When did you last take two weeks off and not check your phone?
For a lot of owners the honest answer is never. Even on vacation, they’re answering texts by the pool and approving quotes at dinner.
That’s not a vacation. That’s working from a nicer chair.
The good news: it’s fixable. It takes a few weeks of prep and one practice run.
Why the business can’t run without you
It’s usually not that your team isn’t good enough. It’s that some decisions only you can make, because nobody else has ever been allowed to make them.
Pricing a job. Saying yes to a refund. Handling the customer who only trusts you. Paying the bills. Knowing which supplier to call when something breaks.
Each one is small. But stack them up and the business has to stop and wait for you, several times a day.
Find the decisions only you make
Spend one normal week writing down every decision that comes to you. Not tasks, decisions. Who asked, what they needed and what you said.
At the end of the week, sort the list into three piles.
- Hand it over. Someone else can decide this with a simple rule or a dollar limit.
- Write it down. It needs your know-how, but you can turn that into a checklist.
- Keep it, and plan around it. Truly yours. Do it before you leave or after you’re back.
Most owners find the first pile is bigger than they expected.
Hand it over in order
Don’t hand everything over the week before you fly. Start a month out.
Begin with the easy stuff. Small refunds, scheduling, ordering supplies. Give each job to one person, with a clear limit. For example: approve any refund under a set amount, and anything bigger waits.
Then move to the harder ones. Pricing, with a written price list. Customer problems, with a short guide on what you’d do.
Name one person as the decision-maker while you’re away. Tell the team. Tell your key customers too. It’s much easier for everyone when they know who to call.
Sort out the money side. Make sure someone can pay bills and run payroll, or schedule it all ahead of time. Talk to your bookkeeper about this early, not the week you leave.
Run a test before you go
This is the step most people skip. Don’t.
Two or three weeks before your trip, take two days off. Stay home if you want, but act like you’re gone. Don’t reply to anything unless it’s an emergency you agreed on in advance.
When you’re back, ask the team what got stuck. Every stuck item is something to fix before the real trip.
If the business can’t get through two quiet days, it won’t get through two weeks. Find out early.
Agree on what counts as an emergency
Your team needs to know when to call you. Keep it short and specific. Someone’s hurt. A big customer is about to walk. A legal or safety issue. Everything else waits, or gets decided by your stand-in.
Then leave the phone in a drawer. If you check it every day, your team will learn to wait for you, and you’re right back where you started.
When you get back, don’t take everything back at once. Leave the handed-over decisions where they are. That’s how the next break gets easier.
Do this this week
- Start a list of every decision that comes to you. Keep it going for five working days.
- Sort the list into hand it over, write it down, and keep it.
- Pick the three easiest to hand over and give them to someone this week, with a clear limit.
- Choose your stand-in and tell them the plan.
- Put the dates for a two-day test in your calendar, a few weeks before the trip you want to take.
Playbook No. 02 has the full owner-away checklist, from the first decision list to the two-week test. The episode shows how a business runs when the owner is away.
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Kevin’s been writing code for thirty years. Now he helps owners use AI to get time and money back, and hosts BizPlaybooks.
