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Freelance Copywriters need to play the long game

Jonathan Wilcock, Freelance Copywriter, playing the long game

You’ve been a Freelance Copywriter for a few years. Built a decent reputation and a gaggle of lovely clients. Work’s good. Life’s good. Cushty.

Then it all grinds to a halt. You haven’t had a snifflet of a brief in ages.

Get used to it chum, that’s freelancing for you – but it doesn’t have to be.

There are ways you can better stack the odds in your favour.

Two of the biggest errors you’ll probably (me too) make along the way, by my reckoning, are:

1) Complacency – assuming the one or two clients who spoon-feed you 80% of your work will always be there for you. Their company will always be buoyant, they’ll never get made redundant, they’ll never fall in love with a new writer who’ll cream off all the briefs you used to get.

2) Letting old clients drift away – only keeping in touch while the work flows in your direction. Not reminding them that you’re still there, even though they might not need you right at that moment.

The first is all about keeping the funnel topped up – new biz. We all hate it, it’s a slog, but it’s got to be done.

The second is easier to do (you already have a relationship and their contact details), but even easier to let slide. I’m probably as guilty as anyone, but the one thing I make sure I do, at least, is drop old clients an occasional line. Just enough to keep my name floating somewhere in the back of their subconscious; but not so much that I become a pest.

And I’ve just proven to myself that it works. (sfx: Klaxon AROOOOOGA!)

Client X – the CD of a London design agency – gave me half a dozen really nice briefs between October 2017 and October 2018. We had a smooth and enjoyable working relationship. All was well.

I dropped him (and all my other contacts) a Christmas 2018 email:

Barry the Brown-nosed Reindeer would like to say:

“Thanks for everything in 2018. X, you truly are the superest-smashingest-greatest, most bloody marvelous geezer bloke in the world, ever. You’re even better than the rutting season or a bunch of carrots”.

He’d also like to say:

“Jonathan is breaking up for Christmas on December the *twentyoneth and re-opening the ideas workshop on January the *twoth”.

Happy Christmas and lots of love.

Hope to bump antlers in 2019.

Barry and Jonathan x

*Reindeers are great with compliments, but rubbish with numbers.

Then I sent him an email at the end of January 2019, to let him know my upcoming holiday plans:


Just so’s you know, I’m off to India at the end of next month and won’t be checking emails, social media or myself in a mirror for a while.

If you need to get hold of me before 25th Feb, you know where I am.

After that, I’ll be somewhere in the Himalayas until 17th March.

Then, once my head’s caught up with the rest of me, I’ll be back to my usual copywriting tricks.



Then he got my Christmas 2019 email:


So you’ll find me:

– Tying up loose ends until 20.12.19
– Staring into space until 06.01.20
– Fighting the good fight from 07.01.20

However, if the world’s in peril and you need a copywriting superhero, just holler.

In the meantime…



Then over the next months and years, he got a rate increase email, a ‘hope you’re OK’ lockdown email, a 2020 Christmas email, another rate increase email, Christmas 2021 email, Christmas 2022 email and finally, in January 2023, I sent an email with its sleeves rolled up, that started off with:

Hi X,

How’s tricks? It’s been a while.

Not that I’m sitting here counting or anything, but…

In the 1540 days, 2 hours and 7 minutes since we last worked together, I’ve grown a little bit older, a little bit wiser…

So, all in all, he’d received 10 memory-jogging emails in a period of 49 months.

Then, Wouldya-Adam-&-Eve-It, he called me a couple of weeks ago to discuss three (THREE) (3) possible briefs. I’ve already cracked the first two. Yet to see if the third materialises, but if not, you can bet your Sylvanian Families collection I’ll be keeping in touch.

Long game. Persistence. Sheer bloody-mindedness. Whatever you call it, sometimes it pays off.

So, don’t give up my friend. Keep plugging away, be consistent, be playful, be yourself and enjoy the ride.

And if you’re up for it, there are plenty more tips here to rescue yourself from the freelance doldrums.

Wishing you many joyful years of creative goodness.

Love and patience.

Jonathan x

Jonathan Wilcock (that’s me) is a Senior Freelance Copywriter.
You can drop me a line here, or email