#42 – The Final Chapter: Retiree Reinvention & The Launch Of Tryin Ryan

Ryan Doolittle [00:00:34]:
And I’m really looking forward to Ryan’s new video called Trying Ryan. I can’t wait for it to come out.

Ryan Doolittle [00:00:43]:
Well, what can I say, folks? The great Jill Smith, Intrican. She was indeed the very first guest of the Happiest Retirees podcast. And I really appreciated her because she brought us that momentum out of the gate. She said, hey, look, I had this long career, and it was a good career. Three decades as a teacher, you’d think that was it, right? No, because after 30 years of teaching people how to write, she decided she actually wanted to be the one writing. So she said, let’s get started. And that’s what we’re doing here today. We’re saying, let’s get started, folks.

Ryan Doolittle [00:01:17]:
Let’s get started on your happy retirement. So while the recording light of this studio might go dark, I want your life to light up more than it ever has, and I want that to start right now. Do you ever wonder who you’ll be and what you’ll do after your career is over? Wouldn’t it be nice to hear stories from people who figured it out who are thriving in retirement? I’m Ryan Doolittle. After working with the Retire Sooner team for years and researching and writing about how they structure their lifestyles, I know there’s more to be learned. So I’m going straight to the source and taking you with me. My mission with the Half Happiest Retirees podcast is to inspire 1 million families to find happiness in retirement. I want to learn how to live an exceptional life from people who do it every day. Let’s get started.

Ryan Doolittle [00:02:10]:
So, as Jill alluded to, this podcast in its current form is turning into a YouTube video series called Tryin Ryan. Now, my name’s Ryan, and I’m gonna be Tryin. So that’s pretty much how that brainstorm sesh went. Anyway, I’m really excited about the new series. Each episode will have me picking out a new core pursuit, which again, is a hobby on steroids, and trying it. I mean, it’s pretty simple. But I think that’s also the beauty of it you can see me pick something, go try it, see how I do, if I love it, if I hate it. But what that will show you is that you can do it, too.

Ryan Doolittle [00:02:48]:
Because I think this gives people a chance to see visually what it looks like to go out there and try these core pursuits, especially if you’re someone like me who may not be good at these things, which is exactly what it’ll be like a lot of the time for people out there. You’re gonna try something new. Why would you be good at it? You’ve never done it before, right? It takes time to get good. And if you love it, you’ll love taking that time. Those 5,000 hours, or whatever it was in that Malcolm Gladwell book will seem like five seconds if you really love doing it. And that’s what the Try and Ryan video series is all about. You might find something you really, really love. And the more you do it, the better you’ll become.

Ryan Doolittle [00:03:27]:
The essential part is trying it. Getting out there and being active and doing something you love doing. That’s what really helps make retirement special, meaningful and full of purpose. And speaking of purpose, I got another great voicemail from a former guest, retired FBI agent and current author and podcaster, Jerry Williams.

Jerri Williams [00:03:50]:
Hi, it’s Jerry Williams, author and host of FBI Retired Case Law Review. I just learned that the Happiest Retirees podcast is, well, being retired. I’m sad to see the show go away. I’ve admitted before that listening to the show’s guest, other happy retirees like me, was like going to therapy to validate. I was doing retirement. Right. Ryan was the star of the show, and fortunately, I’ll still have the pleasure of listening and watching him on his new video series, Crying Ryan, Ryan, now, we retirees taught you how to have fun, and I can’t wait to virtually tag along with you on your fun adventures. Congratulations.

Ryan Doolittle [00:04:43]:
Jerry is just the best. She spent 26 years in the FBI, and then she used that career as a springboard for a thriving second act as an author, a podcaster, a speaker, and a TV consultant. She works on a show that one of them’s for J.J. abrams. I mean, she’s doing some major stuff. For her, it was less of a retirement and more of a reinvention of what she was going to do with her days. So, like many of the happy retirees I’ve interviewed, she’s actually very busy. I mean, she said that at one point, she.

Ryan Doolittle [00:05:14]:
She was afraid she was doing retirement wrong because she’s so busy, but she’s doing what she wants to do. That’s the difference. That’s the key of. Of retirement lifestyle, is that you get to do what you want to do. And I thought it was funny. She said, the greatest thing about retirement is not having to deal with an alarm clock. And I think that really just speaks to how you’re doing, what you want to do, when you want to do it. That doesn’t mean you’re doing nothing.

Ryan Doolittle [00:05:40]:
It just means it’s on your terms. And just a couple of fun facts about Jerry. I asked her, since she was in the FBI and she consults on TV shows. I said, you know how there’s always some cop, some local cop on a show who says, don’t give me any of that jurisdiction crap? I said, is that really what happens out there in the streets? And she said, no, that’s. That’s so false. That’s such a cliche. The FBI and the local police, they’re always working together to help solve crimes. So I just thought that was really interesting.

Ryan Doolittle [00:06:10]:
And you only get that from speaking to some authentic law enforcement agent. And her passion for her career is actually why she launched her podcast, because she knew agents with great cases, and she thought these stories need to be told. So in case you’re looking for a great podcast about the FBI and retirement, it’s called FBI Retired Case File Review, and it’s highly recommended. Jerry is living proof that retirement isn’t about slowing down. It’s about leveling up on your own terms. I mean, her second act blends purpose, freedom, creativity, and service. She’s building a legacy through stories, hers and others. I mean, she does all these podcasts about her fellow FBI agents.

Ryan Doolittle [00:06:54]:
So she’s modeling what an active intentional retirement looks like. Jerry says, make sure you’re actively participating in your life. And I think this goes along with what Jill Smith Intricate said. Let’s get started. This is the time to find joy and do the things you’ve always wanted to do. Thank you so much, Jerry. Our next voicemail comes from a guy who spends a lot of time on the pickleball court.

Ryan Doolittle [00:07:21]:
Hey, this is John Hiles. I was trying to get a hold of Ryan. I’m at my office right now on the pickleball court, but I wanted to tell Ryan how much I’ve enjoyed listening to his podcast and wish him luck in the future and how much I enjoyed being on it. Hope somebody learned something from me, because I learned a lot from the other guests and wish you well in the future. Thanks a lot for letting me be on the show.

Ryan Doolittle [00:07:42]:
I love that you can literally hear that he’s out of breath from playing pickleball. If that isn’t the sound of a happy retirement, I do not know what is. It’s interesting that he identified himself as John in the voicemail. As a professional, he went by John. And then when he retired, more and more people started to call him Johnny. And so in a way, retirement recreated his identity. He became Johnny. John had to get up every day and go to work.

Ryan Doolittle [00:08:09]:
Johnny gets to explore the world, enjoy his family, and even tackle that honey do list. What’s better than that, right? At least for yourself. Spouse. Now, in addition to playing pickleball four to five times per week, Johnny also does other workouts and he attends a weekly men’s Bible study and volunteers as a greeter every other week at church. At the time of our interview, he and his wife had just taken their first trip to Greece and Turkey with their sights set on taking a big trip at least every other year. And that is something you can do in retirement. You can take your hard earned money and finally go see the world if that’s something you want to do. And for a lot of the happy retirees that I talk to, travel is definitely a big passion, a big core pursuit.

Ryan Doolittle [00:08:54]:
So it seems like Johnny and his wife were on their way to finding that passion for themselves. I think the big thing here was that John had to act like a grown up, but Johnny was far too happy for that at the time. It had been a year since Johnny retired, so I called him a rookie and, and I think it was safe to say then that he was well on his way to a promising career of happiness. Johnny, thank you so much for your support and for being on the Happiest Retirees podcast. My final voicemail comes from a guy that I met when my wife and I took our toddler to the Santa Barbara Zoo, which is a beautiful zoo in a gorgeous city in Southern California. In the zoo, they have this train ride where you hop in and it you take a tour of all the animals and the. The train conductors explain what you’re looking at and tell a lot of dad jokes. So Andy was one of the train conductors on that ride, which he now does in retirement as a volunteer gig.

Ryan Doolittle [00:09:52]:
But what you’ll hear about his primary working years is pretty fascinating. I’d say more, but it’s probably classified.

Andy Leitman [00:10:02]:
Yeah. Hi, my name is Andy Leitman. I was on one of Ryan’s retiree podcasts. Was really happy to have crossed paths with him. I think I always realized that retirement was cool. I had a long and fairly stressful career at the federal government in CIA and was a senior manager back in Washington. Moved to Santa Barbara and did lots of things, and now I’ve ended up driving the train at the Santa Barbara Zoo. And I did a podcast with my friend Pete, who ran an insurance company here in Santa Barbara.

Andy Leitman [00:10:33]:
He also drives the train. The podcast was a great opportunity for us to realize how important it is to have fun and do something that you enjoy when you retire and how great retirement is. It’s not the end of anything at all. It’s really the beginning of lots of new adventures. That sounds sort of like a cliche, but I have found here in Santa Barbara, it is absolutely true. Ryan asked lots of good questions, really made me think about my choices, and again made me conclude that I had made a lot of good choices. Thanks and good luck to everyone who’s retiring.

Ryan Doolittle [00:11:07]:
If you could see a picture of what Andy and his friend Pete, who I also interviewed, look like when they’re driving the train. I mean, they look like actual train conductors. They’re in overalls, you know, they got the hat. They just, they look like a fun train conductor. And so imagine my surprise to find out that Andy had been very, very high up in the CIA. It didn’t compute until I actually talked to him. And he’s such a smart guy that it, you know, immediately it makes sense. But I asked Andy about how it felt to go from such a high level job to volunteering at a zoo, and he said he actually loved it.

Ryan Doolittle [00:11:44]:
He loves the lack of responsibility. He went from having to make these big budgetary decisions about things that I think affect the security of our nation to. To only having to figure out which otter wants which piece of fish. And I thought that really encapsulated his new journey in retirement. I liked how Andy was able to let go of his ego. I mean, you imagine someone in such a high level job could possibly have one, maybe you would even need to have one to have that job. But he didn’t bring that with him to the train. And in this volunteer job in retirement, he just found the joy in being a train driver and making people happy.

Ryan Doolittle [00:12:25]:
He joked about taking orders from people half his age and loving it. So Andy is a fantastic example of what joy filled retirement can look like. Meaningful volunteering, humor learning, mentorship, and genuine friendship. He proved that retirement isn’t about slowing down. It’s about finally choosing what lights you up when you get to retirement. The train literally keeps on driving, it’s just on different tracks. And on these tracks, you’ve got a much better view. So, yeah, Andy might have gotten in trouble once for saying the wrong facts about one of the zoo giraffes.

Ryan Doolittle [00:13:01]:
But even so, when it comes to making the riders on his train happy, Andy will always stick his neck out and in turn, their happiness makes him happy. Well, that’s all, folks. I want to thank Jill, Jerry, Johnny, and Andy for leaving me very, very kind voicemails. I want to thank all the happy retirees who sat across from me and shared their stories so that we could learn how we can be happy. I want to thank our showrunner Mallory, our audio production genius Marissa, producer Lauren and editors Jerry and Mandy, the great Patrick Terrell for letting us use his music, the PR and marketing team Andrea, Elizabeth and Zippy, Natalie over at Porchlight, the compliance team, Helen and Holly M. For keeping us from being sued, Holly W. The C Suite exec who believed in us, and of course, the godfather of retiring Sooner and happier, Mr. Wes Moss.

Ryan Doolittle [00:13:55]:
All of these people will be with us as we move over to the Tryin Ryan YouTube video series, which launches on April 30. Make sure you follow us on the Retire Sooner Team channel. That’s Retire Sooner team on YouTube. We’re bursting out of the gate with a really fun episode about cooking the delicious food. And hey, you might even get to meet my wife. I’ve had a great time on this podcast, and I hope we’ve helped more folks find happiness in retirement. I’ll see you over on YouTube. And until then, remember to take some time to figure out what gives you purpose and what you want to do when you finally have the time to do it.