Discover more from Wandering the Grey
let's get to know each other 😬
It's embarrassing to admit out loud, but several months ago, I was obsessed with the idea of building a "newsletter empire" here. I checked my subscriber stats way too often. Each time I peeked, my skin itched for the next round number like a comfortable jacket that would keep me warm. When I woke up to unexpected good news—(more subscribers, 😌!), I'd savor that sweet dollop of dopamine. Mmm I’m good at this. But whenever someone unsubscribed, I'd groan from the gut-punch😩. OK maybe not that good, actually.
My logical brain knows that people have to unsubscribe for their sanity. Newsletter overload is a real pain. Sometimes, it's just not the right fit. Nobody wants more bad mail. So you have to prune whatever doesn't bring joy. I know these truths but my lizard, creator brain still felt awful whenever I got those unsubscribe emails.
These days, I rarely check subscriber stats. Because I know they’re a bad proxy for what I really care about. Subscriber numbers are one-dimensional. They can never depict the intangible joys I feel when a reader GETS ME. They can’t capture my smile when someone tells me in real life they read my stuff and loved it.
My favorite part of writing this newsletter has been connecting with YOU. I've made many internet friends—fellow writers, trusty readers, unofficial mentors, people I'm sure I'd have a great beer with. No two readers are the same. We have the silent lurkers who read every word but never comment. Those that reply to every email. The skimmers. The sharers. Those that understandbly read when they have the time. Those that send me encouraging words. I'm grateful for all of you.
But I keep thinking we've only skimmed the surface here in terms of connections. Each of our reader-writer conversations is like a distinct balloon, floating high and beautiful in its own right. But so far, these balloons have floated in isolation—in the comments, I’m talking to one reader one on one—but you don’t know each other. And I don’t know a lot of you yet.
I dream of a buoyant bouquet of balloons where the blues blend with the reds and the threads intermingle with each other. I want this space to accommodate serendipitous connections. Can we get to know each other?
Remember, there are many hundreds of us here. It blows my mind to think about the combined wealth of experience and perspective in this community. Our timezones span the planet. Subscribers from sixty-something countries on every continent.
Twenty Minutes with Tobi update
A few weeks ago, I opened up my calendar for my Twenty Minutes with Tobi series. I thought one or two would book calls but I ended up hosting fifteen calls with people from Melbourne to Mumbai. Someone in Australia woke up at 4am their time to chat with me. (Honestly still baffled and grateful in equal measure). Every single call blew past the allotted time slot.
I talked to people in all seasons—starting afresh, uprooting, planting, doubling down, grieving, reminiscing, exploring. The calls were agenda-less by design and we let curiosity drive our conversations. Since I write about travel and sabbaticals, callers often gravitated towards those topics.
But even as we ventured into familiar territory, I sensed a palpable undercurrent, a longing for something more than casual conversation. Very often, the caller and I broke through the icy chalice of a virtual Zoom rom and shared a vulnerable truth with each other. A dream that isn’t likely to be realized. A shared fear about the future. The feeling of angst while waiting for an uncertain reward.
While we often shared tidbits from the dark corners of our hearts, I was struck by the steely resilience that shone through each dialogue. The sheer courage to dare to push through in spite of fear. The audacity to feel and dream without being drowned out by society’s voices. Visceral hope knocking down the doors and demanding to be listened to.
I…did not expect any of this. I thought people might ask me why I hate on paella so much and we’d have lighthearted conversations about the silly stuff. And we did, but this depth of conversation spoke so loud and clear to me. We talked about divorce, deferred dreams, and the danger of not taking risks. This experiment revealed an obvious, universal truth—people want to connect!
Let’s be friends?
So I want to start a new tradition here. I'll leave this post pinned forever on my newsletter as an "Introductions Wall". My dream is for you to introduce yourself in the comments section and start to meet each other organically.
Little by little, I hope small spontaneous connections start to form like bubbles in a brewing pot. Maybe someone mentions they're in Barcelona and another reader recommends a local favorite cafe to them. Or someone says they're looking for a kind of job and a recruiter responds in the comments. Stranger things have happened…
To get this party started, I'll share a prompt and tag some Substack friends to go first. I know sometimes it’s intimidating to be the first to share in a public space. So maybe my Substack buddies can light up the space first then others can respond as they feel comfortable. I’ll answer in the comments too.
OK here’s the prompt:
Who are you? What season are you in your life? What popular food do you despise? Where is home for you? Is there a place you’ve never been to but feel like you belong? What brought you here? What are you currently procrastinating on?
Substack friends—, ,, , , , , , , , , , , , , , — could you do me in the honours and answer in the comments?
Thank you all so much for your support of this newsletter so far!
In case you missed it:
I'm opening up some time on my calendar for paid calls because a lot of people have reached out to ask about sabbaticals, golden handcuffs, and leaving tech. I've had 30+ of these conversations and would love to support you if you’re curious.