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“How Dungeons & Dragons made me a better critical thinker, problem solver and leader”

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Kayleigh Dray
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Could joining a D&D group be the secret to bossing your career? Stylist’s digital editor Kayleigh Dray certainly thinks so…

I’ve always been a People Person. By that, I don’t mean that I’m overly charismatic, or gregarious, or great with the chit-chat. You won’t find me in the middle of the party, twirling a glass of champagne in my fingers as I regale the room with my delightfully funny anecdotes. And I’m definitely not the sort of person who relishes giving presentations or speaking up during meetings. Far from it, in fact.

Maybe I’ve got this wrong, actually. Strike the above: I’m not a People Person – I’m a Please The People Person.

Now, you don’t need me to tell you that people-pleasing isn’t inherently a bad thing. In fact, it’s healthy to want to please your family or your supervisors. But there are times when your desire to please others can become problematic: you start taking on too much work, you find it increasingly impossible to say no, and it becomes more difficult than ever to make a decision. To quote Tehyi Hsieh:, when we “lean too much on other people’s approval, life becomes a bed of thorns.”

But it doesn’t have to be this way. All it takes is a dash of self-awareness, a healthy dollop of newfound confidence and a lot of Dungeons & Dragons (D&D) sessions.

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Let me guess… you have no idea what I’m talking about, do you? You either heard the word ‘dungeons’ and assumed I was talking about Satanism or some kinky BDSM-esque stuff, or you heard the word ‘dragons’ and balked at the unashamed geekiness of it all.

First things first, I’d like to clear something up: there is nothing wrong with bondage and foreplay, so long as everyone involved has given their full and enthusiastic consent. There’s probably nothing that wrong with Satanism, either, if you make a conscious effort to avoid the blood sacrifice stuff.

Secondly, being an out-and-proud geek is awesome. As Simon Pegg (of Shaun of the Dead and Star Trek fame) tells us: “Being a geek is all about being honest about what you enjoy and not being afraid to demonstrate that affection. It means never having to play it cool about how much you like something.

“It’s basically a license to proudly emote on a somewhat childish level rather than behave like a supposed adult. Being a geek is extremely liberating.”

Perhaps unsurprisingly, Pegg and I aren’t the only ones who have embraced our inner geeks: in fact, a whopping 20 million people worldwide have played D&D since it was created in 1974, with more than £705,330,000 spent on gaming equipment and books. There’s a brilliant web series called Critical Role – produced by Geek & Sundry – in which a group of professional voice actors play D&D and bring their audience along with them on their epic campaigns. (Each episode is streamed exclusively on Twitch and then archived on Geek and Sundry’s YouTube channel.)

And, thanks to enthusiastic endorsements from the likes of Judi Dench (rumour has it she acts as Dungeon Master for her grandkids), Dwayne Johnson, Felicia Day, Ashley Johnson, Vin Diesel, Matthew Mercer, Laura Bailey, Wil Wheaton, Marisha Ray, Netflix’s Stranger Things and more, D&D is no longer a game for social misfits in shadowy basements. It’s exciting, intelligent, different and downright cool.

So what is it?

Well, the concept is simple: a group of people create and develop characters by rolling dice which determine skills and abilities. These characters are taken on adventures which are plotted by a separate player – the Dungeon Master.

You can be a fighter, a thief, a wizard. Or perhaps you might prefer to be a bard, a druid, a barbarian, a sorceress or a cleric. You might wield an axe, a sword, or a bow and arrow. You might prefer to stick to, y’know, a magical staff. You might want to write yourself an epic backstory (mine often feel more detailed than my dissertation did), or keep it to a few short lines outlining the basics (“I’m a ranger, I don’t talk much, and I’m only coming on this expedition for the gold”).

The possibilities are endless. Not only does D&D allow you the chance to be the sword-wielding hero (or villain) of your dreams, but it also gives you the chance to play in independently-created universes, exercise your imagination, reignite your childhood interest in storytelling and make friends with the sort of people you’d never usually meet.

It also teaches you a series of incredibly important new skills – all of which will prove vital in the real world, particularly in terms of your career.

These skills include, but are not limited to…

Teamwork and cooperation

Every single outcome in D&D is determined by your choices as a whole – which means you all need to work together to ensure you get the story you want. When an enemy is advancing, it’s no good shouting over each other. And, when there’s a big battle to be won, no one person can save the day: each character will have a particular skillset, which fills a role on a diverse team. If they do their job well, the team will succeed. 

And if they don’t? 

Well, everyone will suffer the consequences…

Negotiation tactics

From secretive innkeepers to captive spies, you will come across a lot of tricky characters in D&D – and it’s your job to work out how best to convince them to share that important information they’re withholding. 

Critical thinking

In D&D, you become both the chess player and the chess piece as you’re faced with problem after problem, all just barely solvable. Which means that, as each event of your game unfolds, you will be forced to think on your feet and come up with the answers you need… fast. 

I bet that some of your most memorable moments will likely end up being times that you felt like your back was against the wall, but you managed to pull through using nothing but your wits and a well-timed cantrip (“I thought we were well and truly done for – thank the Maker for the Entangle spell, eh?”). And, trust me, this game really rewards those players who find clever solutions to tricky problems


D&D doesn’t just teach you the basics of working with others: it also gives you the chance to examine the way you interact with your peers, and the role you naturally lean towards in a team. Maybe you’ll find that you prefer to take charge of the situation, leading conversations and choreographing battles whenever you can. Maybe you prefer to delegate tasks to others, so that everyone knows exactly what to do. Maybe you’re more of a supportive leader, giving everyone the chance to shine and only stepping in to help when truly necessary. Or maybe you have a different leadership style entirely – now is the time to explore all the possibilities and find out, once and for all.


There is no real ‘win’ or ‘lose’ in D&D – but some outcomes are definitely more disheartening than others. One of your companions could be killed off in a grim battle sequence, or that expensive Potion of Health could turn out to be fake, or you may try out a new fire spell… and wind up burning down an entire village. 

Thankfully, though, this game really does teach you to roll with the punches, almost literally: new characters can be brought in all the time, you gain points for all experiences (including negative ones) and there’s always a light at the end of the dark, goblin-filled tunnel. Which is, in fact, the ultimate win.


D&D offers you a safe space in which to examine the way you respond to stressful situations – and that’s putting it lightly. Each roll of the dice can take the story in a completely different direction, bringing you face-to-face with an unexpected foe – or forcing you to navigate a tricky terrain or landscape


On a personal note, I’ve found my D&D sessions have helped me to shake some of my crippling people-pleasing tendencies.

Interaction and decision making is integral to the D&D experience: you have to put yourself into the situation and act “in character” – which really can help overcome social issues. Someone who is nervous around people could easily play a charismatic rogue, for example. Someone who spends their life adhering to the rules can adopt a more “chaotic” attitude to life. And someone who is so anxious to please everyone that they can’t commit to any decision, like myself, can step into the shoes of a confident, axe-wielding barbarian – and discover what it really feels like to act based on their purest impulses.

Her giantess genealogy aside, my first ever character, Iona ‘Dawntreader’ Elanavi, was as unlike me as you can possibly be. She’s fiercely independent, for one, and thinks nothing of charging into battle alone. She lives life according to her own code (loosely based on the nine noble virtues of the Vikings). She isn’t bothered about making friends, or having people like her, which means she can be as rude and as blunt as she wants (“you want to know what my axe is called, do you? Say hello to Sudden F**king Death!”).

Meet Iona (and excuse her appearance, please)

Perhaps most importantly for me, though, is the fact that she rarely overthinks things: Iona isn’t fond of detailed planning and discussion. Instead, she does pretty much whatever her gut tells her – which has led to some seriously sticky situations (why sneak past a hoard of Orcs when you can carve your way through them with an axe, eh?).

Despite her obvious conversational shortcomings, playing as Iona has really helped me level up my social skills, too: forcing myself to act out her hot-headed confidence is essentially the same as slipping on a mask, helping me to feel less vulnerable and ultimately more comfortable when talking to others. Over time, she’s helped me get over my shyness and feel more confident cracking jokes and starting conversations on my own. Her calm, level-headed approach to stressful situations has proven useful, too. During one intense battle, she held her ground despite heavy enemy fire – and her composure inspired countless numbers of the game’s farmworkers, many of whom had never picked up a weapon before, to do the same.

No wonder, then, that she’s convinced me it’s time to stop playing and start leading. For my next campaign, I’m due to take on the role of ‘Dungeon Master’, which means that I will be fulfilling the two important functions during a roleplaying game: referee and storyteller.

As the rules for Dungeons & Dragons are vast and complex, it’s the job of the Dungeon Master to facilitate gameplay and to determine the outcome of contested events by deciding how to interpret a given rule or dice roll.

It’s also the job of a Dungeon Master to provide the setting for the players’ fictional characters, create goals for them to accomplish, and to fill any supporting roles needed for the adventure (kings, princes, dragons, innkeepers, barmaids, villains, etc.).

Essentially, the ultimate goal of a Dungeon Master is provide a fun and satisfying challenge for the players to overcome, through acting, exploration, puzzle-solving, and scenario-based decision-making… and, while I never would have felt able to do so before, my time as Iona (and playing with different DnD groups) has convinced me that I’m more than capable of not just running my own campaign, but excelling at it, too.

MookyChick founder Magda Knight – who hosts fun, boozy D&D sessions on a weekly basis – wholeheartedly agrees with me.

“There’s something about D&D that makes everyone shine,” she says, when I ask for her thoughts on D&D’s confidence-boosting abilities.

“RuPaul (of RuPaul’s Drag Race) points out that ‘when you become the image of your own imagination, it’s the most powerful thing you’ll ever do’. And, OK, he wasn’t talking about D&D, but the wisdom of his words still stands: literally EVERYONE becomes wittier, braver, more cunning and ridiculous over the course of a night with the dice. It unleashes the Mother of Dragons and the Peaky Blinder in you.”

She adds: “We all have personal qualities that, despite being very much a part of us, so rarely come to light in everyday situations. Qualities like deadly wit or risk-taking courage aren’t encouraged in urban work culture where everyone is expected to grease the industry wheels and bekind of OK to hang with, but not too wild.

“All your gorgeously extreme qualities are far more likely to blossom when you’re thrown into impossible situations.”

Fancy getting stuck into D&D yourself?

First things first, you need to work out which D&D world you want to play in (because, naturally, there are a lot of them). As a rule, I’d check out the likes of Fate, Pathfinder, Star Wars: Edge of the Empire, of course, and the Dungeons & Dragons fifth edition

Most sets come with their own player’s manual – and, while some may require extra books, the majority of D&D games demand very little in terms of materials. 

As a rule, though, you will generally require…

  • A Dungeon Master
    This person needs to lead the story and make it as exciting as possible – and will need to be happy to read a lot about rules, other worlds and the like. Choose wisely.
  •  Dice (lots of them)
    No, I don’t mean the usual six-sided dice: most games will require a number of different dice (for example, classic D&D demands a 20-sided dice for most initiative rolls).
  • Character sheets
    You can usually get these online – or, if you’re buying a set, they’ll be in the back of your player’s manual.
  • Pencils
    Never use a pen on your character sheet: as you play, your character’s abilities, armour class and constitution will constantly be in a state of flux, so you will need to do a lot of erasing and rewriting. Therefore, you need to make a return to the classic schoolroom staple of the pencil (and a rubber).
  • A large flat surface area
    You need room for all those character sheets and manuals – and, of course, some people like to play with maps and figurines, too (although these are optional). I recommend sitting up at the table or creating a nice cosy den of pillows on the floor.
  • An active imagination
  • People
    These are not solo games – and it really is a case of the more people you have involved, the more fun you’ll have. As a minimum, I’d suggest getting together a group of four to five players – and, if your friends are refusing to jump aboard the D&D wagon, worry not: there are plenty of meetup groups around the country you can join, too.

Still not sure you’re ready for D&D? There are also plenty of YouTube channels dedicated to helping people navigate the D&D world: some help you create a combat encounter, others break down the basics and some go into the real nitty-gritty details of RPG.

In short, you have no excuses – so get out there and try something new, if only for the sake of your career… 

This article was originally published in 2018.

Images: iStock


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Kayleigh Dray

Kayleigh Dray is Stylist’s digital editor-at-large. Her specialist topics include comic books, films, TV and feminism. On a weekend, you can usually find her drinking copious amounts of tea and playing boardgames with her friends.

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