What does it take to build a career when every step forward comes with a tradeoff—when choosing training means losing wages, when choosing stability means rearranging childcare, and when choosing your future means risking the little security you have today?
For many New Yorkers, the road to stability isn’t a straight line—it’s a climb, one careful choice at a time.
In this companion to our conversation with Brooklyn Workforce Innovations’ Executive Director Aaron Shiffman, we hear from Tiphany, a lifelong NYCHA resident who turned a moment of uncertainty into a path toward purpose. After coming across a flyer in her building lobby for the NYCHA Resident Training Academy—a program facilitated by BWI—Tiphany made a choice that would transform her life.
As a single mother searching for stability, Tiphany faced the hard tradeoffs that define the cost of choice: balancing work and childcare, risking short-term income for long-term opportunity, and fighting through doubt to build something better for her family. Nearly a decade later, she’s risen from Caretaker to Property Maintenance Superintendent, overseeing the very kind of buildings she once called home.
Through Tiphany’s story, we see what happens when access meets determination—and how investing in career mobility can help New Yorkers move from surviving to leading.
Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.
You can find transcripts and more episodes of \"This Robin Hood Moment\" at robinhood.org/podcasts.
Thoughts? Guest suggestions? Email us at info@robinhood.org.
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