Carl's Top 6 NOT Retirement Tips
Carl Landau | February 13, 2025
1. **Retire earlier than you think you should.**
I've interviewed over 90 guests on "I Used to be Somebody" and almost all say they wished they had ended their careers earlier. This includes me. Honestly, think about your Sunday nights or Monday mornings. Do you have the same enthusiasm to get to work that you used to have? My last 3 or 4 years of work, it felt more like a grind, but I ignored it. I wish I had listened to my "Monday gut" and I would have created an exit strategy earlier.
2. **Stop calling it retirement!**
I hate that "R" word. To me that means "You're done, you have nothing else relevant to contribute to the world." Which is why I call the phase after your primary career (un)retirement. It's a time of brand new possibility and personal reinvention! It's a time to explore new interests and fulfill new dreams.
3. **Figure out the money thing.**
Figuring out if you have enough money to stop working full- time is pretty important. I talked to my financial advisor 5 years in advance. Don't be afraid to start figuring out your new life ahead of time. And although I know you're super-smart and everything, hire a certified pro. Plus, you can go into most financial planners and get an initial financial evaluation for free.
4. **Think about your future.**
If you retire in your 60's and you're in reasonable health, chances are you're going to live for decades more. Give some deep thought in ADVANCE about what you want to do next. Most people spend more time planning a 10-day vacation than how they want to live for the next 20+ years.
5. **Don't jump off a cliff.**
One of the worst things you can do is have this hard-driving career for 25++ years and then just stop one day into the retirement abyss, telling yourself you'll be able to figure it all out when you have more time. DISASTER ALERT! It truly takes some serious commitment to figure out who you are outside of your career. But you're worth it!
6. **Try the gentle slope idea.**
If you're in the corporate world, maybe discuss with management about working into a part-time or consulting position. If you're an entrepreneur, go ahead and start off-loading responsibilities to staff. Or hire a consultant to figure out what part of your operation is more profitable and get rid of the part of the company that isn't successful. Do more mentoring and less "working."
I know my tips probably seem like added work when you're contemplating retirement. It's a big decision to end a career you've had for a long time. It might even feel kinda scary. But these tips are inspired by my discussions with over 90 successful people who have taken the time to do (un)retirement right!
Kerry Hannon Interview: The Power of Curiosity!
Diana Landau | May 25, 2021
Carl interviewed author, speaker, radio & TV commentator Kerry Hannon this week. In addition to writing 14 best-selling books, Kerry is a nationally recognized expert, spokesperson and strategist on career transitions, personal finance and retirement. She has covered all aspects of careers, business and personal finance as a columnist, editor and writer for The New York Times, Forbes, Money, U.S. News & World Report and USA today, as well as appearances on Dr. Phil, all the major networks, including CNBC, NPR and PBS. Kerry’s latest book is “Great Pajama Jobs.” We think the best way to describe Kerry is probably “prolific dynamo.”
Kerry grew up in Pittsburgh with her parents and three siblings. Her father had an entrepreneurial spirit as a consultant to large corporations to work on efficiency and management training. Dinner conversations were engaging, as her father was always taking on new clients in various businesses with new kinds of challenges. Her mother eventually worked with her father after the kids were raised. This love of meeting new people and taking on new challenges inspired Kerry. She knew at a very young age she wanted to be a writer and wrote her first book at age 12.
Kerry started writing for Duke University while a student there, as well as Pittsburgh Magazine and various horse-related magazines. “I’m a horse freak!” she says. After graduating she wrote for Business Times, Business Week, Advertising Age, even a column about alternative dance. Kerry has always loved diving into new subjects. Her dream job at the time was to write for Forbes, because her father was a devoted subscriber. At 24, she asked for an interview, eventually the job, moved to NYC. “I never looked back,” Kerry adds.
Not just a writer but a passionate spokesperson for people over 50, Kerry has testified before Congress about the importance of older workers. Before she takes on each job, she asks, “Is this something that is going to make a difference in someone’s life? I want to help people!” Kerry currently lives in Washington, D.C. with her husband, a documentary producer and her Labrador Retriever, Zena. She is still horse-crazy.
Kerry’s Tips for Preparing for UnRetirement
Soul search: “Take a couple of years to plan and think about it. I call it an inner MRI,” Kerry says. “Think about what you really want to do. Take baby steps. It (your path) is not necessarily linear, it’s more like a patchwork quilt, with different areas of interest.”
Get lean and mean: “The other piece of this (your unretirement plan) is you might want to work on getting financially fit. Pay down your debt, get control of your spending and credit cards, maybe downsize. Debt is the biggest dream-killer!”
Consider your options: “Then, when you are financially fit, you can do lots of things that are not so dependent on that paycheck. You can take a job that is enjoyable to you, or even start your own business. Working from home is great for older people, because there is little ageism, the focus is on performance.”
Embrace being a beginner: “Let your ego go. You’ve already accomplished a lot. It’s okay to be the person in the corner, not knowing how to do something, asking lots of questions. It’s good for you psyche. Be curious!”.png)
• More information about Kerry Hannon and her books: https://kerryhannon.com/
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.
Retirement as an Escape
Carl Landau | March 16, 2021

My wife and I just watched two thought-provoking movies, back to back.
The first one was Nomadland. After losing everything in the Great Recession, a woman embarks on a journey through the American West, living as a van-dwelling modern-day nomad. She travels the country and still works occasionally, meeting all kinds of people on her journey.
The second movie was Some Kind of Heaven, a documentary. It follows the lives (and challenges) of four people who live in The Villages, a mega-senior, Disney-esque community in Florida, home to approximately 140,000 people—seniors only!
These two movies were strangely similar in the fact that there are some people of (un)retirement age who just want to escape. To me personally, that doesn’t sound so great. But both movies stayed with me and made me think.
Nomadland showed (un)retired people who were often triggered by something in their lives, usually a trauma, to move on while shunning mainstream life. Some Kind of Heaven is just that—a place where seniors from all over the country come to live out their dream retirement. But is it?
My first reaction was to be judgmental. But if something terrible or unexpected thing happened to me, who knows what choices I would make? If I lived somewhere I didn't like or had few relatives or friends, maybe I would want to live out the stage of my life in an entirely different way. Who knows?
What I've learned from talking with our podcast guests is that you can’t look down on others who don't make the same choices you do. As Episode #21’s guest Ed Casey says, “(Un)retirement is like a fingerprint. Everyone is different.” I can’t think of a better way to make the case that we all need to enjoy life right where are, right now.
Mike Drak Interview: How to Have a Fun, Exciting, Meaningful, Never-Boring (Un) Retirement!
Diana Landau | March 02, 2021

Carl’s guest this week is Mike Drak, author of a new book, Retirement Heaven or Hell: 9 Principles for Designing Your Ideal Post-Career Lifestyle. Mike writes from personal experience, including an abrupt retirement, his struggle and adjustment, and then how he went on to design the (un)retirement of his dreams. His book is honest, funny and heartfelt. The book also details steps YOU can take to determine your next steps. Each chapter asks reflective questions and encourages you to dive deeper into knowing what you want in this stage of life. Most of all, he encourages everyone with helpful advice on how to live your 55+ best life.
Mike grew up in Toronto and still lives there today. He had been working in commercial banking for 36 years, starting right out of college. What he found rewarding about his career was working with start-up businesses. Many were small family businesses (and multi-generational). He truly enjoyed helping people and still does.
SO after 30+ years as a banker, Mike began to think about doing something else. But nothing could have prepared him for the way he found out he was leaving. He was called upstairs to go over projections, yet a young woman from HR was there with severance papers. Adding insult to injury, the bank asked him to say he was “retiring,” and then to save money, actually combined going-away parties with other employees. “I felt like I was going to my own funeral,” Mike said.
He struggled, not knowing what to do at first. “I decided to write the book because I knew a lot of people were going to struggle like I did when transitioning to retirement. I knew a lot of people didn't have a handle on what real retirement is and what it feels like.” Waking up at 4:30am every day to write, he grew very excited about the project. (And he also happened to develop daily writing practice.) His editor noted that he started out to write a retirement book and ended up writing a book about (un)retirement!
Today Mike is a 38-eight-year veteran of the financial services industry, working with his wife and still living in Toronto. He is also the bestselling author of Victory Lap Retirement, an award-winning blogger, public speaker and retirement lifestyle designer. His personal goals include training for a 2024 Iron Man triathlon and visiting his son in Australia, where they plan to face their fears and get in a cage with a Great White shark!
Mike’s “9 Principles” from his book offer great (un)retirement advice, but here’s the key: “You need something to retire to—don’t waste valuable (un)retirement time planning what to do. Do it now!”.png)
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.
The Light Switch Goes off for My (Un)Retirement
Carl Landau | March 02, 2021

I didn't consciously do this, but some sort of "light switch" in my (un)retirement life went off recently. When I put together my Google calendar for this week, I automatically put in my 3 pickleball times/days first. This is an interesting shift. Previously, I would always put in all my work related priorities first and then fill in the rest.
This probably seems like a small change. But as I think about it, I realize that it's somewhat significant. Why? Because my last day of "a real job" was March 2020 and I've been in transition for almost a year into what we like to call (un)retirement. I'm not 100% sure why this calendar transition took place. Could it be the influence of listening to great life advice from the 20+ guests I've had on "I Used to be Somebody"? Or maybe I am finding a better balance between work and play. Either way, it feels great!