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I’m in Vegas this weekend, and naturally I can’t help but think about gambling and taking risks; not just in cards and dice, but in life.

I don’t recommend treating your workplace like a casino, but there is a lot you can learn about life from gambling. Probability, strategy, knowing “when to hold ‘em and when to fold ‘em”. And maybe most importantly, recognizing that any reward you might seek comes with some level of risk.

This week is your reminder that success rarely comes from waiting. It comes from betting on yourself. Not recklessly, but bravely.

What’s inside:

• Maybe it’s time to play your cards

• Not taking a chance, worse than failing?

• Life is a game of chance; you choose which one

• Roll the dice on some great Rung Breaks

• Make one small bet this week

Main Idea

Risk has a bad reputation. We’re taught to associate it with recklessness, with failure, with loss. Risk taking is only for other people, for the bold, the wealthy, not us. The safe, steady, systematic path up the structured ladder. That is the right way, right?

But the truth is, if you’re chasing something meaningful, whether it is starting a business, shifting careers, making art, writing the book, launching a product, there’s no version of that path that doesn’t involve risk. No version that feels 100% safe. And honestly? If it did feel safe, it probably wouldn’t change your life.

Taking a chance on yourself will always feel scary. The odds are never perfect. That’s the point. Gambling on yourself isn’t about throwing caution to the wind. It’s about understanding that playing it safe can be its own form of danger. The danger of wasting years doing work that doesn’t light you up. The danger of building a life you don’t actually want, just because it looks good on paper. The danger of regret.

You don’t need to go all in tomorrow. But you do need to place a bet. On your growth. Your potential. Your gut instinct. Even a small, uncomfortable action (starting the thing, sending the email, making the ask) begins to shift momentum in your favor.

Playing not to lose is a strategy for survival.
Betting on yourself is a strategy for living.

Time to put your cards on the table!

Ditch the Metrics

Burn the business scorecard – focus on what matters!

The Metric:
A survey of over 1,000 professionals revealed that 78% regret not taking more career risks . This was ranked as the third most common regret among respondents, after only “Not taking more initiative” and “Not having enough mentorship”.

Reframe It:
We often treat fear of failure as the enemy. But regret for not even trying? That cuts deeper. When asked, most professionals say they wish they'd taken more chances, even if those bets didn't pay off. It’s a signal that risk aversion is holding you back far more than failure ever could.

Ditch It:
Stop letting fear hijack your future. Small bets can pay exponential returns. When the odds don’t feel perfect, don’t fold. Play your hand. Bad poker analogy!

Reframe This

 A quick thought-flip to help shift how you see your work, your worth, or your path.

Old Belief: Life is like playing poker. You should wait for the best possible hand before making a big bet.

New Perspective: Life is like playing craps. Make consistent, small bets on yourself with each roll of the dice. Or maybe it’s more like blackjack? Roulette? Point is we are almost never dealt a perfect hand, but we are given many opportunities if we are ready for them!

Rung Breaks

A curated mix of tools, links, books, and ideas to help you step off the ladder and into your own path.

📚 Book: Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke - who better to guide you through high pressure decisions and taking calculated risks than a former poker champion.

🎧 Podcast Episode: Against the Rules with Michael Lewis featuring Gambler Billy Walters - Moneyball and Big Short author Michael Short sits down with famed gambler to talk sports betting and life lessons

🛠️ Tool: Start Your Side Hustle (Shopify Blog) - Free guide that walks you through setting up a small project with minimal upfront cost and low risk; perfect for taking the first $100 step.

✍️ Read: Why it’s Risky to be Risk Averse by Anne Kreamer

🎨 Inspiration: Sh*t Luck Painting - And it’s for sale!

Your Move

A reflection and challenge to help you break out of autopilot and make real change.

Reflection Prompt:

Challenge:

Until Next Time…

Vegas or not, life rewards those who take the leap.
Bet on yourself. You’re the best odds you’ve got.

See you off the ladder.

— Sean Sirianni
Founder, Off the Ladder

P.S. if I hit the jackpot, consider this my final farewell

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