A proper break, fully offline, is the cheapest and most honest test of how your business really runs. Here's how to plan it so it tells you something useful.
By Ines Calder
When I ask a founder in a first call when they last had a proper holiday, the answer is often a long pause. Then something like: "We did a week in Portugal two years ago, but I was on my phone most mornings."
I don't raise it to be kind, although rest matters. I raise it because a two-week break, planned properly and taken fully offline, is the most honest diagnostic I know. It shows you, in a fortnight, exactly which parts of the business depend on you, and it costs nothing but a bit of nerve.
Why two weeks, not one
One week is easy to survive. You can clear the decks beforehand, push decisions to the following Monday and come back to a manageable pile. Your team knows you'll be back soon, so they wait.
Two weeks is different. Somewhere around day eight, decisions that can't wait start to arrive. A customer changes an order. Someone resigns. A supplier lets you down. Your team either makes those calls or doesn't, and whatever happens is information you can't get any other way.
Plan it like a project
Book it six months ahead, and tell everyone. Put the dates on the plan, not in your private diary. It signals that you're serious, and it gives the team half a year to get ready. One client, who runs a logistics company, booked and paid for his in February for the following August and wrote it on the one-page plan as a target alongside revenue and on-time deliveries.
Write the "while I'm away" sheet. One page, three parts:
- Who decides what. A named deputy for each area of the business, with the same limits they'd have if you were there, and one person who has the final word if the deputies disagree.
- What counts as an emergency. Keep it short: someone is hurt; a customer worth more than a tenth of revenue is threatening to leave; cash falls below an agreed floor; anything involving the police, a regulator or the press.
- One route to you. Only one person can contact you, only for something on the emergency list, and only by phone. Nobody emails "just to keep you in the loop".
Do a dry run. Take a long weekend a couple of months before, fully offline, with the sheet in place. You'll find two or three gaps. Fix them.
The holiday isn't the reward for building a business that runs without you. It's how you find out whether you have.
While you're away
Take your work email off your phone. I mean remove the account, not just turn off notifications. Leave the laptop at home. If you really can't face two weeks of silence, agree one fixed 20-minute call with your deputy on day seven, at a set time, and stick to it.
The first few days are uncomfortable. The logistics founder told me he sat in the kitchen on the first morning waiting for the phone to ring. It didn't. The one call he got in two weeks was about a lorry off the road near Leicester, which his chief operating officer had already sorted.
When you come back
This is the part that makes the test worth doing. Before you open your inbox, sit down with your deputies for an hour and ask three questions.
- What decisions did you make? Listen, and don't reverse any of them in the first week, unless one is genuinely dangerous. If you do, you'll get the same queue next time.
- When did you want me? Make a list of every moment someone wished they could ask you something. This list is gold. Each item is either a decision that needs a clearer owner, a limit that needs raising or information that only lives in your head.
- What went better than expected? There's always something. Say so, in front of the team.
Then take the "when did you want me" list and turn it into next quarter's priorities. In my experience it usually has between six and fifteen items on it. By the following year's holiday, most of them should be gone.
If two weeks feels impossible
Some founders read this and think: not in my business, not this year. Sometimes that's true. A sale going through, a key person on parental leave, a big contract in its first month. Fine. Then take the test in stages, and treat each stage as seriously as the full fortnight.
Start with one fully offline Friday a month for a quarter. Then a long weekend. Then a week. At each step, keep the "when did you want me" list and work through it before the next one. The aim isn't to prove you can disappear. It's to find out, as cheaply as possible, which parts of the business still run through you, and to fix them one at a time.
If after six months even a week still feels impossible, that is the answer to the test, and a very useful one to bring to your next planning day.
Scoring the test
You passed if the business traded normally, nothing on the emergency list happened without being handled, and your deputies made decisions you can live with. You don't need to have agreed with all of them.
You didn't pass if the team waited for you on anything that mattered, if you checked email "just once" (everyone can tell), or if you came back to a pile of decisions with your name on them. That's not a failure either. It's a very clear list of what to work on.
Most of my clients take their first two unplugged weeks within a year of starting. For some it's the first in a decade. Almost all of them tell me the same thing when they get back: the business was fine, and they weren't sure whether to be relieved or slightly offended. Both are the right answer.
Ines
