From an anxious, entry-level employee to Google executive and now New York Times bestselling author, I'm passionate about helping you achieve your personal
& professional goals, unapologetically.
Hi, I'm Jenny
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Ever feel weird sharing your career goals outside of a formal meeting?
I get it.
But let me tell you a story that might change your mind.
A few years ago, I was at a local street fair.
My toddler was busy climbing into a bouncy castle when I ran into the head of Google Boulder’s office, where the company has a significant footprint.
We barely knew each other, but we started chatting.
Suddenly, I blurted out my career ambition: I wanted to be the Boulder site co-lead with her.
Cue immediate imposter syndrome.
What was I thinking?
Why did I say that?
It’s the weekend! Keep it light!
But I’ll never forget what happened next:
As we wrapped up our conversation and she started to walk away, she turned back, smiled, and said, “Thank you for telling me your ambitions.”
That moment taught me something critical:
People want to know your career goals.
It doesn’t have to be formal and take you 3 hours of prep.
It can be casual and take you 3 seconds of courage.
The Problem
Most of us hesitate to share our career goals with leaders or colleagues because it feels awkward or out of place.
We worry that we’ll come off as pushy or overconfident—especially in casual settings. Or worse, we feel like we need to spend 3 weeks perfecting a 17-slide deck to have a super official, buttoned-up career conversation.
But if people don’t know where you want to go, how can they help you get there?
The Big Small Thing
Here’s how to share your career goals in a way that feels natural, not forced, and gets the right people on board with your journey:
1. In a casual conversation:
“By the way, something I’ve been thinking about is how I can grow into a [specific role] in the future. I’d love to hear your thoughts on how I might get there.”
Why it works: It’s simple, conversational, and doesn’t feel out of place—even if you’re not in a formal setting
2. In a 1:1 with your manager:
“Looking ahead, I’ve been reflecting on my career goals, and I’m interested in pursuing a leadership position in the next 1-2 years. I’d love your advice on how I can best prepare for that and your partnership on what projects will enable the right visibility for this.”
Why it works: This frames your ambition with a timeline and invites guidance, making it a collaborative conversation.
3. When networking:
“One of my goals is to grow into [specific role], and I’d love to hear how you approached that transition in your career.”
Why it works: People love talking about their own experiences. You’re seeking their insights and making it a two-way conversation.
4. In an unexpected moment (like a street fair!):
“You know, one of my long-term goals is to work closely with you on [specific project or role]. I’d love to chat more about how I could contribute in that capacity.”
Why it works: It’s direct but framed in a way that shows you’re eager to contribute and collaborate.
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How This Helps You Chase What You Want
When you share your career goals, you’re making it easier for people to support you.
It’s not about being pushy. It’s about being clear with the people who can help you get where you want to go.
So, don’t be afraid to share your ambitions—even in unexpected places.
It might just be the key to your next big opportunity.
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