climbing cringe mountain (don't miss this)

Hi Playmakers!

I have a confession to make.

In 2025, I was pregnant, managing my VC fund, and preparing my world for Roman’s arrival. When he was born, he (rightfully so) became my primary focus. Now that our family has settled into a routine, it’s time for me to take inventory of the life I’ve built.

After thinking long and hard, I realized one major thing… I’ve been playing it safe.

When I launched this newsletter, I wanted a space where I can channel my purest work, away from the noise of algorithms and feeds. My goal was to take my “Why Not Me?” mindset and give you immense amounts of value every single week. I wanted to take the lessons I’ve learned from working with billionaires, being in the rooms behind closed doors as a venture capitalist, and building my own life from a small town to Silicon Valley, and share them in a way that inspired and unlocked potential in everyone that reads my work every single week.

And 2025 was a great year! This newsletter alone reaches over 45,000 people every week.

… but I’ve been playing it safe.

I’ve mostly been operating within familiar territory. I don’t stray too far from the type of content I’ve been writing for years. I’ve been sticking to formats and styles I know well. Basically, I’m comfortable.

And if I’ve learned anything at all over the course of my career, comfort is where you stagnate. I’m not interested in simply going through the motions. I’m here to make a difference, and in order to do that, I have a specific journey I need to endure.

… I have to climb Cringe Mountain.

The Wednesday Play is going to evolve in a big way, and along with it, I’ll be expanding into new formats, new platforms, and new ways of championing the “Why Not Me?” mindset.

Leaving my comfort zone means trying new things. It means failing. It means putting myself out there in ways that are unfamiliar.

It means embracing the cringe.

I’m not here to talk about a mindset. I’m here to live it. Growth and change require a period of discomfort. Starting next week, The Wednesday Play is going to become something new, something unapologetically authentic, something that fully and completely embraces my message around growth, empowerment, and taking big swings in life.

Starting next week, this space is going to transform. I’ve listened closely to my readers and followers, and I’ll be providing more of the insightful content you love.

I’ll be sharing a full rundown of what to expect moving forward on my LinkedIn on Tuesday. (Follow me if you don’t already.)

The updated newsletter will continue to drop on Wednesday with more formats coming soon.

TBH, I’m pretty nervous to begin my climb up cringe mountain. But I figure if I can keep an 18 lb(!) three-month-old alive, how hard could this be?

Drop me a reply and tell me what you want to hear more about. See you next week.

Jenny