Here’s How to Take 24+ Days Off Without Falling Behind

Photo credit: Yan Krukau on

Dear Entrepreneurs: Here’s How to Take 24+ Days Off Without Falling Behind

Truth bomb: The vacation game is rigged against busy entrepreneurs. The traditional 2-week vacation is designed for folks with 9-to-5 jobs. It’s a round hole – and we’re square pegs.

For years, I struggled with the madness of trying to take 14 consecutive days off work. 

In the weeks leading up to my holiday, I would obsessively weave a complex web of strategies to accommodate my impending absence. But, despite my best efforts, things would go awry. 

A client would have an unexpected need. An employee would get sick. An opportunity would appear that demanded my attention.

Inevitably, I would have to apologize to family and friends for dealing with work stuff while on vacation. Or I would ignore the work stuff and come back to find irate clients, stressed employees, and missed opportunities. 

Either way, I felt bad, because no one likes to fail, and I was clearly FAILING at taking a vacation!

But here’s the thing…

The purpose of a vacation is NOT to show other people that you can achieve their version of work-life balance.

The purpose is to rest and rejuvenate. Period. 

So, I stopped playing the 14-day vacation game and started playing by my own rules. 

Here’s how I take 24+ days off every year without falling behind:

Step 1:

On the last week of each month, I look at my calendar for the upcoming month. I ponder what that month looked like last year and consider my goals for this year.

Step 2:

I pick two days that seem reasonably calm and inconsequential and designate them as vacation days. I block those days off on scheduling apps so no one can inadvertently book my time. And I write them on a small pink Post-It that I stick on the corner of my desk. It reminds me to factor my vacation days into ongoing discussions and plans.

Step 3:

I take each of my designated days off and live happily ever after. The end. 🙂

That’s it. It’s that easy.

Note: Don’t push yourself to add more days but add them if it works for you. The goal is to enjoy well-deserved downtime. There’s no perfect number. Two works for me. Maybe you can do four. Or maybe you can only squeeze in one. YOU DO YOU!

And when it comes to planning out those days, do whatever the hell you want to do.

Sometimes I go to the spa or take a day trip with a friend. Other times, I watch movies on my sofa. Occasionally, I re-organize a closet or paint a room of my house. 

Remember that these are YOUR vacation days. There’s no right way versus wrong way to relax. Do what feels good for you.


When it comes to that two-week family holiday… 

Take it if you can. But make it an add-on, not a replacement for your scheduled monthly days. And customize the longer holiday so it can be restful instead of stressful. 

Personally, I set aside an hour in the morning to touch base with my work. And I make no apologies! 

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