Navigating Career Transitions and the Value of Going Back to School
- Jimmy Stewart

- Nov 18
- 4 min read
Deciding to go back to school after decades in a career can feel like a puzzle with no clear solution. For someone with 30 years of experience as a senior technologist in a global law firm, respected by peers and known for delivering effective solutions, the choice to return to the classroom might seem unnecessary. Why pursue a formal degree when practical knowledge and proven skills have already paved the way? This question led to deep reflection and honest self-assessment, revealing insights about growth, validation, and future opportunities.
Reflecting on the Past to Understand the Present
My career began in the United States Army right after high school. Ten years of service taught me more than just discipline and leadership; it shaped my ability to manage people in high-pressure, ever-changing environments. These experiences were invaluable, but they also highlighted the importance of technical expertise.
In the Army, I worked with the Judge Advocate General’s (JAG) Corps as a Legal Specialist. Early on, I was assigned to the Family Law group, handling tasks like drafting wills, powers of attorney, and electronic tax filings. I even became a Notary. What stood out was how much of this work was already being automated through software. At 19, I found it fascinating to use technology to simplify complex legal documents. This sparked my interest in legal technology and set me on a path that would define my career.
An important lesson came from a senior colleague early in my military career. I initially judged his rank as a sign of limited success, but I had asked the wrong question. Instead of focusing on his rank, I should have asked how long he had been in the Army. His six years of service, compared to my shorter time, explained the difference. This taught me to ask the right questions, a skill that proved essential throughout my career and in deciding to return to school.
Why Going Back to School Matters Even with Experience
Experience builds confidence and skills, but formal education offers something different: validation and new perspectives. Here are some reasons why going back to school made sense for me:
Credibility: A degree provides official recognition of knowledge, which can open doors that experience alone might not.
Updated Knowledge: Technology and legal fields evolve rapidly. School offers the latest theories, tools, and practices.
Networking: Classmates and professors can become valuable contacts for future opportunities.
Personal Growth: The challenge of learning in a structured environment pushes you to grow beyond your comfort zone.
For someone with decades of experience, these benefits might not seem urgent. But the world changes, and staying relevant requires continuous learning. Going back to school is not about proving what you know; it’s about expanding what you can do.

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Facing Challenges and Overcoming Doubts
Returning to school after years in the workforce brings challenges. Balancing work, family, and study demands careful planning. Doubts about fitting in with younger students or keeping up with academic work can be intimidating.
To manage these challenges, I focused on:
Setting clear goals: Knowing why I was going back helped me stay motivated.
Time management: Prioritizing tasks and creating a study schedule made the workload manageable.
Seeking support: Talking with family, mentors, and classmates provided encouragement and advice.
These strategies helped me turn obstacles into opportunities for growth.
Practical Tips for Professionals Considering a Return to School
If you are thinking about going back to school after years in your career, here are some practical tips:
Assess your goals: Understand what you want to achieve and how education fits into that.
Research programs: Look for courses that align with your experience and future plans.
Consider flexible options: Online or part-time programs can accommodate work and family commitments.
Leverage your experience: Use your background to enrich class discussions and projects.
Stay open-minded: Be ready to learn new methods and ideas that challenge your assumptions.
These steps can make the transition smoother and more rewarding.
Embracing Lifelong Learning as a Career Strategy
The decision to return to school is part of a larger mindset: lifelong learning. In technology and law, staying current is essential. Formal education complements on-the-job experience by providing frameworks and credentials that support career advancement.
By embracing learning at any stage, professionals can:
Adapt to industry changes
Explore new career paths
Increase job security
Enhance personal satisfaction
This approach transforms education from a one-time event into an ongoing journey.
Final Thoughts on Career Transitions and Education
Going back to school after decades of experience is not a sign of weakness or doubt. It is a strategic move to strengthen your foundation and prepare for future challenges. The blend of practical experience and formal education creates a powerful combination that can open new doors and deepen your expertise.
If you are facing a similar decision, ask yourself the right questions. Reflect on your goals, challenges, and the value education can bring. Remember that learning is a lifelong process, and investing in yourself is always worthwhile.



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