The Born Freelancer Asks, Do We Dare Ever Take a Holiday?

This series of posts by the Born Freelancer shares personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? We’d love to hear from you in the comments.


Aside from asking what should I charge, it is probably the question I hear the most often (especially around this time of year) from novice freelancers:

“Do I dare ever take a holiday?”

It is certainly one of the key questions I continually asked myself for far too many years when I first started my professional life as a freelancer.

The fear most paramount in our minds is, of course, that during any holiday an offer of work will come up and by missing it we will lose a new wonderful revenue stream or even worse, that life changing-career making break that will win us that much sought after Pulitzer or Academy award that we secretly dream about night after night.

Reality check! It is much more likely that you will miss no such opportunities. In fact, the chances are much greater of inflicting upon yourself negative consequences regarding your health and creativity as a result of living a freelancing life consisting of all work and no play.

This truth I have learned through a lifetime of painful trial and error. In sharing my experiences I am hoping to spare you some of your own.

My evolving attitude towards holidays

Once upon a time I too feared to take any time off the freelancing merry-go-round. I was younger and greener and thought time off was for those who didn’t have what it took to succeed as a freelancer. In a word, “wimps.”

This attitude made family and personal relationships suffer needlessly as well as having a slowly corroding effect on my energies and morale.

Eventually I decided I should take holidays but would be willing to cancel them on a moment’s notice if an offer of work came up. This seemed an ideal compromise at the time.

And like all compromises it led to dissatisfaction on all sides.

In fact planning and then canceling holidays caused more aggravation amongst family and friends and myself than not having any plans to holiday at all.

Not to mention the financial cost of cancelled flights, hotel rooms and show tickets.

So I came up with another solution.

I could go on holidays but if work came up I would do the work concurrently while on holiday. Brilliant!

This led to a number of memorable holidays. Memorable meaning both the holidays were ruined for me and family members and the work was completed unsatisfactorily.

My usual working routine had been totally abrogated and I was not able to fully concentrate properly. Additionally I resented the work intruding upon my holiday time which did not put me in the optimal mood to be at my best creatively nor to share whatever leftover down time there was with family and friends. It was a lose-lose situation all around. All in all, it was pretty much the worst of all my solutions to date.

So finally I took the inevitable plunge. I would declare work-free holiday zones in my annual schedule that would remain exactly that no matter what the professional provocation.

It was the best decision I ever made for my health and sanity and family and for maintaining my lifelong status as a working freelancer.

Early days

Admittedly, at first there were bugs to work out of my newly declared state of emancipation.

The plan was to warn all existing clients of any “no work” zones, usually a couple weeks in mid summer when I would drop off the planet (physically as well as online) with family and friends and focus on quality in person face time.

Warnings (reminders) went out months before. Then weeks.

Ongoing projects were completed.

New clients were informed new assignments would not be accepted until after the no-work period had ended.

I never specified with most clients why it was a no-work period. I just made it clear I would not be available. I figured I would let their imaginations fill in the blanks. Perhaps I was a secret agent on assignment?

A few old and supposedly trusted clients were let in on the secret – to my lasting regret.

Why regret?

Because a couple of them (consciously or otherwise) attempted to sabotage me. They were the ones who threw tantalizing work offers my way days or even hours before my holidays were to begin. “Hey, it’s only a holiday, right? You can always take one later…”

Tempted as I was (and trust me I was) I declined and stuck to my new holiday agenda.

I lost a few jobs, it is true. But I came to understand that those who threw such offers at me at the last moment did so deliberately to wrestle away control over my own life. I could finally see they were not the type of employers I wished to work for long term any more. Clearly they could’ve thrown the work my way well in advance. It’s just the chance to mess around with my life proved irresistible. Well, much to their surprise, I resisted quite successfully by taking full control and responsibility for my freelancing life and showing myself the self-respect that we all deserve and must give ourselves before anyone else will.


I have detailed my evolving attitude towards taking time off to show how it came into being. It might not be for everyone but it works for me to take a holiday (physically as well as online) and stick to it without exception (illness or family emergencies aside.) It has enabled me to live the freelancing life with relative health and sanity over the long term with less burnout and creative blocks than I believe I would have experienced otherwise.

So what’s the big deal about holidays? Why all these words about something most 9 to 5’ers take for granted?

Benefits from taking time off…

* Rest

* Lowered blood pressure

* Renewed health, extra energy

* Replenished family and personal contacts

* Emerging from the rut, seeing new possibilities, being exposed to new ideas

* Creative renewal

* … really, need I go on?

Update: I have just returned from holiday on a friend’s farm. A city kid by birth and later by choice, I get nervous when I am disconnected from the “civilized” world and can’t walk within minutes to the nearest convenience store, cafe or ATM.

But taking time off and away from all my usual routines has given me energy and creative ideas like I’ve not had in months. I feel great. Now, you don’t have to go far away or spend a lot, you can always just have a “stay-cation” in your own town or city. Or you can go stay with friends as I did and help out with their summer plans. (I helped paint a farm building.)

I would posit that the greatest benefit of all comes from just feeling like you have gained some control over your life again.

The takeaway

As freelancers our good health is our greatest asset. Without it our work will grind to a halt and when that happens so do our revenue streams. Without it our creativity will become impaired and without that we are unemployable.

Taking time off and completely away from my regular routine, getting away from the familiar and experiencing the unfamiliar for a short break, is one of the most important tools in my freelancer’s toolbox for keeping happy and healthy and employable.

The seeming short term loses (possibly employment) are vastly over-compensated by the numerous long term advantages – better health and greater creativity. It took me years to figure out what now appears to be so obvious. The trick was to figure out what was best for me – not for my clients – although in the end they too would benefit.

And then all I had to do was dare to do it.

You can contact the author with questions for future columns: thebornfreelancer at gmail dot com.


Do you make time to get away from it all every year like The Born Freelancer? Or have you found your own solution to the dilemma of reconciling the freelancing life with taking time off for holidays? Please share your thoughts using the comments feature below.

Posted on August 14, 2018 at 10:00 pm by editor · · Tagged with: , , , ,

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