Beyond the Sessions is answering YOUR parenting questions! In this episode Dr. Emily Upshur and I talk about…
- What “kindergarten readiness” actually means (and what it doesn’t).
- Dr. Upshur and Dr. Bren share their personal experiences – with one choosing to send her child to kindergarten and the other deciding to hold her son back – and why.
- The pros and cons of redshirting, and whether being one of the youngest in the class really leads to long-term struggles.
- Why social-emotional readiness may matter less than you think.
- How family logistics, finances, community norms, local school culture, and sibling dynamics can influence your decision.
- What research says about long-term academic and life outcomes.
- How to take the pressure off yourself so you can make a thoughtful, “good enough” choice.
If you’re going back and forth about whether to send your child to kindergarten or wait another year, wondering if they’re too sensitive or overwhelmed to start, or worried about making the “wrong” decision, this episode will help you zoom out, gather the right information, and move forward with more clarity and confidence.
REFERENCES AND RELATED RESOURCES:
👉 Want extra support in your parenting journey? Upshur Bren Psychology Group offers therapy and coaching to give parents the tools to feel more grounded and confident as they navigate parenthood and learn how to most effectively support their child. Visit upshurbren.com to explore our services and schedule a free 30-minute consultation call to find the support that’s right for your family.
LEARN MORE ABOUT US:
- Learn more about Dr. Sarah Bren on her website and by following @drsarahbren on Instagram
- Learn more about Dr. Emily Upshur on to her website
CHECK OUT ADDITIONAL PODCAST EPISODES YOU MAY LIKE:
🎧 Listen to my podcast episode about helping your child success in preschool with Meredith Gary
🎧 Listen to my podcast episode about helping your toddler learn to share
Click here to read the full transcript

Dr. Sarah Bren (00:02):
Ever wonder what psychologists moms talk about when we get together, whether we’re consulting one another about a challenging case or one of our own kids, or just leaning on each other when parenting feels hard, because trust me, even when we do this for a living, it’s still hard. Joining me each week in these special Thursday shows are two of my closest friends, both moms, both psychologists, they’re the people I call when I need a sounding board. These are our unfiltered answers to your parenting questions. We’re letting you in on the conversations the three of us usually have behind closed doors. This is Securely Attached: Beyond the Sessions.
(00:41):
Hi. Welcome back to the Securely Attached podcast. This is the Beyond the Sessions segment where we answer listener questions. And I have Dr. Emily Upshur with me today. Hello, Emily.
Dr. Emily Upshur (00:56):
Hey.
Dr. Sarah Bren (00:57):
How are you?
Dr. Emily Upshur (00:58):
I’m good. Good to be here.
Dr. Sarah Bren (01:00):
Yeah. Are you ready for our listener question?
Dr. Emily Upshur (01:05):
Let’s do it.
Dr. Sarah Bren (01:06):
Okay. This parent writes in. Hi doctors. I love that. Hi doc. Hi doctor. Hi doc. Hi doctors. My son’s birthday falls right on the cutoff in our town for whether we send him or keep him back from kindergarten in the fall. I keep going back and forth about what to do. Part of me worries, he’ll struggle if he’s one of the youngest and part of me worries. I’m holding him back for no reason. He’s sweet and bright, but he’s also pretty sensitive and can get overwhelmed in new situations. I just don’t know what matters most when you’re making this decision. Any advice you can give me would be so appreciated.
Dr. Emily Upshur (01:45):
This is so funny. We have one of each, you and I.
Dr. Sarah Bren (01:48):
Yes. You and I both our kids. And actually this description is my son sounds just like this kid and I red sheed him. I pulled him, he’s an October baby, and I decided to send him, he did a Cambridge year and then we did kindergarten a year after that. And you had the same sort of kid and didn’t
Dr. Emily Upshur (02:15):
I didn’t. Yeah. It’s so funny.
Dr. Sarah Bren (02:18):
And both of us have pros and cons to that. I mean, we can talk about our personal experiences. It’s funny this parent happens to be asking you and me.
Dr. Emily Upshur (02:28):
I know.
Dr. Sarah Bren (02:28):
Something that we both had personal experience with, but I also, I’ve worked with a lot of families and I’ve talked to a lot of teachers about this too. And there’s a lot of research on it as well. A lot of it is kind of like it doesn’t really matter. It doing, it doesn’t not necessarily give kids the leg up that they think it will. And there’s research on it. They’ve really done a good amount of research on whether or what’s commonly called red shirting, which is a term that comes from for sports. Really. People would do this so that kids could potentially be a little bit bigger, a little bit faster, a little bit stronger in sports. So the red shirting refers to Jersey stuff, but now I think that generally people do it for lots and lots of reasons, academic reasons, social and emotional development reasons. My personal reason actually was I just was like my kid could probably do kindergarten at, I think he would’ve been four at the start of kindergarten.
Dr. Emily Upshur (03:35):
Mine was 4.
Dr. Sarah Bren (03:36):
And I was like, yeah, he probably could do kindergarten at age four, but I don’t want him to go to college at age 17. I don’t know yet what he’ll be like at 17. And I was like, that felt young to me to go to college. I felt at 18, I felt young at my freshman year college. It was a little overwhelming for me and I was like, God, I just want him to cook one more year before going to college.
Dr. Emily Upshur (03:59):
Where it gets tricky is for this parent to back to this question where I advise, I’ve actually changed probably a little bit where I advise because I think it’s really tricky where in the greater New York area in Manhattan, New York, you do not get to choose, period.
(04:20):
You do not get to choose. There is a deadline, everybody follows it. The rule holds. It doesn’t matter if you were born on December 31st, you are part of that year, school year cohort. And if you try to hold your kid back, they won’t let you have to skip a grade. They’ll put you in first grade. So it’s really strict. Whereas in where we are about 30 minutes outside of New York City, you can decide. Anyone can decide. So it’s a little bit arbitrary and I think that’s where it gets a little confusing and tricky for people. There’s no hard rule.
Dr. Sarah Bren (04:52):
It also depends, not just, I mean you and I are in New York, so we know the New York ecosystem, but I grew up in Minnesota and in the Midwest school, cutoff dates are September, not December.
Dr. Emily Upshur (05:04):
Yeah.
Dr. Sarah Bren (05:04):
And so in a lot of other places, red shirting isn’t as big of an issue. I think it tends to happen more when the cutoff is December versus the beginning of the school year.
Dr. Emily Upshur (05:15):
The school year. It’s not academically.
Dr. Sarah Bren (05:18):
And so I think you see this issue more geographically in different areas, but then there’s also cultural elements to it as well. Socioeconomic, in Westchester, it’s very common to do it and therefore if you don’t, your kid could be as much as two years younger than kids in their class. Whereas if you’re in an area where it’s less common to do it, it doesn’t have as big of an impact one way or the other.
Dr. Emily Upshur (05:49):
Exactly. So what I was going to say is I’ve changed a little bit. I used to say don’t make a decision on your own. Talk to your kid’s, preschool teacher, talk to a professional. This is a choice that really should be made with data and I think your data is one of those pieces of input. But I would say collect a little from people that have seen your child if they’ve been in a formalized school setting, that’s a really good idea. And then get a sense of your community. I think had I been as aware of how prolific it was in my community to hold kids back, I might’ve made a different decision because my child is sometimes up to 18 months to two years younger than his peers. And that when you get a bit old, it feels a little weird for them. It feels weird for you, but it also feels weird for them.
(06:45):
So I don’t think that’s the wrong choice in an isolation for, I think you can make a choice, but you’re not making a choice in isolation. So I say get your feedback, try as much as you can to know your environment, your teacher’s input, the type of kid your kid is and sort of see how it goes from there. Your gender. It really is. There is a lot of factors at play and I think that can help you make a choice that. So I’d say now I say if it’s really aberrant in any way, then make sure that’s put in your, if most of your district, a lot of people have a tendency to red shirt their kids. Maybe you red shirt your kid, right? Because you would be really aberrant. But if your preschool teacher is saying, I wouldn’t red shirt your kid, your kid is going to get bored and then they’re going to poke somebody in the eyeball, that’s not a good idea. They really are ready. They might be aberrant in that way too and listen to that as well. So I think it’s more about putting a lot of different data points together instead of, I feel like the pressure on parents is so high, I want to be able to take that pressure off a little and say, use your community. Use the data and the resources you have to make a really informed decision coming from multiple angles and that will probably help you feel a little bit more settled once you land on it.
Dr. Sarah Bren (08:14):
Right. I think one point you’re making that I think is worth highlighting and even stretching out a bit is it’s not, I think a lot of times we think there’s the core reason one does this is because of readiness, this sort of abstract idea of readiness. And if they’re ready and we could define what variables go into that assessment. If they’re ready, you can send them and if they’re not ready, you should hold them back. And I think to what you’re saying is actually readiness is one of actually a number of variables outside of your child that might want to be factored in and given weight. Because a lot of kids, their readiness can shift drastically in a matter of months.
(09:01):
They might not look ready in end of preschool and by the summer before the following school year, they’re absolutely ready. And if they are super ready, I’m using air quotes, you can’t see that, but they’re very ready. You’re right. I think one of the risks to redshirting them is they are very bored because they’re in a milieu that is developmentally below where they need to be at. And it’s not stimulating enough, it’s not demanding enough, it’s not structured enough and they don’t do as well in that environment. That’s a risk. I think that’s a piece. But a lot of the readiness questions, I see kids who go into kindergarten who are questionably ready in their ability to regulate, tolerate new situations, break into social kind of negotiations, the sort of social emotional readiness, and they figure it out. In fact, being in a setting where they’re kind of forced to figure it out actually helps them to do so instead of holding off and…
Dr. Emily Upshur (10:22):
Well, they may never feel totally ready. It’s like how ready? We don’t know when they’re ready enough.
Dr. Sarah Bren (10:28):
So I guess all that has to say is I actually think quote readiness from a social emotional standpoint and even an academic standpoint. And I also think that will come with time. I actually feel like that’s almost not the reason I would consider redshirting as much, if that’s the only reason you’re doing it,
Dr. Emily Upshur (10:50):
Well, and I think we have to honor also different family systems. I think it’s not an option for everybody to do another year of preschool. It’s a really expensive sort of socioeconomic thing to do to decide as opposed to sending to your districted public school if that’s your path. So I think there are a lot of variables or it could be childcare or it could be you have four siblings at home, maybe getting out of the house and going to kindergarten is a good choice for you. There’s just so many variables. I think that that’s just some of the data points that I think all have to factor into your choice ultimately in the end. And I will also say you’re not going to do anything irreparable. There’s a lot of different ways we can for the pros and the concept of each way. I think there’s a lot of different ways that we can scaffold children to be as successful as they can no matter which choice you land on. And I think that’s reassuring as well.
Dr. Sarah Bren (11:53):
And that’s why I think parents get put under this sense of pressure about readiness. Because a teacher might say they’re not showing signs of readiness and you’re like, I actually can’t really choose not to send them anyway. And then they’re feeling anxious about readiness. And a kid, a four to 5-year-old in kindergarten will figure out their readiness when they’re ready. And it doesn’t really matter if they do kindergarten or Cambridge or another year of fours in the preschool, they’re still going to get there eventually. So I actually think a lot of the anxiety that some parents have, and I’m not necessarily hearing that in this mom’s question, but I know parents who are asking similar questions or who maybe listen to this episode because they have similar questions. It’s kind of the other way around. It’s like, and I’m not sure if they’re ready, but I can’t take another year off. They got to go to kindergarten. Am I messing things up if I do this, if I rush them? And I think, no, I think it’s probably, it’s kind of six in one, half a dozen in the other. And there’s going to be pros and cons and your kid might have a bumpy year regardless.
Dr. Emily Upshur (13:19):
And also they might have a bumpy year at some point. I feel like for different situations, it could be ninth grade, that’s the bumpy, or because your kid’s a lot younger or a lot older or whatever.
Dr. Sarah Bren (13:35):
I mean, my son’s having a bumpy year now because he wishes he was in the older grade. And there is even there’s that. He’s like, why am I not with my camp buddies? Why am I not with the people who I went to daycare? He knows he’s not. And that just happens to be also his cohort in his grade happens to be kind of on the younger end of the spectrum. So he’s way older than a lot of the kids in the class. And that might not happen in every school and it might not be an issue. And again, I’m still like, I don’t want you going to college at 17. That was my big thing. It wasn’t that you couldn’t handle it. Now it’s that I just needed to know that your brain had an extra year of cooking before I sent you off into the world.
Dr. Emily Upshur (14:26):
And I love you. And also if your child had been born two months earlier, you wouldn’t even be thinking about that. So it’s, it’s the same thing. I just want people to be flexible about how they think about it. Had my son been born two months earlier, I wouldn’t be like, is this the decision I should make or not?
Dr. Sarah Bren (14:46):
I think at the end of the day, we all just put so much pressure on ourselves, make the quote right decision and it doesn’t really matter.
Dr. Emily Upshur (14:52):
That’s right. And I would say shout out to all our teachers in kindergarten who are teaching kids at a two year age developmental stretch. I know like you guys are the real warriors. I know that’s a really challenging position to have so much diversity in your kindergarten classroom, but they all seem to do a great job. And to your point, kids figure it out and if they have trouble, they get support and we’re here for that too. I think that that’s in either way, I just think it’s the pressure that we put on ourselves to make sure everything is right or just right, just right. We just need to go back to good enough and the best we can do can sometimes be just enough.
Dr. Sarah Bren (15:32):
So I hope this was helpful and I just want to recap. One, there are many variables beyond readiness to pay attention to when making this decision. Sometimes it’s not the ones you think that actually might weigh the most in this decision. Financial things, what your cohort, your community is tending to do so that it’s not about following what everyone else is doing. That’s not what I mean. But understanding generally what are the age ranges that are going into kindergarten. If they’re way different from your child’s age and you want it to line up, that’s something to consider because being two years younger or two years older than your cohort is a bigger difference. Is a bigger issue. And so that might be more important to think about.
Dr. Emily Upshur (16:22):
How many kids you have at home, right? What’s happening with your family system?
Dr. Sarah Bren (16:29):
And yes, readiness is a piece, but I also think at kindergarten there’s just so much discrepancy in readiness anyway that just go. If you’re worried you can go. And also if you want to pull ’em back, I think that’s also totally fine. You can’t mess this one up. Hopefully that helps.
Dr. Emily Upshur (16:50):
Let’s all say a prayer for my 17-year-old going to college.
Dr. Sarah Bren (16:54):
Right? Right. Yeah. No, that’s my anxiety. That is nothing to do with my kid. That is me projecting my freshman year experience onto my child. A hundred percent. So funny. You guys got this.
Dr. Emily Upshur (17:07):
You got this, you’ll work it out.
Dr. Sarah Bren (17:08):
Alright. Thanks Em.
Dr. Emily Upshur (17:10):
Yep.
Dr. Sarah Bren (17:10):
Thank you so much for listening. As you can hear, parenting is not one size fits all. It’s nuanced and it’s complicated. So I really hope that this series where we’re answering your questions really helps you to cut through some of the noise and find out what works best for you and your unique child. If you have a burning parenting question, something you’re struggling to navigate or a topic you really want us to shed light on or share research about, we want to know, go to drsarahbren.com/question to send in anything that you want, Rebecca, Emily, and me to answer in Securely Attached: Beyond the Sessions. That’s drsarahbren.com/question. And check back for a brand new securely attached next Tuesday. And until then, don’t be a stranger.

