This letter from Randi Deckard 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 Younger Randi,
You don’t know this yet, but life isn’t a formula. It’s not a sequence of perfect, calculated steps that lead neatly from one milestone to the next. Right now, you think that following the rules, doing what’s expected, and staying in your lane will guarantee success and security. But let me tell you a secret: the real magic happens when you step off the predictable path and carve out your own.
One day, you’ll look back and realize that the things that scared you the most—the uncertain decisions, the unexpected detours, the moments that made no sense at the time—were the ones that shaped you into the fearless, resilient woman you are meant to be.
You’ll leave behind the safety of what you know. You’ll chase opportunities that others don’t understand. You’ll take risks that will make people shake their heads. And you will fail. More than once. But each failure will teach you something you couldn’t have learned any other way. Each setback will be data—an experiment with an unexpected outcome that will help you refine, adjust, and grow.
You’ll move to a new country where you know no one in your early twenties. You’ll take jobs that challenge you in ways you never imagined. You’ll walk away from the stability of a career that you worked so hard to build, only to find that success was never about climbing a ladder—it was about the climb itself. You’ll pivot more times than you can count, reinventing yourself again and again. And you’ll learn that no single version of you is final—you are always evolving.
There will be moments when imposter syndrome creeps in, whispering that you don’t belong, that you’re not enough. You’ll be tempted to dim your light, to shrink yourself to fit into spaces that were never meant for you. Don’t. Instead, stand tall. Take up space. Own your brilliance. You have a voice that is meant to be heard, a story that is meant to be told, and an impact that is meant to be made.
And let’s talk about fear—because it will show up often. Fear will try to convince you that it’s safer to stay put, to not take the leap. But here’s what you need to remember: fear is just a sign that you’re on the edge of something great. Lean into it. Feel it, acknowledge it, and then do the damn thing anyway.
You won't let a toxic boss saying you aren't VP of Sales material stop you!
You’ll learn to trust yourself. To rely on your instincts, your intelligence, and your ability to figure things out along the way. You’ll embrace the mindset of experimentation, treating every challenge as a chance to refine your approach rather than a reason to quit. And through it all, you’ll cultivate resilience—not just the ability to bounce back, but the confidence to move forward with even more clarity and courage.
You'll go on to be VP of Sales X2, SVP of Growth and CRO advisor to digital health startups.
Most importantly, you’ll find your purpose and your voice—not in a job title or a paycheck, but in the lives you touch, the people you uplift, and the transformation you help others ignite. You’ll realize that success isn’t about reaching a destination—it’s about showing up, every day, with intention, authenticity, and an unwavering commitment to growth.
So, keep going. Keep pushing boundaries. Keep believing in yourself, even when it feels impossible. Because the story you are writing is one of strength, reinvention, and fearless transformation.
With love and a knowing smile,
Your Future Self, aka Randi's Okay with Not Being for Everyone!
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.
