When Your Child Doesn’t Fit the Life You Planned | Robert Delana (Part 1)

What happens when your child doesn’t fit the life you thought they would?

In this episode of The Gentle Year, I sit down with Robert Delana to explore what it means to parent a child who challenges expectations at every turn. From early behavioral concerns and school interventions to misdiagnosis and therapeutic placements, Robert shares the reality of raising a child who didn’t respond to traditional systems—and how that experience reshaped everything he believed about success, discipline, and parenting itself.

We talk about the pressure parents place on their children, how labels and diagnoses can shape identity, and what it feels like when your child wants connection but can’t seem to find it. This conversation also raises deeper questions about school systems, behavioral expectations, and whether some children are being misunderstood rather than supported.

If you’re parenting a child who thinks differently, struggles in traditional environments, or doesn’t follow the expected path, this episode will challenge you to rethink what your child actually needs—and what it really means to help them thrive.

Resources & Support:

Turning The Tide Tutoring – Academic coaching and support for students who think differently

https://turningthetidetutoring.com

Transcript

SPEAKER_01 0:00

Most parents say that they just want their kids to be happy. But underneath that, there's usually a very specific definition of what that happiness is supposed to look like. And when a child doesn't fit that definition, that's when everything can start to unravel. This conversation with Robert Delena focuses on what happens when a child completely reshapes your understanding of parenting. Welcome to the gentle year. Robert, it's amazing to have you on the show today. I'm so excited to have you to talk about this really important issue today. So I'll pass the mic to you if you could please introduce yourself and share a little bit about your story.

SPEAKER_00 0:56

Thanks, Nikki. Uh as you said, I'm Robert Delana. I live in Sudbury, Massachusetts, which is just outside of Boston. I'm here today, I suppose, because of my parenting mistakes, uh, all of which I own in a book called Without Restraint, which we'll we'll talk about. Um really, it's my son's journey. My son was firstborn, and um, you know, I I was uh a pretty successful guy, I think, up to my parenting. I my wife and I had sort of grown up uh very blue-collar backgrounds, ended up doing pretty well and moved out to the suburbs. We were both lawyers and uh had good careers. And when our son was born, I think we thought he would take it to the next level. He would be the better version of us. And we, you know, put a lot of emphasis on, you know, his success right out of the gate. And he was a kid who struggled. He was a kid who wouldn't sit still, he was very bright, uh, but he questioned everything. He loved to say no and he didn't listen to anything that I said. And I thought maybe this will serve him well and he'll run the world one day. But when he got to public school, you know, in and um right from the start, and before Kenny got in preschool, uh the schools flagged him as being too difficult to handle. And they suggested that we put him in some special programs, which led to his placement in a therapeutic school where in the therapeutic schools were a disaster where he was restrained and isolated and and and the wheels really came off the off the wagon. And um, and you know, we faced a lot of decisions that parents don't want to face early on as to you know whether or not he could go to school at all, and you know, if he should be on medication. And so we made a lot of disastrous decisions, which we'll get into up sure in more detail. But um, one day I I took him skiing and I wasn't a skier, I just was looking for something to do. I had run out of trips to Home Depot and things, you know, trips to the park where I'd have to apologize to every other parent. And I just, I don't know, there was this little ski hill near our house. And I remember thinking, well, maybe one day we'll try that. And we went and we had for us what was a successful day because nothing disastrous happened. And I remember driving out of there and thinking, that wasn't terrible. And we went back the next day and the next and ended up, you know, touring all around New England, all around the country, all around the world. We ended up uh skiing in Antarctica, which nobody's ever gone to Antarctica. And uh my son became this sort of well-known, you know, you know, extreme skier and outdoorsman, and then life changed. And it changed for me as well, because all along the way I saw this different kid that nobody else was seeing. And we were spending a lot of time together and traveling. And I would go back and tell my wife, everybody's wrong. Every, you know, all the doctors are wrong, and all of these schools are wrong, and and then this kid is much more than people think. And um, so I really learned a lot on the fly, and I learned a lot about myself and those early parenting mistakes and and what what fueled them, I think. And and so we ended up writing this book together called Without Restraint, which um really chronicled that whole story. And then I think uh it's it's been received, you know, well by parents of kids who've struggled, kids who you know have issues, but really parents of all kinds. I mean, uh every kid, I think, today is faced with um never feeling like they fit in completely. And and I think Ryan was a perfect example of that. And and to see him thriving now, you know, I would like to say it's a testament to my parenting, but I think he succeeded in spite of my parenting, and and that's part of the fun of the story. So long introduction, but that that's that's kind of why I'm here.

SPEAKER_01 4:17

No, that was perfect. It really does give us a wonderful overview of what we need to unpack today. So I appreciate that introduction very much. One of the things that you said stood out to me is the idea that parents feel that their children should be better than they are. Where do you think that that idea comes from?

SPEAKER_00 4:35

Insecurity, I think, you know, some of these stuff that we've we've fight through, I think, and the stuff that fueled my wife and I as being, you know, kind of kids who didn't have a lot and and and really striving and we always had to outwork everybody else. And I think when you get to a certain point, you think, okay, now my son's gonna start here. I started here. If he can take that same, you know, approach that I had and and and you know, obsess about everything and worry about everything and always be looking over your shoulder, he's gonna be, you know, wildly successful. And so, you know, right from the start, and and we all do this with the first kid, you know, if they don't sit up first, you know, the other kid in the neighborhood crawled first, or you know, you'd think, oh my God, it's over. And with Ryan, he was just, you know, he in the beginning he was really smart and he was and he was a the kid who could do a lot of those things. You know, he was very athletic. Uh, and the fact that he just ignored everybody else and and, you know, was obsessed with the task. I thought, okay, you know, socially, you know, we might have some problems, but he's just so driven, he's gonna be fine. It was when he got a little older and you could see, you know, that he would he wasn't gonna fit in. And then that's when that insecurity plays back in. You think, oh my God, I now have the kid. Not only is he not gonna go to Harvard, he's gonna be on the special needs bus. Like this is this is the worst case scenario. I can't imagine. Where did I fail? You know, now we've got to fix this, you know. So, you know, I look back on a lot of those early decisions and think, you know, that was, it was, you know, I was just so afraid to have a a child who fit that, you know, because of me, my ego, right? It really had nothing to do with him. And it's that's where a lot of guilt comes in. And I I I think I've come to terms with a lot of that. And I and I realized that it was just me being afraid of having, you know, God forbid, a kid who wasn't the best at anything. And, you know, it's it had nothing to do really with him. And and so I think it was the bet in a long way, long answer, the best thing that ever happened because when you have a kid who struggles and then it all falls apart, and it and we can get into this, it did all fall apart. And you just want him to be happy for 15 seconds, and that's the goal. And it and Harvard isn't the goal anymore, you know, it really does recalibrate what's important in life. And I think for me, that was that was a journey worth taking. Uh, one I you know I don't relish and I don't wish on anybody, but now as I sit here as a 57-year-old, I'm I'm glad I did take it.

SPEAKER_01 7:05

Let's take a moment to slow this conversation down because underneath the surface of what Robert is saying is a lot of information. So I'm going to leave you with three questions that really sit at the center of this conversation. Question number one, how much of Robert's early parenting approach do you think came from his own expectations and ego? And how much of it was shaped by modern day society's expectations around him? Which of those do you think played a greater role? Question two, if you were in this same position, what would taking ownership as a parent have led you to do? And number three, what impact do you think it had on Ryan to be labeled so early on and how might that have shaped the way his parents began seeing him and his behavior? What was going on with your child? I kind of want to just unpack that mystery because I'm thinking to myself, okay, if he's not social, maybe he was autistic, or maybe he had some emotional disorder or something like that. What was really going on with your son?

SPEAKER_00 8:17

So the original right when he really struggled, we we at the time, now this is 2000, he was born in 2001. So 2002, 3, 4, you know, they would screen you in or out for autism, right? And he clearly wasn't autistic because he was so verbal and he never stopped talking and he never stopped moving. You know, so we we quickly left that. And then when it became behavioral, we did bring in a pediatric neuropsychologist at that point. And she she described this imbalance in his brain that he was very left-brained, he was super smart in you know, in the left-brain stuff, and he wasn't he was very weak in the right brain stuff, which knowing my wife and I made perfect sense, right? We're very type A-driven people, not creative, not artistic. So I remember thinking, all right, she's probably on the money with that. But she also at the time said, in order to get services from your town, we've got to call it something. We've got to put a diagnosis on this. And so I remember her flipping through the DSM, the diagnostic statistical manual, like all the they don't sort of every mental illness in the world is in this book. And she starts stumming through it and she ends up landing on uh pervasive developmental disorder not otherwise specified. Now, I guarantee there's like 20, you know, whatever, 200 people in your audience nodding saying, My kid has PDD NOS too, and none of them are the same, they're all very different, but it's this bucket category. It's it was on the autism spectrum where they just really don't know what to do with kids, and then they they'll dump them into PDD NOS. And so Ryan was was put into that bucket. You know, he he's all he is a little different, he's quirky, I would say. He's he's got a photographic memory, he's he's very, very verbal and very bright. Um, but he did have some deficits, I'd say, you know, recognizing cues, um, you know, other people's emotions. I don't think that came very naturally to him. Um, if he was in a room full of kids, he would fixate on objects, not people. I mean, so he had some of the spectrum-y stuff you'd you'd expect. But then there were other parts of him, you know, he he really craved being around other people, he really wanted friendships, he wasn't the super introverted kid that where he didn't fit. So, you know, I as I tell people at the end of the day, he's just Ryan and you can call it whatever you want, but you know, his his main issue was that he didn't like to listen. And and and when he was a kid, when I was running around with him, I got a kick out of it. But once he went into a classroom full of 20, 30 kids, if you're the teacher and you have one kid who won't sit still, who's like in the bathroom looking under the sink because he wants to study the plumbing, that's a problem. And and I think so he he just was a different kind of kid. And you know, I think had we had we forced the town to say, you know, tough luck, just deal with it. He would have been a kid who spent a lot of time in the principal's office. But I think I would have forced them to get creative, you know, and and if he was a kid that didn't want to do the art project, you might have had to take him down the hallway and walk around and show them some lights and and plumbing and get and then maybe get them back to the table that way. Instead, you know, we were convinced that if we just cracked down on him, if we just made, you know, made his world smaller and really pushed him, and that's where the therapeutic schools came in. And there were kids at therapeutic schools that did okay. I mean, there was, you know, special programming, it was individualized, it was, you know, they previewed, they transitioned things. You know, there were things that he benefited from. But the fact that they could put their hands on him and and restrain him when he got dysregulated led them to restrain him a lot, you know, and in the and to restrain him prophylactically. When they saw him not listening, instead of giving him a chance to sort of write the ship, they immediately pounced on him and would restrain him. And so then he got this fight or flight, you know, tick where he just really thought he would always get manhandled anytime he said no or disagreed or or didn't want to do something. And it really just was the worst thing. He probably would have benefited, ironically, from like a Montessori program where they just kind of let him, you know, be himself. And and it never dawned, and we back to our parenting sort of insecurities, that never dawned on us. Like, let's give him more freedom. Instead, it was like, we gotta crack the whip on this kid. And and if you don't, and they would say this to us if you don't, he's gonna end up dead or in jail. That's what the therapeutic school would say to us all the time. And I remember thinking, like, you know, I guess that makes sense. Oh my god, he's gonna get pulled over by a you know a cop one day and he never listens. He does whatever he wants. He's gonna, you know, he's gonna this this is gonna lead to some terrible decisions as an adult if we don't crack down when he's a kid.

SPEAKER_01 12:49

There was obviously a lot said in that portion of the interview, so let's unpack this gradually. First, we're gonna take a look at what pervasive developmental disorder is. According to my research, it is a former diagnostic category for a group of conditions characterized by delays in developing socialization and communication skills, often including repetitive behaviors and restricted interest. Since 2013, these conditions are generally classified under autism spectrum disorder. The doctor also suggested that Ryan may be left-brained, which means that a person may have a preference for logical, analytical, and objective thinking. This concept is also referred to as a verbal or digital brain that prioritizes linear, sequential, and factual information, such as language processing, mathematics, and detailed orderly tasks. With this information in mind, I'm going to present to you three questions that will conclude this interview and lead us into part two. Question one, how do you personally discern the difference between a behavior that's developmental, environmental, and one that truly requires intervention and or treatment? Number two, with Ryan specifically, how aware do you think he was of not fitting in socially? And was Robert going through his own version of this as a parent? Question three. How do you know when a child needs more freedom over restriction? And when does a child need more restriction over freedom? Understanding how your child thinks changes everything. When that understanding is there, you start to see where they're getting stuck and how they process ideas and also what they need in order to grow. That's the focus of my work at Turning the Tide Tutoring, an academic coaching and support program for students who think differently and need a more personalized approach to writing, learning, and communication. You can find more information by visiting turningthe tutoring.com. And if this episode gave you something to think about, I'd really appreciate it if you followed the show, left a rating or review, or shared your thoughts in the comments. It helps more people find these conversations. And thank you so much for being here with The Gentle Gear.