Should You Re-Enlist?

Joe Wallace

Some join the military and pursue a 20-year career. Others don’t stay in until they are retirement eligible; they leave the service and move into a civilian career. Making that decision can be tough; it’s much more than just a job change.

It’s a shift in your entire way of life, your identity, and your future. When times get tough, many consider changing their direction in life. For some, it’s about transitioning out of the military to find new opportunities elsewhere.

Should You Re-Enlist?

Leaving the military means stepping away from a structured, mission-driven world. While civilian life offers more freedom and new kinds of opportunities, it also brings its own uncertainties and a completely different set of rules.

Making the right decision to stay or go requires a deliberate and honest assessment of your personal ambitions, your family’s needs, and your financial situation. In times of economic and political uncertainty, these choices become even tougher.

Do you have the ability to walk into a new job “on the outside” or do you need education and training? There are many other factors to consider when planning your future.

It pays to take a lesson from military pilots, who use pre-mission checklists to ensure things go as planned. Below is a different sort of checklist, one you can use to begin planning a move out of the military or a decision to stay and “re-up.”

Should you stay or should you go? Much depends on personal circumstances, needs, and goals. The checklist below covers a range of concerns, but it can’t anticipate everything. The best use of this checklist is to use it as a jumping-off point, adding your own additional needs or concerns to what’s found here. Remember, transitioning from active duty to the Guard/Reserve or back to civilian life may be challenging, but it’s a journey worth taking.

Professional & Career Considerations

• Current Role & Military Specialty
  • Am I still challenged in my current job?
  • Have I discussed the health and future of my military occupation with a career counselor?

• Advancement & Promotion
  • Am I on a path to promotion? Have I hit a plateau?
  • What are the realistic promotion timelines for my rank and MOS?
  • Have I spoken with senior enlisted leaders about my potential?

• Future Opportunities
  • What are my potential next military assignments if I reenlist?
  • Have I considered retraining for a new military career field to acquire better skills or opportunities?
  • Do I understand the trade-offs of reclassification, such as the need for new training and the potential loss of seniority?
• Operational Tempo:
  • Am I mentally and physically prepared for future deployments and training cycles?
  • How have past deployments impacted my well-being?
  • Am I being honest with myself about my capacity to continue at this pace?

Things to consider: future opportunities for professional military education, deployments, temporary duty for training, high-year-of-tenure considerations, and current personal investment in the career.

Family & Personal Life

• Family Dialogue:
  • Have I had an honest conversation with my spouse and children about reenlisting?
  • Do I understand their goals, dreams, and concerns?
  • How would another enlistment term impact my spouse’s career goals?
  • How would it impact my children’s education and social stability?
  • Is my family’s support system strong enough for another term?
• Personal Goals:
  • What are my personal goals outside of the military (e.g., education, starting a business, learning a skill)?
  • Is it more practical to pursue these goals while in the service or as a civilian?
  • Have I taken full advantage of benefits like Tuition Assistance?
• Health & Well-being:
  • Have I assessed my cumulative mental and physical health?
  • Am I addressing any existing stress or burnout before making a decision?
  • Do I have a healthy work-life balance?

Things to consider: Where family members are in school, how a change in career or military status may affect that, and how your personal goals fit in with your long-term family goals.

Financial Analysis

• Military Compensation:
  • Do I fully understand the value of my military pay, allowances, and benefits?
  • If a reenlistment bonus is offered, do I have a clear plan for how to use it to pay down debt, invest, and save?
• Civilian Comparison:
  • Have I researched the average civilian salary for a job that matches my skills and experience?
  • Have I factored in the costs I would have to cover as a civilian, such as health insurance, retirement contributions, and state taxes?
• Long-Term Security:
  • How close am I to the 20-year retirement mark?
  • Do I fully appreciate the financial security of a military pension and other veteran benefits (like the GI Bill and VA Home Loan)?

Considerations: How much debt will be carried over in a transition from military to civilian, whether or not you will have a mortgage obligation, and whether student loan repayment might be affected by a career change from military to civilian.

The Transition Plan

• Creating a Viable Alternative:
  • Have I created a solid, actionable plan for what I would do if I chose to separate from the service?
  • Have I updated my resume to translate my military experience into civilian terms?
  • Have I started networking with people in industries that interest me?
  • Have I explored military transition assistance programs (like TAP)?

There is no easy answer to the question, “Should I transition?” But there is a right one for you. Take the time to honestly assess these areas of your life. Doing so will help you approach this decision with the clarity you and your family deserve, ready for whatever chapter comes next.