How D&D Made Me a Better Entrepreneur – Character Development

by Amber Krasinski | Business

Welcome to a series I like to call “How D&D Made Me a Better Entrepreneur.” Yes, this is probably one of the nerdiest business-analogy blogs you’ll ever encounter, but hey, you get what you get.

For those that don’t know, D&D or Dungeons and Dragons, is a tabletop roleplaying game where groups of characters roll dice to determine the outcomes of various aspects of an adventure. The adventure is guided by a DM or Dungeon Master who crafts the narrative, creates combat opportunities, and makes sure the rules are being followed. It sounds complicated, but just think about it as a more organized version of playing make-believe. There are several steps to setting up a successful D&D campaign, the first of which being character development. 

To play D&D or any roleplaying game, you need a character. The same can be said about real life.

Who do I want to be? What are my strengths, weaknesses, backstory? How will all of that impact others? What are the items and things I hold dear and have to have? Who are the people in my circle?

These are all common questions we encounter in our daily lives, but for D&D, all of them are carefully considered during Session 0, the planning session prior to an adventure or campaign actually starting off.

You roll the dice or pick and choose stats. Things like athletics, wisdom, dexterity, charisma, intelligence, animal handling…all of it ties into what your character is like and capable of doing. You can bump up certain skill levels, meaning your character is more likely to have a successful outcome since they have higher numbers. However, this may come at a cost, meaning that you’ll need to redistribute those numbers at times and some skills will have a stronger likelihood of rolling at a disadvantage. Your skills are beneficial, but only so long as you’re aware of the other side of the coin, so to speak.

How you build your D&D character determines a lot of the journey you’ll have, just like the whirlwind we all lovingly call entrepreneurship. The proof is in the planning and strategizing. A character’s race can help them gain certain abilities. A character’s class is all about what specific skills they have. Lots of variables, lots of options.

Now let’s put a pause on the nerd-out session. What the hell does this have to do with a business?

It all comes down to these two questions: who are you now and who do you want to be?

To have a successful campaign, you have to know your character inside and out. Are you a druid, communing with nature and trying to improve the environment around you? A barbarian, hacking and slashing your way through the business world at all costs? How does your history and upbringing influence your current thoughts and actions?

After creating dozens of characters, I’ve come to realize that as a business owner, it’s critical to be in tune with yourself and seek answers to these types of questions. Much like a D&D character, you’re on your own journey of self discovery and knowledge seeking, leaning on those around you for guidance and support as needed. Who you are and how you perceive the world can mean the difference between slaying that dragon and landing that deal or losing the battle entirely. Knowing who you are and how that impacts the world around you is a key part of understanding how you can best serve others through what you offer. How can you build your personal and professional identities? How do you align them to your values and goals?

What you do and who you are matters. Stay true to those things and even with the worst roll of the dice, you can make the most out of your life and your business.

Amber Krasinski
Founder & Creative Strategist at IvyHill PR

Amber (she/her) is a proud New Englander with a passion for creativity in all its forms.

With over a decade in video production, marketing, and advocacy, Amber knows what it takes to build audiences and help folks become more confident in expressing themselves. She loves to do research, learn people’s stories, and get results! In her spare time, she can be found helping her partner solve Wordle puzzles, gardening, and adventuring.

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1 Comment

  1. Erick Grau

    Absolutely! Spot on! The correlation is clear and resonant. Both D&D and entrepreneurship require a deep understanding of roles and strategies, as well as the ability to adapt and evolve.

    As a former Dungeon Master, It’s great to see how the creativity and problem-solving skills honed in the realm of role-playing can indeed translate into the business world, enhancing decision-making and leadership abilities.

    Your journey through D&D evidently parallels the dynamic and unpredictable path of entrepreneurship, where every experience can be a step towards growth and achievement.


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