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

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Paul Ollinger Interview: Former Facebook Exec Turn Comedian -- “Now I’m Me!”

Diana Landau | October 05, 2021

 
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  

Jack Gallagher Interview: Take a Chance!

Diana Landau | May 11, 2021

Episode 29 Jack Gallagher - Comedian, Writer, Musician, TV Host and Larry David's Doctor!Carl talks with Jack Gallagher, a comedian, actor, and writer, and Emmy award- winning television host of the PBS series Money Moves (nationally syndicated), Off-Limits, and Kids, Cash and Common Sense. He was also the host of California's The Big Spin Game Show and had a recurring role as a doctor on the hit HBO sitcom Curb Your Enthusiasm.
 
But there’s more! Jack is also the author and performer of eight critically acclaimed one-man shows. We’ve seen most of these highly personal, very relatable shows that make you laugh, cry and laugh again. His shows stay with you. So what’s Jack doing now? He’s still working and loving it, but also trying to take it easy. “I’m not chasing it anymore, but if someone calls, I’ll consider it.” (Of course, they still do.)
 
Jack grew up in a hard-working Irish Catholic family with 5 kids in the small town of West Bridgewater near Boston, MA. Jack says he was a shy kid growing up. (Most comedians are actually introverts.) By the age of 10, Jack knew he wanted to be a comedian, to make people laugh. “It took me out of my shell,” he says. His conservative parents were not so sure at first but eventually they came around.
 
After working towards a teaching degree, Jack took a chance and started performing at a Comedy Night on Campus, then in the Boston comedy scene just as it started to take off. Boston became a hotbed of comedy “greats.” It all happened pretty fast. Signed by an agent, Jack moved to LA and became a regular at the Improv. “Hecklers make you battle-tested,” Jack laughs. Then came the big break—an appearance on the Johnny Carson show. Performances followed.
 
In 1987 he was hired by KCRA in Sacramento to do a show. After being on the road for 15 years, Jack and his wife decided to stay, raise a family. He would fly down to LA and do his shows and then come back to Sac. He also had the opportunity to perform on Larry David’s Curb Your Enthusiasm. “It was a lot of ad lib—which is fun!” Always writing, Jack created eight one-man plays. Carl notes the stamina that takes. They require 60 shows in 6 weeks, 1.5 hours a night, 2 hours a night on Saturdays. “The audience rides the rollercoaster with me,” says Jack.
 
So now after a long, successful career, Jack at age 68 is still taking chances, but also taking it easy. He still writes and also performs in a band. Jack and his wife, Jean Ellen are also spending time visiting their sons, traveling when possible and every year they go to Massachusetts. “I’m really good at what I do. I’ve been incredibly lucky, it’s worked out.”
 
UnRetirement insights from Jack Gallagher:
 
  • “It’s weird to get old. Everything hurts! But I’m still 30-35 in my head. Sometimes I get recognized and sometimes I don’t and that’s okay!”
  • “I always tell my kids, the worst thing that can happen to you is someone says ‘No’. Just try something, take a chance!”
Check Out More Super Fun Untretirement Tips
  • “I still like what I do, I still love performing. (But now) I try to do stuff that’s just fun!”

 

For More Information about Jack Gallagher: https://en.wikipedia.org/wiki/Jack_Gallagher_(comedian)
 

 

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   interview   Jack Gallagher   author   performer   risktaker   comedy   unretirement   Larry David   improv  

Caroline Ceniza-Levine Interview: Do What You Love to Do! (And Quit What You Don't)

Diana Landau | March 30, 2021
 
 
This week’s guest is Caroline Ceniza-Levine. Caroline is a dynamo in every sense. She has been a career coach for Amazon, Condé Nast, Goldman Sachs, Google, Tesla and other start-ups through global economies. Her specialty is career change, and she is the author of “Jump Ship: 10 Steps to Starting a New Career."
 
But HR is just a fraction of the many things she does well. She’s been a guest expert on CNN, NMC, CBS, FOX and other outlets; she’s also been a Senior Contributor to Forbes and a former career columnist in Money, CNBC and Portfolio. Did we mention she is also a Director for non-profits, an adjunct professor and a very funny stand-up comedian?
 
Although definitely not your average career path, Caroline says she learned the pace and variety from her hard-working single mother. She says that growing up in Lower East Manhattan, her mother always had several side gigs. Caroline went to Barnard College and studied at Julliard as a classical pianist. It was the first time she decided to pivot to something new. “That was a big growth step for me,” she says. “Quitting was a gift to myself.”
 
So Caroline followed her many other interests instead. She was working with large companies and saw very successful, talented, hard-working people who were still not 100% satisfied with their jobs. That’s when she decided to trust her instincts. Her secret? “You have to be prepared to pivot constantly. So I embraced that.”
 
Caroline urges people to find their dream jobs, instead of a haphazard approach to finding that next opportunity. The same could be said of (un)retirement—make a plan:
  • Look for growth opportunities
  • Identify your resources
  • Make the changes you desire
  • Re-brand yourself
  • Build a new community
  • Have confidence
 
During the podcast, Carl tells Caroline how much he admires how fearless she is. Caroline replied, “I’m actually fearful. But you just need to push yourself through it!” Caroline and her husband now split their time between NYC, Jacksonville FL, and Costa Rica. And you guessed it, still following her passions!
 
More insights on (un)retirement from Caroline:
•     "Networking—Go do it! Figure out the methods of networking that work best for you."
•     "It’s so much easier now to make money at things you are interested in. What a great time to have a body of expertise and experience and (you can) carve something new out of that."
•     "Work is play! I now pick my projects based on whether they’re going to be fun and I’m going to enjoy working on them."
 
• For more about Caroline Ceniza-Levine: https://focusisoverrated.com/
 
• This Week's Sponsor is The Monkey Creative: https://themonkeycreative.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.
 
 
Tags:    blog   interview   Caroline Ceniza Levine   pivot   comedy   career   dream job