It’s Not All Hard Luck with Shay Skinner

In her late teens and early twenties, Shay Skinner was disowned from her family. She struggled with crushing mental illness, which ultimately culminated in a suicide attempt that left her in financial ruin. From this dismal situation, Shay filed for bankruptcy and began a long and fruitful climb toward being whole again. How can we summon the courage to take such measures of personal accountability?

Shay Skinner: An Introduction

Today’s guest on episode 47 is Shay Skinner. Shay came to me with a question for a Q&A episode that I felt was far too intriguing to address in short form. What I’ve found in four years of running this platform is that it’s often easy to find yourself preaching to the choir, in a sense. Perhaps folks are new to some of these methods, but below the surface, most who are successful in their pursuit of financial independence come with some solid ground work already in place. At the foundation is often a supportive family.

Shay wrote to me about her history of near financial ruin and eventual bankruptcy. Upon follow-up, it occurred to me that her story was so different from the typical money nerd that I had to have her on. Most importantly, I think her history is far more relatable to many in the general public. Shay did not have a solid support system from her family. In fact, at certain periods members of her family sought to actively undermine her wellbeing. From this stemmed a serious downward spiral in mental health, ultimately culminating in a suicide attempt.

But we are not just here to discuss hard-luck stories.

What drew me to Shay’s narrative is her accountability for an absolutely miserable situation. While she was certainly not to blame for her circumstances, she took a point-forward look at her life. She filed for bankruptcy, and began a slow process of climbing out of debt and using the same old methods of saving and investing to put herself on solid financial footing.

This is a story of redemption, and I’m happy to bring it to you today. I want to thank Shay for her willingness to discuss deeply personal and hard topics.

Topics Discussed with Shay Skinner

  • Shay’s introduction to rock climbing as a positive life force
  • How Shay was disowned by her family at age 19, leading to a mental health crisis
  • Why Shay came to bankruptcy as a clean start
  • The shame of bankruptcy and the requirements for filing
  • Discovering a path towards financial independence from a coworker
  • Comparison culture and hidden ways it impacts our spending
  • Shay’s psychological struggles with stock market volatility
  • The importance of community
  • Money relationships with a partner
  • How Shay has gone from crushing debt to saving 50% of her income!
  • Why Shay wants financial independence but doesn’t want to stop working
  • Why women resist early retirement more than men
  • The importance of discussing money
  • The pros and cons of a college education
  • So much more!
Shay Skinner on Flight Time (5.12a), Indian Creek, UT (photo: Sagar Gondalia)
Shay Skinner on Flight Time (5.12a), Indian Creek, UT (photo: Sagar Gondalia)
Shay Skinner and Hunter on Royal Flush (5.9), near Frisco, CO.
Shay Skinner and Hunter on Royal Flush (5.9), near Frisco, CO.
Shay Skinner following Transformation (5.11), Monitor Rock, Independence Pass.
Shay Skinner following Transformation (5.11), Monitor Rock, Independence Pass.
Longs Canyon, UT - Photography by Shay Skinner.
Longs Canyon, UT – Photography by Shay Skinner.

Posts on Health Savings Accounts

Part 2: The CC Family Investing Strategy

Your 2021 Guide To Actually Saving Real Money

EP 22: Your Questions Answered: Volume 4

QA7: Financial Freedom Fast-Tracks and Climbing Plateau Busters

Other Related Posts

Personal Finance: Not Very Sexy, Huh?

This is the Wild Ride We Signed Up For

Why Trying to Quit My Job (Sort of) Made It Better

Financial Advisor: Who Needs One?

EP 39: Peter Beal: Can You Afford to Be Sponsored?

A list of all posts and podcast episodes can be found here.

Shay’s Charitable Giving

NAMI Boulder County

The Shane Thurston Foundation

Books Recommended by Shay Skinner

The Simple Path to Wealth: Your road map to financial independence and a rich, free life (JL Collins)

Burnout: The Secret to Unlocking the Stress Cycle (Emily Nagoski, Amelia Nagoski)

The Sisters of Auschwitz: The True Story of Two Jewish Sisters’ Resistance in the Heart of Nazi Territory (Roxane van Iperen)

Metabolical: The Lure and the Lies of Processed Food, Nutrition, and Modern Medicine (Robert H. Lustig)

Life Is Hard: How Philosophy Can Help Us Find Our Way (Kieran Setiya)

A Beginner’s Guide to the End: Practical Advice for Living Life and Facing Death (Dr. BJ Miller, Shoshana Berger)


Remember, the best laid plans mean nothing if you can’t take action today. Have questions? Need some feedback? Hit us up on the contact page.

If you enjoyed this post, please subscribe here for much, much more. And please, send this to someone who might enjoy or benefit from this content.

Support this free project:

Subscribe to the weekly newsletter and receive a FREE spreadsheet for tracking spending, income, and net worth!

* indicates required

Thanks guys, see you next week.

Affiliate links are used on this page. If you choose to purchase a linked product, you will incur no extra charges, but we will receive a tiny-baby portion of the sale. Those very small proceeds help us keep the digital lights on around here. We wouldn’t link to a product we wouldn’t buy ourselves. Tis all!

What say you friend?