If Only: The Top 10 Things Retirees Wish They Did Before They Retired
Two of the saddest words a retiree can say are "If only ..."
No one makes it through their entire life without a few missteps. But your Golden Years are supposed to be about enjoying the freedom, relationships, and, yes, money that you've spent decades cultivating.
The good news for pre-retirees is that regret isn't inevitable. If you learn from the experiences of seniors who've gone through some ups and downs already, you can plan ahead so you're not spending your retirement dwelling on do-overs.
Let’s explore ten of the most common "If onlys" I've heard in my 30-plus years as an advisor and how you can prepare to face them with clarity and confidence.
Lifestyle “If Onlys” — Designing a Life You Love
1. “If only I had tested my retirement lifestyle first.”
The Problem: Many seniors head into retirement with an “endless vacation” mindset: sleeping in every day, playing lots of golf, and lounging around the house. It might take weeks, months, or even a year, but sooner or later this “vacation” creates boredom and a lack of purpose.
At the other extreme, those who do set off to see the world often stretch their romanticized "retirement budget" too thin too fast.
The Plan: Take a retirement "test drive." A year or two ahead of retirement, reduce your working hours, go on a sabbatical, or cash in unused vacation time to simulate a couple of weeks of what you imagine retirement will be like. At the end of your test drive, assess how you feel about the time and money you spent.
2. “If only I had talked more with my spouse about what retirement would look like.”
The Problem: Spouses often don’t realize just how much time they’ve spent apart during their working years … until they’re suddenly spending all their time together. Once they’re stepping on each other’s toes and trying to rework their daily routines, they realize how different each person’s expectations were for retirement.
The Plan: Set aside time to have intentional, specific conversations about what you both want for retirement. Create a shared vision for what you want to do separately and together, and use that vision to design your ideal weeks and fill up your bucket lists.
3. “If only I had built a clearer plan for how to spend my time.”
The Problem: Engineering, architecture, medicine – to high-achievers, these aren’t just paychecks. They’re missions that provide identity and structure. When that mission ends at retirement, a void opens that leisure time can’t fill by itself.
The Fix: Repurpose your professional skills and continue “the mission” on your terms. Mentor young professionals. Explore teaching opportunities. Start a consulting company. Serve on the board of a nonprofit. Volunteer.
Health, Purpose, and Legacy “If Onlys” – Taking Care of What Matters Most
4. “If only I had taken my health more seriously earlier.”
The Problem: It’s far too easy to put your well-being last when you’re working 40+ hours every week and raising a family. All those skipped annual checkups and weeks without regular exercise will add up by the time you hit your 60s and 70s.
The Plan: Start small. Take a 10-minute walk every morning. Plan a weekly grocery trip so you’re cooking healthier meals and spending less time in the drive-thru. Schedule a visit with your doctor. Power down an hour before bed and get your eight hours of sleep. Stick with these habits and eventually they’ll build into a wellness routine that will improve your health span and your life span.
5. “If only I had strengthened my legacy plans.”
The Problem: No one likes to think about incapacitation or death. But far too many people put off making decisions about how they want to be cared for at the end of their lives and how their assets should be distributed. Others mistakenly think they’re not wealthy enough to need an estate plan. Instead of leaving behind a legacy, these folks often leave behind family fights and a legal mess.
The Fix: Don’t wait! Everyone needs a legacy plan. Work with your financial advisor and attorney to prepare the necessary documents. And review your legacy plan at least annually to make sure it’s still consistent with your wishes.
6. “If only I had diversified my sources of meaning — not just my portfolio.”
The Problem: If your identity becomes too wrapped up in work, what happens when you stop working? Repurposing your professional skills can only fill up so much of your time in retirement. What are you going to do when you’re not teaching or consulting? Who are you going to grab a cup of coffee with? Who will be at your holiday dinner table? When you do have to spend a few hours alone, how will you pass the time?
The Fix: Spouse. Parent. Grandparent. Friend. Artist. Athlete. Student. Start investing more time in these roles and you won’t just be retiring from work, you’ll be retiring to a life that’s even more fulfilling.
Financial “If Onlys” — Planning Beyond the Numbers
7. “If only I had downsized earlier.”
The Problem: The family house is a beloved home, filled with memories and familiar comforts. But it also has more empty bedrooms and closets than you can fill, a yard that’s getting harder to maintain, and bills (mortgage, taxes, insurance, upkeep) that are big line items on your retirement budget.
The Plan: Reimagine what “home” can mean. Downsizing ahead of retirement, or in the first couple of years, can be a freeing experience that provides a fresh start. Less overhead can give your budget more room to breathe, and more resources to accommodate a few more bucket list goals. And moving closer to friends and family could give you opportunities to make new memories with the people who matter the most.
8. “If only I had taken advantage of smarter tax planning.”
The Problem: During their working years, most folks are focused on earning, topping off their retirement accounts, and getting ready for tax season next April. But once you do retire and flip from accumulation to distribution, how and when you make withdrawals could affect not just your tax bill but your monthly Medicare premiums and your Social Security benefits.
The Fix: Diversify your assets across taxable and tax-advantaged accounts so that you can create a withdrawal strategy for every stage of retirement. During years when you’re earning less, consider strategic moves like Roth IRA conversions and tax-loss harvesting that will boost your long-term prospects and lower your lifetime tax liability.
9. “If only I had updated my financial plan one more time before retiring.”
The Problem: Many people coast towards retirement on a financial plan that they haven’t reviewed in years. Yes, they’re making automatic contributions every month to their savings and investment accounts. Sure, they’re paying down their mortgages. But as they’re nearing the end of their careers, they haven’t started planning for life without a paycheck. And as they transition into retirement, they’re often surprised at how normal inflation and rising health care costs can affect their ability to keep living their preferred lifestyle.
The Plan: Usually, there isn’t one! Or, folks who are managing their money solo don’t have the expertise they need to challenge their assumptions about retirement, identify blind spots, and prepare emotionally and financially for the next stage of their lives.
10. “If only I had worked with an advisor sooner.”
The Plan: Easy. Call Keen Wealth.
No matter where you are on your financial journey, the end of the year is a great time to schedule a financial review. Let’s talk about how our comprehensive planning process could help you turn “If only …” into “I’m so glad I did.”
About Bill
Bill Keen is a financial advisor with over 30 years of industry experience. As the founder and CEO of Keen Wealth Advisors, a registered investment advisory firm, he focuses on providing personalized retirement planning designed to help people thrive before and during their retirement years. With a passion for educating others, Bill regularly blogs about retirement planning, hosts the podcast Keen on Retirement, and has contributed to Forbes, U.S. News and World Report, Reuters, Wall Street Journal’s Market Watch, Yahoo Finance, and other publications. Based in Overland Park, Kansas, Bill and his team work with clients throughout the greater Kansas City area and across the nation. To learn more, connect with him on LinkedIn or visit www.keenwealthadvisors.com.
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