Bold reality check: many retirees in their 70s and 80s discover costly regrets not from big investments gone wrong, but from gaps in planning that quietly widen over years. Even with careful retirement preparation, certain choices can slip through the cracks, leaving a gap between what was hoped for and what actually happens in those later decades. Instead of savoring time with grandkids or chasing travel dreams, some end up navigating a labyrinth of tax rules and income options just to bridge the shortfall created by past decisions—or in some cases, missed opportunities.
A seasoned financial adviser from Virginia puts it plainly: “Having a comprehensive plan is rarely something anyone regrets. Not having one almost always is.” To help readers steer clear of common missteps, The Independent spoke with several experts about the regrets most frequently voiced by retirees in their 70s and 80s, along with practical strategies to avoid them.
Not planning for incapacitation
People often keep death foremost in their minds, but they overlook what happens if illness or accident robs them of decision-making power. When there is no one legally authorized to handle finances or healthcare decisions, relatives can be left scrambling, which can lead to lasting regret. As attorney Lisa McCurdy—CEO of The Wealth Counselor—explains, that regret comes from preventable gaps in legal preparation.
“To prevent family chaos, set up two crucial documents while you’re still fully capable: a durable power of attorney for finances and a healthcare power of attorney or advance medical directive,” she says. The former designates a trusted person to manage money matters if you’re unable, while the latter names who can make medical decisions, approve procedures, and direct funds for long-term care.
“Choosing these decision-makers while you still have capacity means you determine who steps in, not a courtroom stepping in during a crisis.”
Not saving enough
Many people overestimate the savings they’ll need and underestimate how much they actually have saved. A Clever Real Estate survey found that while retirees often believe they need more than $800,000 to live comfortably, the average savings cited was only about $289,000. That gap is a frequent source of regret for retirees, according to Shelby Rothman, a certified financial planner and head of EnJoy Financial.
Rothman notes that clients frequently regret not prioritizing long-term saving earlier in life, instead chasing shorter-term goals like buying a home or starting a family. By the time retirement approaches, income streams may fall short of what’s needed, and there simply isn’t enough time for new contributions to meaningfully compound.
To avoid this, view Social Security as a supplement rather than the sole retirement income, and maximize savings as early as possible. If your employer offers a 401(k) match, contribute enough to capture that “free money.” Consistency matters—the longer your money is invested, the greater its growth potential.
Not hiring a financial professional
A common regret is delaying professional financial guidance until a crisis hits. After a thorough planning process, many retirees say they wish they’d started sooner, citing the clarity, structure, and long-term strategy that advisers provide.
The key misconception to challenge is the idea that financial planning is only for the wealthy or that it’s prohibitively expensive. If you can shift past the mental block, hiring a planner is often a wise investment. The timing you can’t predict—retirement approach, market shifts, or major life events—can be exactly when you wish you had a clear, sustainable plan in place. As one advisor compares it to hiring a personal trainer, people often don’t appreciate the value until they see a clear roadmap for sustaining income once the paycheck stops.
In short, building a lasting retirement isn’t about avoiding risks altogether; it’s about preparing for responsibility, clarity, and ongoing adaptability. Crafting a durable plan, securing power of attorney and healthcare directives, prioritizing early and consistent saving (including leveraging employer matches), and engaging a trusted financial professional are practical steps that help many retirees sidestep the common regrets that emerge in their later years.
What’s your take: do you agree that preparation and professional guidance are the keystones of a confident retirement, or do you think a more hands-on DIY approach can work just as well? Share your thoughts in the comments.
