The Born Freelancer on Knowing When to Leave the Party

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.


In my last column I wrote about using the current crisis as a catalyst for change by moving into freelancing.

Today I want to explore the opposite side of the coin. Namely, using this crisis as a catalyst for change by leaving a freelancing career for a more conventional 9 to 5 one.

Heretical for a site devoted to freelancing?


Perhaps one of the best kept dirty little secrets of professional freelancing is this:

Many of us will need to take a break from it occasionally and some may never return.

To leave or not to leave: these are some questions

Part 1 – money

Bottom line, we are in freelancing to make a living. The best one we can. If we can’t, why are we freelancers?

But an immediate lack of cash flow is not necessarily the kiss of death for a freelancing career.

Freelancing is a lifestyle of multi-faceted ups and downs. Its financial prosperity can fluctuate, often seasonally, depending upon the nature of your brand.

Ask yourself, is this just another seasonal low period? Has the crisis permanently impacted my revenue streams or is it just a temporary glitch?

If I’ve lost clients, have I been proactive attempting to acquire more?

If my specialty has had its market “dry up” is it temporary or permanent? Can I pivot my skills and experience to take advantage of whatever new options are beginning to emerge in the marketplace?

If I’ve not been able to pay rent or property taxes during the current crisis, have I (and/or my landlord) investigated the various provincial and federal government bailout programs available to assist tenants and property owners during these unprecedented times?

Did I qualify for CERB? Will I qualify for the new extended/revamped EI benefits?


A strictly enforced budget and a healthy savings account are key factors in weathering any fallow periods in freelancing.


Can you lock down your budget, eliminating more non-essential purchases during this difficult patch?

For example, can you moth-ball your car and only use a bicycle or public transit?

Do you need such elaborate internet and cable? Have you tried renegotiating or switching? Canadians pay the most anywhere in the world for internet, cable and cellphones.

Have you thought about cancelling your cable and buying a digital OTR (over-the-air) antenna? In most urban areas many television stations still have OTA signals that can be viewed for free.


Assuming you have diligently saved during the “good days,” can you draw upon your savings to keep afloat?

Non-recurring emergencies can, of course, negatively impact savings.

If your unexpected expenses are health related, do you have supplementary coverage from your union that you can activate? You might be spared additional expenses with coverage you already have.

(An aside about about health costs: This is one budget item you should try never to scrimp on. Fortunately, not having supplemental coverage may not be as devastating here in Canada as it might be south of the border — where some equate the logic ethicality of universally-available health care with an absurd socialist plot usurping their right to be ill and die. But sustaining the optimal health care coverage we can afford is an absolute priority for freelancers. Without our health we cannot work and without work we have no income.)

Need a loan or mortgage?


It’s not so easy being a full-time freelancer if you need to take out a mortgage or line of credit. There is a widespread impression amongst many corporate financial institutions that freelancers are somehow an unacceptable risk. The fact that more and more individuals every year successfully turn into freelancers seems to elude their ignorant outmoded thinking.

When I investigated pursuing a line of credit (which I reported on earlier for this site) I discovered it would count more in assessing creditworthiness to have a part time job, even a crummy one, than having a successful freelancing career. Be warned.


Go ahead. Assess your freelancing career by asking all the above questions. Plot your financial budget for six months, even a year ahead.

If you see no hope on the horizon, no likelihood of improvement, no reasonable options to get you through this crisis, then you may indeed need to change and leave freelancing.

For a while? For good? For part time or full time?

Only you can decide.

Part 2: burnout — another way of saying “I need a change”?

This can be a much more subjective, intangible problem to contemplate.

But its impact can be just as deadly as any lack of money.

Perhaps things are not going the way they used to — or should — go.

Maybe emails and pitches are getting rejected out of hand with increasing regularity.

So perhaps you feel directionless, depressed and unmotivated.

Well, these days you’re in a very big club. Half the planet or more shares your angst and ennui. This crisis has created great emotional turmoil for almost all of us.

Your primary line of inquiry therefore should be, would you feel any different working 9 to 5 than you do right now freelancing? In other words, is it deeply-rooted and career specific?

Or is your burnout more general and temporary? If so, can you somehow jump-start your state of mind? For instance…

Can you reboot your zest for freelancing by creating new, exciting projects?

Can you address your depression with professional medical help or counselling?

Can you stop banging your head against the proverbial brick wall and take a break from making unsuccessful pitches and incorporate new directions into your freelancing brand?

Can you do with a fresh website, or new business cards? These may seem superficial but if you feel uninspired you may also seem that way to your clients. Nobody wants to deal with someone who appears to be out of touch.

Is your social media presence constantly updated and made to look relevant? By making the effort to appear up to date and lively you may well end up feeling that way too.


Go ahead and assess your freelancing lifestyle using the above questions. Again, imagine yourself six months or a year into the future.

Do you see yourself being happier or more productive once we are through the worst of this crisis?

Or can you see no respite to your burnout and no relief from your feelings of depression if everything else remains the same?

If so, then you may indeed need to change and leave freelancing.

For a while? For good? For part time or full time?

Only you can decide.

The takeaway

There is no shame in leaving a party you feel unable to enjoy and experience to its fullest potential.

Likewise, taking a break from freelancing, either full time or part time, for a short period or indefinitely, is a perfectly reasonable decision if you have explored and found wanting your answers to questions and issues like those raised in this column.

A crisis like the one we are currently battling can bring problems to the surface that have long been bubbling below but that you have managed to ignore or work around.

Rather than doing that again, this time, why not use this crisis to fully confront head-on your doubts and struggles, professional and personal, and come to a definitive, pragmatic decision.

Either fully re-commit to freelancing, or else investigate, pursue and implement any available non-freelancing career options.

It only makes sense. And hey, we’ll always be happy to welcome you back!

Posted on August 5, 2020 at 9:42 pm by editor · · Tagged with: , , ,

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  1. Written by Steve Threndyle
    on August 19, 2020 at 2:14 pm
    Reply · Permalink

    These are good ‘gut check’ questions to ask at any period in one’s career. Of course, they’re also affected by personal circumstances but as someone who took a retail job for a short period of time late last year, I’d recommend some PT employment where you come into contact with other people.

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