Probability Hacking Your Goals: How To Diagram Any Goal To Improve Your Odds of Success, with Kyle Austin Young
Fri Sep 26 2025
Most of us have set a Big Goal at some point. Launch a business, write a book, run a marathon, eat less Goldfish crackers at midnight...and then promptly watched it crumble like said crackers at the bottom of the bag.
The problem isn’t that we’re lazy or unserious. The problem is that we treat goals like vague wishes instead of math problems. Math problems?! Oh no! Don't run away. Don't worry. This isn't going to stir up any of your high school algebra PTSD, I promise.
Enter: Kyle Austin Young. Kyle is not only an award-winning strategy consultant and writer for heavyweights like Harvard Business Review, Fast Company, and Psychology Today, he’s also the author of Success is A Numbers Game, a book that argues: “hey, you can literally diagram your odds of success before you even start.”
On the latest episode of HerPaperRoute Podcast, Kyle sat down with me to talk about:
why most of us fail at big goals (spoiler: it’s in the math) how to map out the exact steps between you and success the underrated power of failing in front of your whiteboard instead of in front of your executive board plus his journey publishing a book with a traditional publishing house, and his PR tips to help you get more pitch emails read and replied to
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Most of us have set a Big Goal at some point. Launch a business, write a book, run a marathon, eat less Goldfish crackers at midnight...and then promptly watched it crumble like said crackers at the bottom of the bag. The problem isn’t that we’re lazy or unserious. The problem is that we treat goals like vague wishes instead of math problems. Math problems?! Oh no! Don't run away. Don't worry. This isn't going to stir up any of your high school algebra PTSD, I promise. Enter: Kyle Austin Young. Kyle is not only an award-winning strategy consultant and writer for heavyweights like Harvard Business Review, Fast Company, and Psychology Today, he’s also the author of Success is A Numbers Game, a book that argues: “hey, you can literally diagram your odds of success before you even start.” On the latest episode of HerPaperRoute Podcast, Kyle sat down with me to talk about: why most of us fail at big goals (spoiler: it’s in the math) how to map out the exact steps between you and success the underrated power of failing in front of your whiteboard instead of in front of your executive board plus his journey publishing a book with a traditional publishing house, and his PR tips to help you get more pitch emails read and replied to