Carl and his wife Diana sitting at a table covered in copies of his book "Pickle ball for dummies"

Lessons Learned: My Three Years of (Un)Retirement—A Chance to Reinvent Yourself

I just passed my 3-year mark of what we like to call (Un)Retirement. It’s about no longer having that 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).

Carl as a freshman college student and Carl in retirement

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 at 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.


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 weren’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 tradeshows 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 too 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 changed to a monthly podcast and newsletter and would first fill my calendar with pickleball 4 times a week, then fill in the fun things with friends and family, and what was left over timewise 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 take a stand-up comedy class and perform in front of 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 in the sixth class, 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) for 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 20s, 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 just a 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 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.

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The Author: Carl Landau, Guest Author

Host of the making-the-most-of-retirement themed podcast, "I Used to Be Somebody" and co-author of Pickleball for Dummies.