The OBHF Podcast: Ep. 6 – Dads Who Inspire Me Series: Meet Jon Bailey

Dads Who Inspire Me.

Paul was pretty happy on Jon's wedding day.

Paul is launching a new series we’re excited about called Dads Who Inspire Me.

Jon Bailey, from 2DadwithBaggage, a travel and lifestyle blog kicks it off. He has been a family friend for many years, in fact we are godparents to one of his daughters. He and his partner Triton are dads to two teen daughters (we call them survivors!) and on this episode you’ll hear a bit about his parenting style.

Jon loves to travel and his family has been around the world on incredible adventures. He is definitely a dad who inspires!

In this episode you’ll find out about:

  • Jon’s favorite curse word(s)
  • How both Jon and Paul’s moms made their dads convert
  • Jon’s challenge coming out to his parents
  • Bringing the best of your upbringing to your family
  • OBHF Ep. 6 Transcript - Dads Who Inspire Me Series:Meet Jon Bailey

    From the Dusty Urban Ham Shack studio of WB6QWD this is the Our Bird Has Flown podcast.


    Paul M Bowers:Hey, and welcome to the Our Bird Has Flown Podcast, I’m Paul M Bowers. I’m here with special guest today Jonathan Bailey, say Hello Jon.

    Jonathan:  Hello Jon

    Paul M Bowers:Hello Jon to you. Jonathan Bailey has 2 Dads with baggage, that’s the integer But before we talk to Jon, I hear the chime and it’s time to talk about our favorite sponsor Green Fresh Florals is Carlos Franco, he’s our buddy in Hillcrest and San Diego if you get a chance to come by his shop. He has a most incredible shop, full of stuff, full of plants, full of pots, full of everything. Carlos is the greatest, and from, you can order arrangements for local or for international. Carlos has got it figured out. So, go check it out.,619-544-0504 and we thank Green Fresh Florals for sponsoring the Our Bird Has Flown Podcast. Now, Jon, you’re here because you have 2 Dads with baggage.

    Jonathan:  Yes. I do and two daughters

    Paul M Bowers:And two daughters. Now just so you know because we have to tell everybody the truth, you and I are friends, we’ve been friends for a long time.

    Jonathan:   Very long time, decades six or four?

    Paul M Bowers:Since before spouses actually, I think that Indra and I met the same week that you and Triton met.

    Jonathan:   I think it was very close, but I was there when you met Indra.

    Paul M Bowers: Well, at the, at the famous party that we covered in episode one I think. You were there for episode one?

    Jonathan:   No. I was not

    Paul M Bowers:Yeah, I think you were there; you were there for that magic moment. That wasn’t all that magic at the time but later obviously turned out.

    Jonathan:  Incredibly magical.

    Paul M Bowers:Incredibly magical and we have had parallel family lives, we have together gone through loss of parents, the birth of children, adoption of children. And you know you folks are the closest family that we have in parallel and in fact you guys are so important to us, that had we died at some point, then you would have had Jesse and here’s the good news only a couple more months and then you’re off the hook for that.

    Jonathan:   I think he’s pretty independent now.

    Paul M Bowers:Yeah but financially you know. So, I want to talk a little bit about fathers. This is a series specifically about fathers that I admire and people that I look to as inspiration for Dads. Dads who inspire me. And so, I want to ask you a couple of questions about your fathering, your parenting path how you integrated into your family, tell us about your daughter’s.

    Jonathan:   Well, Sophia is 16 going on 35 and Ava is 14 and a good solid 14.

    Paul M Bowers: And so, both in high school right?

    Jonathan:   No. Sophia is just finishing her sophomore year in high school, and Ava is being promoted. I love that word being promoted from the eighth grade. So, she’ll be a freshman next year.

    Paul M Bowers: And what do they like?

    Jonathan:   They’re awesome, they’re both wonderful, fun, intelligent, funny girls. We have a great time together. Sophia and Ava are both really different, and the same. So, they’re just like any sisters, they love each other, they hate each other, they fight, they share things, they rip things apart, but in the end, they’re the best family I could ever have hoped for.

    Paul M Bowers:I remember having sisters I had two of them. It seems so long ago.

    Jonathan:   It’s impossible for me to understand why both of them would want to wear the exact same tee shirt at the exact same time.

    Paul M Bowers:Well, I wouldn’t understand that either, I don’t like to have the same T-Shirt with anyone, but we all know about my fashion things. Tell me a little bit about the parent scenario in your house; do you have a lead parent?

    Jonathan:   Well, Triton and I from the beginning tried to parent equally. And so, having two Dads gives us the opportunity to parent a little bit differently. There aren’t two Moms in the family and so, we don’t fall to those regular stereotypical roles. We can split up responsibilities and regular duties fairly equally. So, from when they were babies, and we brought them home from the hospital, the feeding, the diapering, the waking up during the night, the laundry, the household chores and the love was really divided evenly between us.

    Paul M Bowers:You know in our house, we have these different roles and that’s part of ourbirdhasflown.comand it sounds like you are more on a parallel track than we are as far as those responsibilities go? Tell us about Triton.

    Jonathan:   Triton’s amazing. He’s, he’s the yin to my yang. He’s where I might be more outgoing, he’s more introverted, where I might be more hot-headed, and he’s more even-tempered. He’s–It’s a great balance and a great combination, he’s hilarious and a very, very talented artist, and very introspective. So, on the quieter side, but once you get him talking you get a lot out of him.

    Paul M Bowers:So, one of the things that I’m talking to…when I talk to Dad is, I want to talk about their family of origin and their relationship with their fathers. Because it tends to sort of define us as individuals and as Dads. Tell me about your Dad.

    Jonathan:   My Dad is so awesome. He’s my role model and father. He…when I was growing up, he was the most patient kind man that I could possibly hope for. I remember him when I was struggling with my math homework, and he would sit with me at the kitchen table every night after dinner and laboriously go through each and every problem until I kind of got it. But he had to do that with me, all the way through calculus in high school, where he was basically tutoring me at home. But he got me through and it and it’s just a microcosm of what kind of devoted, kind man he was to sit and give me that much time.

    Paul M Bowers:Were you a religious household?

    Jonathan:   Well, it depends on who you ask. I was raised in a Catholic household, my mom Sicilian Catholic was fairly clear about us having a Catholic upbringing and so although I didn’t go to parochial school. I did go to catechism class every Wednesday. And I did go through the whole process of first Holy Communion and then confirmation.

    Paul M Bowers:What was your confirmation name?

    Jonathan:  Christopher.

    Paul M Bowers:But that’s your brother’s name

    Jonathan:   Yeah, what was weird, she didn’t want us to have too many names. So, on our birth certificate we do not have a middle name. And she knew that when we were confirmed, we would choose a middle name and so that would be our middle name going forward. And interestingly, my brother chose Dean; my dad’s name. And I chose my brother’s name.

    Paul M Bowers:Is there a St. Dean?

    Jonathan:   I don’t know.

    Paul M Bowers:[Inaudible, 08:13]

    Jonathan:   So, my mom who got messed up with this whole thing was Anne Josefina Barbara. So, because her middle name was Josephina and then she chose Barbara. So, she thought that was way too much and Josefina Barbara Brewster Bailey was a little bit of a mouthful. So, she wanted us to have a simpler time. But yeah, so my Dad converted to Catholicism. and when I, when I became I don’t know, I was about 14, they sort of took the foot off the pedal and said okay, do what you want and that was it; never again.

    Paul M Bowers:Your mom, and I knew your mom, she was what I would call liberal.

    Jonathan:   Oh yes. She was very outspoken, and a little bit maybe unpopular in her church; just because she was pro-women’s rights, pro-abortion rights; very much about equal opportunity and very outspoken about it. So, she would I think to make some of the other people at church uncomfortable, certainly some of the ladies.

    Paul M Bowers:Isn’t that a shame? Because of the biggest hearted person one of the biggest hearted people I know was your mom and to kind of have that [inaudible, 09:26] very unusual. Your dad converted – what was he before?

    Jonathan:   Lutheran I think, but he wasn’t really anything. And so, he was just going on with what my mom wanted. And so, they were going to be married in the Catholic Church, whether he wanted to or not so he just went along with it.

    Paul M Bowers:You know it’s another astounding coincidence because my Dad was a Baptist and converted for my mom.

    Jonathan:   Yeah.

    Paul M Bowers:Much to the disagreement of his Baptist family who was not pleased with this, you know they didn’t have happy things to say about Catholics. So, you have a pretty straightforward upbringing, and sooner or later you had to let them know that you’re gay.

    Jonathan:   Yep.

    Paul M Bowers:And how did that go?

    Jonathan:  Oh with flowers and daisies and rainbows and I rented a unicorn and…

    Paul M Bowers:A pink unicorn?

    Jonathan:   Yes. I love a pink unicorn. You know actually, it was pretty painful. Growing up Catholic, I was told that was evil, and that I was going to go to Hell.

    Paul M Bowers:Yeah, it was a sickness.

    Jonathan:   Yeah and so I remember sitting across, I worked in the summers for my dad under his own business and I remember sitting with him at lunchtime, with all of the workers, all the guys that worked for him in the same lunch room. And somebody made a gay joke and you know everyone laughed and I didn’t laugh and my dad looked directly at me.

    And so, then I knew he knew, but he never asked me and I never said anything. So, when I finally got to the point where I was I think I was 21 and had been gay forever, but really kind of actively since I was maybe 16. And finally, I wrote them a letter, a very, very long letter. I was living in San Diego, and they lived in the Bay area and I sent them this very, very long letter spilling it all out. And they called me immediately. And my dad was super cool and just was like yeah, okay great we still love you. It’s all good.

    Paul M Bowers:You know we would go all time.

    Jonathan:    And my mom’s first words out of her mouth were what did I do?

    Paul M Bowers:Oh!

    Jonathan:   How do I cause this? So anyway, you know she…it took her a couple of months and she was fine. And they were, they were awesome. I mean Triton was another son to them; they treated him just like me. He was a member of our family. It was a very loving relationship.

    Paul M Bowers:And they supported and encouraged, and were enthusiastic about your becoming a family?

    Jonathan:   Oh! Yeah, in fact, Sophia was born three weeks after my mom passed away, and we knew she had cancer and it was terminal and so, it was down to the last, last few days, we flew up there and walked into her bedroom and our family priest who was a friend; his name was Declan, and he was in the room giving her last rites, and she said I want everybody out of the room. Jon, Triton you stay, and Dec you stay everyone else out. So, she looked at him and said Declan, I want you to promise that you will allow Jon and Triton to baptize their children, this baby. And any other baby they have in the Catholic Church and that you will do this for me

    Paul M Bowers:Wow!

    Jonathan:  And so, he said yes I will do that for you. And then she looked at me and Triton and said I want the two of you to promise this child, and any other child that you have will be baptized in the Catholic Church.

    Paul M Bowers:Wow!

    Jonathan:  Yeah, and she’s on her deathbed.

    Paul M Bowers:I know.

    Jonathan:   What are you going to say? Of course, yes we did. And at that time you know this was 16 years ago. That wasn’t done.

    Paul M Bowers:Put the priest in a very difficult position.

    Jonathan:   Right, and as you well know because you were there.

    Paul M Bowers:Yes, I was.

    Jonathan:  For that baptism and you are my daughter’s godfather. You had to pour water on her head

    Paul M Bowers:I did.

    Jonathan:   And stand on that altar and the lightning bolt did not strike.

    Paul M Bowers:It missed me like that much. Well, you know what, I think for both of us about you know our lifetimes are this tremendous amount of change particularly, for those of us with conservative Catholic parents. They had to face a lot. And it had to have somehow moulded the way that we parent. I know for me, my goal became to take the best part of my childhood and try to eliminate the not so good parts of it and add my own and we all know that…

    Jonathan:   Doesn’t every parent do that?

    Paul M Bowers:Well, I think that that’s the idea every, every thinking caring parent does that. Now, we also know that sooner or later our kids are going to end up on a couch somewhere saying you know my dad was this, my dad was that. But we try to minimize that and maybe save a little bit of money for him. So, that they have it they don’t have to go to college, they can go straight to therapy. Can you tell me a little bit about, how you have changed your parenting style versus what you were taught?

    Jonathan:   Well, I think I wasn’t taught a great deal of independence. I think my parents kept me very close. And I was much loved and revered and treated as though I was the golden child. But not, not allowed to make a lot of my own mistakes, not allowed to wander very far and explore. It was, I was held pretty close. And as a result, I feel like I had a very wonderful, warm, and loving upbringing and maybe I wasn’t as willing to take risk or as experimental or as adventurous as perhaps, I would like my girls to be.

    And so, although there are women, young women and this is a different environment in today’s world. We do still try to allow them some leeway so that they can have a little bit of a longer tether. And that is one of the things that I think I’ve tried very hard to make sure that I do. And yet you know I grew up in a family with so many wonderful traditions, around the holidays, and around food and around things that my parents just wanted to instil in us, as important parts of a family tradition. And so today I try to make sure that I pass on those same kinds of traditions to my daughters. So, Christmas and I mean Easter and even St Patrick’s Day, and all those other things become in our house a big celebration.

    Paul M Bowers:That you’ve been very successful at.

    Jonathan:   Yes. Even if [inaudible, 16:27]

    Paul M Bowers:You know I hear a chime right now, and you know what that chime means? It’s time to talk about our other sponsor which is; The National Conflict Resolution Centre NCRC is an incredible organization that seeks to promote civility and promotes non litigious resolutions of problems. And they have a tremendous number of mediators available for business disputes, or for divorce. And they have a number of programs that involve interrupting the pipeline to prison, they’re working in schools all over the country. It’s a tremendous organization and we are proud to have NCRC as sponsors. Go to and check out the good work that they do. Thanks, NCRC for your sponsorship. So John, tell me a little bit about the rewards of parenting. We’ll get to some of the trials of it, but what’s fun about it?

    Jonathan:   Every day is fun and although you know…

    Paul M Bowers:[inaudible, 17:34] every day?

    Jonathan:   Yeah, I would say every day. Even though it has its challenges and yesterday was a particularly challenging day. It is…I couldn’t imagine not having this incredible experience, and having my kids be a part of my life. I feel like it completed me, even more than being married and having a loving spouse. And you know I spent my entire life growing up with this huge family on both sides, Irish on one side, Sicilian on the other, tons and tons of kids. And I was sad because I felt like perhaps, I would never have that experience of being a parent, and adding to that giant growing community a family. And so, when Triton and I met and he made it clear that he wanted a family. It was like an aha moment for me.

    And so, I really do cherish the experience. They’re at the point now where they have their own personalities, and so we can have conversations about interesting subjects. And we encourage them to agree or disagree. So, we have good conversations. And I also really love traveling with them and exploring the world, and that’s another thing that my parents did not do for us as kids. Our vacations were with family, we went to stay at a family member’s home, and we hung out with family. We didn’t go anywhere or do anything. So, I had this incredible sense of wanderlust. And as soon as I was independent, I started trying to travel and I wanted to travel with my kids. So, that they get a sense of the world and see that, the world is a whole lot bigger place then our family, or our community, or our home,

    Paul M Bowers:Agreed and you listeners, you can read all about these at 2dadswithbaggage.com2 as an intruder or a digit

    Jonathan:   Or Numeral

    Paul M Bowers:Or Numeral. One of the more interesting parenting blogs I’ve ever read.

    Jonathan:   Thank you.

    Paul M Bowers:I like it a lot, and we’re stealing here. You know our loan is stealing right out here. Oh yeah, like Jon did it, I’m going to do something like that because it worked out so well for him. So, I must be able to do it just as well right.

    Jonathan:   Happy to give you a legal.

    Paul M Bowers:Tell me about the hardest part of parenting for you and for Triton.

    Jonathan:   Well, I’ll speak for myself, Triton is the perfect parent.

    Paul M Bowers:And he’s perfectly good looking.

    Jonathan:   And he’s very patient. And I think the hardest thing for me is when to shut up. And when to just give it a beat, let it have a moment, give it some silence and let them have their space. Because I tend to want to step in and tell them how to fix whatever it is or augment their behaviour or to do it this way because I know what they should do of course, because I know the right thing, but telling them sometimes doesn’t actually help. They sort of have to absorb it and learn it on their own.

    Paul M Bowers: Letting them struggle

    Jonathan:  Yeah

    Paul M Bowers:Letting them struggle on their own and overcome. I understand…I have a wife. Tell me a little bit about where they’re going. Are they headed for college or are they into careers? What’s next for the Bailey Klugh kids?

    Jonathan:Well, I think college has always been a hope. That right and I would like for them to go to college and we’ve been saving for it since they were babies. So, that’s a hard nut.

    Paul M Bowers:Yeah.

    Jonathan:I gather as you well know, and in the end though, they have to decide for themselves what sounds best and what would work best for them, and what they’re most interested in doing. Sophia, you know she does not love school, but she’s whip-smart. And so, I’m not worried about her in any way, incredibly street smart and very self-aware and very capable. So, whatever she decides to do, whether she decides ultimately to go to college, or pursue a career in something else. I mean she’s going to be great wherever she ends up. Hopefully, that includes college because I think it just gives her choices and we talk with her a lot about getting good grades because it broadens the number of choices you have in college or in life. Ava is just about to enter high school, and so, I think is still not fully formed in what she’d like to do, although she specifically says she would like to go to UC Santa Cruz and study in their writing program. And I have to tell you, she’s a fantastic writer. She’s brought several teachers to tears with her papers, and notes and essays.

    Paul M Bowers:Tears means good grades how about that.

    Jonathan:   Yeah, well whatever you got to do, you got to do.

    Paul M Bowers: [Laughter] So, she, she sounds pretty well focused. Now, is it your intuition that she’s going to stay that way or does she change a lot?

    Jonathan:   I think all kids at that age change a lot, from moment to moment, from hour to hour, from day today. So, what she says today or what Sophia says to us today might change by tonight. I don’t anticipate that either of them at this age is going to know exactly what they want nor would I really want them to. I don’t think they’re mature enough or developed enough to really know themselves and all of the possibilities that are open to them. So, you know when I went to college, I think I changed my major four or five times. I thought I was going to be an oceanographer. Yawn! I mean like I couldn’t imagine…I went to one class, it was chemistry and psychology, and this is not for me.

    Paul M Bowers:It’s not funny I did the same thing.

    Jonathan:   Did you?

    Paul M Bowers:Oh Yeah,

    Jonathan:And I went to UC Santa Barbara specifically because they have a great oceanography program and, okay, well that’s what I’m going to do. And I was like oh no, no I want fishes; I want to study pretty fishes. And it was not that. and yeah so, who knows what they would end up, but they think they’re going to do what they end up doing.

    Paul M Bowers:Well, because I’m a mechanic on things and return wrenches and fix cars I thought, you know I could be a mechanical engineer until Avogadro’s number came along 6.02×10 to the twenty-third. That finished off my engineering career completely. I cannot do the math, better find something else to do. Tell me a little bit about what’s going to happen at the Bailey Klugh home once the girls have flown. Are their rooms going to be preserved as a little memorial to them? Or what’s in your plan?

    Jonathan:    Well, we tease them about this a lot, and say that we’re going to rent their rooms out the moment they leave the house. And that we’re going to remodel and postmodern and they flip out. And it’s so fun to tease them and have them get– and they know that we’re actually teasing, but we have a very large house. And when they’re off on their own, I want them to have a place to come back to, for as long as they want to do that. And I don’t think that this giant house will be necessary for us as we age and they have their own lives, and their own spouses, and their own family. So, eventually, but not that soon not going to change.

    Paul M Bowers:A little juicy makeover on it.

    Jonathan:    We have talked about it when the time is right. There being our house, and going and staying in other people’s or Airbnb’s in other amazing cities around the world and sort of having a rotation but always coming home for holidays. So, when they come home from college for holidays, were there in-house in the homestead. But you know this is the only house that they’ve ever known. This is the house that they came home from the hospital that they’ve grown up in; every memory of every birthday, every holiday, every experience has been in this home so, it is far more than a home. It means much more.

    Paul M Bowers:Well, it is, it’s home. It’s far more than a house, that’s for sure.

    Jonathan:  Yeah

    Paul M Bowers:It is home.

    Jonathan:   Well said you know.

    Paul M Bowers:So, in the great tradition of James Lipton, and the tradition of Bernard Pivo before I let you go, let me ask your question, [inaudible, 26:20] What is your favorite curse word?

    Jonathan:    Oh am I allowed to say that?

    Paul M Bowers:I think you are because this ain’t radio.

    Jonathan:   Well, okay, I have two answers for you.

    Paul M Bowers:Two?

    Jonathan:   So, when I was growing up my parents tried really hard not to swear, although they both did, and they would try to keep it from us. And so, my dad would get really angry and his face would turn super red and he’d say God bless America! And it just to this day, it just makes me laugh. So, when I want to break myself out of my anger I’ll say that and I just think of my dad and that makes me laugh. However, my favorite swearword is really goddamnmotherfuckingsonofabitch.

    Paul M Bowers:You get the string of them, you get..

    Jonathan:   But it is one word. That’s one word. I say it is one word and therefore it becomes one very long complicated but all-encompassing

    Paul M Bowers:Very powerful and can be used in just about any circumstance.

    Jonathan:   Well, certainly on a podcast.


    Paul M Bowers:Well, that’s about all the time we have for the our bird has flown podcast today. I’d like to take a quick reminder of our sponsors Green Fresh Florals at greenfreshflorals.comand the National Conflict Resolution Center – podcast is remotely produced by Brian Thomas audio at Yokai audio in Kalamazoo Michigan. Be sure to visit our web site at www.ourbirdhasflown.comwhere we talk about our home life and our college bird Jesse Bowers. Jon Bailey thank you for joining us

    Jonathan:   Yeah, I’m glad to be here, thank you.

    Paul M Bowers:And listeners check out our next episode soon and be sure to subscribe to our podcast. Thanks very much and we’ll talk to you soon. Bye-bye.



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