The Adventurer's Digest (July 2026)

Hello Adventures!

This article is going to a mishmash of quest related thoughts and creations. What you will find in this article this week:

• Some thoughts about some of my upcoming quests in August

• A quest suggestion for you based on my TO-DOngeons & Dragons quest

• A couple of polls because I would love your thoughts on some things related to my Substack

• Some thoughts about my new questboard

• A new draft of my professional bio (because why not)

Thanks to an amazing person (thank you, Kirsten!), I have the opportunity and incentive to go to Gen Con for the first time. I am going with an exhibitor pass, and I have it on my quest log to dive much further into preparation this week (I know it’s a bit late for that, but still — I’m balancing a bunch; I’ll get to it when I get to it, and it’s so much information to sift through). Overall though, I am very very excited.

What is Gen Con? I think the website explains it best:

For over 55 years Gen Con has been the largest and longest-running gaming convention in North America. Founded in 1967 by Dungeons and Dragons co-creator Gary Gygax, Gen Con now attracts tens of thousands of attendees from around the world to Indianapolis for The Best Four Days in Gaming™.

So a gathering place of my favorite types of people… people like me — highly ambitious neurodivergent nerds. In many ways, they are my target audience.

I am going to Gen Con with a quest in mind. The quest to answer these three main questions:

1. How the heck does Gen Con actually work, and would I want to do the whole thing next year? If so, at what aspirational level? (Attendee? Exhibitor for Questify Your Life? Performer? Something else entirely?)

2. Can I use this opportunity to discuss some of my more nerdy offerings with my ideal customers — with Adventurers? If so, what information can I get that would be helpful for me to receive so I can better help them?

3. Can I actually remember to take photos and videos of this experience? For social media purposes, yes. But more importantly, to capture at least one memory of something that made me delighted or joyful.

I’ve had so much fun getting to tell people that I am going to Clown Camp. A summer camp from Tuesday to Sunday. I will get to learn all about the business and art of clownery with 99 other clown campers and all of the amazing instructors. All in the a summer camp atmosphere that including a fire pit, crafts, a good friend, and a lake.

You may be wondering, “Why? Do you want to be a clown?”

Yes and no. I love what I do and what I am building. Yet, the skills related to clownery are incredible beneficial for every part of my business, from the nerdy quest side of my business, to my public speaking, and even my advocacy work. My hope is that by spending more time and learning from people who are having a fun and joyful time within themselves, that I can remind myself that:

Yes, things are serious and exhausting, but I don’t always have to be.

Want to know what’s as fun or more fun than saying “I’m going to Clown Camp next month!”? Getting to say, “The week after Clown Camp I am flying to New York to Watkins Glen to give my first TEDx talk!”

I’ll be speaking about how disability and neurodiversity discussions need to be included in DEI conversations, especially now that DEI is under attack (the title is still a work in progress)

I am, however, worried about what to wear. And I will worry about that for the next several weeks, and then I’ll likely just dress up my character the same way as I almost always do when I am presenting or teaching. Thin black turtleneck, velvet teal blazer, black pants, belt with gold belt buckle, teal flats, hair down and curled, black winged eyeliner, and a dark lip. But who knows, maybe I’ll find something when shopping over the next few weeks and I decide to go a different route.

Either way, I hope that room has good AC.

I’ve recently started a new side quest. I created this because I want to make progress on some of the miscellaneous quests that are just sitting in my quest log. But to make it more fun, I’ve created a list of DnD races, classes, and backgrounds, and I’ve written those out on small pieces of paper that I pull out of a jar at the beginning of the week. (Or whenever I remember).

Themes list in case you are interested: Human; High Elf; Wood Elf; Dark Elf; Dwarf; Halfling; Dragonborn; Gnome; Half-Elf; Half-Orc; Tiefling; Aasimar; Air Genasi; Earth Genasi; Fire Genasi; Water Genasi; Tabaxi; Goblin; Fairy; Artificer; Barbarian; Bard; Cleric; Druid; Fighter; Monk; Paladin; Ranger; Rogue; Sorcerer; Warlock; Wizard; Artisan; Charlatan; Entertainer; Farmer; Guard; Guide; Hermit; Laborer; Noble; Pilgrim; Sage; Sailor; Soldier; Wayfarer

Last week I pulled out two themes with the intention of choosing between them, following the one that I felt more inspired by, and putting the other one back in the jar.

I pulled out “Wood Elf” and “Rogue.” Wood Elf felt right for me. I have some yard work I’ve been putting off, a hike with a friend that I wanted to finish planning, and I could make a phone call or two while taking a long walk.

But… last week was so hot, and the smoke from the northern fires was too much to go outside.

So, I pivoted to Rogue. According to DnD Beyond’s Wiki on Rogues: “Rogues rely on skill, stealth, and their foes’ vulnerabilities to get the upper hand in any situation.”

So, inspired by the concept of a rogue, I decided that I would spend several hours pretending that I was sneakily helping a future version of me as I dealt with small tasks that hadn’t yet been under prioritizing. What could I do that would make tomorrow’s version of me feel a little bit better?

So, here’s a list of many of the things I did, in case it inspires you to do something similar:

• Cleaned out some of my draft emails

• Filled my printer with more printer paper

• Requested a quote for radon mitigation

• Made a (admittedly too ambitious) social media plan for the following week

• Made a handy list of phone numbers and scripts that I needed for the following day

• Updated my business phone number

• Cleaned the inside and the filter of my dishwasher

• Cleaned my microwave

• Make a seasoning blend for easy roasted vegetables

• Update some documentation for a grant I applied for

• Took out most of the craft supplies I would need for the upcoming terrain build for my Dungeons & Dragons campaign

Sometimes I have to get creative with the way I get things done. But it was successful since I was productive and had a good time. Besides, the tactic just needed to be useful, not perfect.

This final poll is for paid subscribers only. Thank you for supporting me and my work. I appreciate you beyond what words can communicate. I am working on figuring out a way to show my appreciation to my paid subscribers and would love your input on it.

In this Instagram Reel, I share a bit about my questboard. For those who don’t watch it, though, the goal is to have a tangible place to document progress, while also being able to shut it and put it aside as I work on going on my quests and enjoying this adventure. I’ve found that a tri-fold board and collage materials work really well for that. Kind of like a video game quest menu — open it up to see what I am working towards, shut it as I adventure, and open it up again to see how much progress I’ve made. The collaging also helps me slow down and appreciate the accomplishments I’ve attained as I quest.

I’ve been overthinking my professional bio. Over the past year or so, I’ve continued to tweak it, yet for a while it felt very backwards-focused, rather than looking ahead. Like more of the focus was on what I have done as a way to show status, rather than on what I am doing and building. So, here is my current draft.

Sierra Grandy identifies most as an adventurer. Her main quest is as a professional speaker on neurodiversity, disability, and mental health recovery, helping workplaces and communities build more inclusive, effective, and accessible teams. Sierra is also the founder of Questify Your Life, a storytelling studio and creative guild,w here she helps other adventurers, through her various offers. Including the Adventure Party (her gamified coaching program), executive coaching built for neurodivergent professionals, and her work as a professional Game Master for corporate team-building RPGs (similar to Dungeons & Dragons, but highlighting skills related to psychological safety in the workplace).

Additionally, Sierra is an avid volunteer, advocate, and advisor in her community. She is a licensed attorney in the state of Minnesota, and occasionally practices pro bono through some of her favorite organizations. She serves with leadership roles within the National Alliance on Mental Illness (NAMI), the Minnesota State Advisory Council on Mental Health, and the Minnesota Disability Bar Association. Additionally, Sierra is an active member of the Neurodiversity Coalition of America.

I am open to your thoughts, but overall, I am just glad I pulled some words together that make me feel like I am making progress with the vision of what I am creating with my speaking business and with Questify Your Life.

Thanks for reading! I appreciate you!

Whatever quest you are on, I am proud of you for going on it.

With pizzazz,

Sierra