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Career Highlights:

Aaron Cullers
Aug 4, 2025
Rebooting in Real Time
Thirty days ago, my calendar cleared itself.
Not for a vacation, though there was one scheduled for two days later that was subsequently canceled. Not for a bereavement leave, despite a local tragedy hitting awfully close to home. Not even because Microsoft glitched out, though the equipment hated Chrome tabs with the burning passion of 1,000 fiery suns.
It cleared itself because I’d reached the end of a chapter I didn’t see wrapping. The meetings I’d had and the stack of To Dos I’d continually curated and evolved, went blank. (Literally… logged out blank.)
So… in those 30 days, a lot of things about being a “VP of Marketing” became crystal clear. Like how when the job vanishes, your instincts get really LOUD really QUICKLY. I couldn’t hide behind the “too many meetings” or “what’s the priority this next hour?” anymore, even if that had become comfortable while rebooting the rest of life around that safe haven.
Suddenly it was time to look at the actual work I wanted to do, not the performance of leadership. The difference between those two? Terrifying. Clarifying. And exactly the thing I’d been avoiding.
Leadership isn’t about driving results. It’s about having a compass when the map burns. No team to manage? No Teams calls to answer? Now it became time to remind myself that I actually have a philosophy about marketing, and not just a KPI fetish.
Here’s the biggest gift of this transition into the next role where marketing leadership rules the day: You only know your value when you're forced to sell it without a logo behind you.
I have no fancy brand (self-effacing Tomorrow CMO fire notwithstanding.) No budget. Just me, a tiny keyboard, and a damn good story about what I’ve built, and what I’m building next.
So what does this mean for the next chapter? For me? For you? For anyone who’s worn the title and wondered what was left underneath it? It means we lead differently. With urgency and curiosity – not panic or defensiveness. With humility, because no one is immune in an economy and a sea change like this one, and that’s the gift. That’s the new ground to stand on. The blank calendar to build upon.
If you’ve ever been laid off, left behind, or leveled by your own ambition, I see you. If you haven’t? Look around… marketing as an industry is rewriting rules in real time. Was always going to be better to prepare, rather than pretend.
Tomorrow CMO is a new leadership playbook, and I block time on my own calendar to write it, too.