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Episode 467: Caregiving for Loved Ones & Entrepreneurship While Building Financial Freedom w/ Keisha Wilson

Journey To Launch

Release Date: 02/25/2026

Episode 475: How Following Your Intuition Can Unlock Freedom and Unexpected Opportunities w/ Damali Alexander show art Episode 475: How Following Your Intuition Can Unlock Freedom and Unexpected Opportunities w/ Damali Alexander

Journey To Launch

Have you ever felt a pull toward something that didn’t quite make sense logically, but you couldn’t ignore it? That inner nudge to try something new, take a risk, or step outside the expected path? In this episode, I sit down with Damali Alexander, someone I’ve known for years and always admired for the way she moves through life with intention, courage, and trust in herself. From starting as a teacher to building multiple businesses, investing in real estate, and even moving to Brazil, Damali shares how following her intuition has shaped her journey. We talk about what it really looks...

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Journey To Launch

From homeless to bartending at Coyote Ugly, today’s guest has gone through it all when it comes to working the service industry. Barbara Sloan is author of “Tipped: The Life Changing Guide to Financial Freedom For Waitresses, Bartenders, Strippers and All Other Service Industry Professionals,” and a personal finance expert.  She’s spent two decades working in every imaginable position in the service industry, in addition to owning and running a woman-owned construction company in Manhattan. Now, she helps other service industry professionals map their way to financial...

info_outline Episode 472: How I'm Unlearning the Need to Hustle & Giving Myself Permission to Make My Own “Rules Episode 472: How I'm Unlearning the Need to Hustle & Giving Myself Permission to Make My Own “Rules"

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Have you ever caught yourself choosing work over something that actually matters even after you’ve done everything “right”? That’s exactly what happened to me, and it made me pause in a way I didn’t expect. When my podcast guest cancelled, I decided to record a solo episode instead. Shortly after, I received a call from the school nurse that my son wasn’t feeling well and needed to be picked up. But instead of immediately going to get him, my first thought was whether I could still get some work done. That moment stopped me. Because I’ve intentionally built a life with...

info_outline Episode 471: Why He Quit His $100K Engineering Job to Work at McDonald's w/ Drew Lee show art Episode 471: Why He Quit His $100K Engineering Job to Work at McDonald's w/ Drew Lee

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In this episode, I sit down with Drew Lee, a former engineer turned personal finance content creator, who made a bold decision to walk away from a six figure career more than once to pursue a life of flexibility and purpose.  Drew reached Coast FI, where your investments grow on their own to fund retirement, in his late 20s, and shares how that freedom changed the way he thinks about work. We talk about the realities behind quitting a stable job, navigating uncertainty, and what it really takes to pursue your passions, especially when you have a family. Drew also opens up about working...

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info_outline Episode 469- How to Parent Like a Millionaire Without Being One with Kristy Shen & Bryce Leung show art Episode 469- How to Parent Like a Millionaire Without Being One with Kristy Shen & Bryce Leung

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info_outline Episode 468: A Money System That Works When Life Falls Apart with Sahirenys Pierce show art Episode 468: A Money System That Works When Life Falls Apart with Sahirenys Pierce

Journey To Launch

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info_outline Episode 467: Caregiving for Loved Ones & Entrepreneurship While Building Financial Freedom w/ Keisha Wilson show art Episode 467: Caregiving for Loved Ones & Entrepreneurship While Building Financial Freedom w/ Keisha Wilson

Journey To Launch

This week on the Journey to Launch Podcast, I’m joined by healthcare compliance expert and entrepreneur Keisha Wilson for a powerful conversation about career pivots, betting on yourself, caregiving, and building financial flexibility before you realize you’ll need it. Keisha shares how she transitioned from corporate leadership into entrepreneurship, how that decision gave her the flexibility to care for her mother through stage four cancer and a devastating home explosion, and why preparation, advocacy, and hard financial conversations matter more than we think. This episode is about...

info_outline Episode 466- Balancing Corporate Life While Owning Property in Jamaica & Running an Airbnb w/ Leanne Pinkard show art Episode 466- Balancing Corporate Life While Owning Property in Jamaica & Running an Airbnb w/ Leanne Pinkard

Journey To Launch

In this episode, I chat with Lee-Ann Pinkard, who was born and raised in Kingston, Jamaica, and later moved to the U.S. for college at Howard University. She built a career in construction project management and, years later, purchased a beachside property in Jamaica that she now runs as a short-term rental, a property I personally had the pleasure of staying in. We explore what it really takes to buy property in Jamaica, the realities of managing an Airbnb from abroad, how she balances corporate life, motherhood and her long-term plan to retire back home. In this episode, we discuss: ...

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This week on the Journey to Launch Podcast, I’m joined by healthcare compliance expert and entrepreneur Keisha Wilson for a powerful conversation about career pivots, betting on yourself, caregiving, and building financial flexibility before you realize you’ll need it.

Keisha shares how she transitioned from corporate leadership into entrepreneurship, how that decision gave her the flexibility to care for her mother through stage four cancer and a devastating home explosion, and why preparation, advocacy, and hard financial conversations matter more than we think. This episode is about resilience, faith, and creating options that protect your peace and your family.

In This Episode, Keisha Shares:

  • How medical coding became a high-demand, lucrative career path and why skill-building creates long-term flexibility 
  • What it really takes to leave a steady paycheck and build a consulting business from scratch 
  • The emotional and financial realities of caregiving and why advocacy and second medical opinions matter 
  • The importance of wills, healthcare proxies, power of attorney, and financial transparency before crisis hits 
  • Why building freedom and flexibility now can prepare you for life’s unexpected turns

What’s New in the Paperback Edition of Your Journey to Financial Freedom

  • A bonus chapter: When Life Happens: Staying on the Path to Financial Freedom Through Setbacks, Shifts, and Uncertainty
  • A book club and discussion guide with prompts, exercises, and action steps
  • Updated corrections from the original hardcover
  • Exclusive bonuses when you purchase the paperback, including:
    • The Fire Starter Course
    • The Find Your FIRE Number Worksheet

Other related blog posts/links mentioned in this episode:

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