Working Theories with Sam Diss
When did we stop asking questions? From running magazines to creative strategy – how Sam Diss turned asking questions into a career.
Tell us who you are:
My name is Sam and I’m a writer and strategist, born and based in East London. Everyone kinda knows what writing is, although the difference between good writing and bad writing… is another story. However, strategy is one people never seem to understand. I didn’t understand it myself when I first started. I didn’t realise the work I’d been doing for years, aka the constituent parts of a creative practise that might politely be described as “wearing many hats” or less politely as “doing all the work yourself” made up the role of ‘strategist’. Before I went freelance, saw a job description, and thought: Hold on. I know that one.
I don’t come from a writing background or a creative background, but maybe I do come from a strategy background: A place where you can’t really throw money at a problem so you have to be smart and find other ways to get things done. I didn’t get to go to university so I lied about my age and got an internship at VICE when I was 16, telling the person on the front desk that so-and-so had told me to come in, knowing they were on maternity leave and thus unlikely to be disturbed to fact-check what was actually a blatant lie. It worked. Everyone needs a way into the industry and sometimes you need to jump a barrier. Lying — nobody got hurt! — is strategy, too.
What gets me up in the morning: My Sleep Cycle app, my cats, Haggis and Chips, screaming at our bedroom door, my beautiful girlfriend Steffi, and the thought that today might be the day that we get some properly good work out the door.
What’s a working theory you hold right now about the industry, culture, or creativity?
My working theory is that everyone is scared to ask questions. We live in a society that is increasingly isolated : from the world at large, from each other and from ourselves. Being more inquisitive not only brings us closer to people but helps us do better work, too. Owing to my background as a writer and interviewer of many people — famous or otherwise — I love to integrate that skillset into my work: Asking loads of questions; obvious questions, open questions, diverting questions to put someone off balance, deep questions to get to the root of a feeling behind an action — helps me make develop ideas and make decisions.
But, and I don’t know if this is simply my own anecdotal misfortune but, it appears that a lot of people don’t really like to ask questions for fear of showing they don’t know the answer to something. If I get a brief that references, I don’t know, the bikelife culture of Merseyside or like, two-step cleansing routines for tween girls, I won’t just pretend I know stuff and surreptitiously Google it, drenched in sweat for worry that someone might think I don’t know the benefit of an oil-based cleanser. I go out and ask people. I ask people who know so then I’ll know, too. I love not knowing stuff because I know that it’s halfway to me learning something new.
That old axiom is true: Your fear of looking stupid is holding you back.
What’s a belief or assumption in your field that you think is overdue for a rethink?
That social strategists need to care about about paid-social. I’m sorry, but that which is once a dark-art is now DOA. I’m willing to go on record here: I think paid-ads on social are, by and large, like shooting your cash down through a sewer grate.
For certain markets, I get it. But if you’re putting money behind “awareness” plays or, god forbid, content instead of investing your time and money into making something actually good, then I’ve got a lovely chocolate kettle indoors that’s got your name written all over it.
You can’t pay someone to like you. I feel like we should’ve worked that out by now.
What’s your favourite dumb thing you’ve seen on the internet recently?
Big fan of “Hot Cork Time” on TikTok which is not a compendium of absolute rides from the south of Ireland but a load of very satisfying footage of people moulding what looks like molten Dijon mustard to create cork insoles for shoes. Sometimes a man just needs to learn how a shoe is made, you know?
What are your absolute go-to cultural resources?
Newsletters: After School by Casey Lewis, Link in Bio by Rachel Karten, Story Club by George Saunders
Magazines: I’m a proper magazine man — I spent a decade living, breathing, and making mags — but the state of them right now is abysmal. It’s all pretentious shite propped up by D2C diet alcopop brands. The only exception: New York magazine. Simply the best.
Podcasts: Sweat Equity; a very bro-y strategy podcast that, if you can stomach the presenters’ vibe, has lots to nab from, The Big Picture; because I cannot stop listening to people talking about films, and The English Disease; because I made it: It’s a six-part audio documentary series about the legacy of football hooliganism on Britain, its working class, and on me in particular. The Guardian called it one of the ten best shows of 2024 and it recently won Podcast of the Year at the Sports Journalism Awards, which was nice.
Books: Currently reading Graydon Carter’s autobiography (sadly, it’s just an old man listing names of once glamorous dead people instead of editorial insight into one of the great names of modern publishing). That’s inspiring me to do better. Next up is Lonesome Dove by Larry “he wrote Brokeback Mountain, if you care” McMurtrey. I love cowboy stories — they inspire me to get off my laptop and touch grass.
YouTube: My two obsessions right now — the “trumpet meditations” series of multiinstrumentalist Coulou because it is the finest work music ever made, and Clare Saffitz’s Clare Recreates series where the prized pastry chef tries to remake childhood favourites. Still waiting on part two of the Kinder Bueno video, Clare! Ready when you are!
What part of your practice do people most often misunderstand?
Strategy is a lot of talking to people in rooms; it’s not Gant charts or presentation decks. It’s articulating an idea and making people believe you.
What’s a cultural shift brands haven’t fully understood yet?
That Gen Z-and-younger don’t have a short attention span, they’re just sick of boring content. Have you SEEN how long their podcasts are? They’re the length of Killers of the Flower Moon.
Which project, person or moment has most shaped your approach to work?
Can I be inspired by myself? I’m going to say I can: Creating the magazine MUNDIAL changed my life and also created the “football-lifestyle”/football-meets-culture niche that dominates everything these days. It shaped me by telling me to trust my gut and that, if you build good things you care about, they will resonate with people.
Who do you admire in your space, and why?
I love the work of Rachel Karten; whose newsletter Link In Bio I recommended above. She’s a strategist but works in a different market to me, I’m more sports and she’s more beauty and wellness, but her clear-eyed writing about what makes brands work has got me through some real dismal times.
What’s the biggest risk you’ve taken in work—and what did it teach you?
Quitting my job to work full-time on a magazine that “industry insiders” snarked about and said wouldn’t last two issues. It taught me that people are scared of new things and like to criticise that which they don’t understand. I’ve always tried to keep an open mind after that — plus you look like a bellend if/when you’re wrong.
What’s a brand or cultural moment you keep thinking about lately?
The resurrection of GANT. From dadcore to Six Nations core to Aime Leon Dore ripoffs to some of the most inspiring brand social I’ve seen in ages. Who saw that coming? (Still not gonna buy any of their clothes because my dad is called Grant and that’s just too close: It’d be weird to have your dad’s name on the front of your shirt, unless your dad is Ralph Lauren or something I guess.)
What do you wish more people asked you about your work?
“How can we assure you that we’re actually listening to your suggestions?” I swear to god, the amount of times I’ve worked with a client who has hired me to consult on their strategy and then said “This is great… thanks.” And then I never hear from them again. I’ll see them badly activating on my suggestions in a way that makes it crystal that they weren’t listening when I so thoughtfully laid out the plan. I don’t think this is such a crazy notion but: If you’re paying someone to tell you something you don’t know or don’t understand, listen to them.
What’s a habit, tool, or ritual you swear by?
Writing to-do lists in notebooks. There’s no way I would’ve remembered to write this without it.
You can find Sam on Instagram and LinkedIn.
Working Theories is a spotlight into our favourite people in the industry. Each edition explores how they got here, the industry rules they live by (or break), and the cultural references shaping how they think.