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.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.
Sign up for Kiplinger’s Free 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
- Four Steps to Help You Have a Comfortable Retirement
- Seven Habits for a Happy Retirement
- To Create a Happy Retirement, Start With the Three Ps
- Making Your Retirement Savings Last: Three Key Questions to Ask
- How Do You Stack Up When It Comes to Retirement?
-
I'm a Retirement Psychologist: Here's Why Doing What You 'Ought' in Retirement Beats Doing Whatever You WantTrue retirement freedom isn't about simply doing whatever you want, but about finding purpose and direction through commitments that align with your deepest values and allow you to contribute meaningfully.
-
Tactical Roth Conversions: Why 2025-2028 Is a Critical Window for RetireesThe One Big Beautiful Bill (OBBB) extended today's low tax brackets, but they may not last. Here's how smart planning now can prevent costly tax surprises later.
-
Ready to Retire? It's Not Too Late to Convert to a Roth IRAMillions of Americans are turning 65 this year. If you're retiring soon, don't dismiss the idea of a Roth conversion — it could still be a smart move even now.
-
I'm a Financial Adviser: Three Things You Will Wish You Did Before the Fed Cuts Interest RatesWith potential interest rate cuts on the horizon, you might want to lock in today's higher yields and consider adjusting your asset allocation.
-
Simple Ways to Save on Back-to-School Shopping This YearSet a budget and stick to it, scour the house for what you already have, decorate backpacks and lunch boxes with your kids and consider buying some items during holiday sales.
-
The Seven-Day Financial Reset: A Simple Plan to Get Control of Your Money, From an ExpertSometimes, getting unstuck requires a reset. These practical steps can help you tackle your money issues and feel less overwhelmed by it all.
-
Three Pros (and Four Cons) of Hiring Multiple Financial Advisers: The View From a Financial AdviserThere's nothing to stop you from working with several financial advisers instead of just one. But take a balanced view of the risks and rewards first.
-
I'm an Annuities Expert: Here Are Two Ways to Use Annuities to Benefit From the OBBBTo qualify for a new tax break included in the One Big Beautiful Bill Act, some older adults need to lower their taxable income. Annuities can make that happen.
