Our first company workcation was a beach house in north Florida about fifteen years ago. Five team members. Five spouses. Seventeen kids under the age of twelve. Sand everywhere. A long table on the porch that became where the actual meetings happened.
It was a logistical mess. It was the most important week we had ever spent together as a company. The week worked because we were all in the same building, our families were braided together, and nobody could leave the room when the conversation got hard.
Fifteen years later we still do it. The most recent version was a cruise. No kids. Just the team and their spouses. The point was the same. Get out of the building. Be in the room together. Spend the leverage you have built on the people who built it with you.
I am writing this in 2026 because most owners are about to under-invest in this exact muscle. AI has freed up so much time inside the building that the temptation is to keep working in the building. That is the wrong answer.
What the in-room oxygen actually is
Anybody who has ever been to a great conference knows the feeling I am about to describe. You walk into the room. The energy in the air is different. The conversations between sessions are better than the sessions. You stay up too late at dinner with three people you have only known for two days, and a year later you can still quote things they said.
You cannot replicate that on a Zoom. You can replicate the agenda. You cannot replicate the oxygen.
For about three years I let myself believe we were past the in-room thing. We had built a fully distributed team that could ship great work without ever being in the same room. The proof was the work. The work was good. Why pay for plane tickets and hotels when the dashboard says everything is fine?
Here is what the dashboard did not show. The trust we had built up in our early years was getting drawn down. Quietly. The hard conversations were routed through Slack instead of a chair across from the person. The new hires had never met any of us in person.
Trust is a bank account. The dashboard tells you the inflows. It does not tell you the outflows. In a distributed company, the outflow is silence. You only see the bill when somebody quits or a client leaves.
The fix was not more bandwidth. The fix was airplanes.
The new push at the agency
I have been telling the team this all year. Get on airplanes. Take people out for coffee. Take clients to drinks and dinners. Do live workshops in person. Do live events.
Some of them looked at me like I had lost the plot. We had spent the last decade building a remote-first agency. Why are you sending us back to the road?
The answer is the math has changed.
The reason we went remote-first was that the marginal cost of distance was high and the marginal cost of bandwidth was low. AI just ate a chunk of the work that used to take hours of focus. The marginal cost of bandwidth is even lower now. But the marginal value of distance has been quietly going up. The competitor across town who flies their team to a beach house twice a year is going to win the next great account, and I would rather it was us.
The other thing the math has changed is the volume of communication. AI lets me send more messages, faster, to more people. It does not let me know more people. The single in-person hour I have with a client this quarter is worth more than the fifty automated touches I could send in the same week. We have to spend the time saved on the work the saved time was for.
The workcation versus the off-site
There is a difference between an off-site and a workcation. You need both, in different seasons.
An off-site is a tightly designed working session. You have a real agenda. You have specific decisions to make by the time everyone goes home. You have prework. You leave with a one-page document.
A workcation is closer to a long shared meal. You bring people. You bring spouses if it works in your culture. You build in plenty of unscheduled time. You let the trust refill on its own.
The mistake most owners make is to confuse the two. They book a workcation and then stuff it with an off-site agenda, and everybody goes home tired. Or they book an off-site and try to pretend it is a vacation, and the decisions never get made. Decide which one you are running. Tell the team which one you are running. Then run that one well.
action
1. Decide which you are running: off-site or workcation. Write a one-page brief. 2. Pick a quiet season - late February or the week after Labor Day. 3. Pick a private room you will all share for meals. Driving distance is fine. 4. Pick three meals together and one optional shared activity per day. Leave the rest open. 5. Put a date on the calendar this week and tell one person.
The room is the work.
