Side Quests, Homecomings, and New Beginnings
Or: Questions that break invisible walls
Hi there, friend. How has your week been? Mine's been a whirlwind of unexpected adventures and nostalgic homecomings. Let's dive in, shall we?
+keep your eyes open for an offer at the end of this issue.
When Side Quests Get the Main Character Treatment
In gaming, side quests are symbolized by question marks. And as you might guess, this question mark aficionado finds this parallel scratches a brain itch in a very pleasing way.
This week I had a very special side quest arrive with just 18 hours' notice: speaking with the passionate team at Start 800, who promote education around tolerance, coexistence, and values that prepare kids to navigate our volatile world.
We explored how to become comfortable ("make friends") with question-asking in a shaky world that desperately clings to human exclamation points. Through the lens of stereotypes and black-and-white thinking, we discussed how getting closer to what scares us allows both adults and children to tackle challenges and lead with nuance.
As I shared on Instagram (click above to watch the reel): "People assume my favorite topic is strategy or growth or innovation... but it's always this: How can we trade our addiction to exclamation points for the power of a well-crafted question mark?"
Because I've seen firsthand – when brilliant minds pause to question instead of declare – that's when breakthroughs happen. For ourselves, our businesses, and our world.
Homecomings: Design, Beauty, and the Spaces Between
This week I also visited a beautiful showroom/gallery that felt like time-traveling to my former self as a design blogger. The experience was disorienting in the best possible way – reminding me of one of the moments I felt most in my element this year (as I mentioned last week): decorating my apartment.
It raised questions about how I've evolved since my design blogging days. What is the place of beauty, decor, and tangible things in my life now? How do our surroundings transform not just our spaces but our thinking?
I'm reminded of what my podcast guest Olivia once shared: "When you change the stuff around you, the stuff around you changes." There's profound truth in that deceptively simple statement. Our environments shape our questions, and our questions shape our lives.
Have you ever returned to a former version of yourself and been surprised by what you found there? I'd love to hear about it.
Big News: Looks Like Work Season 3 Has Launched!
The first episode of Season 3 is now live! This solo episode introduces the three guiding questions for our new season:
What do you do when your dream no longer feels right?
How do you reclaim a system built to suppress you?
How are you questioning traditional priorities?
I dive into the concept of "gateway questions" – those gentle inquiries that help us approach what we're afraid to confront. As I share in the episode: "When the world feels like it's on fire, there's this powerful urge to flock behind anyone speaking in exclamation points."
But what we really need are gateway questions: indirect inquiries that help us approach what we're truly afraid to face. Sometimes the question isn't "Should I close my company?" but rather "When will I be ready to ask myself that question?"
You can listen to the full episode wherever you get your podcasts (Spotify | Apple | Podbean, for example). I can't wait to hear what you think.
Last Call: Consider Labs Beta Session
For the past two weeks, I've been conducting beta "Curiosity Sessions" through my new venture, Consider Labs. These 90-minute strategic deep dives combine thoughtful inquiry with targeted problem-solving for founders, executives, and creative leaders from all inustries who:
Know there's a bigger vision possible but can't quite see the path
Feel constrained by conventional thinking in their industry
Sense they're operating at a fraction of their potential impact
Are ready for breakthrough rather than incremental improvement
Each session includes a pre-session reflection guide, a 90-minute conversation, recording, follow-up exercise, and an insight-packed document to transform our exploration into tangible momentum.
I'm offering ONE last beta session (including one week of Slack support) before officially launching in May. Interested? Email me right now :)
A Question for Your Week
When was the last time you welcomed a "side quest" that unexpectedly became central to your journey? How did it change your path?
Until next week, Chedva x
P.S. Reply to this email with any questions about the Curiosity Sessions – I'm happy to share more about this new offering and how it might serve you.