Seven lessons in seven months of freelance | Cassidy Parker
September marks seven months of freelance. Seven months of being shown up against a mirror of myself in ways unprecedented and unnerving.
Cassidy Parker, musings, writing, freelance, lessons,
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Seven lessons in seven months of freelance

September marks seven months of freelance. Seven months of buying groceries with the pensioners at 11am on a Wednesday, of riding the waves of desperate anxiety and joyous I-got-a-gig relief and, more than anything, of being shown up against a mirror of myself in ways unprecedented and unnerving. (Nothing, I don’t think, has ever cast such a fierce light on my ambitions and inhibitions.) As I continue to navigate self-employment, here are some of the lessons I’ve picked up along the way.

Quiet nights in Cascais. Portugal, August 2017

You’re always with yourself

I remember sitting on the side of the road in La Paz once. I’d spent a few days hiking around the area and it was my last day in the city before crossing the border into Peru. It was late afternoon, my feet were in the gutter, my daypack between them and my energy was nil. I’d battled what I later identified as my first serious bout of depression a few months before and hadn’t managed to shake it just because I was on a Grand South American Adventure. You’re always with yourself, I remember thinking. Geography, circumstance, they don’t change a thing. No matter where you are, there you are.

The same applies to freelance. While I’m light years away from the feelings described above, and am happier in my work than I’ve ever been, I’m still with myself. Self-employment hasn’t cured me of my creative insecurities, my tireless self-doubt and my eternal procrastinations. There are signs of improvement, but really, if you’re not already making your creative work a priority (Cassidy, I’m talking to you), freelance isn’t going to help you.


The streets of La Paz. Bolivia, February 2013

Say yes to everything 

I’ve learnt to say yes. Yes to work I’m trying move away from. Yes to work I don’t really have time for. Yes to anything I’m capable of doing – or of learning to do. I’ve learnt that accepting jobs I wasn’t initially interested in can lead to offers of spine-tingling delight and that work doesn’t always manifest when I think it will. In two weeks’ time, when things are quieter and the job comes in, I’m always glad I said yes.

(There’s also something more cosmic about saying yes. That universe, it’s listening.)


Saying yes. Vietnam, August 2010

Loneliness is like dehydration

Once you realise you’re feeling it, it’s too late. If the week looks quiet, I’ve learnt to get out the house on Tuesday, rather than Thursday. A simple coffee shop excursion usually does the trick, so much the better if I convince a fellow freelance companion to join me. Not putting these steps in place has me parched for company come the end of the week, even if my evenings have been social. Pre-empt the loneliness: drink up the pleasure of others.


Guincho beach. Portugal, 2017

Hone your craft 

My dad – a self-employed musician for the last 60 years of his almost-80-years-and-counting life – gave me a piece of advice before I resigned: “Hone your craft,” he said. “The last thing you want is for someone to give you a call for a gig you’re interested in and you haven’t picked up your trumpet in months.” I’ve neglected my blog for the last little while and, after referring a potential new client to my site recently (with the most recent blog written in May), felt the shame at not having picked up my metaphorical trumpet. Practise what you sell; practise what you love.

Get out of town 

I spent two weeks in Portugal in August, on a holiday that tasted of espetada and sangria, felt like sticky sun cream-slathered skin, and sounded like late-night laughter. Travelling so soon into freelance – to Europe, no less, and in the height of summer – felt like the most financially irresponsible thing I could have done. But it was an opportunity I couldn’t refuse, a chance to see people I love in a place new to all of us. It was the stuff of life. And it was encouraging to learn that not only was I capable of taking a holiday without constantly thinking about work, but that work would be waiting for me when I returned. A two-week break does not the end of a career make.


Lazy lagoons on scorching days. Portugal, August 2017

Something always happens 

The financial unpredictability is real. I’ve had days – weeks – of sitting and fretting. Sit. Fret. Sit some more. Fret some more. (Yes, it’s as counterproductive as it sounds.) But, to quote my father yet again: “something always happens”. My phone rings, an email comes in. A referral, a recommendation. Of course, Something Always Happens goes hand-in-hand with The Hustle: you’ve got to combine your faith in the former with your persistence in the latter.

Never underestimate the bonding you can do with your cat


Exhibit A

9 Comments
  • Valkyrie Philip
    Posted at 12:58h, 19 September Reply

    Wonderful Cass! Don’t stop here!!

  • Bruce Cassidy
    Posted at 13:18h, 19 September Reply

    Brilliant Cass. Lessons well absorbed and well transferred to those who have eyes to see – and read – and absorb – and practice… Keep reporting on your journey. Inspiring!

  • Alex Hill
    Posted at 13:27h, 19 September Reply

    I love your posts. Puts so much into perspective.

  • Zanatoa
    Posted at 13:33h, 19 September Reply

    Sweet Cass, keep pushing on, your magic expands in your movement. Smiles and sparkles

  • Kate Turkington
    Posted at 14:04h, 19 September Reply

    So enjoyed listening to you…

  • Cilla Dowse
    Posted at 14:59h, 19 September Reply

    Just love reading your words …. Keep them coming!

  • Eddie
    Posted at 15:43h, 19 September Reply

    Love it! xx

  • Tara Turkington
    Posted at 16:17h, 19 September Reply

    Some great lessons here. Really enjoyed reading this x

  • Craig Ginsberg
    Posted at 10:02h, 20 September Reply

    Lovely Cass
    Your eloquence delights the senses and expands visualization in such a succinct and profound way. Love you

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