What if the thing keeping you from your next level is not lack of skill, but the fear of getting it wrong?

In this episode of The Pick Now Podcast, Jeff Munn sits down with Brittany Greenfield, founder of Wabbi and host of the Good Enough podcast, for a conversation about entrepreneurship, leadership, founder pressure, perfectionism, and learning to move before everything feels certain.

Brittany shares how she moved from building companies inside larger organizations to founding her own software security company. She talks about the importance of doing the uncomfortable founder work early, including making the calls, hearing customer feedback directly, and learning the value of the product before handing that work off to a sales team.

Together, Jeff and Brittany explore why successful leaders often forget that they are already good enough. As responsibility grows, so does the pressure to make every decision perfectly. But that pressure can lead to overthinking, paralysis, and fear-based leadership. This conversation is a reminder that growth does not come from endless analysis. It comes from putting something into the world, learning from the response, and separating your self-worth from the outcome.

In this episode:

• Why founders need to hear customer feedback themselves
• How early uncomfortable calls shape the value of a company
• Why leaders forget they are already good enough
• How success can create more pressure and perfectionism
• Why doing something beats analyzing forever
• How to separate challenge from self-worth
• Why fear does not make anybody better

If you have ever felt the weight of needing to get every decision right, this episode will help you loosen the grip, take the next step, and remember that progress comes from movement, not perfection.

Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.