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.

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The Biggest Benefits of a Military Retirement


All retirees have to accumulate the resources to last for the rest of their lives, but early retirees (before age 65) have two daunting challenges: paying for healthcare and contending with decades of inflation.

Health insurance is largely a workplace benefit, and many civilian workers feel “locked in” to their jobs by it. Health insurance can be hundreds of dollars per month without an employer’s subsidy, and it’s difficult to obtain individual coverage for pre-existing conditions. The American healthcare system is the main reason that traditional retirees stay in the workforce until age 65, when Medicare starts to cover much of their health expenses. Even after age 65 retirees still have to contend with rising insurance premiums, higher prescription medication costs, and long-term care concerns.

Inflation is far more insidious. While a health crisis can wipe out a retiree’s finances, inflation is at least as deadly because it’s hard to notice the corrosive long-term effects. At just four percent a year, a decade of inflation can raise retiree expenses by nearly 50%. Retirees in their 60s may only have to contend with two or three decades of inflation, but retirees in their 40s will have to survive four or five decades of inflation that could easily triple their expenses.

The Biggest Benefits of a Military Retirement

The military’s pension system beats both of those obstacles.

Unbelievable as it may seem, Tricare is among the nation’s premiere affordable healthcare systems. It covers far more for active-duty veterans (and their families) than civilian health insurance– while charging far less. Unfortunately, many veterans don’t learn this fact until they leave the service, while others with pre-existing conditions may feel locked into military or civil service in order to be able to afford their healthcare costs. In 2010 an active-duty retiree pays less than $40/month for comprehensive Tricare family coverage that, for civilian retirees, would cost hundreds or even thousands of dollars.

As good a financial deal as Tricare may be, the military pension is even better! Military veterans can earn a defined-benefit pension in an era when employers are moving toward defined-contribution 401(k)s. Despite the risks that we bear to qualify for that government pension, it’s paid by one of the world’s best-funded institutions with the power to raise its own money.

Not only is the federal government likely to pay military pensions long after corporate pensions hit the skids, that pension includes a cost of living adjustment (COLA) for inflation. This is extremely rare in the business world. Federal pensions (as well as Social Security) rise each year by the inflation rate measured in the Consumer Price Index (CPI). That index may have its own flaws and detractors, but there is no better measure of the nation’s inflation. You may experience a personal inflation rate that’s smaller (or perhaps bigger) than the CPI, but veteran’s pensions will keep up with inflation far better than any other system.

How has the pension kept up over the years? The answer is “pretty well for everyone, better for some”.

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“But… but… but what will I DO all day?!?”


“But… but… but what will I DO all day?!?”

The two biggest challenges facing financially independent people may be inflation and affordable healthcare. However, the most frequently-asked question is what you’re going to do with your new life.

Ironically, the question answers itself once you retire. It may be the top question before early retirement, but after you retire you’ll wonder what the heck you were worrying about!

But let’s try to answer it now, and first we’ll try a metaphor: When you retire, every day is Saturday and every night is Friday night.

Next, imagine having control of your time again. What would your morning be like if you didn’t have to rush through your wakeup routine, wolf down breakfast, and fly out the door to work? You’d probably sleep an hour later, enjoy a leisurely breakfast, and have another cup of coffee with the morning newspaper. You’d work out, take a shower, and then have a snack while you’re reading a book or answering e-mail. Feeling refreshed and relaxed, you’d wonder what to do with the rest of your day.

As you look around the house, you’d realize that you still have chores– dirty dishes, dusting, vacuuming, yardwork, and maybe a few home repairs or improvements. You need to shop for groceries and plan some meals. Maybe you need to fix up your car. When you were working you might hire a housecleaner, a yard service, a handyman, and a mechanic. Now it’s your choice to continue to pay to have it done for you or to do it yourself.

Otherwise if you’re a surfer or a golfer then the rest of the daily schedule is filled! Maybe you have another sport or hobby that you want to catch up on.

Traditional retirement advice is “Nobody can play golf all day every day!” I’m not sure that’s correct, but let’s say that the weather doesn’t cooperate. What else will you do when you can’t do what you want to do, or when you get tired of the choices that are available?

You have to be responsible for your own entertainment. If you’re not able to jump-start your own creativity then try a tool like Ernie Zelinski’s “Get-A-Life Tree”. (For a sample, see page 82 of Mr. Zelinski’s book: How to Retire Happy, Wild, & Free) Write down a list of the things you enjoy doing and then think of the things you used to enjoy doing– when you had the time. Does that make you think of other things you’ve always wanted to try?

The “What will I DO all day?” question is difficult to answer because it’s hard to imagine that type of life. Once you’re living it, you’ll be able to slow down and enjoy your routine while taking the time to plan your life. You don’t have to figure out every detail of your day before you retire– you only need the confidence that you’ll be able to figure it out just like all the other financially independent retirees.

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