The 3 Biggest Retirement Regrets I Hear From 75-Year-Olds

I’ve had thousands of conversations with retirees over the years. And when I look back on those conversations, the same regrets tend to show up again and again.

Some of them are financial. Some of them aren’t.

But what’s interesting is that these regrets usually don’t come from catastrophic mistakes. Most of the people I talk to were responsible. They saved diligently. They worked hard. They did many things right.

The regrets come from smaller decisions that compounded over time. Or from habits of thinking that stole peace and enjoyment from years they can never get back.

And if you’re in your late 50s or early 60s, the good news is that you still have time to avoid them.

Here are the three biggest retirement regrets I hear most often from people in their mid-70s.

1. “I Wish I Had Taken Tax Planning More Seriously”

This is probably the most common financial regret I hear.

Many retirees spent decades focused almost entirely on growing their investment portfolio. They paid attention to returns, allocation, and performance. But taxes were often treated as something to deal with later.

Unfortunately, “later” eventually arrives.

By the time many retirees reach their 70s, Required Minimum Distributions (RMDs) begin forcing money out of traditional retirement accounts whether they need the income or not. Those withdrawals can push income significantly higher and create a chain reaction of unintended consequences.

More of their Social Security becomes taxable.

Their Medicare premiums increase because of IRMAA surcharges.

Capital gains become more expensive.

And suddenly they find themselves paying far more in taxes than they ever expected.

What makes this especially frustrating is that many of these problems could have been reduced with proactive planning earlier in retirement.

The challenge is that 10 or 20 years ago, most financial planning wasn’t built this way. Advisors often focused primarily on investments. If taxes came up, the response was usually:

“We don’t give tax advice. Talk to your CPA.”

But many CPAs are focused on tax preparation, not long-term tax strategy. They’re looking backward at what already happened rather than helping retirees make decisions that improve future outcomes.

That’s changed quite a bit today. Good retirement planning now includes tax strategy as a core component. Roth conversions, withdrawal sequencing, charitable giving strategies, and managing income brackets have become essential parts of the process.

Still, many retirees in their 70s tell me the same thing:

“I wish I would have taken taxes more seriously when I actually had the chance to do something about it.”

The reality is that your late 50s and early 60s are often some of the best years for proactive tax planning. Once RMDs and Social Security fully kick in, flexibility starts disappearing.

2. “I Should Have Done More While I Still Could”

This second regret is almost the opposite of the first.

A lot of retirees were so focused on being responsible that they forgot to enjoy the early years of retirement.

I hear this one constantly.

People delayed trips they wanted to take. They postponed experiences with family. They avoided spending money on things that would have genuinely enriched their lives because they were afraid of running out of money later.

Many of them spent the first decade of retirement in “wait-and-see” mode.

Part of that fear came from hearing horror stories about retirees who ran out of money and had to go back to work. So even people with substantial savings often became extremely cautious.

The problem is that retirement changes over time.

Health changes.

Energy changes.

Priorities change.

People you love pass away.

There’s a reason many planners refer to the early years of retirement as the “go-go years.” These are often the healthiest and most active years retirees will have.

But many people never fully embrace them because fear keeps them stuck in preservation mode.

Then later, when they finally feel financially comfortable enough to spend more freely, life looks different.

One retiree once told me: “We finally realized we could afford the trips we wanted to take… right around the time we no longer wanted to take them.”

That’s a painful realization.

Now, this doesn’t mean retirees should spend recklessly or ignore financial risks. The solution isn’t blind optimism.

The solution is confidence.

You need a retirement plan that’s clear enough and stress-tested enough that you’re not second-guessing every spending decision at two in the morning.

Because when people truly trust their plan, they usually enjoy retirement far more.

And frankly, that’s the entire point.

3. “I Spent Too Much Time Worrying About Things I Couldn’t Control”

This third regret isn’t really about money at all.

It’s about anxiety.

Not just financial anxiety, but the constant habit of worrying about every possible outcome.

I work with a lot of analytical people. Engineers. IT professionals. Problem-solvers. People who spent decades thinking ahead, managing risk, and being responsible for outcomes.

That mindset is often a big part of why they became successful in the first place.

But it also creates a trap.

Analytical minds don’t like uncertainty. They want to think through every scenario and prepare for every possibility. Over time, many people begin believing that if they plan carefully enough, they can control what comes next.

But retirement doesn’t work that way.

Life doesn’t work that way.

And eventually that mindset starts creating constant mental noise.

People worry about the market.

Their health.

Their spouse.

Their children.

Politics.

Taxes.

The economy.

They connect dots endlessly and run worst-case scenarios in their heads over and over again.

But when I talk to retirees in their mid-70s, I hear the same realization repeatedly:

Most of what they worried about never actually happened.

Now, to be fair, some difficult things did happen. Retirement is never perfect. Life still includes loss, setbacks, uncertainty, and change.

But retirees often tell me the things that actually happened were rarely the same things they spent years worrying about.

And many regret how much emotional energy they gave to fears that never materialized.

They regret the joy it stole from time with family.

They regret how much of life they experienced through a lens of anxiety instead of presence.

After listening to these conversations for years, one thing has become very clear to me:

The retirees with the most peace are usually not the ones trying to control every possible outcome.

They’re the ones who learned to focus on what they can control and make peace with what they can’t.

The Common Thread Behind These Regrets

When you step back and look at all three of these regrets together, the common thread becomes pretty obvious.

The biggest regrets in retirement usually aren’t catastrophic financial failures.

They’re things like:

• Not planning for taxes when you still had flexibility
• Waiting too long to enjoy the healthiest years of retirement
• Carrying the emotional weight of problems you could never fully control in the first place

And if you’re in your late 50s or early 60s, you still have time to make different decisions.

You still have time to build a retirement plan you actually trust.

You still have time to give yourself permission to enjoy life without constantly second-guessing every decision.

And you still have time to let go of worries that don’t deserve as much space in your life as they’ve been taking.

Because the goal isn’t just to retire with enough money.

It’s to get to 75 without carrying these same regrets with you.