How 2M+ Professionals Stay Ahead on AI
AI is moving fast and most people are falling behind.
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Allow me to reintroduce myself.

I mean, we’re both from Brooklyn.
When I launched this newsletter two-ish years ago, I was speaking broadly — to anyone trying to figure out talent. But as I consulted, coached, and wrote, the person I kept finding on the other side of the table was basically the same person every time. Very smart, had a high bar for excellence. Cared deeply about outcomes and about the people delivering them- but didn't have a space to figure out how to integrate all of that in a way that was actually authentic to who they were.
Leadership content talks about the ideal. It tells you what to do. What it rarely does is create space for the mess- and the mess is where we actually learn and integrate. Most of us figure it out by trial and fire. But why is that still the default?
I'm not asking that abstractly. It's personal.
My first year as a principal, I was convinced the problem was systems. And truth be told, I wasn't wrong — the place was held together with vibes and goodwill, and neither of those scale. So I built systems. Some of them were too tight, but the bigger issue was that I didn't build the story around them. No shared understanding, no room for people to make sense of what we were doing or actually buy in. Without that, structure doesn't feel like support. It feels like handcuffs. Which, as you can imagine, went super great.
Year two I overcorrected hard in the other direction. Heavier on teh inspiration and trust— but so vague, so hands-off, that people didn't have enough to work with. I thought I was giving people autonomy. I was mostly just giving people confusion. Year three I finally found the balance — or something close enough to it that I stopped second-guessing every decision I made.
Year four broke me. And if I'm being honest, I think there's a part of it that never fully healed the way it should have. That's not something I say for sympathy — it's just true, and I think a lot of people in leadership have a version of that year and never say it out loud.
What got me through wasn't some great support system or a mentor who showed up at the right moment. I white-knuckled it. I didn't always know who I could lean on or who I could trust, and so mostly I just kept moving. What has helped — over time, in retrospect — is becoming the person I wish I'd had. And building the systems I wish I'd operated in.
That's not a tagline. That's just what happened.
That's what I kept seeing when I moved into the CPO seat, and then into consulting. Smart people. Capable people. People who wanted to lead well and genuinely cared about getting it right. But nobody had told them what the job actually required — not until they were already in it. And when things got hard, they were doing it alone too.
This newsletter is for them. For you, if any of this sounds familiar.
As for what's actually changing here— honestly, not that much. You'll still get the same resources, tools, and practical frameworks. Workshop announcements and subscriber discounts. Recommendations worth your time. Possibly more gifs. What's shifting is just the honesty about who this is really for and what we're actually doing here.
Oh, and there's a paid tier coming. Stay tuned for more.
P.S. In astrology, Chiron is called the wounded healer — the part of your chart that shows where you've been hurt and what you're here to transmute. Mine is in the house of career and public authority. I didn't need a birth chart to tell me that, but it's nice to have receipts.
P.P.S If you are also an astro-nerd, let me know. I’m taking an astrology course now and am fascinated by it (and happy to tell you where your Chiron is).
What’s Coming Up
I have two free webinars coming up, and I’d love to see you there:
You’re Not Managing People Anymore, You’re Managing Managers (April 7)- Managing Managers isn’t the same job as managing people- an most senior leaders were never taught that. If your managers re still bringing you every problem, the bottleneck isn’t the, It’s the conditions they’re operating inside. This lesson gives you the framework to fix that.
So They Made You A Manager- Here’s What Nobody Told You (April 16)- You were put in charge. Nobody handed you a playbook. So you figure it out alone, in real time, while everyone expects you to already know. That gap between being promoted and feeling like a leader is exactly what we’ll talk about.
And kicking off on May 13th, I’m kicking off the next Leading With Clarity cohort. This is for folks leading people, teams and projects who want the tools and the space to make them their own. And for folks on this newsletter, you can use this special link to get $100 off, from now until April 15th.
1% Solutions
Ratings tell you what. These questions tell you why- Ratings on feedback forms are good. They're just incomplete. If your pulse surveys or feedback forms are getting flat, vague responses, the questions are probably too safe. "Did you find this helpful?" will get you a number. "What would have made this more useful?" will get you information. Try adding prompts that actually require people to think: What have you actually done with this information? What are you still unsure about? People will tell you the truth when the question makes room for it.
Your best individual contributor just got promoted. Now help them stop acting like one- Moving from individual contributor to leader is less about learning new skills and more about unlearning old ones. The hardest habit to break is solving things yourself — because that's exactly what got them promoted in the first place. As their manager, your job is to name that directly and early. When they come to you with a problem, resist the urge to help them solve it. Instead ask: what do you think your team needs from you right now? Who on your team could own this? What would it look like to coach someone through this instead of handling it yourself? You're not withholding help — you're modeling the move you need them to make. Do it enough times and they'll start doing it with their own team.
What I’m Reading
How Leaders Can Build a High Agency Culture- Motivation and agency come from seeing the results of one’s work. But what happens when so much is out of our control? How do we create a high agency culture when we feel like have so little? This article shared some brilliant tips on what leaders can do to in real time to build that agency and motivation in tehir teams- especially in industries where there is such volatility (which is all of us?)
Is There Anyone That Middle Managers Can Trust- I wanted to stand up and cheer for this article. It highlights why middle managers don’t have safe spaces, why that matters and how to fix it. This is not touchy feely- this is about designing systems that support them so they can support the business.


