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When the Past Won’t Let Go, Even After You’ve Done Everything Right

“People always say the sky’s the limit, but that has never been true for me.”

At 48, Cindy’s life looks like the kind of story we love to celebrate. She’s nine years substance-free. She earned a master’s degree. She built a career helping others through some of the hardest moments of their lives. She is a mother, a leader, and someone others trust.

But mistakes she made at 21 led to a criminal record that still limits where she can live, where she can work, and whether she can vote or pursue professional licenses.

“I’ve done everything right,” she said. “I’ve paid my debt to society. And still, I’m asked to jump through hoops of fire.”

The long shadow of a record
For years, Cindy tried to clear her record on her own, but the process was anything but simple.

Each county had different rules.
Legal fees added up quickly.
Paperwork was confusing and endless.
And every step required reopening parts of her past she had worked hard to move beyond.

Like millions of others, Cindy learned that while record-clearing may be legally possible, it often feels unattainable. The cost, complexity, and emotional toll cause many people to give up before they ever get started.

Not because they don’t deserve a second chance, but because navigating the system alone is overwhelming.

Cindy’s experience is not unusual. What is unusual is what happened next. Her employer stepped in.

A different kind of support
When Cindy joined Wayspring three years ago, she didn’t expect her employer to help her with something so personal.

But in September 2025, Wayspring launched Second Chance Scholarships, an employer-funded program designed to help employees navigate the legal and financial barriers tied to past criminal records, including expungements and pardons.

The idea was simple: growth should matter more than past mistakes.

The program provides financial assistance and guidance through a complicated legal process that many people are forced to face alone. Applications are reviewed by Wayspring’s Criminal Justice Committee and evaluated based on accountability, personal growth, and a demonstrated commitment to supporting others.

In its first year, three employees applied. All three were awarded scholarships. Cindy was one of them.

“The feeling was freedom”
“I just started crying,” Cindy said after learning she received the scholarship. “The feeling was…freedom. Knowing that this final thing from my past wouldn’t weigh me down anymore. That the sky is the limit.”

“Not everyone starts life with the same opportunities,” said Tanya Deane, Chief Human Resources Officer at Wayspring. “Second chances should be possible for anyone willing to make a change.”

Why this matters
Second changes depend on systems willing to recognize growth, remove barriers, and make room for people to move forward.

Employers can play a role in that change. At Wayspring, second chances are not just something we believe in. They are something we invest in and support, both inside our organization and through the work we do in communities every day. Because people are more than their past.

For Cindy, and for others like her, support at the right moment can mean the difference between being stuck and finally being free. And sometimes, the most meaningful opportunities come not from starting over, but from being allowed to move forward.

Read the full announcement about Wayspring’s Second Chance Scholarship program: https://www.businesswire.com/news/home/20260113133826/en/Wayspring-Launches-Second-Chance-Scholarship-Program-to-Help-Employees-Move-Forward-When-the-Past-Wont-Let-Go

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