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  

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  

Your (Un) Retirement Super Power

Carl Landau | September 22, 2020

When we launched Pickleball Media and started our podcast, I looked at this project in the same way I did in my previous career. In podcasting, like most media businesses, it’s all about how to build an audience. So you do that via email and social media and through providing great content that will attract the right group.

 

It's not easy starting to build an audience from scratch. Without going into the boring details, we took all the right steps. But like anything there are some parts I like to do and... some I don't. Surprisingly, I like building out an audience contact list, talking to sponsors and creating content. And I really like the interviewing part of the podcast. It's the personal contact and interaction with creative types that gives me energy. 

 

But I really don't enjoy the social media part at all. And then it hit me... I don't need to do that. We'll do the basic stuff but I don't want to sweat the details of hardcore, daily social media. I just want to concentrate on what's fun for me. 

 

I guess my point is that I had to give myself permission to just do what I want to do in (un)retirement versus what I needed or had to do in my previous career. Sometimes I think we all get caught up in what we used to do. Now we need to figure out what we want to do!

Tags:    the carl diary   retirement   choices   media   career  

10 Time Hacks for Boomers

Diana Landau | July 27, 2020

In your Second Act, no one manages your time except you! At first, a big, wide-open retirement calendar can be fun. But at some point you realize you really don’t want to waste your time. And we all need a sense of accomplishment, no matter where we’re focusing our energies. It can be easy to get overwhelmed looking at an ever-growing  list of all the things you want (or need) to do. On the other hand, running around with everything in your head slows you way down. 

 

So how do you best manage your days?

 

Desmond Tutu wisely said “There is only one way to eat an elephant: a bite at a time.” Here is a quick list of 10 tips to get you organized to meet your goals. The key here is to better construct your schedule so you can spend the majority of your time as you wish!

 

1. Assign a time limit for each task you want to accomplish. For example, if you want to clean your office, assign 2-hour increments. It’s amazing what you can accomplish if you break it up into manageable segments.

 

2. Itemize the “big ones”. For bigger tasks that may take longer, set up a to-do list tailored specifically to that goal.  Tackling each step gets you closer to that larger accomplishment.

 

3. Don’t abandon tasks. Take your list-crafting seriously and don’t ignore what you’ve written down. Procrastination is one of the biggest time-wasters. Don’t give in to it.

 

4. There’s an app for that. Believe it or not, there are many new apps out there to help with time management. For example, RescueTime helps you understand your time in a way you never have before.

 

5.  Set aside time to plan your attack. The night before, take 15 minutes to plan your day, and include in some down time. It’s important to be realistic. One solution could be to wake up an hour earlier.

 

6. Tackle very important tasks in the morning.  Although there are true night-owl exceptions, many of us have most of our energy in the morning, after a night’s sleep. 

 

7. Consider batching tasks that are similar. You can save time using the same skills for the same sort of to-dos. For example, don’t make one appointment or follow up call, make three. 

 

8. Delegate, outsource, even ask for help. TaskRabbit and Thumbtack are go-to resources when you need help. And although most of us don’t want to bother friends or family, you are missing out on an opportunity to return the favor. That’s what makes the world go-round.

 

9. Limit your time on social media and online surfing. Seriously. Set a timer on your phone and when the timer goes off, get up out of that chair and MOVE.

 

10. Celebrate each completion! Crossing items off your to-do list creates daily optimism and is empowering. Your valuable time is now free for tracking dreams. 

 

Jot it down, get it done and then go have fun!

 

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:    baby boomer   career   top 10 list   time management   time tracking app   task list   retirement     

No One Told Me

Carl Landau | July 15, 2020

1. No one told me that in retirement, no one wants your expertise about that work you did for the last 20+ years. (Not even your spouse. Maybe your dog.)
 

2. No one told me that in retirement, taking a nap isn’t as fun as it used to be. You lay down for a moment (or three) to rest a little…and you’re afraid you might not get up again!
 

3. No one told me that my significant other is so busy. Here I thought they’d drop everything and focus on ME when I retired.
 

4. No one told me that in retirement that I’d get around to that consistent exercise routine and finally get in shape…but I’d have injuries! Pulled muscles! Playing through the aches! I can go on…
 

5. No one told me that I’d have to make new friends at my age. Not so easy! I think it’s harder for guys and more so if you had an all-consuming career.
 

6. No one told me that in retirement, the two most powerful words are YES and NO. Yes, I would like to go to dinner or see that new play! No, I do not want to join your committee with 30 weekly phone calls/emails and 5 meetings each month!
 

7. No one told me that in retirement, people would assume I do nothing all day. Not true! What’s different is now I control what I want to do and when I want to do it.
 

8. No one told me that in retirement, I would actually want to work, but just in a different way.  (Less grind, more fun!)  In fact, 3 in 5 retirees plan to launch a new line of work that differs from what they have done in the past.*
 

9. No one told me that in my Second Act, I would find my new work life so rewarding!
 

10. No one told me that in (un)retirement, there are so many people just like me—people who actually feel younger, not older! *
 

* Work in Retirement: Myths and Motivations

**Growing Old in America: Expectations vs. Reality

Tags:    baby boomer   unretirement   career   lessons   second act   retirement  

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