The Questions You Need To Ask Yourself Before Going Freelance

Freelancing is both a desirable way to work and a totally possible career path. But, like anything, it might not be right for everyone – for some, it’s pretty damn great, but others find the rollercoaster of uncertainty stressful. Here’s how to tell if you’d swipe right for freelancing.

Freelancing can seem like an exclusive world only a brave few get to experience, but that’s not the case. A study commissioned by Upwork found that one in three Australians now freelance in some capacity and that the majority of freelancers are starting by choice.

Why the high proportion? They’re opting out of a traditional 9-to-5 lifestyle in exchange for more flexibility and work-life balance. They want to be their own boss, and work from wherever, whenever.

But before you hand in your resignation, ask yourself these six questions to determine if the freelancing lifestyle really is right for you.

#1 Does uncertainty scare you?  


Most people wouldn’t consider freelancing because there is no guaranteed income flowing into your bank account to help pay off the mortgage and fund annual holidays. The future is unknown, mainly in the financial sense, and there are plenty of variables that make any kind of forecast planning a near-impossible task.

That being said, the feeling when you nab a new client or lock in an exciting project is borderline euphoric. Freelancing is rewarding if you thrive on challenges – but if the thought of not having a steady routine makes you want to curl up into a ball and hyperventilate, then you might want to reconsider.

#2 Do you give up easily?

If your reflex reaction is to retreat as soon as you encounter any hurdles, then abort Operation Freelance immediately. Freelancing involves a lot of self-motivation and is about continually picking yourself up after every obstacle; you’ll need more than your average dose of resilience to stay determined and focused on the end game.

There will be days of interminable drought spent constantly refreshing your inbox; times where existing and potential clients may not return your calls or emails; and moments when you may begin to wonder if you really have what it takes to be a lone wolf.

Freelancing is not for the faint-hearted and requires the tenacity to bounce back after every setback, time and time again.

#3 Are you self-disciplined?

It’s not necessary to be a rigid disciplinarian but freelancing does require the capacity to talk yourself out of bed every morning, because bed.

You, and you only, are accountable for your productivity and motivation levels – there is no intimidating boss to give you the evil-eye as you rush into work late and no end-of-year bonus dependent on your annual performance review.

Even though freelancing allows more flexibility, you still need to be organized enough to stick to project deadlines, especially as you may be dealing with several projects on the go at once (let’s think best-case scenario here, guys).

What freelancing also affords is the ability to work according to your own strengths, i.e. working in the evenings if you’re not a sunrise yoga kind of person. However, if you don’t think that you’ll be able to coax yourself off social media, or climb out of a cat-video clickhole, then you could be in trouble.

#4 Are you okay with your own company? 


Are you a rampant social butterfly? Do you live for the water-cooler chats at work? If so, then freelancing may come as a mammoth shock to your system. Freelancing is a solitary pursuit and you’ll need to be comfortable with your own company, or learn to be comfortable with your own company, pronto.

There are other ways to meet your social interaction quota and avoid resorting to naming your cushion ‘Roberta’: take your laptop to the café down the road (that, most importantly, has reliable Wi-Fi); pay to join a co-share space or hub; or attend networking meetings with other freelancers or people in your industry.

But if the social aspect of work is what gets you up in the morning, then really think about whether you’d be happy, just you and your mate, Roberta.

#5 Do you have a contingency plan – or any plan?

Freelancing, particularly at the beginning, can be difficult and a slow burn as you get your business underway and build a dependable client base. Do you have a contingency in place in the scenario that clients don’t come knocking on your door straight away?

That might mean you have a pool of money saved up to tide you over for a little while, or even a partner who can help support you while you get on your feet. It’s worth having a plan in place, along with a list of potential clients to contact and a firm idea of the services or value that you will be providing your clients. Freelancing is a marathon, not a race – so assess your situation carefully and make it work for you in the long term.

#6 Are you confident in your skills?

If you didn’t immediately shout ‘YES!’ then you need to ask yourself why, because freelancing is not the place to exercise modesty.

Clients will expect that you have the relevant skills to take charge of a project and execute it without any handholding. But this requires you to be confident in your skillset and communicate that confidence – be assertive in what you can offer because you are going to need to sell, sell, sell. But of course, you shouldn’t lie about your knowledge and experience.

If there is anything that you think needs improvement, take the time to invest in updating or consolidating your knowledge base – just don’t downplay your expertise and sell yourself short.

As desirable as freelancing sounds, it’s a lifestyle that’ll suit certain personalities but feel uncomfortable for others. If you’ve answered these questions and the freelancing lifestyle still appeals to you – there’s one more question left to ask: what are you waiting for?

Camha is a freelance editor and writer currently based in Perth. She is a wannabe word nerd, travel-addict and coffee enthusiast, and thinks that life is just one big Seinfeld episode (where Elaine is her BFF). She has written for Broadsheet, AWOL, The Big Bus and the Huffington Post Australia, and tweets at @curatedbycammi