The Three Types of Think Weeks That Changed How I Lead
Nine years, nearly twenty Think Weeks, and three distinct formats later: here’s what worked, what didn’t, and how you can design your own version of focus.
Nine years ago, I needed to get away.
The pressure of running a business, leading a team, tromping through the weeds, and answering so many questions was getting to me.
But I didn’t need a vacation. No, that was not the root issue.
What I needed was a time away to focus. A time away to confer with a few others who were in a similar stage of growing a business. An amalgamation of solitude and inspiration sprinkled with conversation.
Then, I stumbled upon Think Weeks.
I’ve written about “Think Weeks” before.
To catch you up, a “Think Week,” inspired by Bill Gates’s famous weeks away to read, reflect, and process, is any multi-day period of time dedicated to working “on” stuff rather than “in” stuff. By my count, I’ve conducted nearly 20 of these sessions, and the results never fall short.
Over time, I’ve honed my Think Week approach, tried different versions, and tested various ways to maintain my focus.
The result? In the last 12 months, I’ve had three Think Weeks, each different in its own regard. Here is a breakdown of each type, what worked, and thoughts on which version might work for you.
Think Week Type 1: The Escape to Solitude
Every October, I spend three days in Southern California by myself. This was my first Think Week type. My loving, patient, and understanding wife lets me depart for our annual family vacation a few days early, giving me a few days alone before their arrival.
I’ve landed on a pattern of breaking the three days into dedicated focus times.
The Structure
Day 0: Fly in to San Diego. Unpack. Hit the grocery store for the necessities. Race to my favorite spot on the deck with a cold beverage (something not very exciting these days...) and simply decompress from the days, weeks, and months prior. Early to bed!
Day 1: The focus is on my personal mission. I update my 5-year vision for the future, a document that, well, describes, in obsessive detail, what I’d like life to look like five years from now. Commencing my Think Week with this proverbial north star in mind triggers clarity I lack coming into the session. This exercise typically takes 2-3 hours. I then pivot to my Think Week list in Trello (which I regularly add to as interesting projects pop into my head), outlining how I’d like to spend the next few days and determining which projects I’ll undertake.
After lunch, I choose 1-2 personal projects of interest and dive deeply into them. I use the pomodoro method to organize my time (I prefer 35 minutes of work and 7 minutes of “not work”), and force myself to “stay in the clouds.” I intentionally avoid working “in the weeds” because that’s not what Think Week is about.
Day 2-3: These days look very similar.
I start with 30-45 minutes of a brisk workout. I then chose 1-2 work projects to focus on before lunch. Lunch always includes a long walk and time sitting on the deck, observing the world and thinking about my most recent focus time. It’s crazy how often, in these moments, some of my most helpful thoughts come to me. It’s almost like the tide of disruptive thoughts ebbs back to the sea, leaving amazing ideas exposed on the shore.
I typically stop working around 4:30 and spend more time walking, listening to music, and having an early dinner out. These are good days!
The Results
This Think Week type leaves me excited, refreshed, ready to end the year strong, and anticipating great things in the year to come. I typically leave with a general plan for each business for the following year, including a basic financial model (using the Simple Numbers “Minimum-Target-Stretch” forecasting method). I also leave craving time with my family, and the “carrot” of having them arrive at the end of day 3 is beneficial. I find 3 days alone, with minimal human contact, about as long as even this introvert can take!
Think Week Type 2: The Collaborative Approach
In the spring, I embark on a very different type of Think Week, one that includes 4-6 other business owners with whom I have long-standing, close connections.
We’ve been doing a version of this Think Week together for nearly a decade, and these times never disappoint.
The Structure
Day 0: We rent a large VRBO in a scenic location (think mountains or beach). The only venue requirements are: everyone gets their own room, a large great room with plenty of table space, and a hot tub. We used to have “copious amounts of bourbon” on the list, but all of us have gotten older and more sober...
We also buy enough groceries to last 3 days, other than dinners, which are out.
Day 1-2: These days look similar. Everyone starts working when they prefer, but usually between 7 and 9. Some like to work in the same room with others, while others prefer working alone. Regardless, each person is practicing “deep work” on projects intended to move the needle professionally, personally, or relationally.
We all take lunch around the same time, chatting about our progress, ideas, and any collaborative feedback we may need. It’s during these lunches that some of my favorite conversations occur, sparking ideas I may never have considered or approaches I’ve been missing.
After lunch, we dive into 3-4 hours of additional individual work, then enjoy a dinner out together. Once again, the dinner conversation is intended to spark ideas, problem solve, and collaborate.
Day 3: Since the venue is a VRBO, we spend 2-3 hours in the morning in individual work sessions before packing up and heading home.
The Results
While the individual work sessions are productive and fruitful, my favorite part of this Think Week version is the conversation before, during, and after deep work sessions. I’m fortunate to take this trip with brilliant operators who push, challenge, question, and support in a truly generous way. I leave inspired and with a half dozen projects to consider for the months to come.
(BTW, this collaborative Think Week concept continues to garner interest. I’m considering hosting a 2nd one each year with a new cohort. If you want to learn more, fill out this quick form and you’ll be the first to know when this turns from concept to reality, likely in mid-2026...)
Think Week Type 3: The Partner Retreat
This year, I tried a new Think Week configuration, and it worked swimmingly.
It went like this:
Me: Hey, I’m going to do a Think Week in August, want to come with me?
Wife: Where?
Me: The mountains. Borrow a cabin from our friends. I can spend a few days focusing, and you can do whatever you want!
Wife: Um, yes. 100%. I’m in.
Thus, the first Couples Think Week was born.
The Structure
Day 0: Travel to the cabin. Enjoy a lovely evening together, relaxing, connecting, catching up, and binge-watching The Four Seasons...
Day 1-2: Wake up early and enjoy the sunrise with a cup of coffee. Take the dog on a long walk. Think through an approach to the day.
Just like the other Think Weeks, I break the day into 3-4 hours of work before and after lunch. The focus, as always, is on big-picture, 30,000-foot projects that are difficult or impossible to accomplish amid day-to-day life back home. I admit, I have to fight the urge to dive into email or work on surface-level projects. But fight I do. It’s worth it.
In the evenings, my wife and I enjoyed dinner, out or in, and some exceptional conversation. For me, there is something about the serenity of the mountains, having spent a day in deep thought and then a relaxing evening, that brings forth the kind of conversation that brings people together. It’s a fantastic recipe.
Day 3: Finish out any lingering projects and head on down the mountain.
The Results
The same excellent output as the other Think Weeks, with the added bonus of connecting with my wife. And she loved it too. I was concerned she’d be bored or feel ignored during the day. Turns out she doesn’t mind me ignoring her one bit. [wink]
Wrap Up
We hear it all the time from business owners and leaders: “I need to spend more time working on the business rather than in the business.”
But here’s the question: are we intentionally making time to do this?
I’ve found that I can talk about this ad nauseam, but unless I am disciplined in getting away, it rarely, if ever, happens.
As you can see, Think Week can take many forms. Each is beneficial for me in its own right, and I think you’d find the same.
Let me encourage you to choose a version above (or synthesize a new version) and try it out.
You might be surprised by the results.
Thanks for reading this post. I appreciate you. In return, please share this with those you know who may be interested.
Free Guide: 🚀 Build Your AI Dream Team (In One Day)
I created 10 Custom GPTs to handle key roles inside my business—CFO, ops, marketing, HR, and more.
The full guide includes templates, my step-by-step setup, and how we rolled it out across the team.
Things I've Enjoyed Lately: When our old Keurig went down, we decided we were done with the little plastic pods and ready for an upgrade. In walked this bad boy. The Ninja Luxe Cafe 3-in1 has been one of our best household purchases in years. Our Starbucks consumption has plummeted by 80% or more, and our teen daughter has tried more recipes than Julie Child on coke. Highly recommend!