🤝 Hello! It’s nice to meet you
My name is Cortney Jacobsen, aka “Contrary Cortney,” as you will learn in this publication.
I left a 25-year career leading product for tech companies to build something of my own, travel the world, and write about all of it honestly. No fairy tales.
If you are someone who believes that that best things - in life and in business - are built by pushing against the norm, stepping outside your comfort zone, and asking interesting questions, Contrary Cortney is for you. Welcome 💚
Above all else, when you subscribe, you will get brutal honesty. If you think about these things, like I do, then you are in the right place:
What would I create if I stopped trying to fit someone else’s rubric for success?
How can I listen to my intuition, my heart, and my gut? And come up with a pragmatic plan to comply with all three?
What are the lessons to be learned from products/founders all over the globe who are able to maintain integrity, authenticity, and humility while also growing?
How can all women seize their full power? How can we inspire each other? And especially, how can I do this in a moment of life/brain/body changes that come with middle age and perimenopause?
What could I learn from new people, cultures, and places?
Contrary Cortney is a FREE Subscription. Stay tuned for future subscription tiers.
About Me - A layer or two deeper
From the time I was small, my mother called me Contrary Cortney for my relentless curiosity. I asked ‘Why’ when everyone else asked ‘How.’ I pushed back when no one else was pushing back.
That instinct built a 25-year career in product management. I’ve worked in the trenches of 6 start-ups, 2 tech giants, and 1 company that I co-founded. I’ve launched 5 zero-to-one products that captured 50% of new company bookings in the first year, doubled subscribership, increased market share >10%, and consistently delivered >85% customer satisfaction. I’ve led 3 digital transformations that drove 3% savings in operations through AI optimizations. I’ve built and architected product organizations of 60+, led global expansions, and received two Amazon Inventor Awards.
Product found me at the intersection of creative thinking, engineering, business strategy, and human connection. It’s where I’ve always belonged.
In 2026, I made another contrary move and decisively stepped away from the ceaseless ladder-climbing to answer a question I’d been avoiding:
What would I create if I stopped trying to fit someone else’s rubric for success?
This Substack is the journey to answer that question, in real time. I write about the transition from corporate to independent consultant, and share personal and professional musings from travel. The curiosity that made me contrary as a kid is still the thing I trust most.
These days I work as a product consultant and writer, giving myself time and space to explore all of the creative ideas that have been boiling up inside of me over the years.
Let’s connect.
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