41 and 35 and wondering if we’re doing the right things to ensure a solid retirement down the road. That’s how we kick off the latest Jill on Money show.

Next up is a caller wondering if they should take advantage of the hot real estate market and sell their rental property and invest the proceeds.

In hour two we welcome Stacey Vanek Smith, NPR host of The Indicator and correspondent for Planet Money, who joined us to discuss her recently released book, Machiavelli for Women: Defend Your Worth, Grow Your Ambition, and Win the Workplace.

Women have been making strides towards equality for decades, or so we’re often told. They’ve been increasingly entering male-dominated areas of the workforce and consistently surpassing their male peers in grades, university attendance, and degrees. They’ve recently stormed the political arena with a vengeance. 

But despite all of this, the payoff is, quite literally. not there: the gender pay gap has held steady at about 20% since 2000. And the number of female CEOs for Fortune 500 companies has actually been declining.

So why, in the age of #MeToo and #TimesUp, is the glass ceiling still holding strong? And how can we shatter it for once and for all? Stacy Vanek Smith’s advice: ask Machiavelli “with this delicious look at what we have to gain by examining our relationship to power.”

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.