As you near retirement age and are considering whether it’s time to take the plunge into the next phase in life, it’s normal to feel overwhelmed by the possibilities and uncertainties. The most important — and often overlooked — step in the process is looking back before looking forward to decide what your bigger future holds. I’ve come up with five guiding questions for soon-to-be retirees to ask themselves to ensure they are well prepared and feeling confident in their journey — opportunities, challenges and all.
Question #1: What wins (personal, career and financial) am I most proud of?
When you’re about to make a big life change, it helps to come to it from a place of gratitude. This helps you better envision your future in a clearer, more grounded way, rather than from a place of frustration and uncertainty. No matter your stage of life, there are wins, big and small, that you can point to and take stock of.
By doing this exercise, what I describe as measuring backward, you’re able to feel more confident to take the next big, daunting step in your journey, remembering all you’ve accomplished before and validating your achievements.
Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Question #2: Who will I be in retirement?
Sometimes it helps to get a little existential when it comes to planning some of the biggest changes in your life. I tell my clients to picture their 8-year-old self. What did that child enjoy without any major responsibilities? What would you do differently without the demands of a daily routine and alarm wake-up every morning? What would life look like without regard to money and resources?
Of course, this entails a bit of daydreaming, and I recognize that not everyone is in a position nearing retirement where they can make those dreams come true. However, there are certainly ways to bridge what you want for yourself and how you can make that happen.
I also find that the people who are most successful in retirement are the ones going toward something, not running from something.
What’s the biggest goal you have for yourself in this new stage? Is it spending more time with family, starting a new hobby or working with a charitable organization you never had the time to focus on? Those who set themselves up for exciting changes during this time are better prepared for this major transition.
Question #3: What are my biggest dangers?
Planning for retirement is stressful, and all the daydreaming and planning in the world cannot prevent the thoughts that keep us up at night. One of the biggest pieces of advice I give to my clients who are struggling to make a plan for retirement, or think they may not have enough to live the life they want to, is that it needs to be faced head on. These problems will not be solved by burying your head in the sand and avoiding them. Instead, work with a financial adviser to assess exactly where you are and outline a plan to get to where you’d like to be.
As for the unknowns, unfortunately there’s no surefire way to avoid geopolitical issues, inflation, health concerns, family riffs or anything else that keeps you up at night. Again, these things should not be ignored and instead should be planned for.
There are plenty of ways to mitigate some of the risks or dangers that could bubble up in your lifetime. They may end up not being a problem, but at least you’ll be prepared should they rear their head during retirement.
Question #4: How do I maximize my opportunities?
While there are plenty of tactical ways to make sure you’re well set up from a financial perspective for retirement, it’s important to remember that just because you’re retiring doesn’t mean you need to change how you operate every aspect of your life.
I always remind my clients that while they’re moving on to a new phase of their lives, it’s not a short period of time. You could have 30 years ahead of you!
That being said, retirement is a great time to take stock, potentially rethink your asset allocation based on what you’ll need to live on now, coupled with your tolerance for risk. This could be the most money you have in your life, so of course you’ll want to make sure it’s working for you as you make this change.
Question #5: How do I maximize my strengths?
As a society, we don’t give ourselves enough credit. This is why I think measuring backward, coming from a place of gratitude and thinking of our strengths are so important. Think about the successes, characteristics or habits that got you to where you are. Maybe you’ve been a good saver all your life. How can you make that work for you in retirement? Maybe you have a strong network of friends and family. How can you lean on those people?
At the end of the day, retirement can be equally as overwhelming as it is exciting. This is your reminder to take a step back and to take stock of your life so far. What do you want these next (hopefully) 30 years to look like?
By focusing on the positive, you’re more likely to approach your plan for the future with a bit more gratitude. Working with a financial adviser can help you answer these questions, open the door to some challenging but important conversations and set you on the right path for your next chapter.
related content
-
Stock Market Today: Stocks Stable as Inflation, Tariff Fears EbbConstructive trade war talks and improving consumer expectations are a healthy combination for financial markets.
-
What Trump’s 'Big Beautiful Bill' Means for Your Utility BillsIf passed, the 'Big Beautiful Bill' could make home energy upgrades more expensive and raise monthly costs. Here's how much more you might pay and how to prepare.
-
Eight Estate Planning Steps to Protect Your Loved Ones (and Your Legacy)Two-thirds of Americans don't have an estate plan. If you're one of them, these are the essential steps to take now to prevent problems for your family later.
-
The Six Pros This Adviser Says You Need to Sell Your BusinessSelling your business isn't as simple as getting the best price and walking away. These are the six professionals you'll need to get a deal across the finish line.
-
The Three C's to Financial Success: A Financial Planner's Guide to Build WealthConsistency, commitment and confidence in your chosen strategy are more critical to your financial success than finding the 'perfect' financial plan.
-
A Financial Adviser's Guide to Solving Your Retirement Puzzle: Five Key PiecesIf retirement's a puzzle you're struggling with, try answering these five questions. The answers will guide you toward a solution.
-
You're Close to Retirement and Cashed Out: How Do You Get Back In?If you've been scared into an all-cash position, it's wise to consider reinvesting your money in the markets. Here's how a financial planner recommends you can get back in the saddle.
-
After the Disaster: An Expert's Guide to Deciding Whether to Rebuild or RelocateHomeowners hit by disaster must weigh the emotional desire to rebuild against the financial realities of insurance coverage, unexpected costs and future risk.
-
A Financial Expert's Tips for Lending Money to Family and FriendsWhat starts as a lifeline can turn into a minefield if the borrower ghosts the lender. Following these three steps can help you avoid family feuds over funds.
-
What the HECM? Combine It With a QLAC and See What HappensCombining a reverse mortgage known as a HECM with a QLAC (qualifying longevity annuity contract) can provide longevity protection, tax savings and liquidity for unplanned expenses.
