Great story, Rob. I was just having a similar conversation with a wise old man using this same poker metaphor - not about careers, but about how we help people. I appreciate the opportunity to bring both together here.
I think the real difference isn’t just safe vs. bold. It’s percentage thinking.
In poker, you play the hand that wins 85% of the time, even though you’ll still lose sometimes. But smart players also know not to keep betting into a hand with no chance to improve.
Life works the same way. Whether it’s business, opportunities, or helping others, we’re always putting chips on the table - our time, energy and resources. The skill is knowing:
Is this a high-percentage moment?
If yes - push chips.
If not - fold without guilt.
I’ll be honest, I haven’t mastered this. My instinct is usually, “Sure, I’ll carry the whole hand.” I’m still learning where the odds actually justify the bet.
Boldness gets attention.
Percentage decisions build careers, judgment, boundaries and the energy to keep showing up where it truly matters.
That’s the real skill in life and leadership - not “always say yes” (bold) or “never get involved,” (safe) but knowing when your effort actually creates forward movement (%). ❤️
poker skills at the table involve a feel. You feel or know the best action at the right time. In life, it’s knowing what to say or not and knowing the right action to take at the right time that help you win.
I love that - “feel” is such a good way to put it. The percentages guide you, but experience sharpens your ability to recognize the moment in real time.
That’s probably where the real growth happens - learning to trust both the math and the feel.
That Joey Knish vs Mike contrast hit — “play it safe” can quietly become a life sentence.
I love the way you tie taking shots to communication at the “big tables,” because the risk is often saying the thing you actually mean (or asking the real question), not just staying agreeable.
Curious: when you’re coaching someone to “take a shot,” what’s your favorite *small* move (one sentence) that changes the whole table dynamic?
You ask a great question and I love your line, "play it safe" can quietly become a life sentence.
I approach small moves by having multiple options. Because each table is different. Our options revolve around our client's goals. Then we work on a short, punchy sentence or two to step into the spotlight. Then we work on different ways to make that point - serious, humor, curveball.
Because in that moment when you take your shot the best way to succeed is trusting yourself to read the room
Great story, Rob. I was just having a similar conversation with a wise old man using this same poker metaphor - not about careers, but about how we help people. I appreciate the opportunity to bring both together here.
I think the real difference isn’t just safe vs. bold. It’s percentage thinking.
In poker, you play the hand that wins 85% of the time, even though you’ll still lose sometimes. But smart players also know not to keep betting into a hand with no chance to improve.
Life works the same way. Whether it’s business, opportunities, or helping others, we’re always putting chips on the table - our time, energy and resources. The skill is knowing:
Is this a high-percentage moment?
If yes - push chips.
If not - fold without guilt.
I’ll be honest, I haven’t mastered this. My instinct is usually, “Sure, I’ll carry the whole hand.” I’m still learning where the odds actually justify the bet.
Boldness gets attention.
Percentage decisions build careers, judgment, boundaries and the energy to keep showing up where it truly matters.
That’s the real skill in life and leadership - not “always say yes” (bold) or “never get involved,” (safe) but knowing when your effort actually creates forward movement (%). ❤️
I love this, Becky. Great comment, thank you.
poker skills at the table involve a feel. You feel or know the best action at the right time. In life, it’s knowing what to say or not and knowing the right action to take at the right time that help you win.
I love that - “feel” is such a good way to put it. The percentages guide you, but experience sharpens your ability to recognize the moment in real time.
That’s probably where the real growth happens - learning to trust both the math and the feel.
That Joey Knish vs Mike contrast hit — “play it safe” can quietly become a life sentence.
I love the way you tie taking shots to communication at the “big tables,” because the risk is often saying the thing you actually mean (or asking the real question), not just staying agreeable.
Curious: when you’re coaching someone to “take a shot,” what’s your favorite *small* move (one sentence) that changes the whole table dynamic?
You ask a great question and I love your line, "play it safe" can quietly become a life sentence.
I approach small moves by having multiple options. Because each table is different. Our options revolve around our client's goals. Then we work on a short, punchy sentence or two to step into the spotlight. Then we work on different ways to make that point - serious, humor, curveball.
Because in that moment when you take your shot the best way to succeed is trusting yourself to read the room