The Questions We Don’t Dare to Ask- Looks Like Work, Season 3, Ep 1
Let’s be honest: “What do you do?” has never really cut it.
Not when your dream job starts to feel like a straitjacket.
Not when the world is on fire and you’re trying to scale a mountain and get your kid to therapy and make a salad that doesn’t taste like resignation.
In this solo season opener, I (hi, it’s me, Chedva) ask three questions that don’t always get polite dinner party airtime:
What do you do when your dream no longer fits?
How do you reclaim a system built to suppress you?
What happens when you stop optimizing and start asking?
Not in a doom-scrolly, AI-overlord, existential-crisis way (although, let’s be real, those vibes are there too). But in a slow, breath-between-the-lines kind of way. With what I call gateway questions. The gentle kind. The kind that sidle up to your fear, rather than kicking it in the teeth.
Because sometimes we don’t need bigger answers—we need better questions.
This episode is an invitation. Not to fix everything. But to sit with the friction.
To ask what you’re not asking.
To notice what’s shifting.
To consider:
When did you last allow yourself to not know?
Where are you defaulting to answers instead of curiosity?
What might you find if you cracked open a question you’ve been avoiding?
Season 3 is for the ambitious and the questioning. The ones who’ve achieved a lot but still feel the itch. The ones who want more—not just in volume, but in alignment, intention, and realness.
So if you’ve been craving space to not have it all figured out? You’re in the right place.
New episodes drop weekly. Bring your mess. I’ll bring mine.
This episode is an invitation. Not to fix everything. But to sit with the friction.
To ask what you’re not asking.
Resources & Mentions:
Subscribe to the newsletter: chedva.substack.com
Check out The Curiosity Lab and CuriosityGPT
Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean
