakes couples make, the questions we’re overdue to answer again, and why I once had to wheel cases of wine out of our office lobby on a dolly. Give it a listen before you pack your bags.

Twenty years ago, I showed up to a cabin without a single professional goal. I’m so glad Wendy dragged me along.

Your first step is simple. Open your calendar and pick your dates.

One question to ponder in your thinking time: When will I make space to stop doing and start dreaming about the future?

Make an Impact!
Jay Papasan
Author | CEO | Coach