I always planned for this podcast to cover a range of conversations.
And The Venture Variety Show was never meant to be a lineup of the same format week after week. Some episodes go deep on sectors or founder tactics. Others look at how the platform role is changing in venture.
Today’s episode moves in another direction. It focuses on reinvention and leadership, and it lands in a real way right now as so many people young and old here in Silicon Valley and elsewhere are navigating change.
Today’s guest is Cathy Brooks. Cathy is an executive leadership and communication strategist, a longtime storyteller and she’s someone who has lived through several professional arcs. Journalism. Silicon Valley. Dog training in Las Vegas. Coaching. Brand evangelism.
She takes the same tool kit and applies it in ways that fit each chapter.
The episode came from a simple idea. Reinvention is not a crisis. It is a skill. And Cathy walks through how to approach it with intention at any age.
At one point she talks about younger workers who may not be at the reinventing stage just yet, but they’re trying to figure out their path. She says:
“If you’re just out of school or you’re a couple years out of school, you’ve had a couple of jobs and you’re like, don’t just swing like Tarzan and grab the next vine and swing on it. Be intentional about it.”
She also gives a practical framework for anyone doing this work. She still prefers pen and paper. Write down everything you are good at, she says. Then circle the things you enjoy. Then write a second list of everything you avoid. Ask why. Is it because you are not confident in that skill. Or is there something else in the way. It is basic. It is honest. And it works.
We also talked about AI and how the tool can be used for career navigation. She uses AI in parts of her process. She asks it to help her categorize skills and see patterns. She asks it to recommend job titles that align with those patterns. She even asks it to point out the lines in her resume that matter most.
But she is firm on one point. AI cannot replace your voice. She says:
“Do not generate your resume using AI. Use AI to give you bullet points, to give you guidelines, and then be a human and talk like a person.”
Our conversation also covered boundaries. That theme comes up often in leadership circles around here, yet it tends to get treated as a soft skill. Cathy explains why boundaries create freedom.
Clarity, communication and consistency are what allow people to take real risks. These factors are what help teams function in fast moving environments. They are also what help individuals make decisions when everything around them feels uncertain.
This episode is different from others I have posted in recent months, but it felt right. A lot of founders, operators, and investors in the Bay Area are thinking about how to shift gears. Some by choice. Some because the market forced it. Reinvention is possible. It also takes structure and intention, which Cathy explains better than anyone.
You can listen to our full conversation on The Venture Variety Show, available on YouTube, as well as Apple Podcasts and Spotify.
If this resonates, pass it on to someone who’s facing similar issues.
