A financial life: Meet Jack and Diane


Recently I started watching the Netflix show You vs. Wild with my older kids.

The show follows Bear Grylls in his travels around the world and allows viewers to choose his next move to survive in the wilderness. It’s like a “choose your own adventure” series. (Some of you might remember reading Choose Your Own Adventure books as kids—or reading them to your kids.)

My kids love the idea that they can influence Bear’s actions. So I started thinking about creating a “choose your own adventure” blog series.

Because I’m a Vanguard financial advisor, we’ll go on a financial adventure with Jack and Diane, a hypothetical married couple.

Jack and Diane will come to financial crossroads at different times in their lives. We’ll describe one of these scenarios and ask you to vote in a poll about which action you’d recommend for Jack and Diane. In my next post, I’ll share the poll results and how I’d advise them if they were my actual clients.

Meet Jack and Diane

Jack and Diane are what we in the financial business like to call “mid-career accumulators.” Jack, 47, is a high school math teacher. Diane, 48, is a mechanical engineer for a large company.

Here’s Jack and Diane’s current financial picture:

  • Retirement accounts. They’re each saving 10% of their salaries in their workplace-sponsored retirement accounts. If Jack teaches until he’s age 55, he’ll also get a small pension. They don’t have any IRAs (yet), and they aren’t sure when they’ll file for Social Security benefits.
  • College savings. They have a 529 account for their son, Evan, a high school senior, but it won’t quite cover 4 years’ tuition.
  • Retirement goals. Jack and Diane want to retire in their early- to mid-60s. They also want to purchase a vacation home by a lake, so one day Evan will visit with any potential grandkids.

“Sandwich Generation” dilemma

Jack and Diane have saved consistently, but they’re about to face a common “Sandwich Generation” dilemma. They’re saving for retirement, Evan’s about to go to college, and Diane’s mom needs help paying for her assisted-living facility.

The good news? Jack and Diane both make decent salaries, but the expenses are mounting to support generations above and below them (hence the Sandwich Generation moniker).

What do you think?

That leads us to our first poll question: How should Jack and Diane prioritize their expenses and savings?

Feel free to leave a comment below, especially if you’re familiar with this dilemma.

Read the next post in this series



  • All investing is subject to risk, including the possible loss of the money you invest.
  • Advice services are provided by Vanguard Advisers, Inc., a registered investment advisor, or by Vanguard National Trust Company, a federally chartered, limited-purpose trust company.


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