#140 My Personal Reflections on the Power of Plebe Summer

Plebe Parents Weekend can feel like relief, but we see it as something stronger: proof that you and your plebe can do hard things and finish what you started. We reflect on why Plebe Summer matters even when the details blur, and why this milestone deserves real celebration, real rest, and real gratitude.

We also get personal about the reality behind the uniform. From scary life events and illness in the people we love to career uncertainty and conversations about postpartum depression, we talk about how Naval Academy graduates and military officers still feel fear, sadness, anger, and confusion. USNA does not “fix” your emotions or erase hardship. What it can develop is courage, and we define that clearly: courage is not the absence of fear, it is taking action in spite of it, even when that action is imperfect.

For parents, we tackle the hardest mindset shift: you cannot protect your child forever, but you can support a path that prepares them for life’s storms. For midshipmen, we share why the academic year does not get easier and why that is the point. This conversation is for anyone navigating resilience, leadership under pressure, mental health, and what it means to keep moving forward when life is heavy.

If this helped you, subscribe, share it with a fellow USNA family, and leave a review or comment so we can keep supporting midshipmen and parents on this journey together.

To stay most up to date with Grant, Naval Academy updates, and real estate insights, follow him on LinkedIn

The mission of Academy Insider is to guide, serve, and support Midshipmen, future Midshipmen, and their families.

This podcast is independently produced and reflects the views and opinions of its creators. It is not officially affiliated with, endorsed by, or representative of the United States Naval Academy or its affiliates.

Grant Vermeer your host is the person who started it all.  He is the founder of Academy Insider and the host of The Academy Insider podcast. He was a recruited athlete which brought him to Annapolis where he was a four year member of the varsity basketball team. He was a cyber operations major and commissioned into the Cryptologic Warfare Community. He was stationed at Fort Meade and supported the Subsurface Direct Support mission.

He separated from the Navy in 2023 and now owns The Vermeer Group, a residential real estate company that matches service academy families with trusted real estate teams all across the country.  Text (650) 282-1964 with any real estate questions.

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Transcript

Why Parents Weekend Matters

SPEAKER_00 0:00

To me, pleep summer wasn't just about the Oak, it wasn't about shooting guns, it wasn't about gray space, it wasn't about any moment in specific. Um, and yet it was still one of the most powerful experiences my entire life. And in this video today, in this conversation that we're gonna have, I'm just gonna reflect on my plebe summer experience, uh, especially as you get ready to head into plebe parents weekend. It was my intention and my hope that I was gonna be able to speak at the plebe parent mixer leading up to Parents Weekend. Um, that is no longer the case. And so I just want to have the opportunity to address everyone in the way that I would have liked to in person. Um, but I think it's maybe even better this way, because I hope I get an opportunity uh for some of the plebs to hear it as well, and anyone who may be listening, um, because it has more to do with life than even the Naval Academy specifically. Um but doing Academy Insider has been just the most beautiful blessing in my life because I get the opportunity to reflect constantly, to go back and think back on my experience and have that be at the forefront of my life uh as I go through life and remember and reflect upon the lessons that I've learned and the things that I've gone through as a result of my experience in Annapolis. And then on top of that, I get the opportunity to accompany you on your journey through Annapolis along that same road, right? And so my first thing that I want to say is just congratulations on making it to Plea Parents Weekend, parent or midshipmen alike. Congrats on making it to Parents Weekend. Um, it's a huge accomplishment. Like it genuinely, it genuinely is. It genuinely is. Doing hard things is hard. And uh making it to Plea Parents Weekend is a massive accomplishment. Uh, I hope you get the opportunity to celebrate, uh, to relax, to have companionship, um, to share fun stories and just be with your loved ones, right? Like that is truly hopefully the purpose of Parents' Weekend for you guys to like be able to embrace and have communion and companionship and break bread and have these special moments with your loved one who has just gone through a really difficult experience. I also challenge you to reflect. I challenge you to pray, to think about the experience that you just went through. Um because, you know, again, every time Plebe Parents Weekend comes up and plebe summer comes up in this journey, and as a result of Academy Insider, uh, I get to talk about it, I get to reflect on it, I get to communicate with families who are actively going through it again. And these themes never change. I think that's like the most beautiful thing about it is every year it is very similar conversations we get to have because the purpose and the mission

When Life Gets Brutally Hard

SPEAKER_00 2:40

of Plebe Summer hasn't changed. Um, and this one was especially powerful for me this year. Um, I think especially important for me this year. Um, because this year has been brutally difficult for me. Um really hard year. Life happens, it's a hard year. Um, you know, within the last 10 months, um, you know, my wife was involved in a helicopter crash. Um, my brother was diagnosed with cancer. Um, my best friend continues his battle with stage four colon cancer. Um, it's a lot of changes in my world. Um, you know, I've tried to iterate my work with all these changes and have struggled, regressed a little bit, taking steps back, hopefully to project forward um in a positive way. But it's been difficult, right? Like that's been really tough. Um, you know, as a uh honestly, as a result of Academy Insert, which has been cool. I've had the potential um, you know, for a potential career change. Um and the excitement associated with that is really, really cool. Um, and you know, we'll see. Obviously, nothing's ever guaranteed, but it's potentially looking like that might not even actually pan out the way that I was potentially expecting it to. Um, and so again, like it's life, right? Like this, this isn't this isn't a a pity party by any means. Um, I just think it's important to recognize, and especially for me as I'm reflecting on my plebe summer journey, um, that there have been so many moments throughout the 13 years, roughly, right? 13. I showed up in 2013, it's 2026. The 13 years since I showed up in Annapolis, but especially in this last 10 months, there have been so many moments where I've wanted to stop, right? Like just give up. And um, you know, I've gotten close, to be honest. I've been, I've been sad, I've been unmotivated, I've been confused, without direction, um, I've been frustrated, angry. Um, you know, my brain has started to to justify just like slowing down, just slowing down work or pausing to see how things will play out while things are ambiguous or up in the air. We don't have much clarity. Um, you know, I still um I still very constantly fall to my humanness, right? Like I still constantly, I feel all the things that humans feel when they go through tough times, right? I've um every emotion, right? The the lack of motivation, the confusion, the frustration, the anger, the sadness, um, again, all these things, I still fall victim to my humanness constantly. Um and you know, what's really interesting is that I also had a conversation recently, like literally within the past week, um, with another dear friend of mine, um who a Naval Academy, same, same, you know, same background, same experience, um, who is who is kind enough and vulnerable enough to share, you know, her battle uh with with depressions, you know, specifically postpartum depression. And um, you know, it's just it's just hard, right? Life is hard. Um, whatever hard is for you, right? Like nobody's circumstances are necessarily the same, um, but the human struggle is the same, I think, in a lot of cases for a lot of different people. Um, and again, I think what's really interesting is if you looked at us from the outside, right? Like you looked at us, you'd think we have it all together. And I like to think I still pull it together to present and um and do all this stuff. And if you looked at her, you'd be like, wow, what an incredible life that she's living. Um and you know, I think we get to this point where you know, we see Naval Academy graduates, we see high education, we see success, you see someone who's a military officer, um, and you assume that everything is is great, that all this training has put them in a position to be exactly where they're at, and things are good. Um and while we are all of those things, uh we're also people, right? We're also humans. And at the end of the day, none of us knows to the full extent what is going on in someone else's life, and life is hard, right? And so I just think it's really interesting because I think a lot of

Courage Means Acting With Fear

SPEAKER_00 7:20

people think about plebe summer or they think about the naval academy experience, and they'll say, like, oh, but doesn't the Naval Academy teach you how to like avoid this, how to be brave? Doesn't the Naval Academy teach you how to have courage, how to be brave, how to not end up in these spots? And I just like, you know, to me, again, that's my reflection on this pleep summer for this year, because the answer is no.

unknown 7:46

Right?

SPEAKER_00 7:46

It's not teaching you how to not end up in these spots. Um, you know, I actually think as a result of the career path that we've chosen and the responsibilities that we'll have, um, that we may end up in actually more difficult and more precarious situations and spots. I think we end up in spots where life can be extra difficult, where on top of our own humanness, we, you know, we're in a position to take care, and you've heard me talk probably in previous conversations, about embracing and adopting and picking up the burden of others as well, your sailors, your Marines, your people that you are with, your ability to deal with your own struggles and carry the burden of the emotions and the struggles of your sailors and marines as well. Because at the end of the day, life is hard and being human is complex. And uh, you know, as I think about this past 10 months for me, uh I just uh I think it's so interesting because I think it's proven to me uh that we all still experience all of the emotions, right? We still experience fear and we experience insecurity and we experience confusion. And so as a result, right? Like when I reflect on the Naval Academy and Plebe Summer, um no, the Naval Academy doesn't take those things away. The Naval Academy doesn't take away your fear, it doesn't take away your insecurity, it doesn't teach you how to not have those things. What I'd argue is that it develops courage. And courage, in my opinion, kind of like as I reflect on this stuff, um, it's not the absence, like courage courage is not the absence of fear and insecurity and confusion, um, but it's the willingness to take action in spite of those things. Right? When you have those things, are you able to continue to move forward, to continue to take action, even if it is imperfect action. And for me, again, over this past 10 months, the fear of losing the people that I love most in the world um hasn't gone away. The insecurity of not being where I'd like to be in my ideal career path, as if everything was going great in my life, um, that insecurity doesn't go away. In the confusion of my direction and where we're going in life and how all these things are gonna end up and land, and you know, wanting to have a clear path and clear direction to move forward, um, it doesn't go away. It doesn't go away. But I like to believe I have become a person, and it's a constant battle, it's a constant journey, as we talked about. I still fail, I still fall to the victimness or like to the being a victim of my humanness. Um, but I like to be believe I've become a person more equipped to deal with those situations and with those with those moments. Um, and all of that traces back to pleep center. That is the first moment. It is the first time, again, if you've heard me have these conversations, it is the first time that I learned how to deal with going through storms, how to deal with adversity, to deal with the physiological stress and anxiety of being in difficult moments and being exhausted, um, and continuing to move forward anyway. Right. And I've had plenty of difficult moments at the Naval Academy. But what happened during Pleep Summer set the foundation to make me better equipped to deal with the next issue, to deal with the next hard moment of life, which then is another repetition of doing difficult things and then making it to the next step and just repeating and repeating and become becoming more equipped and more equipped to deal with the hard moments in life. And so, again, as you're listening to this, as your son or daughter may have just like finished pleep summer, is like getting to the end of pleep summer, and you may, you may have been on an emotional journey yourself of like, I wish I could help them. I wish I could, you know, protect them from these uh these terrible things. I just want my kid to be happy, right? I think it's just like the most common emotion I hear all the time from parents that I just want my kid to be happy. Um I encourage you to reflect on the purpose of Pleep Summer and realize that making it to Plea Parents Weekend is proof that you can do hard things.

Let Hard Things Build You

SPEAKER_00 12:32

Proof that you can make it through a difficult moment and finish what you've started to get there. And, you know, again, for my parents out there, I encourage you to realize, and this is a tough shift, right? Like we all have ego, and it's not like, oh, I'm the best ego, but we all have a personal ego where we have a feeling of our roles and responsibilities. And I know that you want to like protect your children, like you want to protect and provide them in a great life and make sure that they're happy and give them everything that you wish you would have had. And you know, again, I've just through all of this, I just realized that like you can't protect them forever, right? Like you're never gonna be able to protect them for every moment of their life. Um, but you can hope that they're prepared to be courageous in life's hard moments, because that will be the thing that actually protects them. Right. And so I just hope that as you reflect on this, that you walk away from Plea Parents Weekend with an eternal sense of gratitude and appreciation for the path your son or daughter has chosen, because they are actively building themselves into a person who will be equipped to deal with life's hard moments, and they will be the ones who are able to continue to take action, to continue to move forward in spite of all of the things that they are feeling. And if there were any plebes listening to this, like I don't know why you would be doing it on your few hours off of Plea Parents Weekend. Um, but here's your reminder, right? Like coming to you directly, you know, 31 years old now. Oh, yikes. Uh, you know, nine years separated from the Naval Academy, um, which also feels weird. You know, my peers are putting on 04, which is crazy. Um, right, like you're never gonna be able to run and hide from life, from life's hardships. No matter how good you think you can do it. Again, I I had a great life. I've had a great life, I have a great life, and yet it's still hard. And like it will always be hard. But the best thing you can do is just prepare yourself to be courageous and to be better equipped to handle it all. And that's what this is. Like, I hope you have an immense amount of pride in what you have just done because it is the first, it is the first step. It is the foundation in getting to that point, right? Because when you go to reform and school starts, um, you know, the ac year is not gonna get easier. I like the ac year is not getting easier. Again, last week we had a podcast episode about the shift from first step to second step. It doesn't get easier. Again, you just get more used to it. The ac year is gonna be hard, and and I would argue you don't want it to be easier. Because again, I think the whole purpose of this journey, a massive piece of this whole journey, um, is continuing to build that repetition of weathering a new storm, handling adversity, going through all of these moments in a controlled environment. Um so that way you have it under your belt and you know you will have proof that you can do hard things and you can handle the next challenge. And I hope you can reflect on that and think back to all the moments during pleep summer that were like that were tough, that were really difficult, that you wanted to not be there. Um, and have appreciation for those moments. Right. Again, if you have an opportunity, there's a book called The Obstacle Is Away by Ryan Holliday, right? Like it's not even you're not even successful in spite of the obstacles or the difficult moments, but rather you are successful because of those moments, right? Like you are difficult because or you were good because of the obstacle. You are a better human being because of the hard things that have happened to you in life. And um, I just encourage you to like truly be appreciative and thankful for what this experience is and for the continued difficulties that you will face, the continued hardships, the continued difficult moments. Uh again, it doesn't make them better. It doesn't make them any more fun. Uh, and I don't even think it makes it any more palatable. Um, but if you can at the end of the day reflect on the fact that, like, wow, I'm grateful for that because it's going to make me a better human. It's going to make me someone better equipped to deal with hard moments. Um, then that's the beauty of it all. So as you enjoy this wonderful time together over Plea Parents Weekend, again, I just encourage you to think and appreciate what a special life path that you are on and how incredible the Naval Academy is, and how cool it is that we have an opportunity uh to relate with all this. I had an opportunity to meet with um, you know, a rising youngster. Someone just finished their plebeir at the Naval Academy, who's out here for Pro Tremented San Diego. We were able to get lunch last week, and um it's just this is a bond, it's a connection that you just because you have the shared experience and understanding, and you know, we had conversations, like you know, like you know, we're separated by a decade uh in our experience, but you know, we're able to share and relate on so many different things, and it was so cool for him and I to have that opportunity to sit down and talk about his life because again, like he was questioning his being there, right? Like in no shade, no surprise, right? Like that's just it is what it is. It doesn't stop, it continues and it makes us question, it makes us doubt, it makes us have those feelings and thoughts in our brain um about escaping to a life of a little bit more comfort. Um and I just I just encourage you to you know truly be grateful for the fact that you're not on that path. Um and that you're not, you know, living for ease and comfort. So um I apologize that it's a bit of a ramble, uh, that it's not like a prepared speech. Um, but I wanted to kind of get that opportunity to say those things. Congratulations to everyone who's made it to Plea Parents Weekend. Um, if there's ever anything I can do for you guys as you move into the academic year, please let me know. Um, again, I appreciate your patience with me. That I, again, I haven't been able to put stuff out daily or weekly here during plebe summer because uh because life's been hard. And I was uh again, fell victim to my own humanness and wasn't as productive as I could have been or needed to be. Um, but I've been navigating it on my own too. And you know, we're just trying to take advantage and move one step at a time and continue to move forward and take action despite all the things, right? And so again, I continue to be on this journey with all of you. And uh again, I I just believe that like we are all on this journey together with one another. So um, if I can ever be a support, please let me know. I appreciate you all. Congratulations. Happy Barons weekend and have a good day.

Support, Gratitude, And Closing

SPEAKER_00 19:35

Thank you so much for listening to this episode of the Academy Insider Podcast. I really hope you liked it, enjoyed it, and learned something during this time. If you did, please feel free to like and subscribe or leave a comment about the episode. We really appreciate to hear your feedback about everything and continue to make Academy Insider an amazing service that guides, serves, and supports midshipmen, future midshipmen, and their families. Thank you.