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

Back to Blog

Subscribe to the podcast on
Apple Spotify or More

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  

    Categories

    Show All (61)
    baby boomer (3)
    career (6)
    top 10 list (1)
    time management (1)
    time tracking app (1)
    task list (1)
    retirement (11)
    (61)
    unretirement (33)
    lessons (2)
    second act (7)
    blog (58)
    andy levine (1)
    interview (42)
    marketing (3)
    andy robin (1)
    the tapas life (1)
    ascenium (1)
    executive (3)
    cinde dolphin (1)
    coors (1)
    cancer (1)
    entrepreneur (7)
    boomer (5)
    Dan Kennedy (1)
    Small Business (1)
    yoga (1)
    zen (1)
    meditation (1)
    Sacramento (2)
    journalism (3)
    facebook (1)
    comedy (3)
    paul ollinger (1)
    crazy money (1)
    dartmouth (1)
    financial planning (1)
    financial advisor (1)
    Alan Newman (1)
    Risk Taker (1)
    entrepreneur (1)
    rebellious (1)
    barry pincus (1)
    CFO (1)
    bo sacks (1)
    high times (1)
    magazine (2)
    Bob Tuschman (1)
    Food Network (1)
    Exec (1)
    NYU (1)
    Professor (1)
    Caroline Ceniza Levine (1)
    pivot (1)
    dream job (1)
    CEO (1)
    smart living (1)
    real estate (1)
    Princeton (1)
    Silicon Valley (1)
    Stanford (1)
    Unretirement (1)
    Chris Farrell (1)
    chris welles (1)
    rhinos (1)
    foundation (1)
    cycling (1)
    author (10)
    advice (2)
    Dan Blank (1)
    publishing (2)
    memoir (1)
    entrepreneur (1)
    Debb McColloch (1)
    Deborah McColloch (1)
    philadelphia (1)
    housing (1)
    volunteer (2)
    devon zagory (1)
    food (3)
    entreprener (1)
    Dr James Beckett (1)
    baseball (2)
    baseball cards (1)
    sports (2)
    collector (1)
    podcast (8)
    Ed Casey (1)
    Doctor Who (1)
    licensing (1)
    merchandise (1)
    Tim Jordan (1)
    coffeehouse (1)
    small business (1)
    local (1)
    Midtown (1)
    soul (1)
    baking (1)
    coffee (1)
    henry schulman (1)
    giants (2)
    Jack Gallagher (1)
    performer (1)
    risktaker (1)
    Larry David (1)
    improv (1)
    Kerry Hannon (1)
    writer (1)
    finance (2)
    retirement plan (1)
    horses (1)
    ageism (1)
    challenges (1)
    Mark Shaiken (1)
    photography (2)
    charity (1)
    Melissa Davey (1)
    film (1)
    documentary (1)
    director (1)
    vice president (1)
    michael clinton (1)
    magazines (1)
    editor (1)
    mike branon (1)
    pickleball (3)
    mo nard (1)
    life lessons (1)
    website (1)
    second acts (1)
    patrick mulvaney (1)
    farm to table (1)
    chef (2)
    restaurateur (1)
    nonprofit (1)
    community (1)
    mental health (1)
    jim roddy (2)
    book (2)
    walk on (1)
    Joan Ryan (1)
    Giants (1)
    bestselling (2)
    Michela OConnor Abrams (1)
    adversity (1)
    future (1)
    new beginning (1)
    Richard Turner (1)
    poetry (1)
    scott miller (1)
    pilot (1)
    investor (1)
    sacramento (2)
    dreams (1)
    cfo (1)
    finances (1)
    recession (1)
    val haller (1)
    music (1)
    baby boomers (1)
    naps (1)
    WNBA (1)
    General Manager (1)
    basketball (1)
    legend (1)
    NBA (1)
    halloffame (1)
    collegescholarship (1)
    sacramento (1)
    Jill Baker (1)
    success (1)
    (un)retirement (1)
    joe pulizzi (2)
    content marketing (1)
    luck (1)
    episodes (2)
    mark shaiken (2)
    attorney (1)
    law (1)
    moira mcgarvey black (2)
    best selling (1)
    bestselling author (1)
    passion (2)
    mike krukow (2)
    try new things (1)
    food network (1)
    bob tuschman (2)
    quotes (1)
    joan ryan (1)
    debb mccolloch (1)
    bary pincus (1)
    michaela oconnor abrams (1)
    richard turner (1)
    retirement association (1)
    retiree (1)
    vacation (1)
    mini-retirement (1)
    work (2)
    budget (1)
    superfan (4)
    star of the week (4)
    best-seller (1)
    novel (1)
    anne da vigo (1)
    painter (1)
    artist (1)
    rancho la puerta (1)
    socal (1)
    club change (1)
    susan stewart (1)
    golf (1)
    retailer (1)
    lgbtq (1)
    third act (1)
    unretired (1)
    life of freedom (1)
    transformation (1)
    comfort zone (1)
    robin pajaro (1)
    hypnotherapy (1)
    embracing change (1)
    passions (1)
    steven petrow (1)
    UC Berkeley (1)
    Duke (1)
    humor (1)
    hope (1)
    grace (1)
    worst jobs (1)
    working (1)
    job (2)
    bonus episode (1)
    Bob Franceschelli (1)
    blog (2)
    Anheuser Busch (1)
    ceo (1)
    mike drak (1)
    writing (1)
    banking (1)
    bestseller (1)
    naps (2)
    power nap (1)
    business tips (1)
    caffeine (1)