I Used to Be Somebody: (Un)Retirement Lessons Learned

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Wayne Schmidt Interview: A Traveling (Un)Retirement Adventure 92 Countries and Counting!

Diana Landau | May 13, 2025

Episode 94: Wayne Schmidt​​​​​​​"Digital Nomad" Wayne Schmidt pauses long enough for Carl to interview him in this episode. Wayne and his wife, Sally, decided to resign from their jobs in 2017 and began a new lifestyle by traveling the world. So far, they've been to 92 countries! Wayne, a former corporate exec and entrepreneur, has crafted a business that lets him and Sally wander the globe and live their travel dreams.

Wayne grew up in a small town in Australia. "I was a good country boy," he tells us. In high school, he taught himself computer programming. A teacher noticed and even though Wayne's family was poor and he wasn't planning on college, the teacher enrolled him and secured a scholarship. "Thanks to my teacher, he changed my entire life."

After college, Wayne worked as a corporate exec in the accounting and insurance industries as well as founding his own computer start-up company. After 18 years as an entrepreneur, he went back to working in corporate. At the end of 2017, he and his wife were on a long vacation and he started thinking he wanted to keep on traveling. He and Sally talked it over, resigned from their jobs and sold the majority of their assets (including their home and cars) in 3 weeks. They began 2018 "....with no plans, no direction, no jobs--absolutely nothing!"

Wayne says he's made every mistake possible but has no regrets. "There's nothing I haven't done wrong in 8 years!" But he also emphasizes that people in their 50's and 60's have the net worth to travel. He acknowledges that since his parents have passed away and they have no children, that frees them up in a big way. He adds that the traveling life has really improved their marriage and they couldn't be happier. "We have a greater tolerance for other cultures, we have a much slower pace of life and we have become much less focused on a life of consumption and more on giving."

Wayne and Sally call Belgrade, Serbia their homebase now. They say the people are wonderful, it's very affordable and centrally located. "We can fly to Vienna in an hour and have lunch!" They have a website, Travel.Dine.Stay to share what they've learned and he now works about 2.5 days per week providing marketing consulting for accounting firms. Wayne says, "I call it a leap of faith. Be prepared to fall over. It's alright!"

Wayne's (un)retirement tips:
  • "Don't plan. The more you plan, you set yourself for failure. Go with the flow. I'm a much nicer person than I was eight years ago."
  • "I am not rushing to my grave. We want to go slow. Give me a three-hour meal any day!"
  • "Avoid the mainstream media's "top 10" lists of places to visit. Personally, we love a language barrier."
  • "Get a financial planner and be prepared to take some risks, even doing something unusual."
Check out more super fun unretirement ideas - Click here for this week's newsletter!​​​​​​​
• More about Wayne and Sally Schmidt​​​​​​​
• Forbes Article about The Schmidts
• Sponsored by: How to Retire and Not Die
• Sponsored by: Capital Advantage
• I Used to be Somebody World Tour
• Subscribe to the I Used to be Somebody newsletter​​​​​​​

 

Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody" blog

 

Tags:    blog   unretirement   travel   financial planner   founder   consultant   vacation  

Practice Makes Perfect, Or How to Plan a Mini-Retirement

Diana Landau | August 31, 2020

Planning on retiring soon? Then you already know there’s a ton of information out there for soon-to-be-retirees. “Get your health insurance squared away, have savings for emergencies, more health and financial stuff, blah blah, blah.”

We are going to assume that you’ve already got these important topics under control. But have you thought about scheduling a “mini-retirement” before that big “last day” arrives?

A mini-retirement is a scheduled and budgeted time away from work that is different than a vacation or a sabbatical. You try out what your life will look like when you don’t ever go back to that career. (We’ll be honest:it takes a little work not to work!)

 

5 Tips to Planning a Successful Mini-Retirement

 

How long feels right to you? 

Schedule a block of time and make sure it’s long enough. Is six months possible?

How much to spend?

Budget for this time differently. Vision what your lifestyle will be without all the work perks and paychecks. (And we’re not talking about going without an abundance of office supplies.) 

Manage the worry factor.

This is a big one: Don’t assume your mini-retirement means you are going to be worrying about your finite bank account all the time. Figure out a way to emotionally grasp this now so you don’t dampen your joy post-retirement.

Think and think some more.

Plan your time during this period and keep a journal. This is a time is for social activities and health, but also reflection.. What do you want your life to look like in your Second Act?

Consider the possibility you won’t return to work after all. 

After months away from work and plenty of rest, you may end up wanting different things now. Maybe you’ve tapped into creativity you never knew you had. Or settled on your post-retirement career or project.

There is no one right way to plan for a mini- (or real) retirement. Only you can figure out what works best for you. But try it! This little checklist can help get you started. And what’s better than making you the priority? 

 

Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the I Used to Be Somebody weekly blog. 

Tags:    blog   retirement   vacation   mini-retirement   work   budget