Choosing a retirement date is an exciting time. Not only does it mean you no longer have to bust your hump at a nine-to-five for years on end, but it also signifies your transition into the next phase of your life–potentially the best phase of your life.

Historically, 65 has been the age used as a benchmark for retirement. But with longer life spans and longer retirements, you may decide you want to work as long as possible. For those with more physically demanding jobs or more financial flexibility, you may be on the other end of the spectrum and looking to retire as soon as possible. That’s where financial planning services can help you take a more strategic approach. The right plan can align your lifestyle goals with your financial reality.

It’s also wise to work with experienced wealth planners who can tailor retirement strategies based on your situation, including healthcare planning, income streams, and legacy goals.

So, how do you decide when you should retire?

While we can’t give you a specific retirement age, we can recommend you ask yourself these four questions before putting a retirement date on the calendar.

1. Have I Saved Enough?

This is probably the most important question you should be asking yourself before retiring. After all, a successful retirement largely hinges on the ability to financially provide for all your goals. But how can you really know how much you’ll need? A general guideline to calculate how much you need is to multiply your desired annual income in retirement by 25. Basically, that means you’re planning for a 25-year-long retirement.

For example, if you and your spouse plan on doing nothing but relaxing and focusing on your hobbies (and playing the occasional round of golf), then maybe you two can get by on something like $40,000 per year. Using our “rule of 25,” that means you should have about $1 million saved up across your various accounts to last you through your retirement.

But what if you’re dreaming of doing some serious traveling? What if you two decide you want to buy or rent a second place of residence? If that’s the case, you’ll need to increase your annual income estimates, which will greatly increase how much you should have saved up. Even increasing your estimated annual income by just $5,000 will boost the total amount you’ll need to have saved for retirement by $125,000.

While the 25x benchmark isn’t written in stone, and the amount you’ll spend each year for lifestyle and health care expenses is sure to fluctuate, these are still good things to keep in mind when determining if you’ve saved enough.

2. What’s My Plan for Health Care Coverage Beyond Medicare?

One of the most overlooked aspects of retirement planning is health care. No one wants to think that they’ll have health problems, but the reality is that you’ll likely need to plan for medical costs–both as you retire and later on down the road.

If you retire after age 65, while you’ll still likely have additional medical expenses, Medicare will provide a strong foundation for your health insurance needs. But if you retire prior to age 65, you’ll need to think about where you’ll get your health insurance if your employer doesn’t offer retiree medical insurance. COBRA or a private policy can help fill in the gaps, but both can be pricey.

Besides paying for basic medical coverage and health insurance, it’s also a wise move to plan for long-term care (LTC). Medical advances are allowing people to live longer, but the older you get, the more likely it is that you’ll need LTC. The need for extended LTC can quickly deplete your assets and their ability to generate income. However, having a fine-tuned financial plan that includes a strategy to pay for LTC can prepare you for a life-changing event.

3. Have I Thought About Social Security?

If you haven’t thought much about Social Security when planning for retirement, now’s the time to start. Not only is it a benefit afforded to just about every American, but it may also end up being a significant part of your retirement. According to the Social Security Administration (SSA), in 2020, Social Security benefits represented about 33% of income for those age 65 and older.

Retiring earlier may mean you’ll have to claim your benefits earlier, leading to a permanently reduced benefit. On the other hand, working longer can provide the flexibility to delay receiving your benefits, allowing them to grow until you reach age 70–at which point you can permanently receive more than 100% of your benefit. While on the surface it may seem like the more prudent idea to wait to claim Social Security, your own situation will dictate how and when you should start receiving your benefits.

Additionally, you’ll want to pay attention to the annual cost of living adjustment (COLA), as it can increase how much you receive from your Social Security benefits.

4. How Does My Partner Feel About Me Retiring?

Do you and your significant other have the same retirement goals? If you haven’t had that conversation yet, it’s important to take the time to see if your retirement plans are aligned. Does your spouse want to have more free time to pursue a favorite hobby? Is working as long as possible your partner’s primary goal? Does your partner find more value in spending time with friends and family or greater financial security from a delayed retirement?

Choosing when to retire isn’t so much about a specific age as it is reaching the pre-retirement goals you and your significant other have set. The feeling of satisfaction that comes from having reached your goals is the best indication that you’re ready for retirement. And if you have any questions or concerns, reach out to your financial advisor for help laying out your retirement roadmap.

This article originally appeared on April 19, 2015 in the St. Paul Pioneer Press.

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