How to start freelancing while juggling a day job

by Leo Wiles
13 March 2015

Leaving work behind to follow your destiny of becoming a freelance writer isn’t for the faint hearted. You need perseverance and a good dose of pig-headedness.

My journey began at 21. I was stuck at a desk, fed up with syndicating other people’s copy and pix in the London bureau of ACP (now Bauer). I began approaching editors who were buying overseas stories and offered myself as a UK stringer. When that didn’t work, I pitched specific interviews and angles. Within six months my evenings, weekends and lunch hours were increasingly filled with commissions. Even when I changed jobs and became a cadet on a national newspaper, largely thanks to those cuts, I still wrote around my position until two years later I could finally emerge from my chrysalis as a freelance writer.

Was it exhausting? Yes – not only due to juggling the various commitments, but also dealing with the emotional fallout of family and friends. It took my engineer husband years to get his head around the fact I had thrown away a good salaried job and the perks that went with it for the insecurities and isolation of freelancing. But there it was. I’d fallen in love with words and there was no turning back.

Everyone’s journey is different but nobody I know was handed a successful freelance career. We all earned it – and if you’re on the cusp of leaping, here are my tips on how to get going (and stay the course).

Make time. Your freelancing needs to be a priority – not something you do occasionally when you can shoehorn in it. So when the kids are finally down, turn off the TV and work. Swap your hobbies for your writing. Stop boozing on Saturday nights and wasting your Sundays in recovery. These are your writing hours – protect them.

Be realistic. People have never heard of you, and without a portfolio, may never have read your work. So get published. Write for your local paper or better still, a local charity. Bill them then donate your fee back so that at tax time it goes against your earnings.

Reach out. Do you work for a company where you could begin contributing to their external or internal communications? Start. And, look around when you’re not at work. Who do you know with a small business or professional website who needs regular content? Offer to do it for mates rates to get the ball rolling.

Just write. Start your own blog to get into the daily routine of writing. Not for the word count, but to learn the discipline of writing when you don’t want to (and learning to turn a stale subject around hundreds of times).

Be proactive. Setting goals will help you reach them. Will you write a pitch a day, contact three editors a week, aim to land a new magazine a month or have a regular corporate contract by the end of the year? Or perhaps your goal is ‘When I have six regular gigs and enough rainy day money in the bank I’m resigning’. It’s those goals that’ll catapult you into the freelance world, eventually.

Tell everyone. Let people know you’re a writer looking for new clients. It’s amazing how much work you can pick up through word of mouth.

Showcase your work. Emailing word documents or even PDFs of your clips isn’t going to cut it anymore. You need to present yourself in a touch of a button way. That’s why having an online portfolio of some sort is essential.

Learn to balance. If you have financial commitments such as a family and mortgage it can make sense to take up a bread and butter job two to three days per week and devote the rest to writing. Take heart: William Faulkner, Bram Stoker, Lewis Carroll, Virginia Woolf and T.S. Eliot all wrote some of their best works while holding down day jobs. And if you start asking yourself if all this extra work and sacrifice is worth it? Well, it is. As Confucius said; “Choose a job you love, and you will never have to work a day in your life.”

How did you make the transition into freelancing? Please share your pearls of wisdom in the comments below!

Leo Wiles

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