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Key questions for planning your retirement

Before thinking about how much you need to save, start with these basics

Some people are natural planners — always organized and ticking off the tasks on their lists as they move through the day. For the rest of us, planning is not something that comes easily — and even less so when the subject is retirement.

There are a lot of questions to answer about retirement planning and things to think through. It can be tough to know how and where to start.

That’s why it’s helpful to start retirement planning by asking some basic questions to help you organize your thoughts. From there, you can start determining how to set the stage for the retirement you've envisioned.

Remember, planning for your retirement is a process and it will take time. You probably won’t be able to answer every question in detail right away — so revisit them periodically and begin to fill in the blanks as your goals for the future begin to take shape.

1. What do you plan to do with your time in retirement?

This seems like an obvious question, yet many people don't take the time to think it through. And, assuming you live a healthy 20- or 30-year retirement, you’ll have a lot of time to fill.

Let’s put the subject of money aside for a moment and envision the lifestyle that would make you happiest.

Is it full of travel and adventure? Artistic endeavors? Finding new ways to give back to the community? Starting your own business or a second career? Or would you be happier remaining close to home, hosting family gatherings and having fun with your grandchildren?

Make a list of the things you want to pursue in retirement and think about general timeframes and logistics.

Will your spouse join you? How long do you estimate you’ll be able to engage physically in each activity?

Your answers will help determine the amount of retirement savings you’ll need to fund your lifestyle. And if you need some help thinking about what you may want out of retirement, try our retirement personality quiz to see what sounds good to you.

2. Will you work in retirement?

For many retirees, retirement may not represent a distinct break between working and not working. 

Today, many people continue to work beyond typical retirement age — some out of necessity, while others simply enjoy the sense of purpose, social interaction and achievement that working can provide. If you're used to working full time, suddenly not working at all may feel abrupt and even a bit lonely — so continuing to do some kind of work can make the transition smoother.

Some people transition into retirement over a longer period, choosing part-time work or volunteering. Others will test their entrepreneurial spirit with a new business venture.

Obviously, whether you continue to work in retirement may have a significant impact on your financial plan.

While it would seem that continuing to earn an income as a senior would prevent you from having to save as much early on, it may also make you ineligible to collect Social Security while you are working.

Be sure to think through all the pros and cons of continuing to work in retirement. It may be wise to consult with a financial professional to ensure you are aware of all the angles.

3. Who will depend on you for personal and financial support?

Roles and norms that characterize the American family are changing. It’s becoming more common for children to live with their parents well into their 20s, or circumstances forcing a return to "the nest" after previously moving out on their own.

Many pre-retirees find themselves providing support or care for their own parents. And with soaring childcare costs, grandparents may need or want to take on a larger role in raising grandchildren.

While many of these situations happen suddenly and unexpectedly, it may be possible for you to take measures to plan for or avoid these circumstances by having conversations with your children.

Thinking about it now and exploring the potential cost of supporting loved ones can help you formulate your financial and lifestyle plan accordingly.

4. Where will you live once retired?

To a great extent, your answers to the first three questions will help determine the answer to this one. If you plan to continue working or want to be close to your family, you may need to stay put.

For retirees who choose to move somewhere new, that decision can have a big impact on finances. Consider whether it makes sense to remain in your current home, relocate or downsize. If you plan to travel often or for extended periods of time, maybe renting makes more sense. Or consider renting out your home while you're not there for extra income.

Knowing where you plan to live geographically is important, as well. Cost of living can vary widely from city to city and country to country.

If your heart is set on living in Midtown Manhattan, you’ll need to approach your financial plan differently than if you intend to live in a place with a lower cost of living, like Wyoming — or an even more budget-friendly place — like Ecuador.

5. What does your family think of your plan?

After thinking about your dreams, consider that your family may have some dreams of their own for your retirement. You've been busy working for many years now — so they may relish a little extra time with you, and be really thankful to have some help with grandkids, too.

Unless you've already been talking about your plans, they will have made some assumptions about how you will be spending your retirement. 

Having a conversation about your plans will help everyone start thinking about the impact this big life change will have on the entire family — especially if you're planning to be even busier in retirement than your working years — and set everyone up for success.

Enlist the help of a professional

While these key questions can help you plan your life in retirement, there are many financial questions to answer, too.

At what age should you begin taking Social Security? What’s the best move to make with your 401(k) once you’ve retired? What is the best strategy to establish a steady, reliable income stream?

Consider consulting a financial professional who is familiar with the ins and outs of retirement planning, distributions and taxes to share your plans and ensure that you’re on course to achieve your goals.

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