4 Biggest Retirement Regrets Financial Advisors See (And How to Avoid Them)

The quick scan: Happy Monday! While we're all easing back into the work week, the U.S. stock markets took a well-deserved break on Friday, July 4th, for the Independence Day holiday. This means there's no new market data from Friday's close to report.

What it means: Sometimes, even the busiest markets need a day off to celebrate freedom (and maybe catch up on some sleep). So, while we don't have fresh numbers, the break gives everyone a chance to reset before diving back into the action. We'll be back with the latest market movements tomorrow, based on today's trading. For now, enjoy the lingering holiday vibes!

The 4 Retirement Regrets That Keep Financial Advisors Up at Night (And How to Avoid Them)

The scoop: A financial advisor who's walked hundreds of people into retirement has seen enough regrets to write a cautionary tale that would make Shakespeare weep. Anna N'Jie-Konte reveals the four biggest regrets she encounters repeatedly, and they're not what you might expect. Spoiler alert: it's not just about money—though money definitely plays a starring role in this drama.

The most heart-breaking part? These regrets are entirely preventable, but they require making uncomfortable decisions while you're still working and dreaming of that magical retirement day. Think of it as retirement insurance for your soul—because having enough money means nothing if you don't have enough life left to enjoy it.

Here's the brutal truth: most people spend more time planning their annual vacation than they do planning the 20-30 years they'll spend in retirement. The result? A financially secure retirement that feels emotionally bankrupt, or worse, a retirement cut short by poor planning decisions made decades earlier.

The 4 regrets that haunt retirees:

• Waiting too long to retire: The most common regret involves people who worked hard, saved diligently, and finally reached retirement—only to fall ill or pass away soon after. The advisor shares heart-breaking stories of clients who delayed gratification for so long that they never got to enjoy the fruits of their labour. Sometimes "just one more year" becomes one year too many.

• Not spending more earlier in life: Inspired by the book "Die With Zero," many retirees realize they were too conservative with their money during their working years. One client's aunt died at 72 with a list of unfulfilled dreams—a train trip through New England, a sunroom overlooking her garden—because she prioritized caution over joy. Being financially responsible isn't the same as living a full life.

• Not tracking their progress earlier: This regret usually surfaces as "Did I save enough?" When people don't monitor their financial progress over time, they either over-save and miss opportunities for joy, or under-save and enter retirement with anxiety and limited flexibility. Both outcomes are preventable with regular check-ins and course corrections.

• Lack of tax diversification: The tactical regret that costs real money—having too much retirement savings in pre-tax accounts like traditional IRAs and 401(k)s. When every withdrawal becomes a taxable event, that $5,000 car repair suddenly costs $7,000 after taxes. One client with 100% pre-tax savings had to withdraw 30-40% more than expected for every expense, making retirement feel tighter than necessary.

Actionable takeaways:

• Set a retirement date and stick to it: Don't fall into the "just one more year" trap—your health and energy are finite resources that can't be replaced by extra savings. Consider what you want to accomplish in retirement and work backward from there.

• Create a "joy budget" during your working years: Allocate money for experiences, travel, and dreams while you're still earning. The goal isn't to spend recklessly, but to balance future security with present fulfilment—you can't take it with you, but you also can't enjoy it if you're not here.

• Schedule annual financial check-ins: Track your progress toward retirement goals and adjust course as needed. This prevents both the anxiety of under-saving and the regret of over-saving at the expense of living fully.

• Diversify your tax strategy early: Mix pre-tax savings (traditional 401k/IRA) with after-tax savings (Roth accounts) and taxable investments. This gives you flexibility in retirement to manage your tax burden and avoid the shock of having every dollar withdrawal trigger a tax bill.

• Define your retirement bucket list now: Don't wait until retirement to figure out what you want to do—start planning experiences, relationships, and goals while you have time to prepare and budget for them properly.

Your Turn: Which of these regrets hits closest to home for you? Are you the type who's so focused on saving for tomorrow that you're forgetting to live today, or maybe you're realizing you haven't been tracking your progress as closely as you should? Drop a comment below and share which regret you're most determined to avoid—sometimes admitting our blind spots is the first step to fixing them before it's too late!