Should you quit your day job to go freelance? Our checklist

by Leo Wiles
20 June 2014

Should you quit your day job to go freelance? Our checklistAt age 20, I was a syndication officer in the London Bureau of ACP (now Bauer) when I suddenly realised instead of buying and selling text and pictures I wanted to create them. My next step was to go home and tell my husband-to-be that I was about to go freelance – and take a drastic cut in pay to fulfil my dreams of becoming a writer.

Why? Because I knew I would be miserable if I spent my working life in a job that was well paid but unfulfilling.

So ask yourself: do I a) WANT to be a freelance writer or b) NEED to write for my daily crust of bread? If you answered a), you’re not ready.

Working for yourself, launching your name and a new career takes passion and commitment, let alone the pain of pushing through the start-up phase, which has the potential to be lean. You also need to be willing to work through the inevitable patches of self-doubt that plague all creatives.

Here’s my checklist for all those readers who answered b).

1. What’s your plan?

As regular readers will know I believe writing is a craft but freelancing… it’s all business. Which is why you need a business plan to understand:

  • Who’s your target employer: Corporate, Media etc.
  • What’s your product: Yachting, Health, Celebrity, Finance writing?
  • Are there enough clients in this sector?
  • What’s the competition look like?
  • What’s your marketing plan?
  • What are your milestones and have you created your step-by-step map to achieve them I.E. overhauled or created your website, ordered business cards, created list of potential clients to cold-call etc.
  • What will your ultimate freelance success goal look like – so that you’ll know when you’ve arrived?

2. Do you have what it takes?

Time for a skill audit. To go freelance, do you require additional training in running a small business, a writing course, a mentor to help you make the transition?

3. Does your bank manager like you?

If you don’t have three to six months of funds set by to pay the rent and eat your last name better be Murdoch or Packer. At this point it is crucial to understand, and remain solvent, how much money you need to survive. Divide this by the number of hours you are realistically able / prepared to work and you’ll have your point of no return – your minimum acceptable hourly rate (MAHR). From there you will know that you need to earn X which means charging Y per hour and entails having Z clients by… [insert date here].

4. Does your husband / wife understand your need to do this?

Without crucial backing from your nearest and dearest whose affairs are financially and emotionally entangled the road ahead could be incredibly rocky. I’m a firm believer in ignoring emotional vampires, but when starting out it can be incredibly hard to do so when you’ve got someone threatening your mojo at every step.

5. Is the timing right?

Just like becoming a parent there will never be the RIGHT time or enough money to go freelance. You just have to jump off the ledge – but it’s best to avoid June 30 (when big business are all micro examining their budgets) or the holidays (when your potential contacts are beachside, or on the slopes).

6. Does your reputation precede you?

Have you examined your online profile recently? What does it say about you? Does it support your desire to write about, say, surfing for a living? Does your website, Instagram account, FB and blog follow the waves, review boards, talk about the great swell this morning, offer interviews with surfing giants?

7. Can you afford to get set up?

Fortunately setting up a home office can be as easy and low cost as having a reliable phone line, computer, up to date software and optionally a printer/scanner. A dedicated space/study can be a great way to keep your books in order and your mind on the job of ‘going to work’.

8. Have you registered for an ABN?

Until you hit $70K, you won’t need to worry about GST or potentially an accountant – unless you need help putting money away for your super. Or times when you’re sick, want a break or need to pay the tax man down the track. However, registering your business name and applying for an ABN are all good work practices along with setting up a designated account to keep financial track.

9. Do you have a niche?

Before you go freelance, it’s crucial to understand what it is you can offer that’s unique. Is it your writing style a la travel writer Bill Bryson? Or perhaps you’ve studied as a lawyer, nurse or worked as an IT guru and will be bringing this experience to your writing?

10. Have you collected your best bylines?

Pull together examples of any relevant writing you may have had published – no matter if it was online or in print – internal communications newsletter, your blog, the local newspaper etc. show your potential would be employee that you can string a sentence together to tell a story.

11. Do you have an online portfolio or are you getting one?

See our previous blog posts here and here on this one.

12. Are you ready to shout it from the rooftops?

You need to be open to putting yourself out there. This means tweeting, updating your social media profiles, especially LinkedIn, and introducing yourself as a freelance writer. Head to your most relevant network opportunities eg. MEAA drinks, Women in Business, your local Chambers of Commerce breakfast and let them know that you’re a writer looking for work.

Funnily enough this can be one of the hardest stages – you need to fake it till you make it so practice in the mirror “I am a writer” until it rolls off your tongue easily, and you sound like someone your new acquaintance would like to recommend and or hire rather than someone who blushes or can’t keep their eye.

13. Are you well and truly committed?

Everyone starts somewhere, so ask yourself are you more afraid of trying, starting or failing? If you’re risk adverse and have commitments such as a young family you may want to start up freelance writing on the side – but like all low risk the pay off can take longer to reach your goal of quitting your day job.

We’re all scared of failure, which is why it’s best to break your plan down into manageable steps and remember that each time you fail you have an opportunity to learn a lesson that will bring you one step closer to where you ultimately want to be.

If you’ve tried striking out as a freelancer before and failed examine why it didn’t work and what has changed in your life or skills arsenal to ensure that you’re not repeating history.

14. Have you got your pitching hat on?

See our blog posts on this here and here, and begin. Write a list of the top outlets you’d love to work for then email your pitch beginning with the least favourite so that by the time you contact your ultimate platform you’ll sound confidently professional.

15. Do you understand it won’t happen overnight?

Without cuttings it can seem like a numbers game so smile and dial. Read our previous blogs on pitching techniques and negotiating rates – and remember, you’ve just begun one of the most incredibly rewarding vocations of all time – communicating ideas to thousands, potentially millions of people you may never meet and changing their lives.

16. Are you still stuck?

Send your questions in to Ask Us Wednesday on the Rachel’s List’s website, or enrol in a course at a Writer’s Centre. You could also post questions to forums, Twitter and LinkedIn groups – all of these can be a great way for you to ‘meet’ people who are living your dream and have found a way through whichever challenge you may be facing.

If you still recall how you began your journey into freelance writing and would care to share your tips we’d love to hear from you in the comments.

Leo Wiles

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