From Playing It Safe to All-In: The Poker Strategy Every Person Should Use at Work

In this week’s episode of UnCeiling You, I had the absolute pleasure of sitting down with Elen Leikind, author of Poker Woman and creator of the BOLD negotiation system. And wow—this one is packed with truth bombs.

We talked about what it really means to "play it safe"—and why playing it safe is often the most dangerous move you can make.

💡 Elen said it best:

“Playing it safe is really just playing not to lose.”

Whether you're staying silent in meetings, waiting to be promoted, or hoping your hard work gets noticed… you're in the game. You just might be playing it passively.

Here's what we uncovered:

• The hidden cost of playing it safe (spoiler: it’s not just missed promotions)
• Why visibility and relationships matter as much as performance
• How to navigate office politics without losing yourself
• When to go all in, when to bluff, and when to fold
• How to reframe assertiveness as a leadership strength, not a liability

👀 One of my favorite moments? Elen’s story about asking her boss if she’d get promoted. Her boss’s response:

“Did you ask for it?”

At first, she was furious. Years later, she saw it for what it was—the best advice she ever got.

This episode is your reminder to stop waiting for permission. Know your worth. Ask for what you want. And play the game with intention.

🎧 Listen now: 👉 You Are Your Best Bet: From Playing It Safe to All-In at Work

📚 Explore Elen’s book & course: 👉 PokerDivas.com

You are your best bet. Now go play to win.

—Natalie