The Born Freelancer on Going from 9-to-5 to Freelance During a Crisis

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.


Extreme conditions bring about extreme changes.

In many cases, it is the only way to survive.

Today I’d like to talk about how the current crisis may be a good time in which to reconsider your career options going forward.

Going freelance

So perhaps you find yourself out of work from your 9 to 5 routine due to the pandemic.

Or perhaps you are in limbo on CERB while you wait to see if your old 9 to 5 job will still exist.

Maybe you are working from home and you are thinking that you kind of like it.

Or maybe you are still working in your 9 to 5 but hating it more and more and wondering why you stick with it.

Have you considered going freelance?


For many of us it’s about control.

Control over when you work.

As long as you produce results by the agreed-upon deadline you can work whenever you want. And this means, of course, you can work for multiple employers simultaneously, something you could never do working 9 to 5. How much you make will be up to you.

Control over where you work.

Usually this will mean working from home. But pre-Covid (and undoubtably post-Covid too) you could work wherever – the library, a coffee shop, or on a nice park bench in the sunshine.

Control over for whom you work.

In practical terms, you become your own boss. Of course, your contracted work will be for others but it will be under terms you have mutually agreed upon. If you don’t like them, you don’t have to work for them. If they turn out to be sociopaths, you never have to work for them again.

Control over exactly what work you do.

You want to be a sports journalist? No more “Would you mind also doubling for Kinney at reception until he’s back?” As a freelancer you will choose a specialty (one you love to pursue) and that will be what it is you do.

So how do I go freelance?

First, a self-evaluation.

What will motivate you to succeed on your own?

If you are stuck in administration and hate it, there’s no point in pursuing freelance administration. But if you love sports with a passion and are knowledgeable and can write, it could make sense to pursue, say, freelance sports journalism.

What experience do you have that would be helpful?

If you have already had, for example, experience in writing it makes sense to pursue freelance writing. You must decide what it is you wish to do and then focus your efforts on marketing yourself as the go-to-person in your field. A thorough examination of this site will offer you much useful advice.

What skill set upgrades will you need?

You can always benefit from skill upgrades via online coaching or (as restrictions continue to loosen) in-class instruction. Look to community colleges, small business government programs, accredited industry specialists, professional guilds like the CFG and even public libraries.

In addition to fine-tuning your primary creative skill sets, you must also learn how to market yourself. A lockdown is an excellent time in which to upgrade your skills.

What holes in the marketplace could you fill?

Perhaps your 9 to 5 position gave you insights into what creatively really needs to be done. Or what could be done if only there were adequate resources dedicated to hiring someone to do it. Or perhaps a study of your marketplace has shown you where your particular area of creative expertise appears under-represented.

It’s one thing to have the desire to do something. It’s another to find actual jobs in which you can do it. You need both to successfully launch your freelancing career.

What contacts do you already have?

Can any previous (or current) employers help get you started? Would they consider hiring you back (with a renegotiated contract that benefits both of you)? If so, you must show your former employer why it is to their advantage to hire you back as a self-employed contractor. Hint: appeal to their avarice.

Also, think about all your external professional contacts. All the people in your line of work you ever met or talked to over the years. Organize a network inventory and start networking! Contact them and see what freelancing opportunities might exist with them.

At the very least you will gain further insights into what you are trying to achieve. At most, you may win a few small first contracts. From these can grow a sustainable  freelance career.

Can I take the risk?

Freelancing takes a certain kind of individual. A real self-starter. It’s not for the faint-hearted. Let’s look further.


Any savings to help cushion your transition would be useful. Of course, if you’re young and single, having no savings shouldn’t stop you. You will need some initial cash for start up expenses like a website and so on. Not to mention just living.

Perhaps you have family from whom you can borrow? Or a flashy car that could be converted to cash. If you are sincere about going freelance, you will find the initial cash with which to do so. You may need to make some significant sacrifices. And if you aren’t prepared to do so, you should re-examine your commitment.

Supportive family and partners.

If you have family or a partner who can support you financially and/or emotionally during your transition then you have it made. You will need to communicate with them closely, however, and set specific goals and deadlines which they can observe and help you achieve.

If said family or partner are not able or willing to help you financially and/or emotionally perhaps you have not made clear to them your vision of where you could be in a few years going freelance. In the end, freelancing is not just a career choice. It is a lifestyle. If you do not have immediate family or partner endorsement you may need to reconsider your plans.

Consider also a freelancing partnership with a family member, significant other or trusted friend or work colleague. Many episodic television shows, for example, are written by creative collaborators. If you both want to go freelance, why not try it together? Work up some spec scripts and submit them to guild-approved agents. You’ll never know if you can succeed until you try.


If you already have health issues, going freelance may aggravate them. (On the other hand, if you are stressed out because you hate your job going freelance could very likely return you to good health.) You will only make money when you are well. You will not have paid sick days.

And while age should never ever stop you from starting over and pursuing your true passion, if your health and stamina are problematic you might need to re-examine how to go about going freelance – for example, trying it out part-time to begin.

The takeaway

Going freelance can be very scary and fraught with great risk.

But if the current crisis has taught us anything, it is that life can be very scary and fraught with great risk.

For those of us who choose freelancing, the advantages are numerous and overwhelmingly positive.

Indeed, they are more than a match for the scariness and risk.

So, go on, ask yourself… Do I have what it takes to go freelance?

If the answer is a resounding yes, there’s no better excuse than a crisis to take the plunge.


Posted on June 17, 2020 at 9:59 pm by editor · · Tagged with: , , ,

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