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Redefining Success: From Job Loss to Entrepreneurship

WIOA Dislocated Worker Program Leads Participant to Stability & New Beginnings


After decades of experience in Healthcare and IT, Jim Castellano faced an unexpected challenge when he lost his job at Marshfield Clinic in December 2022. Around the age of 60, he found it difficult to secure new employment, but he wasn’t ready to slow down. That’s when he connected with WorkSmart, where Career Planner Lynn played a crucial role in helping him navigate the job market.


Enrolled in the WIOA Dislocated Worker program, Jim worked closely with Lynn, whose expertise in resume and cover letter development—especially tailoring them to meet AI application scanning standards—helped him stand out. From a whopping six-page resume, she helped him pare it down to create multiple targeted resumes for specific roles.


Together, they discussed in-demand occupations, assessed his strengths, barriers, skills, needs, and interests, and refined his job search strategy. Lynn also helped him optimize his LinkedIn profile, shared job fair opportunities, and sent job listings along with links to job descriptions to keep his search on track.

 
“[Lynn] had a great ability to listen and understand a situation,” Jim recalls. “She just helped me see the forest through the trees.”
 

At the time, Jim was focused on securing employment quickly, as he had recently relocated to reduce costs and needed a stable income. However, his long-term goal was to obtain a coaching certification and transition into a career that aligned with his passion for mentoring others.


WIOA Dislocated Worker program participant Jim Castellano post-layoff in La Crosse, WI.
WIOA Dislocated Worker program participant Jim Castellano post-layoff in La Crosse, WI.

Thanks to Lynn’s guidance, he not only secured a high-paying role in his field—earning $53/hr as a program manager at Aspirus Health managing MyChart for Epic applications—but also gained the financial stability and industry experience that ultimately positioned him to launch his own business as he wanted to.


Creating Compass Tree Consulting & Coaching, Jim made the leap to entrepreneurship and will be launching his business soon in 2025. The company focuses on guiding medical students, residents, and nurses as they transition into their roles, as well as partnering with organizations for healthcare development reform.


Even before officially launching his business, Jim already secured a contract with Vital Work Life, a Minneapolis-based consulting company, as a nurse peer coach. He also began expanding his network, meeting with a residency director at Gundersen Health System and seeking connections with local universities like UW-La Crosse, Viterbo, and Western Tech College to support students.


Jim’s journey is a testament to resilience, adaptability, and the power of the right support system. He encourages others to embrace career assistance with an open mind. “Be vulnerable, allow people like Lynn—who know the industry—to guide you. Be humble, listen, and engage with the process. The services offered by WorkSmart are valuable.”


Based in La Crosse, Jim is forging ahead in his consulting work and staying close to his three grown children, who have all built successful careers in healthcare and education. While WorkSmart is known for helping people find new jobs, Jim’s story proves that it does much more—it helps individuals discover their true passions and take bold steps toward fulfilling careers.



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