Life coaching… but with more whimsy, more structure, and an adventuring party.
Instead of playing a character in a fantasy world — you become the adventurer and real-life goals become the quest.
The Adventure Party is a 10-week, gamified group coaching experience inspired by Dungeons & Dragons — no prior knowledge of the game required.
You’ll join a small Adventure Party (up to 6 adventurers) pursuing similar goals. Together, you’ll move through five story-driven levels, complete structured quests, and build real momentum through:
Accountability
Skill-building
Reflection
Play
Community support
The Structure:
10 weeks total
5 Levels (each spanning two weeks)
Party meets every other week for 2.5 hours
Customized Quest Documents for each level
One individual Adventure Strategist session with Sierra
Optional access to joining the Questify Your Life Guild
Each level builds on the last.
Each quest is intentional.
Each adventurer moves at their own pace — but never alone.
Level 1: Character Creation – Clarify your values, complete a simple well-being audit, explore your aesthetic and identity, and design a character that reflects who you are and who you’re becoming. Begin with small, individualized quests to build trust and momentum.
Level 2: Quests & Call to Action – Design your individual and group quests. Identify obstacles and “dragons.” We may even use light role-play to creatively problem-solve challenges.
Levels 3 & 4: The Adventure – Take action. Adjust. Experiment. Learn. Build sustainable momentum with structure and flexibility. Every campaign unfolds differently based on the adventurers within it.
Level 5: The Final Boss & Celebration – Reflect, integrate your growth, celebrate wins, and close the story intentionally with rewards.
(Maximum 6 Adventurers)
This is the first-ever Adventure Party! And I’m looking for 6 founding adventurers to help shape it.
As a founding participant, you’ll get the full 10-week experience at a discounted investment, plus a direct line to me as we build this together. Your feedback helps shape every future cohort.
Scheduling: Rather than locking in fixed dates before the party is assembled, I’ll work directly with accepted adventurers to find a meeting cadence that actually works for everyone. Once the party is formed, we’ll confirm our schedule together before we begin.
Ideally starting the first week of September 2026.
If you’re ready to commit to a 10-week adventure and show up for your party, the exact timing is something we’ll figure out as a group.
$550 for the full 10-week experience.
(The Adventure Party is evolving towards the end price of $1,300. This is your lowest-ever entry point; and your chance to help build something from the ground up.)
Because parties are intentionally small, placement is thoughtful.
Complete the interest form to help determine:
I personally review every response and follow up with next steps. If you’d prefer to discuss whether you’d be a good fit, feel free to add yourself to my calendar on my contact page.