Why Vacations Go to Die

Remember that old September writing assignment from school?

How I Spent My Summer Vacation.

Safe to say, this is not that.

This is How Are You Spending Your Summer Vacation? because if you run a business, summer does not just happen. It gets claimed. Quietly at first. A client request here. A deadline there. One project that “just needs a bit more attention.” And before you know it, the season you thought you would enjoy has been chewed up by your own calendar.

It is only early April, and already it feels a little late to be making summer plans.

That feeling matters.

Because if vacation waits until business “settles down,” there is a very good chance it never arrives at all.

Here’s what I know now.

After a few years of running my own business, a vacation was basically reduced to the five or six hours I managed to sleep each day.

Everything else went to work.

Working in the business. Working on the business. Thinking about the business when I should have been paying attention to the rest of my life. Even when I was technically off, my brain was still sitting at the desk.

These days, vacation planning has become one of my favourite habits.

Not because I have turned into some grand master planner. I have not. I still do better with ideas, options, and flexibility than I do with colour-coded itineraries that start to feel a bit... controlling.

But adding a travel trailer changed something for me.

I call it my mobile home, and I mean that with true affection.

Being able to haul around my own little version of comfort has given me a level of freedom and ease I honestly did not think was available to me. It is not fancy. It is not dramatic. It’s my version of luxury.

This is where the lesson started for me.

Years ago, when I was working in corporate, I had a conversation with a CPA named Paul that stuck with me.

He had a calm, grounded way about him. You knew he was fully engaged in listening and choosing his words of guidance carefully.

We were talking through year-end and audit questions when the topic of unused vacation came up. A couple of employees were not taking their allotted time off. Paul flagged it immediately.

First, from a controls perspective.

Because in financial environments, people who never step away can create risk. Sometimes that risk is innocent. Sometimes it is not. Either way, it is worth paying attention to.

But that was not the only point he made.

He also told me that people in financial work needed real holidays. Regularly.

Yes, because more eyes on the same work matter.
Yes, because separation of duties matters.
And yes, because the human brain is not designed to stay switched on all the time.

That part stayed with me.

Because whether you are running payroll, managing client finances, or carrying the weight of your own business decisions, there is a kind of pressure that never fully announces itself. It just sits there. Quiet and constant.

Get it right.
Do not miss anything.
No room for error.

And after a while, that starts to feel like that’s just the way it is.

It is not normal.

It is just common.

And that is where vacations go to die.

The problem is when you start treating a vacation like a reward that gets earned only after everything is done.

Which is funny, in the bleakest possible way, because everything is never done.

There will always be one more email. One more client request. One more loose end. One more reason to wait.

Later is a sneaky thief.

And if you are already overwhelmed with getting through today, later becomes never with shocking efficiency.

This is where CASH becomes real.

Coach asks the question you have been avoiding:
When are you actually taking time off?

Action means you put the dates on the calendar now, not once summer is already halfway gone.

Support means your business is not built so tightly around you that everything wobbles the second you step away.

Habits means vacation planning becomes normal. Expected. Built in. Not a reward for exhaustion.

That is the part I care about most.

Not a perfect holiday.

But a preview of what life after business could look like.

So this is your April nudge.

Plan your summer holiday.

You can change the details anytime. Block the days.

Hit reply and finish this sentence:

My summer luxury or indulgence is this…

👉 If you found value here, forward this to a friend or colleague who’s ready to melt the ice in their own business.
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