I just went past my 3-year mark of what we like to call (Un)Retirement. It's about no longer having the big job and now you have the time to freestyle and figure out what you want to do with the remainder of your life. There are just a few times in your life that you can naturally reinvent yourself. The biggest opportunities for that are; 1) after you graduate from high school or embark on a career path, and 2) life after the big job, aka NOW (for some of us).
 

The normal benchmarks for success previously come to us as annual reviews at work or if you're an entrepreneur, it's a profit/loss company statement. At this post-career stage of life, those metrics don't apply anymore. Not a all! It's a total self-examination that's completely wide open and even a bit challenging. Don't compare yourself at this point in time to your friends and peers. You can be totally subjective and it's all up to you if you want to evaluate how you're doing.

The one universal thread that rings true (and I know it might sound obvious) is we all need purpose when we wake up in the morning to get out of bed. It doesn't matter what that purpose is-- whether it's spending time with a grandchild, starting a new company, volunteering for a cause you are passionate about or playing a sport like pickleball. You've got to have that drive. And for extra credit, if you create a diverse set of passions, all the better!

What I've learned
It takes time to figure out this (Un)Retirement thing. Like most people, it's not so easy in the beginning. Getting used to this sort of wide open yet vague new world is weird! I spent the first year worrying that I should be doing more things and in the back of my mind, I felt like I was forgetting something from my work. I was so used to running a business for my entire adult life that it was ingrained in me that I always had to be super busy.

 

Work PTSD
Once I slowed down, I realized that I actually suffered from some sort of PTSD from the event business I ran for 20 years. For years I would have bad nightmares about the event I was working on. I think it was from the pressure of getting enough attendees to sign up for the events. And my recurring nightmare was that we aren't ready for attendees, lots of scrambling. It makes no sense because we were always ready. But, it took me two full years until the nightmares finally faded away. 

New Stuff
What I really enjoy doing is creating new projects and businesses. I started my (Un)Retirement during the pandemic. I love listening to podcasts and I decided to start working hard to create a new podcast business with me as the host. On a whim, I called my new company Pickleball Media (because l also love pickleball) and our target audience is Baby Boomers who are at the forefront of the (Un)Retirement AND pickleball wave! 

When I started researching the pickleball industry, I realized that there were incredible business opportunities. There were no real business-to-business conferences or a tradeshow in this emerging sport. Maybe I could seize the opportunity and make a ton of money and get that high from creating another new event. But, instead.......

Learning to say NO 
I said "no" to the pickleball opportunity because it would have taken me right back to where I already had been. I decided to move forward into the new with my life and not go back to the stress and anxiety of the event business (remember the nightmares). So now I have a new rule for my (Un)Retirement. "If it sounds like so much work, I don't want to do it." I'm not afraid to work hard. But I don't want to be consumed by work ever again. I've moved past that now.

 

Changing course
During the first year of (Un)Retirement I started the I Used to be Somebody podcast and newsletter every week. I truly love doing it. But after 10 months I realized that this weekly schedule felt like real work again (see above rule #1). I used to fill out my Google calendar with all the interviews and deadlines for the podcast and newsletter and if I had any extra time available, I'd play some pickleball.
 

Once I noticed this trend, I reversed my work / play agenda. I went to a monthly podcast and newsletter and would first fill my calendar with pickleball 4 times a week, and then fill in the fun things with friends and family and what was left over time-wise went to work. I reversed my priorities......and I'm so much happier!

Getting out of your comfort zone
Probably the most difficult yet satisfying thing I've done so far in (Un)Retirement is to take a stand up comedy class and perform before 100 people. I've always been interested in stand up and saw a new class taught by a very talented comedian Jack Gallagher, here in Sacramento. I saw an ad on Facebook and signed up immediately for the workshop without even discussing it with my wife or anyone else. I was afraid if I told someone and thought more about it, I'd chicken out.

We've all seen stand up comedians. It looks easy. Trust me, it's not easy! Not only do you write your own material but you need to deliver it as well. (Which are entirely different skills, btw.) I have so much respect for comedians now. We only had five classes, two hours a week and then on the sixth one, we performed live before a big audience. The last thing I wanted to do was embarrass myself and bomb. I took the whole thing very seriously. I probably practiced my set 80 times. (Just ask my wife.)

Jack's goal was for each of us to do a five minute set. My set ended up being 12 minutes and I fully expected Jack to cut it down at the end. At our dress rehearsal one week before the show, I asked Jack what I needed to cut out. He said, "No cuts. It's great! You're going to do it all."  At the show, I nailed it. It was one of the highlights of my life! Carl's 12 minutes of Comedy Gold. 

Taking risks reaps rewards
So the decisions I've made so far in (Un)Retirement have given me a new perspective on what matters most: 

• Sleep matters. With less stress in my life, I sleep so much better. I used to sleep on average about 5 1/2 or 6 hours a night. Now I get my full 8 hours of sleep plus a short afternoon nap sometimes. Sleep is so important for  overall health.

• Exercise matters. I play pickleball 4 days a week now. And I walk 10,000 steps a day on the non-pickleball days. I've lost about 8 lbs. this past year. I stretch / meditate (with my cat Felix) 20 minutes every day and love it!  I feel much better physically and mentally.

• Friends matter. I've reconnected with several friends from my childhood and 20's and visited them. Since my career took me out of town a lot, I didn't have much time to meet people locally. Now I've got more local friends than I've ever had. Just joining a pickleball club gave me a dozen new friends that I see all the time. As you get older, an active social life makes a huge difference in your state of mind.

• You matter. Learn how to say NO. I simply avoid negative people and things I don't want to do. No more endless zoom calls and I've stopped doing online presentations. (Do people really want to watch 3 talking heads on a Youtube video?) I spoke at a live, in-person conference last month in New Orleans and loved it. I don't want to live in an only-virtual world. I want to make real connections with inspiring people and I don't need to do it only online.

I think the biggest thing I've learned so far is not to worry so much about stuff.  Most of our worries aren't something that we can control or influence in any way. Somehow I've developed a new mindset that allows my worry quotient to go down. 

Of course, I don't have all the answers to my life all figured out yet. But, after 3 years of (Un)Retirement, I feel like I know some of the questions and I like the newly reinvented me.

Tags:    the carl diary   unretirement   comfort zone   pickleball   stand up comedy   second act   reinvention  

You need to "practice what you preach". We're always encouraging listeners on the I Used to be Somebody show to try doing something NEW and more FUN. So, I felt like I had to try something new.....

WARNING: For anyone trying something entirely new ( a second act), at the beginning you're going to be frustrated, scared, overwhelmed and at some point you're going to want to give up. These are natural feelings. It's supposed to be a challenge! So have patience and give yourself a break when trying something new. 

I signed up for a six week comedy stand-up workshop and our final was performing before a live audience. I learned a ton by taking on this project and it really kicked me out of my comfort zone.

• Stand-up is HARD, and not just because you are talking in front of an audience with bright spotlights focused on you. You have to learn to take command of the room while at the same time you are trying to get a very specific response from the audience -- laughter! (And not just once but for most of the time you are up on stage.)

• You have to be a good writer, develop a script, memorize it and then successfully perform that set without note cards, which are four entirely different skills. Oh yeah---and be really funny!

• Find a great mentor, it makes a difference. I was so lucky because I had the incredible comedian, Jack Gallagher, who has had a big time career in comedy and acting.

Jack told our class, "Regardless if you continue with your stand-up career or not, the experience translates into big-time confidence in anything else you do in the future. If you can do stand-up, you are bullet proof for anything." I think this is totally true.

Tags:    the carl diary   stand up comedy   comedy   comfort zone   comedy gold   funny   jack gallagher  

I talk about getting out of your comfort zone a lot on my I Used to be Somebody show. It's is a big theme of the show and one of the reasons I started the podcast. I wanted to challenge myself to see if I could have a successful podcast after selling my company and also to help others figure out how to create their own successful second acts in life.

So I just took a big leap! I recently confessed to comedian Greg Schwem, a guest on the show, that I had just signed up for a stand-up comedy workshop. We meet for 6 weeks and for our "final" my classmates and I each get a 5 minute set in front of a LIVE audience. 

I saw this class advertised on a Facebook post. And there was no one at that moment who I could talk to, in hopes of "talking me out of it." So I immediately signed up before I chickened out. I was literally shaking as I filled in my credit card info to pay online for the workshop.

I just had my first session. Our teacher is the very talented Jack Gallagher who I actually had interviewed last spring for my show. He's been a comedian / writer / actor for 40+ years. Another reason I signed up for the workshop was to meet and get to know the other weirdos like me that want to try this stand-up thing. I wasn't disappointed. They come from all walks of life. Everyone there had a different reason for attending. We are an interesting bunch for sure but it all seemed to be good- hearted and supportive. Which is what you need in a nerve-wracked environment of stand-up comedy.

And as Jack pointed out.........a five minute set is waaaay longer than you think. It's also a very long time if you're bombing.

Jack had each one of us go up on the stage right away. He wants us to feel comfortable on that stage. Some of my classmates have already done some stand-up. Some have an acting background. Oh, and then there is me.

The first time on the stage was easy. Jack did a Q & A session with us -- our life story, why we were there and who are favorite comedians were. I did fine. The second part on stage was a complete disaster for me. Jack performed a 3 minute comedy bit and each of us took turns to repeat that set. Just about everyone was able to jump up there and do their version of the bit. I was in total panic mode while watching everyone else. 

Ironically, the set I'm working on for my own stand-up set is that I'm dyslexic and how I've had to deal with it my whole life. Sometimes my brain gets jumbled up and I don't have the skills to do exactly the task I want it to do. So my 28-second act was a disaster. My classmates politely clapped and I sat down mortified. 

I'll do another diary entry before my final stage performance. I'm actually eager to go back next week. I was successful by showing up and making the effort. I certainly got out of my comfort zone. And you know what? Nothing bad has happened to me yet.

Tags:    the carl diary   stand up comedy   comedy   comfort zone   try new things   unretirement   Jack Gallagher  

Carl interviews stand-up comedian Greg Schwem this week. Greg not only does stand-up comedy but he has performed on Jay Leno, with Celine Dion, and corporate gigs like Microsoft and United Airlines. Greg talks with us about his third act in the comedy world – as the creator/producer/director/writer/performer of a funny new YouTube show, “A Comedian Crashes Your Pad.” (Fun fact: Greg is also a kick-ass pickleball player!)

Greg grew up in middle-class Arlington Heights, a burb in Chicagoland. He says he gets his funny bone from his father, who was an electronic salesman. “You have to be funny to be successful in sales,” he says. Gutsy move: Greg was an introverted teen and not a big “joiner” until he performed stand-up for the first time at 16 at his high school. “Making people laugh has a lot of advantages socially!”

After graduating from Northwestern, he worked as a journalist, working for different media. At 24, he moved to Florida and started going to comedy clubs as something to do in the evenings. He soon discovered he enjoyed being a stand-up comedian more than he liked being a journalist. His parents were wary at first, but he says when he brought them to Las Vegas years later and they saw his name on the marquee, they realized he could make a living doing what he loved.

After two decades of performing as a stand-up and doing corporate gigs, he taught himself some new things. “COVID taught me some video skills,” Greg says. He began creating a new show about a comedian who visits people in their homes through one of the home-sharing sites, learning about their quirky lives. “When people are in their own element, you’d be surprised how much they open up.” Greg shares, “When I started it (the show) it was just me with an iPhone and a GoPro.” He now has a crew of one to help with the camera work.

Greg's career is still going strong as he re-invents himself. He also loves performing at senior communities. “It’s enjoyable to see people who've worked hard and are now in the second or third act of life. They really enjoy laughing—especially about themselves. It’s refreshing to see them really respond.” Greg still performs around the country when not working on his YouTube show and of course, winning at pickleball. “I am going out on a cruise ship soon and I can’t wait to see people of all ages in one room having fun!”

Greg’s (Un)retirement advice:

• “Laugh! It’s so cliché but I believe laughing is good for your health and keeps your mind sharp. At this age, that’s so key.”

• “It’s never too late to try something new. Also, don’t worry about what others think of you!”

• “Look for the next FUN project! I don’t care where you are in your life, it’s out there.”

• More about Greg Schwem

• 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” weekly blog.

Tags:    blog   interview   unretirement   pickleball   comedy   stand-up   third-act  

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