So, I moved. I migrated from the "embedded" trenches of product strategy and Chief of Staff (yes, I was wearing two hats, and yes, my neck was tired) directly into the Office of the CIO as an AI Product Strategy Lead. Reporting line? Elevated. Strategic impact? High. Remit? Same-ish.
But the cultural shift is... a lot. Moving from Engineering to being directly under the OCIO is like I’ve moved from the engine room where everyone is covered in oil and arguing about the specific torque of a bolt directly onto the bridge of the ship.
On paper, I should be popping champagne. But in real life I am currently sitting with a very specific, very loud type of stress where I know the mission, but I can’t find the vibe in the dark.
I’ve been mentoring people on navigating change lately, which is kind of ironic because, internally, my brain is currently a series of browser tabs that won’t stop refreshing and one of them is playing music I can't find.
Since I’m going through it, here is the internal philosophical spiel I’m using to keep myself upright.
1. The "Meta-Positive" Lie
Even when a change is objectively career-goals material, the physiological stress is real. We’re losing a version of reality that was predictable.
My brain treats a predictable routine like a perfectly organized Shared Drive, and losing it feels like someone took my favorite, flawlessly nested folder system and replaced it with a single, 5,000-line Google Sheet where all the tabs are renamed "Copy of Copy of Untitled." Sure, the data is all there, and eventually, I’ll build a dashboard that makes me look like a genius but right now I’m just staring at a wall of cells feeling lost.
Let’s just sit with that sense of loss for a second without trying to optimize the discomfort away.
2. No Toxic Positivity (Seriously, Keep It)
I am officially banning the phrase "Everything happens for a reason." Sometimes, the reason is just that tech moves fast and things shift. It is perfectly okay to say: "I’m supposed to be stoked about this, but honestly, it kind of sucks right now and I’m 40% cortisol and 60% coffee." The "shadow" isn’t the enemy. Fear isn't the enemy.
The enemy is pretending you’re fine when you’re actually vibrating at a frequency that could shatter glass.
4. Find Your People (The "Scar Tissue" Strategy)
Connecting with allies is huge, but as an ND person, I have a very specific filter. If I tell you I’m struggling and you give me the "You’re a rockstar, you’ve got this!" vibe, I will physically recoil. I don’t need a cheerleader; I need a co-conspirator.
My specific strategy has always been to recruit mentors who have actually done the thing I’m currently doing and survived. You want the person who can look at your 5,000-line spreadsheet and say, "Yeah, that part sucks, here is how I navigated the stakeholder politics of row 402." You’re looking for tactical empathy, someone who understands the nuance of why this is hard, not someone who tries to "toxic-positivity" you into a better mood. Find the people with the scar tissue; they’re the only ones who can actually help you map the terrain.
5. Seeing vs. Performing
In tech, we are trained to perform competence, especially during a reorg. We want to look durable and ready to go. But there is a massive difference between performing and actually seeing.
The most valuable skill I’m working on right now is active listening, actually understanding the architecture of the new change rather than just nodding along so I look like a leader. True acumen isn’t about how fast you can run; it’s about how clearly you can see the terrain while everyone else is running in circles.
So, if you’re also in the middle of an "amazing" change that feels like a heavy backpack? Same. Let’s stop pretending it’s all excitement and just focus on breathing and noticing. The executive state will follow.
Eventually.
I'd love to hear from you! Please fill out the form below and I'll get back to you as soon as possible.