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How do I take a holiday without the business falling over?

Not by working harder before you go. By finding out, in advance and on purpose, what only you can do — and handing each of those to someone with the standard written down. A week away is the cheapest test of owner dependence there is, and the findings are more useful than the rest.

Do a dry run first

Be unreachable for one working day while still in town. Whatever breaks, or whatever people wait to ask you, is your list. That day costs nothing and tells you more than any amount of planning.

Hand over decisions, not just tasks

Telling someone what to do while you are away just moves the questions to your phone. Give them the decision, the limits, and permission to be wrong occasionally — that is the difference between cover and delegation.

Tell customers before you go

Who to call, when you are back, and that the person covering can actually decide things. Most upset about an absent owner is really upset about surprise, and it is entirely avoidable.

The list is the point

Whatever went wrong is not a reason not to go again. It is the map of what has to be written down, and you would not have found it any other way. Owners who never leave never learn where the business depends on them until something forces the issue.

Also asked

What if there is genuinely nobody to cover?
Then that is the finding, and it is worth acting on. A business that cannot survive one week without its owner is a business with one point of failure, whatever else is going well.
Should I check in while away?
A short scheduled window is more honest than pretending you will not look. Constantly available is not a holiday and it teaches everyone to wait for you.
How long should the first one be?
Longer than a long weekend, because a weekend can be absorbed by everyone just waiting. A week starts to reveal the real dependencies.

Related

Written for your trade

This is the kind of thing Solomon works through with owners using their own numbers. See how it works →