When Should You Stop Working? – Determining the Best Time to Retire


What’s your future? After active duty will you retire from the military to a “bridge career”, will you semi-retire to work part-time, or will you retire early and never earn a paycheck again?

These questions are tough retirement issues. Like all tough questions, the answer is “It depends”. It’s not an easy answer, but it’s the only one that will help you decide what’s best for you. While you’re pursuing it, give yourself the option to change your plan. You have time. The skills that employers truly care about (your leadership, your experience, and your ethics) won’t go stale. Talk with your family and think about your goals. Don’t lock yourself in!

Your top priority is your family’s financial independence. If you haven’t achieved that by the time you’ve left the service then you’ll need to keep working. Your next priority is the happiness of you and your family. They may want you around more often and your idea of happiness (and supporting them) may be quite different from theirs. A career change is a great time to discuss all the options and expectations.

Your feelings/emotions about your career changes will make a big difference in your performance and your health.  They’re also much more difficult to handle than the mechanics of a transition.  On active duty you’re surrounded by mentors and peers who can tell you precisely where you need to go and exactly how to get there, but it’s not that easy when your retirement time approaches.

The best career wisdom I’ve ever heard is: “Do it as long as you’re having fun”.

Your peak performance comes from being challenged, fulfilled, and happy.  That leads to faster promotions and even better jobs.

On the other hand we’ve all met the miserable people who tried to do tours that they weren’t suited for (despite their best intentions), or those equally miserable folks who stayed too long.  Take it one tour at a time and stop when you can’t find anything more that you’d enjoy doing.

Leaving the military may be hard and it’s harder to contemplate a few months without a paycheck.  However, the hardest task of all is the soul-destroying experience of enduring a tour that has no appeal or fulfillment.

Even outside the military, it’s tough to keep your financial & family priorities if you’re not having fun. You have to pay attention to your own feelings as you go through your military retirement transition. You’ll only succeed at your goals if they make you feel curious, happy, and maybe even excited about chasing them. If you’re grimly clenching your jaw and preparing to gut it out for another five years then you may not be making the right choice. You may even be risking your mental, emotional, and physical health.

Watch out for another unhappy situation: burnout. It’s extremely difficult to make good choices when you’re exhausted, frustrated, and miserable. If you feel that retiring is the only way to get out of a terrible job then you may need to reconsider where you’re going. Many people pursue a fantasy retirement because they can’t imagine putting up with work any longer. When they retire, though, they may find that they haven’t developed a lifestyle (or the savings!) to enjoy their new free time.

If you have the chance to catch up on sleep, clear your head, and think about all the issues then you may decide that what you really need is a different assignment or a career change. Don’t keep working because you can’t imagine what else you could do with yourself, but don’t retire just because you’re positive that work can’t get any worse. You have to move toward a goal, not just run away from bad situations.

I’ve heard from many unhappy people in the military, so let me emphasize the illusion of a fantasy retirement. When you’re chronically overworked, overstressed, and suffering low morale then making a retirement decision is an overwhelming impossibility. You can’t make good decisions during burnout.

Instead of risking your finances and your lifestyle, find a way to get some time off. It’s hard to get two straight weeks of leave to contemplate your future, especially if you’re transferring between duty stations, but you have to find the time. Don’t use that precious leave to clean the house, finish the yardwork, or take the big family vacation.

You’re going to focus your efforts (and your family’s discussion) on getting ready for retirement with maybe a bridge career. Catch up on your sleep, spend a couple days winding down, and let the fog clear from your thinking. By the end of the first week, you should be ready to start talking about the issues and considering your decision.

About Doug Nordman

Author of "The Military Guide to Financial Independence and Retirement" and co-author of "Raising Your Money-Savvy Family For Next Generation Financial Independence."
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