What are the biggest retirement regrets people have?

I've sat across the table from people in their 80s and 90s. This is what I hear.

**Regret #1: Not giving and spending for joy** This one I want to shake people about. There is virtually no one who reaches 97 with $2 million in investments who wouldn't give every penny to go back in time and take their 4-year-old grandson to the beach for a day.

So many people are fearful of running out of money, or they're just wired to be frugal, that they don't spend on things that bring joy. It could be charity, it could be family, it could be experiences for yourself. If the math supports that you can do it, why not?

The most enjoyable part of my job is convincing people they CAN rent the giant beach house and pay for the whole family to come. That's what money is FOR.

**Regret #2: Missing the tax timing window** From about age 55 to 75, you have more control over tax timing than at any other point in your life. There are so many levers to pull—Roth conversions, Social Security timing, capital gains harvesting, Medicare premium thresholds.

The difference between paying attention and not? Literally hundreds of thousands of dollars over a lifetime. That's money you're just tipping the IRS because you weren't paying attention.

**Regret #3: Retiring without a vision** Retirement happens by default and you're not running TO anything. You finish the honey-do list, watch some football, take a nap. You're not running toward anything. And when that happens, people get old in a hurry.

You can't run away from things in life. You have to run toward things. Know what that is before you retire.