Debbie speaks with Sean Bailey, founding editor-in-chief of Horsesmouth, a New York-based company that creates educational programs on retirement planning, Social Security, Medicare, college planning, cybersecurity, and more for industry professionals.

The focus of their conversation is financial planning around a gap year. Sean shares some basic practicalities: you have to create a budget, you have to assess your own situation (what money have you saved, can you dip into it now, etc.) and you have to consider the real cost of a gap year. That usually means stepping out of your current life for a period while still covering the costs of that life.

Use a spreadsheet, use a whiteboard, use the back of a napkin, but force yourself to do the calculations.

He talks about a concept he calls “retire at 60, or earlier… work til 70!” By that he means start thinking creatively now about your financial situation. Take advantage of opportunities to explore different kinds of work, different ways of making money and different ways to build flexibility into your life.

In other words, start living your dream even before you retire or consider taking an official gap year.

Sean also talks about his experience of taking a gap two years, almost thirty years ago, to join the Peace Corps. Sean and Debbie share similar values around the idea that we should pursue our dreams now, not later. But with a reasonable amount of planning.

What they talk about:

• MUG: Mortgage, Utilities, Groceries and the importance of considering these things, plus healthcare, when planning a gap year.
• The two different types of money: qualified and unqualified.
• The real cost of a gap year: leaving your default life temporarily while still maintaining it while you’re gone.
• The uncertainty of a gap year even when the finances are all planned out.
• His mantra: “retire at 60, work til you’re 70.” Look for opportunities to take mini “gap” breaks. Going to Arizona for work? Turn it into a seven-day trip to visit the Grand Canyon and hike in Sedona.
• Skilling up: learn new skills in areas you love to supplement your retirement and/or to keep active in a field you’re passionate about.
• The advisability of consulting a financial professional before claiming your social security and/or pulling the trigger on your retirement/gap year.

Mentioned in this episode:

• Sean Bailey bio
• Horsesmouth
• 16 Lifestyle Questions to Ask If You Are Retiring (PDF)
• 5 Questions to Ask 5 Years Before You Retire (PDF)
• FIRE movement (Financial Independence, Retire Early)