Proactive Retirement Planning: Smart Moves to Avoid Common Regrets

Retirement is something most people look forward to—and the great news is, you can still shape the experience you want. While most people don’t regret retiring, they may wish they made different decisions along the way.¹ Common reflections include:

“I wish I started saving earlier.”

“I didn’t realize long-term care would matter.”

“I should have waited to claim Social Security.”

These reflections aren’t setbacks; they’re valuable insights that can guide smarter decisions moving forward. The reality of our choices is sobering when it’s tied to our potential freedom and options. Every choice you make today shapes the freedom you’ll enjoy tomorrow.

So, what are the most common retirement regrets—and how can you turn them into smart moves starting now? 

The Power of Starting Early

Save on Schedule

Retirement doesn't feel urgent… until it's right in front of you.

One of the biggest regrets? Not saving earlier. And here's the math that illustrates why: if you save $1,000 a month starting at age 40, with a 7% return, you could potentially build a nest egg worth around $758,000 by 65.* But if you wait until 50? You'd need to save approximately $2,520 a month to reach a similar goal. That's the potential cost of waiting. 

Start smaller. Start now. Automate it. Every dollar today may help create more flexibility tomorrow.

Consider Your Benefits Timeline

Time Your Benefits Strategically

Many people claim Social Security the moment they're eligible. Not realizing that early move locks in a lower monthly check for life. Waiting until age 70 can raise your monthly benefits by about 32%.² That's not a small bump—it's the difference between making ends meet and having extra breathing room.

Delaying won't be right for everyone. But if your situation allows, waiting may increase your benefits over time. 

Seek the assistance of a financial professional. We can evaluate your specific circumstances, weigh your options, and ensure your claiming strategy aligns with your broader retirement goals and needs.

Managing Debt Before Retirement

Put Debt on a Deadline

Carrying debt into retirement may potentially limit your choices. It could keep money tied up in interest instead of letting you use it where it counts.

If you still have a mortgage, credit cards, or car loans, create a payoff plan now. Pick a target date and set up extra automatic payments. Each balance you pay off may offer more flexibility in the future.

A retirement with fewer financial obligations often provides more peace of mind.

Planning for Long-Term Care Needs

Decide Long-Term Care on Purpose

Many people believe Medicare will cover nursing home care—it doesn’t.³

And most haven’t named someone to make medical decisions on their behalf. When something unexpected happens, families are often left making difficult decisions under stress, without clear direction.

Planning ahead allows you to take control. A well-designed long-term care strategy can help protect your financial resources, preserve more choices, and provide clarity and confidence for the people you care about most.

Keep Options Open with Work

Extend Optionality

Not everyone wants to work longer—but some retirees later wish they had. Working a few additional years or transitioning to part-time, can stretch savings, delay withdrawals, and reduce financial pressure. Think of it as adding time to the game clock.

This approach isn't right for everyone. Your health, goals, and personal circumstances should always guide the decision. 

It's not about never retiring. It's about preserving flexibility and having more options when life throws a curveball. 

Your Career Path Matters, Too

Play Offense with Your Career

Not everyone leaves the workforce on their own terms. Some are forced out earlier than expected after staying too long in stalled roles, letting skills grow outdated, or neglecting their professional network.⁴

Staying proactive—by continuing to build skills, nurturing connections, or exploring new opportunities—can help protect you from being caught off guard. A strong career strategy isn’t just about advancement; it’s about resilience.

One of the best defenses against an unexpected career shift is staying engaged and continuing to move forward with intention.Top of Form

Bottom of Form

Life’s Not Just About the Numbers

Enjoy the Good Stuff

Some regrets don’t show up on balance sheets. They show up in stories that never happened. Trips that never got booked. Experiences that were saved “for later”… and never taken.⁵

Health changes. Priorities shift. That’s why building a plan that lets you enjoy life now—without sacrificing the future—can be so powerful.

Money is a tool that can be used to create memories, not just security.

Consider Professional Guidance

Call the Right Plays Together

Even well-prepared retirees often say they missed important details—underestimating how much they would need, misunderstanding survivor benefits, or overlooking how withdrawal rules and taxes could affect their income.

Over time, these factors can significantly impact a hard-earned nest egg. At Veridian Capital Partners, we help individuals and families think through what truly matters when navigating how—and when—you want to retire.

By working together, we can help identify potential gaps, clarify tradeoffs, and address key decisions before they become more difficult to manage—so your retirement plan is built with intention, confidence, and flexibility.

Bringing It Together

What decision would future-you thank present-you for?

Retirement planning isn’t about perfection. It’s about progress.

Automate your savings. Talk about long-term care. Rethink your timeline for claiming benefits. Pick one move to start with—then build from there. A few intentional plays today can mean more freedom, fewer regrets, and a retirement that truly fits your values.

Are you ready to talk through your retirement planning questions? We can help you explore your options and create a strategy that fits your unique situation.

*Assumes consistent monthly contributions and a 7% average annual return, compounded annually. This is a hypothetical example for illustrative purposes only. Actual performance will vary. Past performance does not guarantee future results.


 

Sources:

1. Bankrate, 2025 [URL: https://www.bankrate.com/f/102997/x/e4980803dd/august-fsp-press-release-8-20.pdf]
2. Social Security Administration, 2025 [URL: https://www.ssa.gov/benefits/retirement/planner/1943-delay.html?utm_source=chatgpt.com]
3. The Institute for Healthcare Policy and Innovation, 2025 [URL: https://ihpi.umich.edu/national-poll-healthy-aging/reports-and-resources/long-term-care-are-older-adults-ready]
4. Business Insider, 2024 [URL: https://www.businessinsider.com/older-americans-regret-retirement-savings-taking-social-security-early-investments-2024-10]
5. Nasdaq, 2024 [URL: https://www.nasdaq.com/articles/6-reasons-retirees-regret-not-traveling-more-retirement]

Disclosure: This content is developed from sources believed to be providing accurate information. The information provided is not written or intended as tax or legal advice and may not be relied on for purposes of avoiding any Federal tax penalties. Individuals are encouraged to seek advice from their own tax or legal counsel. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel. Neither the information presented nor any opinion expressed constitutes a representation by us of a specific investment or the purchase or sale of any securities. Asset allocation and diversification do not ensure a profit or protect against loss in declining markets. This material was developed and produced by Advisor Websites to provide information on a topic that may be of interest. Copyright 2025 Advisor Websites.