The 4 Biggest Retirement Regrets: What Financial Advisors Wish You Knew Before It's Too Late

The quick scan: Thursday delivered another milestone session, with the S&P 500 crossing 6,500 for the first time and notching its second consecutive record close, while the Dow also hit fresh highs despite Nvidia's post-earnings slip. The historic performance demonstrated how markets can achieve new peaks through consistent progress and strong fundamentals—much like today's lifestyle wisdom about retirement regrets, which shows that the biggest mistakes aren't about market timing or investment selection, but about timing life itself and knowing when to actually enjoy the wealth you've built.

• S&P 500: Rose 0.32% to a record close of 6,501.86, crossing the psychologically important 6,500 level for the first time and marking its 20th record high of the year
• Dow Jones: Advanced 0.2% to 45,465.23, achieving its second record high of 2025 as broad-based strength supported traditional sectors
• NASDAQ: Climbed 0.53% despite Nvidia's post-earnings decline, showing resilience in the tech sector as other names picked up the slack

What's driving it: Strong GDP data showing better-than-expected economic growth overshadowed concerns about Nvidia's guidance, while falling Treasury yields supported equity valuations. The market's ability to look past individual disappointments to focus on broader economic strength reflected mature, long-term thinking.

Bottom line: Thursday's record-breaking performance amid mixed earnings news perfectly mirrors today's lifestyle theme about retirement regrets—just as markets achieve their best results through consistent, long-term focus rather than perfect timing, the most fulfilling retirements come from balancing prudent planning with the wisdom to enjoy life along the way.

The 4 Biggest Retirement Regrets: What Financial Advisors Wish You Knew Before It's Too Late

The scoop: A financial advisor who has guided hundreds of clients into retirement reveals the four most common regrets she encounters. The biggest mistakes aren't about investment choices or savings rates—they're about waiting too long to retire, not spending money earlier in life, failing to track progress, and lacking tax diversification. For L-Plate retirees, these insights offer a roadmap for avoiding the heartbreak of missed opportunities and creating a retirement that's not just financially secure, but deeply fulfilling.

The wake-up call

Anna N'Jie-Konte has walked hundreds of people into retirement as a financial advisor, and she's noticed a troubling pattern. While the technical side of retirement planning often gets executed flawlessly, it's the human side—the fulfilment, the timing, the actual living—where people consistently miss the mark.

"A financially secure retirement means nothing if it's not also deeply fulfilling," N'Jie-Konte observes. These aren't regrets about picking wrong stocks or not saving enough—they're deeper, more painful regrets about life choices that can't be undone.

Regret #1: Waiting too long to retire

This regret comes up "over and over," and it's heart-breaking in its frequency. We all know the stories: people who worked hard, saved diligently, and finally reached retirement—only to fall ill or pass away soon after.

The problem runs deeper than bad luck. "So many of us are taught to delay gratification, keep pushing, and believe retirement is when we're finally 'allowed' to have joy," N'Jie-Konte explains. We neglect our mental and physical health during working years, postponing leisure, travel, and family time until some magical future date.

For L-Plate retirees, this offers a crucial lesson: retirement isn't just about having enough money—it's about having enough time and health to enjoy it. The question isn't just "Can I afford to retire?" but "Can I afford not to retire while I'm still healthy enough to enjoy it?"

Regret #2: Not spending more earlier in life

N'Jie-Konte's aunt was financially responsible and had saved more than enough for retirement, but she "worried about every dollar spent." When she died at 72, she left behind a heart-breaking list of unfulfilled dreams: a train trip through New England to see fall foliage, adding a sunroom to overlook her garden, and many other experiences that never materialized.

"These may seem like small or 'extra' things, but they were her desires that went unfulfilled because she prioritized caution over joy," N'Jie-Konte reflects.

This regret highlights a fundamental misunderstanding: being financially responsible isn't the same as living a full life. The goal isn't to die with the most money—it's to use money as a tool for creating meaningful experiences.

For L-Plate retirees, this means finding balance between prudent saving and purposeful spending. Some experiences are time-sensitive and can't be postponed indefinitely. Your 60-year-old self might handle that European walking tour better than your 80-year-old self.

Regret #3: Not tracking progress earlier

This regret usually emerges quietly, buried under the anxious question: "Did I save enough?" When people don't track their financial progress, they either over save and miss opportunities for joy, or under save and enter retirement with anxiety.

N'Jie-Konte's solution: "Define your personal 'bucket list' early. What experiences do you want to have? What memories do you want to create? Don't just identify these things—schedule them. Budget for them. Make them real while you still have your health and loved ones."

This transforms retirement planning from a purely financial exercise into life design. Instead of just accumulating money, you're planning for specific experiences and goals.

For L-Plate retirees, this means creating two parallel tracks: your financial plan and your life plan. Track both your net worth and your progress toward meaningful experiences.

Regret #4: Lack of tax diversification

N'Jie-Konte sees too many retirees with all their savings in pre-tax accounts like traditional IRAs and 401(k)s. While this reduces current tax burden, it creates problems in retirement when every withdrawal becomes taxable.

"That $5,000 car repair? You'll need to pull out closer to $7,000 or more to cover it, once taxes are factored in," she explains. She recalls a client with 100% of assets in pre-tax accounts who had to take out 30-40% more than expected for every expense.

The solution is building a mix of account types:
•Pre-tax accounts (traditional IRAs and 401(k)s)
•Tax-free accounts (Roth IRAs, HSAs)
•Taxable brokerage accounts

This diversification gives you flexibility to make strategic withdrawals, manage your tax bracket, and avoid unnecessary penalties.

The deeper lesson: Permission to live fully

All four regrets point to a deeper truth: the biggest regret isn't about money—it's about missed opportunities to live fully. "It's about not living fully, not planning with intention, and not giving yourself permission to enjoy what you've built," N'Jie-Konte says.

We're taught that responsible people delay gratification, that enjoying money is irresponsible, and that retirement is the reward for decades of sacrifice. But this mindset can lead to a life where the reward never comes or comes too late.

For L-Plate retirees, the challenge is reframing retirement planning as life planning. It's not just about accumulating enough money to stop working—it's about creating a life that balances security with fulfilment, prudence with joy, and planning with living.

Avoiding these regrets

Based on N'Jie-Konte's insights, here's how L-Plate retirees can avoid these regrets:

Start with your bucket list, not your budget. Build joy into your pre-retirement years. Track both wealth and experiences. Create tax flexibility early. Give yourself permission to enjoy your wealth. Consider phased retirement instead of working full-time until you stop completely.

The ultimate question: What would you regret not doing if your time or health ran out sooner than expected? This isn't about being reckless—it's about being intentional with your remaining years.

Actionable Takeaways for L-Plate Retirees:

• Create your bucket list now: Define specific experiences and goals, then schedule and budget for them rather than deferring them indefinitely.

• Balance saving with living: Build meaningful experiences into your pre-retirement years instead of waiting for future "permission" to enjoy life.

• Track life progress, not just wealth: Monitor progress toward meaningful goals alongside financial milestones.

• Diversify your tax strategy: Build a mix of pre-tax, tax-free, and taxable accounts to create flexibility in retirement.

• Consider phased retirement: Explore ways to gradually reduce work while increasing life enjoyment.

• Give yourself permission to spend: Use money intentionally for experiences that matter, recognizing that financial responsibility includes enjoying the wealth you've built.

Your Turn:
These retirement regrets reveal that the biggest mistakes aren't about money management, but about life management. They raise challenging questions for L-Plate retirees:

What dreams are you deferring until retirement? Are there experiences you're postponing that might be better enjoyed while you're younger and healthier?

How do you balance financial security with life enjoyment? Where do you draw the line between responsible saving and living fully in the present?

What would you regret not doing if your time ran out sooner than expected? This isn't about being morbid—it's about being intentional with your remaining years.

Have you given yourself permission to enjoy the wealth you've built? Or are you still operating under the belief that spending money on joy is irresponsible?

The L-Plate Retiree community would love to hear your thoughts on balancing security with fulfillment. Have you experienced any of these regrets, or found ways to avoid them?