5 Questions to Help You Start Planning Your Dream Retirement

Resolutions are always top-of-mind as a new year rolls around and saving more money is reliably one of the most cited. But when it comes to your retirement, if you’re consistently socking away a portion of your hard-earned cash into an IRA, 401(k) or another tax-advantaged savings plan, then you likely already know how important it is to save for the day you bid farewell to your 9-to-5. But do you have a clear vision of what your dream retirement actually looks like?

You may have an idea of how you want to feel in retirement — namely, less stressed and free to pursue all the things you didn’t have time for while working — but those are still vague notions. And the closer you get to retirement, the more detailed your vision should be; that way, you’ll be better able to tell if you’re on track to achieve it.

So if you’ve never taken the time to think through what retirement looks like for you, it’s never too late to start. This list can help.

Envisioning your retirement: The 5 W’s

We know what you’re thinking — you can barely find the time to plan your next vacation, let alone your retirement. If you’re having trouble honing your vision, use a method that journalists use to help refine their stories: the 5 W’s, or who, what, where, when and why.

Who will share your retirement with you? Are you planning for yourself, or with a spouse or partner? If you’re planning with two people in mind, ask your significant other what his or her dream retirement looks like. The closer you are to retirement, the more important it is to figure out your differences.

What do you want to spend your time doing? You may already be daydreaming about traveling to exotic locales, growing your garden or starting a new side gig. Think about how you spend your free time now. Do you want the freedom to do more of the same or do you want to pursue new adventures? Will your activities be local or take you around the world?

Where do you want to live? Perhaps you dream of growing old in your current home, or want to downsize to a smaller house now that all the kids are out of the nest. Maybe the idea of taking up residence in a retirement community with on-site activities is appealing to you, or you’re intrigued by the thought of moving overseas. This is important to think about because where you live will dictate a lot of your day-to-day living costs.

When do you want to retire? Of course, when you choose to retire may not necessarily be up to you; changes at work or with your health may cause you to retire earlier than you anticipated. But in an ideal situation, when would you want to retire? Do want to start on the earlier side so you can get a jumpstart on the next phase of your life — or do you envision working well into your 70s or beyond?

Why do you want to retire? This may seem like a no-brainer, but maybe you’re not looking to retire in the traditional sense. Not everyone is emotionally prepared to say goodbye to their work and the sense of purpose it provides. If that sounds like you, you may envision your retirement as less of a hard stop and more of a transition, or a phased retirement, where you move from full-time to part-time hours, or from working in one long-standing career to pursuing a new passion.

RELATED CONTENT: How much do I need for retirement? Our retirement planning guide can help you better understand the road to retirement — and how to craft a financial plan that’s built around your unique goals.

How you can help make it happen

Once you have an idea of what your retirement looks like, it’s time for a little retirement reality check: Do you have a plan to get there? It's common to save and just hope that you’re doing enough, but a real retirement strategy goes beyond saving.

Working with a financial advisor can help. They can run some numbers for you to help you determine if you’re on track to maintain the retirement lifestyle you want — and help you weigh your options if you need to do some catch up.

Based on your retirement vision, you can discuss how much you’ll need to budget to cover both discretionary costs and necessary expenses like housing and health care. An advisor can also put together a plan for you that includes diverse retirement income sources, ranging from 401(k)s and IRAs, to Social Security benefits, to annuities and cash value permanent life insurance.¹ The goal is to help make your money last in retirement in as tax-efficient a way as possible. 

Of course, your retirement dreams can and probably will change through the years. A financial advisor can help provide guidance about how to evaluate and adjust your portfolio and income sources if your goals do change. With some smart financial decision-making, you can help ensure whatever you dream becomes reality.