What do Anthony Bourdain, Indiana Jones, and that one lawyer who tries to “work from the beach” have in common?
It’s not that all three have mastered the art of typing emails while sweating through linen.
Instead, it’s about traveling without your law firm turning into a dumpster fire the second you leave town.
Bourdain built a whole life around being somewhere else, but the show still got made. Indiana Jones disappears for months, and somehow the university doesn’t collapse. I have questions. And you? You just want to take your kid to Disney without your paralegal texting, “Do you know where the Smith file is?” while you’re standing in line for Space Mountain pretending you’re not stressed.
Here are five tips to make it easier to travel while your firm keeps operating, without needing to fake your own death or bring your laptop to dinner like it’s a plus-one.
Tip 1: Decide Who Is “Captain Now” Before You Leave
If you’re the only person who can approve things, answer questions, or make decisions, congratulations, you’re not a firm owner. You’re a very stressed-out switchboard.
Before you travel, choose one person to be the captain. Not “everyone can decide.” That turns into The Purge, but with case notes.
This person needs three things:
Authority: They can make calls without waiting for your blessing Context: They know what matters and what does not A lane: What they can decide and what must wait
Pro move: send a one-page “If X, then Y” decision guide.
Example: “If a client threatens to fire us, call me. If the client is just mad about the timeline, follow the script and update them Friday.”
Tip 2: Build a “Vacation Mode” Communication System
Most travel stress comes from one lie we tell ourselves:
“If I’m available, nothing will go wrong.”
That’s like saying, “If I keep my hand on the stove, it won’t burn down the kitchen.”
Instead, create vacation-mode rules that your team and clients can actually follow.
Here’s a simple setup:
Client communication: “Jordan is out of office until Monday. The team is fully available. If this is urgent, here is the process.”
Team communication:
Call for true emergencies only. Everything else goes into a running list for your first day back.
Update cadence: “You will get updates on Tuesdays and Thursdays.” Or whatever your firm can consistently maintain.
Clients don’t need instant responses. They need predictable responses.
Nobody gets mad at Disney for making them wait 45 minutes for a ride. They get mad when the sign says 10 minutes and it’s actually 45.
Expectations are everything.
Tip 3: Make Your Monday Meeting Do the Heavy Lifting
I’m a big fan of Monday meetings. Not the “let’s all share feelings and hope the week goes well” kind.
I mean the kind where the team leaves knowing: • What matters this week • Who owns what • What fires are already handled
• What decisions are coming When you travel, the Monday meeting becomes your “set it and forget it” tool.
Before you leave, do a special version:
• Review top matters and deadlines • Assign a single point person per matter • Confirm what “good” looks like for the week
• Identify likely landmines, aka the clients who email like they’re paid per exclamation point
I once took a 13-month road trip while the firm kept running. Honestly, it ran better.
Sure, I worked more than expected, but it didn’t survive because I’m a wizard. It survived because the team had structure, ownership, and rhythm. The work didn’t require me to be the human router.
If your team can run a clean Monday meeting without you, travel gets a lot less dramatic.
Tip 4: Stop Being the “Only One Who Knows Where Stuff Is”
If your firm knowledge lives in your brain, your inbox, and a pile of sticky notes that looks like a conspiracy wall, travel will always feel impossible.
You need two things: • A single source of truth • A “Where is it?” map for your team
This is boring. It is also freedom.
Start with these three documents: • How we open a file
• How we move a case through the process • How we close a file
If your team can follow those without asking you questions, you can go eat tacos in another time zone like a normal person.
Also, if you think, “My cases are too unique for systems,” I get it. I used to say that too. Then I realized I was protecting my identity as The Only Person Who Can Do This.
Which is a cute identity until you want to take a vacation or, you know, be present for your actual life.
Tip 5: Plan Your Travel Schedule Like a Grown-Up, Not a College Kid
The biggest travel mistake I see law firm owners make is this:
They travel… but they don’t actually leave.
They work in the mornings, take calls at lunch, answer emails during dinner, and then wonder why the trip didn’t feel restful.
So pick one of these two options:
Option A: True Vacation • You are unavailable
• The team runs the firm • You check nothing and forget what day it is • You come back rested
Option B: CEO-Lite Travel • You work a preset window, like 30 minutes a day • One person filters what reaches you
• You do not “just quickly check” your inbox
Because that’s how you end up drafting a motion at a pool bar.
When my wife and I had the pregnancy conversation that forced a bigger rethink about life and business, one of the biggest takeaways was this:
“If your business only works when you’re constantly on call, it’s not supporting your life. Your life is supporting the business.”
That’s backwards.
And it’s fixable.
What This Looks Like in Real Life
I saw this recently with a client. They’re a husband-and-wife estate planning firm in the Midwest, and every vacation turned into a remote-work conference with bad Wi-Fi.
We implemented:
• One decision-making captain back at the office • A clean weekly meeting rhythm • A simple vacation-mode communication plan
• A documentation push for repeatable processes
Within a few weeks, the wife stopped being asked where every document was, and the husband no longer had to explain to intake whether they would take each case on a literally case-by-case basis.
Fast forward a few months and boom, they took a real family vacation, and the photos they sent me were awesome.
The best part wasn’t even the time savings.
It was the emotional shift from “I can’t leave” to “I can leave and it’ll be fine.”
That is the whole game.
Next week, we’re talking about what it actually looks like to build a business and a life that improve together instead of competing against each other. You’ll learn how to think beyond survival mode, make decisions with the long game in mind, and create systems, routines, and priorities that give you more freedom, clarity, and energy over time.
Until then, take five minutes and write down the top 10 questions your team asks you every week. Circle the ones that should never require you.