This week’s Outside Perspective Community Edition is a takeover by Stephanie Ressort - Thanks for giving me a little bit of a break from writing emails, so I can be parenting this week.
My name is Stephanie Ressort, and I am a freelance advertising strategist, writer and recovering theatre reviewer (it has been over 3 years since my last review).
I’ve been a member of the Outside Perspective community since its inception. Does that mean I get a badge? Or a mug? Or £1million? (if you don’t ask…) Which reminds me, these fabulous OP mugs are available here (I get bonus points for pushing the merch, right?)
I’ve been working in the frustrating, ridiculous, turbulent, varied and stimulating industry that is advertising for longer than I care to admit, and I’ve been a freelance advertising strategy consultant for over 9 of those years. I’ve worked directly for marketing teams, media agencies, creative agencies, media sales teams, and consultancies. I’ve developed brand and campaign strategies, created tailored training courses, written white papers and awards entries. The list could go on, but there is a word limit.
In a time that celebrates the niche specialist, I am doing everything wrong by being a scattergun generalist.
I recently returned from a week of editing in Leicester. I often refer to it as a holiday, simply because it is my annual attempt to take a break from the niggling demands of daily life and gift myself time to do deep work on my messy beast of a novel.
This was the 10 years anniversary of going on writing retreats with a talented group of writers I originally met on an Arvon course in 2015. We are a mix of published and unpublished writers who have each other’s backs. We celebrate each other’s writing victories and support each other through the stresses of word wrestling and misbehaving characters. Don’t get me started on saggy middles. So, my Demon Beaters group (as we call ourselves, named for the first course we met on) are a lot like the Outside Perspective community. Both work on the principle that we all benefit from lifting each other up.
Philippa, one of my fellow writers and a genuinely magical human, gifted me a copy of Chuck Wendig’s “Gentle Writing Advice” , a funny and generous book perfect for word-wranglers in a turbulent world. The subtitle “How to be a writer without destroying yourself” says it all. The following paragraph resonated with me as both a writer and a freelancer:
“When I didn’t have a job? When I was scraping together pennies and selling plasma for coin, do you think I was at my most productive? Spoiler warnings: I was not. Starvation is not a good condition for making art. Being worried about where your next paycheck is going to come from does not make it easy to effortlessly create art. Half the time I’d want to spend writing I’d instead spend just looking for jobs. It was easier to write when I was working jobs, despite jobs taking up the lion’s share of time.”
There are so many different motivations for becoming a freelancer, but the one unifying principle should be that when we are working, we should be earning enough to support ourselves, develop ourselves and cover the lulls. Things are broken if you are working and still earning less than you need to cover your costs of existing. The market right now is hideous, and it can feel like a race to the bottom, with freelancers often forced to accept low rates, just to slow the financial decline.
The problem is, accepting underpaying clients is setting yourself up for burnout and failure. How are you supposed to do your best work, if you have escalating debts and are worried about paying the bills? Undervaluing yourself will not result in a more stable work life, quite the opposite. You will be exhausting yourself by working while still having money worries.
Sadly, this is the natural result of a systemic undervaluing of creative workers (and yes, my lovely advertising colleagues, you are creative, whether the word is in your job title or not). Even within the most commercially driven arm of the creative world, human creativity is being undervalued. And myriads of alarmist articles about AI coming for creative jobs is escalating that. Some might say, deliberately, after all who benefits if we accept less money because we’ve been told we can be replaced by software? Cynical? Moi?
This recent article here gives a more balanced view on AI and creative jobs. It highlights something that is becoming very clear, education systems need a major overhaul, as does the upskilling and training of the workforce.
So yes, I’m sorry to say this upskilling is yet another time and financial cost for freelancers to absorb. If you are not reflecting that in your rates, I hope you are at least buying lottery tickets or have a wealthy partner.
Chronic underfunding impacts both creative individuals and creative industries. This was highlighted in a recent article by Lyn Gardner for The Stage:
“Starved of investment, British theatre has been cut to the bone. On the fringe, you can see the bones and you can see them crumbling in front of your eyes.”
The article is available here, although you will need to create a (free) account to access the full piece.
Why should we, in the advertising industry, care about the decimation of fringe theatre in the UK? Because it is the canary in the mine. The fringe is the river feeding the ocean of mainstream media.
In July I was lucky enough to attend the Mad/Fest Festival in the Truman Brewery. A talk by Margaret Heffernan entitled “Embracing Uncertainty: How writers, musicians and artists thrive in an unpredictable world” particularly resonated with me.
She covered more than I can share in this newsletter, but one of my key take-outs was that those who made the time to do proper deep creative work, were the ones that could most clearly predict the future. That the arts don’t create trends, they anticipate them. As a strategist, my time as a theatre reviewer in the fringiest of fringe theatres, was invaluable in helping me identify the key cultural and deeply human concerns that would be dominating conversations in the years ahead.
If the only people who can afford to do this deep creative work, come from a dwindling pool of financially comfortable people who can afford to subsidise the industry, we will all be the poorer for it. Our seers will illuminate only the narrowest passageway to a more limited collective future. It has long been established that diversity fuels broader outlooks and greater collective resilience. We need that now more than ever.
This is why I’ve been a long-time supporter of the brilliant grassroots charity Arts Emergency. It is energising to work with people trying to fix the problems instead of complaining about them. You can find out more about what they do here. Registration is open to become one of their 2026 mentors, should you have the time to spare. I’ve mentored several young people over the years, and it is soul fuel. But I digress.
In this rather brilliant piece here Margaret Heffernan (yes I went down a fangirl google rabbit hole) speaks eloquently about how we better navigate uncertainty. “Adaptability, not control, is the critical dynamic for surviving uncertainty.”
But it is impossible to adapt if you are exhausted and in constant survival mode. While it is easier said than done, making time to think is crucial. To effectively adapt, we need to identify the paths that are open to us and make smart choices (I could do a whole newsletter on the damage done by “could” trumping “should” in modern society, but I’m not sure I’ll be invited back). There are always choices, and if we don’t make them, they will be made for us.
I want to sign off with a message to all those who are struggling, don’t let the ugliest freelance market I’ve experienced redefine your worth. I hope you succeed in adapting and thriving.
Thanks to Steph for this takeover - and giving Matthew a break! If you’re keen to takeover the Community Edition (and that’s one of the main reasons we started the substack, to create opportunities for our members to share their thinking), drop me a note.
» Women’s football is reforming the visual culture of sport (thanks Gemma)
» Comms advice for startups (thanks Rob)
» ITV’s new culture newsletter - Pop Theory
» The evolution of five iconic icons from Adobe (thanks Nick)
» Cultural insight is not the same as trends
» Nine years of repeating New Yorkers
Briefs discovered and curated from across the stratosphere.
Promote your brief - or tell us if you’ve found work via the project.
freelance Comms Strategist with pharma experience (US)
https://outsideperspective.co/gigs/20250815-spcshp.html
freelance strategists with B2B (tech) marketing experience (UK)
https://outsideperspective.co/gigs/20250815-dna.html
freelance Senior Health Strategist (Canada)
https://outsideperspective.co/gigs/20250815-dentsu.html
freelance strategists with exp in digital transformation and cx (CA)
https://outsideperspective.co/gigs/20250814-nurun.html
Freelance Strategist (EU)
https://outsideperspective.co/gigs/20250814-droga5.html
Freelance Brand Strategist with retail exp (Manchester,UK)
https://outsideperspective.co/gigs/20250814-brand-strategy.html
Freelance Senior Creative Strategist (Manchester,UK)
https://outsideperspective.co/gigs/20250814-become.html
Marketing Strategist (AU)
https://outsideperspective.co/gigs/20250813-canwetalk.html
freelance creative strategist familiar with Egyptian and GCC markets (Remote)
https://outsideperspective.co/gigs/20250813-arabyads.html
Freelance Strategists with UK market exp (Remote,UK)
https://outsideperspective.co/gigs/20250811-wyw.html
freelance cultural / brand / creative strategist (uk,es,nl,pl)
https://outsideperspective.co/gigs/20250811-pepsico.html
Freelance Social Strategist (Dubai)
https://outsideperspective.co/gigs/20250811-create.html
If you’re a business working with freelance strategists, Outside Perspective can now host your alumni. Keep your best freelancers close, reducing costs and saving time - plus share your briefs to our entire network for no additional cost.
If you’re keen to know how we can support your bench … drop me a note.
That’s all for this week.
mk✌️
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