Are You Vulnerable Enough to Experiment?
Take your mind out of the gutter!
Hi Friend,
This issue of the newsletter is coming to you hot from NY where I just had an amazing avocado toast because I’m a millennial cliche. Here’s what you can expect from this one (except maybe some coffee stains from my second Americano I’m sipping while typing):
The tea about the Portal Pages pilot and why holding this experimentation felt like the most vulnerable thing I’ve done in a while
What I’m doing in New York and why it feels like time travel
What bubbled in me when watching Gypsy on Broadway and what it has to do with being an entrepreneur
Work that’s wort it
The rawest, most beautiful text I got in a long time
Ready? Buckle up cause here we go!
The Portal Pages Experiment: Vulnerability in Action
When I invited a small group to join me for a mysterious book club format earlier this week, I wasn't prepared for how vulnerable it would feel. Even inviting people felt deeply personal and vulnerable to me. What if they think the format is weird? What if they expect it to be a normal book club and are disappointed? What if they don’t feel comfortable enough to share and openly participate?
The thing is, Portal Pages isn’t a regular book club (it’s a cool book club! Sorry, had to shove this reference): We don’t necessarily discuss books, but use them as portals for deeper discussions, with the characters as our avatars. I had a whole format outlined and detailed - and I wasn’t sure it would work. I wanted it to be witchy, spiritual, transformative - and I felt like by inviting people into this portal, I’m almost inviting them into my heart, guts on full display. So what did I do? I procrastinated :) I only invited very few people, and then kind of caught myself and invited more at the very last minute.
I believe we don’t speak about this enough:
Experimentation = vulnerability + curiosity in action.
(I’d also say courage, but in my book vulnerabillty IS courage.)
Whether it’s a survey to gauge interest in a new service, a startup’s product pilot, trying to bring together a few different friends into a group, rehearsing a speech you’re giving - it’s the same feeling in the pitt of your stomach, right?
But the thing is, as someone who strives to live life and do business with curiosity and playfulness - that’s actually how it looks like in real life: New idea. Excitement. Playfulness. Anxiety. Vulnerability. Courage. And then sometimes: Elation. A new thing was brought into the world (after tweaking and refining of course, I don’t want to oversimplify it.)
I won’t keep you waiting: the meetup was magical.
I asked participants to introduce thmselves as characters from The Time Traveler’s Wife, to step into different timelines, and to use themes like reparenting ourselves, grief, chosen family and more as reflective pools for introspection. We lit candles, we symbolically set our watches aside (someone even forgot theirs at my place - perfect excuse to meet again!), and we agreed that time is more than our limited perception of it.
Was the meeting a success? Yes, but also: It’s complicated. Yes, because we created magic together - it was an evening of open, thinking hearts and deeply feeling brains. And - it’s complicated because I tested the format and I found out it needed a lot of tweaking before going on with it. So it will be a while before Portal Pages become a recurring event BUT I’m excited and relieved and can’t wait to explore it even more.
A few gifts from me to you:
Subscribe to the new Portal Pages sub-newsletter if you’re interested in getting updates, and I’ll email you:
The playlist I created for the 1st Portal Pages
Printable theme cards
Character guides
New York, Time Travel, and Finding My Audacity Again
So why am I in New York? Officially, I'm participating in AJC’s Global Forum (speaking tomorrow at the Access Unconference so come say hi if you’re there). But there's more to it.
I realized recently that while I've gained so much through my healing journey, I've missed something: My audacity. That bold, unapologetic courage that defined my entrepreneurial self in 2017-2020.
Walking the streets of New York feels like time travel. This city has always represented possibility to me - the place where big ideas are born and bold moves are celebrated. I'm here not just for the conference, but to reconnect with that entrepreneurial audacity as Consider launches.
Going back to the idea of experimentation and playfulness, maybe it’s becuase this is where my best childhood memories happened. Where I allowed myself the most to be a kid.
About a year ago, I was accepted to SheShe, a Meta mentorship initiative for women. When I joined, it was before mediation, before divorce, when I wasn't even sure I could continue bearing life. But it felt like something, a spark of hope. Something to remind me of my professional, creative, curious self who doesn't see limits.
When they paired me with Fiona Darmon as my mentor, I was thrilled. I thought she'd help me "get back on track" and restore my marketing and strategy agency to its former glory, or alternatively, find a job.
How wrong I was. Instead of all my assumptions (like exclamation points, they were incorrect), magic happened. Fiona gave me something much more important than guidance or interviews. She gave me permission.
It started as permission to rest. To recover. To take a moment. (Pause for laughter because if we know each other, it's clear how difficult this is for me. And that's exactly why I needed it.)
It continued as permission to do something strange and write a book. That book became the blueprint for new venture: Consider - a transformative methodolgy of question asking for business and life. And it feels extra symbolic that I’m here in NY as I’m working on launching it next month.
What Gypsy Taught Me About Entrepreneurship
Last night, I walked away from "Gypsy" on Broadway (so good! Audra McDonald is incredible) with many thoughts about entrepreneurship and values, and of course, the sacred idea of resilience and not quitting.
There's something about watching a story of ambition, determination, and the costs of single-minded pursuit that makes you question your own relationship with drive.
As entrepreneurs, we're told that grit and perseverance are everything. Never give up! Push through! But watching Rose's relentless pursuit made me wonder: When is resilience healthy, and when does it become destructive obsession? When should we pivot instead of persist? And what’s the point when resilience makes us blind to the fact that we left the values (that got us here in the first place) behind?
These questions deeply resonate with me looking back at my own journey, and they echo something I’m working on that’s meant to support values-driven and heart-first entrepreneurs across industries.
Work That's Worth It: Questioning Career Priorities
My latest podcast episode with Georgi Enthoven, author of "Work That's Worth It," aligns perfectly with these Broadway reflections.
Georgi challenges the false choice between doing good and earning well - a divide I've experienced and seen with so many people I know. My favorite insight was when Georgi said:
"If you are doing good in the world and you burn out in two years, we lose you."
I'm holding Georgi's question close: "What is worth your 90,000 hours?" It's not just about endurance, but what energizes us enough to sustain the journey. This questioning creates space to examine not just what we're doing, but why - and whether that "why" still resonates with who we've become.
Listen to Work That’s Worth It on Looks Like Work:
A Message That Moved Me to Tears
Recently, I received this message from someone who participated in one of my beta Curiosity Sessions:
"Ok, I don't even know how to describe how deep and critical the insights I got from our session were. I finally understood that I don't believe in myself in this context. I understand it's not about this specific course, but about developing this self-belief. I'm pretty shocked, it caught me by surprise, but of course now I see what's the source of it. Would never have gotten there without your GENIUS questions. I did not expect such profound insights. So I'm sad now but also, I see a clear way from here on out."
Shortly after our session, she organically received demand for a new course - not the one she came to me about, but one better suited for her audience and which she had more confidence in.
This is the power of questions. Not as interrogation, but as illumination. Not to demand answers, but to create space for discovery. This badass business owner took what she got in our session and subsequent process and made magic with it.
Are You Vulnerable Enough to Experiment?
Let’s return to my initial question. Are you vulnerable enough to experiment? To try something that might not work? To show up as your full, complex self?
Consider is my experiment. The Portal Pages was an experiment. This newsletter is an experiment.
After my Curiosity Sessions beta tests this past month, I'm opening the waiting list for Consider's official Curiosity Sessions soon. These aren't typical consulting sessions - they're dedicated spaces for transformation through questioning.
What experiment are you curious about but haven't dared to try? What questions might unlock your next breakthrough?
I'd love to hear from you - hit reply and let me know what you're questioning lately.
Until next time,
Chedva x