About Us

We're Lisa Sanchez and Diana Kimball—two writers who'd rather talk. After living together for three years in college, following each other across three cities and two continents, and seeing each other through the best and worst of our twenties, a podcast was the next logical step in our friendship.

Should We began with Post-Its, an iPhone in a cup, and an insatiable desire to talk things out together. Our experiment unfolded into a whole season, then a Kickstarter project and a decision to go big.

Now with over 30 episodes and an event behind us, we just keep redefining "big." We found our own voices in Season One, then introduced the voices of leaders we admire in Season Two. In Season Three, we're telling secrets that overturn expectations about what it means to lead.

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Diana Kimball Berlin

Diana Kimball lives in San Francisco and works as a product manager. She’s known for bringing people together on the internet and creating tools they use every day. She doesn’t believe in forever projects, but she does believe in Swedish shoes.

dianaberlin.com    @dianakimball


Lisa Sanchez

Lisa Sanchez lives in San Francisco and works as a creative director. She loves starting new things and considering the tradeoffs. She’s lived in Boston, Atlanta, and Berlin. She believes that decisions are hard but experiments are fun.

lisasanchez.me    newsletter