Khiara Cureton once dreamed of becoming a doctor—but life had other plans. After realizing medicine wasn’t her true calling, she pivoted toward a master’s program that opened the door to a rewarding career in healthcare—and $120,000 in student loan debt.  But how to navigate her student debt was a problem for her future self.   

“Someday” came sooner than expected. While building a thriving wedding planning business on the side, Khiara became a single mom. Her son quickly became her motivation to build stability and create the kind of future she’d always envisioned. 

Today, Khiara is taking charge of her finances—tackling her student loans head-on and making steady progress toward a bright financial future for both of them. 

2:50 Khiara learns about the value of financial independence growing up. 

6:48 Khiara wrestles with big decisions—what to study and where to build her future. 

9:24 She accumulates over 100K in student loan debt, but frames this as a problem to be solved in the future. 

12:45 She starts a wedding planning business to bring in extra income. 

16:40 After her business closes, she launches two new ventures. 

19:24 Khiara shares her thoughts on the flow of money in the African-American community. 

21:14 She balances her own financial goals with those related to her son. 

23:23 She discusses her approach tackling her student loans. 

29:13 She speaks to her financial goals to save for travel experiences and philanthropy work. 

36:57 Our cohosts reflect on the themes from Khiara’s story. 

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For Lorrena Black, saving money when she was young didn’t come naturally. Raised by a hard-working single mother, she modeled a deep work ethic but struggled to save. When she joined the Army, her discipline and sense of duty grew — but her spending habits stayed the same.

Her real turning point came years later, during a short-lived career as a financial advisor. Helping others with their finances forced her to take a closer look at her own. Though she eventually pivoted her career in a new direction, the lessons she learned about budgeting, saving, and planning for the future finally began to click.

Today, Lorrena channels that hard-won wisdom into mentoring and leadership development, with a focus on serving veterans. She’s passionate about helping others unlock their potential — financially, personally, and professionally.

2:25 Lorrena’s upbringing influences her work ethic.

5:01 When she joins the military, she ends up spending all the money she makes.

7:58 She incurs some credit card debt in her 20s but eventually leverages her budget to pay it down.

12:01 She starts a career as a financial advisor and applies the teachings to her own life.

14:54 Lorrena retires from the army and loses some of her financial focus initially.

17:46 She launches a small business.

21:19 She strives to develop leaders, with a focus on veterans.

22:32 She talks about her goals related to her business, retirement and giving.

23:20 She shares her favorite money tip: pay yourself first. 

GreenPath Financial Service

If you’re interested in building healthy financial habits, paying down debt, or saving for what matters most, take a look at these free financial tools.

Jess Jackson grew up believing she was solidly middle class. But once she arrived at college, she realized many of her peers came from far wealthier backgrounds. Determined to keep up, she borrowed more than she should have—decisions that later became a heavy financial burden. 

Her journey has been one of jumping into new opportunities and learning through trial and error. She bought her first home at a young age, navigating plenty of financial growing pains along the way. Over time, those lessons fueled her growth into a successful business built around real estate investment. 

As her career has evolved, Jess has had to reinvent herself more than once. The path hasn’t been easy, but her persistence and resilience continue to drive her forward—and inspire her to create a better world for those around her. 

2:40 Jess reflects on how being around people of different financial means influenced her. 

7:09 When she attends the University of Michigan, she feels pressure to keep up with the Joneses. 

11:42 Her credit score prevents her from getting approved for housing while in a teaching program. 

12:56 She optimizes available resources as she gets her MBA. 

14:52 Jess buys her first house and learns a lot along the way. 

19:26 She learns a financial lesson related to her business and taxes. 

20:43 She balances her savings goals and student loan repayment goals. 

23:09 She discusses shame and ego and how this contributed to her stress. 

24:58 She experiences job loss and a subsequent mental breakdown but emerges in a better place. 

28:58 Jess shares some practical money tips. 

35:18 Our co-hosts reflect on the themes from Jess’ story.  

GreenPath Financial Service

GreenPath is a 60-year trusted national nonprofit, learn how GreenPath’s Debt Management Program can help you pay off your debt in 3-5 years, while helping you develop sound financial literacy.

As Evelyn grew up in an immigrant Cuban-American household, money was seldom discussed. Faced with mounting debt after a job loss and family medical expenses, she didn’t know where to turn. The debt piled up quickly, and bankruptcy started to feel like her only option. 

Looking for connection and answers, Evelyn shared her situation on social media. The support she received encouraged her to explore other solutions. 

That’s when she found GreenPath. With a customized plan and ongoing support, Evelyn is now working toward becoming debt-free. For the first time, she feels hopeful about building financial stability and a stronger future.  

2:26 Evelyn reflects on how her parents didn’t really talk about money growing up. 

4:13 She borrows a lot of money to cover living expenses during college. 

7:08 Job loss and her husband’s medical expenses end up affecting the family’s finances. 

10:06 She considers bankruptcy after her debt becomes overwhelming but ends up stumbling on a referral to GreenPath. 

12:24 She recounts the initial conversations she had with GreenPath and the relief she felt. 

18:32 She shares about her financial journey on social media. 

22:35 Evelyn discusses her approach to her student loans. 

24:08 She considers her future goals around debt, savings, and homeownership. 

27:06 She encourages others in similar situations to not navigate financial stress alone. 

28:47 Our co-hosts reflect on the themes in Evelyn’s story. 

GreenPath Financial Service

GreenPath is a 60-year trusted national nonprofit, learn how GreenPath’s Debt Management Program can help you pay off your debt in 3-5 years, while helping you develop sound financial literacy.

Emily grew up in a household where money was tight, shaping her mindset around finances as she entered adulthood. Eager to embrace life and support loved ones, she often found it hard to say no—leading to experiences she cherishes, but also to mounting debt she came to regret. 

After her boss suggested she reach out to GreenPath, Emily made the call—and felt immediate relief after speaking with a caring financial expert.

With GreenPath’s support, she transformed her approach to money and steadily paid down her debt. 

Years later, Emily is debt-free and looking toward the future with hope and excitement—dreaming of one day owning a cozy home down a quiet dirt road. 

2:19 Emily recalls how money was tight growing up and how her childhood influenced her spending patterns as she became an adult. 

5:12 She started using a credit card for her job that eventually caused her some financial struggle.  

8:00 As she helps her family members celebrate milestones, Emily’s finances get further strained. 

13:35 After she became overwhelmed with her debt, her boss recommended that she reach out to GreenPath. 

16:46 She recounts the relief she felt talking to GreenPath. 

22:35 Emily discusses how her spending approach with her family has changed as she has become more disciplined with her finances. 

25:47 She thinks back to the joyful feeling she had when she became debt- free. 

27:53 Her money that had been allocated towards her debts gets used for some unexpected travel and medical expenses. 

31:19 She shares her future dreams of homeownership. 

39:08 Our co-hosts reflect on the themes and lessons learned from Emily’s story. 

GreenPath Financial Service

GreenPath is a 60-year trusted national nonprofit, learn how GreenPath’s Debt Management Program can help you pay off your debt in 3-5 years, while helping you develop sound financial literacy.