Four Questions That Keep Most Pre-Retirees Awake at Night
If you worry about when you can retire, whether you'll have enough money, whether the money you do have will last… Well, you are not alone.
As we approach the latter years of our career, thoughts of what retirement will look like can be a source of mixed emotions.
For many, this will be a time to dream about doing those things on their bucket list they’ve been waiting to do. It could be traveling abroad, learning a fun hobby, making memories with grandchildren or pursuing a new business venture. For others, this could also be a time of stress and uncertainty, given how much of our identity has been tied to our career success and advancement.
We have routines and structures that we have followed for years, and now we face the reality that that is all about to change.
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.
For people approaching this next phase of life, there are four questions that will keep people awake at night as they search for answers. Over the years, I’ve found that these four questions can encompass what many pre-retirees feel the need to know and be prepared for. Knowing the answers to these questions can provide confidence that people are prepared to make this a good transition.
Question #1: When can I retire?
This seems like one of the most universal questions everyone will ask themselves at some point, but how do we actually know when we should begin this next phase of life? Do we seek direction from friends, family and colleagues to help guide us? Maybe it’s our health that dictates our decision.
Back in our parents’ (or grandparents’) day, life seemed much simpler, and this question might have been easier to answer. Work for 40 to 50 years often for the same company), make a pension election when eligible, file for Social Security and ride off into the sunset.
However, with the traditional pension becoming more a thing of the past, the answer may not be so obvious today. In addition, don’t overlook the emotional piece of retirement. The happiest people in retirement retire “to” something vs retiring “from” something.
Having, on average, three to four pursuits can prevent boredom in retirement and bring purpose and meaning to daily life. As your retirement window approaches, brainstorm each week about what pursuits you may enjoy and allow yourself to look forward to getting started. Let your mind dream big and don’t be afraid to try something you never thought you would do. Go for it!
Question #2: Will I have enough money?
What is the magic number that makes it OK to retire? More important, what is your magic number? Emotionally, it can be tied to a vision you’ve had your entire career, such as accumulating $1 million or paying off your mortgage. Maybe it’s selling a business you’ve worked years to build or inheriting a large lump sum.
However, there is certainly no one-size-fits-all answer to this question. Begin by having a budget specific to retirement and understand what percentage of your monthly expenses can be covered by fixed sources of income, such as Social Security, a pension, annuities, etc.
Also, make sure to separate the purpose of your money and specifically dedicate it to such things as creating monthly income, covering future health care costs and growth to try to outpace inflation. By separating the purpose of your nest egg, you will be better able to allocate your portfolio appropriately among various tools, such as savings, investments, annuities and life insurance, to name just a few.
Question #3: Will my money last?
Will my nest egg last throughout retirement? A possible risk for retirees is the potential of having negative returns in their investment portfolio during their early years of retirement.
During your working years, you may have regularly contributed money to your retirement plan. Now, as you enter retirement, you might instead need to consider making regular withdrawals from these savings to generate income.
This is referred to as a sequence of returns risk, and the potential impact on the order of yearly gains and losses could have on a retirement portfolio. For example, early negative returns, particularly in the first few years of retirement, could affect how long savings last while also making withdrawals for income. Additionally, for example, even with the same average return over time, a different order of market ups and downs may lead to different outcomes.
A possible way to manage this risk is to try to avoid taking systematic distributions from a fluctuating account. You may also want to consider dedicating a portion of your portfolio to create the monthly income needed to cover fixed expenses that are beyond what your Social Security and pension, if you have one, will provide. Once you know this number, you are ready to determine what combination of investments and insurance tools are right for you.
Question #4: Will my spouse be OK?
This is especially relevant for most couples. We all want to know that if we pass away, our spouse will be OK and will be able to carry on. It’s even more important to know the answer to this question if the spouse who passes first was the one who took care of overseeing all the family finances. Most often, one person in the relationship takes on this responsibility, which can provide organization and a sense of order in the household.
However, it’s essential to ensure that both spouses are comfortable with the family financial adviser and where to turn when life happens. Trust can take years to develop, so make this a priority while you are both healthy and able. Meet often enough to develop the trust needed for both partners to feel comfortable.
Knowing the answers to these four questions can provide the foundation for an amazing retirement.
Investment Advisory Services offered through Trek Financial LLC, an investment adviser registered with the Securities Exchange Commission. Information presented is for educational purposes only. It should not be considered specific investment advice, does not take into consideration your specific situation, and does not intend to make an offer or solicitation for the sale or purchase of any securities or investment strategies. Investments involve risk and are not guaranteed, and past performance is no guarantee of future results. For specific tax advice on any strategy, consult with a qualified tax professional before implementing any strategy discussed herein. Trek 24-371
Related Content
Get Kiplinger Today newsletter — free
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.
Nicholas Toman, CFP®, is a lead retirement planner and investment adviser with Empowered Financial Management, a firm that specializes in retirement planning for those individuals within five to seven years of retirement or who have recently retired and no longer wish to serve as their own financial adviser. Nicholas is a graduate of the University of Wisconsin-Whitewater with a BBA in accounting and has been a Certified Financial Planner since 2014.
-
Stock Market Today: Dow Leads as UnitedHealth Stock Pops
UnitedHealth was the best Dow Jones stock Monday on reports that Medicare Advantage payments could rise in 2026.
By Karee Venema Published
-
Earnings Season: Live Updates and Commentary
Fourth-quarter earnings season is getting underway, and Wall Street is keeping a close eye on both results and guidance.
By Kiplinger Staff Last updated
-
Stock Market Today: Dow Leads as UnitedHealth Stock Pops
UnitedHealth was the best Dow Jones stock Monday on reports that Medicare Advantage payments could rise in 2026.
By Karee Venema Published
-
How to Organize Your Financial Life (and Paperwork)
To simplify the future for yourself and your heirs, put a financial contingency plan in place. The peace of mind you'll get is well worth the effort.
By Leslie Gillin Bohner Published
-
Financial Confidence? It's Just Good Planning, Boomers Say
Baby Boomers may have hit the jackpot money-wise, but many attribute their wealth to financial planning and professional advice rather than good timing.
By Joe Vietri, Charles Schwab Published
-
Average Cost of Health Care by Age
Expect to pay more as you age. We've got solutions for how to cover these costs, which can exceed $1,000 per month in your 60s.
By Adam Shell Published
-
Will You Be Able to Afford Your Dream Retirement?
You might need to save more than you think you do. Here are some expenses that might be larger than you expect, along with ways to ensure you save enough.
By Stacy Francis, CFP®, CDFA®, CES™ Published
-
Three Steps to Simplify Paying Your Taxes in Retirement
Once you retire, how you pay some of your taxes can change. Here's how to get a handle on them so you don't run afoul of the IRS and face penalties.
By Evan T. Beach, CFP®, AWMA® Published
-
Should You Add an Annuity to Your Retirement Portfolio in 2025?
In need of some guaranteed income? An annuity may be the answer if you check off any of these boxes.
By Donna Fuscaldo Published
-
More SECURE 2.0 Retirement Enhancements Kick in This Year
Saving for retirement gets a boost with these SECURE 2.0 Act provisions that are starting in 2025.
By Mike Dullaghan, AIF® Published