A karaoke-fueled epiphany about the gap between knowing and doing
Helloooooo, from 35k feet.
In Transit is leadership inspo for women going places:
literally, figuratively, and most importantly, actually.
I'm currently 35,000 feet in the air, watching the BTS concert film, and I just realized something about leadership that's been sitting with me since last night in a Tokyo subway station.
If you follow me on IG, you know I've been on the move this past week – Vancouver to Taipei to Shanghai to Tokyo. Now I'm squished in seat 22K on my way to Sapporo for some snowboarding, and I keep coming back to this moment that felt small in the instant but has unpacked into something much bigger.
Let me take you there.
So last night I was stumbling back to the hotel after a 3-hour karaoke session (threeish gin and tonics and a SOLID rendition of Bye Bye Bye to close out the night), and I got to the station and saw what you always see in Japan: the orderly lineup. Two perfectly straight lines on either side of where the train door will be.
Compared to the chaotic blob of people waiting for the subway in New York or the aggressive shove onto the tube in London, it's chef's kiss* organized.
And my immediate rebel instinct?
Stand out of place.
F the system, right?
Go your own way!
But I didn't. I got in line with everyone else waiting for the next Ginza line train.
As I stood there (still buzzing from karaoke) I started thinking about way more than just how different waiting for the train is here. I thought about all the aspects of Japanese culture that are completely different from how I move through my day. And I let myself actually sit with the why behind those differences an be genuinely curious about a different way of doing things.
Which felt cool and evolved and was totally giving "I'm a thoughtful global citizen."
But also? Deeply uncomfortable.
Because being genuinely curious about why I do something the way I do means admitting some truths I don't love. Like that I do it because "I've always done it that way." Or "that's what I was taught." Or the really uncomfortable one: because I've been implicitly told that's what I should do and I never thought to question it.
Here's where this connects to you.
We are smart women. We know that getting to the next level, making the impact we want, and earning the salary we deserve requires growth.
We get it intellectually.
We KNOW that growth means accepting we're not perfect as we are. (I mean, rude, but okay.)
We KNOW it means sitting with the discomfort of challenging our views and our values.
We KNOW it means risking failure and maybe even looking a little foolish.
We totally, completely, 100% understand this.
But here's what we actually feel:
We FEEL like we should be perfect at the new thing on the first try.
We FEEL like we want to stay comfortable, thank you very much.
We FEEL most confident when we're nailing that thing we've done a thousand times already.
And THIS is where we fight ourselves and lead ourselves astray. This is what makes us hunt for quick fixes, "3 easy steps," or those 6-week bootcamps that promise to revolutionize our entire leadership approach.
(And listen, I LOVE a good shortcut. If there was a "Become an Exceptional Business Owner While You Sleep" meditation, I'd have it on repeat. But that's not how this works, and we both know it.)
The leaders who actually make it to the next level? The ones creating real impact? They put in the work. The unglamorous, sometimes boring, often uncomfortable work.
They challenge themselves daily. They reflect on their own preferences, habits, and decision-making styles. They know themselves inside and out including the good, the bad, the "why do I keep doing that?!", so they can leverage their strengths and actually work around their weaknesses instead of pretending they don't exist.
This is why I talk about self-reflection so much in my work and with my clients. Not because it's trendy or sounds good on LinkedIn. Because it's literally the foundation of good leadership.
My clients are blocking time in their calendars right now. Not for another meeting or deliverable, but to simply think. To sit with those uncomfortable questions. To get curious about their own patterns and ask "what might be possible if I questioned just one of these?"
Because here's what I learned standing in that perfectly straight (and silent) line in Tokyo:
the leaders who make the biggest impact aren't the ones who never feel uncertain or uncomfortable.
They're the ones who've built the self-awareness muscle strong enough to navigate that uncertainty with intention instead of just reverting to autopilot.
So here's my challenge to you this week: get uncomfortable on purpose. Pick one thing you've been doing on autopilot and ask yourself why. Actually sit with it. The growth you're looking for is on the other side of that discomfort.
Let's go, girls.
XOXO
Kelsey
This Week's Thing
Okay, so how do we actually put this into practice? Block 15 minutes this week. Just 15. Start small. And ask yourself these 3 questions:
Think about the last difficult conversation you had with your team. Did you handle it the way you always do, or the way that would actually move things forward?
What's one thing you avoid delegating because "it's faster if I just do it myself" – and what's that costing you?
What's a leadership challenge you're facing right now that you keep trying to solve the same way, even though it's not working?