This letter from Jessie Shipman is part of Pavilion’s International Women’s Day 2025 collection, where the women of Pavilion share heartfelt letters to their younger selves. Through these reflections, they explore the lessons, challenges, and defining moments that have shaped their careers. Read more inspiring stories here.
Dear Jessie,
You’ve always known that mastery is the goal, not perfection. That showing up every day, adjusting to the wind, recalibrating, and taking the shot, even when you miss, is the only way forward. You’ve embraced that journey, even when the target kept moving, even when others doubted you, even when the road felt impossibly long.
I want you to remember:
You don’t have to prove your worth before you begin. You already are enough.
You don’t have to do it all alone. The right people will stand beside you.
Failure isn’t the opposite of success, it’s the foundation of it.
You have always been the kind of person who steps into the unknown and figures it out along the way. That grit, that resilience, that unshakable belief in your own ability to learn will be the very thing that builds your company, shapes your leadership, and inspires the people around you.
You will face rejection. The world will tell you to wait your turn, to meet another arbitrary milestone before you’re taken seriously. But you will keep pushing. You will rewrite the rules. You will take the shot again and again until one day, you realize you’re not just aiming at the target—you are the archer, fully in control of the bow.
And through it all, your children will watch. Not as a burden you carry, but as witnesses to what’s possible. They will see a mother who chases ambition with joy, who leads with fire, and who never shrinks herself to fit someone else’s expectations. They will know they can do anything because you did.
So keep going, Jessie. Keep showing up. Keep taking the shot. Ever onward, almost.
With love,
Jessie
The Women of Pavilion Community is a dynamic subcommunity of Pavilion dedicated to fostering belonging, knowledge-sharing, and professional growth for women in go-to-market. Led by Anne Pao, Founder and CEO of Ignite Consulting, and Lindsay Tjepkema, Founder and CEO of Human Brands Win, this group empowers members to break barriers, advocate for themselves authentically, and advance both personally and professionally through curated content, exclusive events, and a supportive network.
Curious to learn more? Explore Pavilion membership.
