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The Art of Manliness

How to Use Probability Hacking to Achieve Your Goals

The Art of Manliness

The Art of Manliness

Education, Philosophy, Society & Culture

4.714.5K Ratings

🗓️ 30 December 2025

⏱️ 55 minutes

🧾️ Download transcript

Summary

Most of us chase goals — starting a business, running a marathon, getting a promotion — without ever asking: What are the actual odds this will work?

My guest today says those odds aren’t just graspable — they’re hackable.

Kyle Austin Young is a strategy consultant and the author of Success Is a Numbers Game. He argues that every goal comes with a hidden probability of success or failure, and by thinking strategically — rather than just hoping for the best — you can tilt the odds in your favor.

In the first part of our conversation, Kyle explains the three common ways people pursue goals and their potential downsides. We then unpack how to approach your goals through probability hacking. We discuss how to spot the weak links in your plan, how to map out a “success diagram” that helps you avoid common pitfalls and pursue goals more intelligently, and how to use these same principles to know when you should quit a goal.


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Transcript

Click on a timestamp to play from that location

0:00.0

So earlier this year, Kate and I started a substack. It's called Dying Breed. It's a place where we can write about things that wouldn't be a good fit for art of manliness, but we wanted to write about and share anyway. Each week, we published two articles there. First, there's Kate's wonderful short Sunday firesides. It's a great way to start your week off with some reflection. And then we have a longer form article that explores topics like luck, success,

0:21.8

media theory, the intersection between technology and life, how to use technology in a meaningful

0:26.0

way. When you subscribe, you get access to over 300 articles in the archive, including all of

0:29.9

Kate's Sunday firesides, plus articles like 20 lessons from 20 years of marriage, co-written by

0:34.5

Kate and I, what Kickagard can tell us why professional sports in life

0:37.8

can seem so boring. We have articles on luck, what philosophers think about luck, a tour of our home office, and a lot, lot more. Plus, when you subscribe, you can comment and connect directly with Kate and I and other Dying Breed readers. It's just $5 a month or $50 a year, and your subscription is a great way to support the work we do at Art of Manliness.

0:56.3

We'd love to see you there on Dying Breed.

0:58.1

Head to... It's just $5 a month or $50 a year, and your subscription is a great way to support the work we do at Art of Manliness.

0:56.2

We'd love to see you there on Dyingbreed.

1:08.0

Head to Dyingbreed.net and become a member today. That's Dyingbreed.net. Thanks so much for your continued support. We really appreciate you. Hey, this is Brett. before we get today's show,

1:09.4

wanted to let you know that right now we have enrollment going on

1:10.5

for a winter cohort of the strenuous life.

1:13.1

If you're looking for a meaningful way

1:14.4

to start the new year, one that actually sets the tone for the kind of man you want to be in 2026, the strenuous life is it. Enrollment is now open and closes on January 1st. The strenuous life is an online program that we created to help you put into action all the things we've been talking about on the A1 podcast and over on the Art of Manliness website. When you sign up, you're going to be put into a 12-week boot camp that gives you real structure to build discipline, develop practical skills, and take action starting day one. There's 50 different badges based around 50 different skills that you can earn, and it gives you direction toward developing some practical skills. You're going to get weekly challenges that push you physically, mentally, and socially, plus access to community of like-minded men who are serious about becoming more capable, grounded, and useful. If you've ever said to yourself, this year I want to live with more purpose, the Strenuous Life can help with that. Go to straneouslife.co. to sign up. Again, that's strenuouslife.

2:01.4

C.O.

2:02.5

Enrollment closes January 1st

2:04.0

and the challenge kicks off on January 3rd.

2:06.6

Hope to see you there on the Strenuous Life.

2:07.8

Again, it's striniuslife.co. Brett McKay here and welcome to another edition of the Art of Manliness podcast.

2:21.7

Most of us chase goals, starting a business, running a marathon, getting a promotion.

2:26.3

Without ever asking, what are the actual odds this will work?

2:29.6

My guest today says those odds aren't just graspable, they're hackable.

...

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