Finding their paths by hitting the road: Three students make their way with wraparound support from a career coach

Two mission-driven, growth-centered organizations combine forces to drive student success

For young people nearing the end of their high school education, the idea of college can produce powerful emotions ranging from uncertainty, anxiety and panic to hopefulness and excitement — and sometimes all of them all at once. It’s not unusual for many “What if” questions to loom large: What if I’m not “college material”? What if I can’t afford it? What if I don’t get accepted? What if I don’t fit in? What if I’m not ready? What if I can’t find a career path? What if now isn’t the right time for college? What if I hate it? What if I don’t know how to take the next step in my journey? This college-related confusion is as understandable as it is common in high school students from coast to coast.

In response, InsideTrack and Roadtrip Nation posed our own “What if” question: What if we could help clear things up? To that end — and with a shared mission to provide learners better access to educational and career opportunities — we embarked on an official partnership in December 2021. Through the partnership, students gain invaluable advice and actionable information. Roadtrip Nation sends students on road trips that help them discover and explore career paths that relate to their interests. Then, once they’ve returned, InsideTrack supports the roadtrippers with six months of holistic coaching, helping them integrate lessons learned on their road trip into their life. By working together to enlighten and empower students, this partnership turns the lofty, discomforting idea of choosing a life path into an understandable, achievable goal and connects education to real-world career pathways and possibilities.

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Aligned toward the goal of expanding educational and career opportunity

Both part of Strada Collaborative, InsideTrack and Roadtrip Nation share a dedication to making positive change and a commitment to providing educational and career opportunities for learners across the country. Roadtrip Nation does this by producing content, tools and experiences designed to help students and career seekers forge their own path to meaningful work. Part media company, part career education platform, they help connect learner interests to career possibilities by introducing them to inspiring individuals, often from similar backgrounds, who are engaged in work they love. In tandem, InsideTrack has been working for nearly 25 years to fuel social mobility and close equity gaps by empowering and advancing all learners. We harness the power of coaching to help them overcome barriers to success, giving everyone the opportunity to reach their goals and find their purpose. In our partnership with Roadtrip Nation, our like-minded sister company, our work begins soon after each Roadtrip Nation’s road trip ends.

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Turning lessons from the road into skills for life

Providing a continuity of care after the roadtrippers transformational journey has helped them re-enter their lives feeling supported and has given them a structured, guided way to reflect on, grow from and springboard off of the Roadtrip experience. 

Since December 2021, 105 learners from 32 separate trips have received one-on-one support from an InsideTrack coach. 85% of surveyed participants stayed in contact with their coach, with an average of 6.4 meetings per participant. These impressive numbers speak to the roadtrippers’ level of engagement and interest in this kind of support, as well as to the overall impact of coaching. 

The coaching meetings with the roadtrippers focus on a wide variety of topics. Some of most the common coaching conversations cover:

• Personal growth and mindset
• Goal setting
• Career exploration and cultivation
• Health and wellness
• Overcoming obstacles
• Crucial conversations
• Financial planning

When surveyed about the aspect of coaching the roadtrippers considered most valuable, one participant said, “I wouldn’t be able to choose a moment, but rather the gradual realization of how well the meetings helped me step back, look at my life, analyze what went well and what didn't, and make a plan to fix it.” Another roadtripper shared that the coaching sessions made it possible to “…slow down and reflect, especially on what I had accomplished. I'm not good at celebrating my accomplishments, but coaching gave me the space to do that. It also gave me the opportunity to process what was going on in life as I am a verbal processor.”

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The partnership in motion

Perhaps the best way to get a sense of how InsideTrack’s partnership with Roadtrip Nation works is by taking a look at the most recent Roadtrip. The 2025 Rethinking Higher Ed Roadtrip invited three young people into Roadtrip Nation’s famous bright green RV to traverse the country together. By stopping along the way for illuminating conversations with subject matter experts and near-peers whose lives and paths have been deeply impacted by their experiences in higher education, these roadtrippers learned about what options there are after high school and how to best navigate these choices.

The roadtrippers’ return marks the start of InsideTrack’s involvement. InsideTrack coaches began their outreach about three weeks after their road trip ended, allowing participants to reintegrate back into their lives first. Over the course of the next six months, each roadtripper and their coach worked together one-on-one to keep the trip’s momentum going and to develop the concrete skills, strategies and habits needed to advance toward their educational and career goals.

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Meet the roadtrippers

The Rethinking Higher Ed Roadtrip put three intrepid learners on an RV voyage from Southern California to the Midwest — and on a journey of exploration into postsecondary paths and options. While the literal road they traveled during the trip may have been the same, their backgrounds, experiences, interests and coaching needs show the trio’s true diversity. InsideTrack’s Jaima Mavity was the student success specialist and coach who worked one-on-one with each of the learners from this trip, furthering and enhancing the lessons and discoveries from the road. Here more about each of the roadtrippers’ unique experiences. 

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Aislynn Fait

Hailing from Pennsauken, NJ, Aislynn was homeschooled until age 17. It’s highly understandable why adapting to college proved challenging. But she stuck with it, ultimately earning her associate’s degree from community college. Though the financial and logistical aspects felt intimidating, Aislynn really wanted to transfer to a four-year school to continue her education and pursue her interests in fashion and sustainability. 

Coach Jaima was instrumental in helping Aislynn get into the right headspace for that transition. “In our sessions, Aislynn and I worked to transform her perception of a gap year from an unstructured break into a strategic period for her sustainable fashion career aspirations,” says Jaima. They also focused on overcoming Aislynn’s procrastination, and together they developed a concrete plan of action for moving forward, breaking overwhelming goals into manageable steps. “Ultimately, having external accountability and a structured framework greatly boosted Aislynn’s motivation and momentum,” Coach Jaima said. And the best news? Aislynn applied to the New York Fashion Institute of Technology — and was accepted!

Hear more from Aislynn about her coaching experience.

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Eric Pōmaika’i Gee

Eric is a high school graduate from Waikōloa, Hawai’i, with passions that include social justice and education reform. An avid runner and beachgoer, he served as a youth commissioner for both the county and state of Hawai’i. Coaching sessions with Jaima helped Eric transform his uncertainty and overwhelm about his career path into actionable steps. According to Coach Jaima, “The ‘Dream Job Exercise’ helped Eric identify his ideal career, and from there we pinpointed his strengths, like public speaking, that align with his preferred career roles.”

Eric draws inspiration from leaders who are making a wide social impact, and he wants to broaden his understanding of equity, justice and public policy to ultimately better serve his community. Based on his interests, he is now pursuing a bachelor’s degree from the University of Hawai’i at Manoa — with a double major in international business and finance. Thanks to the work done with Coach Jaima in their sessions, Eric’s next steps include researching necessary skills as he works to figure out the exact career path for him, prioritizing skill development as a way to bridge any gaps. His coach proudly shared, “Eric’s proactive, strategic mindset shows a crucial shift from passive dreaming to active planning.” 

Hear more from Eric about his coaching experience.

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Ruby Savala

A high school graduate, Ruby has a law enforcement certification from San Jacinto Community College and a Level 2 Traffic Control and Security Certification. Driven by a strong desire to protect, she founded a club that provides volunteer security for community events. She has a passion for criminal justice, shares her mom’s belief in the power of education, and is devoted to the ten pets she rescued. Her interest in becoming a Forensic Investigator makes perfect sense. 

While her goal was clear, she needed some help getting there — help that Coach Jaima was ready to supply. “Ruby planned to apply to her dream school, Sam Houston State University (SHSU). As her coach, I supported her through application anxieties and served as a consistent and supportive presence, giving her space to process while helping her craft a detailed, manageable plan for her future.” Having secured her spot and 45 transferable credits, Ruby is now attending SHSU and is working to get her bachelor’s of science in criminal justice with a minor in forensic science — and she’s more confident and ready than ever. Her coach was quick to note that, despite various stressors, “Ruby’s commitment to her educational and career goals was inspiring, as was her resilience in the face of significant personal challenges.” 

Hear more from Ruby about her coaching experience.

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A meaningful partnership delivering important results

Through this rewarding partnership, it has become clear that holistic support focused not just on the necessary tasks, like resume building and job searching, but also on building confidence, personal well-being, self-reflection and mindset shifts is essential for helping the roadtrippers — and all learners — take away long-term lessons and move toward their goals. As Coach Jaima explains, “The goal was to empower through structure, offering to break down overwhelming tasks into smaller, easier, more manageable steps they could take action on. Intentionally, I often made time for cultivating self-reflection, creating a safe space for learners to vocalize their thoughts and gain insights they may have otherwise missed during their road trip.” 

“The goal was to empower through structure, offering to break down overwhelming tasks into smaller, easier, more manageable steps they could take action on. Intentionally, I often made time for cultivating self-reflection, creating a safe space for learners to vocalize their thoughts and gain insights they may have otherwise missed during their road trip.”  - Jaima Mavity, Lead Student Success Specialist & Coach, InsideTrack

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