INTERVIEW | Make Money with a Comeback, feat. Yasmine Cheyenne
Yasmin Cheyenne is a three-time HarperOne author and Today Show wellness expert who has guided hundreds of thousands of people back to their authentic selves through her writing, workshops, and teachings. After serving five years in the Air Force and working in the JAG (legal) department, Yasmin spent nearly a decade balancing a government job with her growing coaching and writing business before making the leap to full-time entrepreneurship in 2021—just days before the Today Show reached out for her first major media appearance.
On this episode we talk about:
The strategic decision-making process behind leaving a stable nine-to-five job to pursue entrepreneurship full-time
Why seeing a financial advisor before quitting your job is essential, even if you think you can't afford one
The difference between setting healthy boundaries and becoming unreasonably selfish
How reconnecting with your inner child can help you rediscover what you truly want from life
The concept of the "comeback era" and why midlife discomfort is actually a gift, not a crisis
Top 3 Takeaways
Do the human work before making the leap - Consult a financial advisor (many banks offer this free), calculate all expenses including taxes and health insurance, and ensure your business income can sustain your entire family's needs—not just your current bills. Don't make major career decisions from overwhelm or sleep deprivation.
Consider whether your passion can handle the pressure of paying bills - Some people love their creative work but don't want it to be the thing they rely on financially, as it changes the relationship with their gift. Be honest with yourself about whether you can emotionally handle your passion becoming your primary income source.
Learn from children's natural boundaries - Kids have no problem saying no to things they don't want to do, even when it would help someone else. While adults can't be completely unreasonable, reconnecting with that willingness to disappoint others occasionally helps you identify where you've been people-pleasing at your own expense.
Notable Quotes
"I knew that I was not going to take on hundreds of thousands of dollars of debt in an economy where people were not being hired. And so that's where entrepreneurship kind of became the only option for me. It felt like if there's so much of a risk here, then I might as well take the risk on myself."
"I want you to follow those things [like gut feelings and dreams], but I also want you to do your human work, which is the numbers. And so we have to make decisions from both places."
"To feel that discomfort is actually a gift and it's an opportunity to explore how you can make the changes that you want. I think it's actually an opportunity for a comeback."
Connect with Yasmin Cheyenne:
Instagram: @yasmincheyenne
Website: https://yasminecheyenne.com/
Book: The Comeback Era pre-order now for May 18th!
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