Transitions: Providing Clarity Amongst the Chaos

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Dr. Bob Habib, USO HRCV Transitions Manager, briefs re-deploying service members at Naval Station Norfolk on the transitions process.

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Dr. Bob Habib, USO HRCV Transitions Manager, answers questions from a service member at a re-deployment Transitions brief.

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Dr. Bob Habib, USO HRCV Transitions Manager, answers questions from a service member during a virtual appointment.

Experiencing “information overload,” checklists galore, unit out-processing and most likely a move to a new permanent address are all decisions that must be made for life after the military. Then, there is the job search.

Whether a service member is transitioning from military life after three years or 30, most everyone of them ends up at the same place…what’s next? Where do I go from here? How do I find a job that is fulfilling and purposeful? And what about my spouse? Is there any help for my spouse too?

The USO of Hampton Roads and Central Virginia (HRCV) Transitions Program is designed to help transitioning service members and families find answers to these questions. “We help provide clarity amongst the chaos,” said Dr Robert (Dr. Bob) Habib, Transitions Manager, HRCV. “We act as the conduit to link service members and their families to well-vetted organizations to help them reach their goals and objectives. The transition program aims to boost an individual’s professional, academic, and personal acumen throughout their career, not just as they approach the end of their military career.”

The Transitions team creates customized and tailored plans for each client then they are provided specific resources to help them achieve their goals. “With the USO Mobile app, we can track their transition progress and check in with them periodically to see how they are doing,” Habib said. “So, we not only provide the tangible resources, but then we walk with them through the process as they go to ultimately achieving those objectives with tangible outcomes.” How long the Transitions team tracks each individual is completed on a case-by-case basis, but typically up to three months past separation.

The USO Transitions team is embedded with transition programs specifically on Naval Station Norfolk by briefing the pre-separation and retirement programs as well as working closely with their Naval Fleet and Family Services counterparts. They brief local commands as they deploy and redeploy troops to include Guard and Reserve units of all branches. According to Habib, they have a representative on Langley Air Force Base to brief at the newcomer’s orientations to increase the amount time troops will have to be exposed to the benefits of the transitions program.

Even though they provide service to all installations in the Hampton Roads and Central Virginia region, they are gearing up to expand their physical presence in 2022. Covid and the ongoing pandemic had a huge impact on transition programs across the country, said Habib, and Hampton Roads was no exception. Going virtual for a lot of the briefings and working with clients was a natural “transition” to build up to.

What about spouses? How do they fit into the program? It just so happens that even though Habib is retired Army, he was also a military spouse. His wife was in the U.S. Marine Corps for 20 years. “We love our military spouses and can work with them throughout their spouse’s military career,” he said. “We often see the spouses come with the military member during the separation briefings and meet them there to discuss family goals post military life. But, we can and do work with military spouses at any time throughout the spouse’s military career. We do have some great and unique resources that we can provide to military spouses.”

“We understand that while the military family is a strong unit,” Habib said, “military spouses are still independent people and will likely have different personal, professional and academic goals.” Spouses are encouraged to register as a unique client and the Transitions team will work independently with them.

No matter where a person is in the process, whether a service member has a couple of years before separation or even just a few weeks, the Transitions team can help set them up for success. They do this through five major focus areas of assistance, according to Habib. “The focus areas are employment, education, financial readiness, VA benefits, and mentorship, but of these, the education and employment pieces are the most utilized,” he said. If they are a couple of years out, the team can help them start networking and even start resume building by translating military jargon and accomplishments into civilian speak, said Habib.

The Transitions team will start the conversation on education and what that might look like for next few months. Does the service member have tuition assistance benefits they can use before separation? Or, do they need further certifications or credentials for the field they want to go into for example teaching?

There are also education partners can in some cases fit the bill moving forward to connect to those resources such as internships, Habib said. For the employment piece, the closer the client gets to actual separation, the narrower the focus becomes with job fairs, interview preparation, and solid resumes.

For the financial readiness and VA benefits focus areas, the goal is to the service member directly connected to trusted and well-vetted resources that will provide actionable, tangible outcomes for the client, said Habib. While the Transitions team can answer some questions on benefits and the claims process with the VA for instance, they will provide referrals of partners that can offer that expertise such as the Veteran of Foreign Wars representative.

“My goal is with service members and their families is to engage often and early in the transition journey whether that’s one day long or 10 years long, we will create action plans for them,” Habib said. Ideally, from day one of military service, Habib said he would love to be on every service members radar to know that they are available when the time comes for separation. “Individual growth not only helps the organization they are currently serving but will also help the individual as they seek new opportunities after military service.”

Transition specialists here typically have a client load of 100 people at any given time. In 2021, the USO HRCV Transitions team created more than 900 unique action plans tailored specifically for their clients. One of those clients was Keith Cassant (now U.S. Army retired).

Cassant began his transition nine months prior to retirement in 2019. According to Cassant, he had three passions that he was following in security, teaching and leadership, and all totally unrelated. While working with a Transitions specialist, he narrowed his focus to leadership and landed an apprenticeship with Wells Fargo Bank in management.

“If you are unsure about your path after the military, I highly recommend this program,” said Cassant. “The most important nugget I got from this process was to find your passion and focus in on one area,” he said. Cassant is now working for the U.S. Coast Guard in the Hampton Roads area as a Government Service (GS) civilian.

Another such client is former U.S. Navy Aegis Fire Controlman Raj Hoare who was a Sailor for six years and now lives and works in Florida. Hoare found about the transitions program from a friend who was also in the Navy having gone through the Transition Assistance Program (TAPs). Hoare just recently separated from the Navy in June.

Hoare knew in 2020 he was going to leave the Navy and became a client with Transitions specialist Tracey Bigelow. “Ms. Bigelow understood what I wanted when I got out and made a plan to help me get there,” said Hoare. He attended the Florida Institute of Technology and graduated with a business administration degree.

According to Hoare, he secured a Salesforce fellowship program through the networking and mentorship programs with the Transitions process. “Tracey was always very encouraging,” Hoare said. “The big difference between TAP and the Transitions team is that the TAP class does not help with the fine details like the Transitions program does.”

Both Cassant and Hoare volunteer their time now working as mentors to veterans helping them through transitions as well. “Mentorship is providing someone to talk to and so helpful during the transition process,” said Hoare. “Sometimes getting a job comes down to who you know not necessarily what you know, so mentorship is a key component once out of the military,” Cassant said.

Mentorship through the USO Transitions focus area is an opportunity to confirm that, yes, the service member is going in the right direction, and yes, they want to continue moving in their current direction. However, for some, they may develop a mentoring relationship with someone in their intended profession and decide it just isn’t for them.

“Clients are linked to organizations with industry partners such as American Corporate Partners. The service member gets to pick their own mentor,” said Habib. “Gaining insight to what an industry or particular job is really like in the workplace is either affirming and gives them momentum or it gives them the opportunity to rethink their current trajectory and steer into another career field.”

If there is one lasting mantra that Habib could leave any service member and their families with it is this; “Get on the right bus rather than trying to find the right seat!” He said there is a lot of pressure for service members to find the perfect job right after separation. But, Habib said, it’s more important to find the right industry first and then navigate to the right job or the right company for you.

To find out more about the USO HRCV’s Transitions program or to sign up with a Transitions Specialist, please visit: or call 757-395-4270. You can also reach “Dr. Bob” Habib at

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