This month Carl chats with Jed Smith, a former top marketing exec who worked with brands all over the country, including Athleta, where he was the Senior Creative Director, before making his next big move 10 years ago--to Italy. Jed has embraced (un)retirement as a very accomplished artist and photographer. He is also the author of the recently released book "Under the Oak with Agnes." 

Jed spent his growing up years in Columbia, South Carolina. His father was a nuclear engineer and his mother was an artist and art teacher. "She really brought out my love of art and expression......I am so grateful for that."  As a teen in Clemson, Jed says he didn't feel confident then and wasn't sure about his place in the world. Everything came together for him in college when he entered University of Georgia's School of Graphic Design.

Jed studied art abroad during college in Cortona, Italy. "I wasn't prepared for how it blew me away!" Living in Italy ignited a hunger in him to one day live in a different country and culture. Through his career, Jed lived in 15 U.S. states. (He adds that his mother always said he was restless.)  Years ago, Jed was working on a photo shoot in Italy for Athleta and stayed longer for vacation. Soon he was touring properties with a real estate agent. He'd just sold his home in San Francisco and he decided to buy a home in Italy. 

Jed has embraced his (un)retirement life in Italy. In addition to becoming an author, Jed blogs regularly on his Italywise.com about making the transition to living in a new country and wants to help others with adapting to a new culture and language. He also recently launched a new standalone website, Jedsmithart.com for his incredible paintings and photography. "Wake up every day and remember that your ability to create is without limit," he says.

Now 67 and living on the Italian coast, Jed is on the move again--this time to Ragusa, Sicily. "With everything I've learned, it's important to surrender. Show up, do your best, tell the truth and then let go of the outcome!" 

Jed Smith's tips on making the leap to a new country and culture:

• "Americans don't often understand the flipside of immigration. You can't just waltz into another country. Research and plan as you begin to navigate the process."

• "Be careful how you balance the romantic side of your dream with the practical realities."

• "Without a command of the language, your experience will be so limited."

• "My pet peeve: Don't try to pack up your culture and move, only leaning into what's familiar."

• "If you're not feeling a little nervous, you're not taking the committed leap! Demonstrate to the universe that you are serious about the step you're taking."

• More about Jed Smith

• Sponsored by Capital Advantage

• Sponsored by Mike Ownbey, COMPASS 

• Sponsored by How to Retire and Not Die

• I Used to be Somebody World Tour: First Stop -- Tuscany

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   Carl Landau   Jed Smith   Artist   Unretirement   I Used To Be Somebody   Italy   Marketing   Executive   passion  

This week Carl interviews Steve Segner, a man of boundless energy. At 74, he's a long-time entrepreneur with no plans of slowing down. "I have no intention to retire!" Steve says--and we believe him. He has successfully run a newspaper distributorship, owned pet stores, developed lines of all-natural dog food, other related businesses and an amazing hotel and so much more.

Steve grew up in Burbank, CA in a neighborhood of blue-collar families right across the street from Lockheed and Disney Studios. He says the area was almost rural back then. From an early age, Steve remembers being fascinated by his parents' friends' stories, who were inventors and people who created things. "I just wanted to run a business," he tells us. "I thought I'd be good at it. I wasn't good in school--they didn't know what to do with dyslexic kids in those days."

Right out of high school he worked for a brokerage firm that suddenly closed. He decided right then he would never work for anyone else again. At age 21, he charted a course to become a life-long entrepreneur. He took a job as an independent distributor of the Pasadena-Star News, where he eventually met his wife, Connie.

Always eager to jump at a new opportunity, two days after they got married Steve decided to buy a nearby pet store. "How hard could it be?' he thought. He and Connie always had a strong work ethic, working at the newspaper in the early morning and then at the pet store until the evening.

Along the way, Steve and Connie developed an all-natural, healthy pet food line, a delivery service, a birdcage company and bought more small pet stores. Then Steve got involved in the World Wide Pet Supply Organization and as their Board President convinced them to relocate and expand their annual trade show to Las Vegas, NV. "Super Zoo" is now America's largest marketplace for the pet industry.

FUN FACTS: You'll have to listen to the podcast to hear the story about natural dog food, actor Abe Vigoda (of Barney Miller and The Godfather fame), NBC's Today Show and the advertising that went viral before things "went viral."

After years in the pet biz, Steve started thinking about doing something new--again. He wrote down goals for himself, including starting a completely new business by age 55. He wanted to learn something entirely new, something different, something more meaningful. (It turns out Steve is living proof of what we always talk about on the podcast.)

Steve knew he loved retail and they had purchased a vacant lot in Sedona. He set out to build an Arts & Crafts, hacienda-style adobe hotel. The El Portal, a gorgeous Sedona Inn, became the new vision. Steve worked with the architects and designers to build an adobe inn in 2003 that looks like it was built around 1900. Guests from all over the world have stayed at El Portal, including Supreme Court Justices, actors and record producers.

Steve's next act was to build a "Greene and Greene" style Pasadena Estate and a new high-rise condo in Scottsdale with curved glass walls circa 1960's. Their homes and inn have been featured in architectural style magazines. In addition to running El Portal, Steve loves developing new projects, working with local government, mentoring, speaking, still passionate about his pets and gardening. "I always want to be curious and excited about new projects and opportunities!"

Steve Segner's entrepreneurial life tips:

• "Sometimes it is OK to stay in your lane, what you're good at. And it's OK to fail--just try to fail small."

• "You are always missing opportunities, so you always have to be actively looking for them."

• "Moving forward into unknown territory is where the path to success lies."

• More about Steve Segner

• Sponsored by Mike Ownbey, COMPASS

• Sponsored by How to Retire and Not Die

• Sponsored by Capital Advantage

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   steve segner   unretirement   pet   business   executive   luxury   hotel   pickleball  

Carl interviews one of the Founding Fathers of the (Un)Retirement Movement, Richard Eisenberg. Rich spent 40+ years as a personal finance reporter, editor, writer, producer and popular podcast host. He worked with organizations such as Money Magazine, People, Good Housekeeping, Yahoo, CBS Money Watch and most recently with PBS's Next Avenue. Rich just "unretired" in January 2022, and shares some lessons learned about having a second act.


Rich grew up in the New Jersey suburbs. He was always a curious, studious kid, he says. He became editor of his high school newspaper and also worked at the school's radio station. After graduating from Northwestern, he pursued his passion for journalism. "One of the reasons I wanted to be in journalism was because I wanted to be helpful and useful to people in some way." Also interested in pop culture, Rich's first job out of college was as a fact checker for People magazine. Rich's career took him from that position, to becoming a reporter, Senior Editor, then Washington correspondent and Executive Editor for Money Magazine and others.


During his career, he worked remotely and was an early adopter for working with people all over the country, from his home office. "I didn't have any problem with it," he tells us. Now, Rich is still writing a column and hosting a podcast, writing book reviews for People, plus volunteering and pursuing other opportunities such as getting involved in a NYU student program on digital media and book publishing. Carl asks Rich what he's learned in the last 9 months. "I'm still writing, but trying some new things and liking the mix of the two. So far, so good!"

Richard Eisenberg's (Un)Retirement Advice:

•  "Until you're actually in it, (unretirement) you can't know exactly how it will be. Maybe the scariest part will be having a blank calendar with nothing filled in on it. So you'll need to figure out how much you want to fill it up. Some people will want to have stuff every day. Some people may want lots of free days. You have to spend some time thinking about how you want to spend your time."

• "Don't be scared-- realize you are going to make some mistakes. There's really no right way to do it."

•  On becoming too busy: "Saying 'No' to opportunities can make you feel uncomfortable sometimes. There's an adjustment period."

•  "People need to be able to find meaning and purpose in their lives--whether it's part-time work, or volunteering, or spirituality, but they have to have a reason to get up in the morning. Sometimes they're following a passion, or seeing a need, and then finding a way to serve that."

• More about Richard Eisenberg

• Sponsored by: Capital Advantage

• Sponsored by: How to Retire and Not Die

• Sponsor by: The Monkey Creative

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   interview   unretirement   Richard Eisenberg   journalism   executive editor   People Magazine   PBS   Money magazine  

Carl talks with Paul Ollinger, an author, stand-up comedian and host of the Crazy Money podcast. He also has an MBA from Dartmouth’s Tuck School and was one of the first 250 employees of Facebook, where he served as VP of West Coast Sales. You could say Paul is on his third successful career at this point.

Paul grew up in a suburb of Atlanta, one of six kids from a big Catholic family. His father was an engineer for a Georgia utility company and although there was money, his parents were frugal and there was a strict budget. Paul felt that anxiety about money as a kid and as his careers at Facebook and in comedy rewarded him, he realized that no matter how much money you make, you can still feel stressed about it. His podcast, Crazy Money is not about how to make more money but about exploring the connection between money, happiness, work and meaning.

Paul’s path to success has been anything but linear. After college and a focus on business, Paul made his first attempt to become a stand-up comedian and became a host at LA comedy clubs, opening for many big names at the time. Then he got married and started thinking about a more stable career for raising a family. A friend asked him if he wanted to be part of this new social media start-up company—he became the 250th employee at Facebook.

After relocations to other cities and promotions, in 2012 Paul left his very financially secure job and decided to put down roots for his young family. Atlanta was home. For the first few years, Paul wasn’t sure what to do. “I didn’t go toward anything after I quit my job.” He then worked for a year but knew it wasn’t the right fit. He decided to face his real fear—would he fail if he went back to comedy? He started writing every day, got himself into the comedy scenes in various cities and committed to his new path.

Carl agreed that forging an entirely new career is scary—but it’s invigorating! Paul noted that the nervousness means you really care about what you’re doing because you want to figure it out. “Breaking ourselves out of the mode by which we’ve been measuring ourselves for past decades is highly disconcerting, but it’s what you need to do to find a new path in the post-corporate world.” Now in 2021, Paul has a very successful career as a stand-up comedian, author and speaker, and is also busy hosting his podcast. From a young age, Paul has been driven to push himself to new heights. “I just want to get so much better at everything I do!”

(Un)retirement advice from Paul Ollinger:

• “Change your metrics! The way you’ve been evaluating your life in the work world will be very different afterwards. And if you’re looking for external validation like bonuses and titles and being known in the industry, that goes away…..YOU have to be the one to monitor your own progress.”

• “We need to have a longer term ‘through line’ in our lives. That’s where the meaning lives. The sooner you can get on it and it feels authentic to you, the sooner you’ll get to this is me, this is my life.”

• “Let go of worrying about anyone else. You are doing (this new path) for you. The world may not notice. Do it because it’s an expression of who you are without any external reward.”

• More about Paul Ollinger and his podcast Crazy Money: https://paulollinger.com/about/

• Sponsored by: lovemyheartstudy.com or call (866) 955-1594

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   facebook   executive   unretirement   comedy   paul ollinger   crazy money   dartmouth   career  

This week Carl interviews Andy Robin, former President and CEO of Ascenium, who has written a unique post-retirement book, Tapas Life. After his many accomplishments as an executive in the high-tech corporate world and raising a family, Andy has learned a lot. He wrote the book to share what he’s learned, including some missteps along the way, and as he says, “I want to help people get on the path to the life they want sooner.”

As a child, Andy’s family moved from Chicago to Mexico City, his father was in the computer business. He says it gave him a different cultural perspective. Andy dropped out of college after one year and went to work with his father. Knowing then what he truly wanted, he went back to college, eventually earning his MBA.

Andy and his wife were working their way up the corporate ladder when they made a life-changing decision: They would always put family first, and they would share the raising of their children. So, Andy kept his job but did not work more than 45 hours a week so he could be home for dinner. His wife earned her PhD and when the children were teens, she re-launched her career and Andy traded in overseeinghis hi tech exec job to become a house dad.
“It was trial by baptism!” Andy added.

Another unique decision was when Andy and his wife recognized they were financially comfortable, so they decided to freeze their standard of life vs continuing to strive for more promotions and longer hours. It was another life decision guided by determining their own quality of life.

Andy found the teen years very rewarding and then the kids went to college. “I felt adrift,” Andy tells us. After some trial and error, he wanted to share with others what he learned about charting a rich and rewarding life in unretirement. His book is different from the others in that he urges people to find their “Tapas Life.” Often people think, “This is my retirement life, I’ll just add a sport or hobby to it to keep myself busy.” The “Tapas Life” is so much more than that. It’s about creating a path for your new stage of life by exploring all the wonderful options out there. As for Andy--he is now an author, speaker and life coach, enjoying his Tapas Life to the fullest.

Andy’s advice on living life to the fullest:

• “Don’t talk yourself out of trying anything and everything. That’s leaving so much on the table.”

• “Pay attention to how you eat and exercise. The object of the game is quality of life. Take care of yourself!”

• “Have a meaningful conversation with your spouse specifically about what your lives will look like going forward. What do we still have in common? Are there things we both enjoy that we could do together? Should we explore some things we have never tried?” (Andy’s book has great suggestions for this.)

• More about Andy Robin's "The Tapas Life:" https://www.tapaslife.com/

• Sponsored by: lovemyheartstudy.com or call (866) 955-1594

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   andy robin   the tapas life   ascenium   interview   executive