ASK US WEDNESDAY: “Should I leave my day job?”

by Rachel Smith
15 August 2018

I’m working in a job I loathe, that pays the bills – and I write on the side. I’ve been working on a book for a few years, and I pitch stories to editors several times a week. Some are encouraging but I’ve had nothing picked up yet. I have written a few digital pieces (and been paid very little), so I have some work to show. I’ve been told I’m a great writer and I know if I had time to focus on it I could make it work. Someone suggested I check out your site and I thought I’d ask your advice. Should I leave my day job? When do you know it’s time to take the chance? K

This is really the million dollar question for any wannabe freelancer who’s had this choice to make. Our checklist on this topic has some great questions for anyone thinking of ditching their 9-5 to go freelance. But in short, you should only leave your day job when…

… you have a 6-month buffer of savings.

Freelancing is tough, especially when you’re starting out and if you have no contacts. So you definitely don’t want to strike out as a freelancer without any moolah in the bank. Save, save, save so when you’re ready to take the leap, you know you’ve got some breathing room to pitch and chase work – and won’t be tempted to take badly paid gigs because you’re desperate.

… you have 5-10 clippings of paid work

You can’t actually join Rachel’s List unless you’re already making a living in the industry or have a HEAP of paid experience, so it’s great to keep building that up on the side. While some editors will commission you on a good pitch alone, many will want to see previous examples of work to ensure you can do the job so the more clippings you have, the better.

… you have some solid contacts

These might be from a writing class, a writing course you’ve done, or a couple of clients or editors you’ve formed relationships with. If you don’t have any of the above, you’re striking out cold. That’s hard yakka. Start building relationships, joining freelancing groups on FB and making contacts while you’re still in the security of your current job. Make it a priority.

… you have an amazing website

Now is the time, while you’re in full-time, paid work, to get your website off the ground. If you can throw some money at it, do it. It’s the first thing clients and editors will look at and it should be beautifully written, showcase what you can do and previous examples of your work, and offer a variety of ways to contact you. Similarly, pick 1-2 social platforms and start building followers and interacting with editors, writers and other creatives.

… you have a regular gig

You don’t say where you’re working, but if there’s a chance for you to do some writing for one or more departments – even if it’s not part of your day job – try to make that happen. It’s great experience, it could lead to referrals or a freelance gig outside your job – or even a gig at the same company after you leave. And you always want to leave a job with a regular gig in the bag so you know some of your bills are taken care of while you hustle for more work.

I hope that helps!

Listers – did you have all of the above in place when you left your day job?

Rachel Smith

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