When's the Right Time to Retire?

It's a question most people grapple with eventually: When should I retire? The wondering and calculations and drawing up lists of pros and cons often start in the mid-50s, but sometimes not until the early 60s; by then, though, it's on pretty much everybody's mind.

There's a powerful allure in finally escaping the work obligation. Retirement also means the freedom to spend more time with the grandkids and other loved ones, travel, relax poolside, write a book, or whatever suits your fancy.

Creating a retirement plan is a highly personal matter. Obviously, there's no one-size-fits-all right answer as to when it's the best time to retire. Your finances, eagerness to keep or stop working, plans and goal, hopes and dreams, your significant other's situation and desires, and countless other factors come into play.

And while the prospect of retirement seems so exciting in theory, it's usually a little scary when it comes down to it. Concerns over losing a primary income, giving up something that keeps you occupied much of the week, separating from coworkers that have been part of your life for years, and other thoughts can be stressful.

In many cases, these worries cause people to push retirement back. But while there are good reasons to delay retirement, fear isn't one.

In fact, a 2015 New York Life survey of retired 62 to 70 year olds found that 46% of retirees wish they'd retired sooner (and 51% of those who retired after 60). The respondents consistently said they should have retired about 4 years earlier than they did.

Here are some important questions to help decide when it's time to pack up the office desk, tell your kid to clean out the guest room, and maybe find a nice new home in an amazing resort-style active-adult community:

Am I Financially Ready to Retire?

This is the big one. Your best bet here is to consult a professional financial advisor. You need to be able to live off your savings, assets, and any post-retirement income coming in. Plus, you'll want disposable income to do all the things you want to do in retirement. Have you maxed out the benefits you can accrue through your job? Will you have to pay penalties for cashing in a retirement account early? How long until your pension and social security kick in? Are you prepared for common unexpected expenses? There are lots of numbers to crunch.

Can You Fill Your Time?

Not everyone's prepared for the major lifestyle shift of retiring after a lifetime of working. Suddenly, there are enormous voids to fill. It's not just time; work is a primary driver for getting out of the house and provides a good deal of social interaction. Even with general plans to travel and visit family, you need specific plans to occupy your time, go places, and interact with people on a day-to-day basis.

What's Up with Your Spouse or Partner?

If you're retiring as part of a team, consult the other half. Is your significant other ready to retire too? Is he or she ready for you to retire? Discuss the other person's plans, desires, and aspirations, because they have to sync up nicely with yours. Some compromises will probably be in order, but you must find ways for retirement to make both of you feel happy and fulfilled.

How Do You Feel About Your Job?

Do you love going to work every day? Dread it? Does it make you feel fulfilled, bored, miserable? Are you productive and doing things you believe in, or do you sit there watching the clock run down day in and day out? If you still get something positive out of your job, maybe it's best to stick with it; if it's just a source of stress that's holding you back, perhaps it's time to move on to the next stage of life.

How's Your Health? Your Partner's Health?

Though it's not one of the more pleasant topics, evaluate your health and your significant other's. Also, consider your parents' medical history. Are they still going strong in their 80s? Did they pass away relatively young from conditions with a genetic component? While nothing is ever certain, having a general time frame in mind can be a big help deciding when to retire.

Consider a 55+ Community

Here at Central Florida 55+ Realtors, we're strong advocates for taking up residence—or a vacation home—in one of the area's active-adult communities. Surely that comes as no surprise.

But we decided to specialize in this niche because of our passion for these communities, which we live in ourselves. They are enormously beneficial for keeping you physically, mentally, emotionally, and socially active in the retirement years. They make it so easy to relax and to engage as the mood strikes. A home in a 55-plus community truly helps you make the most of the post-work years.